Fla Van One

19 May 2008 SciFinder Scholar Page: 1
flavanone
Research Topic task started on Mon May 19, 2008 at 12:07 PM
2 Research Topic candidates were identified in CAPLUS and MEDLINE.
using the phrase "flavanone"
Selected 1 of 2 candidate topics.

5697 references were found containing "flavanone" as entered.
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Task History
flavanone
Answer 1:
Bibliographic Information
Flavanone 3β-hydroxylases from rice: key enzymes for favonol and anthocyanin biosynthesis. Kim, Jeong Ho; Lee, Yoon
Jung; Kim, Bong Gyu; Lim, Yoongho; Ahn, Joong-Hoon. Department of Bioscience and Biotechnology, Bio/Molecular Informatics
Center, Konkuk University, Seoul, S. Korea. Molecules and Cells (2008), 25(2), 312-316. Publisher: Korean Society for
Molecular and Cellular Biology, CODEN: MOCEEK ISSN: 1016-8478. Journal written in English. AN 2008:594032 CAPLUS
(Copyright (C) 2008 ACS on SciFinder (R))
Abstract
Flavanone 3β-hydroxylases (F3H) are key enzymes in the synthesis of flavonol and anthocyanin. In this study, three F3H cDNAs
from Oryza sativa (OsF3H-1 .apprx.3) were cloned by RT-PCR and expressed in E. coli as glutathione S-transferase (GST) fusion
proteins. The purified recombinant OsF3Hs used flavanone, naringenin and eriodictyol as substrates. The reaction products with
naringen and eriodictyol were detd. by NMR spectroscopy to be dihydrokaempferol and taxifolin, resp. OsF3H-1 had the highest
enzymic activity whereas the overall expression of OsF3H-2 was highest in all tissues except seeds. Flavanone 3β-hydroxylase could
be a useful target for flavonoid metabolic engineering in rice.
Answer 2:
Accumulation of flavonols in response to ultraviolet-B irradiation in soybean is related to induction of flavanone

3-β-hydroxylase and flavonol synthase. Kim, Bong Gyu; Kim, Jeong Ho; Kim, Jiyoung; Lee, Choonghwan; Ahn, Joong-Hoon.
Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Seoul, S. Korea. Molecules
and Cells (2008), 25(2), 247-252. Publisher: Korean Society for Molecular and Cellular Biology, CODEN: MOCEEK ISSN:
1016-8478. Journal written in English. AN 2008:594022 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
There are several branch points in the flavonoid synthesis pathway starting from chalcone. Among them, the hydroxylation of
flavanone is a key step leading to flavonol and anthocyanin. The flavanone 3-β-hydroxylase (GmF3H) gene was cloned from
soybean (Glycine max cultivar Sinpaldal) and shown to convert eriodictyol and naringenin into taxifolin and dihydrokaempferol, resp.
The major flavonoids in this soybean cultivar were found by LC-MS/MS to be kamepferol O-triglycosides and O-diglycosides.
Expression of GmF3H and flavonol synthase (GmFLS) was induced by UV-B (UV-B) irradn. and their expression stimulated
accumulation of kaempferol glycones. Thus, GmF3H and GmFLS appear to be key enzymes in the biosynthesis of the
UV-protectant, kaempferol.
Answer 3:
Extracting of total flavanone from green pepper and its effects on cavenging of hydroxyl radicals. Fang, Xiao-yan; You,
Ting-ting; Lin, Dan-ying; Huang, Suo-yi. Baise Agriculture School in Guangxi, Baise, Guangxi, Peop. Rep. China. Weiliang Yuansu
Yu Jiankang Yanjiu (2008), 25(2), 46-47. Publisher: Weiliang Yuansu Yu Jiankang Yanjiu Zazhishe, CODEN: WYYJAF ISSN:
1005-5320. Journal written in Chinese. AN 2008:588629 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
flavanone
In order to make use of the resources of green pepper, avoid wasting and approach the extn. of total flavanone of green pepper and
its effects on scavenging of hydroxyl radicals. The flavonoids were extd. by ethanol as the solvent from green pepper with ultrasonic
wave and ethanol extn. Using spectrophotometry to ext. and check the flavanone of green pepper. The effect of exts. on green
pepper scavenging of hydroxyl radicals was studied. By this method getting the d. of the total flavanone of green pepper is C = 0.192
mg/mL and the rate of recovery is 100.9%. This text provides the extn. and purifying methods to get the outcome and the purity of
the flavanone are all very high. This method is a purely phys. process and has not any pollution. It is an ideal way to ext. the
flavanone of green pepper. Total Flavanone from green pepper have effects on scavenging of hydroxyl radicals.
Answer 4:
Preparation of novel β-cyclodextrin chiral stationary phase based on click chemistry. Zhang, Yongping; Guo, Zhimou; Ye,
Jinxing; Xu, Qing; Liang, Xinmiao; Lei, Aiwen. School of Pharmacy, East China University of Science and Technology, 130 Meilong
Road, Shanghai, Peop. Rep. China. Journal of Chromatography, A (2008), 1191(1-2), 188-192. Publisher: Elsevier B.V.,
CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. AN 2008:577844 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
A facile strategy based on click chem. for prepn. of the structurally well-defined native β-cyclodextrin (β-CD) based chiral stationary
phase (CSP) was proposed. The β-CD CSP was evaluated by enatiosepn. of benzoin, trans-stilbene oxide, Troger's base,
bendroflumethiazide, ketoprofen, chlorthalidone, three flavanone compds. and two β-adrenergic blocking agents under reversed phase
high performance liq. chromatog. The chromatog. results demonstrate the chiral sepn. ability of click β-CD CSP and illustrate the
usefulness of click chem. in the prepn. of β-CD based CSP.
Answer 5:
Constituents of the aerial part of Dryopteris sublaeta Ching et Hsu. Zheng, Xiaoke; Dong, Sanli; Feng, Weisheng. Basic
Medical College, Henan College of Traditional Chinese Medicine, Zhengzhou, Henan, Peop. Rep. China. Proceedings of the China
Association for Science and Technology (2008), Volume Date 2007, 4(1), 873-874. Publisher: Science Press, CODEN: PCASCX
Journal written in English. AN 2008:539691 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
To study the chem. constituents of the aerial part of Dryopteris sublaeta Ching et Hsu. The column of silica gel was employed for the
isolation and purifn. of the compds. from Dryopteris sublaeta Ching et Hsu. The structures of the compds. were identified by
physiochem. properties and spectral anal. Five compds. were isolated from the ether fraction of 70% acetone-exts., and their
structures were identified as (2S)-5, 7-dihydroxy-6, 8-dimethyl flavanone (desmethoxy-matteucinol)(I), (2S)-5,
7-dihydroxy-4'-methoxyl-6, 8-dimethyl flavanone (matteucinol)(II), (2S)-5, 7, 2'-trihydroxy-6, 8-dimethyl flavanone(III), (2S)-5, 7,
4'-trihydroxy-6, 8-dimethyl-3'-methoxyl flavanone(IV), (2S)-5-hydroxy-6, 8-dimethyl-4'-methoxyl-7-O-β-D - glucosyl flavanone(V). All
the compds. were isolated from the aerial part of this plant for the first time.
Answer 6:
Plant-derived polyphenols attenuate lipopolysaccharide-induced nitric oxide and tumour necrosis factor production in
flavanone
murine microglia and macrophages. Shanmugam, Kirubakaran; Holmquist, Lina; Steele, Megan; Stuchbury, Grant; Berbaum,
Katrin; Schulz, Oliver; Garcia, Obdulio Benavente; Castillo, Julian; Burnell, Jim; Rivas, Vernon Garcia; Dobson, Geoff; Munch, Gerald.
Biochemistry and Molecular Biology, James Cook University, Townsville, Australia. Molecular Nutrition & Food Research (2008),
52(4), 427-438. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: MNFRCV ISSN: 1613-4125. Journal written in English.
AN 2008:533397 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
Lipopolysaccharides released during bacterial infections induce the expression of pro-inflammatory cytokines and lead to complications
such as neuronal damage in the CNS and septic shock in the periphery. While the initial infection is treated by antibiotics,
anti-inflammatory agents would be advantageous add-on medications. In order to identify such compds., we have compared 29 com.
available polyphenol-contg. plant exts. and pure compds. for their ability to prevent LPS-induced up-regulation of NO prodn. Among
the botanical exts., bearberry and grape seed were the most active prepns., exhibiting IC50 values of around 20 μg/mL. Among the
pure compds., IC50 values for apigenin, diosmetin and silybin were 15, 19 and 12 μM, in N-11 murine microglia, and 7, 16 and 25 μM,
in RAW 264.7 murine macrophages, resp. In addn., these flavonoids were also able to down-regulate LPS-induced tumor necrosis
factor prodn. Structure-activity relationships of the flavonoids demonstrated three distinct principles: (i) flavonoid-aglycons are more
potent than the corresponding glycosides, (ii) flavonoids with a 4'-OH substitution in the B-ring are more potent than those with a
3'-OH-4'-methoxy substitution, (iii) flavonoids of the flavone type (with a C2=C3 double bond) are more potent than those of the
flavanone type (with a at C2-C3 single bond).
Answer 7:
Analysis of flavonoids and characterization of the OsFNS gene involved in flavone biosynthesis in rice. Kim, Jeong Ho;
Cheon, Young Min; Kim, Bong-Gyu; Ahn, Joong-Hoon. Department of Bioscience and Biotechnology, Bio/Molecular Informatics
Center, Konkuk University, Seoul, S. Korea. Journal of Plant Biology (Seoul, Republic of Korea) (2008), 51(2), 97-101.
Publisher: Botanical Society of Korea, CODEN: JPBIEZ ISSN: 1226-9239. Journal written in English. AN 2008:530865 CAPLUS
Abstract
The major flavonoids in rice leaves were analyzed via LC-MS/MS after their total flavonoid exts. were hydrolyzed. The most abundant
flavones were apigenin, luteolin, and tricetin. Of these, tricetin was methylated at its 3' and 5'-hydroxyl group to form tricin, which was
probably O-glycosylated. Both 3'-O-methylated luteolin and luteolin were found in the C-glycosylated form while apigenin was
C-glycosylated. We also cloned and characterized OsFNS, which catalyzes the reaction from flavanone (naringenin) to flavone
(apigenin). Anal. of the reaction product with recombinant OsFNS showed that it indeed converts naringenin to apigenin.
Answer 8:
Characterization of interactions between polyphenolic compounds and human serum proteins by capillary electrophoresis.
Diniz, Andrea; Escuder-Gilabert, Laura; Lopes, Norberto P.; Villanueva-Camanas, Rosa Maria; Sagrado, Salvador; Medina-Hernandez,
Maria Jose. Departamento de Ciencias Farmaceuticas, CCS, Universidade Estadual de Londrina, Rod. Celso Garcia Cid, PR 445
km 380, Londrina-PR, Brazil. Analytical and Bioanalytical Chemistry (2008), 391(2), 625-632. Publisher: Springer, CODEN:
ABCNBP ISSN: 1618-2642. Journal written in English. AN 2008:524915 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
flavanone
The interaction of ten natural polyphenolic compds. (chlorogenic acid, apigenin, catechin, epicatechin, flavanone, flavone, quercetin,
rutin, vicenin-2 and vitexin) with human serum albumin and mixts. of human serum albumin and α1-acid glycoprotein under near
physiol. conditions is studied by capillary electrophoresis-frontal anal. Furthermore, the binding of these polyphenolic compds. to total
plasmatic proteins is evaluated using ultrafiltration and capillary electrophoresis. In spite of the relatively small differences in the
chem. structures of the compds. studied, large differences were obsd. in their binding behaviors to plasmatic proteins. The
hydrophobicity, the presence/absence of some functional groups, steric hindrance and spatial arrangement seem to be key factors in
the affinity of natural polyphenols towards plasmatic proteins.
Answer 9:
The total flavonoids of longan shell extraction and identification by ultrasonic wave. Huang, Suoyi; Liu, Haihua; Li, Haini;
Tang, Yulian; Zhang, Jingxuan. Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Guangxi Province,
Peop. Rep. China. Shizhen Guoyi Guoyao (2007), 18(2), 461-462. Publisher: Shizhen Guoyi Guoyao Bianweihui, CODEN:
SGGHAL ISSN: 1008-0805. Journal written in Chinese. AN 2008:511674 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
The method for extn. and identification of total flavonoids of longan shell was studied. The flavonoids were extd. by ethanol as the
solvent from longan shell with ultrasonic wave. Spectrophotometry was used to det. the flavanone of longan shell. The content of the
total flavonoids of longan shell obtained by this method was C=1.204 mg/mL, and the rate of recovery was 98.29%. This text
provided the extn. and purifn. methods to get outcome, and the purity of the flavonoids was high. This method was a purely phys.
process and had no pollution, and it was an ideal way to ext. the flavonoids of longan shell.
Answer 10:
In vitro antimalarial activity of prenylated flavonoids from Erythrina fusca. Khaomek, Pranorm; Ichino, Chikara; Ishiyama,
Aki; Sekiguchi, Hitomi; Namatame, Miyuki; Ruangrungsi, Nijsiri; Saifah, Ekarin; Kiyohara, Hiroaki; Otoguro, Kazuhiko; Omura, Satoshi;
Yamada, Haruki. Faculty of Science, Rangsit University, Pathumthani, Thailand. Journal of Natural Medicines (2008), 62(2),
217-220. Publisher: Springer Japan, CODEN: JNMOBN Journal written in English. AN 2008:506032 CAPLUS (Copyright (C)
2008 ACS on SciFinder (R))
Abstract
Et acetate (EtOAc) ext. from the stem bark of Erythrina fusca showed a antimalarial activity against the multi-drug-resistant strain (K1)
of Plasmodium falciparum, and six flavonoids, lupinifolin (1), citflavanone (2), erythrisenegalone (3), lonchocarpol A (4), liquiritigenin
(5), and 8-prenyldaidzein (6), were isolated from the ext. Diprenylated flavanone 4 showed a notable antimalarial activity (IC50; 1.6
μg/mL); however 1 and 3 did not show the activity, even though these compds. possessed prenylated substitution.
Answer 11:
Anti-allergic effect of a combination of Citrus unshiu unripe fruits extract and prednisolone on picryl chloride-induced
contact dermatitis in mice. Fujita, Tadashi; Shiura, Takehumi; Masuda, Megumi; Tokunaga, Masashi; Kawase, Atsushi; Iwaki,
Masahiro; Gato, Takeshi; Fumuro, Masahiko; Sasaki, Katsuaki; Utsunomiya, Naoki; Matsuda, Hideaki. School of Pharmacy, Kinki
University, 3-4-1 Kowakae, Higashiosaka, Osaka, Japan. Journal of Natural Medicines (2008), 62(2), 202-206. Publisher:
flavanone
Springer Japan, CODEN: JNMOBN Journal written in English. AN 2008:506026 CAPLUS (Copyright (C) 2008 ACS on SciFinder
(R))
Abstract
Effect of 50% ethanolic ext. of unripe fruits of Citrus unshiu (CU-ext) on type IV allergic reaction was examd. by inhibitory activity of
ear swelling of picryl chloride-induced contact dermatitis (PC-CD) in mice. Oral administration of CU-ext and s.c. administration of
prednisolone showed inhibition of ear swelling during both induction and effector phases of PC-CD. The inhibitory activities of
combinations of CU-ext (p.o.) and prednisolone (s.c.) during induction phase of PC-CD were more potent than those of CU-ext alone
and prednisolone alone. Successive oral administration of hesperidin, a major flavanone glycoside of CU-ext, inhibited ear swelling
during induction phase of PC-CD. The inhibitory activities of combinations of hesperidin (p.o.) and prednisolone (s.c.) were more
potent than those of hesperidin alone and prednisolone alone. These results indicated that the combinations of prednisolone and
CU-ext or hesperidin exerted a synergistic effect.
Answer 12:
Efficacy of extracting solvents to chemical components of kava (Piper methysticum) roots. Xuan, Tran Dang; Fukuta,
Masakazu; Wei, Ao Chang; Elzaawely, Abdelnaser Abdelghany; Khanh, Tran Dang; Tawata, Shinkichi. Department of Bioscience and
Biotechnology, Faculty of Agriculture, University of the Ryukyus, Okinawa, Japan. Journal of Natural Medicines (2008), 62(2),
188-194. Publisher: Springer Japan, CODEN: JNMOBN Journal written in English. AN 2008:506021 CAPLUS (Copyright (C)
Abstract
The chem. compn. of kava (Piper methysticum) lactones and various phytochems. obtained following the sonication of ground kava
roots extd. in the solvents hexane, chloroform, acetone, ethanol, methanol and water, resp., was analyzed. Eighteen kava lactones,
cinnamic acid bornyl ester and 5,7-dimethoxy-flavanone, known to be present in kava roots, were identified, and seven compds.,
including 2,5,8-trimethyl-1-naphthol, 5-methyl-1-phenylhexen-3-yn-5-ol, 8,11-octadecadienoic acid-Me ester,
5,7-(OH)2-4'-one-6,8-dimethylflavanone, pinostrobin chalcone and 7-dimethoxyflavanone-5-hydroxy-4', were identified for the first
time. Glutathione (26.3 mg/g) was found in the water ext. Dihydro-5,6-dehydrokavain (DDK) was present at a higher level than
methysticin and desmethoxyyagonin, indicating that DDK is also a major constituent of kava roots. Acetone was the most effective
solvent in terms of max. yield and types of kava lactones isolated, followed by water and chloroform, whereas hexane, methanol, and
ethanol were less effective as solvents. Total phenolic and antioxidant activity varied among the extg. solvents, with acetone and
chloroform producing the highest effects, followed by water, while methanol, ethanol and hexane were less effective.
Answer 13:
Plant variety identification method by composition ratio of flavonoids which plant contains. Nakajima, Noriyuki; Shoji,
Kazuaki. (Toyama Prefecture, Japan). Jpn. Kokai Tokkyo Koho (2008), 34pp. CODEN: JKXXAF JP 2008096317 A 20080424
Patent written in Japanese. Application: JP 2006-279333 20061012. Priority: . AN 2008:503213 CAPLUS (Copyright (C) 2008
ACS on SciFinder (R))
Patent Family Information
Patent No. Kind Date Application No. Date

JP 2008096317 A 20080424 JP 2006-279333 20061012
flavanone
Priority Application
JP 2006-279333 20061012
Abstract
A novel plant variety identification method is provided, which has been developed within a shorter time with less expense than the
conventional method. A flavonoid-contg. ext. has been prepd. from an organ tissue (e.g., petal, leaf, fruit, seed, stalk, root) of a plant
(e.g., tulip, chrysanthemum, rose, carnation, orchid, petunia, torenia, spinach, lettuce, rice plant, wheat) at various stages, and
analyzed in comparison. As a result, it has been found that the kinds of various flavonoids (e.g., anthocyanin, flavonol, flavone,
isoflavone, flavanone, flavanol, flavan-3,4-diol, flavan-3-ol, anthocyanidin, auron, chalcone, dihydrochalcone), and their relative amts.
stay const. irresp. of a plant tissue and a plant growth step, but, vary depending on the plant variety. Therefore, the relative amts. of
flavonoids in a flavonoid-contg. ext. could be used for identifying the plant variety.
Answer 14:
Assessment of antibacterial effects of flavonoids by estimation of generation times in liquid bacterial cultures. Ulanowska,
Katarzyna; Majchrzyk, Anna; Moskot, Marta; Jakobkiewicz-Banecka, Joanna; Wegrzyn, Grzegorz. Department of Molecular Biology,
University of Gdansk, Gdansk, Pol. Biologia (Bratislava, Slovakia) (2007), 62(2), 132-135. Publisher: Slovak Academy of
Sciences, CODEN: BLOAAO ISSN: 0006-3088. Journal written in English. AN 2008:497024 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Antibacterial activities of various flavonoids, a group of natural plant substances, have been reported previously, however, there are
contradictory data, published by various authors, regarding sensitivity of particular bacterial species to these compds. These
problems arose apparently because of using different methods by various researchers. Here we tested sensitivity of several bacterial
species (Gram-pos.: Bacillus subtilis, Micrococcus luteus, Sarcina sp. and Staphylococcus aureus; and Gram-neg.: Citrobacter freundii,
Escherichia coli, Klebsiella pneumoniae, Proteus vulgaris, Pseudomonas aeruginosa, Salmonella enterica, Serratia marcescens and
Vibrio harveyi) to various flavonoids: genistein and daidzein (isoflavones), apigenin (a flavone), naringenin (a flavanone) and
kaempferol (a flavonol) by measurement of generation times of bacteria in liq. cultures. The presented results indicate that this simple
method is adequate for unambiguous assessment of sensitivity of bacterial strains to flavonoids.
Answer 15:
High-performance liquid chromatography separation of enantiomers of flavanone and 2'-hydroxychalcone under

reversed-phase conditions. Cirilli, Roberto; Ferretti, Rosella; De Santis, Emiliana; Gallinella, Bruno; Zanitti, Leo; La Torre,
Francesco. Dipartimento del Farmaco, Istituto Superiore di Sanita, Rome, Italy. Journal of Chromatography, A (2008),
1190(1-2), 95-101. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. AN 2008:495223
CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
A reversed-phase high-performance liq. chromatog. (HPLC) method was developed for evaluating the chiral discrimination ability of
Chiralpak IA chiral stationary phase (CSP) towards flavanone. The effect of the nature and pH buffer as well as nature of alc.
flavanone
modifier on enantioselectivity was investigated. Comparative study of enantiosepn. in reversed-phase and polar org. conditions
indicated a significative improvement in resoln. when aq.-based eluents were used. The developed reversed-phase chromatog. method
was able to sep. the enantiomers of flavanone from its isomeric form, the 2'-hydroxychalcone. The stereochem. stability of
flavanone was studied by classical off-column HPLC kinetic procedures in aq. and non-aq. media. It was clearly demonstrated that
the 2'-hydroxychalcone was involved as intermediate in the on-column and off-column enantiomerization process of flavanone.
Answer 16:
Four glucosyltransferases from rice: cDNA cloning, expression, and characterization. Ko, Jae Hyung; Kim, Bong Gyu; Kim,
Jeong Ho; Kim, Hojung; Lim, Chae Eun; Lim, Jun; Lee, Chan; Lim, Yoongho; Ahn, Joong-Hoon. Division of Bioscience and
Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Seoul, S. Korea. Journal of Plant Physiology (2008), 165(4),
435-444. Publisher: Elsevier GmbH, CODEN: JPPHEY ISSN: 0176-1617. Journal written in English. CAN 148:443295 AN
2008:489001 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
Four UDP-dependent glucosyltransferase (UGT) genes, UGT706C1, UGT706D1, UGT707A3, and UGT709A4 were cloned from rice,
expressed in Escherichia coli, and purified to homogeneity. To find out whether these enzymes could use flavonoids as glucose
acceptors, apigenin, daidzein, genistein, kaempferol, luteolin, naringenin, and quercetin were used as potential glucose acceptors.
UGT706C1 and UGT707A3 could use kaempferol and quercetin as glucose acceptors and the major glycosylation position was the
hydroxyl group of carbon 3 based on the comparison of HPLC retention times, UV spectra, and NMR spectra with those of
corresponding authentic flavonoid 3-O-glucosides. UGT709A4 only used the isoflavonoids genistein and daidzein and transferred
glucose onto 7-hydroxyl group. In addn., UGT706D1 used a broad range of flavonoids including flavone, flavanone, flavonol, and
isoflavone, and produced at least two products with glycosylation at different hydroxyl groups. Based on their substrate preferences
and the flavonoids present in rice, the in vivo function of UGT706C1, UGT706D1, and UGT707A3 is most likely the biosynthesis of
kaempferol and quercetin glucosides.
Answer 17:
Chemical components of Rhododendron concinnum. Yang, Shuhui; Tian, Xuan. State Key Laboratory of Applied Organic
Chemistry, Lanzhou University, Lanzhou, Peop. Rep. China. Xibei Zhiwu Xuebao (2007), 27(2), 364-370. Publisher: Kexue
Chubanshe, CODEN: XZXUEV ISSN: 1000-4025. Journal written in Chinese. AN 2008:482521 CAPLUS (Copyright (C) 2008
Abstract
Seventeen compds. were isolated from the ext. of whole Rhododendron concinnum Hemsl. plant by petroleum ether and acetic ester
and structurally identified by modern spectral technol. (MS, 1HNMR, 13CNMR, DEPT and CD) and chem. methodol. They were
(2S)-4',5,7-trihydroxy-flavanone (1), (2R,3R)(+)taxifolin (2), avicularin (3), quercetin-3-O-α-L-rhamnoside (4), hyperoside (5), quercetin
(6), 19-kaurene acid (7), isoscopoletin (8), ledol (9), stigmast-4-en-6β-ol-3-one (10), β-amyrin (11), α-amyrin (12), 28-hydroxy-β-amyrin
(13), uvaol (14), oleanolic acid (15), β-sitosterol (16) and β-daucosterol (17). All of them were isolated from R. concinnum for the first
time, in which (1), (7), (8), (9) and (10) were isolated from Rhododendron genus for the first time.
Answer 18:
flavanone
High-yield anthocyanin biosynthesis in engineered Escherichia coli. Yan, Yajun; Li, Zhen; Koffas, Mattheos A. G.
Department of Chemical and Biological Engineering, University at Buffalo, The State University of New York, Buffalo, NY, USA.
Biotechnology and Bioengineering (2008), 100(1), 126-140. Publisher: John Wiley & Sons, Inc., CODEN: BIBIAU ISSN: 0006-3592.
Abstract
Anthocyanins are red, purple, or blue plant water-sol. pigments. In the past two decades, anthocyanins have received extensive
studies for their anti-oxidative, anti-inflammatory, anti-cancer, anti-obesity, anti-diabetic, and cardioprotective properties. In the
present study, anthocyanin biosynthetic enzymes from different plant species were characterized and employed for pathway
construction leading from inexpensive precursors such as flavanones and flavan-3-ols to anthocyanins in Escherichia coli. The
recombinant E. coli cells successfully achieved milligram level prodn. of two anthocyanins, pelargonidin 3-O-glucoside (0.98 mg/L) and
cyanidin 3-O-gluside (2.07 mg/L) from their resp. flavanone precursors naringenin and eriodictyol. Cyanidin 3-O-glucoside was
produced at even higher yields (16.1 mg/L) from its flavan-3-ol, (+)-catechin precursor. Further studies demonstrated that availability
of the glucosyl donor, UDP-glucose, was the key metabolic limitation, while product instability at normal pH was also identified as a
barrier for prodn. improvement. Therefore, various optimization strategies were employed for enhancing the homogenous synthesis of
UDP-glucose in the host cells while at the same time stabilizing the final anthocyanin product. Such optimizations included culture
medium pH adjustment, the creation of fusion proteins and the rational manipulation of E. coli metabolic network for improving the
intracellular UDP-glucose metabolic pool. As a result, prodn. of pelargonidin 3-O-glucoside at 78.9 mg/L and cyanidin 3-O-glucoside at
70.7 mg/L was achieved from their precursor flavan-3-ols without supplementation with extracellular UDP-glucose. These results
demonstrate the efficient prodn. of the core anthocyanins for the first time and open the possibility for their commercialization for
pharmaceutical and nutraceutical applications.
Answer 19:
Chlorogenic acid and its metabolite m-coumaric acid evoke neurite outgrowth in hippocampal neuronal cells. Ito,
Hideyuki; Sun, Xiu-Lan; Watanabe, Makiko; Okamoto, Motoi; Hatano, Tsutomu. Department of Pharmacognosy, Pharmaceutical
Sciences, Dentistry and Pharmaceutical Sciences, Okayama University Graduate School of Medicine, Tsushima, Okayama, Japan.
Bioscience, Biotechnology, and Biochemistry (2008), 72(3), 885-888. Publisher: Japan Society for Bioscience, Biotechnology, and
Agrochemistry, CODEN: BBBIEJ ISSN: 0916-8451. Journal written in English. AN 2008:453077 CAPLUS (Copyright (C) 2008
Abstract
We evaluated the neurotrophic activity of dietary polyphenols by using primary cultures of fetal rat hippocampal neurons in a
serum-free medium. Among the tested compds., chlorogenic acid and its metabolite, m-coumaric acid, together with catechins and
flavanone, were found to promote neuronal differentiation comparable to the phytochem., honokiol, which has been reported to show
potent neurotrophic activity. The present findings may contribute to the development of further neurotrophic studies on dietary
polyphenols and their metabolites.
Answer 20:
Characterization of Phenolic Compounds in Rooibos Tea. Krafczyk, Nicole; Glomb, Marcus A. Institute of Chemistry Food
Chemistry, Martin Luther University Halle-Wittenberg, Halle, Germany. Journal of Agricultural and Food Chemistry (2008), 56(9),
3368-3376. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. AN
flavanone
Abstract
Polyphenols present in rooibos, a popular herbal tea from Aspalathus linearis, were isolated in two steps. First, phenolic ingredients
were sepd. by multilayer countercurrent chromatog. (MLCCC). Preparative high-performance liq. chromatog. (HPLC) was then applied
to obtain pure flavonoids. The purity and identity of isolated compds. was confirmed by different NMR expts., HPLC-diode array
detector (DAD), or gas chromatog.-mass spectrometry (GC-MS) anal. This strategy proved to be valid to isolate material in up to gram
quantities and to verify known and previously not published polyphenol structures. In addn. the chem. of dihydrochalcones and
related intermediates was studied. The dihydrochalcone aspalathin was oxidized to the corresponding flavanone-C-glycosides
((R)/(S)-eriodictyol-6-C-β-D-glucopyranoside and (R)/(S)-eriodictyol-8-C-β-D-glucopyranoside). Flavanone-6-C-β-D-glucopyranosides
were further degraded to flavones isoorientin and orientin.
Answer 21:
Characterization of dihydroflavonol 4-reductases for recombinant plant pigment biosynthesis applications. Leonard,
Effendi; Yan, Yajun; Chemler, Joseph; Matern, Ulrich; Martens, Stefan; Koffas, Mattheos A. G. Department of Chemical and
Biological Engineering, the State University of New York at Buffalo, Buffalo, NY, USA. Biocatalysis and Biotransformation
(2008), 26(3), 243-251. Publisher: Informa Healthcare, CODEN: BOBOEQ ISSN: 1024-2422. Journal written in English. AN
Abstract
Anthocyanins are colorful plant pigments with promising applications as pharmaceuticals and colorants. In order to engineer efficient
pigment biosynthesis in Escherichia coli, the activities of various dihydroflavonol 4-reductases (DFRs) were characterized for the three
primary dihydroflavonol substrates. The biochem. assays demonstrated variable DFR activities for dihydroflavonol with one B-ring
hydroxyl group, the precursor of pelargonidin derivs. In contrast, dihydroflavonols with two and three B-ring hydroxylation were
metabolized with comparable efficiency. Furthermore, the catalysis of DFR for the secondary substrates, flavanones, also depended
on the no. of B-ring hydroxyl groups. Engineering the expression of the DFR clones together with plant-specific 4-coumaroyl:CoA
ligase, chalcone synthase, chalcone isomerase, and flavanone 3-hydroxylase in E. coli resulted in the synthesis of pelargonidin at
various levels, from p-coumaric acids. The identification of a robust DFR from this study can also be used for engineering
recombinant synthesis of other bioactive flavonoids, such as flavan-3-ols.
Answer 22:
Studies on chemical constituents of sarcandra glabra. Zhu, Liping; Li, Yuan; Yang, Jingzhi; Zuo, Li; Zhang, Dongming.
Ministry of Education Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Institute of
Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peop. Rep. China. Zhongguo
Zhongyao Zazhi (2008), 33(2), 155-157. Publisher: Zhongguo Zhongyao Zazhishe, CODEN: ZZZAE3 ISSN: 1001-5302. Journal
written in Chinese. AN 2008:446437 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
The objective was to study the chem. constituents of the whole plant of Sarcandra glabra. The compds. were isolated by various
chromatog. techniques and their structures were elucidated by their physicochem. properties and the anal. of their spectral data.
Seven compds. were isolated and identified as isofraxidin(1), hemidesmin-1(2), (-)-(7S, 8R)-Dihydro-dehydrodiconiferyl alc.(3), N-trans-
feruloyl tyramine(4), methy rosmarinate (5), Et rosmarinate(6), (+)-3, 3', 5, 5', 7-pentahydro flavanone(7). Compds. 2-4, 6, 7 were
isolated from S.glabra for the first time.
flavanone
Answer 23:
Microbial transformations of flavanone by Aspergillus niger and Penicillium chermesinum cultures. Kostrzewa-Suslow,
Edyta; Dmochowska-Gladysz, Jadwiga; Bialonska, Agata; Ciunik, Zbigniew. Department of Chemistry, Wroclaw University of
Environmental and Life Sciences, Norwida 25, Wroclaw, Pol. Journal of Molecular Catalysis B: Enzymatic (2008), 52-53 34-39.
Publisher: Elsevier B.V., CODEN: JMCEF8 ISSN: 1381-1177. Journal written in English. AN 2008:442489 CAPLUS (Copyright
(C) 2008 ACS on SciFinder (R))
Abstract
As a result of biotransformation of flavanone (1) by the strain Aspergillus niger MB (being the UV mutant) and by the wild strain
Penicillium chermesinum 113 the products of hydroxylation at C-6 (2) and C-4' (5) were obtained. Addnl., three dihydrochalcones with
hydroxyl groups at C-2' (4), C-2' and C-5' (3) and C-2' and C-4 (6) were formed.
Answer 24:
Base catalysis via amine-functionalized mesoporous silicas with various structural phases. Sujandi; Park, Sang-Eon. Lab.
of Nano-Green Catalysis and Nano Center for Fine Chemicals Fusion Technology, Dep't of Chemistry, Inha University, Incheon, S.
Korea. Studies in Surface Science and Catalysis (2007), 170B(From Zeolites to Porous MOF Materials), 1446-1453. Publisher:
Elsevier B.V., CODEN: SSCTDM ISSN: 0167-2991. Journal written in English. AN 2008:428200 CAPLUS (Copyright (C) 2008
Abstract
Chloropropyl functionalized mesoporous silicas with various structural phases such as hexagonal p6mm, cubic Ia3d, and cubic Im3m
have been synthesized from the co-condensation of sodium metasilicate and 3-chloropropyltrimethoxysilane (CPTS) in a P123 or
F127/HCl/H2O system. The mesostructural phase of the mesoporous silicas was closely related with the amt. of CPTS in the initial
synthesis gels when P123 was used as the structure directing agent. On the other hand, the amt. of CPTS did not alter the
mesostructure of the materials when F127 was used as the structure directing agent. The tetraalkyl quaternary ammonium hydroxide
functionalized mesoporous silica catalysts were prepd. from the obtained chloropropyl-functionalized mesoporous silicas. Over these
catalysts we conducted Claisen-Schmidt condensation of benzaldehyde and 2'-hydroxyacetophenone and subsequent Michael addn. to
give a pharmaceutically important flavanone compd. The catalyst with Ia3d phase showed higher catalytic activity which was
supposed due to the favorable diffusion and mass transfer of substrate mols. into the bicontinuous cubic interwoven pore structure
than other cubic and hexagonal structures.
Answer 25:
Research progress of the protective effect of flavonoids on experimental liver injury of animals. Guo, Jingjing; Yang, Xiufen.
Department of Pharmacology, School of Pharmaceutical Sciences, Guangxi Traditional Chinese Medical University, Nanning, Peop.
Rep. China. Zhongguo Yaolixue Tongbao (2008), 24(1), 5-10. Publisher: Anhui Yike Daxue Linchuan Yaoli Yanjiuso, CODEN:
ZYTOE8 ISSN: 1001-1978. Journal; General Review written in Chinese. AN 2008:412684 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
flavanone
A review with 35 refs. on the research progress of the protective effect of flavonoids (such as flavone, flavonol, flavanone,
isoflavone, flavanol and so on) on exptl. liver injury of animals which is induced by chems., drugs, immunostimulation, alc. and
hepatic ischemia reperfusion in some degree, and the kinds of protection are relevant to the function of flavonoids such as elimination
of free radical, resistance of oxidn., resistance of lipid peroxidn., adjustment of immune function and so on.
Answer 26:
Stereochemistry of flavonoidal alkaloids from Dracocephalum rupestre. Ren, Dong-Mei; Guo, Huai-Fang; Yu, Wen-Tao;
Wang, Shu-Qi; Ji, Mei; Lou, Hong-Xiang. Department of Natural Products Chemistry, School of Pharmaceutical Sciences, Shandong
University, Jinan, Peop. Rep. China. Phytochemistry (Elsevier) (2008), 69(6), 1425-1433. Publisher: Elsevier Ltd., CODEN:
PYTCAS ISSN: 0031-9422. Journal written in English. AN 2008:404202 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
Phytochem. studies on the aerial parts of Dracocephalum rupestre led to the isolation of four groups of flavonoidal alkaloids,
dracocephins A-D. They were elucidated as conjugates of flavanone with pyrrolidin-2-one on the basis of extensive spectroscopic
anal. The two stereogenic centers rendered each group of the dracocephins as two pairs of enantiomers simultaneously. All of the
sixteen isomers were sepd. successfully by chiral HPLC and their stereochem. features were detd. by their CD data and single-crystal
X-ray diffraction anal. of one stereoisomer. The additive relation of the chiroptical contributions resulting from the two stereogenic
centers was generalized. The CD contribution of the chiral carbon in the pyrrolidin-2-one ring was proposed by subtraction of their resp.
contributions.
Answer 27:
Process for the preparation of a cosmetic composition from a plant extract comprising polysaccharides. Chevalier,
Veronique; Nguyen, Quang Lan. (L'Oreal, Fr.). PCT Int. Appl. (2008), 31pp. CODEN: PIXXD2 WO 2008034718 A1 20080327
Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM,
DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK,
LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD,
SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS,
IT, LU, MC, MT, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application:
WO 2007-EP59240 20070904. Priority: FR 2006-53838 20060920; US 2006-848368 20061002. CAN 148:362905 AN

WO 2008034718 A1 20080327 WO 2007-EP59240 20070904
W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE,
DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE,
KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ,
NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM,
TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW
RW: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LT, LU, LV, MC, MT, NL, PL,
PT, RO, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG, BW, GH,
GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM
flavanone
FR 2905863 A1 20080321 FR 2006-53838 20060920
FR 2006-53838 A 20060920
US 2006-848368P P 20061002
Abstract
This invention relates to process for the prepn. of a cosmetic compn. for topical application comprising a stage of percolation of plant
exts. followed by the incorporation of this ext. in a concd. prepn. The plant substances comprising polysaccharides are chosen in
particular from algae and plants comprising gums or pectin. The invention also relates to the compn. obtained and to its use in the
cosmetics field, in particular on the skin. Thus, tea leaves 2 g and Laminaria digitata alga powder 3 g were placed in a capsule and the
capsule was placed in a com. expresso machine. The steam produced by the machine subsequently passes through this pulverulent
mixt. until an ext. of 59 mL was obtained. The ext. was collected in the following prepn. (O/W emulsion 41 g): PEG 8 isostearate 5.85
g, hydrogenated polyisobutene 12.7 g, cyclic silicone 10 g, disodium stearoylglutamate 0.15 g, and water 12.3 g.
Answer 28:
Process for the preparation of a cosmetic composition having a lightening effect on the skin. Nguyen, Quang Lan;
Chevalier, Veronique. (L'Oreal, Fr.). PCT Int. Appl. (2008), 28pp. CODEN: PIXXD2 WO 2008034700 A1 20080327 Designated
States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ,
EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS,
LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG,
SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU,
MC, MT, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO
2007-EP59008 20070829. Priority: FR 2006-53840 20060920; US 2006-848370 20061002. CAN 148:362902 AN 2008:380444

WO 2008034700 A1 20080327 WO 2007-EP59008 20070829
FR 2905865 A1 20080321 FR 2006-53840 20060920
FR 2006-53840 A 20060920
US 2006-848370P P 20061002
flavanone
Abstract
This invention relates to a process for the prepn. of a compn. for topical application, characterized in that it comprises a stage of
percolation of fluid under pressure through at least one plant substance in the solid or pasty form chosen from plant substances
comprising coumarin sugar derivs. Plant substances comprising vitamin C can also be combined therewith. The invention also relates
to the compn. obtained and to its use in the cosmetics field, in particular for lightening the skin.
Answer 29:
Differential effects of dietary flavonoids on reactive oxygen and nitrogen species generation and changes in antioxidant
enzyme expression induced by proinflammatory cytokines in Chang Liver cells. Crespo, Irene; Garcia-Mediavilla, Maria V.;
Almar, Mar; Gonzalez, Paquita; Tunon, Maria J.; Sanchez-Campos, Sonia; Gonzalez-Gallego, Javier. Ciberehd and Institute of
Biomedicine, University of Leon, Leon, Spain. Food and Chemical Toxicology (2008), 46(5), 1555-1569. Publisher: Elsevier Ltd.,
CODEN: FCTOD7 ISSN: 0278-6915. Journal written in English. AN 2008:366191 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
This study was aimed to investigate the differential protective effect of dietary flavonoids against oxidative stress induced by
proinflammatory stimuli in parenchymal liver cells. Chang Liver cells were incubated with a cytokine mixt. (CM) supplemented with the
flavonols quercetin and kaempferol, the flavanone taxifolin and the flavone apigenin (5-50 μM). Concns. of oxidised and reduced
glutathione, generation of different ROS/RNS, and expression of antioxidant enzymes were measured. Oxidised glutathione concn.
and the oxidised/reduced glutathione ratio were increased by the CM. These effects were significantly prevented by quercetin,
kaempferol and taxifolin at all tested concns. Effects of apigenin reached a lesser extent and were not significant at 25 μM.
Treatment with quercetin and kaempferol prevented the prodn. of peroxides, superoxide anion and nitric oxide induced by CM. Taxifolin
50 μM and apigenin 25-50 μM caused a significant increase in peroxides and nitric oxide generation. Protein concn. of the different
antioxidant enzymes was generally reduced by kaempferol and quercetin in comparison to CM, although quercetin 25 and 50 μM
increased Mn SOD protein concn. GPx protein level was significantly increased by apigenin 25 and 50 μM. Changes in mRNA tended
to be parallel to those in protein concn. Our study reveals that important differences exist between flavonoids with different structural
features in their capacity to abrogate the generation of different ROS/RNS, and suggests that the modulation of antioxidant enzymes
by flavonoids may be also important in their antioxidant effects in liver cells.
Answer 30:
Determination of total flavanone content in Potentilla discolor bunge by ultraviolet spectrophotometry. Jin, Quan; Lian,
Li-hua; Luo, Hui-shan. Yanbian University College of Pharmacy, Yanji, Jilin, Peop. Rep. China. Yanbian Daxue Yixue Xuebao
(2007), 30(4), 262-263. Publisher: Yanbian Daxue, CODEN: YDYXF5 Journal written in Chinese. AN 2008:365575 CAPLUS
Abstract
OBJECTIVE To study assay method of total content in Potentilla discolor bunge. METHODS With AlCl3-NaNO2-NaOH as
chromogenic agent, total flavanone content of Potentilla discolor bunge is detd. by UV spectrophotometry. RESULTS The optimal
detective wavelength was 510 nm, and absorbility and mass concn. was satisfactory linear relationship at the mass concn. of rutin
was in 20 .apprx. 50mg/L. The regression equation was y = 7.7457x + 0.0009 (r = 0.9996), and the av. recovery rate was 99.52% and
flavanone
RSD was 1.23%. CONCLUSION Using UV spectrophotometry to detect total flavanone content in Potentilla discolor bunge is simple,
accurate, and sensitive.
Answer 31:
HPLC separation of naringin, neohesperidin and their C-2 epimers in commercial samples and herbal medicines.
Uchiyama, Nahoko; Kim, Ik Hwi; Kikura-Hanajiri, Ruri; Kawahara, Nobuo; Konishi, Tenji; Goda, Yukihiro. National Institute of Health
Sciences (NIHS), Tokyo, Japan. Journal of Pharmaceutical and Biomedical Analysis (2008), 46(5), 864-869. Publisher: Elsevier
B.V., CODEN: JPBADA ISSN: 0731-7085. Journal written in English. AN 2008:361176 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
Flavanone glycosides, such as naringin and neohesperidin, are distributed in some Citrus species and have a chiral center in the C-2
position of the flavanone moiety. Naringin and neohesperidin (2S-form) were sepd. from the corresponding C-2 epimers (2R-epi-form)
by normal-phase HPLC using a polysaccharide-derived chiral stationary phases (CSPs), CHIRALPAK IB. The analyses of com.
samples of naringin revealed that the relative ratios of naringin to the C-2 epimer were 29-89%. In the case of a com. sample of
neohesperidin, the relative ratio of the neohesperidin (2S-form) is 84%. The HPLC application to Citrus species used as crude drugs in
Japan (Kijitsu, Kikoku and Tohi) showed that the relative ratios of naringin to the C-2 epimer were 75-93% in Kijitsu, 74-79% in Kikoku
and 54-64% in Tohi. However, there is a quite small ratio of the (2R)-epi-neohesperidin in Citrus. This result suggested that the avs.
of relative ratio of (2S)-naringin in Citrus species reduced according to the maturity of fruits (Kijitsu < Kikoku < Tohi). Since the
relative ratios of (2S)-naringin of dry exts. of 5 Kampo formulations (including Kijitsu or Kikoku) decreased to 42-54%, the conversion
from naringin to the (2R)-epimer might be enhanced during the decoction process of the formulations.
Answer 32:
Scavenging activities of seven natural flavonoids for superoxide anion radicals. Li, Mingjing; Qing, Weixia; Yang, Yuxia;
Zhao, Dongbao; Liu, Xiuhua; Liu, Kuaizhi. College of Chemical and Chemical Engineering, Henan University, Kaifeng, Henan
Province, Peop. Rep. China. Huaxue Yanjiu (2006), 17(4), 73-75. Publisher: Huaxue Yanjiu Bianjibu, CODEN: HUYAF4 ISSN:
1008-1011. Journal written in Chinese. CAN 148:347276 AN 2008:295542 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
Scavenging activities of seven natural flavonoids from Elsholtzia bodinieri vaniot and Artemisia ordosica kraschen for superoxide anion
radicals was studied by single-sweep oscillopolarog. Results showed that the scavenging activities of the flavonoids for O2- were
related with the no. of hydroxyl groups in the flavonoids. The more nos. of hydroxyl groups, the more active is the flavonoid. The
C2-C3 double bond is also contributed to scavenging O2-. The glucoside of flavanone has reduced scavenging ability because of
steric hindrance.
Answer 33:
The extraction and identification of total flavonoids from Houttuynia cordata Thunb. by ultrasonic wave. Huang, Suoyi;
Wan, Chengjun; Zou, Yongfang; Li, Rong. Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Guangxi
Province, Peop. Rep. China. Shizhen Guoyi Guoyao (2006), 17(11), 2261-2262. Publisher: Shizhen Guoyi Guoyao Bianweihui,
flavanone
CODEN: SGGHAL ISSN: 1008-0805. Journal written in Chinese. AN 2008:295415 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
In order to make use of the resources of Houttuynia cordata Thunb., the extn. identification of total flavonoids of Houttuynia cordata
Thunb. was approached. The flavonoids were extd. by ethanol as the solvent from Houttuynia cordata Thunb. with ultrasonic wave and
ethanol extn. Using spectrophotometry to ext. and check the flavanone of Houttuynia cordata Thunb.. The content of total flavonoids
of Houttuynia cordata Thunb. was C=6.48%, and the rate of recovery was 102.4%. The outcome and the purity of the flavanone were
all very high. This method was a purely phys. process, and had not any pollution. It was an ideal way to ext. the flavonoids of
Houttuynia cordata Thunb..
Answer 34:
Separation of flavanone enantiomers and flavanone glucoside diastereomers from Balanophora involucrata Hook. f. by
capillary electrophoresis and reversed-phase high-performance liquid chromatography on a C18 column. Pan, Jianyu;
Zhang, Si; Yan, Liushui; Tai, Jiandong; Xiao, Qiang; Zou, Kun; Zhou, Yuan; Wu, Jun. Guangdong Key Laboratory of Marine Materia
Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, Peop. Rep. China. Journal of
Chromatography, A (2008), 1185(1), 117-129. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in
English. AN 2008:288249 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
A pair of flavanone glucoside diastereomers, (2R)- and (2S)-eriodictyol-5-O-β-D-glucopyranoside (1a, 1b), was successfully sepd. by
RP-C18 high-performance liq. chromatog. from Balanophora involucrata Hook. f. Some other compds., including a pair of flavanone
enantiomers, (2R)- and (2S)-eriodictyol (2a, 2b), and a pair of flavanone glucoside diastereomers, (2R)- and
(2S)-eriodictyol-7-O-β-D-glucopyranoside(3a, 3b), were sepd. by capillary electrophoresis from the same plant. The abs. configurations
at C-2 of 1a and 1b were detd. based on their CD spectra. Enzymic hydrolysis of 1a and 1b by β-D-glucosidase afforded (2R)- and
(2S)-eriodictyol, resp., which were used as the authentic stds. for co-elution to det. the migration order of the enantiomers, 2a and 2b.
We also report the first example of identifying the migration order of 2a and 2b and resolving the sepn. of 3a and 3b by capillary
electrophoresis. In addn., 1a was unambiguously characterized for the first time by NMR spectra.
Answer 35:
Bioconversion by functional P450 1A9 and P450 1C1 of Anguilla japonica. Uno, Tomohide; Okamoto, Sota; Masuda, Satoko;
Imaishi, Hiromasa; Nakamura, Masahiko; Kanamaru, Kengo; Yamagata, Hiroshi; El-Kady, Mohamed A. H.; Kaminishi, Yoshio; Itakura,
Takao. Laboratory of Biological Chemistry, Department of Biofunctional Chemistry, Faculty of Agriculture, Kobe University,
Nada-ku, Kobe, Hyogo, Japan. Comparative Biochemistry and Physiology, Part C: Toxicology & Pharmacology (2008), 147C(3),
278-285. Publisher: Elsevier B.V., CODEN: CBPPFK ISSN: 1532-0456. Journal written in English. CAN 148:420050 AN
Abstract
We indicated that two P450s (1A9 and 1C1) from Japanese eel (Anguilla japonica) metabolized 7-ethoxycoumarin, 7-ethoxyresorufin,
and flavanone. At first, we constructed expression vectors for two types of P 450 (1A9 and 1C1). The reduced CO-difference
spectra of Escherichia coli cells transformed with these plasmids showed Soret peaks (450 nm) that were typical of P450s. We
flavanone
performed bioconversion expts. in which substrates were added directly to incubation medium. The resulting metabolite(s) were extd.
and analyzed by high-performance liq. chromatog. and spectrofluorometer. Incubation of 50 nmol 7-ethoxyresorufin with P 450 1C1
yielded 0.773 nmol of deethylated product, whereas 50 nmol 7-ethoxycoumarin resulted in 4.76 nmol. P 450 1A9 metabolized 50 nmol
of 7-ethoxyresorufin and 7-ethoxycoumarin to yield 6.54 and 20.9 nmol of deethylated product, resp. Incubation of 50 nmol flavanone
with P 450 1C1 yielded 1.46 nmol and 0.69 nmol of products, whereas 50 nmol flavanone with P 450 1A9 resulted in 1.10 nmol. In this
system, 4'-hydroxy flavanones were formed by P 450 1A9 and P 450 1C1. P 450 1A9 also metabolized 50 nmol of 17β-estradiol to
yield 4.25 nmol of product. In this system, 2-hydroxy estradiol was formed by P 450 1A9 using 17β-estradiol as a substrate. This
study is the first to identify the substrates that P 450 1C1 and 1A9 metabolize.
Answer 36:
Enantioseparation using urea- and imide-bearing chitosan phenylcarbamate derivatives as chiral stationary phases for
high-performance liquid chromatography. Yamamoto, Chiyo; Fujisawa, Mari; Kamigaito, Masami; Okamoto, Yoshio.
Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Japan.
Chirality (2008), 20(3/4), 288-294. Publisher: Wiley-Liss, Inc., CODEN: CHRLEP ISSN: 0899-0042. Journal written in English.
CAN 148:486007 AN 2008:269268 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
Completely deacetylated chitosan was prepd. by the treatment of com. chitosan with 50% aq. NaOH, and then derivatized into several
new chitosan phenylcarbamate derivs. having a urea and an imide moiety at the 2-position of the glucosamine ring by the reaction with
isocyanate and phthalic anhydride/isocyanate, resp. The chitosan derivs. were coated on macroporous silica gel and evaluated as
chiral stationary phases (CSPs) for HPLC. The chiral recognition ability of the chitosan deriv. was improved using the completely
deacetylated chitosan. Among the novel chitosan derivs., the 3,5-dimethyl-, 3,5-dichloro-, and 3,4-dichlorophenylcarbamate derivs.
possess relatively high chiral resoln. abilities. The CSPs based on the chitosan phenylcarbamate-urea and -imide derivs. were stable in
the presence of chloroform and Et acetate as a component of the eluents, and some racemates were better resolved by such eluents.
The dichlorophenylcarbamate-imide derivs. showed a high chiral recognition for metal acetylacetonate complexes. The
enantiomerization of Al(acac)3 was performed on the chitosan 3,5-dichlorophenylcarbamate-imide deriv. CSP and the resulting
chromatogram showed a 26% (+)-isomer enrichment.
Answer 37:
Dietary intake and major food sources of polyphenols in Finnish adults. Ovaskainen, Marja-Leena; Torronen, Riitta; Koponen,
Jani M.; Sinkko, Harri; Hellstrom, Jarkko; Reinivuo, Heli; Mattila, Pirjo. Department of Health Promotion and Chronic Disease
Prevention, Nutrition Unit, National Public Health Institute, Helsinki, Finland. Journal of Nutrition (2008), 138(3), 562-566.
Publisher: American Society for Nutrition, CODEN: JONUAI ISSN: 0022-3166. Journal written in English. CAN 148:354858 AN
Abstract
Phenolic acids, flavonoids, proanthocyanidins, and ellagitannins are polyphenols that may have beneficial effects on human health
and provide protection against chronic diseases. To date, limited data exist on quant. intake of polyphenols. The aims of this study
were to est. the quant. intakes of polyphenols by using analyzed concns. together with individual food consumption records and to det.
major dietary sources. Analyzed concns. of phenolic acids, anthocyanidins, and other flavonoids, proanthocyanidins, and ellagitannins
(44 total polyphenol compds.) were entered into the national food compn. database, Fineli. The abs. intakes of the polyphenols and the
corresponding food sources were calcd. on the basis of 48-h dietary recalls of 2007 Finnish adults. The mean total intake of
polyphenols was 863 ± 415 mg/d. Phenolic acids comprised the dominant group of polyphenols (75% of total intake) followed by
flavanone
proanthocyanidins (14%) and anthocyanidins and other flavonoids (10%). Due to their high consumption and high concns. of phenolic
acids, coffee and cereals were the main contributors to total polyphenol intake. Berries and berry products were the main source for
anthocyanidins, ellagitannins, and proanthocyanidins, and fruits were the main source for flavonols, flavones, and flavanones. The
results give addnl. support to the recommendations for a varied diet with fruits, berries, cereals, and vegetables.
Answer 38:
Characterization of flavone synthase I from rice. Lee, Yoon Jung; Kim, Jeong Ho; Kim, Bong Gyu; Lim, Yoongho; Ahn,
Joong-Hoon. Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Seoul, S. Korea.
BMB Reports (2008), 41(1), 68-71. Publisher: Korean Society for Biochemistry and Molecular Biology, CODEN: BRMEC2 ISSN:
1976-6696. Journal written in English. CAN 148:396763 AN 2008:258307 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
Flavones are synthesized from flavanones through the action of flavone synthases (FNSs). There are two FNSs, FNS I and II. FNS
I is a sol. dioxygenase present in members of the Apiaceae family and FNS II is a membrane bound cytochrome P 450 enzyme that
has been identified in numerous plant species. In this study, we cloned OsFNS I-1 from rice by RT-PCR, expressed it in E. coli, and
purified the recombinant protein. By NMR anal., we found that OsFNS I-1 converted the flavanone (2S)-naringenin into the flavone,
apigenin. Moreover, we found that the cofactors oxoglutarate, FeSO4, ascorbate and catalase are required for this reaction. OsFNS
I-1 encodes a flavone synthase I. This is the first type I FNS I found outside of the Apiaceae family.
Answer 39:
Prenylated Flavonoid Derivatives from the Bark of Erythrina addisoniae. Waetjen, W.; Suckow-Schnitker, A. K.; Rohrig, R.;
Kulawik, A.; Addae-Kyereme, J.; Wright, C. W.; Passreiter, C. M. Institute of Toxicology, Heinrich-Heine-University, Duesseldorf,
Germany. Journal of Natural Products (2008), 71(4), 735-738. Publisher: American Chemical Society-American Society of
Pharmacognosy, CODEN: JNPRDF ISSN: 0163-3864. Journal written in English. CAN 148:398486 AN 2008:244407 CAPLUS
Abstract
Two new prenylated flavanones, 2S-3'-(2-hydroxy-3-methylbut-3-enyl)licoflavone-4'-Me ether (3)(I) and

2S-3'-(2-hydroxy-3-methylbut-3-enyl)abyssinone II (4)(II), and four known flavanones (1, 2, 5, 6) were isolated from the stem bark of
Erythrina addisoniae. The structures were elucidated on the basis of their spectroscopic and physicochem. data. None of the
compds. showed antioxidative properties. 4'-Methylabyssinone V (1) and abyssinoflavanone VII (6) showed moderate cytotoxic
activity (IC50 = 5 and 3.5 μmol/L, resp.), but apoptosis (caspase-3/7-activation, nuclear fragmentation) was selectively induced by
abyssinoflavanone VII (6).
flavanone
Me Me
R1
HO O
CH 2
HO
I R=OH, R 1 =OMe
R O Me I I R=H, R 1 =OH
Answer 40:
Struthiolanone: a flavanone-resveratrol adduct from Struthiola argentea. Ayers, Sloan; Zink, Deborah L.; Brand, Robert;
Pretorius, Seef; Stevenson, Dennis; Singh, Sheo B. Natural Products Chemistry, Merck Research Laboratories, Rahway, NJ,
USA. Natural Product Communications (2008), 3(2), 189-192. Publisher: Natural Product Inc., CODEN: NPCACO ISSN:
1934-578X. Journal written in English. AN 2008:242713 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
Struthiolanone (1), a flavanone-resveratrol adduct, was isolated from Struthiola argentea. Its structure was detd. by highresoln. mass
spectrometry and 1D- and 2D-NMR spectroscopic techniques. The abs. configuration was detd. by comparison of the CD spectrum of
biflavonoids. This compd. appears to be the first example of a flavanoid-stilbene adduct.
Answer 41:
Antioxidants from supercritical carbon dioxide fluid extracts(SCFE) of bark-peel of eucalyptus globulus. Vankar, Padma
Shree; Tiwari, Vandana; Srivastava, Jyoti. Facility for Ecological and Analytical Testing (FEAT), Indian Institute of Technology,
Kanpur, India. EJEAFChe, Electronic Journal of Environmental, Agricultural and Food Chemistry (2007), 6(11), 2550-2556.
Publisher: EJEAFChe, CODEN: EEJEAT ISSN: 1579-4377.
http://ejeafche.uvigo.es/index.php?option=com_docman&task=doc_download&gid=317&Itemid=33 Journal; Online Computer File
written in English. AN 2008:242478 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
SCF exts. of Eucalyptus globulus and its column chromatographed fractions were evaluated for antioxidant properties by DPPH,
β-carotene-linoleic acid and ESR methods. The SCF ext. of eucalyptus is also found to be suitable as natural food dye in sweet
prepns. Toxicol. tests of the crude ext. as well as the fractions show that these exts. are safe as food additives.
Answer 42:
flavanone
Erigeroflavanone, a Flavanone Derivative from the Flowers of Erigeron annuus with Protein Glycation and Aldose Reductase
Inhibitory Activity. Yoo, Nam Hee; Jang, Dae Sik; Yoo, Jeong Lim; Lee, Yun Mi; Kim, Young Sook; Cho, Jung-Hee; Kim, Jin
Sook. Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine, Daejeon, S. Korea. Journal of
Natural Products (2008), 71(4), 713-715. Publisher: American Chemical Society-American Society of Pharmacognosy, CODEN:
JNPRDF ISSN: 0163-3864. Journal written in English. CAN 148:398484 AN 2008:239739 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
A novel 2,3-dioxygenated flavanone, erigeroflavanone, as well as eight known flavonoids and two known γ-pyranone derivs., were
isolated from an Et acetate-sol. ext. of the flowers of Erigeron annuus. The structure of compd. 1 was elucidated by interpretation of
spectroscopic data. All of the isolates were subjected to in vitro bioassays to evaluate their inhibitory activity against advanced
glycation end products formation and rat lens aldose reductase.
OH
OH
OMe
HO O
OH
OH O
O OMe I
Answer 43:
Polyphenols and antioxidant properties of almond skins: influence of industrial processing. Garrido, I.; Monagas, M.;
Gomez-Cordoves, C.; Bartolome, B. Inst. de Fermentaciones Industriales (CSIC), Madrid, Spain. Journal of Food Science
(2008), 73(2), C106-C115. Publisher: Blackwell Publishing, Inc., CODEN: JFDSAZ ISSN: 0022-1147. Journal written in English.
Abstract
Almond (Prunus dulcis [Mill.] D.A. Webb) skins have been proposed as a source of bioactive polyphenols. In this article, the phenolic
compn. and antioxidant activity of almond skins obtained from different processes (blanching [freeze-drying], blanching + drying, and
roasting) were studied. A total of 31 phenolic compds. corresponding to flavan-3-ols (33% to 56% of the total of phenolic compds.
identified), flavonol glycosides (9% to 36%), hydroxybenzoic acids and aldehydes (6% to 26%), flavonol aglycons (1.7% to 18%),
flavanone glycosides (3% to 7.7%), flavanone aglycons (0.69% to 5.4%), hydroxycinnamic acids (0.65% to 2.6%), and
dihydroflavonol aglycons (0% to 2.8%) were detd. in the skins from 3 different varieties of almonds. The total contents of phenolic
compds. identified were significantly (P < 0.05) higher (around 2-fold) in the roasted samples than in the blanched almonds
(freeze-dried). Industrial drying (oven drying) of the blanched almond skins produced an increase (< 2-fold) in the contents of phenolic
compds., although the results were only statistically significant (P < 0.05) for some samples. The antioxidant activity (ORAC values)
flavanone
was higher for the roasted samples (0.803 to 1.08 mmol Trolox/g), followed by the samples subjected to blanching + drying (0.398 to
0.575 mmol Trolox/g) and then the blanched (freeze-dried) samples (0.331 to 0.451 mmol Trolox/g). Roasting is the most suitable type
of industrial processing of almonds to obtain almond skin exts. with the greatest antioxidant capacity.
Answer 44:
Geranylated flavanones from the secretion on the surface of the immature fruits of Paulownia tomentosa. Asai, Teigo; Hara,
Noriyuki; Kobayashi, Sawa; Kohshima, Shiro; Fujimoto, Yoshinori. Department of Chemistry and Materials Science, Graduate School
of Science and Engineering, Tokyo Institute of Technology, Meguro, Tokyo, Japan. Phytochemistry (Elsevier) (2008), 69(5),
1234-1241. Publisher: Elsevier Ltd., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 148:351349 AN
Abstract
Chem. investigation of the methanol ext. of the viscous secretion on the surface of immature fruits of Paulownia tomentosa furnished
nine geranylated flavanones, 6-geranyl-5,7-dihydroxy-3',4'-dimethoxyflavanone (1), 6-geranyl-3',5,7-trihydroxy-4'-methoxyflavanone
(2), 6-geranyl-4',5,7-trihydroxy-3',5'-dimethoxyflavanone (3), 6-geranyl-4',5,5',7-tetrahydroxy-3'-methoxyflavanone (4),
6-geranyl-3,3',5,7-tetrahydroxy-4'-methoxyflavanone (5),
4',5,5',7-tetrahydroxy-6-[6-hydroxy-3,7-dimethyl-2(E),7-octadienyl]-3'-methoxyflavanone (6),
3,3',4',5,7-pentahydroxy-6-[6-hydroxy-3,7-dimethyl-2(E),7-octadienyl]flavanone (7),
3,3',4',5,7-pentahydroxy-6-[7-hydroxy-3,7-dimethyl-2(E)-octenyl]flavanone (8), and
3,4',5,5',7-pentahydroxy-3'-methoxy-6-(3-methyl-2-butenyl)flavanone (9), along with six known geranylated flavanones. Among these,
compds. 4, 6-9 and the known 6-geranyl-3',4',5,7-tetraahydroxyflavanone (diplacone), 6-geranyl-3,3',4',5,7-pentahydroxyflavanone
(diplacol) and 3',4',5,7-pentahydroxy-6-[7-hydroxy-3,7-dimethyl-2(E)-octenyl]flavanone showed potent radical scavenging effects
towards DPPH radicals.
Answer 45:
Metabolite profiling of chalcones and flavanones in tomato fruit. Iijima, Yoko; Suda, Kunihiro; Suzuki, Tatsuya; Aoki, Koh;
Shibata, Daisuke. Kazusa DNA Research Institute, Kisarazu, Japan. Journal of the Japanese Society for Horticultural Science
(2008), 77(1), 94-102. Publisher: Japanese Society for Horticultural Science, CODEN: EGKZA9 ISSN: 1882-3351. Journal written
in English. CAN 148:327000 AN 2008:225782 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
Tomato (Solanum lycopersicum) is one of a group of plants that accumulate chalcones and flavanones. However, the mol. diversity
of chalcones, flavanones, and their conjugate metabolites has not been investigated intensively. Here, we report the profiling of
chalcones and flavanones in fruits of the dwarf tomato cultivar Micro-Tom using liq. chromatog. Fourier transform ion cyclotron
resonance mass spectrometry (LC-FTICR-MS). We identified eriodictyol chalcone and eriodictyol aglycons, along with naringenin
chalcone and naringenin aglycons. To our knowledge, this is the first report that demonstrates the presence of eriodictyol chalcone
and eriodictyol in tomato. We detected 26 conjugate metabolites of chalcones and flavanones. Chem. information obtained
simultaneously by LC-FTICR-MS, including m/z values, MS/MS spectra, UV absorption spectra, and retention times, facilitated the
elucidation of mol. formulas and conjugate structures of the metabolites. Eriodictyol chalcone and eriodictyol conjugates had the same
modification patterns seen in naringenin chalcone and naringenin conjugates. Chalcones and flavanones were much more abundant in
tomato fruit peel than flesh. Accumulation profiles during ripening were classified into three groups. The first group included
metabolites that showed the highest accumulation levels at the breaker stage, and then decreased during ripening. The second group
included metabolites that accumulated to the highest levels at the turning stage, and then decreased at the red stage. The third group
flavanone
included metabolites that accumulated gradually during ripening, and showed the highest accumulation levels at the red stage. These
accumulation profiles were mapped onto a putative modification pathway deduced from conjugate structures. Mapping revealed that
the conjugate metabolites upstream of this pathway accumulated earlier, and those downstream accumulated later during ripening.
This result demonstrated that chalcones and flavanones undergo sequential modification as ripening progresses.
Answer 46:
Preparation and application of Exocarpium Citri Grandis extract. Lin, Renhe; Liu, Deqin. (Peop. Rep. China). Faming
Zhuanli Shenqing Gongkai Shuomingshu (2008), 6pp. CODEN: CNXXEV CN 101124986 A 20080220 Patent written in Chinese.
Application: CN 1005-3279 20070913. Priority: . CAN 148:307070 AN 2008:221646 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))

CN 101124986 A 20080220 CN 2007-10053279 20070913
CN 2007-10053279 20070913
Abstract
The title Exocarpium Citri Grandis ext. is prepd. by extg. effective components from Citrus grandis fruit. The Exocarpium Citri Grandis
ext. comprises flavanone, rutin, naringin, nervonic acid, various vegetable amino acids, and trace elements. The Exocarpium Citri
Grandis ext. has the advantages of high contents of effective components, no bitter taste, and no color, and can be used for
producing health-care food, beautification product, and medicine.
Answer 47:
Polynucleotides and polypeptides to produce transgenic plants with enhanced agronomic traits. Abad, Mark; Adams, Tom
R.; Alvarez, Julie; Anuradha, Mahindra; Augustine, Alice Clara; Badami, Pranesh; Bell, Erin; Bennett, Kristen; Bensen, Robert;
Castiglioni, Paolo; Cerny, R. Eric; Chen, Xianfeng; Chittoor, Jaishree; Deeba, Farah; Deikman, Jill; Deng, Molian; Duff, Stephen;
Fabbri, Bradon; Fenner, Jason; Fernandes, Mary; Gabbert, Karen; Galligan, Megan; Goldman, Barry; Hawkins, Debbie; Heard,
Jacqueline; Karunanandaa, Bala; Ke, Dangyang; Ledeaux, John; Lee, Gary; Madappa, Savitha; Nelson, Donald; Patty, Obed; Qi,
Qungang; Rajani, M. S.; Ramachandra, Dhanalakshmi; Ramamohan, G.; Ruff, Thomas; Sanders, Rick; Sangeetha, S.; Savage,
Thomas J.; Savidge, Beth; Shobha, Char; Sudarshana, Padmini; Suma, S. Navarathna; Sun, Jindong; Thompson, Rebecca; Val, Dale;
Venkatachalayya, Srikanth; Venkatesh, T.; Vidya, Kr; Wu, Jingrui; Xie, Zhidong; Xu, Nanfei; Zheng, Wei. (Monsanto Technology, LLC,
USA). PCT Int. Appl. (2008), 115pp. CODEN: PIXXD2 WO 2008021543 A2 20080221 Designated States W: AE, AG, AL, AM,
AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD,
GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG,
MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM,
TN, TR, TT, TZ. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, MT, NL, PT, SE, TR, BF,
BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2007-US18368 20070817. Priority:
US 2006-838415 20060817. CAN 148:231469 AN 2008:219158 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
flavanone

WO 2008021543 A2 20080221 WO 2007-US18368 20070817
US 20080000405 A1 20080103 US 2007-765562 20070620
US 2006-838415P P 20060817
US 2006-816086P P 20060623
Abstract
This invention provides transgenic plant cells with recombinant DNA for expression of proteins that are useful for imparting enhanced
agronomic trait(s) to transgenic crop plants. This invention also provides transgenic plants and progeny seed comprising the transgenic
plant cells where the plants are selected for having an enhanced trait selected from the group of traits consisting of enhanced water
use efficiency, enhanced cold tolerance, increased yield, enhanced nitrogen use efficiency, enhanced seed protein, and enhanced
seed oil. Three hundred fifty-eight polynucleotides and their encoded protein sequences are provided from corn, soybean cotton,
canola, alfalfa, rice, and wheat. An addnl. 28,615 homolog sequences are identified by screening public and proprietary databases.
Also disclosed are methods for manufg. transgenic seed and plants with enhanced traits.
Answer 48:
Transepithelial transport of flavanone in intestinal Caco-2 cell monolayers. Kobayashi, Shoko; Konishi, Yutaka. Department
of Food and Life-Science, Takasaki University of Health and Welfare, 37-1, Nakaorui, Takasaki, Gumma, Japan. Biochemical and
Biophysical Research Communications (2008), 368(1), 23-29. Publisher: Elsevier, CODEN: BBRCA9 ISSN: 0006-291X. Journal
written in English. CAN 148:369236 AN 2008:205370 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
Our recent study [S. Kobayashi, S. Tanabe, M. Sugiyama, Y. Konishi, Transepithelial transport of hesperetin and hesperidin in intestinal
Caco-2 cell monolayers, Biochim. Biophys. Acta, 1778 (2008) 33-41] shows that the mechanism of absorption of hesperetin involves
both proton-coupled active transport and transcellular passive diffusion. Here, as well as analyzing the cell permeability of hesperetin,
we also study the transport of other flavanones, naringenin and eriodictyol, using Caco-2 cell monolayers. Similar to hesperetin
mentioned, naringenin and eriodictyol showed proton-coupled polarized transport in apical-to-basolateral direction in non-saturable
manner, const. permeation in the apical-to-basolateral direction (Jap → bl) irresp. of the transepithelial elec. resistance (TER), and
preferable distribution into the basolateral side after apical loading in the presence of a proton gradient. Furthermore, the
proton-coupled Jap → bl of hesperetin, naringenin and eriodictyol, were inhibited by substrates of the monocarboxylic acid transporter
(MCT), such as benzoic acid, but not by ferulic acid. In contrast, both benzoic and ferulic acids have no stimulatory effect on Jap →
flavanone
bl of each flavanone by trans-stimulation anal. These results indicates that proton-driven active transport is commonly participated in
the absorption of flavanone in general, and that its transport is presumed to be unique other than MCT-mediated transport for
absorption of phenolic acids (PAs), sodium-dependent MCT (SMCT) nor anion exchanger-mediated transport.
Answer 49:
Suppressive effects of flavonoid fisetin on lipopolysaccharide-induced microglial activation and neurotoxicity. Zheng,
Long Tai; Ock, Jiyeon; Kwon, Byoung-Mog; Suk, Kyoungho. Department of Pharmacology, School of Medicine, Brain Science and
Engineering Institute, CMRI, Kyungpook National University, Taegu, S. Korea. International Immunopharmacology (2008), 8(3),
484-494. Publisher: Elsevier B.V., CODEN: IINMBA ISSN: 1567-5769. Journal written in English. CAN 148:322913 AN
Abstract
Microglia are innate immune cells in the central nervous system. Activation of microglia plays an important role in the processes of
several neurodegenerative diseases including Alzheimer's disease, Parkinson's disease, and HIV dementia. Activated microglia can
produce various proinflammatory cytokines and nitric oxide (NO), which may exert neurotoxic effects. Inhibition of microglia
activation may alleviate neurodegeneration under these conditions. To search for the novel therapeutic agents against
neuroinflammatory diseases, we have screened a series of flavonoid compds. using a cell-based assay. Our studies showed that
fisetin markedly suppressed the prodn. of tumor necrosis factor (TNF)-α, NO, and prostaglandin (PG) E2 in lipopolysaccharide
(LPS)-stimulated BV-2 microglia cells or primary microglia cultures. Fisetin also inhibited the gene expression of TNF-α, interleukin
(IL)-1β, cyclooxygenase (COX-2) and inducible nitric oxide synthase (iNOS) at both mRNA and protein levels. Fisetin significantly
suppressed IκB degrdn., nuclear translocation of NF-κB, and phosphorylation of p38 mitogen-activated protein kinase (MAPKs) in the
LPS-stimulated BV-2 microglia cells. In addn., fisetin reduced cytotoxicity of LPS-stimulated microglia toward B35 neuroblastoma cells
in a co-culture system. These results indicate that fisetin has a strong anti-inflammatory activity in brain microglia, and could be a
potential therapeutic agent for the treatment of neuroinflammatory diseases.
Answer 50:
Ultrafiltration as alternative purification procedure for the characterization of low and high molecular-mass phenolics from
almond skins. Prodanov, Marin; Garrido, Ignacio; Vacas, Visitacion; Lebron-Aguilar, Rosa; Duenas, Montserrat; Gomez-Cordoves,
Carmen; Bartolome, Begona. Departamento de Agroalimentacion, IMIDRA, Madrid, Alcala de Henares, Spain. Analytica Chimica
Acta (2008), 609(2), 241-251. Publisher: Elsevier B.V., CODEN: ACACAM ISSN: 0003-2670. Journal written in English. CAN
148:425231 AN 2008:198764 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
A combination of sample prepn. (ultrafiltration) and anal. techniques is proposed for the characterization of complex phenolic mixts.
such as exts. from almond (Prunus dulcis (Mill.) D.A. Webb) skins. LC/ESI-MS anal. of the permeates obtained after ultrafiltration on
semipermeable membranes (low mol.-mass phenolic fractions) allowed the identification of several benzoic acids and aldehydes,
flavan-3-ol monomers and oligomers, and flavonol and flavanone glycosides in almond skins. MALDI-TOF and ESI-MS/MS anal. of the
diafiltered concs. (high mol.-mass phenolic fractions) demonstrated the presence of proanthocyanidin oligomers up to decamers,
composed of (epi)afzelechin, (epi)catechin and (epi)gallocatechin units linked by C-C bonds (type B) and by both C-C and C-O bonds
(type A). This anal. protocol can be of utility in the study of low and high mol.-mass phenolic compds. in natural products.
Answer 51:
flavanone
Anti-inflammatory effects of flavonoids: genistein, kaempferol, quercetin, and daidzein inhibit STAT-1 and Nf-κB activations,
whereas flavone, isorhamnetin, naringenin, and pelargonidin inhibit only Nf-κB activation along with their inhibitory effect
on iNOS expression and NO production in activated macrophages. Hamalainen, Mari; Nieminen, Riina; Vuorela, Pia; Heinonen,
Marina; Moilanen, Eeva. The Immunopharmacology Research Group Medical School and Tampere University Hospital, Research
Unit, University of Tampere, Tampere, Finland. Mediators of Inflammation (2007), No pp. given. Publisher: Hindawi Publishing
Corp., CODEN: MNFLEF ISSN: 0962-9351. http://www.hindawi.com/GetArticle.aspx?doi=10.1155/2007/45673 Journal; Online
Computer File written in English. AN 2008:194620 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
In inflammation, bacterial products and proinflammatory cytokines induce the formation of large amts. of nitric oxide (NO) by inducible
nitric oxide synthase (iNOS), and compds. that inhibit NO prodn. have anti-inflammatory effects. In the present study, we
systematically investigated the effects of 36 naturally occurring flavonoids and related compds. on NO prodn. in macrophages
exposed to an inflammatory stimulus (lipopolysaccharide, LPS), and evaluated the mechanisms of action of the effective compds.
Flavone, the isoflavones daidzein and genistein, the flavonols isorhamnetin, kaempferol and quercetin, the flavanone naringenin, and
the anthocyanin pelargonidin inhibited iNOS protein and mRNA expression and also NO prodn. in a dose-dependent manner. All eight
active compds. inhibited the activation of nuclear factor-κB (NF-κB), which is a significant transcription factor for iNOS. Genistein,
kaempferol, quercetin, and daidzein also inhibited the activation of the signal transducer and activator of transcription 1 (STAT-1),
another important transcription factor for iNOS. The present study characterises the effects and mechanisms of naturally occurring
phenolic compds. on iNOS expression and NO prodn. in activated macrophages. The results partially explain the pharmacol. efficacy
of flavonoids as anti-inflammatory compds.
Answer 52:
New 7,8-benzoflavanones as potent aromatase inhibitors: Synthesis and biological evaluation. Yahiaoui, Samir; Fagnere,
Catherine; Pouget, Christelle; Buxeraud, Jacques; Chulia, Albert-Jose. Faculte de Pharmacie, UPRES EA 4021 "Biomolecules et
Therapies anti-tumorales", Limoges, Fr. Bioorganic & Medicinal Chemistry (2008), 16(3), 1474-1480. Publisher: Elsevier Ltd.,
CODEN: BMECEP ISSN: 0968-0896. Journal written in English. CAN 148:440250 AN 2008:181307 CAPLUS (Copyright (C)
Abstract
Some natural compds. such as flavonoids are known to possess a moderate inhibitory activity against aromatase, this enzyme being
an interesting target for hormone-dependent breast cancer treatment. It has been demonstrated that the modulation of flavonoid
skeleton could increase anti-aromatase effect. Therefore, new 7,8-benzoflavanones were synthesized and tested for their activity
toward aromatase inhibition. It was obsd. that the introduction of a benzo ring at position C-7 and C-8 on flavanone skeleton led to new
potent aromatase inhibitors, the resulting 7,8-benzoflavanones being until nine times more potent than aminogluthetimide (the first
aromatase inhibitor used clin.).
Answer 53:
Short and mid-term bioavailability of flavanones from oranges in humans. De Pascual-Teresa, S.; Sanchez-Moreno, C.;
Granado, F.; Olmedilla, B.; De Ancos, B.; Cano, M. P. Instituto del Frio, CSIC, Madrid, Spain. Current Topics in Nutraceutical
Research (2007), 5(2/3), 129-134. Publisher: New Century Health Publishers, LLC, CODEN: CTNRC3 ISSN: 1540-7535. Journal
written in English CAN 148:307212 AN 2008:178004 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
flavanone
Abstract
Flavanones are a group of flavonoids characteristic of citrus fruits that have been assocd. with hypocholesterolemic and antioxidative
effects. Flavanones from oranges, mainly hesperetin and naringenin, have also been proved to be effective in the inhibition of chem.
induced carcinogenesis in animal models. Although there are some studies regarding the bioavailability of flavanones from orange
juice or pure compds., the levels of hesperetin and naringenin that may be reached in plasma after the consumption of oranges in a
normal diet in humans is largely unknown. The purpose of this study was to investigate the effects of single and repeated intakes of a
normal amt. of orange flavanones on hesperidin and naringin plasma concns. and antioxidant activity in humans. After ingestion of
400 g of minimally processed orange fruit the levels of plasma hesperetin increased gradually throughout the study period. The max.
level of hesperetin reached in plasma was 148 nmol/L, whereas for naringenin the max. level was only 15 nmol/L. Plasma FRAP
decreased slightly during the study, however this decrease was not significant. In the multiple-dose-response study the results
showed a significant increase over the baseline levels of hesperetin in plasma after 7 and 14 days of daily ingestion of 200 g orange,
thus indicating that the effect obtained after a single-dose ingestion is not predictive of the effect after a multiple-dose regimen.
Answer 54:
New anti-emetic flavanone glycoside from cotoneaster affinis. Jangwan, J. S.; Tiwari, M. P. Department of Chemistry,
H.N.B.Garhwal University, Tehri, India. Natural Products (2007), 3(3), 187-189. Publisher: Trade Science Inc., CODEN:
NPAREX Journal written in English. AN 2008:169269 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
The present paper deals with the isolation Characterization of a new compd. along with Genkwanin and Kaempferol from the sapwood
and anti-ematic activity detn. of 1. From the methanolic ext., genkwanin, kampferol, naringenin and a new derivs. 1 were isolated.
The structure of the known compds. were detd. by spectroscopic methods and by direct comparision (m.m.p., co-TLC, Superimposible
IR) with authentic samples. The new compd. 1 was purified by acetylated and characterized with the help of NMR and MS datas.
Answer 55:
Macroporous resin adsorption of the flavanone from the effluent in pomelo peel processing. Li, Wei; Zhong, ShiAn; Qiao,
Rong; Yuan, ZhouLv; Du, JianPing. Department of Chemistry and Chemical Engineering, Central South University, Changsha
Hunan, Peop. Rep. China. Beijing Huagong Daxue Xuebao, Ziran Kexueban (2007), 34(Suppl. 2), 28-31. Publisher: Beijing
Huagong Daxue Xuebao, Ziran Kexueban Bianji Weiyuanhui, CODEN: BHDXAA ISSN: 1671-4628. Journal written in Chinese. AN
Abstract
Naringin was recovered from the effluent from the industrial processing of pomelo peel using extn. by acid, permeation through a
membrane, and chromatog. with a macroporous resin. The adsorption characteristics on the resin of the soln. permeated through the
membrane were found by HPLC to be identical to those of a direct alc. ext. of the effluent. Permeation of the soln. through the
membrane, however, allowed the AB-8 macroporous resin to be reused at least 6 times without loss of performance. Usage of the
resin in the treatment of the effluent is therefore viable in an industrial plant.
Answer 56:
flavanone
A pyranochalcone and prenylflavanones from Tephrosia pulcherrima (Baker) Drumm. Ganapaty, Seru; Srilakshmi, Guttula V.
K.; Pannakal, Steve T.; Laatsch, Hartmut. Pharmacognosy and Phytochemistry Division, College of Pharmaceutical Sciences,
Andhra University, Visakhapatnam, India. Natural Product Communications (2008), 3(1), 49-52. Publisher: Natural Product Inc.,
CODEN: NPCACO ISSN: 1934-578X. Journal written in English. CAN 148:466904 AN 2008:164991 CAPLUS (Copyright (C)
Abstract
A new 2',6'-dimethoxy-4',5'-(2'',2''-dimethyl)-pyranochalcone (1) and three known flavanones, namely

5-hydroxy-7-methoxy-8-(3,3-dimethylallyl)-flavanone (Me glabranin) (2), 5,7-dimethoxy-8-(3,3-dimethylallyl)-flavanone (candinone) (3)
and 5-O-Me obovatin (pongachin) (4), have been isolated from the chloroform ext. of the roots of Tephrosia pulcherrima. The
flavonoids were fully characterized by detailed 1D- and 2D-NMR spectroscopic investigations. The pyranochalcone 1 showed
significant antimicrobial activity when tested against a series of microorganisms.
Answer 57:
Cloning and sequence analysis of flavonoid biosynthesis genes in Brassica juncea. Yan, Ming-li; Liu, Zhong-song; Guan,
Chun-yun; Chen, She-yuan; Liu, Xian-jun; Yuan, Mou-zhi. Rapeseed Research Institute, Hunan Agricultural University, Changsha,
Peop. Rep. China. Zhongguo Nongye Kexue (Beijing, China) (2007), 40(12), 2688-2695. Publisher: Zhongguo Nongye Kexue
Bianjibu, CODEN: CKNYAR ISSN: 0578-1752. Journal written in Chinese. AN 2008:163113 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
[Objective] The objective of this study is to isolate and clone the genes of flavonoid biosynthesis in Brassica juncea. [Method]
Homol.-based cloning strategy was used in this study. The primers were designed according to the sequences of homologous genes
of the model plant Arabidopsis thaliana. The gene fragments were sequenced, and analyzed by BLAST. [Result] Seventeen gene
copies were obtained by using 13 pairs of specific primers. These copies were shown to be homologous to 13 known Arabidopsis
thaliana functional genes. The gene CHS (chalcone synthase) has three copies, while the genes PAP (prodn. of anthocyanin pigment)
and CHI (chalcone isomerase) each has two copies. No data was found in GenBank about the DNA binding/transcription factor genes
(TT2, TT8, TTG2, PAP) and flavanone 3-hydroxylase (TT6) gene of Brassica through BLAST anal. [Conclusion] The cloned copies of
genes for flavonoid biosynthesis will provide further information on genetic regulation of seed coat color formation in Brassica juncea.
Answer 58:
Two new bioactive prenylated dihydroflavanoids from the medicinal plant Dolichos tenuicaulis (Baker) Craib. Peng,
Jin-Yong; Dong, Fu-Qiu; Liu, Ke-Xin; Han, Xu; Xu, You-Wei; Qi, Yan; Xu, Qi-Wei; Xu, Li-Na. School of Pharmacy, Dalian Medical
University, Dalian, Peop. Rep. China. Journal of Asian Natural Products Research (2008), 10(2), 169-175. Publisher: Taylor &
Francis Ltd., CODEN: JANRFI ISSN: 1028-6020. Journal written in English. AN 2008:148330 CAPLUS (Copyright (C) 2008
Abstract
Two new prenylated dihydroflavanoids have been isolated from the medicinal plant of Dolichos tenuicaulis (Baker) Craib. Their
structures were elucidated as
(2S)-5,2',6'-trihydroxy-8-prenyl-6,7-(3-prenyl-2,2-dimethylpyrano)-3',4'-(2,2-dimethyl-1-keone-cyclohexadiene)-flavanone (1) and
flavanone
(2S)-5,2',6'-trihydroxy-8-prenyl-6,7-(3-prenyl-2,2-dimethyl-1-keone-cyclohexadiene)-flavanone (2) on the basis of spectroscopic anal.
Answer 59:
Mitochondrial toxicity and antioxidant activity of a prenylated flavonoid isolated from Dalea elegans. Elingold, Igal;
Isollabella, M. Paula; Casanova, Marta B.; Celentano, Ana M.; Perez, Cristina; Cabrera, Jose Luis; Diez, Roberto A.; Dubin, Marta.
Facultad de Medicina, Centro de Estudios Farmacologicos y Botanicos (CEFYBO), UBA-CONICET, Buenos Aires, Argent.
Chemico-Biological Interactions (2008), 171(3), 294-305. Publisher: Elsevier Ireland Ltd., CODEN: CBINA8 ISSN: 0009-2797.
Abstract
The prenylated flavanone 2'-4'-dihidroxy-5'-(1'''-dimethylallyl)-6-prenylpinocembrin) (6PP), isolated from the roots of Dalea elegans,
shows antimicrobial activity. The aim of this study was to evaluate mitochondrial toxicity and antioxidant properties of 6PP. Addn. of
micromolar concns. of 6PP to rat liver mitochondria, stimulated O2 uptake in state 4 and inhibited it in state 3 when malate-glutamate
was the respiratory substrate, and inhibited O2 uptake in state 3 when succinate was the substrate. Highest concn. of 6PP also
inhibited O2 uptake in state 4 in the latter case; in both conditions, respiratory control index values were decreased. This flavanone
collapsed the mitochondrial membrane potential in a concn.-dependent manner. 6PP also inhibited F0F1-ATPase activity in coupled
mitochondria and in submitochondrial particles. In the latter, this compd. also inhibited NADH oxidase and succinate dehydrogenase
activities. HEp-2 cells were incubated for 24 h with 6PP in presence or absence of 0.5% albumin. As measured by redn. of the
mitochondrial-related probe MTT, in the albumin-free condition, 6PP was cytotoxic in a concn.-dependent manner; on the other hand,
albumin decreased 6PP effect. In addn., in rat liver microsomes 6PP: (1) inhibited the enzymic lipid peroxidn., (2) exhibited significant
scavenging activity, measured by DPPH redn. assay and (3) demonstrated significant antioxidant activity by decreasing the redn. of
Mo(VI) to Mo(V). We suggest that 6PP impairs the hepatic energy metab. by acting as mitochondrial uncoupler and by inhibiting
enzymic activities linked to the respiratory chain. 6PP also exerts both antioxidant and antiradical activities. Due to its cytotoxicity,
this mol., and its future structure developments, can be considered as a potentially promising therapeutic agent, for instance in cancer
chemotherapy.
Answer 60:
Minerals, phenolic compounds, and antioxidant capacity of citrus peel extract by hot water. Xu, G. H.; Chen, J. C.; Liu, D.
H.; Zhang, Y. H.; Jiang, P.; Ye, X. Q. Dept. of Food Science and Nutrition, Zhejiang Univ., Hangzhou, Peop. Rep. China.
Journal of Food Science (2008), 73(1), C11-C18. Publisher: Blackwell Publishing, Inc., CODEN: JFDSAZ ISSN: 0022-1147.
Journal written in English. CAN 148:190787 AN 2008:131463 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
Some dried citrus peels, more familiar as chenpi in China, have been widely used in traditional Chinese medicines from ancient times.
This paper reports the efficiency of infusion cooking on extg. minerals and phenolic compds. (flavanone glycosides [FGs],
polymethoxylated flavones [PMFs], and phenolic acids), and also antioxidant activity of hot water ext. of citrus peels. Peels of 2
citrus varieties, namely, Satsuma mandarin (C. unshiu Marc.) and Ponkan (C. poonensis Hort. ex Tanaka), which belong to C.
reticulata, were selected. As a result, hot water extn. was efficient in extg. phenolic acids and some minerals. As for citrus
flavonoids, narirutin, nobiletin, and tangeretin were easier to ext. than hesperidin. The result of antioxidant capacity assays indicated
that for citrus peels, hot water ext. had almost the same capacity as the methanol ext. We suggested that Ponkan was more suitable
as the source of chenpi, since its hot water ext. had much higher content of phenolic acids, FGs and PMFs, and higher antioxidant
capacity than those of Satsuma mandarin. Generally, to raise the extn. temp. or to prolong the time could not yield higher content of
phenolic compds. and stronger antioxidant capacity, though the content of minerals increased to some extent. Furthermore, a
flavanone
2nd-time extn. seemed necessary since considerable minerals and phenolic compds. could be obtained by doing so. Finally, we
suggested that 2 times extn. at 100 °C for 30 min was proper to ext. the minerals and phenolic compds. in chenpi.
Answer 61:
Inhibition of LPS-induced iNOS, COX-2 and cytokines expression by poncirin through the NF-κB inactivation in RAW 264.7
macrophage cells. Kim, Jong-Bin; Han, Ah-Reum; Park, Eun-Young; Kim, Ji-Yeon; Cho, Woong; Lee, Jun; Seo, Eun-Kyoung; Lee,
Kyung-Tae. Department of Pharmaceutical Biochemistry, College of Pharmacy, Kyung-Hee University, Seoul, S. Korea.
Biological & Pharmaceutical Bulletin (2007), 30(12), 2345-2351. Publisher: Pharmaceutical Society of Japan, CODEN: BPBLEO
ISSN: 0918-6158. Journal written in English. CAN 148:276403 AN 2008:128576 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
We previously reported that poncirin, a flavanone glycoside isolated from the EtOAc ext. of the dried immature fruits of Poncirus
trifoliata, is an anti-inflammatory compd. that inhibits PGE2 and IL-6 prodn. The present work was undertaken to investigate the mol.
actions of poncirin in RAW 264.7 macrophage cell line. Poncirin reduced lipopolysaccharide (LPS)-induced protein levels of inducible
nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) and the mRNA expressions of iNOS, COX-2, tumor necrosis factor-α
(TNF-α) and interleukin-6 (IL-6) in a concn.-dependent manner, as detd. by Western blotting and RT-PCR, resp. Furthermore, poncirin
inhibited the LPS-induced DNA binding activity of nuclear factor-κB (NF-κB). Moreover, this effect was accompanied by a parallel
redn. in IκB-α degrdn. and phosphorylation that in by nuclear translocations of p50 and p65 NF-κB subunits. Taken together, our data
indicate that anti-inflammatory properties of poncirin might be the result from the inhibition iNOS, COX-2, TNF-α and IL-6 expression
via the down-regulation of NF-κB binding activity.
Answer 62:
Flavanone O-glycosides from the rhizomes of Dryopteris sublaeta. Feng, Weisheng; Cao, Xinwei; Kuang, Haixue; Zheng,
Xiaoke. Henan College of Traditional Chinese Medicine, Zhengzhou, Peop. Rep. China. Yaoxue Xuebao (2007), 42(8), 867-871.
Publisher: Yaoxue Xuebao Bianjibu, CODEN: YHHPAL ISSN: 0513-4870. Journal written in English. AN 2008:120022 CAPLUS
Abstract
The aim of this study was to look for the chem. constituents from the rhizomes of Dryopteris sublaeta. The fresh plant was extd.
twice with boiling water, and the ext. was concd. to small vol. under reduced pressure at 50°C. The concd. material was partitioned with
ether, Et acetate and n-butanol. The fraction of Et acetate was repeatedly chromatographed over silica gel and Sephadex LH-20
columns. Structures of pure compds. were established on the basis of their physicochem. and spectral data. Nine compds. were
obtained and identified as sublaetentin A (1), sublaetentin B (2), sublaetentin C (3), sublaetentin D (4), matteuorienate A, matteuorienate
C (6), arbutin (7), 3-methoxy-4-hydroxyphenyl-1-O-β-D- glucopyranoside (8) and 3, 4-dimethoxyphenyl-1-O-β-D-glucopyranoside (9).
Compds. 1-4 are new compds., and the others were isolated from this plant for the 1st time.
Answer 63:
A guaianolide sesquiterpene, a chromenone, and a flavanone from Ligularia macrophylla. Wang, Qi; Chen, Daofeng.
flavanone
Department of Pharmacognosy, School of Pharmacy, Fudan University, Shanghai, Peop. Rep. China. Helvetica Chimica Acta
(2007), 90(12), 2432-2437. Publisher: Verlag Helvetica Chimica Acta, CODEN: HCACAV ISSN: 0018-019X. Journal written in
English. CAN 148:163658 AN 2008:117980 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
Three new compds., (5β,9β)-guaia-6,10(14)-dien-9-ol

(=rel-(1R,3aS,5R,8aR)-1,2,3,3a,4,5,6,8a-octahydro-1-methyl-4-methylene-7-(1-methylethyl)azulen-5-ol; 1),
6-acetyl-8-methoxy-2,3-dimethyl-chromen-4-one (=6-acetyl-8-methoxy-2,3-dimethyl-4H-1-benzopyran-4-one; 2), and
(2S)-3'-hydroxy-5',7-dimethoxyflavanone (=(2S)-2,3-dihydro-2-(3-hydroxy-5-methoxyphenyl)-7-methoxy-4H-1-benzopyran-4-one; 3)
were isolated from the roots and rhizomes of Ligularia macrophylla, together with seven known compds. Their structures and
configurations were elucidated by spectroscopic methods, including 2D-NMR techniques.
Answer 64:
Biological activities of the chemical constituents of Erythrina stricta and Erythrina subumbrans. Rukachaisirikul, Thitima;
Saekee, Amporn; Tharibun, Chatchana; Watkuolham, Sudarut; Suksamrarn, Apichart. Department of Chemistry, Faculty of Science,
Ramkhamhaeng University, Bangkok, Thailand. Archives of Pharmacal Research (2007), 30(11), 1398-1403. Publisher:
Pharmaceutical Society of Korea, CODEN: APHRDQ ISSN: 0253-6269. Journal written in English. CAN 148:163654 AN
Abstract
Phytochem. investigation of the hexane and CH2CI2 exts. of Erythrina stricta roots and E. subumbrans stems led to the isolation of
six pterocarpans, one flavanone, one isoflavone, two alkaloids, five triterpenes, six steroids and alkyl trans-ferulates. The structures
of all known compds. were detd. on the basis of spectroscopic evidence. Sophoradiol (15), a mixt. of stigmast-4-en-3-one (19) and
stigmasta-4,22-dien-3-one (20), lupeol (21), cycloeucalenol (22), a mixt. of 3β-hydroxystigmast-5-en-7-one (23) and
3β-hydroxystigmast-5,22-dien-7-one (24) and melilotigenin C (25) were first isolated from the genus Erythrina. The isolated compds.
were evaluated for antiplasmodial activity, antimycobacterial activity and cytotoxicity. Among the tested compds.,
5-hydroxysophoranone (8) exhibited the highest antiplasmodial activity against Plasmodium falciparum (IC50 2.5 μg/mL). Compd. 8,
erystagallin A (5), erycristagallin (7) and erysubin F (10) showed the same level of antimycobacterial activity against Mycobacterium
tuberculosis (MIC 12.5 μg/mL). For cytotoxicity, erybraedin A (2) showed the highest activity against the NCI-H187 and BC cells
(IC50 2.1 and 2.9 μg/mL, resp.), whereas 10 exhibited the highest activity against the KB cells (IC50 4.5 μg/mL).
Answer 65:
Nematicidal prenylated flavanones from Phyllanthus niruri. Shakil, N. A.; Pankaj; Kumar, J.; Pandey, R. K.; Saxena, D. B.
Division of Agricultural Chemicals, Indian Agricultural Research Institute, New Delhi, India. Phytochemistry (Elsevier) (2008),
69(3), 759-764. Publisher: Elsevier Ltd., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 148:303519 AN
Abstract
Two prenylated flavanones have been isolated from the hexane ext. of Phyllanthus niruri plant. The structure of these flavanones
were established as 8-(3-Methyl-but-2-enyl)-2-Ph chroman-4-one (I) and 2-(4-hydroxyphenyl)-8-(3-methyl-but-2-enyl)-chroman-4-one (II)
on the basis of spectral anal. These were evaluated for nematicidal activity against root-knot, Meloidogyne incognita, and reniform,
flavanone
Rotylenchulus reniformis, nematodes. Compd. 2 exhibited nematicidal activity at par with the std. carbofuran (LC50 3.3 and 3.1 ppm,
resp.) when tested against reniform nematode. The LC50 value against root-knot nematode was found to be 14.5 ppm. Compd. 1
however, showed moderate activity against both the test nematodes.
Me Me
I R=H
O II R=OH
Answer 66:
Naringenin reduces tumor size and weight lost in N-methyl-N'-nitro-N-nitrosoguanidine-induced gastric carcinogenesis in
rats. Ekambaram, Ganapathy; Rajendran, Peramaiyan; Magesh, Venkataraman; Sakthisekaran, Dhanapal. Department of Medical
Biochemistry, Dr A.L. Mudaliyar Postgraduate Institute of Basic Medical Sciences, University of Madras, Chennai, India. Nutrition
Research (New York, NY, United States) (2008), 28(2), 106-112. Publisher: Elsevier Inc., CODEN: NTRSDC ISSN: 0271-5317.
Abstract
Carcinoma of the stomach is reportedly the second most common cancerous condition affecting the general population.
Administration of antioxidants is reported to effectively alleviate the risk of gastric carcinoma. Therefore, we assessed the protective
role of naringenin, an antioxidant and naturally occurring citrus flavanone, on gastric carcinogenesis induced by MNNG (200mg/kg
body wt.) and S-NaCl (1 mL per rat) in Wistar rats (obtained from the Central Animal House Facility, University of Madras, Taramani
Campus, Chennai, India). The animals were divided into 5 groups, and the effects of naringenin on simultaneous and posttreated
stages of MNNG were tested. Cancer risk was analyzed along with their antioxidant status. The LPO levels in the exptl. groups were
assessed as an index of oxidative milieu. Altered redox status was subsequently investigated by assaying the superoxide and
hydroxyl radicals, the enzymic antioxidants (SOD, CAT, GPx), and the nonenzymic antioxidants viz reduced GSH, vitamin C, and
vitamin E. In the presence of MNNG, cancer incidence and LPO levels were significantly increased, whereas enzymic (SOD, CAT,
and GPx) and nonenzymic antioxidant activities (GSH, Vitamins C, and E) were decreased in the treated rats compared with control
rats. Administration of naringenin to gastric carcinoma-induced rats largely up-regulated the redox status to decrease the risk of
cancer. We conclude that up-regulation of antioxidants by naringenin treatment might be responsible for the anticancer effect in
gastric carcinoma.
Answer 67:
Natural ingredients used in cosmeceuticals. Dweck, Anthony C. Dweck Data, Salisbury, Wiltshire, UK. Editor(s): Walters,
Kenneth A.; Roberts, Michael S. Dermatologic, Cosmeceutic, and Cosmetic Development (2008), 303-323. Publisher: Informa
Healthcare, New York, N. Y CODEN: 69KKCH Conference; General Review written in English. AN 2008:107398 CAPLUS
flavanone
Abstract
The sources of data for products that may have topical cosmeceutical benefit were presented. The different chem. compds. present
in plants were also discussed, specifically fatty acids, flavanoids, chalcones, flavones, flavanone glycoside, aurones, flavonols,
isoflavones, phytosterols and related compds. and sugars, polysaccharides, and mucopolysaccharides. Various plants that are
considered to be specialist plants because of their unique chem. entities were also conferred.
Answer 68:
Flavonoid glycosides and limonoids from Citrus molasses. Kuroyanagi, Masanori; Ishii, Hiromi; Kawahara, Nobuo; Sugimoto,
Hiroyuki; Yamada, Hideo; Okihara, Kiyoshi; Shirota, Osamu. Faculty of Life and Environmental Sciences, Prefectural University of
Hiroshima, Shobara, Hiroshima, Japan. Journal of Natural Medicines (2008), 62(1), 107-111. Publisher: Springer Japan, CODEN:
JNMOBN Journal written in English. CAN 148:444846 AN 2008:104357 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
Molasses of tangerine orange (Citrus unshiu Markovich) is obtained as a waste product in the course of tangerine orange juice prodn.
This molasses is expected to be a useful source of org. compds. such as flavonoids and limonoids. To elucidate a use for this
molasses waste, we isolated and identified its org. constituents. Two new flavanonol glycosides were isolated from tangerine orange
molasses, along with several flavonoids such as hesperidine, narirutin, eriodictyol,
3',4',5,6,7,8-hexamethoxy-3-O-β-D-glucopyranosyloxyflavone, and 3',4',5,6,7,8-hexamethoxy-
3-β-D-[4-O-(3-hydroxy-3-methylglutaloyl)]-glucopyranosyloxyflavone, and limonoids such as limonin, nomilin, and cyclic peptide,
citrusin III. The structures of the new flavanonol glycosides were detd. as
(2R,3R)-7-O-(6-O-α-L-rahmnopyranosyl-β-D-glucopyranosyl)-aromadendrin and 7-O-(6-O-α-
L-rahmnopyranosyl-β-D-glucopyranosyl)-3,3',5,7-tetrahydroxy-4'-methoxyflavanone by means of spectral analyses using 1H-NMR,
13C-NMR, and 2D-NMR. Of these compds., flavanone glycoside, hesperidin and narirutin were isolated as the main constituents.
Thus, molasses is a promising source of flavonoid glycosides.
Answer 69:
Extraction and identification of total flavanone from papaya leaves by ultrasonic wave. Huang, Suoyi; Liu, Haihua; Li, Haini;
Tang, Yulian; Zhang, Jingxuan. Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Guangxi Province,
SGGHAL ISSN: 1008-0805. Journal written in Chinese. CAN 148:433472 AN 2008:103407 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Flavonoids were extd. by ethanol as the solvent from papaya leaves with ultrasonic wave and ethanol extn. Using spectrophotometry
to ext. and check the flavanone of papaya leaves. The d. of the total flavanone of papaya leaves was C = 0.9880 mg/mL and the
rate of recovery was 97.79%. This method was a purely phys. process and had not any pollution. It was an ideal way to ext. the
flavanone from papaya leaves.
Answer 70:
flavanone
Supercritical carbon dioxide extraction of essential oil from propolis of Mount Meng and analysis by GC-MS. Li, Yajie;
Ling, Jianya; Deng, Yong. School of Life Science, Shandong University, Jinan, Shandong Province, Peop. Rep. China. Shizhen
Guoyi Guoyao (2006), 17(10), 1975-1976. Publisher: Shizhen Guoyi Guoyao Bianweihui, CODEN: SGGHAL ISSN: 1008-0805.
Journal written in Chinese. CAN 148:433467 AN 2008:103168 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
After supercrit. fluid extn. (SFE), the volatile oil was sepd. by GC-MS and detd. by normalization method. Forty-four components from
propoils by SFE were sepd. and identified, representing 93.12% of the total area. The main compds. of volatile oil were
9,12-octadecadienoic acid 23.91%, hexacosane 12.92%, nonacosane 7.44%, hexadecanoic acid 6.65%, tetracosane 5.23%,
octadecadienoic acid, Me ester 4.58%, 9-Octadecenoic acid 3.94%, ergostero 3.90%, heneicosane 3.42% etc. Supercrit. extn. was not
widely used yet, there would be more and more viewpoints that could justify it, as simple and convenient, high purity, residual solvent
content.
Answer 71:
Antioxidantive effectiveness of Trichosanthes kirilowii maximowicz extracts. Zhoh, Choon Koo; Uhm, Tae Yong; Kim, Joo
Chan. Department of Chemical+Environmental Engineering, Soongsil University, Seoul, S. Korea. Kongop Hwahak (2007),
18(6), 625-629. Publisher: Korean Society of Industrial and Engineering Chemistry, CODEN: KOHWE9 ISSN: 1225-0112. Journal
written in Korean. AN 2008:98447 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
Recently, there is a growing interest about unsatd. lecithin having excellent characteristics of skin affinity and absorbency.
Accordingly, this study intended to develop a natural sulfuration material in order to enhance the stability of oxidn. of unsatd. lecithin
and substitute existing sulfuration materials which indicate variability and toxicity. As sulfuration components, plenol acid family,
3,5-dihydroxybenzoic acid, and flavanone were analyzed. Total polyphenol content was higher in the root exts. (133.85 mg/g) than in
the fruit exts. (53.5 mg/g). Above 100 ppm polyphenol content, the free radical removal efficiency and lipid oxidn. prevention of the
root exts. were 20.1 and 19.2% superior compared with BHT resp. Also, the exts. indicated high survival rate of more than 95% below
1250 ppm, showing the stability. For the stability of liposome made from an unsatd. lecithin, the root exts. were superior to the fruit
exts. Esp., 15.1 and 13.9% of sulfuration effect and zeta potential were improved with 9.3% reduced particle size compared with BHT
as the control group, resp.
Answer 72:
Plant phenolics regulate neoplastic cell growth and survival: a quantitative structure-activity and biochemical analysis.
Harris, Cory S.; Mo, Fan; Migahed, Lamiaa; Chepelev, Leonid; Haddad, Pierre S.; Wright, James S.; Willmore, William G.; Arnason,
John T.; Bennett, Steffany A. L. Neural Regeneration Laboratory and Ottawa Institute of Systems Biology, Department of
Biochemistry, Microbiology, and Immunology, University of Ottawa, Ottawa, ON, Can. Canadian Journal of Physiology and
Pharmacology (2007), 85(11), 1124-1138. Publisher: National Research Council of Canada, CODEN: CJPPA3 ISSN: 0008-4212.
Abstract
The anti-tumor activities of many plant phenolics at high concns. (>100 μmol/L) suggest their potential use as dietary supplements in
cancer chemoprevention and cancer chemotherapy. However, it is not clear what impact phenolic compds. have at the physiol.
flavanone
concns. obtained through consumption of high phenolic diets on neoplastic cells. In the present study, 54 naturally occurring phenolics
were evaluated at physiol. relevant concns. for their capacity to alter PC12 cell viability in response to serum deprivation, the
chemotherapeutic agent etoposide, and the apoptogen C2-ceramide. Surprisingly, novel mitogenic, cytoprotective, and antiapoptotic
activities were detected. Quant. structure-activity relationship modeling indicated that many of these activities could be predicted by
compd. lipophilicity, steric bulk, and (or) antioxidant capacity, with the exception of inhibition of ceramide-induced apoptosis. Where
quant. structure-activity relationship anal. was insufficient, biochem. assessment demonstrated that the benzoate orsellinic acid
blocked downstream caspase-12 activation following ceramide challenge. These findings demonstrate substantive mitogenic,
cytoprotective, and antiapoptotic biol. activities of plant phenolics on neoplastic cells at physiol. relevant dietary concns. that should
be considered in chemopreventive and chemotherapeutic strategies.
Answer 73:
Synthesis and bactericidal activity of 5,7-dihydroxy-flavanone. Li, Jianfen; Chen, Hongmei. Department of Chemical and
Environmental Engineering, Wuhan Polytechnic University, Wuhan, Peop. Rep. China. Nongyao (2006), 45(11), 733-734, 736.
Publisher: Nongyao Bianjibu, CODEN: NONGFP ISSN: 1006-0413. Journal written in Chinese. AN 2008:80189 CAPLUS
Abstract
5,7-Dihydroxy-flavanone was synthesized with cinnamic acid from benzaldehyde, whose yield amounted to 91%. Its structure was
characterized and confirmed by IR, MS and 1H NMR. Meanwhile, bactericidal tests had been carried out, and the results of preliminary
biol. test indicated that the compd. had excellent bactericidal activities against Escherichia coli, Bacillus subtilis, Staphylococcus
aureus. The inhibition rate againsted Escherichia coli, Bacillus subtilis amounted to 100% at the dosage of 50 μg/mL.
Answer 74:
Distinct Effects of Naringenin and Hesperetin on Nitric Oxide Production from Endothelial Cells. Liu, Li; Xu, Dong-mei;
Cheng, Yi-yu. College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, Peop. Rep. China. Journal of Agricultural
and Food Chemistry (2008), 56(3), 824-829. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal
Abstract
Diets rich in citrus and citrus-based products have been neg. correlated with the risk of cardiovascular disease, but so far no studies
have been conducted to det. whether naringenin and hesperetin, two major flavanones in citrus plants, influence endothelium nitric
oxide (NO) prodn. The aim of this study is to clarify estrogenic activities of naringenin and hesperetin and to examine whether they
affect endothelial NO prodn. via estrogen receptor (ER) activation. Both naringenin and hesperetin were obsd. to promote growth of
MCF-7 cells under greatly reduced estrogen conditions and to suppress estrogen-induced response. Naringenin activated both ERα
and ERβ, whereas hesperetin exhibited stronger potential to activate ERα rather than ERβ. Hesperetin, but not naringenin, increased
NO releases from human umbilical vein endothelial cells in a dose-dependent manner. Hesperetin-induce responses were suppressed
by ICI 182 780 and actinomycin D. Real-time reverse transcription polymerase chain reaction (RT-PCR) and western-blotting anal.
revealed that hesperetin up-regulated endothelium nitric oxide synthase (eNOS) expression. These results suggested that hesperetin
exerts an antiatherogenic effect, in part, via ER-mediated eNOS expression and subsequent increase of endothelial NO prodn.
Distinct effects of naringenin and hesperetin on NO prodn. also imply that ERα might play the major role in estrogen-induced eNOS
expression. However, the inefficacy of naringenin on NO prodn. remains to be elaborately studied. Our findings add more proof to
the mol. explanations for the health benefits of citrus used to prevent cardiovascular disease, esp. for postmenopausal women.
Answer 75:
flavanone
Antioxidant activity of seed ethanol extracts of different buckwheat cultivars. He, Yongyan; Feng, Baili; Gao, Jinfeng; Pang,
Ming; Chai, Yan. College of Agronomy, Northwest A+F University, Yangling, Shaanxi, Peop. Rep. China. Editor(s): Chai, Yan;
Zhang, Zongwen. Advances in Buckwheat Research, Proceedings of the International Symposium on Buckwheat, 10th, Yangling,
China, Aug. 14-18, 2007 (2007), 567-575. Publisher: Northwest A&F University Press, Yangling, Peop. Rep. China CODEN:
69KILK Conference written in English. CAN 148:448353 AN 2008:66141 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
Total antioxidant capacities and phenolic contents of ethanol exts. of common and tartary buckwheat seeds were examd. Total
antioxidant properties of exts. were assessed by FRAP assays, total phenolic contents measured by Folin-Ciocalteu assay, and
flavonoids contents measured by NaNO2-Al(NO)3. The result indicated that there were differences in total antioxidant capacities, total
phenolic and flavonoids contents of ethanol exts. of seeds for different cultivars. While differences in FRAP value of buckwheat
flour for different cultivars and common buckwheat hull for different cultivars was not remarkable. The total phenolic content of
tartary buckwheat flour was approx. two times higher than that of common buckwheat flour. In contrast, total phenolic content of
common buckwheat hull was higher than that of tartary buckwheat hull. Total flavonoids content of tartary buckwheat flour was higher
than that of common buckwheat flour but the difference was limited. Total flavonoids content of common buckwheat hull was higher
than that of tartary buckwheat hull and the difference was significant. All exts. exhibited good antioxidant activity. Compared with
common buckwheat, tartary buckwheat exhibited stronger antioxidant activity.
Answer 76:
Development of oxidation resisting tartary buckwheat wine. Li, Yunlong; Fang, Shan; Bian, Junsheng; Li, Hongmei; Hu, Junjun;
Di, Jianbing; He, Zhiyong; Lin, Rufa. Institute of Comprehensive Utilization of Agricultural Products, Shanxi Academy of Agricultural
Science, Taiyuan, Peop. Rep. China. Editor(s): Chai, Yan; Zhang, Zongwen. Advances in Buckwheat Research, Proceedings of
the International Symposium on Buckwheat, 10th, Yangling, China, Aug. 14-18, 2007 (2007), 422-426. Publisher: Northwest A&F
University Press, Yangling, Peop. Rep. China CODEN: 69KILK Conference written in English. AN 2008:66119 CAPLUS
Abstract
This study on the flavanone material extn. and purifn. which obtains to the tartary buckwheat liquor distiller's grain, then strengthen 38°
& 53° buckwheat liquor, its DPPH free radical clearance percentage and total oxidn. resistance ability enhance sep. 90.35%, 31.69
U/mL and 85.64%, 24.92 U/mL, the effect is extremely remarkable. This strengthening process is good to the liquor feeling in the
mouth reveals mellowly. But not to the liquor quality extremely affects.
Answer 77:
Study on extracting processing of the total flavanone of melon by ultrasonic wave. Pang, Hong; Wen, Lue; Wang, Xiao-ping;
Li, Lin; Huang, Suo-yi. Department of Chemistry, Guangxi Medicine School, Nanning, Guangxi, Peop. Rep. China. Weiliang
Yuansu Yu Jiankang Yanjiu (2007), 24(6), 49-50. Publisher: Weiliang Yuansu Yu Jiankang Yanjiu Zazhishe, CODEN: WYYJAF
ISSN: 1005-5320. Journal written in Chinese. CAN 148:448161 AN 2008:63238 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
flavanone
Abstract
In order to make use of the resources of bitter melon, avoid wasting and approach the extn. of total flavanone of bitter melon. The
flavonoids were extd. by ethanol as the solvent from bitter melon with ultrasonic wave and ethanol extn. Using spectrophotometry to
ext. and check the flavanone of bitter melon. By this method getting the contents of the total flavanone of bitter melon is C = 6.72%
and the rate of recovery is 101.0%. This text provides the extn. and purifying methods to get the outcome and the purity of the
flavanone are all very high. This method is a purely phys. process, and has not any pollution. It is an ideal way to ext. the flavanone
of bitter melon.
Answer 78:
Neuroprotective Effects of the Citrus Flavanones against H2O2-Induced Cytotoxicity in PC12 Cells. Hwang, Sam-Long; Yen,
Gow-Chin. Department of Food Science and Biotechnology, National Chung Hsing University, Taichung, Taiwan. Journal of
Agricultural and Food Chemistry (2008), 56(3), 859-864. Publisher: American Chemical Society, CODEN: JAFCAU ISSN:
Abstract
The citrus flavanones hesperidin, hesperetin, and neohesperidin are known to exhibit antioxidant activities and could traverse the
blood-brain barrier. H2O2 formation induces cellular oxidative stress assocd. with neurodegenerative diseases. In this study,
protective effects of pretreatments (6 h) with hesperidin, hesperetin, and neohesperidin (0.8, 4, 20, and 50 μM) on H2O2-induced (400
μM, 16 h) neurotoxicity in PC12 cells were evaluated. The results showed that hesperetin, hesperidin, and neohesperidin, at all test
concns., significantly (p < 0.05) inhibited the decrease of cell viability (MTT redn.), prevented membrane damage (LDH release),
scavenged ROS formation, increased catalase activity, and attenuated the elevation of intracellular free Ca2+, the decrease of
mitochondrial membrane potential (except those of 0.8 μM neohesperidin-treated cells) and the increase of caspase-3 activity in
H2O2-induced PC12 cells. Meanwhile, hesperidin and hesperetin attenuated decreases of glutathione peroxidase and glutathione
reductase activities and decreased DNA damage in H2O2-induced PC12 cells. These results first demonstrate that the citrus
flavanones hesperidin, hesperetin, and neohesperidin, even at physiol. concns., have neuroprotective effects against H2O2-induced
cytotoxicity in PC12 cells. These dietary antioxidants are potential candidates for use in the intervention for neurodegenerative
diseases.
Answer 79:
Extracting of total flavanone from flocculu's banyan silk and its effects on scavenging of hydroxyl radicals. Huang, Suoyi;
Li, Haini; Tang, Yulian; Liu, Haihua. Youjiang Nationality Medical College, Baise, Guangxi Province, Peop. Rep. China. Huagong
Shengchan Yu Jishu (2006), 13(4), 16-18. Publisher: Huagong Shengchan Yu Jishu Bianjibu, CODEN: HSYJAC ISSN: 1006-6829.
Abstract
Extg. of total flavanone from flocculu's banyan silk was made, the extd. flavone was validated, and UV spectrophotometry was used
to det. its content. Mass concn. of total flavone in the detd. sample was 1.151 mg/mL, recovery was 99.36% with high purity and
yield. The extd. liq. was detd. to have scavenging on hydroxyl radicals. Scavenging capacity on hydroxyl radicals increased as the
extd. liq. increases.
Answer 80:
flavanone
Determination of flavanones and flavanonols in Blumea balsamifera DC. by RP-HPLC. Huang, Yong-lin; Wen, Yong-xin;
Zhao, Zhi-guo; Zhu, Ting-chun. Guangxi Institute of Botany, Guilin, Guangxi, Peop. Rep. China. Guangxi Kexue (2007), 14(2),
140-142. Publisher: Guangxi Kexue Bianjibu, CODEN: GKUEAC ISSN: 1005-9164. Journal written in Chinese. CAN 148:339228
Abstract
A method for the detn. of flavanones and flavanonols in Blumea balsanifera DC. by HPLC was established. The following HPLC
conditions gave the best results: column: ZORBAX XDB-C18 (4.6 mm × 150 mm, 5 μm); mobile phase:V (methanol):V (water) = 60:40;
flow rate: 0.8 mL/min; detection wavelength: 290 nm; temp.: 30°. Linearity was obtained within the range of 0.0032 μg/μl and 0.048
μg/μl (r = 0.9999 resp.) for flavanones. Linearity for flavanonols was obtained within the range of 0.0032 μg/μl and 0.048 μg/μl (r =
0.9993 resp.). The RSD of flavanones and flavanonols were 1.08% and 1.26% resp. (n = 5); av. recoveries were 98.36% and 97.86%,
resp. (n = 5).
Answer 81:
Asymmetric cyclization of 2'-hydroxychalcones to flavanones: catalysis by chiral Broensted acids and bases. Dittmer,
Claudia; Raabe, Gerhard; Hintermann, Lukas. Institute of Organic Chemistry, RWTH Aachen University, Aachen, Germany.
European Journal of Organic Chemistry (2007), (35), 5886-5898. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN:
EJOCFK ISSN: 1434-193X. Journal written in English. CAN 148:284927 AN 2008:45142 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
The asym. cyclization of 2'-hydroxychalcones to flavanones is a basic, enzyme-catalyzed step in the biosynthesis of flavonoid
natural products, but poses a long-standing problem for asym. catalysis with small mol. catalysts. Earlier claims concerning the
realization of an asym. flavanone synthesis by means of camphorsulfonic acid as chiral Broensted acid catalysts were reinvestigated
using accurate HPLC methods for quantification of enantiomer ratios. The previous claims of asym. induction were thus shown to be
untenable. On the other hand, cinchona alkaloids serve as chiral Bronsted base mediators for the asym. cyclization of either
6'-substituted 2'-hydroxychalcones or 2',6'-dihydroxychalcones. 2',6'-Dihydroxy-4,4'-dimethoxychalcone, for instance, cyclized to give
the naturally occurring naringenin-4',7-dimethyl ether in up to 64% ee at 81% conversion. The catalysis shows a marked dependency
of the enantiomeric excess of the product on the catalyst, solvent and reactant concn. Based on these successful examples of
asym. cyclizations of 2'-hydroxychalcones to flavanones, requirements for more active asym. catalysts can be defined.
Answer 82:
High level antioxidant-containing plants expressing a transcription factor involved in flavonoid pathway. Rommens,
Caius. (J.R. Simplot Company, USA). PCT Int. Appl. (2008), 67pp. CODEN: PIXXD2 WO 2008005474 A2 20080110
Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM,
DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK,
LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD,
SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS,
IT, LU, MC, MT, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application:
flavanone
WO 2007-US15437 20070705. Priority: US 2006-818516 20060706. CAN 148:137081 AN 2008:43584 CAPLUS (Copyright (C)

WO 2008005474 A2 20080110 WO 2007-US15437 20070705
WO 2008005474 A3 20080417
GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM, AP, EA,
EP, OA
US 2006-818516P P 20060706
Abstract
The present invention relates to increasing at least one antioxidant level in a plant or plant product by expressing a polynucleotide that
encodes a transcription factor, which is active in a flavonoid pathway. Over-expression of, for instance, a novel and newly-identified
chlorogenic acid-inducing gene Cai, in a plant results in increased accumulation of chlorogenic acid and other related phenolics, which,
in turn, increases the levels of beneficial antioxidant in the plant. Furthermore, the present invention boosts antioxidant levels by
inhibiting the expression of at least one of the flavanone-3',5'-hydroxylase (F35h) gene, a flavanone-3'-hydroxylase (F3h), a
dihydroflavonol reductase (Dfr) gene, and a chalcone isomerase (Chi) gene, in addn. to over-expression of the Cai gene.
Answer 83:
Two new promelacacinidin dimers, including a novel flavanone-flavanol dimer characterized by a unique C(3)-C(4) linkage,
from the heartwood of Acacia nigrescens. Howell, H.; Malan, E.; Brand, D. J.; Kamara, B. I.; Bezuidenhoudt, B. C. B.; Marais,
C.; Steenkamp, J. A. Department of Chemistry, University of the Free State, Bloemfontein, S. Afr. Chemistry of Natural
Compounds (2007), 43(5), 533-538. Publisher: Springer, CODEN: CHNCA8 ISSN: 0009-3130. Journal written in English. CAN
Abstract
Two new promelacacinidin biflavonoids, mesquitol-(4α,5)-epimesquitol-4β-ol (I) and a

3',4',7,8-tetrahydroxyflavanone(3,4)-ent-epimesquitol (II), were isolated among others from the heartwood of Acacia nigrescens. The
flavanone derived dimer, characterized by a unique C(3) to C(4) bridge, which links the monomers via two stereogenic and sp3
hybridized C-atoms, is the prototype of a new subgroup of the flavonoid family. Assessment of the abs. configuration of all five
stereogenic centers of this novel flavanone-derived biflavonoid was achieved by correlating the chiroptical properties of the benzoyl
chromophore to the abs. configuration of C(2) of the flavanone moiety and hence the abs. stereochem. of the other four chiral
flavanone
centers.
OH
OH
HO
HO O
OH
OH
HO
O OH
OH
HO
OH I
OH
OH
HO
HO O
O H OH
HO
O OH
HO
HO II
Answer 84:
Anticancer drug composition containing cancer cell-killing compound. Bae, Yeong Seok; Noh, Yun Hwa; Lee, Byeong Won;
Park, Gi Hun. (Kyungpook National University, Office of Research Support, S. Korea). Repub. Korea (2007), 13pp. CODEN:
KRXXFC KR 784628 B1 20071212 Patent written in Korean. Application: KR 2006-86623 20060908. Priority: . CAN 148:299861
flavanone

KR 784628 B1 20071212 KR 2006-86623 20060908
KR 2006-86623 20060908
Abstract
The title anticancer drug compn. contains cancer cell-killing compd.,

2',5,7-trihydroxy-4',5'-(2,2-dimethylchromeno)-8-(3-hydroxy-3-methylbuthyl)flavanone. The compd. can kill cells of lung cancer,
non-small-cell lung cancer, skin cancer, neck cancer, melanoma in skin or eyeball, crissal cancer, uterus cancer, oviduct cancer,
cervical cancer, vagina cancer, vulva cancer, Hodgkin's disease, esophagus cancer, ductless gland cancer, thyroid cancer,
parathyroid cancer, adrenal gland cancer, soft tissue sarcoma, urethral carcinoma, penile cancer, prostate cancer, chronic or acute
leukemia, lymphocytic lymphoma, bladder cancer, ureter cancer, pelvis cancer, central nervous system tumor, primary central
nervous system lymphoma, vertebra tumor, and brain stem gliomas by inhibiting the activity of topoisomerase I of mammals.
Answer 85:
High-performance liquid chromatographic evaluation of a coated cellulose tris(3,5-dimethylphenylcarbamate) chiral

stationary phase having a small-pore silica support. Liu, Yueqi; Zou, Hanfa. National Chromatographic Research and
Analysis Center, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Peop. Rep. China. Journal of
Chromatography, A (2008), 1178(1-2), 118-125. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in
Abstract
A two-step coating/pptn. synthetic procedure has been developed for the prepn. of cellulose tris(3,5-dimethylphenylcarbamate) chiral
stationary phase (CSP) having a small-pore silica support. With this synthetic strategy, monodisperse, spherical CSP particles can be
produced without the need for a wasteful and time-consuming sieving process. The performance of the synthesized CSP towards a
variety of racemates was evaluated in the normal-phase HPLC mode. HPLC sepn. expts. revealed that the synthesized CSP
exhibited a chiral recognition ability fully comparable to the corresponding com. columns prepd. using conventional large-pore silica as
the support. Moreover, the synthesized CSP was successfully applied to semipreparative enantiosepn. of a new triazole antifungal
agent.
Answer 86:
Extraction of total flavanone from Herba Artemisiae Scopariae by microwave and ultrasonic assistant. Li, Zhi-ping; Yin,
Du-lin; Li, You-ji; Zhang, Zhao-hui; Huang, Peng-fei. College of Chemistry and Chemical Engineering, Hunan Normal University,
Changsha, Peop. Rep. China. Hunan Chengshi Xueyuan Xuebao, Ziran Kexueban (2007), 16(3), 56-58. Publisher: Hunan
Chengshi Xueyuan Xuebao Bianjibu, CODEN: HCXZAB ISSN: 1672-7304. Journal written in Chinese. CAN 148:409885 AN
flavanone
Abstract
The total flavonoids in Herba Artemisiae Scopariae was extd. by microwave assisted or ultrasonic assisted extn. using 70% ethanol as
extg. solvent. The influences of extg. time, rate of material to liq., microwave power or ultrasonic power on extg. rate were
investigated and the technol. conditions were optimized by orthogonal. The results show that the optimal extg. conditions for ultrasonic
assisted extn. are as follows: extg. time, temp., rate of material to liq. and ultrasonic power are 60min, 60°C, 5:125(g:mL) and 200 W;
resp., for extn. with microwave assistant, the optimal conditions are 24 min of extg. time, 350 W of microwave power, the rate of
material to liq. being 5:125 (g:mL). The extg. rate with 3.29% by ultrasonic assisted extn. is little more than that of microwave assisted
extn. with 3.09%.
Answer 87:
Efficient synthesis of polyoxygenated flavones from naturally occurring flavanones. Bovicelli, Paolo; D'Angelo, Vittoria;
Collalto, Daniela; Verzina, Antonio; D'Antona, Nicola; Lambusta, Daniela. C.N.R. Instituto di Chimica Biomolecolare, Sezione di
Roma, Universita di Roma 'La Sapienza', Rome, Italy. Journal of Pharmacy and Pharmacology (2008), Volume Date 2007,
59(12), 1697-1701. Publisher: Pharmaceutical Press, CODEN: JPPMAB ISSN: 0022-3573. Journal written in English. CAN
Abstract
Flavonoids are constituents of the human diet (they are present in many beverages and food), and in organisms they are responsible
for several biol. functions, including that of antioxidant. Because of the increasing interest in these mols., methods for their synthesis
and structural modification are of great importance; studies on the biol. activities of many of these compds. are insufficient because
of their scarcity and/or high cost. We have developed an expeditious synthesis of polyoxygenated flavones, starting from available
and inexpensive flavanones, using a bromination-methoxylation procedure. A series of flavonoids that are not otherwise accessible
can be prepd. using this method. As an example, 3'-demethoxysudachitin (I), a limited flavone possessing antimicrobial activity
against methicillin-resistant Staphylococcus aureus and Helicobacter pylori and acting as a 2,2-diphenyl-1-picrylhydrazyl (DPPH)
scavenger, was prepd. in fairly satisfactory yield.
OH
OMe
HO O
MeO
OH O I
Answer 88:
Applicability of t-flavanone to treat female pattern baldness. Sasajima, Michiyo; Moriwaki, Shigeru; Hotta, Mitsuyuki; Kitahara,
Takashi; Takema, Yoshinori. Kao Corporation, Tochigi, Japan. Cosmetics & Toiletries (2007), 122(12), 77-78, 80, 82-84.
Publisher: Allured Publishing Corp., CODEN: CTOIDG ISSN: 0361-4387. Journal; General Review written in English. CAN
flavanone
Abstract
A review. T-Flavanone, trans-3, 4'-dimethyl-3-hydroxyflavanone, promotes the growth of hair follicles and increases hair diam. It has
been established for the treatment of male pattern baldness. This study examines its application to treat female pattern baldness.
Answer 89:
Nitric Oxide Production Inhibitory Activity of Flavonoids Contained in Trunk Exudates of Dalbergia sissoo. Shrestha, Suraj
Prakash; Amano, Yuri; Narukawa, Yuji; Takeda, Tadahiro. Kyoritsu University of Pharmacy, 1-5-30 Shibakoen, Minato-ku, Tokyo,
Japan. Journal of Natural Products (2008), 71(1), 98-101. Publisher: American Chemical Society-American Society of
Pharmacognosy, CODEN: JNPRDF ISSN: 0163-3864. Journal written in English. CAN 148:139569 AN 2007:1474811
Abstract
Methanolic exts. of trunk exudates of Dalbergia sissoo yielded two new open-chain neoflavonoids (1, 2), a new flavonoid (3), a new
flavanone (4), and 26 known compds. Their structures were elucidated by detailed spectroscopic analyses. The ability of the isolated
compds. to prevent nitric oxide (NO) prodn. by LPS-stimulated J774.1 cells was also studied. All of the isolated compds. except 4,
formononetin, and zenognosin B exhibited significant activity in a concn.-dependent manner. Compds. 2 and 3 were among the most
potent NO prodn. inhibitors, with IC50 values of 3.19 and 6.22 μM, resp., and compd. 1 had an IC50 of 31.6 μM.
Answer 90:
Studies on the chemical constituents of Caulis Spatholobi. Han, Liping. Dept. of Clinical Pharmacy, The No.2 People's
Hospital of Datong in Shanxi Province, Datong, Peop. Rep. China. Zhongguo Yaofang (2006), 17(20), 1596-1598. Publisher:
Zhongguo Yaofang Zazhishe, CODEN: ZYHAA4 ISSN: 1001-0408. Journal written in Chinese. AN 2007:1457657 CAPLUS
Abstract
OBJECTIVE: To study the chem. constituents of caulis spatholobi. METHODS: The constituents of caulis spatholobi were sepd. and
purified with varied chromatog. techniques, and the structures were identified based on spectral data and chem. properties. RESULTS:
8 compds. were isolated from spatholobi. They were identified as spatholobus suberectus dunn (Compd. 1), formonoetis (Compd. 2),
daidzein (Compd. 3), calycosin (Compd. 4), pyromucicacid (Compd. 5), 1, 3, 5-trihydroxybenzene (Compd. 6), succinic acid (Compd.
7) and β-sitosterol (Compd. 8). CONCLUSION: Spatholobus suberectus dunn is a new compd. and characterized as 7, 3',
4'-trihydoxy-6-methoxy flavanone. Compds. 4, 5, 6 and were obtained from caulis spatholobi for first time.
Answer 91:
Stabilization of low-soluble cosmetic ingredients using microcapsule made of polymer/polyols. Lee, Dong-Hwan; Kim,
Jin-Hui; Lee, Bum-Chun; Pyo, Hyeong-Bae. (Han-Bul Cosmetics Co., Ltd., S. Korea). PCT Int. Appl. (2007), 44pp. CODEN:
PIXXD2 WO 2007145395 A1 20071221 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA,
CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG,
flavanone
KM, KN, KP, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL,
PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN. Designated States RW: AT,
BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD,
TG. Patent written in English. Application: WO 2006-KR3149 20060811. Priority: KR 5302-5 20060613. CAN 148:85129 AN

WO 2007145395 A1 20071221 WO 2006-KR3149 20060811
W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK,
DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN,
KP, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ,
OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG,
US, UZ, VC, VN, ZA, ZM, ZW
RW: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LT, LU, LV, MC, NL, PL, PT,
RO, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG, BW, GH,
KR 781604 B1 20071203 KR 2006-53025 20060613
KR 2006-53025 A 20060613
Abstract
The present invention relates to a method of stabilizing active ingredients that have low soly. using hollow-type, multi-layered
microcapsules made of hydrophobic polymer/polyhydric alc., a method prepg. the hollow-type, multilayered microcapsules, and a
cosmetic compn. contg. the microcapsules. Thus, encapsulation of quercetin in poly(Me methacrylate) hollow-type, multilayered
microcapsules contg. glycerin, butylene glycol and diethylene glycol monoethyl ether (5:4:1) was exemplified.
Answer 92:
Enzymic preparation of water soluble phenolic glucosides with dermocosmetic and therapeutic applications. Auriol,
Daniel; Nalin, Renaud; Robe, Patrick; Lefevre, Fabrice. (Libragen, Fr.). Eur. Pat. Appl. (2007), 58pp. CODEN: EPXXDW EP
1867729 A1 20071219 Designated States R: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LI, LT, LU,
LV, MC, NL, PL, PT, RO, SE, SI, SK, TR, AL, BA, HR, MK, YU. Patent written in English. Application: EP 2006-290972 20060614.
Priority: . CAN 148:53217 AN 2007:1448622 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))

EP 1867729 A1 20071219 EP 2006-290972 20060614
R: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LI, LT, LU, LV, MC, NL, PL,
PT, RO, SE, SI, SK, TR, AL, BA, HR, MK, YU
WO 2007144368 A2 20071221 WO 2007-EP55815 20070613
flavanone
KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA,
NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN,
TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW
EP 2006-290972 A 20060614
Abstract
The invention relates to the prepn. of phenolics derivs. by enzymic condensation of phenolics selected among pyrocatechol or its
derivs. including (i) protocatechuic acid and its derivs., (ii) 3,4-dihydroxycinnamic acid with its trans-isomer or caffeic acid and its
derivs., esp. hydrocaffeic acid, rosmarinic acid, chlorogenic acid and caffeic acid phenethyl ester, and with its cis-isomer and its
derivs., esp. esculin, (iii) dihydroxyphenylglycol, and (iv) members of the flavonoid family such as taxifolin and fustin
(dihydroflavonols), fisetin (a flavonol), eriodictyol (a flavanone), , with the glucose moiety of sucrose. The prodn. of said phenolics
derivs. is achieved with a glucosyltransferase (EC 2.4.1.5) obtained from a culture of Leuconostoc species, and more particularly from
the culture of Leuconostoc mesenteroides NRRL B-512F. These O-glucosides of selected phenolics are new, have a soly. in water
higher than that of their parent polyphenol and have useful applications in cosmetic and pharmaceutical compns., such as
antioxidative, antiviral, antibacterial, immune-stimulating, anti-allergic, antihypertensive, anti-ischemic, anti-arrhytmic, antithrombotic,
hypocholesterolemic, anti-lipoperoxidant, hepatoprotective, anti-inflammatory, anticarcinogenic antimutagenic, antineoplastic,
anti-thrombotic, and vasodilatory formulations, or in any other field of application. All the more, glucosylated phenolics derivs. objects
of the invention can be hydrolyzed by the human natural microbiotes, thus releasing the active part of the phenolic compd. upon time
during their usage or by an α-glucosidase (EC 3.2.1.20).
Answer 93:
2'-Hydroxyflavylium: introducing flavanones into the flavylium network of chemical reactions. Petrov, Vesselin; Gomes,
Raquel; Parola, A. Jorge; Jesus, Alexandre; Laia, Cesar A. T.; Pina, Fernando. REQUIMTE, Departamento de Quimica, Faculdade de
Ciencias e Tecnologia, Universidade Nova de Lisboa, Caparica, Port. Tetrahedron (2007), Volume Date 2008, 64(4), 714-720.
Publisher: Elsevier Ltd., CODEN: TETRAB ISSN: 0040-4020. Journal written in English. CAN 148:238903 AN 2007:1434603
Abstract
Chalcones possessing a hydroxyl group in position 2 cyclize to form flavylium salts in acidic media, this reaction being reversible
under neutral-basic conditions. On the other hand, chalcones possessing a hydroxyl group in position 2' cyclize to form flavanones in
basic media. By synthesizing 2'-hydroxyflavylium tetrafluoroborate (I), it was possible to obtain trans-2,2'-dihydroxychalcone (II) that
in soln. can evolve to 2'-hydroxyflavanone or back to 2'-hydroxyflavylium depending on the pH. The several equil. established in aq.
soln. were fully characterized. The importance of including flavanones into the flavylium network of chem. reactions is briefly
exploited.
flavanone
HO
HO
OH
+
O
BF 4 - I O II
Answer 94:
Study on the effects of the extracts from some Alpinia and Zingiber species (Zingiberaceae) of Vietnam of the blood
peroxidase activity. Phan, Minh Giang; Le, Huyen Tram; Phan, Tong Son. College of Natural Science, Vietnam National Univ.,
Ha Noi, Vietnam. Tap Chi Duoc Hoc (2007), 47(9), 8-11. Publisher: Bo Y Te Xuat Ban, CODEN: TCDHDQ ISSN: 0258-6967.
Journal written in Vietnamese. AN 2007:1429149 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
The preventive antioxidant effect of the exts. of some Zingiberaceae species including Alpinia gagnepainii K. Schum., A. malaccensis
(Burm. f.) Roscoe, A. conchigera Griff., A. globosa (Lour.) Horan., and Zingiber rubens Roxb. was demonstrated in term of increases
in the activity of the endogenous peroxidase of blood group O by the H2O2-induced oxidn. assay. The Alpinia flavonoids
(-)-pinocembrin and chalconaringenin 2'-O-Me ether of flavanone and chalcone structure, resp., also showed indirect antioxidant activity
via peroxidase.
Answer 95:
Flavonone-C-glycosides from the seeds of Zizyphus jujuba Mill var. spinosa Hu. Trinh, Thi Thuy; Tran, Van Sung; Franke, K.;
Arnold, N.; Wessjohann, L. Institute of Chemistry, Vietnamese Academy of Science and Technology, Vietnam. Tap Chi Hoa Hoc
(2007), 45(4), 496-501. Publisher: Toa Soan Tap Chi Hoa Hoc, CODEN: TCHHDC ISSN: 0378-2336. Journal written in English.
Abstract
From the seeds of Zizyphus jujuba, five flavone-C-glycosides, isovitexin-2"-O-β-D-glucopyranoside, spinosin, and spinosin A-C have
been isolated. Their structures were elucidated by spectroscopic methods and comparison with reported data.
Answer 96:
Characterization of uridine-diphosphate dependent flavonoid glucosyltransferase from Oryza sativa. Hong, Byoung Seok;
Kim, Jeong Ho; Kim, Na Yeon; Kim, Bong-Gyu; Chong, Youhoon; Ahn, Joong-Hoon. Department of Bioscience and Biotechnology,
Bio/Molecular Informatics Center, Konkuk University, Seoul, S. Korea. Journal of Biochemistry and Molecular Biology (2007),
flavanone
40(6), 870-874. Publisher: Korean Society for Biochemistry and Molecular Biology, CODEN: JBMBE5 ISSN: 1225-8687. Journal
Abstract
We cloned a uridine-diphosphate dependent glycosyltransferase RUGT-10 from Oryza sativa. The recombinant enzyme was
expressed by glutathione-S transferase gene fusion system in Escherichia coli. RUGT10 showed different regioselectivity depending
on the structures of substrates (e.g. flavanone, flavonol, and flavone). Apparently, flavanone such as naringenin and eriodictyol gave
one 7-O-glucoside while flavone and flavonol gave more than two products with preferential glucosylation position of hydroxyl group at
C-3 position.
Answer 97:
Activation of pro-survival Akt and ERK1/2 signalling pathways underlie the anti-apoptotic effects of flavanones in cortical
neurons. Vauzour, David; Vafeiadou, Katerina; Rice-Evans, Catherine; Williams, Robert J.; Spencer, Jeremy P. E. Molecular
Nutrition Group, School of Chemistry, Food and Pharmacy, University of Reading, Reading, UK. Journal of Neurochemistry
(2007), 103(4), 1355-1367. Publisher: Blackwell Publishing Ltd., CODEN: JONRA9 ISSN: 0022-3042. Journal written in English.
Abstract
There is growing interest in the potential beneficial effects of flavonoids in the aging and diseased brain. We have investigated the
potential of the flavanone hesperetin and two of its metabolites, hesperetin-7-O-β-D-glucuronide and 5-nitro-hesperetin, to inhibit
oxidative stress-induced neuronal apoptosis. Exposure of cortical neurons to hydrogen peroxide led to the activation of apoptosis
signal-regulating kinase 1 via its de-phosphorylation at Ser963, the phosphorylation of c-jun N-terminal kinase and c-Jun (Ser73) and
the activation of caspase 3 and caspase 9. While hesperetin glucuronide failed to exert protection, both hesperetin and
5-nitro-hesperetin were effective at preventing neuronal apoptosis via a mechanism involving the activation/phosphorylation of both
Akt/protein kinase B and extracellular signal-regulated kinase 1 and 2 (ERK1/2). Protection against oxidative injury and the activation
of Akt and ERK1/2 followed a bell-shaped response and was most apparent at 100 nmol/L concns. The activation of ERK1/2 and Akt
by flavanones led to the inhibition of the pro-apoptotic proteins, apoptosis signal-regulating kinase 1, by phosphorylation at Ser83 and
Bad, by phosphorylation at both Ser136 and Ser112 and to the inhibition of peroxide-induced caspase 9 and caspase 3 activation.
Thus, flavanones may protect neurons against oxidative insults via the modulation of neuronal apoptotic machinery.
Answer 98:
Isoflavonoids in nonleguminous taxa: A rarity or a rule? Lapcik, Oldrich. Department of Chemistry of Natural Compounds,
Faculty of Food and Biochemical Technology, Institute of Chemical Technology in Prague, Prague, Czech Rep. Phytochemistry
(Elsevier) (2007), 68(22-24), 2909-2916. Publisher: Elsevier Ltd., CODEN: PYTCAS ISSN: 0031-9422. Journal; General Review
Abstract
A review. Isoflavonoids are characteristic metabolites in legumes and an overwhelming no. of reports concerning them come from the
Leguminosae. Nevertheless, the spectrum of isoflavonoid producing taxa includes the representatives of four classes of multicellular
plants, namely the Bryopsida, the Pinopsida, the Magnoliopsida and the Liliopsida. At least 59 nonleguminous families have been
reported to produce isoflavones sensu lato; coumestans have been reported in 3 families, coumaronochromones in 3, pterocarpans in
flavanone
9 and rotenoids in 8 families. Prenylated isoflavones have been found in 15 non-leguminous families and isoflavone dimers,
heterodimers or oligomers in three families. More than 200 different isoflavonoid aglycons have been reported in non-legumes
altogether. The no. of individual structures is even greater if the variety of glycosides are considered. Enzymol. and genetics of
isoflavonoid biosynthesis have been studied almost exclusively in legumes, with the exception of a few model plants (i.e. Beta
vulgaris, Arabidopsis thaliana, Nicotiana tabacum and Zea mays). The key step at the very beginning of the isoflavonoid metabolic
pathway is the oxidn. of flavanone connected with the migration of aryl moiety from C2 to C3 mediated by a CYP450 enzyme
isoflavone synthase (IFS), which has been identified and cloned in multiple legumes and in sugar beet (Beta vulgaris,
Chenopodiaceae). No information is available about the enzyme(s) responsible for the biosynthesis of isoflavonoid core in other taxa.
Exptl. data demonstrates the capability of numerous enzymes of non-legume origin to metabolize isoflavones as alternative substrates
to other phenolics.
Answer 99:
Inhibitory activity of compounds isolated from Polymnia sonchifolia on aflatoxin production by Aspergillus flavus. Park,
Adriana; Goncalez, Edlayne; Felicio, Joana D'arc; Pinto, Marina Mori; Rossi, Maria Helena; Simoni, Isabela Cristina; Lopes, Marcia
Nassser. Instituto de Quimica, Universidade Estadual Paulista, Araraquara, SP, Brazil. Brazilian Journal of Microbiology (2007),
37(2), 199-203. Publisher: Brazilian Society of Microbiology, CODEN: BJMRAH ISSN: 1517-8382. Journal; Computer Optical Disk
Abstract
Polymnia sonchifolia, commonly known as "yacon", was originally cultivated at Andes mountains in South America. Recently, the
specie attracted worldwide attention because of its wide range of uses, for example in the control of diabetes melitus, besides the
antifungal and pesticidal compds. were found in the leaves. This study describes the identification of two flavonoids: 3', 5, 7
trihydroxy-3, 4'-dimethoxyflavone (compd. 1) and 3', 4', 5-trihydroxy-7-methoxy flavanone (compd. 2) and two sesquiterpenes
lactones: enhydrin (compd. 3) and a mixt. of enhydrin and uvedalin (compd. 4) isolated from Polymnia sonchifolia leaves and their
effects on the aflatoxin prodn. by Aspergillus flavus. The identification of the compds. were achieved by 1H and 13C NMR. All
compds. were tested in different concn., to evaluate the growth of Aspergillus flavus culture and the prodn. of aflatoxin. The compd.
1, at the concn. 15 μg/mL, inhibited 25% of the aflatoxin B1 prodn. (p<0.01). The compd. 4 inhibited 34% and 76% of the fungal growth
and AFB1 prodn. resp. These results show that Polymnia sonchifolia can be used for the development of agents to control aflatoxin
B1 prodn. by Aspergillus flavus.
Answer 100:
AMPK activators for activation of metabolism, and foods and beverages containing them. Murase, Takatoshi. (Kao Corp.,
Japan). Jpn. Kokai Tokkyo Koho (2007), 10pp. CODEN: JKXXAF JP 2007314446 A 20071206 Patent written in Japanese.
Application: JP 2006-144264 20060524. Priority: . CAN 148:32598 AN 2007:1386872 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))

JP 2007314446 A 20071206 JP 2006-144264 20060524
JP 2006-144264 20060524
flavanone
Abstract
Title foods and beverages, useful for prevention and/or treatment of life style-assocd. chronic metabolic diseases (e.g., obesity and
diabetes), contain flavones and/or flavanones as AMPK activators. Thus, 2-phenylchromone at 150 μM significantly enhanced
phosphorylation of AMPKα and β in Hepa 1-6.
Answer 101:
A Study of Isomeric Diglycosyl Flavonoids by SORI CID of Fourier Transform Ion Cyclotron Mass Spectrometry in Negative
Ion Mode. Yan, Cunyu; Liu, Shuying; Zhou, Yihan; Song, Fengrui; Cui, Meng; Liu, Zhiqiang. Changchun Center of Mass
Spectrometry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, Peop. Rep. China. Journal
of the American Society for Mass Spectrometry (2007), 18(12), 2127-2136. Publisher: Elsevier Inc., CODEN: JAMSEF ISSN:
Abstract
High-resoln. Sustained off resonance irradn. (SORI) CID was employed to distinguish four pairs of isomeric diglycosyl flavonoids in
the neg. mode using the electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry (ESI FTICR MS). All of
these isomers can be distinguished via MS/MS data. For these diglycosyl flavones and flavanones, the deprotonated α1→6 linkage
diglycosyl flavonoids produce fewer fragments than the α1→2 linkage type compds. and the Retro-Diels-Alder (RDA) reaction in
MS/MS only takes place when the aglycon is a flavanone and glycosylated with an α1→2 intersaccharide linkage disaccharide. The
deprotonation sites after collisional activation are discussed according to the high mass accuracy and high-resoln. data of tandem
spectrometry. Some of these high-resoln. SORI CID product ions from α1→2 linkage diglycosyl flavonoids involve multibond
cleavages; the possible mechanism is discussed based on the computer modeling using Gaussian 03 program package at the
B3LYP/6-31G level of theory. Unambiguous elementary compn. data provides fragmentation information that has not been reported
previously.
Answer 102:
One step purification of flavanone glycosides from Poncirus trifoliata by centrifugal partition chromatography. Kim, Chul
Young; Lee, Hee Ju; Lee, Mi Kyeong; Ahn, Mi-Jeong; Kim, Jinwoong. Natural Product Research Center, KIST Gangneung Institute,
Gangneung, S. Korea. Journal of Separation Science (2007), 30(16), 2693-2697. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA,
CODEN: JSSCCJ ISSN: 1615-9306. Journal written in English. CAN 148:213554 AN 2007:1367856 CAPLUS (Copyright (C)
Abstract
Flavanone glycosides were successfully sepd. from the crude ext. of P. trifoliata by preparative centrifugal partition chromatog. with a
two-phase solvent system composed of Et acetate-acetonitrile-water (3:2:5, vol./vol./vol.). Naringin (50.0 mg), neoponcirin (16.8 mg),
and poncirin (71.9 mg) were purified from the 524 mg crude ext. in only 1 step. The purities of the isolated compds. were detd. to be
>90% by HPLC anal. and their structures were elucidated by 1H NMR, 13C NMR, and ESI-MS.
Answer 103:
flavanone
5,7,3',4'-Tetrahydroxy flavanone having protective effects on the UV-induced cell death in human keratinocytes. Cho, Ssang
Goo; Lee, Eung Ryoung; Kang, Yong Jin. (Konkuk University Industrial Cooperation Corp., S. Korea). Repub. Korea (2007), No
pp. given. CODEN: KRXXFC KR 729732 B1 20070620 Patent written in Korean. Application: KR 2006-5735 20060119. Priority:
. CAN 147:548118 AN 2007:1345898 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))

KR 729732 B1 20070620 KR 2006-5735 20060119
KR 2006-5735 20060119
Abstract
This invention relates to 5,7,3',4'-tetrahydroxy flavanone having protective effects on the UV-induced cell death in human
keratinocytes to inhibit apoptosis of human keratinocytes caused by UV by inhibiting prodn. of reactive oxygen species due to UV in
cells and activity redn. of p38 MAP(mitogen-activated protein) kinase through treating the human skin exposed to UV with the
flavonoid. A compn. for inhibiting apoptosis of human keratinocytes caused by UV comprises the 5,7,3',4'-tetrahydroxy flavanone
isolated from the plant such as Viscum album var. as an effective ingredient, wherein the compn. is a cosmetic or pharmaceutical
compn. and is formulated as granule, tablet, capsule, drink, cream or lotion. The daily dosage of 5,7,3',4'-tetrahydroxy flavanone is
0.1-1000 mg per adult.
Answer 104:
Cytotoxic chalcones and antioxidants from the fruits of Syzygium samarangense (Wax Jambu). Simirgiotis, Mario J.; Adachi,
Seiji; To, Satoshi; Yang, Hui; Reynertson, Kurt A.; Basile, Margaret J.; Gil, Roberto R.; Weinstein, I. Bernard; Kennelly, Edward J.
Department of Biological Sciences, Lehman College and The Graduate Center, City University of New York, Bronx, NY, USA.
Food Chemistry (2008), 107(2), 813-819. Publisher: Elsevier B.V., CODEN: FOCHDJ ISSN: 0308-8146. Journal written in
Abstract
Bioassay-guided fractionation of the methanolic exts. of the pulp and seeds of the fruits of Syzygium samarangense (Blume) Merr.
and L.M. Perry led to the identification of four cytotoxic compds. and eight antioxidants on the basis of HPLC-PDA anal., MS, and
various NMR spectroscopic techniques. Three C-methylated chalcones, 2',4'-dihydroxy-3',5'-dimethyl-6'-methoxychalcone (1),
2',4'-dihydroxy-3'-methyl-6'-methoxychalcone (stercurensin, 2), and 2',4'-dihydroxy-6'-methoxychalcone (cardamonin, 3), were isolated
and displayed cytotoxic activity (IC50 = 10, 35, and 35 μM, resp.) against the SW-480 human colon cancer cell line. Also a no. of
known antioxidants were obtained including six quercetin glycosides: reynoutrin (4), hyperin (5), myricitrin (6), quercitrin (7), quercetin
(9), and guaijaverin (10), one flavanone: (S)-pinocembrin (8), and two phenolic acids: gallic acid (11) and ellagic acid (12).
Answer 105:
flavanone
Extraction and identification of total flavanone from longan pericarp. Huang, Suoyi; Tang, Yulian; Li, Haini; Li, Rong.
Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Guangxi Province, Peop. Rep. China. Zhongyaocai
(2006), 29(8), 767-769. Publisher: Guojia Shipin Yaopin Jiandu Guanliju, Zhongyaocai Xinxi Zhongxinzhan, CODEN: ZHONAR ISSN:
1001-4454. Journal written in Chinese. AN 2007:1342302 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
In order to make use of the resources of total flavanone in pericarp of longan, extn. and identification were discussed. The flavonids
were extd. with ethanol. Spectrophotometry was used to check the flavanone. The total flavanone in the pericarp was 1.101 mg/mL
and the rate of recovery was 99.98%. The extn. and purifying methods in this expt. could get the outcome and the purity of the
flavanone very high. This method was a purely phys. process and had not any pollution. It was an ideal way to ext. the flavanone of
longan skin.
Answer 106:
Total flavanone of ficus microcarpa L. leaf withdraws and distinction. Long, Guangjin; Huang, Ye; Jiang, Linhua; Huang,
Suoyi. Undergraduate of Clinical Medicine, Grade 2001, Youjiang Medical College for Nationalities, Baise, Guangxi Province, Peop.
Rep. China. Shizhen Guoyi Guoyao (2006), 17(8), 1425-1426. Publisher: Shizhen Guoyi Guoyao Bianweihui, CODEN: SGGHAL
ISSN: 1008-0805. Journal written in Chinese. AN 2007:1342121 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
In order to make use of the resources of Ficus microearpa L. leaf, avoiding waste, purely phys. process flow was used and the
spectrophotometry method of which withdrawed the flavanone from Ficus microearpa L. leaf was introduced and the flavanone which
withdrawed from Ficus microearpa L. leaf was checked. The contents of the total flavanone of onion was C=8.36% and rate of the
recovery was 97.9%. Using this text which provided the withdrawal and purifying methods the outcome and purity of the flavanone
were all very high. This method was purely phys. process, and had no chem. change and pollution. It was ideal to withdraw the
flavanone of Ficus microearpa L. leaf.
Answer 107:
Extraction and distinguish of the total flavanone from orange peel. Huang, Suoyi; Luo, Yan; Zhang, Jingxuan; Wang, Sanyan;
Lu, Huiyu. Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Guangxi Province, Peop. Rep. China.
Shizhen Guoyi Guoyao (2006), 17(8), 1495-1496. Publisher: Shizhen Guoyi Guoyao Bianweihui, CODEN: SGGHAL ISSN:
1008-0805. Journal written in Chinese. CAN 148:409803 AN 2007:1342001 CAPLUS (Copyright (C) 2008 ACS on SciFinder
(R))
Abstract
In order to make use of the resources of orange peel, avoiding waste, purely phys. process flow and spectrophotometry to introduce
the method of which extd. the flavanone from the orange peel were used, and the flavanone which withdrew from the lotus rhizome was
checked. By this method getting the contents of the total flavanone of orange peel was C = 4.49% and rate of the recovery was
98.0%. Using this text which provided the withdrawal and purifying methods to get the outcome and purity of the flavanone were all
very high. This method was purely phys. process, and had no chem. change and pollution. It was ideal to withdraw the flavanone of
orange peel.
Answer 108:
flavanone
Structures and anti-histamine activity of chalcones & aurones compounds from Bidens parviflora Willd. Wang, Jue; Wang,
Naili; Yao, Xinsheng; Kitanaka, Susumu. School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University,
Shenyang, Peop. Rep. China. Asian Journal of Traditional Medicines (2007), 2(1), 23-29. Publisher: Hong Kong Asiamed Publish
House, CODEN: AJTMCS ISSN: 1817-4337. Journal written in English. AN 2007:1338626 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Using the effects on histamine release of Bidens parviflora Willd. to identify biol. active compds. Five chalcones,two flavanones and
two aurones were isolated and identified as 2'-hydroxy-3,4,4'-trimethoxy chalcone (1), 4,2',4',6'-tetramethoxy dihydrochalcone (2),
3,4,2',4',6'-pentamethoxy dihydrochalcone (3,I), 7,3',4'-trihydroxy flavanone (4), 3',4'-dihydroxy flavanone 7-O-β-D-glucoside (5),
3,4,2'-trihydroxy chalcone 4'-O-β-D-glucoside (6), 3-methoxy-4,2',3'-trihydroxy chalcone 4'-O-β-D-glucoside (7), sulfuretin
6-O-β-D-glucoside (8), and maritimetin 7-O-β-D-glucoside (9). Compds. 1-7 were obtained from Bidens parviflora Willd. for the first
time, compd. 3 is a new dihydrochalcone, and 1 and 2 were isolated from natural sources for the first time. The chalcones glucosides
and aurones glucosides exhibited activity in anti-allergic assays of histamine in rat mast cells induced by an antigen-antibody reaction
and the inhibitory activity of NO prodn. by macrophages is compared and discussed.
Answer 109:
Standardized biosynthesis of flavan-3-ols with effects on pancreatic beta-cell insulin secretion. Chemler, Joseph A.; Lock,
Lye T.; Koffas, Mattheos A. G.; Tzanakakis, Emmanuel S. Department of Chemical and Biological Engineering, State University of
New York at Buffalo, Buffalo, NY, USA. Applied Microbiology and Biotechnology (2007), 77(4), 797-807. Publisher: Springer,
CODEN: AMBIDG ISSN: 0175-7598. Journal written in English. CAN 148:160360 AN 2007:1329755 CAPLUS (Copyright (C)
Abstract
Flavan-3-ols, such as green tea catechins represent a major group of phenolic compds. with significant medicinal properties. The
authors describe the construction and optimization of Escherichia coli recombinant strains for the prodn. of mono- and dihydroxylated
catechins from their flavanone and phenylpropanoid acid precursors. Use of glucose minimal medium, Fe(II), and control of oxygen
availability during shake-flask expts. resulted in prodn. yield increases. Addnl. prodn. improvement resulted from the use of medium
rather than high-copy no. plasmids and, in the case of mono-hydroxylated compds., the addn. of extracellular cofactors in the culture
medium. The established metabolic engineering approach allowed the biosynthesis of natural catechins at high purity for assessing
their possible insulinotropic effects in pancreatic β-cell cultures. The authors demonstrated that (+)-afzelechin and (+)-catechin
modulated the secretion of insulin by pancreatic β-cells. These results indicate the potential of applying metabolic engineering
approaches for the synthesis of natural and non-natural catechin analogs as drug candidates in diabetes treatments.
Answer 110:
Simultaneous determination of flavonoids in Ixeridium gracile by micellar electrokinetic chromatography. Zhang, Yu;
Chen, Juan; Ma, Xue-Mei; Shi, Yan-Ping. Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical
Physics, Chinese Academy of Sciences, Lanzhou, Peop. Rep. China. Journal of Pharmaceutical and Biomedical Analysis (2007),
45(5), 742-746. Publisher: Elsevier B.V., CODEN: JPBADA ISSN: 0731-7085. Journal written in English. CAN 148:62302 AN
flavanone
Abstract
A micellar electrokinetic chromatog. (MEKC) method has been developed for the quant. anal. of five flavonoids: luteolin 7-O-glucoside
(LG), 2',4'-dihydroxy-dihydrochalcone (DD), 2',4'-dihydroxy-chalcone (DC), 7-hydroxy-flavanone (HF) and quercetin 3-O-galactoside
(QG) in Ixeridium gracile with UV detection at 275 nm. The applied voltage was 25 kV and the capillary temp. was kept const. at 25°.
The effects of buffer pH, the concn. of electrolyte and org. modifier on migration behavior were studied. Optimum sepn. condition
was achieved with 15 mM borate, 30 mM SDS and 10% (vol./vol.) ethanol at pH 10.5. Regression equations showed good linear
relationships (correlation coeffs.: 0.9984, 0.9991, 0.9994, 0.9995 and 0.9997) between the peak area of each compd. and their concns.
The relative std. deviations (R.S.D.) of the migration time and peak area were less 1.67 and 3.53% (intra-day), and 1.82 and 3.73%
(inter-day), resp., under the optimum sepn. conditions. The contents of the five active compds. in I. gracile were detd. with
satisfactory repeatability and recovery.
Answer 111:
Interactions affecting the bioavailability of dietary polyphenols in vivo. Scholz, Susanne; Williamson, Gary. Nestle
Research Center, Lausanne, Switz. International Journal for Vitamin and Nutrition Research (2007), 77(3), 224-235. Publisher:
Hogrefe & Huber Publishers, CODEN: IJVNAP ISSN: 0300-9831. Journal; General Review written in English. CAN 148:10278
Abstract
A review. Polyphenols are abundant dietary plant constituents assocd. with health-promoting effects. Factors influencing the
bioavailability of dietary polyphenols, esp. flavanols, flavonols, flavanones, flavones, and hydroxycinnamic (phenolic) acids, are
discussed. Most factors tested so far indicate that bioaccessibility, defined as the amt. of compd. reaching the enterocyte in a form
suitable for absorption, is the most important factor detg. the polyphenols absorption in the gut. Factors improving the absorption of
flavonols, notably quercetin and its metabolites, are the nature of the sugar moiety and soly. as modified by ethanol, fat, and
emulsifiers. The absorption of flavanols, notably green tea catechins, is affected by epimerization reactions occurring during food
processing, presence of lipid and carbohydrate, and is improved in the presence of piperine and tartaric acid. The bioavailability of
flavanones, such as hesperidin, is strongly affected by the type of sugar moiety. Phenolic acids bioavailability is affected by the
attached sugar, which can covalently link these compds. to the cereal bran matrix. In the few examples tested, absorption of
polyphenols is dependent on the release from food matrix. There are only a few examples reported, but where information is available,
the absorption increases with dose but is sometimes linear and sometimes satd. The lack of systematic information on the effects of
other components on the bioavailability of polyphenols needs to be addressed. More human studies are needed to establish general
principles affecting polyphenol absorption in vivo. Information from such expts. could be useful for the optimal design of future
bioefficacy studies.
Answer 112:
Separation of two new prenylated dihydroflavonoids from Dolichos tenuicaulis (Baker) Craib by high-speed counter-current
chromatography. Peng, Jin-Yong; Xu, Li-Na; Han, Xu; Xu, You-Wei; Qi, Yan; Xu, Qi-Wei. School of Pharmacy, Dalian Medical
University, Dalian, Peop. Rep. China. Fenxi Huaxue (2007), 35(10), 1444-1448. Publisher: Kexue Chubanshe, CODEN:
FHHHDT ISSN: 0253-3820. Journal written in Chinese. CAN 148:17960 AN 2007:1312362 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
flavanone
The sepn. and isolation of chem. constituents from Dolichos tenuicaulis (Baker) Craib by high-speed counter-current chromatog.
(HSCCC) were achieved. The solvent system composed of petroleum ether:ethyl acetate:ethanol:water (1:1.2:1.2:1, V/V) was
selected to purify the compds., the upper phase was used as the stationary phase, the lower phase was used as the mobile phase at a
flow rate of 2.0 mL/min, and the app. was controlled at 800 r/min and 30°, and the effluent was monitored at 280 nm. Under the
optimized conditions, two pure compds. with the amts. of 95.3 mg and 84.5 mg were produced from 400 mg crude sample only in one
run, and the chem. structures of the targets were elucidated as
(2S)-5,2',6'-trihydroxy-8-prenyl-6,7-(3-prenyl-2,2-dimethyl-1-keone-cyclohexadiene)-flavanone (1) and
(2S)-5,2',6'-trihydroxy-8-prenyl-6,7-(3-prenyl-2,2-dimethylpyrano)-3',4'-(2,2-dimethyl-1-keone-cyclohexadiene)-flavanone (2) by
physico-chem. properties and spectra data. This sepn. method was simple, and the compds. 1 and 2 were new compds.
Answer 113:
Biosynthesis of 5-deoxyflavanones in microorganisms. Yan, Yajun; Huang, Lixuan; Koffas, Mattheos A. G. Department of
Chemical and Biological Engineering, University at Buffalo, the State University of New York, Buffalo, NY, USA. Biotechnology
Journal (2007), 2(10), 1250-1262. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: BJIOAM ISSN: 1860-6768. Journal
Abstract
Flavanones are the common precursors of plant polyphenolic compds. collectively known as flavonoids. Leguminous plants have
evolved a distinct class of flavanone mols., known as 5-deoxyflavanones that play important roles in their symbiotic interactions. A
four-step metabolic circuit was constructed in Escherichia coli with plant genes from heterologous origins: 4-coumarate:CoA ligase from
Petroselinum crispum, chalcone synthases (CHS) from Medicago sativa and Petunia x hybrida and chalcone reductase and chalcone
isomerase from M. sativa. Evaluation of the different recombinant strains in shake flask expts. demonstrated that P. hybrida rather
than M. sativa CHS resulted in the highest liquiritigenin prodn. levels in glucose minimal medium, starting from precursor p-coumaric
acid. Expression of the same recombinant pathway in Saccharomyces cerevisiae resulted in the accumulation of both
5-hydroxyflavanone and 5-deoxyflavanone, with the yields of the later lower than that achieved in E. coli. Other phenylpropanoid acid
precursors, such as cinnamic acid and caffeic acid could also be metabolized through the recombinant pathway, yielding corresponding
5-deoxyflavanone compds. The construction of such recombinant strains for 5-deoxyflavanone biosynthesis offers an alternative
way to biochem. characterize flavonoid biosynthetic enzymes and promising prodn. platforms for the biosynthesis of such high-value
natural products.
Answer 114:
Inhibition of mammalian collagenase, matrix metalloproteinase-1, by naturally-occurring flavonoids. Lim, Hyun; Kim, Hyun
Pyo. College of Pharmacy, Kangwon National University, Chunchon, S. Korea. Planta Medica (2007), 73(12), 1267-1274.
Publisher: Georg Thieme Verlag, CODEN: PLMEAA ISSN: 0032-0943. Journal written in English. CAN 148:112688 AN
Abstract
Some plant flavonoids in the form of whole plant exts. were used topically for skin inflammatory disorders. Since matrix
metalloproteinase-1 (MMP-1, collagenase-1) plays an important role in unbalanced turn-over or rapid breakdown of collagen mols. in
human inflamed/UV-irradiated skin, the effects of natural flavonoids on MMP-1 activity and MMP-1 expression were studied to
establish the therapeutic potential. Against recombinant human MMP-1, flavonols such as quercetin and kaempferol were strong
inhibitors with IC50 values of 39.6 and 43.7 μM, resp., while flavones such as apigenin and wogonin showed only weak inhibitory
activity. In addn., quercetin, kaempferol, apigenin, and wogonin (12.5-25.0 μM) strongly inhibited MMP-1 induction in
flavanone
12-O-tetradecanoylphorbol 13-acetate-treated human dermal fibroblasts, but naringenin (a flavanone) did not. By means of the
electrophoretic mobility shift assay, these flavonoids were also found to inhibit activation of the transcription factor, activator protein-1
(AP-1). Moreover, quercetin inhibited extracellular signal-regulated protein kinase (ERK) and p38 mitogen-activated protein kinase
(MAPK) activation, and kaempferol inhibited p38 MAPK and c-Jun N-terminal kinase (JNK) activation among the MAPKs tested. In
contrast, flavones and naringenin did not inhibit the activation of these 3 MAPKs. These results have shown, for the 1st time, that
naturally-occurring flavonoids (quercetin, kaempferol, apigenin, and wogonin) inhibit MMP-1 and down-regulate MMP-1 expression via an
inhibition of the AP-1 activation although the cellular inhibitory mechanisms differ depending on their chem. structures. Therefore,
certain plant flavonoids or plant exts. with these flavonoids as major components may be beneficial to treat some skin inflammatory
disorders and to protect skin from photoaging.
Answer 115:
Sigmoidine L, a new antibacterial flavonoid from Erythrina sigmoidea (Fabaceae). Kouam, Jacques; Etoa, Francois-Xavier;
Mabeku, Laure BrigitteKouitcheu; Fomum, Zacharias Tanee. Department of Organic Chemistry, Faculty of Science, University of
Yaounde I, Cameroon. Natural Product Communications (2007), 2(11), 1105-1108. Publisher: Natural Product Inc., CODEN:
NPCACO ISSN: 1934-578X. Journal written in English. CAN 148:163619 AN 2007:1283900 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Chem. analyses of the stem bark of E. sigmoidea (Fabaceae) yielded a new flavonoid, designated sigmoidin L (1), the known
erythrinasinate, E-p-coumaric acid docosyl ester, and 3'-prenylnaringenin, reported here for the 1st time for the stem bark of
E.sigmoidea. The structure of 1 was established by chem. and spectroscopic means as
5,7,3',4'-tetrahydroxy-5'-[3''-methyl-4''-oxobut-(1''Z)enyl]flavanone. Sigmoidin L exhibited significant antibacterial potency in vitro
against Staphylococcus aureus and Proteus vulgaris.
Answer 116:
Transcriptional regulation of anthocyanin biosynthesis in ripening fruits of grapevine under seasonal water deficit.
Castellarin, Simone D.; Pfeiffer, Antonella; Sivilotti, Paolo; Degan, Mirko; Peterlunger, Enrico; Di Gaspero, Gabriele. Dipartimento di
Scienze Agrarie e Ambientali, University of Udine, Udine, Italy. Plant, Cell and Environment (2007), 30(11), 1381-1399.
Publisher: Blackwell Publishing Ltd., CODEN: PLCEDV ISSN: 0140-7791. Journal written in English. CAN 148:351375 AN
Abstract
Anthocyanin biosynthesis is strongly up-regulated in ripening fruit of grapevines (Vitis vinifera L.) grown under drought conditions. We
investigated the effects of long-term water deficit on the expression of genes coding for flavonoid and anthocyanin biosynthetic
enzymes and related transcription factors, genes sensitive to endogenous [sugars, abscisic acid (ABA)] and environmental (light)
stimuli connected to drought stress, and genes developmentally regulated in ripening berries. Total anthocyanin content has increased
at harvest in water-stressed (WS) fruits by 37-57% in two consecutive years. At least 84% of the total variation in anthocyanin
content was explained by the linear relationship between the integral of mRNA accumulation of the specific anthocyanin biosynthetic
gene UDP-glucose: flavonoid 3-O-glucosyltransferase (UFGT) and metabolite content during time series from veraison through
ripening. Chalcone synthase (CHS2, CHS3) and flavanone 3-hydroxylase (F3H) genes of the flavonoid pathway showed high
correlation as well. Genes coding for flavonoid 3',5'-hydroxylase (F3'5'H) and O-methyl-transferase (OMT) were also up-regulated in
berries from dehydrated plants in which anthocyanin compn. enriched in more hydroxylated and more methoxylated derivs. such as
malvidin and peonidin, the grape anthocyanins to which human gastric bilitranslocase displays the highest affinity. The induction in
flavanone
WS plants of structural and regulatory genes of the flavonoid pathway and of genes that trigger brassinosteroid hormonal onset of
maturation suggested that the interrelationships between developmental and environmental signalling pathways were magnified by
water deficit which actively promoted fruit maturation and, in this context, anthocyanin biosynthesis.
Answer 117:
Multi-substituted flavanone derivative, its preparation and application. Hu, Yongzhou; Liu, Tao; He, Qiaojun; Yang, Bo; Luo,
Peihua. (Zhejiang University, Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 14pp. CODEN:
CNXXEV CN 101066963 A 20071107 Patent written in Chinese. Application: CN 1006-9248 20070608. Priority: . CAN

CN 101066963 A 20071107 CN 2007-10069248 20070608
CN 2007-10069248 20070608
Abstract
The claimed flavone derivs. have general structure I (R1 = C1-3 (un)branched alkyl; Ar = (un)substituted Ph; R2 = chain or cyclic
tertiary amine NR3R4; R3 and R4 = Me, Et, C1-4 alkyl alc., carboxylic acid, ester, amine, or forming 5- or 6-membered ring with
oxygen or nitrogen). Title compds. were prepd. from 2-acetyl-1,3,5-trihydroxybenzene via etherification, arom. aldehyde condensation,
amination, cyclization, and selective dealkylation to provide the claimed products. The flavone deriv. can be used to prep.
antineoplastic medicine.
R2
R1O O Ar
OH O I
Answer 118:
Separation and purification of flavanone from aloes using four-course analogue moving bed chromatography. Zhang,
Dabing; Wang, Yahui; Meng, Qiang; Wang, Yan. (Jiangsu Hanbon Sci. & Tech. Co., Ltd., Peop. Rep. China). Faming Zhuanli
Shenqing Gongkai Shuomingshu (2007), 10pp. CODEN: CNXXEV CN 101066959 A 20071107 Patent written in Chinese.
flavanone
SciFinder (R))

CN 101066959 A 20071107 CN 2007-10022902 20070524
CN 2007-10022902 20070524
Abstract
Title method comprises hot water extg. dry Aloes, filtering, Et acetate extg. at room temp. for 3-5 h, filtering, evapg. to dry; purifying
ext. via four-course analog moving bed chromatog., eluting with methanol-water (45:55), vacuum concg., freeze drying.
Answer 119:
Total flavanone of Murraya paniculata extraction and the identification by ultrasonic wave. Huang, Suoyi; Yang, Wenhui; Li,
Weibin; Li, Rong. Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Guangxi Province, Peop. Rep.
China. Shizhen Guoyi Guoyao (2006), 17(3), 395-396. Publisher: Shizhen Guoyi Guoyao Bianweihui, CODEN: SGGHAL ISSN:
1008-0805. Journal written in Chinese. CAN 148:303454 AN 2007:1250332 CAPLUS (Copyright (C) 2008 ACS on SciFinder
(R))
Abstract
In order to make use of the resources of murraya paniculata, the extn. of total flavanone of Murraya paniculata was studied. The
flavonoids were extd. by ethanol as the solvent from Murraya kwangsiensis with ultrasonic wave and ethanol extn. Using
spectrophotometry, the flavanone of murraya paniculata was extd. and checked. By this method getting the d. of the total flavanone
of murraya paniculata was C = 1.0128 mg/mL and the rate of recovery was 102.5%. This text provides the extn. and purifying
methods to get the outcome and the purity of the flavanone were all very high. This method is a purely phys. process and has not
any pollution. It is an ideal way to ext. the flavanone of murraya paniculata.
Answer 120:
The total flavanone of gingers extraction and the distinction. Huang, Suoyi; Luo, Yan; Zhang, Jingxuan; Wang, Sanyan; Lu,
Huiyu. Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Guangxi Province, Peop. Rep. China.
Shizhen Guoyi Guoyao (2006), 17(5), 779-780. Publisher: Shizhen Guoyi Guoyao Bianweihui, CODEN: SGGHAL ISSN: 1008-0805.
Abstract
In order to make use of the resources of the gingers, avoid wasting, approach the extn. and detn. contents of the total flavanone of
the gingers, purely phys. process flow was used and the method of which extd. the flavanone from the gingers was introduced, and
flavanone
the flavanone which extd. from the Lotus rhizome was checked. The content of the total flavanone of gingers was 2.63% and the rate
of recovery was 97.8%. This method was purely phys. process, and had no chem. pollution. It was ideal ways to ext. the flavanone
of gingers.
Answer 121:
Flavonoids from Cactaceae Fruits. Johnson, Charles A.; Walker, Mindy; Scholes, Chad M.; Chapman, James M. Department
of Chemistry, Rockhurst University, Kansas City, MO, USA. Abstracts, 42nd Midwest Regional Meeting of the American
Chemical Society, Kansas City, MO, United States, November 7-10 (2007), GENERAL-294. Publisher: American Chemical
Society, Washington, D. C CODEN: 69JZDO Conference; Meeting Abstract written in English. AN 2007:1247172 CAPLUS
Abstract
A characterization of flavonols, betacyanins and possible anthocyanins from the fruits of several types of cacti by LC/ESI/MS-MS
was conducted. The anal. included fruits from the Mammillaria and Opuntia genera. Previous work by Miller on the floral pigments of
Echinocereus demonstrated the presence of a variety of flavone, flavonol, flavanone, and dihydroflavonol glycosides based upon the
fundamental aglycons naringenin, eriodictyol, dihydrokaempferol, dihydroquercetin, apigenin, luteolin, kaempferol, and quercetin. Work
on the fruits of Cactaceae has been limited to three species of Opuntia and the identification of betacyanins. The current investigation
attempted to verify the presence of similar flavonols and betacyanins in the fruits of other members of the Cactaceae family and to
explore the possible presence of anthocyanins. We have been able to identify several flavonols based on luteolin and isorhametin
within the fruits as well as several tentatively identified anthocyanidins based on cyanidin and delphinidin.
Answer 122:
Synergistic mixture of glycosyl flavanones and xanthines for browning skin or hair. Vielhaber, Gabriele; Schaper, Karin;
Lange, Sabine. (Symrise G.m.b.H. & Co. K.-G., Germany). PCT Int. Appl. (2007), 75pp. CODEN: PIXXD2 WO 2007122251 A2
20071101 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ,
DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA,
LC, LK, LR, LS, LT, LU, LY, MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC,
SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR,
GB, GR, IE, IS, IT, LU, MC, MT, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English.
Application: WO 2007-EP54065 20070425. Priority: US 2006-794514 20060425. CAN 147:474339 AN 2007:1243152 CAPLUS

WO 2007122251 A2 20071101 WO 2007-EP54065 20070425
WO 2007122251 A3 20080306
DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG,
KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG,
NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR,
TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW
flavanone
PT, RO, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG, BW, GH, GM,
KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM, AP, EA, EP,
OA
US 2006-794514P P 20060425
Abstract
The present invention concerns the use of a formulation contg. or consisting of (a) one or more xanthines, (b) one or more flavanone
glycoside contg. glucose or rhamnose or saccharide radicals, and (c) optionally a skin or hair conditioning or cleansing substance,
wherein the ratio by wt. of the amt. of (a) xanthines contained in the formulation to the amt. of (b) flavanone glycoside contained in
total in the formulation is in the range from 50:1 to 1:10, as an agent for browning skin or hair in vivo. A skin browing water-in-oil
emulsion with UVA/B broadband protection contains caffeine, naringin, dihydroacetone and other ingredients. A mixt. of caffeine and
naringin or morin are highly synergistic active ingredient combinations, while mixts. of caffeine and epicatechin or phloridzin have an
antagonistic rather than a synergistic effect.
Answer 123:
The total flavanone of corn silk extraction and distinction. Huang, Ye; Long, Guangjin; Jiang, Linhua; Huang, Suoyi. Youjiang
Medical College for Nationalities, Baise, Guangxi Province, Peop. Rep. China. Shizhen Guoyi Guoyao (2006), 17(6), 1008-1009.
Publisher: Shizhen Guoyi Guoyao Bianweihui, CODEN: SGGHAL ISSN: 1008-0805. Journal written in Chinese. CAN 148:139531
Abstract
A method to ext. flavonoids from corn stigma was established in order to make use of the resources of corn silk and avoid waste.
Flavonoids were extd. using purely phys. process and detected with spectrophotometry. The results showed that content of total
flavonoids in corn silk was 6.45% and rate of the recovery was 97.9%. The output and purity of flavonoids with the process were all
very high. This method was purely phys. process, and had not any chem. change and pollution. It was an ideal way to ext.
flavonoids of corn silk.
Answer 124:
Theoretical Calculation of Electronic Circular Dichroism of the Rotationally Restricted 3,8''-Biflavonoid Morelloflavone.
Ding, Yuanqing; Li, Xing-Cong; Ferreira, Daneel. National Center for Natural Products Research, Research Institute of
Pharmaceutical Sciences, and Department of Pharmacognosy, School of Pharmacy, The University of Mississippi, University, MS,
USA. Journal of Organic Chemistry (2007), 72(24), 9010-9017. Publisher: American Chemical Society, CODEN: JOCEAH ISSN:
Abstract
Theor. calcn. of electronic CD (ECD) of the rotationally restricted 3,8''-biflavonoid (+)-morelloflavone using time dependent d.
functional theory (TDDFT), performed at 298 K at B3LYP-SCRF/6-31G*//B3LYP/6-31G* level with COSMO model, permitted
flavanone
unequivocal assignment of its 2R,3S abs. configuration. The exptl. obsd. Cotton effect (CE) around 290 nm is contributed by the
acetophenone π → π* transition of the ABC-flavanone moiety and the electronic transition within the DEF-flavone moiety, while another
diagnostic pos. CE around 350 nm is attributable to the electronic interaction between the ABC-flavanone moiety and the DEF-flavone
moiety, as well as the electronic transition within the DEF-flavone moiety. The remarkable differences of the calcd. ECD of its two
rotamers indicate that the rotational restrictions significantly affect the ECD of 3,8''-biflavonoids. Empirical ECD rules derived from
monomeric flavonoids may not be applicable to configurational assignment of complex 3,8''-biflavonoids. This study has provided new
insights in interpreting the exptl. obsd. ECD spectra of this class of compds.
Answer 125:
Flavonoids for the prevention and treatment of cardiovascular diseases. Jeong, Tae Sook; Lee, Woo Song; Park, Ki Hun; Lee,
Byong Won; Park, Yong Dae; Kim, Min Jung; An, So Jin; Kim, Hyoung Chin; Moon, Og Sung; Won, Young Suk. (Korea Research
Institute of Bioscience and Biotechnology, S. Korea). Repub. Korean Kongkae Taeho Kongbo (2007), No pp. given. CODEN:
KRXXA7 KR 2007049812 A 20070514 Patent written in Korean. Application: KR 2005-106992 20051109. Priority: . CAN

KR 2007049812 A 20070514 KR 2005-106992 20051109
KR 2005-106992 20051109
Abstract
A flavonoid-based compd. is provided to show excellent antioxidative activity on low d. lipoprotein (LDL) and effectively inhibit the
activity of acyl-CoA:cholesterol acyltransferase (ACAT), thereby being useful for preventing and treating cardiovascular diseases,
such as hyperlipidemia, coronary heart disease, coronary sclerosis and myocardial infarction. The flavonoids are isolated from roots
of Cudrania tricuspidata.
Answer 126:
General method for determining flavonoids in medicinal plants and raw cosmetics using HPLC with a photodiode array
detector. Wang, L.-H.; Li, W.-H. Department of Applied Chemistry, Chia Nan University of Pharmacy and Science, Tainan,
Taiwan. Pharmaceutical Chemistry Journal (2007), 41(4), 225-231. Publisher: Springer, CODEN: PCJOAU ISSN: 0091-150X.
Abstract
The sepn. of flavonoids in medicinal plants and raw cosmetics was described by high performance liq. chromatog. with a photodiode
array detector. The influence of wavelength, mobile phase component, sample treatment including solvent selection and extn. and
other conditions affecting the sepn. were optimized. Elution with methanol/phosphoric acid (pH 2.0) in a Phenomenex C18 (25 cm × 4.6
mm i.d.) column allowed us to sep. twelve flavonoids in medicinal plants and raw cosmetics with high resoln. and short anal. time.
flavanone
Answer 127:
Extraction and determination of contents of the total flavanones of the leaves of phyllostachyspubescens. Huang, Suoyi;
Yao, Xiaomin; Qin, Chengjian; Liang, Yu. Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Guangxi
Province, Peop. Rep. China. Shizhen Guoyi Guoyao (2006), 17(7), 1228-1229. Publisher: Shizhen Guoyi Guoyao Bianweihui,
CODEN: SGGHAL ISSN: 1008-0805. Journal written in Chinese. CAN 148:409749 AN 2007:1186398 CAPLUS (Copyright (C)
Abstract
The extn. and detn. of contents of the total flavanones of the leaves of Phyllostachyspubescens was investigated. Purely phys.
process flow and spectrophotometry were used to ext. and check the flavanone of the leaves of Phyllostachyspubescens. By this
method the contents of the total flavanone of the leaves of Phyllostachyspubescens was C = 1.56% and the recovery rate was
99.4%. This text provided the extn. and purifying methods to get the outcome and the purity of the flavanones was high. This method
was a purely phys. process, and had not any chem. change and pollution. It was an ideal way to ext. the flavanone of the leaves of
Phyllostachyspubescens.
Answer 128:
Skin compositions containing Oldenlandia diffusa extract. Yamada, Yasuhiro; Morita, Satoshi; Otake, Tetsuo. (Narisu
Cosmetic Co., Ltd., Japan). Jpn. Kokai Tokkyo Koho (2007), 11pp. CODEN: JKXXAF JP 2007269752 A 20071018 Patent
written in Japanese. Application: JP 2006-100618 20060331. Priority: . CAN 147:433038 AN 2007:1173707 CAPLUS

JP 2007269752 A 20071018 JP 2006-100618 20060331
JP 2006-100618 20060331
Abstract
The invention relates to a c-kit gene expression inhibitor characterized by contg. Oldenlandia diffusa ext., wherein the agent is suitable
for use in a skin-whitening cosmetic. A c-kit gene expression inhibitor contg. Oldenlandia diffusa ext. with an antioxidant, an
antiinflammatory agent, a macromol. component, and/or a polyhydric alc. is also disclosed. For example, the effect of Oldenlandia
diffusa ext. on c-kit expression in human melanocyte with/without of other components was tested. Also, a cosmetic cream compn.
contg. beeswax 2, stearyl alc. 5, stearic acid 8, squalane 10, self-emulsifying glyceryl monostearate 3, polyoxyethylene cetyl ether 1,
sunflower seed ext. 2, 1,3-butylene glycol 5, Oldenlandia diffusa ext. 0.0001, KOH 0.3, preservative q.s., reduced NAD 0.1, and water
balance to 100 % was formulated.
Answer 129:
flavanone
The total flavanone of the Jasminum sambac air extraction and the identification by ultrasonic wave. Luo, Jian-hua; Meng,
Chun-yue; Zhang, Li-dan; Feng, Ling; Tan, Yong-ping; Huang, Suo-yi. Department of Clinical Medicine, Youjiang Medical College for
Nationalities, Baise, Guangxi, Peop. Rep. China. Weiliang Yuansu Yu Jiankang Yanjiu (2007), 24(5), 49-50. Publisher: Weiliang
Yuansu Yu Jiankang Yanjiu Zazhishe, CODEN: WYYJAF ISSN: 1005-5320. Journal written in Chinese. CAN 148:27650 AN
Abstract
For fully using the resources of the Jasminum sambac air, the method that withdrawes the flavanone from the Jasminum sambac air
was introduced by ultrasonic wave, and the method of distinct flavanone were elaborated, then the flavanone which withdrawed from
the Jasminum sambac air were checked, and then combined to immerse with ethanol that withdraws the total flavonoid. This operation
was simple, convenient, and pollution-free. The Jasminum sambac air has high development and utilization of high value.
Answer 130:
Study on extraction process of the total flavanone of Guixi's Folium artemisiae argyi by ultrasonic wave. Lu, Hai-feng; Luo,
Jian-hua; Zhang, Li-dan; Liu, Jiao; Meng, Chun-yue; Feng, Ling; Li, Lin; Huang, Suo-yi. Department of Chemistry, Youjiang Medical
College for Nationalities, Baise, Guangxi, Peop. Rep. China. Weiliang Yuansu Yu Jiankang Yanjiu (2007), 24(5), 21-23.
Publisher: Weiliang Yuansu Yu Jiankang Yanjiu Zazhishe, CODEN: WYYJAF ISSN: 1005-5320. Journal written in Chinese. AN
Abstract
In order to make use of the resources of Folium artemisiae argyi, avoid wasting and approach the extn. of total flavanone of Folium
Artemisiae Argyi. The flavonids were extd. by ethanol as the solvent from folium artemisiae argyi with ultrasonic wave and ethanol
extn. Using spectrophotometry to ext. and check the flavanone of Folium Artemisiae Argyi. By this method getting the d. of the total
flavanone of Folium Artemisiae Argyi is C=0.6599 mg/mL and the rate of recovery is 102.6 %. This text provides the extn. and
purifying methods to get the outcome and the purity of the flavanone are all very high. This method is a purely phys. process and
has not any pollution. It is an ideal way to ext. the flavanone of Folium artemisiae argyi.
Answer 131:
Flavonoids affect actin functions in cytoplasm and nucleus. Boehl, Markus; Tietze, Simon; Sokoll, Andrea; Madathil, Sineej;
Pfennig, Frank; Apostolakis, Joannis; Fahmy, Karim; Gutzeit, Herwig O. Institute of Zoology, Technical University Dresden,
Dresden, Germany. Biophysical Journal (2007), 93(8), 2767-2780. Publisher: Biophysical Society, CODEN: BIOJAU ISSN:
Abstract
Based on the identification of actin as a target protein for the flavonol quercetin, the binding affinities of quercetin and structurally
related flavonoids were detd. by flavonoid-dependent quenching of tryptophan fluorescence from actin. Irresp. of differences in the
hydroxyl pattern, similar Kd values in the 20 μM range were obsd. for six flavonoids encompassing members of the flavonol,
isoflavone, flavanone, and flavane group. The potential biol. relevance of the flavonoid/actin interaction in the cytoplasm and the
flavanone
nucleus was addressed using an actin polymn. and a transcription assay, resp. In contrast to the similar binding affinities, the
flavonoids exert distinct and partially opposing biol. effects: although flavonols inhibit actin functions, the structurally related flavane
epigallocatechin promotes actin activity in both test systems. IR spectroscopic evidence reveals flavonoid-specific conformational
changes in actin which may mediate the different biol. effects. Docking studies provide models of flavonoid binding to the known
small mol.-binding sites in actin. Among these, the mostly hydrophobic tetramethylrhodamine-binding site is a prime candidate for
flavonoid binding and rationalizes the high efficiency of quenching of the two closely located fluorescent tryptophans. The exptl. and
theor. data consistently indicate the importance of hydrophobic, rather than H-bond-mediated, actin-flavonoid interactions. Depending
on the rigidity of the flavonoid structures, different functionally relevant conformational changes are evoked through an induced fit.
Answer 132:
Flavonoid composition of Citrus juices. Gattuso, Giuseppe; Barreca, Davide; Gargiulli, Claudia; Leuzzi, Ugo; Caristi, Corrado.
Dipartimento di Chimica Organica e Biologica, Universita di Messina, Messina, Italy. Molecules (2007), 12(8), 1641-1673.
Publisher: Molecular Diversity Preservation International, CODEN: MOLEFW ISSN: 1420-3049.
http://www.mdpi.org/molecules/papers/12081641.pdf Journal; General Review; Online Computer File written in English. CAN
Abstract
A review. In the early nineties the presence of flavonoids in Citrus juices began to attract the attention of a no. of researchers, as a
result of their biol. and physiol. importance. This short review will explore 2 different aspects. The first part will focus on anal.
techniques for the characterization of juices from different Citrus fruits regarding their flavonoid content (even if present in only trace
amts.), concg. on the most widely used methods (LC-MS and LC-MS-MS). The second part analyzes data reported in the literature
regarding the compn. of Citrus juices. The main components that were detected so far are flavanone-O-glycosides and flavone-O- or
-C-glycosides. The presence of such derivs. in various hand-squeezed and industrial juices is discussed, with special emphasis on
their correlation to different species.
Answer 133:
Permeability Profile Estimation of Flavonoids and other Phenolic Compounds by Biopartitioning Micellar Capillary
Chromatography. Diniz, Andrea; Escuder-Gilabert, Laura; Lopes, Norberto P.; Gobbo-Neto, Leonardo; Villanueva-Camanas, Rosa
Maria; Sagrado, Salvador; Medina-Hernandez, Maria Jose. Departamento de Ciencias Farmaceticas, CCS, Universidade Estadual de
Londrina, Londrina, PR, Brazil. Journal of Agricultural and Food Chemistry (2007), 55(21), 8372-8379. Publisher: American
Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 148:32200 AN 2007:1132951
Abstract
This paper points out the usefulness of biopartitioning micellar chromatog. (BMC) using capillary columns as a high-throughput primary
screening tool providing key information about the oral absorption, skin permeability, and brain-blood distribution coeffs. of 15
polyphenols (6 flavones, 2 flavonols, a flavanone, 2 flavan-3-ols, 3 phenolic acids, and a phloroglucinol) in a simple and economical
way. For the compds. studied, except vicenin-2, rutin, chlorogenic acid, p-hydroxycinnamic acid, and 4-hydroxybenzoic acid, maximal
oral absorption (>90%) can be expected, if there are not soly. problems or metabolic processes. On the other hand, the most retained
compds. in BMC, i.e., 5-hydroxyflavone, flavone, and flavanone, show the highest brain-blood distribution coeffs. and skin
permeability coeffs.
Answer 134:
flavanone
A feeding deterrent from Persicaria lapathifolia (polygonaceae) leaves to larvae of Gallerucida bifasciata (coleoptera:
chrysomelidae). Abe, Makoto; Niizeki, Masatsugu; Matsuda, Kazuhiro. Laboratory of Insect Science and Bioregulation, Graduate
School of Agriculture, Tohoku University, Miyagi, Japan. Applied Entomology and Zoology (2007), 42(3), 449-456. Publisher:
Japanese Society of Applied Entomology and Zoology, CODEN: APEZAW ISSN: 0003-6862. Journal written in English. AN
Abstract
Among 3 species of polygonaceous feeding leaf beetle, Galerucella grisescens, Gallerucida bifasciata, and Gastrophysa atrocyanea,
only G. bifasciata did not use a polygonaceous plant, P. lapathifolia, as a food. 2nd and 3rd instar larvae and adults of G. bifasciata
fed on the leaves; however, the feeding amt. decreased day by day and all died. The 1st instar larvae hardly fed on the leaves and
all larvae died. Biol. tests and chem. anal. revealed that feeding deterrents were present in P. lapathifolia leaves. A feeding deterrent
was isolated and identified as 3-hydroxy-5-methoxy-6,7-methylenedioxy flavanone. The compd. deterred 1st instar larvae of G.
bifaciata from feeding and significantly lessened the survival rate of the larvae at concns. >1.0 mg/mL. Larvae of G. grisescens were
not deterred from feeding by the compd. at 5 mg/mL. The presence of other fractions increased the feeding deterrent activity of the
compd. to 1st instar larvae of G. bifasciata. These results revealed that P. lapathifolia leaves contain multiple feeding deterrents to G.
bifasciata.
Answer 135:
Effect of xanthohumol and isoxanthohumol on 3T3-L1 cell apoptosis and adipogenesis. Yang, Jeong-Yeh; Della-Fera, Mary
Anne; Rayalam, Srujana; Baile, Clifton A. Department of Animal and Dairy Science 444 Edgar L. Rhodes Center for Animal and
Dairy Science, University of Georgia, Athens, GA, USA. Apoptosis (2007), 12(11), 1953-1963. Publisher: Springer, CODEN:
APOPFN ISSN: 1360-8185. Journal written in English. CAN 148:206423 AN 2007:1108444 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Xanthohumol (XN), the chalcone from beer hops has several biol. activities. XN has been shown to induce apoptosis in cancer cells
and also has been reported to be involved in lipid metab. Based on these studies and our previous work with natural compds., we
hypothesized that XN and its isomeric flavanone, isoxanthohumol (IXN), would induce apoptosis in adipocytes through the mitochondrial
pathway and would inhibit maturation of preadipocytes. Adipocytes were treated with various concns. of XN or IXN. In mature
adipocytes both XN and IXN decreased viability, increased apoptosis and increased ROS prodn., XN being more effective.
Furthermore, the antioxidants ascorbic acid and 2-mercaptoethanol prevented XN and IXN-induced ROS generation and apoptosis.
Immunoblotting anal. showed an increase in the levels of cytoplasmic cytochrome c and cleaved poly (ADP-ribose) polymerase
(PARP) by XN and IXN. Concomitantly, we obsd. activation of the effectors caspase-3/7. In maturing preadipocytes both XN and IXN
were effective in reducing lipid content, XN being more potent. Moreover, the major adipocyte marker proteins such as PPARγ,
C/EBPα, and aP2 decreased after treatment with XN during the maturation period and that of DGAT1 decreased after treatment with XN
and IXN. Taken together, our data indicate that both XN and IXN inhibit differentiation of preadipocytes, and induce apoptosis in
mature adipocytes, but XN is more potent.
Answer 136:
flavanone
Syntheses of 1,5-benzothiazepines: Part XXXIII. Syntheses and antimicrobial studies of

10-substituted-6-(4-methoxyphenyl)-6H-6a,7-dihydro-7-(4-methoxyphenyl/3,4-dimethoxyphenyl)[1]benzopyrano[3,4-c][1,5]benz
othiazepines. Pant, Seema; Sharma, Priyanka; Sharma, B. S.; Pant, Umesh C. LBS Government P.G. College, Jaipur, India.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (2007), 46B(9), 1537-1544. Publisher:
National Institute of Science Communication and Information Resources, CODEN: IJSBDB ISSN: 0376-4699. Journal written in
Abstract
Two flavindogenides, 3-(4-methoxybenzylidene)- and 3-(3,4-dimethoxybenzylidene)-2-(4-methoxyphenyl)flavanone are reacted with

5-substituted 2-aminobenzenethiols (the substituents being Br, Cl, F, Me, MeO, or EtO) to give 10-substituted
6-(4-methoxyphenyl)-6H-6a,7-dihydro-7-(4-methoxyphenyl/3,4-dimethoxyphenyl)[1]benzopyrano[3,4-c][1,5]benzothiazepines in 55-67%
yields. The products are characterized on the basis of anal. and spectral data. The synthesized compds. are screened for
antimicrobial activity against Staphylococcus aureus, Pseudomonas aeruginosa, and Candida albicans. All the methoxy-substituted
benzopyranobenzothiazepines showed moderate to comparable activity (using gatifloxin, natilmicin as ref. std.) against gram-pos. and
gram-neg. bacteria. They also showed antifungal activity (compared to fluconazole), with the compd. having the max. no. of MeO
groups having the max. activity, while the fluoro compds. are completely inactive.
Answer 137:
Simultaneous determination of flavonoid and alkaloid compounds in Citrus herbs by high-performance liquid
chromatography-photodiode array detection-electrospray mass spectrometry. Ding, Li; Luo, Xubiao; Tang, Fei; Yuan, Jinbin;
Liu, Qian; Yao, Shouzhuo. College of Chemistry and Chemical Engineering, Hunan University, Changsha, Peop. Rep. China.
Journal of Chromatography, B: Analytical Technologies in the Biomedical and Life Sciences (2007), 857(2), 202-209. Publisher:
Elsevier B.V., CODEN: JCBAAI ISSN: 1570-0232. Journal written in English. CAN 147:455781 AN 2007:1106828 CAPLUS
Abstract
The major active biol. constituents in Citrus herbs are flavonoids, esp. hesperidin, naringin and alkaloids, mainly synephrine, with
beneficial medical effects on human health. They are used as the markers to control the quality of Citrus herbs. In this paper, a new
ion pairing chromatog. method was developed to exclude the most polar solute (synephrine) from the viod vol. and to maintain
selectivity between the two other solutes (hesperidin and naringin). Perfluorinated carboxylic acids, which are appropriate for MS
detection due to their volatility, were used as ion-pairing agents. The problems of the synephrine sepn., such as band tailing and low
retention, were solved successfully by using perfluorinated carboxylic acids. The effect of heptafluorobutyric acid (HFBA) was the
best in the three investigated perfluorinated carboxylic acids. For the flavanone glycosides, the influence of the perfluorinated acids
on retention time was rather weak. The 2 different kinds of the analytes were sepd. satisfactorily in one run using an isocratic eluent
and the total anal. time takes less than 10 min. The abundance of pseudomol. ions was recorded using selected ion monitoring (SIM)
mode of m/z 135.1, 273.1 and 303.1 for synephrine, naringin and hesperidin, resp. The contents of hesperidin, naringin and synephrine
in several Citrus herbs were simultaneously detd. by the proposed method.
Answer 138:
Two novel antibacterial flavonoids from Myrsine africana L. Kang, Lu; Zhou, Jian-Xia; Shen, Zheng-Wu. School of Pharmacy,
Shanghai University of Traditional Chinese Medicine, Shanghai, Peop. Rep. China. Chinese Journal of Chemistry (2007), 25(9),
1323-1325. Publisher: Shanghai Institute of Organic Chemistry, CODEN: CJOCEV ISSN: 1001-604X. Journal written in English.
flavanone
Abstract
Two novel flavonoids, myrsininone A (1), an isoflavone and myrsininone B (2), a flavanone, with very strong antibacterial activities,
were isolated from the stems of Myrsine africana L. Their structures were elucidated by extensive spectroscopic analyses. The
antibacterial activities were detd. by modified Resazuric MIC methods.
Answer 139:
Application of liquiritigenin to manufacturing medicines for preventing and treating cancer. Cai, Yunqing. (Nanjing Medical
University, Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 10pp. CODEN: CNXXEV CN
101036638 A 20070919 Patent written in Chinese. Application: CN 1003-8887 20060316. Priority: . CAN 147:398635 AN

CN 101036638 A 20070919 CN 2006-10038887 20060316
CN 2006-10038887 20060316
Abstract
The patent relates to the application of liquiritigenin to manufg. the medicines for preventing and treating lung cancer, liver cancer,
gastric cancer, colon cancer, etc. Liquiritigenin is flavanone deriv.
Answer 140:
Antifungal derivatives from Piper mollicomum and P. lhotzkyanum (Piperaceae). Lago, Joao Henrique G.; Young, Maria
Claudia M.; Reigada, Juliana B.; Soares, Marisi G.; Roesler, Bianca P.; Kato, Massuo J. Centro de Ciencias e Humanidades,
Universidade Presbiteriana Mackenzie, Sao Paulo, Brazil. Quimica Nova (2007), 30(5), 1222-1224. Publisher: Sociedade Brasileira
de Quimica, CODEN: QUNODK ISSN: 0100-4042. Journal written in English. CAN 148:398405 AN 2007:1064504 CAPLUS
Abstract
Bio-guided fractionation of the exts. from leaves of Piper mollicomum and Piper lhotzkyanum against the fungi Cladosporium
cladosporioides and C. sphaerospermum afforded seven bioactive compds., four being chromenes: Me
2,2-dimethyl-2H-chromene-6-carboxylate, Me 8-hydroxy-2,2-dimethyl-2H-chromene-6-carboxylate,
2-methyl-2-[4'-methyl-3'-pentenyl]-2H-1-benzopyran-6-carboxylic acid, 2,2-dimethyl-2H-chromene-6-carboxylic acid, one a
dihydrochalcone: 2',6'-dihydroxy-4'-methoxydihydrochalcone, and two flavanones: 7-methoxy-5,4'-dihydroxy-flavanone and
7,4'-dimethoxy-5-hydroxy-flavanone. The structures of the bioactive isolated derivs. were elucidated by interpretation of their NMR
data [1H and 13C (BBD, DEPT 135°)], and mass spectral data as well as by comparison with data described in the literature.
flavanone
Answer 141:
Determination of the content of total flavone in cultivated Glycyrrhiza uralensis. Yan, Yonghong; Wang, Wenquan; Yang, Na.
School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, Peop. Rep. China. Zhongguo Zhongyao Zazhi
(2006), 31(12), 1019-1021. Publisher: Zhongguo Zhongyao Zazhishe, CODEN: ZZZAE3 ISSN: 1001-5302. Journal written in
Chinese. CAN 147:455760 AN 2007:1055108 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
The content of the content of total flavone in cultivated Glycyrrhiza uralensis was detd. by colorimetry by using character of
flavanone translated into chalcone under alk. condition of 10% KOH soln. The linear regression equation was Y = 21.323X-0.0923 (r =
0.9994), and the linear range was 4.9-98.0 μg/mL. The av. recovery was 98.7%, and RSD was 1.9% (n = 5). There was large
difference of the total flavone content from different localities, and the difference was not significant with different ages. The method
is sensitive, convenient, and accurate.
Answer 142:
Screening the genes associated with anthocyanin biosynthesis in roots of 'Tsuda' turnip using cDNA microarray. Xu,
Zhi-Ru; Li, Yu-Hua. Life Science College, Northeast Forestry University, Harbin, Peop. Rep. China. Yichuan (2006), 28(9),
1101-1106. Publisher: Kexue Chubanshe, CODEN: ICHUDW ISSN: 0253-9772. Journal written in Chinese. CAN 148:234049
Abstract
Anthocyanins are important secondary metabolites in plants, which are involved in many functions. The white peel of an enlarged root
in 'Tsuda' plants turned red after irradiated with UV-A light for 48h, but remained white when held in the dark. Red earthnuts and white
peels were hybridized with cDNA microarray made by unique gene fragments of subtraction library. The expression of 81 genes were
up-regulated including cytochrome P 450, PAL, F3H, ANS, CHS, DFR, and GST gene fragments related to anthocyanidin biosynthesis.
The expression of 47 genes was down-regulated after irradiated with UV-A light. The northern blotting results showed that the
expression of PAL, CHS, F3H, DFR, and ANS in red root peels was more in 'Tsuda' turnip after irradn. with UV-A light than in white
ones held in a dark condition. The results of northern blotting verified the reliability of cDNA microarray.
Answer 143:
Isopentenyl flavanone from Mallotus apelta. Wu, Gui-fan; Wei, Song; Lan, Shu-bin; Xu, Xue-jian. Department of Pharmacy,
Guangxi College of Traditional Chinese Medicine, Nanning, Peop. Rep. China. Zhongcaoyao (2006), 37(8), 1126-1128. Publisher:
Zhongcaoyao Zazhi Bianjibu, CODEN: CTYAD8 ISSN: 0253-2670. Journal written in Chinese. CAN 148:198232 AN
Abstract
To study the chem. constituents in the leaves of Mallotus apelta. Constituents isolation and purifn. were carried out on silica gel and
polyamide column. Their structures were identified by physicochem. properties and spectral anal. Five compds. were isolated and
flavanone
elucidated as taraxerol (I), β-sitosterol (II), 5,7-dihydroxy-6-isopentenyl-4'-methoxy-flavanone (III), apigenin (IV), and
apigenin-7-O-β-D-glucoside (V). Compd. III is a new compd. named as mallotusin. Compds. I and III-V are isolated from the leaves of
M. apelta for the first time.
Answer 144:
Estimation of daily human intake of food flavonoids. Mullie, P.; Clarys, P.; Deriemaeker, P.; Hebbelinck, M. Faculty of
Physical Education and Physiotherapy, Department of Human Biometry and Biomechanics, Vrije Universiteit Brussel (VUB),
Brussels, Belg. Plant Foods for Human Nutrition (New York, NY, United States) (2007), 62(3), 93-98. Publisher: Springer,
CODEN: PFHNE8 ISSN: 0921-9668. Journal written in English. CAN 148:167875 AN 2007:1027502 CAPLUS (Copyright (C)
Abstract
The daily intake of food flavonoids was detd. using a semiquant. food frequency questionnaire (FFQ) and a four day non consecutive
food diary (4DFR) in a group of 45 female Flemish dietitians. The subjects were asked to report their food intake three times: day 1
using the FFQ (FFQ1); between day 2 and 13 using a four day non consecutive food diary (4DFR); and again the FFQ on day 14
(FFQ2). The total flavonoid intake in mg/day as estd. with the different methods were resp. (mean and SD) for FFQ1 166.0 ± 146.6
mg/day; for 4DFR 203.0 ± 243.2 mg/day; and for FFQ2 158.3 ± 151.8 mg/day. There was a significant different est. for the amt. of
flavan-3-ols, flavanones and flavones when comparing the two FFQs with the 4DFR. The two research methods classified 88% of the
45 dietitians in the same or in an adjacent quartile for total flavonoid intake. The findings of this study indicate that the developed
FFQ seems to be a simple and reliable method to assign subjects in quartiles of flavonoid intake.
Answer 145:
Transcriptional control of anthocyanin biosynthetic genes in extreme phenotypes for berry pigmentation of naturally
occurring grapevines. Castellarin, Simone D.; Di Gaspero, Gabriele. Instituto di Genomica Applicata, Parco Scientifico e
Tecnologico Luigi Danieli, Udine, Italy. BMC Plant Biology (2007), 7 No pp. given. Publisher: BioMed Central Ltd., CODEN:
BPBMAN ISSN: 1471-2229. http://www.biomedcentral.com/content/pdf/1471-2229-7-46.pdf Journal; Online Computer File written in
Abstract
Background Fruit coloration of red-skinned grapevines is mainly due to anthocyanin pigments. We analyzed a panel of nine cultivars
that included extreme phenotypes for berry color, ranging from green (absence of anthocyanins) to red, purple, violet and blue.
Expression of six genes of the anthocyanin pathway coding for flavanone-hydroxylase (F3H), flavonoid 3'-hydroxylase (F3'H),
flavonoid 3',5'-hydroxylase (F3'5'H), UDP-glucose:flavonoid-3-O-glucosyltransferase (UFGT), glutathione-S-transferase (GST),
O-methyltransferase (OMT) and four transcription factors (MybA, MybB, MybC, MybD) was analyzed by quant. RT-PCR at four
developmental stages from before the onset of ripening until full maturity and compared to anthocyanin metabolites. Results Total
anthocyanin content at full maturity correlated well with the cumulative expression of F3H, UFGT and GST throughout ripening.
Transcripts of the last two genes were absent in the green-skinned cultivar 'Sauvignonasse', also known as 'Tocai friulano', and were at
least 10-fold less abundant in pale red cultivars, such as 'Pinot gris' and 'Gewurztraminer', compared to fully colored cultivars.
Predominance of tri-hydroxylated anthocyanins (delphinidin, petunidin and malvidin) in cultivars bearing dark berries with violet and blue
hue was assocd. with higher ratios of F3'5'H/F3'H transcription, compared to redskinned cultivars. Higher levels of OMT transcripts
were obsd. in berries of cultivars that accumulated methoxylated forms of anthocyanins more abundantly than non-methoxylated
forms. Conclusions Color variation of the grape berry conforms to a peculiar pattern of genotype-specific expression of the whole set
of anthocyanin genes in a direct transcript-metabolite-phenotype relationship. Cumulative mRNA levels of the structural genes and
flavanone
their relative abundance throughout ripening explained per se the final phenotype for anthocyanin content, anthocyanin compn., color
intensity and color hue of grapes at berry maturity.
Answer 146:
Novel exon combinations generated by alternative splicing of gene fragments mobilized by a CACTA transposon in Glycine
max. Zabala, Gracia; Vodkin, Lila. Department of Crop Sciences, University of Illinois, Urbana, IL, USA. BMC Plant Biology
(2007), 7 No pp. given. Publisher: BioMed Central Ltd., CODEN: BPBMAN ISSN: 1471-2229.
http://www.biomedcentral.com/content/pdf/1471-2229-7-38.pdf Journal; Online Computer File written in English. CAN 147:336888
Abstract
Background: The recent discoveries of transposable elements carrying host gene fragments such as the Pack-MULEs (Mutator-like
transposable elements) of maize (Zea mays), rice (Oryza sativa) and Arabidopsis thaliana, the Helitrons of maize and the Tgm-Express
of soybeans, revealed a widespread genetic mechanism with the potential to rearrange genomes and create novel chimeric genes
affecting genomic and proteomic diversity. Not much is known with regard to the mechanisms of gene fragment capture by those
transposon elements or the expression of the captured host gene fragments. There is some evidence that chimeric transcripts can be
assembled and exist in EST collections. Results: We report results obtained from anal. of RT-PCR derived cDNAs of the Glycine max
mutant flower color gene, wp, that contains a 5.7-kb transposon (Tgm-Express1) in Intron 2 of the flavanone 3-hydroxylase gene (F3H)
and is composed of five unrelated host gene fragments. The collection of cDNAs derived from the wp allele represents a multiplicity
of processed RNAs varying in length and sequence that includes some identical to the correctly processed mature F3H transcript with
three properly spliced exons. Surprisingly, the five gene fragments carried by the Tgm-Express1 were processed through complex
alternative splicing as addnl. exons of the wp transcript. Conclusion: The gene fragments carried by the Tgm inverted repeat ends
appear to be retained as functional exons/introns within the element. The spliceosomes then select indiscriminately the canonical intron
splice sites from a pre-mRNA to assemble diverse chimeric transcripts from the exons contained in the wp allele. The multiplicity and
randomness of these events provide some insights into the origin and mechanism of alternatively spliced genes.
Answer 147:
Brain function improvers containing flavanones and their compositions. Fukumoto, Shuichi; Okada, Miki; Uchida, Koji;
Shibata, Takahiro; Nakahara, Hiroko; Kita, Narumi; Yokogoshi, Hidehiko. (Pokka Corp., Japan). Jpn. Kokai Tokkyo Koho (2007),
12pp. CODEN: JKXXAF JP 2007230878 A 20070913 Patent written in Japanese. Application: JP 2006-51013 20060227.

JP 2007230878 A 20070913 JP 2006-51013 20060227
JP 2006-51013 20060227
Abstract
flavanone
Title improvers and compns., useful for beverages, foods, pharmaceuticals, or feeds, contain eriodictyol (I), hesperetin, naringenin,
eriocitrin and/or hesperidin as active ingredients. Thus, I at 15 μM enhanced NGF-induced neurite elongation in PC12 cells by 50.28%.
I at 1 mg/kg p.o. also improved scopolamine-induced learning disorder in rats.
Answer 148:
Mechanism of inhibition of human secretory phospholipase A2 by flavonoids: rationale for lead design. Laettig, Jens;
Boehl, Markus; Fischer, Petra; Tischer, Sandra; Tietboehl, Claudia; Menschikowski, Mario; Gutzeit, Herwig O.; Metz, Peter; Pisabarro, M.
Teresa. Structural Bioinformatics, BIOTEC TU Dresden, Dresden, Germany. Journal of Computer-Aided Molecular Design
(2007), 21(8), 473-483. Publisher: Springer, CODEN: JCADEQ ISSN: 0920-654X. Journal written in English. CAN 148:253340
Abstract
The human secretory phospholipase A2 group IIA (PLA2-IIA) is a lipolytic enzyme. Its inhibition leads to a decrease in eicosanoids
levels and, thereby, to reduced inflammation. Therefore, PLA2-IIA is of high pharmacol. interest in treatment of chronic diseases such
as asthma and rheumatoid arthritis. Quercetin and naringenin, amongst other flavonoids, are known for their anti-inflammatory activity
by modulation of enzymes of the arachidonic acid cascade. However, the mechanism by which flavonoids inhibit Phospholipase A2
(PLA2) remained unclear so far. Flavonoids are widely produced in plant tissues and, thereby, suitable targets for pharmaceutical
extns. and chem. syntheses. Our work focuses on understanding the binding modes of flavonoids to PLA2, their inhibition mechanism
and the rationale to modify them to obtain potent and specific inhibitors. Our computational and exptl. studies focused on a set of 24
compds. including natural flavonoids and naringenin-based derivs. Exptl. results on PLA2-inhibition showed good inhibitory activity for
quercetin, kaempferol, and galangin, but relatively poor for naringenin. Several naringenin derivs. were synthesized and tested for
affinity and inhibitory activity improvement. 6-(1,1-dimethylallyl)naringenin revealed comparable PLA2 inhibition to quercetin-like
compds. We characterized the binding mode of these compds. and the determinants for their affinity, selectivity, and inhibitory
potency. Based on our results, we suggest C(6) as the most promising position of the flavonoid scaffold to introduce chem.
modifications to improve affinity, selectivity, and inhibition of PLA2-IIA by flavonoids.
Answer 149:
Flavonoids inhibit breast cancer resistance protein-mediated drug resistance: transporter specificity and structure-activity
relationship. Katayama, Kazuhiro; Masuyama, Kazuto; Yoshioka, Sho; Hasegawa, Hitomi; Mitsuhashi, Junko; Sugimoto,
Yoshikazu. Department of Chemotherapy, Kyoritsu University of Pharmacy, Tokyo, Japan. Cancer Chemotherapy and
Pharmacology (2007), 60(6), 789-797. Publisher: Springer, CODEN: CCPHDZ ISSN: 0344-5704. Journal written in English. CAN
Abstract
Purpose: ATP-binding cassette (ABC) transporters, such as P-glycoprotein (P-gp), breast cancer resistance protein (BCRP), and
multidrug resistance-related protein 1 (MRP1), confer resistance to various anticancer agents. We previously reported that some
flavonoids have BCRP-inhibitory activity. Here we show the reversal effects of an extensive panel of flavonoids upon BCRP-, P-gp-,
and MRP1-mediated drug resistance. Methods: Reversal effects of flavonoids upon BCRP-, P-gp-, or MRP1-mediated drug resistance
were examd. in the BCRP- or MDR1-transduced human leukemia K562 cells or in the MRP1-transfected human epidermoid carcinoma
KB-3-1 cells using cell growth inhibition assays. The IC50 values were detd. from the growth inhibition curves. The RI50 values were
then detd. as the concn. of inhibitor that causes a twofold redn. of the IC50 in each transfectant. The reversal of BCRP activity was
tested by measuring the fluorescence of intracellular topotecan. Results: The BCRP-inhibitory activity of 32 compds. was screened,
and 20 were found to be active. Among these active compds., 3',4',7-trimethoxyflavone showed the strongest anti-BCRP activity with
flavanone
RI50 values of 0.012 μM for SN-38 and 0.044 μM for mitoxantrone. We next examd. the effects of a panel of 11 compds. on P-gp-
and MRP1-mediated drug resistance. Two of the flavones, 3',4',7-trimethoxyflavone and acacetin, showed only low anti-P-gp activity,
with the remainder displaying no suppressive effects against P-gp. None of the flavonoids that we tested inhibited MRP1.
Conclusion: Our present results thus indicate that many flavonoids selectively inhibit BCRP only. Moreover, we examd. the
structure-BCRP inhibitory activity relationship from our current study.
Answer 150:
Effects of Isoflavones and Soybeans Fermented with Bacillus subtilis on Lipopolysaccharide-Induced Production of Tumor
Necrosis Factor-α and Fibrinolysis In Vivo. Hasumuma, Ryoichi; Kawaguchi, Kiichiro; Kikuchi, Sei-ichi; Sugiyama, Tsuyoshi;
Kumazawa, Yoshio. Department of Biosciences, School of Science and Graduate School of Fundamental Life Science, Kitasato
University, Sagamihara, Japan. Immunopharmacology and Immunotoxicology (2007), 29(2), 323-333. Publisher: Informa
Healthcare, CODEN: IITOEF ISSN: 0892-3973. Journal written in English. CAN 148:159402 AN 2007:1012408 CAPLUS
Abstract
The effects of isoflavones and of a deriv. of soybeans fermented with Bacillus subtilis, designated Nattoesse, on the
lipopolysaccharide (LPS)-induced prodn. of tumor necrosis factor-α (TNF-α) and fibrinolysis were investigated in vivo. The dietary
supplement Nattoesse contains several isoflavones. Therefore, we examd. the effects of individual isoflavones (daidzein, daidzin,
genistein, and genistin) on the LPS-induced prodn. of TNF-α. I.p. injections of daidzein, daidzin, and genistin (but not of genistein
before a challenge with LPS) resulted in significant depression of serum levels of TNF-α in mice. Daidzein had the strongest activity
in this assay. Oral administration of daidzein to mice also had a significant suppressive effect, as compared with that of the Citrus
flavanone naringin. In galactosamine-sensitized mice, by contrast, the suppression of LPS-induced lethal shock by daidzein was very
weak. Nattoesse did not inhibit the prodn. of TNF-α nor did it prevent lethal shock. However, oral administration of Nattoesse to mice
significantly suppressed LPS-induced increases in scores of the fibrin degrdn. product, and the effect was both dose- and
time-dependent. Thus, it appears that Nattoesse has fibrinolytic activity during LPS-induced circulatory failure.
Answer 151:
Maize Lc transcription factor enhances biosynthesis of anthocyanins, distinct proanthocyanidins and phenylpropanoids in
apple (Malus domestica Borkh.). Li, Houhua; Flachowsky, Henryk; Fischer, Thilo C.; Hanke, Magda-Viola; Forkmann, Gert;
Treutter, Dieter; Schwab, Wilfried; Hoffmann, Thomas; Szankowski, Iris. Institute of Biological Production Systems, Fruit Science
Section, Leibniz University of Hannover, Hannover, Germany. Planta (2007), 226(5), 1243-1254. Publisher: Springer, CODEN:
PLANAB ISSN: 0032-0935. Journal written in English. CAN 148:74166 AN 2007:1010348 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Flavonoids are a large family of polyphenolic compds. with manifold functions in plants. Present in a wide range of vegetables and
fruits, flavonoids form an integral part of the human diet and confer multiple health benefits. Here, the authors report on metabolic
engineering of the flavonoid biosynthetic pathways in apple (Malus domestica Borkh.) by overexpression of the maize (Zea mays L.)
leaf color (Lc) regulatory gene. The Lc gene was transferred into the M. domestica cultivar Holsteiner Cox via Agrobacterium
tumefaciens-mediated transformation which resulted in enhanced anthocyanin accumulation in regenerated shoots. Five independent
Lc lines were investigated for integration of Lc into the plant genome by Southern blot and PCR analyses. The Lc-transgenic lines
contained one or two Lc gene copies and showed increased mRNA levels for phenylalanine ammonia-lyase (PAL), chalcone synthase
(CHS), flavanone 3 beta-hydroxylase (FHT), dihydroflavonol 4-reductase (DFR), leucoanthocyanidin reductases (LAR), anthocyanidin
flavanone
synthase (ANS) and anthocyanidin reductase (ANR). HPLC-DAD and LC-MS analyses revealed higher levels of the anthocyanin
idaein (12-fold), the flavan 3-ol epicatechin (14-fold), and esp. the isomeric catechin (41-fold), and some distinct dimeric
proanthocyanidins (7 to 134-fold) in leaf tissues of Lc-transgenic lines. The levels of phenylpropanoids and their derivs. were only
slightly increased. Thus, Lc overexpression in Malus domestica resulted in enhanced biosynthesis of specific flavonoid classes, which
play important roles in both phytopathol. and human health.
Answer 152:
Effects of the chemically synthesized flavanone 7-(O-prenyl)naringenin-4'-acetate on the estrogen signaling pathway in vivo
and in vitro. Kretzschmar, Georg; Vollmer, Guenter; Schwab, Pia; Tischer, Sandra; Metz, Peter; Zierau, Oliver. Institut fuer
Zoologie, Technische Universitaet Dresden, Dresden, Germany. Journal of Steroid Biochemistry and Molecular Biology (2007),
107(1-2), 114-119. Publisher: Elsevier Ltd., CODEN: JSBBEZ ISSN: 0960-0760. Journal written in English. CAN 148:1267 AN
Abstract
The flavanone naringenin is known to possess only weak estrogenic properties, but some of its derivs. such as 8-prenylnaringenin are
potent phytoestrogens. The aim of this study was to further clarify structure-function relationships of flavanones regarding their
estrogenic or antiestrogenic properties by characterizing the new chem. synthesized naringenin deriv. 7-(O-prenyl)naringenin-4'-acetate
(7-O-PN). A yeast based reporter gene assay and MVLN cells, a MCF-7-derived cell line that possesses a luciferase reporter gene
under the control of a vitellogenin estrogen responsive element, were used to investigate estrogenic actions of 7-O-PN in vitro.
Estradiol (E2) has been used as a pos. control. Subsequently a 3-day rat uterotrophic assay was performed to test for estrogenic
effects. In addn., mRNA expression of estrogen-sensitive genes in the uteri of these rats was measured using real time rtPCR.
While E2 leads to a strong dose-dependent signal in the yeast based reporter gene assay and in MVLN cells, 7-O-PN shows mild E2
antagonistic properties at concns. 10-8 and 10-7 M, E2 agonistic properties at 10-6 and 10-5 M in MVLN cells and no effects on the
yeast based system. In contrast to E2 treatment, 7-O-PN treatment did not increase uterus wet wt. compared to the neg. control.
These findings are supported by mRNA expression studies of proliferation markers. Addnl., mRNA expression studies of
estrogen-regulated genes revealed very strong antiestrogenic properties of 7-O-PN regarding regulation of complement C3 expression
while some estrogenic effects could be obsd. on the expression of estrogen receptor β, clusterin and possibly on progesterone receptor
and vascular endothelial growth factor.
Answer 153:
Inhibition of the formation of the neurotoxin 5-S-cysteinyl-dopamine by polyphenols. Vauzour, David; Vafeiadou, Katerina;
Spencer, Jeremy P. E. Molecular Nutrition Group, School of Chemistry, Food and Pharmacy, University of Reading, Reading, UK.
Biochemical and Biophysical Research Communications (2007), 362(2), 340-346. Publisher: Elsevier, CODEN: BBRCA9 ISSN:
0006-291X. Journal written in English. CAN 147:336135 AN 2007:996490 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
The death of nigral neurons in Parkinson's disease is thought to involve the formation of the endogenous neurotoxin,
5-S-cysteinyl-dopamine. In the present study, we show that the polyphenols, (+)-catechin and caffeic acid, which contain a catechol
moiety, inhibit tyrosinase-induced formation of 5-S-cysteinyl-dopamine via their capacity to undergo tyrosinase-induced oxidn. to yield
cysteinyl-polyphenol adducts. In contrast, the inhibition afforded by the flavanone, hesperetin, was not accompanied by the formation
of cysteinyl-hesperetin adducts, indicating that it may inhibit via direct interaction with tyrosinase. While the stilbene resveratrol also
inhibited 5-S-cysteinyl-dopamine formation, this was accompanied by the formation of dihydrobenzothiazine, a strong neurotoxin. Our
data indicate that the inhibitory effects of polyphenols against 5-S-cysteinyl-dopamine formation are structure-dependent and shed
flavanone
further light on the mechanisms by which polyphenols exert protection against neuronal injury relevant to neurodegenerative diseases.
Answer 154:
Juice components and antioxidant capacity of citrus varieties cultivated in China. Xu, Guihua; Liu, Donghong; Chen, Jianchu;
Ye, Xingqian; Ma, Yaqin; Shi, John. Department of Food Science and Nutrition, Zhejiang University, Hangzhou, Peop. Rep. China.
Food Chemistry (2007), Volume Date 2008, 106(2), 545-551. Publisher: Elsevier B.V., CODEN: FOCHDJ ISSN: 0308-8146.
Abstract
Juices from fifteen citrus varieties (seven mandarins, four sweet oranges, one lemon, one grapefruit, and two pummeloes) of China
were investigated mainly on quality parameters, total carotenoid, phenolic compds. (total phenolics, flavanone glycosides (FGs), and
phenolic acids), and antioxidant capacity (ferric reducing antioxidant power (FRAP) assay and 2,2-diphenyl-1-picrylhydrazyl (DPPH)
assay). Among the fifteen varieties, Bendizao had the highest content of total carotenoid (10.02 mg/L), Satsuma had the highest
content of narirutin (288.12 mg/L), Yinzaocheng had the highest content of hesperidin (533.64 mg/L), and Huyou had the highest
content of naringin (348.53 mg/L), neohesperidin (265.25 mg/L) and total FGs (746.08 mg/L). As for total phenolic acids, Liubencheng
had the highest content (72.61 mg/L). Hybrid 439 achieved the highest AA content (631.25 mg/L), and the highest total phenolics
(1555.49 mg/L) and the greatest inhibition of DPPH radical (61.62%). Hamlin had the highest ascorbic acid equiv. antioxidant capacity
(AEAC: 899.31 mg/L) detd. by FRAP assay. Correlation coeffs. of AA, total phenolics (gallic acid equiv.), FRAP (AEAC), DPPH (I%),
total FGs and total phenolic acids indicated that AA played a major role for the antioxidant capacity of citrus juices, and phenolics also
played an important role, which may be mainly ascribed to FGs, while phenolic acids seemed to play a minimal role. Furthermore,
Huyou and Hybrid 439 were considered two valuable varieties from the view of antioxidant capacity and nutrition.
Answer 155:
Ultrasonic extraction and identification of total flavanone from longan leaves. Lu, Hai-feng; Zhao, Jin; Li, Lin; Huang, Suo-yi;
Li, Wei-bin; Yang, Wen-hui. Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Peop. Rep. China.
Weiliang Yuansu Yu Jiankang Yanjiu (2007), 24(4), 48-49. Publisher: Weiliang Yuansu Yu Jiankang Yanjiu Zazhishe, CODEN:
WYYJAF ISSN: 1005-5320. Journal written in Chinese. CAN 147:405063 AN 2007:967923 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Aim: In order to make use of the resources of longan leaves, avoid wasting and approach the extn. of total flavanone of longan
leaves. Methods: The flavonoids were extd. from longan leaves by ultrasonic wave with ethanol as the solvent. Using
spectrophotometry to ext. and check the flavanone of longan leaves. Results: By this method, the obtained total flavanone of longan
leaves is 1.0571 mg/mL and the rate of recovery is 101.3%. Conclusion: This method is a purely phys. process and has not any
pollution, and it is an ideal way to ext. the flavanone of longan leaves.
Answer 156:
Purification and determination of flavonoids in Radix Glycyrrhizae. Li, Jun-song; Xu, De-sheng; Feng, Yi; Chen, Li-hua.
Shanghai University of Traditional Chinese Medicine, Shanghai, Peop. Rep. China. Zhongchengyao (2007), 29(7), 997-1000.
flavanone
Publisher: Guojia Shipin Yaopin Jiandu Guanliju, Xinxi Zhongxin Zhongchengyao Xinxizhan, CODEN: ZHONBS ISSN: 1001-1528.
Abstract
The colorimetric method for detn. of flavonoids in Radix Glycyrrhizae was established and the purifn. process of flavonoids was
studied. The principle of colorimetric method was that flavanone could be converted into chalcone in alk. condition. The purifn.
process of was optimized by using polyamide with the amt. of naringin as ref. substance and index. The purifn. process was as
followed: the ratio of Radix Glycyrrhizae to polyamide was 2:1 (g/g), the ratio of diam. to height of column was 1:7, 5 times bed vol. of
70% ethanol was used, the eluted rate of flavonoids was 90%, and the av. recovery rate of flavonoids was 98.81% with RSD of
2.00%. The amt. of flavonoids in total solids was 45%.
Answer 157:
Separation mechanism and determination of flavanones with capillary electrophoresis and high-performance liquid
chromatography. Wang, Shu-Ping; Fu, Ming-Dung; Wang, Mi-Hung. Department of Applied Chemistry, Providence University,
Taichung Hsein, Taiwan. Journal of Chromatography, A (2007), 1164(1-2), 306-312. Publisher: Elsevier B.V., CODEN: JCRAEY
SciFinder (R))
Abstract
To probe sepn. mechanism and detn. with capillary zone electrophoresis (CZE) and liq. chromatog. (LC), nine compds. with identical
flavanone skeleton were studied. Optimum sepn. of LC was attained with gradient of acetonitrile and 5 mM phosphate buffer (pH 6.9).
For CE, electrolyte buffer was 4.5 mM SDS in 32 mM sodium tetraborate buffer (pH 9.2). The distinguishing feature in this work was
successful sepn. of monohydroxyl stereoisomers by CZE. Polarity is generally increased with hydroxyl groups. In a sepn.
mechanism study, polarity would be reduced by intramol. hydrogen bond between hydroxyl of C5 and carbonyl group of C4.
Comparison of the retention results among monohydroxyl flavanones shows polarity with hydroxyl at C6 the least, and that at C4' and
C7 nearly equal. Also, elution order of flavones and flavanones would be adverse due to the hydroxyl at C3 in LC. From the
numerical value pKa of flavanone, the C7-OH is the smallest, and two hydroxyl groups in an adjacent position is always less than the
unique one caused by forming a stable 5-membered ring. Investigation of sepn. mechanism yield only the effect of constituent but
also reasonable explanation for contradictory results between L. W. Wulf and C. W. Nagel (1976) and the authors' lab., this due to the
hydroxyl at C3.
Answer 158:
Antiproliferative activity of Citrus juices and HPLC evaluation of their flavonoid composition. Camarda, Lorenzo; Di
Stefano, Vita; Del Bosco, Sergio Fatta; Schillaci, Domenico. Dipartimento di Chimica e Tecnologie Farmaceutiche, Universita degli
Studi di Palermo, Palermo, Italy. Fitoterapia (2007), 78(6), 426-429. Publisher: Elsevier B.V., CODEN: FTRPAE ISSN:
Abstract
The antiproliferative activity of fresh fruit juices extd. from Citrus sinensis (cv. Washington Navel and cv. Sanguinello), C. deliciosa
cv. Avana, C. clementina cv. Nules, C. aurantium subsp. myrtifolia , was evaluated against K562 (human chronic myelogenous
leukemia), HL-60 (human leukemia) and MCF-7 (human breast adenocarcinoma) cell lines. All the juices tested showed antiproliferative
flavanone
activity. Moreover, the pattern of the main flavanone compds. in the juices has been detd. by HPLC anal.
Answer 159:
Characterization of major enzymes and genes involved in flavonoid and proanthocyanidin biosynthesis during fruit
development in strawberry (Fragaria × ananassa). Almeida, Joao R. M.; D'Amico, Eleonora; Preuss, Anja; Carbone, Fabrizio; de
Vos, C. H. Ric; Deiml, Bettina; Mourgues, Fabienne; Perrotta, Gaetano; Fischer, Thilo C.; Bovy, Arnaud G.; Martens, Stefan; Rosati,
Carlo. Department of Genetics and Genomics, Trisaia Research Center, ENEA, Rotondella, Italy. Archives of Biochemistry and
Biophysics (2007), 465(1), 61-71. Publisher: Elsevier, CODEN: ABBIA4 ISSN: 0003-9861. Journal written in English. CAN
Abstract
The biosynthesis of flavonoids and proanthocyanidins was studied in cultivated strawberry (Fragaria × ananassa) by combining
biochem. and mol. approaches. Chem. analyses showed that ripe strawberries accumulate high amts. of pelargonidin-derived
anthocyanins, and a larger pool of 3',4'-hydroxylated proanthocyanidins. Activities and properties of major recombinant enzymes were
demonstrated by means of in vitro assays, with special emphasis on specificity for the biol. relevant 4'- and 3',4'-hydroxylated
compds. Only leucoanthocyanidin reductase showed a strict specificity for the 3',4'-hydroxylated leucocyanidin, while other enzymes
accepted either hydroxylated substrate with different relative activity rates. The structure of late flavonoid pathway genes, leading to
the synthesis of major compds. in ripe fruits, was elucidated. Complex developmental and spatial expression patterns were shown for
phenylpropanoid and flavonoid genes in fruits throughout ripening as well as in leaves, petals and roots. Presented results elucidate
key steps in the biosynthesis of strawberry flavonoid end products.
Answer 160:
External preparation for skin containing flavanone derivative. Kida, Naoko; Tada, Akihiro; Kanamaru, Akiko. (Pola Chemical
Industries Inc., Japan). PCT Int. Appl. (2007), 51pp. CODEN: PIXXD2 WO 2007094384 A1 20070823 Designated States W:
AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI,
GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA,
MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY,
TJ, TM, TN, TR, TT, TZ, UA, UG. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT,
SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in Japanese. Application: WO 2007-JP52672
20070215. Priority: JP 2006-37647 20060215; JP 2006-181185 20060630; JP 2006-181186 20060630; JP 2006-195034 20060718.

WO 2007094384 A1 20070823 WO 2007-JP52672 20070215
DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM,
KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG,
flavanone
JP 2006-37647 A 20060215
JP 2006-181185 A 20060630
JP 2006-181186 A 20060630
JP 2006-195034 A 20060718
Abstract
To increase a tissue regeneration ability of a living body such as a collagen prodn. ability of fibroblast in the dermis in a skin defect
area typified by a large wrinkle or wound, a flavanone deriv. such as farrerol is used as an active ingredient of an external prepn. for
skin. Further, to efficiently screen a substance having an excellent effect on promoting wound healing, the remodeling action of
collagen fiber bundle is tested by using a skin wound model.
Answer 161:
Characterization of flavonoids in the extract of Sophora flavescens Ait. by high-performance liquid chromatography coupled
with diode-array detector and electrospray ionization mass spectrometry. Zhang, Lei; Xu, Liang; Xiao, Shan-Shan; Liao,
Qiong-Feng; Li, Qing; Liang, Jian; Chen, Xiao-Hui; Bi, Kai-Shun. Laboratory of Pharmaceutical Analysis, School of Pharmacy,
Shenyang Pharmaceutical University, Liaoning, Peop. Rep. China. Journal of Pharmaceutical and Biomedical Analysis (2007),
44(5), 1019-1028. Publisher: Elsevier B.V., CODEN: JPBADA ISSN: 0731-7085. Journal written in English. CAN 147:455734
Abstract
A method coupling high-performance liq. chromatog. (HPLC) with diode-array detector (DAD) and electrospray ionization mass
spectrometry (ESI) was established for the sepn. and characterization of flavonoids in Sophora flavescens Ait. Based on the
chromatog. sepn. of most flavonoids present in S. flavescens Ait., a total of 24 flavonoids were identified. Fourteen compds. were
unambiguously identified comparing exptl. data for retention time (t R), UV and MS spectra with those of the authentic compds.:
3',7-dihydroxy-4'-methoxy-isoflavone, trifolirhizin, kurarinol, formononetin, 7,4'-dihydroxy-5-methoxy-8-(γ,γ-dimethylallyl)-flavanone,
maackiain, isoxanthohumol, kuraridine, kuraridinol, sophoraflavanone G, xanthohumol, isokurarinone, kurarinone and kushenol D, and
addnl. 10 compds. were tentatively identified as kushenol O, trifolirhizin-6''-malonate, sophoraisoflavanone A (20), norkurarinol/kosamol
Q, kushenol I/N, kushenol C, 2'-methoxykurarinone, kosamol R, kushecarpin A and kushenol A by comparing exptl. data for UV and
MS spectra with those of literature. Furthermore, fragmentation pathways in pos. ions mode of 24 flavonoid compds. of types of
flavanone, flavanonol, flavonol, chalcone, isoflavone, isoflavanone and ptercocarpane were summarized. Some common features,
such as CH3⋅, H2O, CO, CO2, C3O2 and C2H2O losses, together with Retro-Diels-Alder fragmentations were obsd. in the prenylated
flavonoids in S. flavescens Ait. The loss of the lanandulyl chain was their characteristic fragmentation, which might help deducing the
structure of unknown flavonoid compds. The present study provided an approach to rapidly characterize bioactive constituents in S.
flavescens Ait.
Answer 162:
Extraction of total flavanones from Herba Plantaginis and its identification by ultrasonic wave. Huang, Suoyi; Zhang,
flavanone
Jingxuan; Cheng, Hui; Li, Rong. Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Wenben Province,
SGGHAL ISSN: 1008-0805. Journal written in Chinese. CAN 148:61455 AN 2007:916987 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
The methods for extn. and identification of total flavanones of Herba Plantaginis were investigated to explore the use of Plantago
resources. The flavonoids were extd. by ethanol as the solvent from Herba Plantaginis with ultrasonic wave extn. and detected by
using spectrophotometry. By this method, the content of the total flavanones of Herba Plantaginis was 1.24%, and the av. recovery
was 103%. The purity of the flavanones was very high. This method was a purely phys. process, and was an ideal way to ext. the
flavanones of Herba Plantaginis.
Answer 163:
Cudraflavanone A purified from Cudrania tricuspidata induces apoptotic cell death of human leukemia U937 cells, at least in
part, through the inhibition of DNA topoisomerase I and protein kinase C activity. Rho, Youn-Hwa; Lee, Byong-Won; Park,
Ki-Hun; Bae, Young-Seuk. Department of Biochemistry, College of Natural Sciences, Kyungpook National University, Taegu, S.
Korea. Anti-Cancer Drugs (2007), 18(9), 1023-1028. Publisher: Lippincott Williams & Wilkins, CODEN: ANTDEV ISSN:
Abstract
A chloroform ext. of the root bark of Cudrania tricuspidata showed an inhibitory effect on mammalian DNA topoisomerase I. The
topoisomerase I inhibitory compd. was purified and identified as 2S-2',5,7-trihydroxy-4',5'-(2,2-dimethylchromeno)-6-prenyl flavanone
(cudraflavanone A). Cudraflavanone A was shown to inhibit the activity of topoisomerase I with approx. 0.4 mmol/L 50% inhibitory
concn. A concn. of 6 μmol/L cudraflavanone A caused a 50% growth inhibition of human cancer cell U937. Cudraflavanone A-induced
cell death was characterized by the cleavage of poly(ADP-ribose) polymerase and pro-caspase-3. Furthermore, cudraflavanone A
induced the fragmentation of DNA into multiples of 180 bp (an apoptotic DNA ladder), indicating that the inhibitor triggered apoptosis.
This induction of apoptosis by cudraflavanone A was also confirmed using flow-cytometry anal. In addn., this compd. inhibited protein
kinase C activity with approx. 150 μmol/L 50% inhibitory concn. Taken together, these results suggest that cudraflavanone A may
function by inhibiting oncogenic disease, at least in part, through the inhibition of protein kinase C and topoisomerase I activity.
Answer 164:
Control of Mycosphaerella graminicola on wheat seedlings by medical drugs known to modulate the activity of ATP-binding
cassette transporters. Roohparvar, Ramin; Huser, Aurelie; Zwiers, Lute-Harm; De Waard, Maarten A. Laboratory of
Phytopathology, Wageningen University, Wageningen, Neth. Applied and Environmental Microbiology (2007), 73(15), 5011-5019.
Publisher: American Society for Microbiology, CODEN: AEMIDF ISSN: 0099-2240. Journal written in English. CAN 147:401569
Abstract
Medical drugs known to modulate the activity of human ATP-binding cassette (ABC) transporter proteins (modulators) were tested for
the ability to potentiate the activity of the azole fungicide cyproconazole against in vitro growth of Mycosphaerella graminicola and to
control disease development due to this pathogen on wheat seedlings. In vitro modulation of cyproconazole activity could be
flavanone
demonstrated in paper disk bioassays. Some of the active modulators (amitriptyline, flavanone, and phenothiazines) increased the
accumulation of cyproconazole in M. graminicola, suggesting that they reversed cyproconazole efflux. However, synergism between
cyproconazole and modulators against M. graminicola on wheat seedlings could not be shown. Despite their low in vitro toxicity to M.
graminicola, some modulators (amitriptyline, loperamide, and promazine) did show significant intrinsic disease control activity in
preventive and curative foliar spray tests with wheat seedlings. The results suggest that these compds. have indirect disease control
activity based on modulation of fungal ABC transporters essential for virulence and constitute a new class of disease control agents.
Answer 165:
Flavonoid genes of pear (Pyrus communis). Fischer, Thilo C.; Gosch, Christian; Pfeiffer, Judith; Halbwirth, Heidrun; Halle,
Christian; Stich, Karl; Forkmann, Gert. Lehrstuhl fuer Zierpflanzenbau und Gartenbauliche Pflanzenzuechtung, Department fuer
Pflanzenwissenschaften, Technische Universitaet Muenchen Weihenstephan, Freising, Germany. Trees (Heidelberg, Germany)
(2007), 21(5), 521-529. Publisher: Springer, CODEN: TRESEY ISSN: 0931-1890. Journal written in English. CAN 148:234148
Abstract
Pear (Pyrus sp.) is a major fruit crop of temperate regions with increasing extent of cultivation. Pear flavonoids contribute to its fruit
color, pathogen defense, and are health beneficial ingredients of the fruits. Comparative Southern analyses with apple (Malus x
domestica) cDNAs showed comparable genomic organization of flavonoid genes of both related genera. A homol.-based cloning
approach was used to obtain the cDNAs of most enzymes of the main flavonoid pathway of Pyrus: phenylalanine ammonia lyase,
chalcone synthase, chalcone isomerase, flavanone 3β-hydroxylase, flavonol synthase, dihydroflavonol 4-reductase,
leucoanthocyanidin reductase 1 and 2, anthocyanidin synthase, anthocyanidin reductase, and UDP-glucose : flavonoid
7-O-glucosyltransferase. The substrate specificities of the recombinant enzymes expressed in yeast were detd. for physiol. and
non-physiol. substrates and found to be in general agreement with the characteristic pear flavonoid metabolite pattern of mainly B-ring
dihydroxylated anthocyanins, flavonols, catechins, and flavanones. Furthermore, significant differences in substrate specificities and
gene copy nos. in comparison to Malus were identified. Cloning of the cDNAs and studying the enzymes of the Pyrus flavonoid
pathway is an essential task toward a comprehensive knowledge of Pyrus polyphenol metab. It also elucidates evolutionary patterns
of flavonoid/polyphenol pathways in the Rosaceae, which allocate several important crop plants.
Answer 166:
Flavanone glycosides from Mabea fistulifera Mart. (Euphorbiaceae). Coqueiro, Aline; Sarragiotto, Maria Helena; Zocoler, Marcos
Alberto; Vidotti, Gentil Jose. Departamento, de Quimica, Universidade Estadual de Maringa, Parana, Brazil. Biochemical
Systematics and Ecology (2007), 35(10), 717-719. Publisher: Elsevier Ltd., CODEN: BSECBU ISSN: 0305-1978. Journal written
Abstract
Four flavanone glycosides were purified from seeds of Mabea fistulifera. Their chemotaxonomic significance is discussed.
Answer 167:
Identification of flavonoid glycosides using metal complexation and tandem mass spectrometry. Davis, Barry D.; Pikulski,
flavanone
Michael; Zhang, Junmei; Needs, Paul W.; Kroon, Paul A.; Brodbelt, Jennifer S. Department of Chemistry and Biochemistry, The
University of Texas at Austin, Austin, TX, USA. Abstracts of Papers, 234th ACS National Meeting, Boston, MA, United States,
August 19-23, 2007 (2007), AGFD-008. Publisher: American Chemical Society, Washington, D. C CODEN: 69JNR2 Conference;
Meeting Abstract; Computer Optical Disk written in English. AN 2007:877848 CAPLUS (Copyright (C) 2008 ACS on SciFinder
(R))
Abstract
The precise identification of flavonoid glycosides using mass spectrometry is a challenging task. The glycosidic portions are a
particular challenge due to structural isomerism and multiple possible glycosylation sites. Simple metal complexation techniques have
been developed which provide this information when used in combination with tandem mass spectrometry. In this way, isomeric
compds. that usually yield identical fragmentation patterns are readily differentiated. The fragmentation patterns of the metal
complexes are consistent for particular structural motifs, expanding the range of this identification technique to a large no. of mols.
Metal complexation can be adapted to LCMS methods to provide structural information for reversed-phase liq. chromatog. sepns. The
method has been proven applicable to the flavonol, flavone and flavanone classes.
Answer 168:
Generation of variants of pharmacophore compounds using combinations of catalytic domains of enzymes involved in
secondary metabolite biosynthesis. Evans, Glen A.; Finlayson, Malcolm. (Pharmagic, Inc., USA). PCT Int. Appl. (2007),
66pp., which. CODEN: PIXXD2 WO 2007089382 A2 20070809 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG,
BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU,
ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA,
NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG.
Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM,
GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2007-US130 20070103. Priority: US 2006-755758
20060103; US 2006-787343 20060329. CAN 147:250561 AN 2007:874236 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))

WO 2007089382 A2 20070809 WO 2007-US130 20070103
US 2006-755758P P 20060103
US 2006-787343P P 20060329
Abstract
flavanone
Methods of generating variants natural compds. contg. pharmacophores are described. The method involves generating new
combinations of the catalytic moieties of enzymes assocd. with the biosynthesis of related compds. in a suitable host for
biosynthesis. The genes for these enzymes can be ordered, e.g. on a single vector, or on sep. vectors to allow randomization of the
order of reaction. Depending upon the nature and order of the catalytic domains and the precursors fed to the host, new variants of a
pharmacophore-contg. compd. can be generated.
Answer 169:
Silibinin inhibits constitutive activation of Stat3, and causes caspase activation and apoptotic death of human prostate
carcinoma DU145 cells. Agarwal, Chapla; Tyagi, Alpna; Kaur, Manjinder; Agarwal, Rajesh. Department of Pharmaceutical
Sciences, School of Pharmacy, University of Colorado Health Science Center, Denver, CO, USA. Carcinogenesis (2007), 28(7),
1463-1470. Publisher: Oxford University Press, CODEN: CRNGDP ISSN: 0143-3334. Journal written in English. CAN 147:203249
Abstract
Transcription factor signal transducer and activator of transcription (Stat)-3 is activated constitutively in prostate cancer (PCA)
suggesting that its disruption could be an effective approach to control this malignancy. Here we assessed whether silibinin, a
flavanone from Silybum marianum with proven anticancer efficacy in various cancer models, inhibits Stat3 activation in DU145 cells,
and if it does, what is the biol. fate of the cells. At 50 μM or higher concns. for 24 or 48 h, silibinin concn. dependently reduced
constitutive Stat3 phosphorylation at Tyr705 and Ser727 residues under both serum and serum-starved conditions. Constitutively
active Stat3-DNA binding was also inhibited concn. dependently by silibinin; however, apoptotic death together with caspase and
poly(ADP-ribose) polymerase (PARP) cleavage was obsd. by silibinin only under serum-starved conditions suggesting that addnl.
survival pathways are active under serum conditions. In other studies, cells were treated with various specific pharmacol. inhibitors
where phosphorylation of Stat3 was not reduced by epidermal growth factor receptor and Mitogen activated protein/extracellular signal
regulate kinase kinase (MEK1/2) inhibitors, suggesting lack of significant roles of these in Stat3 activation in DU145 cells. Janus
kinase (JAK)-1 and JAK2 inhibitors strongly reduced Stat3 phosphorylation but did not result in apoptotic cell death. Interestingly, JAK1
inhibitor only in combination with silibinin resulted in a complete redn. in Stat3 phosphorylation at Tyr705, activated caspase-9 and
caspase-3, and caused strong PARP cleavage and apoptotic death of DU145 cells. Given a crit. role of Stat3 activation in PCA, our
results showed that silibinin inhibits constitutively active Stat3 and induces apoptosis in DU145 cells, and thus might have potential
significance in therapeutic intervention of this deadly malignancy.
Answer 170:
New dihydrochalcones and anti-platelet aggregation constituents from the leaves of Muntingia calabura. Chen, Jih-Jung;
Lee, Hsinn-Hsing; Shih, Cheng-Dean; Liao, Chang-Hui; Chen, Ih-Sheng; Chou, Tsung-Hsien. Graduate Institute of Pharmaceutical
Technology, Tajen University, Pingtung, Taiwan. Planta Medica (2007), 73(6), 572-577. Publisher: Georg Thieme Verlag,
CODEN: PLMEAA ISSN: 0032-0943. Journal written in English. CAN 148:96612 AN 2007:865143 CAPLUS (Copyright (C)
Abstract
Two new dihydrochalcones, 2,3-dihydroxy-4,3',4',5'-tetramethoxydihydrochalcone (1) and 4,2',4'-trihydroxy-3'-methoxydihydrochalcone

(2), and a new flavanone, (2R,3R)-(-)-3,5-dihydroxy-6,7-dimethoxyflavanone (3), together with 19 known compds. were isolated from
the leaves of Muntingia calabura. The structures of three new compds. were detd. through spectral analyses including extensive
2D-NMR data. Among the isolates, 2,3-dihydroxy-4,3',4',5'-tetramethoxydihydrochalcone, 5,7-dihydroxy-3-methoxyflavone,
5,7-dihydroxy-6-methoxyflavone, 5,4'-dihydroxy-3,7-dimethoxyflavone, (2S)-7,8,3',4',5'-pentamethoxyflavan,
flavanone
(2S)-5'-hydroxy-7,8,3',4'-tetramethoxyflavan, and Me gallate exhibited significant anti-platelet aggregation activity in vitro.
Answer 171:
Flavonoids and the risk of oral and pharyngeal cancer: a case-control study from Italy. Rossi, Marta; Garavello, Werner;
Talamini, Renato; Negri, Eva; Bosetti, Cristina; Dal Maso, Luigino; Lagiou, Pagona; Tavani, Alessandra; Polesel, Jerry; Barzan, Luigi;
Ramazzotti, Valerio; Franceschi, Silvia; La Vecchia, Carlo. Istituto di Ricerche Farmacologiche "Mario Negri", Milan, Italy. Cancer
Epidemiology, Biomarkers & Prevention (2007), 16(8), 1621-1625. Publisher: American Association for Cancer Research, CODEN:
CEBPE4 ISSN: 1055-9965. Journal written in English. CAN 148:10428 AN 2007:863998 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
The intake of flavonoids has been inversely related to the risk of various common neoplasms, but scanty data exist on oral and
pharyngeal cancer. We used data from a case-control study conducted in Italy between 1992 and 2005 to examine the relationship
between flavonoid intake and oral and pharyngeal cancer risk. The study included 805 cases with incident, histol. confirmed oral and
pharyngeal cancer, and 2,081 hospital controls admitted for acute, nonneoplastic conditions. We have applied data on food and
beverage content of six major classes of flavonoids, on dietary information collected through a validated food-frequency
questionnaire. The odds ratios (OR) were calcd. using multiple logistic regression models, conditioned on study center, sex, and age.
After adjustment for education, tobacco, alc., body mass index, and non-alc. energy intake, ORs for the highest vs. the lowest quintile
of intake were 0.51 [95% confidence intervals (95% CI), 0.37-0.71] for flavanones, 0.62 (CI, 0.43-0.89) for flavonols, and 0.56 (95%
CI, 0.40-0.78) for total flavonoids. No significant assocn. emerged for isoflavones (OR, 0.90), anthocyanidins (OR, 0.86),
flavan-3-ols (OR, 0.84), and flavones (OR, 0.75). The ORs were consistent across strata of age, sex, education, body mass index,
tobacco, and alc. After allowance for vegetable and fruit consumption, the inverse relations with total flavonoids and flavanones
remained significant, whereas that with flavonols became nonsignificant. None of the assocns. were significant after further allowance
for vitamin C, probably on account of the high collinearity between these compds.
Answer 172:
Effects of naturally occurring dihydroflavonols from Inula viscosa on inflammation and enzymes involved in the
arachidonic acid metabolism. Hernandez, Victoriano; Recio, M. Carmen; Manez, Salvador; Giner, Rosa M.; Rios, Jose-Luis.
Departament de Farmacologia, Facultat de Farmacia, Universitat de Valencia, Spain. Life Sciences (2007), 81(6), 480-488.
Publisher: Elsevier B.V., CODEN: LIFSAK ISSN: 0024-3205. Journal written in English. CAN 148:229481 AN 2007:857083
Abstract
The anti-inflammatory properties of 3 flavanones isolated from Inula viscosa, sakuranetin, 7-O-methylaromadendrin, and
3-acetyl-7-O-methylaromadendrin, were tested both in vitro and in vivo. Acute inflammation in vivo was induced by topical application
of 12-O-tetradecanoylphorbol 13-acetate (TPA) to mouse ears or by s.c. injection of phospholipase A2 (PLA2) into mouse paws. The
test compds. were evaluated in vitro for their effect on both the metab. of arachidonic acid and on the release and/or activity of
enzymes involved in the inflammatory response such as elastase, myeloperoxidase (MPO), and protein kinase C (PKC). The most
active compds. in vivo against PLA2-induced paw edema were 7-O-methylaromadendrin (ED50 = 8 mg/kg) and sakuranetin (ED50 = 18
mg/kg). In contrast, the most potent compd. against TPA-induced ear edema was 3-acetyl-7-O-methylaromadendrin (ED50 = 185
μg/ear), followed by sakuranetin (ED50 = 205 μg/ear). In vitro, the latter compd. was the most potent inhibitor of leukotriene (LT) B4
prodn. by peritoneal rat neutrophils (IC50 = 9 μM) and it was also the only compd. that directly inhibited the activity of 5-lipoxygenase
(5-LOX). 3-Acetyl-7-O-methylaromadendrin also inhibited LTB4 prodn. (IC50 = 15 μM), but had no effect on 5-LOX activity. The only
flavanone
flavanone that inhibited the secretory PLA2 activity in vitro was 7-O-methylaromadendrin. This finding may partly explain the
anti-inflammatory effect obsd. in vivo, although other mechanisms such as the inhibition of histamine release by mast cells may also
be implicated. Sakuranetin at 100 μM was found to inhibit elastase release, although this result is partly due to direct inhibition of the
enzyme itself. At the same concn., 7-O-methylaromadendrin only affected the enzyme release. Finally, none of the flavanones
exhibited any effect on MPO or PKC activities. Taken together, these findings indicate that sakuranetin may be a selective inhibitor of
5-LOX.
Answer 173:
Flavanone plasma pharmacokinetics from blood orange juice in human subjects. Gardana, Claudio; Guarnieri, Serena; Riso,
Patrizia; Simonetti, Paolo; Porrini, Marisa. DiSTAM - Department of Food Science and Microbiology, Division of Human Nutrition,
University of Milan, Milan, Italy. British Journal of Nutrition (2007), 98(1), 165-172. Publisher: Cambridge University Press,
CODEN: BJNUAV ISSN: 0007-1145. Journal written in English. CAN 147:226136 AN 2007:847033 CAPLUS (Copyright (C)
Abstract
Some blood orange juice (BOJ) flavanones may have antioxidant, anti-inflammatory, anti-allergic, hypolipidemic, vasoprotective, and
anticarcinogenic properties. The aim of the present study was to evaluate the pharmacokinetics of hesperetin and naringenin in human
subjects after BOJ intake. In a cross-over study, 7 healthy female volunteers consumed 150 and 300 mL BOJ corresponding to about
51-102 mg hesperetin and to 6-12 mg naringenin, resp. Plasma samples were collected before, each hour for 8 h and 24 h after BOJ
administration and analyzed for their content of hesperetin and naringenin by liq. chromatog.-MS/MS. The blood plasma concns. of
these compds. were dose dependent and the peak concn. (Cmax) was reached in 5⋅1 h after BOJ intake. The Cmax of hesperetin was
43⋅4 and 79⋅8 ng/mL after 150 and 300 mL intake, resp. For naringenin the plasma peak was 16⋅4 and 34⋅0 ng/mL. Moreover, the
conjugated forms of these flavanones represent more than 95% of the plasma concn. The results indicate that both hesperetin and
naringenin are bioavailable after BOJ intake; naringenin seemingly more so than hesperetin.
Answer 174:
Absorption and pharmacokinetics of grapefruit flavanones in beagles. de Lourdes Mata-Bilbao, Maria; Andres-Lacueva,
Cristina; Roura, Elena; Jauregui, Olga; Escribano, Elvira; Torre, Celina; Lamuela-Raventos, Rosa Maria. Department of Nutrition and
Food Science, CerTA, Faculty of Pharmacy, University of Barcelona, Barcelona, Spain. British Journal of Nutrition (2007), 98(1),
86-92. Publisher: Cambridge University Press, CODEN: BJNUAV ISSN: 0007-1145. Journal written in English. CAN 147:226135
Abstract
The present study evaluated the pharmacokinetics of 3 different grapefruit flavanone forms in dog blood plasma and demonstrated
their absorption after an oral intake of a grapefruit ext.; pharmacokinetic parameters of these forms were also detd. Ten healthy
beagles were administered 70 mg citrus flavonoids as a grapefruit ext. contained in capsules, while 2 addnl. dogs were used as controls
and given an excipient. The grapefruit flavanone naringin, along with its metabolites naringenin and naringenin glucuronide, was
detected in dog plasma. Blood samples were collected between 0 and 24 h after administration of the ext. Naringin reached its max.
plasma concn. at around 80 min, whereas naringenin and naringenin glucuronide reached their max. plasma concn. at around 20 and 30
min, resp. Maximum plasma concns. of naringin, naringenin, and naringenin glucuronide (medians and ranges) were 0.24 (0.05-2.08),
0.021 (0.001-0.3), and 0.09 (0.034-0.12) μmol/l, resp. The areas under the curves were 23.161 (14.04-70.62) min × μmol/for nariningin,
1.78 (0.09-4.95) min × μmol/l for naringenin, and 22.5 (2.74-99.23) min × μmol/l for naringenin glucuronide. The median and range
values for mean residence time were 3.3 (1.5-9.3), 2.8 (0.8-11.2), and 8.0 (2.3-13.1) h for naringin, naringenin, and naringenin
flavanone
glucuronide, resp. The results of the present study demonstrate the absorption of grapefruit flavanones via the presence of their
metabolites in plasma, thus making an important contribution to the field since the biol. activities ascribed to these compds. rely on
their specific forms of absorption.
Answer 175:
Identification of flavanones from peel of Citrus changshan-huyou Y. B. Chang, by HPLC-MS and NMR. Li, Chunmei; Gu,
Haifeng; Dou, Hongliang; Zhou, Liming. College of Food Science and Technology, Huazhong Agriculture University, Wuhan City,
Peop. Rep. China. European Food Research and Technology (2007), 225(5-6), 777-782. Publisher: Springer GmbH, CODEN:
EFRTFO ISSN: 1438-2377. Journal written in English. CAN 148:187092 AN 2007:840522 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
High-performance liq. chromatog. coupled with a UV photodiode-array detector and a mass spectrometer (HPLC-MS) was used to
analyze the constituents of an ext. of Citrus changshan-huyou Y. B. Chang peel. Structures of two flavanones were identified based
on their abundant [M+H]+ ions, UV spectra, and 1HNMR and 13CNMR spectrometer as 5,4'-dihydroxy flavanone-7-O-α-glucoside
(naringenin-7-O-α-glucoside) and 5,3'-dihydroxy-4'-methoxy flavanone-7-O-α-glucoside (hesperetin-7-O-α-glucoside). The two
flavanones were first identified from peel of Citrus changshan-huyou Y. B. Chang.
Answer 176:
Effect of technological processes and storage on flavonoids content and total, cumulative fast-kinetics and cumulative
slow-kinetics antiradical activities of citrus juices. Sentandreu, Enrique; Navarro, Jose L.; Sendra, Jose M. Instituto de
Agroquimica y Tecnologia de Alimentos, Burjassot, Valencia, Spain. European Food Research and Technology (2007), 225(5-6),
905-912. Publisher: Springer GmbH, CODEN: EFRTFO ISSN: 1438-2377. Journal written in English. CAN 147:468220 AN
Abstract
Juices from the mandarin Clemenules (Citrus clementina Hort. ex Tan.), the tangor Ortanique (Citrus reticulata Blanco × Citrus sinensis
Osb.) and the sweet orange Valencia Late (Citrus sinensis) have been industrially squeezed, pasteurized, concd. and stored under
refrigeration (4°) and at room temp. (20°). After each process, the flavanone-7-O-glycosides (FGs) and fully methoxylated flavones
(FMFs) contents as well as total, cumulative fast-kinetics and cumulative slow-kinetics antiradical activities were detd. and compared
with those from the corresponding fresh hand-squeezed juices. Neither industrial-squeezing, nor pasteurization or concn. significantly
affected FGs and FMFs contents and antiradical activities of assayed juices. Storage caused a slight decrease of the FMFs contents
but a significant redn. of both sol. hesperidin contents and cumulative fast-kinetics antiradical activities in all assayed juices. These
decreases were dependent on storage temp. Characteristic values of the varietal characterization parameters, which are derived from
the FMFs contents and antiradical activities of fresh hand-squeezed juices, held valid for industrially squeezed, pasteurized and concd.
juices. After storage, however, only the FMFs-derived varietal characterization parameters and cumulative slow-kinetics antiradical
activity remained valid for the resulting juices.
Answer 177:
flavanone
(+)-Silybin, a pharmacologically active constituent of Silybum marianum: fragmentation studies by atmospheric pressure
chemical ionization quadrupole time-of-flight tandem mass spectrometry. Keki, Sandor; Toth, Katalin; Zsuga, Miklos; Ferenczi,
Renata; Antus, Sandor. Department of Applied Chemistry, University of Debrecen, Debrecen, Hung. Rapid Communications in
Mass Spectrometry (2007), 21(14), 2255-2262. Publisher: John Wiley & Sons Ltd., CODEN: RCMSEF ISSN: 0951-4198. Journal
Abstract
The fragmentation behavior of (+)-silybin (I) and (+)-deuterosilybin (II), as well as of their flavanone-3-of-type building blocks, such as
3,5,7-trihydroxy-2-phenyl-4-chromanone (III) and 2-(1,4-benzodioxolanyl)-3,5,7-trihydroxy-4-chromanone (IV), were investigated by
atm. pressure chem. ionization quadrupole time-of-flight tandem mass spectrometry in the pos. ion mode (APCI(+)-QqTOF MS/MS).
The product ion spectra of the protonated mols. of I revealed a rather complicated fragmentation pattern with product ions originating
from consecutive and competitive loss of small mols. such as H2O, CO, CH2O, CH3OH and 2-methoxyphenol, along with the A+ -
and B+-type ions arising from the cleavage of the C-ring of the flavanone-3-ol moiety. The elucidation of the fragmentation behavior
of I was facilitated by acquiring information on the fragmentation characteristics of the flavanone-3-ol moieties and II. The capability
of the accurate mass measurement on the quadrupole time-of-flight mass spectrometer allowed us to det. the elemental compn. of
each major product ion. Second-generation product ion spectra obtained by combination of in-source collision induced dissocn. (CID)
with selective CID (pseudo-MS3) was also helpful in elaborating the fragmentation pathways and mechanism. Based on the exptl.
results, a fragmentation mechanism as well as fragmentation pathways for I and its flavanone-3-ol building blocks III, IV are proposed
and discussed.
flavanone
H
O
OH
H
HO O OMe
O
R
OH OH
H
OH O I
H
O
OH
H
HO O OMe
O
D
OH OH
H
OH O II
H H
HO O HO O
O
OH OH
H H
OH O III OH O IV
Answer 178:
Antioxidant and cytotoxic activities of naturally occurring phenolic and related compounds: A comparative study. Rao,
Yerra Koteswara; Geethangili, Madamanchi; Fang, Shih-Hua; Tzeng, Yew-Min. Institute of Biotechnology, Chaoyang University of
Technology, Wufeng, Taichung, Taiwan. Food and Chemical Toxicology (2007), 45(9), 1770-1776. Publisher: Elsevier Ltd.,
CODEN: FCTOD7 ISSN: 0278-6915. Journal written in English. CAN 148:182415 AN 2007:829723 CAPLUS (Copyright (C)
Abstract
The antioxidant (DPPH radical and superoxide anion scavenging activities), and cytotoxic (in tumor, Jurkat, PC-3, Colon 205, HepG2,
and normal PBMCs cells) activities of 16 plant phenolic or related compds. were evaluated in vitro. Different categories compds.
flavanone
corresponding to 10 flavonoids, three lignans, two phenolic acids, and a catechin showed significant mean differences in antioxidant
and cytotoxic activities. Particularly, the flavonols, quercetin (3) and tiliroside (11) possess significant antioxidant activity, as well as
cytotoxic activity against Jurkat; and Jurkat and HepG2 cells, resp. In contrast, the flavanone,
5,7-dimethoxy-3',4'-methylenedioxyflavanone (7), and homoisoflavonoid, isobonducellin (10) shown to have no significant antioxidant
activity, but exhibited potent cytotoxic activity in Jurkat and HepG2 cells, while moderate growth inhibition against Colon205 cells.
Interestingly, none of these derivs. shown to have toxicity toward normal peripheral blood mononuclear cells, over the concn. range
tested (5-200 μM). Cytotoxic activities of some natural flavonoids identified in the medicinal plants were evaluated for the first time.
Answer 179:
Evolution of flavone synthase I from parsley flavanone 3β-hydroxylase by site-directed mutagenesis. Gebhardt, Yvonne
Helen; Witte, Simone; Steuber, Holger; Matern, Ulrich; Martens, Stefan. Institut fuer Pharmazeutische Biologie, Philipps-Universitaet
Marburg, Marburg, Germany. Plant Physiology (2007), 144(3), 1442-1454. Publisher: American Society of Plant Biologists,
CODEN: PLPHAY ISSN: 0032-0889. Journal written in English. CAN 147:338207 AN 2007:827624 CAPLUS (Copyright (C)
Abstract
Flavanone 3β-hydroxylase (FHT) and flavone synthase I (FNS I) are 2-oxoglutarate-dependent dioxygenases with 80% sequence
identity, which catalyze distinct reactions in flavonoid biosynthesis. However, FNS I has been reported exclusively from a few
Apiaceae species, whereas FHTs are more abundant. Domain-swapping expts. joining the N terminus of parsley (Petroselinum
crispum) FHT with the C terminus of parsley FNS I and vice versa revealed that the C-terminal portion is not essential for FNS I
activity. Sequence alignments identified 26 amino acid substitutions conserved in FHT vs. FNS I genes. Homol. modeling, based on
the related anthocyanidin synthase structure, assigned seven of these amino acids (FHT/FNS I, M106T, I115T, V116I, I131F, D195E,
V200I, L215V, and K216R) to the active site. Accordingly, FHT was modified by site-directed mutagenesis, creating mutants encoding
from one to seven substitutions, which were expressed in yeast (Saccharomyces cerevisiae) for FNS I and FHT assays. The
exchange I131F in combination with either M106T and D195E or L215V and K216R replacements was sufficient to confer some FNS I
side activity. Introduction of all seven FNS I substitutions into the FHT sequence, however, caused a nearly complete change in
enzyme activity from FHT to FNS I. Both FHT and FNS I were proposed to initially withdraw the β-face-configured hydrogen from
carbon-3 of the naringenin substrate. Our results suggest that the 7-fold substitution affects the orientation of the substrate in the
active-site pocket such that this is followed by syn-elimination of hydrogen from carbon-2 (FNS I reaction) rather than the rebound
hydroxylation of carbon-3 (FHT reaction).
Answer 180:
Extraction and identification of total flavanone in gendarussa ventricosa. Sun, Ting-ting; Pei, Zheng-ling; Huang, Suo-yi.
Youjiang Medical College of Nationalities, Beise, Guangxi, Peop. Rep. China. Weiliang Yuansu Yu Jiankang Yanjiu (2007), 24(3),
23-24. Publisher: Weiliang Yuansu Yu Jiankang Yanjiu Zazhishe, CODEN: WYYJAF ISSN: 1005-5320. Journal written in Chinese.
Abstract
The flavonoids were extd. from gendarussa ventricosa by ultrasonic wave and ethanol extn. The coloration reaction and
paper-chromatog. were used to identify the flavonoids in gendarussa ventricosa. Spectrophotometry was used to det. the amt. of the
total flavanone. By this method, the concn. of total flavanone in gendarussa ventricosa was C = 0.1230 mg/mL and the recovery rate
was 99.05%. This method is simple without any pollution, and is an ideal way to ext. the total flavanone in gendarussa ventricosa.
Answer 181:
flavanone
Tryptase activity inhibitors containing polyphenols, plants, or plant extracts, and their use for topical or oral formulations,
foods, or beverages. Ito, Kenichi; Idamarcoda, Alnasili; Kido, Hiroshi. (Ichimaru Pharcos Inc., Japan; Tokushima University).
Jpn. Kokai Tokkyo Koho (2007), 36pp. CODEN: JKXXAF JP 2007186457 A 20070726 Patent written in Japanese. Application:
JP 2006-6124 20060113. Priority: . CAN 147:172994 AN 2007:813997 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))

JP 2007186457 A 20070726 JP 2006-6124 20060113
JP 2006-6124 20060113
Abstract
The tryptase activity inhibitors contain catechins and/or their glycosides, flavones and/or their glycosides, flavonols and/or their
glycosides, flavanones and/or their glycosides, and/or tannins as active ingredients. Topical or oral formulations, foods, or beverages
contg. the tryptase inhibitors are useful for treatment or prevention of diseases selected from itching, wrinkle, bags in skin, rough skin,
systemic anaphylaxis, aspirin hypersensitivity asthma, asthma, interstitial lung disease, interstitial cystitis, irritable bowel syndrome,
allergy, atopic disease, bullous dermatosis, hyperesthesia, pain, pruritus, gingivitis, edema, psoriasis, lung fibrosis, chronic rheumatoid
arthritis, periodontal disease, blood coagulation disorder, renal interstitial fibrosis, vascular hyperpermeability or pneumonedema caused
by radiog. contrast media, and pollinosis. Thus, tannic acid (at 1 mg/mL) showed 99.7% inhibition of purified human tryptase. Tannic
acid showed LD50 of ≥2000 mg/kg p.o. in mice. Formulation examples of skin-lightening lotions, emollient emulsions, shampoos, skin
cleansers, hair rinses, hair liqs., bath salts, health food tablets, health beverages, and toothpastes are given.
Answer 182:
Skin preparations containing flavanones and polar solvent extracts of Leguminosae plant containing lespedezaflavanone H.
Katagiri, Takayuki; Miyase, Toshio; Hongo, Maya. (Pola Chemical Industries, Inc., Japan). Jpn. Kokai Tokkyo Koho (2007),
16pp. CODEN: JKXXAF JP 2007186439 A 20070726 Patent written in Japanese. Application: JP 2006-4718 20060112. Priority:
. CAN 147:219391 AN 2007:813576 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))

JP 2007186439 A 20070726 JP 2006-4718 20060112
JP 2006-4718 20060112
Abstract
flavanone
Skin prepns., which inhibit melanin formation, contain flavanones I (R1-R6 = H, OH, isoprenyl; ≥3 of R1-R6 = isoprenyl) and/or their
salts. Also claimed are title exts. contg. 0.001-0.1% lespedezaflavanone H (II). Thus, II, obtained by extn. of Lespedeza buergeri
stem with MEOH and fractionation, inhibited melanin formation by normal human melanocyte in a dose-dependent manner. Application
of skin-lightening lotion contg. II and di-K glycyrrhizate to female volunteers with pigmentation (dark skin, spots, freckles, etc.) lighten
the skin color.
R4
R3 OH
R1
HO O
R5
R6
R2
OH O I
Answer 183:
Determining stability constants of naringenin (4',5,7-trihydroxy flavanone) complexes with aluminum(III) and iron(II) by
potentiometric and spectrophotometric methods. Karadag, Recep; Erdogan, Gulbin; Bayar, Mehmet; Dolen, Emre. Laboratory
for Natural Dyes, Faculty of Fine Arts, Marmara University, Istanbul, Turk. Reviews in Analytical Chemistry (2007), 26(3),
169-185. Publisher: Freund Publishing House Ltd., CODEN: RACYAX ISSN: 0048-752X. Journal written in English. CAN
Abstract
Naringenin and its metal complexes are used extensively in chem., biol. and dye industry. In this study, complexes of naringenin with
aluminum and iron are examd. by spectrophotometric and potentiometric methods. The stability consts. of these complexes were
detd. potentiometrically by using Calvin-Bjerrum and Irving Rossotti methods. The evaluated protonation consts. of the naringenin
were found: logK1 = 10.19, logK2 = 8.31, and logK3 = 7.06 at the 25°. Logarithms of the stability consts. were found: for Aluminum
complex: logK1 = 15.39 logK2 = 7.12, and logK3 = 6.47 and for Iron complex: logK1 = 10.11, logK2 = 6.40, and logK3 = 6.11 at the 25°.
The components of metal-naringenin complexes are given 1:3 (metal:naringenin ratio) both Al(III) and Fe(II) from the results.
Answer 184:
The constituents from the stems of Garcinia cowa Roxb. and their cytotoxic activities. Shen, Jie; Tian, Ze; Yang, Jun-shan.
Institute of Medicinal Plant Development, Peking Union Medical College, Chinese Academy of Medical Sciences, Beijing, Peop. Rep.
China. Pharmazie (2007), 62(7), 549-551. Publisher: Govi-Verlag Pharmazeutischer Verlag GmbH, CODEN: PHARAT ISSN:
Abstract
Three new flavanone glycosides named garccowaside A, garccowaside B, garccowaside C, and 3 other known compds. were isolated
from the ethanol ext. of the stems of G. cowa. These structures were established on the basis of spectroscopic evidence. Twelve
flavanone
compds. isolated from the stems of G. cowa were tested for cytotoxic activities.
Answer 185:
Constituents of the aerial part of Dryopteris sublaeta ching et Hsu. Zheng, Xiaoke; Dong, Sanli; Feng, Weisheng. School of
Basic Medical Sciences, Henan College of Traditional Chinese Medicine, Zhengzhou, Peop. Rep. China. Zhongguo Yaoxue Zazhi
(Beijing, China) (2006), 41(7), 500-501, 540. Publisher: Zhongguo Yaoxue Zazhishe, CODEN: ZYZAEU ISSN: 1001-2494. Journal
written in Chinese. CAN 148:246084 AN 2007:791213 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
The column of silica gel was employed for the isolation and purifn. of the compds. from Dryopteris sublaeta Ching et Hsu. The
structures of the compds. were identified by physiochem. properties and spectral anal. Five compds. were isolated from the ether
fraction of 70% acetone-exts., and their structures were identified as (2S)5,7-dihydroxy-6,8-dimethyl flavanone
(demethoxymatteucinol) (I), (2S)5,7-dihydroxy-4'-methoxyl-6,8-dimethyl flavanone (matteucinol) (II), (2S)5,7,2'-trihydroxy-6,8-dimethyl
flavanone (III), (2S)5,7,4'-trihydroxy-6,8-dimethyl-3'-methoxyl flavanone (IV),
(2S)5-hydroxy-6,8-dimethyl-4'-methoxyl-7-O-β-D-glucosyl flavanone (V). All the compds. are isolated from the aerial part of this plant
for the first time.
Answer 186:
Chemical constituents of the leaves of iris songarica. Wang, Xin; Qin, Minjian; Wu, Gang; Shu, Pan. Department of Traditional
Chinese Medical Resources, China Pharmaceutical University, Nanjing, Peop. Rep. China. Zhongguo Yaoke Daxue Xuebao
(2006), 37(3), 222-225. Publisher: Zhongguo Yaoke Daxue, CODEN: ZHYXE9 ISSN: 1000-5048. Journal written in Chinese.
Abstract
The chem. constituents of the leaves of Iris songarica Schrenk were studied. The chem. constituents is prepd. by extd. with 70% alc.,
isolating by column on silica gel and purifying by recrystn. etc. Eighteen compds. were isolated from the leaves of Iris songarica. On
the basis of the spectral data, the structures were identified as tectochrysin(I), wogonin(II),
acacetin-7-O-α-L-rhamnopyranosyl-(1,6)-β-D-glucopyranoside(III), izalpinin(IV), isorhamnetin-7-O-β-D-glucoside(V),
5,2'-dihydroxy-6,7-methylenedioxy flavanone (VI), 5,7-dihydroxy-6,2'-dimethoxyisoflavone (VII), tectorigenin (VIII), tectoridin (c),
irisolone , irisoid A(X I), irisoid B (X II), irisoid D(X III), n-hentriacontanol (X IV), daucosterol (X V), stigmasterol (X VI), nonadecanoic acid
(X VII) and β-sitosterol (X VIII). All the eighteen compds. have been isolated from this plant for the first time, and compds. III, IV and
V have been isolated from Iris for the first time.
Answer 187:
A new anticancer dihydroflavanoid from the root of Spiranthes australis (R. Brown) Lindl. Peng, Jinyong; Xu, Qiwei; Xu,
Youwei; Qi, Yan; Han, Xu; Xu, Lina. School of Pharmacy, Dalian Medical University, Dalian, Peop. Rep. China. Natural Product
Research, Part B: Bioactive Natural Products (2007), 21(7), 641-645. Publisher: Taylor & Francis Ltd., CODEN: NPRPEA Journal
flavanone
Abstract
A new dihydroflavanoid was obtained from the root of Spiranthes australis (R. Brown) Lindl, a traditional Chinese medicinal herb. The
structure was elucidated as (2S)-5,2',6'-trihydroxy-6-lavandulyl-4''-(γ,γ-dimethylallyl)-2'',2''-dimethylpyrano-[5'',6'':7,8]-flavanone by
spectroscopic methods including UV, IR, HR-EI-MS, ESI-MS, 1D NMR and 2D NMR techniques, and subsequently, the anticancer
activities of the compd. to inhibit human cancer cell growth including A549, BEL-7402, SGC-7901, MCF-7, HT-29, K562, and A498 cell
lines by MTT method was evaluated in vitro.
Answer 188:
2',5,7-Trihydroxy-4',5'-(2,2-dimethylchromeno)-8-(3-hydroxy-3-methylbutyl) flavanone purified from Cudrania tricuspidata

induces apoptotic cell death of human leukemia U937 cells. Rho, Yoon-Hwa; Yoon, Soo-Hyun; Kim, Eun-Kyung; Kang,
Ji-Young; Lee, Byong-Won; Park, Ki-Hun; Bae, Young-Seuk. Department of Biochemistry, College of Natural Sciences, Kyungpook
National University, Taegu, S. Korea. Natural Product Research, Part B: Bioactive Natural Products (2007), 21(7), 616-624.
Publisher: Taylor & Francis Ltd., CODEN: NPRPEA Journal written in English. CAN 148:291747 AN 2007:778581 CAPLUS
Abstract
Cellular DNA topoisomerase I is an important target in cancer chemotherapy. A chloroform ext. of the root barks of Cudrania
tricuspidata showed an inhibitory effect on mammalian DNA topoisomerase I. The topoisomerase I inhibitory compd. was purified and
identified as 2',5,7-trihydroxy-4',5'-(2,2-dimethylchromeno)-8-(3-hydroxy-3-methylbutyl) flavanone. The compd., temporarily
designated as PKH-3, was shown to inhibit the activity of topoisomerase I with IC50 about 1.0 mM. Concn. of 10 μM PKH-3 caused
50% growth inhibition of human cancer cell U937. PKH-3-induced cell death was characterized with the cleavage of poly(ADP-ribose)
polymerase (PARP) and pro-caspase 3. Furthermore, PKH-3 induced the fragmentation of DNA into multiples of 180 b.p. (an apoptotic
DNA ladder), indicating that the inhibitor triggered apoptosis. This induction of apoptosis by PKH-3 was also confirmed using flow
cytometry anal. Taken together, these results suggest that PKH-3 may function by inhibiting oncogenic disease, at least in part,
through the inhibition of topoisomerase I activity.
Answer 189:
Use of flavonoids to increase blood serum levels of dehydroepiandrosterone. Marchewitz, Eric. (USA). U.S. Pat. Appl.
Publ. (2007), 4pp. CODEN: USXXCO US 2007160688 A1 20070712 Patent written in English. Application: US 2007-652294
20070110. Priority: US 2006-757779 20060110. CAN 147:134491 AN 2007:763578 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))

US 20070160688 A1 20070712 US 2007-652294 20070110
US 2006-757779P P 20060110
flavanone
Abstract
A method is disclosed for increasing blood serum levels of dehydroepiandrosterone by administering the combination of one of a
flavonoid, isoflavonoid, coumarin and a flavonolignan; dehydroepiandrosterone; and a plant ext.
Answer 190:
Isolation and structure identification of chemical constituents from Patrinia villosa. Peng, Jinyong; Fang, Guorong; Wu,
Yutian. Key Laboratory for Pharmaceutical Metabolite Research, School of Pharmacy, Second Military Medical University,
Shanghai, Peop. Rep. China. Yaoxue Xuebao (2006), 41(3), 236-240. Publisher: Yaoxue Xuebao Bianjibu, CODEN: YHHPAL
SciFinder (R))
Abstract
This paper aims to study the chem. constituents of Patrinia villosa Juss. Solvent extn., silica gel column and preparative liq.
chromatog. were used to sep. the chem. constituents, and the chem. structures were elucidated by physico-chem. properties and
spectra data. Eight compds. were isolated and identified as bolusanthol B(1), (2S)- 5, 7, 2', 6' -tetrahydroxy-6, 8-di(χ, χ-dimethylallyl)
flavanone(2), orotinin(3), (2S)-5, 7, 2', 6'-tetrahydroxy-6-lavandulylated flavanone(4), 3'-prenyl-apigenine(5), luteolin(6), quercetin(7) and
apigenin(8). Compd. 2 and 4 were new compds.; compds. 1, 3 and 5 were sepd. from Patrinia genus for the first time; compds. 6, 7
and 8 were isolated from Patrinia villosa Juss for the first time.
Answer 191:
Prenyl flavanone compounds for promoting neural stem cells growth. Huang, Chung-Yang; Chen, Chien-Nan; Ho, Wan-Ju.
(Naturewise Biotech and Medicals Corporation, Taiwan). Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 30pp. CODEN:

CN 1990480 A 20070704 CN 2005-10097522 20051228
EP 1834952 A1 20070919 EP 2006-251426 20060317
US 20070232534 A1 20071004 US 2006-393619 20060330
JP 2007269650 A 20071018 JP 2006-94911 20060330
AU 2006201584 A1 20071101 AU 2006-201584 20060413
CN 2005-10097522 T0 20051228
flavanone
Abstract
The prenyl flavanone compds. are shown as chem. structure formula in claim 1, I; R1 is H, hydroxy, linear or branched alkyl with 1-3
C atom, or isoprene; R2, R3, R4, R5, R6 and R7 is H, hydroxy, linear or branched alkyl with 1-3 C atom, isoprene or geranyl shown as
structures in claim 2 resp. Title prenyl flavanone compds. for promoting neural stem cells growth is used to prepg. medicinal compn.
together with culture additive, growth factor etc.
R5
R4 OH
R3
HO O
R6
R7
R2 R1
OH O I
Answer 192:
C-Geranyl Compounds from Paulownia tomentosa Fruits. Smejkal, Karel; Grycova, Lenka; Marek, Radek; Lemiere, Filip;
Jankovska, Dagmar; Forejtnikova, Hana; Vanco, Jan; Suchy, Vaclav. Department of Natural Drugs and Department of Chemical
Drugs, University of Veterinary and Pharmaceutical Sciences Brno, Brno, Czech Rep. Journal of Natural Products (2007), 70(8),
1244-1248. Publisher: American Chemical Society-American Society of Pharmacognosy, CODEN: JNPRDF ISSN: 0163-3864.
Abstract
Five geranyl flavonoids, one prenylated flavonoid, and a simple flavanone were isolated from an ethanolic ext. of P. tomentosa fruit.
Tomentodiplacol (1), 3'-O-methyl-5'-methoxydiplacol (2), 6-isopentenyl-3'-O-methyltaxifolin (3), and dihydrotricin (4) are reported from a
natural source for the 1st time and 3'-O-methyldiplacone (6) for the 1st time from the genus Paulownia. The structures of the compds.
were detd. by mass spectrometry, including HR-MS, and by 1D and 2D NMR spectroscopy. The cytotoxicity and DPPH
(2,2-diphenyl-1-picrylhydrazyl)-quenching activity of some of these compds. were tested, with diplacone proving to be the best
antioxidant, although the most cytotoxic compd.
Answer 193:
Iodine/MeOH as a novel and versatile reagent system for the synthesis of α-ketothiocyanates. Yadav, J. S.; Reddy, B. V.
Subba; Reddy, U. V. Subba; Krishna, A. D. Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad,
India. Tetrahedron Letters (2007), 48(30), 5243-5246. Publisher: Elsevier Ltd., CODEN: TELEAY ISSN: 0040-4039. Journal
Abstract
flavanone
Ketones possessing α-hydrogens undergo thiocyanation with ammonium thiocyanate in the presence of mol. iodine in refluxing
methanol to produce the corresponding α-ketothiocyanates in excellent yields with high selectivity. The use of iodine makes this
procedure simple, convenient and cost effective.
Answer 194:
In silico screening of estrogen-like chemicals based on different nonlinear classification models. Liu, Huanxiang; Papa,
Ester; Walker, John D.; Gramatica, Paola. Department of Structural and Functional Biology, QSAR Research Unit in Environmental
Chemistry and Ecotoxicology, University of Insubria, Varese, Italy. Journal of Molecular Graphics & Modelling (2007), 26(1),
135-144. Publisher: Elsevier Inc., CODEN: JMGMFI ISSN: 1093-3263. Journal written in English. CAN 147:399612 AN
Abstract
Increasing concern is being shown by the scientific community, government regulators, and the public about endocrine-disrupting
chems. that are adversely affecting human and wildlife health through a variety of mechanisms. There is a great need for an
effective means of rapidly assessing endocrine-disrupting activity, esp. estrogen-simulating activity, because of the large no. of such
chems. in the environment. In this study, quant. structure activity relationship (QSAR) models were developed to quickly and
effectively identify possible estrogen-like chems. based on 232 structurally-diverse chems. (training set) by using several nonlinear
classification methodologies (least-square support vector machine (LS-SVM), counter-propagation artificial neural network (CP-ANN),
and k nearest neighbor (kNN)) based on mol. structural descriptors. The models were externally validated by 87 chems. (prediction
set) not included in the training set. All three methods can give satisfactory prediction results both for training and prediction sets, and
the most accurate model was obtained by the LS-SVM approach through the comparison of performance. In addn., our model was also
applied to about 58,000 discrete org. chems.; about 76% were predicted not to bind to estrogen receptor. The obtained results indicate
that the proposed QSAR models are robust, widely applicable and could provide a feasible and practical tool for the rapid screening of
potential estrogens.
Answer 195:
Application of microcalorimetric technique to the synthesis of NH2-SBA-15. Yang, Xu-Wei; Zhang, Xiao-Feng; Kan, Qiu-Bin;
Fu, Wei; Huang, Jia-Hui; Wu, Tong-Hao. Department of Physic Chemistry, College of Chemistry, Jilin University, Changchun,
Peop. Rep. China. Gaodeng Xuexiao Huaxue Xuebao (2007), 28(6), 1147-1150. Publisher: Gaodeng Jiaoyu Chubanshe, CODEN:
KTHPDM ISSN: 0251-0790. Journal written in Chinese. CAN 147:372732 AN 2007:711674 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
A series of NH2-SBA-15 were prepd. via a aminopropyl-triethoxysilane to react with SBA-15 and characterized with N2-BET, XRD,
elementary anal. and FTIR and flavanone was synthesize via condensation between 2'-hydroxyphenyl Me ketone and benzaldehyde
catalyzed by the catalyst NH2-SBA-15. The microcalorimetric technique was used to study quant. the surface base sites of
NH2-SBA-15 with intensity, no. and distribution. It was shown that the reaction condition (550,6,1.5) was the most compatible for
synthesis of NH2-SBA-15.
Answer 196:
flavanone
A novel synthesis of flavanones from 2-hydroxybenzoic acids. Lee, Jae In; Jung, Mi Gung; Jung, Hye Jin. Department of
Chemistry/Plant Resources Research Institute, College of Natural Science, Duksung Women's University, Seoul, S. Korea.
Bulletin of the Korean Chemical Society (2007), 28(5), 859-862. Publisher: Korean Chemical Society, CODEN: BKCSDE ISSN:
Abstract
A synthesis of flavanones I [R3 = R4 = R5 = R6 = R7 = H; R3 = H, R4 = Cl, R5 = R6 = R7 = H; R3 = H, R4 = OMe, R5 = R6 = R7 =

H; R3 = R4 = OMe, R5 = R6 = R7 = H; R3 = R4 = R5 = R6 = H, R7 = OMe; R3 = H, R4 = Cl, R5 = R6 = H, R7 = OMe; R3 = H, R4 =
OMe, R5 = R6 = H, R7 = OMe; R3 = R4 = R5 = H, R6 = OMe, R7 = H; R3 = H, R4 = Cl, R5 = H, R6 = OMe, R7 = H; R3 = H, R4 =
OMe, R5 = H, R6 = OMe, R7 = H; R3 = R4 = H, R5 = OMe, R6 = R7 = H; R3 = H, R4 = OMe, R5 = OMe, R6 = R7 = H] was achieved
via aldol addn. reactions of corresponding acetophenones II and benzaldehydes III using LDA in THF followed by treatment of the
reaction mixts. with a satd. NH4Cl soln. and subsequent intramol. cyclocondensation reactions of the resulting alcs. IV using PPh3 and
DEAD in CH2Cl2.
R4
R7 OH
R7 O
R3
Me
R6
R6
R5 O II
R5 O I
R4
R4
R7 OH
R3
OH
OHC R3 III
R6
R5 O IV
Answer 197:
Engineering central metabolic pathways for high-level flavonoid production in Escherichia coli. Leonard, Effendi; Lim,
Kok-Hong; Saw, Phan-Nee; Koffas, Mattheos A. G. Department of Chemical and Biological Engineering, University at Buffalo, The
State University of New York, Buffalo, NY, USA. Applied and Environmental Microbiology (2007), 73(12), 3877-3886. Publisher:
American Society for Microbiology, CODEN: AEMIDF ISSN: 0099-2240. Journal written in English. CAN 147:275782 AN
Abstract
The identification of optimal genotypes that result in improved prodn. of recombinant metabolites remains an engineering conundrum.
In the present work, various strategies to re-engineer central metab. in Escherichia coli were explored for robust synthesis of
flavanones, the common precursors of plant flavonoid secondary metabolites. Augmentation of the intracellular malonyl CoA
flavanone
(malonyl-CoA) pool through the coordinated overexpression of four acetyl-CoA carboxylase (ACC) subunits from Photorhabdus
luminescences (PlACC) under a constitutive promoter resulted in an increase in flavanone prodn. up to 576%. Exploration of
macromol. complexes to optimize metabolic efficiency demonstrated that auxiliary expression of PlACC with biotin ligase from the
same species (BirAPl) further elevated flavanone synthesis up to 1,166%. However, the coexpression of PlACC with Escherichia coli
BirA (BirAEc) caused a marked decrease in flavanone prodn. Activity improvement was reconstituted with the coexpression of PlACC
with a chimeric BirA consisting of the N terminus of BirAEc and the C terminus of BirAPl. In another approach, high levels of
flavanone synthesis were achieved through the amplification of acetate assimilation pathways combined with the overexpression of
ACC. Overall, the metabolic engineering of central metabolic pathways described in the present work increased the prodn. of
pinocembrin, naringenin, and eriodictyol in 36 h up to 1,379%, 183%, and 373%, resp., over prodn. with the strains expressing only the
flavonoid pathway, which corresponded to 429 mg/L, 119 mg/L, and 52 mg/L, resp.
Answer 198:
Melanin formation inhibiting cosmetics containing esters of menthol with C≥18 unsaturated fatty acid esters and
keratinocyte-derived hormone inhibitors, etc. Tanaka, Hiroshi. (Narisu Cosmetic Co., Ltd., Japan). Jpn. Kokai Tokkyo Koho
(2007), 20pp. CODEN: JKXXAF JP 2007161591 A 20070628 Patent written in Japanese. Application: JP 2005-355769
20051209. Priority: . CAN 147:124622 AN 2007:702220 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))

JP 2007161591 A 20070628 JP 2005-355769 20051209
JP 2005-355769 20051209
Abstract
Title cosmetics, which show synergistic melanin formation inhibiting action and prevent or treat UV-induced pigmentation, freckles, liver
spot, etc., contain (a) the menthol esters and (b) inhibitors for keratinocyte-derived hormones, antioxidants, inflammation inhibitors, or
polyols . Thus, NADPH inhibited thioredoxin/ADF prodn. by human keratinocyte. Application of a cream contg. menthol linoleate
(prepn. given), NADPH, and sunflower ext. to female volunteers reduced spots.
Answer 199:
Synthesis of Unnatural Flavonoids and Stilbenes by Exploiting the Plant Biosynthetic Pathway in Escherichia coli.
Katsuyama, Yohei; Funa, Nobutaka; Miyahisa, Ikuo; Horinouchi, Sueharu. Department of Biotechnology, Graduate School of
Agriculture and Life Sciences, University of Tokyo, Bunkyo-ku, Tokyo, Japan. Chemistry & Biology (Cambridge, MA, United
States) (2007), 14(6), 613-621. Publisher: Cell Press, CODEN: CBOLE2 ISSN: 1074-5521. Journal written in English. CAN
Abstract
Flavonoids and stilbenes have attracted much attention as potential targets for nutraceuticals, cosmetics, and pharmaceuticals. We
flavanone
have developed a system for producing "unnatural" flavonoids and stilbenes in Escherichia coli. The artificial biosynthetic pathway
included three steps. These included a substrate synthesis step for CoA esters synthesis from carboxylic acids by 4-coumarate:CoA
ligase, a polyketide synthesis step for conversion of the CoA esters into flavanones by chalcone synthase and chalcone isomerase,
and into stilbenes by stilbene synthase, and a modification step for modification of the flavanones by flavone synthase, flavanone
3β-hydroxylase and flavonol synthase. Incubation of the recombinant E. coli with exogenously supplied carboxylic acids led to prodn.
of 87 polyketides, including 36 unnatural flavonoids and stilbenes. This system is promising for construction of a larger library by
employing other polyketide synthases and modification enzymes.
Answer 200:
Synthesis of new flavonoids from 2',4'-dihydroxy-6'-methoxy-3',5'-dimethylchalcone. Zhang, Jian-feng; Jiang, Feng; Zhou,
Xiong. State Key Laboratory Base of Novel Functional Materials and Preparation Science, Faculty of Materials Science and Chemical
Engineering, Ningbo University, Ningbo, Peop. Rep. China. Hecheng Huaxue (2007), 15(3), 319-321, 349. Publisher: Hecheng
Huaxue Bianjibu, CODEN: HEHUE2 ISSN: 1005-1511. Journal written in English. CAN 148:471736 AN 2007:684328 CAPLUS
Abstract
A new flavone, 7-hydroxy-5-methoxy-6,8-dimethylflavone, was synthesized in 91% yield by treating of

2',4'-dihydroxy-6'-methoxy-3',5'-dimethylchalcone (1) with DMSO/I2. Two other flavonoids,
7-hydroxy-5-methoxy-6,8-dimethylflavanone and 5,7-dihydroxy-6,8-dimethylflavanone, were obtained from 1 in HCl/MeOH soln. in
70% and 20% yield, resp.
Answer 201:
Flavone synthases from Medicago truncatula are flavanone-2-hydroxylases and are important for nodulation. Zhang, Juan;
Subramanian, Senthil; Zhang, Yansheng; Yu, Oliver. Donald Danforth Plant Science Center, St. Louis, MO, USA. Plant
Physiology (2007), 144(2), 741-751. Publisher: American Society of Plant Biologists, CODEN: PLPHAY ISSN: 0032-0889. Journal
Abstract
Flavones are important copigments found in the flowers of many higher plants and play a variety of roles in plant adaptation to stress.
In Medicago species, flavones also act as signal mols. during symbiotic interaction with the diazotropic bacterium Sinorhizobium
meliloti. They are the most potent nod gene inducers found in root exudates. However, flavone synthase II (FNS II), the key enzyme
responsible for flavone biosynthesis, has not been characterized in Medicago species. We cloned two FNS II genes from Medicago
truncatula using known FNS II sequences from other species and named them MtFNSII-1 and MtFNSII-2. Functional assays in yeast
(Saccharomyces cerevisiae) suggested that the catalytic mechanisms of both cytochrome P 450 monooxygenases were similar to the
other known legume FNS II from licorice (Glycyrrhiza echinata). MtFNSII converted flavanones to 2-hydroxyflavanones instead of
flavones whereas FNS II from the nonlegume Gerbera hybrida, converted flavanones to flavones directly. The two MtFNSII genes
had distinct tissue-specific expression patterns. MtFNSII-1 was highly expressed in roots and seeds whereas MtFNSII-2 was highly
expressed in flowers and siliques. In addn., MtFNSII-2 was inducible by S. meliloti and Me jasmonate treatment, whereas MtFNSII-1
was not. Histochem. staining of transgenic hairy roots carrying the promoter-reporter constructs indicated that the MtFNSII-2 induction
was tissue specific, mostly localized to vascular tissues and root hairs. RNA interference-mediated suppression of MtFNSII genes
resulted in flavone depleted roots and led to significantly reduced nodulation when inoculated with S. meliloti. Our results provide
genetic evidence supporting that flavones are important for nodulation in M. truncatula.
Answer 202:
flavanone
Anthocyanin content in rice is related to expression levels of anthocyanin biosynthetic genes. Kim, Bong Gyu; Kim, Jeong
Ho; Min, Shin Young; Shin, Kwang-Hee; Kim, Ji Hye; Kim, Hong Yeol; Ryu, Su Noh; Ahn, Joong-Hoon. Division of Bioscience and
Biotechnology, Bio/Molecular Informatics Center, IBST, Seoul, S. Korea. Journal of Plant Biology (Seoul, Republic of Korea)
(2007), 50(2), 156-160. Publisher: Botanical Society of Korea, CODEN: JPBIEZ ISSN: 1226-9239. Journal written in English.
Abstract
The compn. of anthocyanins was analyzed in two rice cultivars. 'Ilpum' showed no detectable levels, while 'Heugjinju' contained three
types of anthocyanins: cyanidin, cyanidin 3-O-glucoside, and peonidin 3-O-glucoside. We also assessed the expression of
anthocyanin biosynthetic genes - for phenylalanine ammonia lyase (PAL), chalcone synthase (CHS), flavanone 3β-hydroxylase (F3H),
dihydroflavonol reductase (DFR), and anthocyanin synthase (ANS) - in different tissues of those cultivars. All five genes were
expressed more in the leaves and seeds of 'Heugjinju' than in 'Ilpum', with the greatest amt. of transcript being detected in 'Heugjinju'
seeds. Two genes, DFR and ANS, had relatively high expression levels and were specific for anthocyanin biosynthesis. Furthermore,
expression of CHS, F3H, DFR, and ANS was enhanced during seed maturation and was correlated with ambient temp. during seedling
growth.
Answer 203:
Interaction between the aryl hydrocarbon receptor and its antagonists, flavonoids. Fukuda, Itsuko; Mukai, Rie; Kawase,
Masaya; Yoshida, Ken-ichi; Ashida, Hitoshi. Research Center for Food Safety and Security, Graduate School of Agricultural
Science, Kobe University, Kobe, Hyogo, Japan. Biochemical and Biophysical Research Communications (2007), 359(3),
822-827. Publisher: Elsevier, CODEN: BBRCA9 ISSN: 0006-291X. Journal written in English. CAN 147:269152 AN 2007:658816
Abstract
Flavonoids have been reported to be dietary antagonists of an aryl hydrocarbon receptor (AhR). However, little is known about the
mol. mechanism on their antagonistic effects. In this study, the inhibitory effect of flavonoids on ligand binding to the AhR and
interaction between flavonoids and the AhR complex (AhRc) were investigated in each flavonoid subclass. Flavone, flavonol, and
flavanone but not catechin inhibited the specific binding between the AhR and 3-methylcholanthrene dose-dependently, indicating that
the former three subclasses possibly act as competitive antagonists of the AhR. However, catechin in addn. to the former three
subclasses directly interacted with the AhRc by surface plasmon resonance anal. The dissocn. const. values showed an inverse
correlation with the suppressive effect on the DNA binding activity. These results suggest that flavone, flavonol, and flavanone act
as competitive antagonists of the AhR, while catechin assocs. with the AhRc and indirectly exhibits its antagonistic effects.
Answer 204:
High throughput quantification of phytoestrogens in human urine and serum using liquid chromatography/tandem mass
spectrometry (LC-MS/MS). Grace, Philip B.; Mistry, Nayan S.; Carter, Megan H.; Leathem, Anthony J. C.; Teale, Philip. HFL,
Cambridgeshire, UK. Journal of Chromatography, B: Analytical Technologies in the Biomedical and Life Sciences (2007), 853(1-2),
138-146. Publisher: Elsevier B.V., CODEN: JCBAAI ISSN: 1570-0232. Journal written in English. CAN 147:180438 AN
flavanone
Abstract
Phytoestrogens are currently the subject of intense study owing to their potential protective effects against a no. of complex
diseases. However, in order to investigate the interactions between phytoestrogens and disease state effectively, it is necessary to
have anal. methods which are sensitive, reproducible, and require low sample vols. The authors report an assay for 3 isoflavones
(daidzein, genistein, and glycitein), 2 metabolites of daidzein (equol and O-desmethylangolensin), 3 lignans (secoisolariciresinol,
enterodiol, and enterolactone), and 1 flavanone (naringenin) in human urine and serum. A high throughput of samples has been
achieved via the use of 96-well plate sample extn. and liq. chromatog./tandem mass spectrometry (LC-MS/MS) anal. incorporating
column switching, thus making the assay suitable for use on large sample nos., such as those found in epidemiol. studies. The
robustness of the assay was proven via the comparison of data generated on two different LC-MS/MS systems, with and without
column switching.
Answer 205:
A proteomic screen and identification of waterlogging-regulated proteins in tomato roots. Ahsan, Nagib; Lee, Dong-Gi; Lee,
Sang-Hoon; Lee, Ki-Won; Bahk, Jeong Dong; Lee, Byung-Hyun. Division of Applied Life Sciences (BK21 program), Gyeongsang
National University, Jinju, S. Korea. Plant and Soil (2007), 295(1-2), 37-51. Publisher: Springer, CODEN: PLSOA2 ISSN:
Abstract
To gain a better understanding of the tomato root response to waterlogging stress at protein level, a proteomic approach has been
conducted in combination with physiol. analyses. Five-week old plants were subjected to waterlogging stress, and roots were collected
24 and 72 h after treatment. Waterlogging stress resulted in a gradual increase of lipid peroxidn. and in vivo H2O2 concn. in roots. To
elucidate temporal changes in protein expression in tomato roots, proteins were extd. from the root samples, sepd. by 2-DE, and
visualized by staining with Coomassie Brilliant Blue. A total of 35 proteins were differentially expressed in tomato roots in response to
waterlogging stress, and 29 were identified using MALDI-TOF anal. Of the proteins identified, 16 proteins were up-regulated and 13
proteins were down-regulated in waterlogged tomato roots. In addn. to previously identified waterlogging-regulated proteins, we
identified several novel proteins, including 3-beta-hydroxylase, phenylalanine ammonia-lyase, glutamyl-tRNA reductase, flavanone
3-hydroxylase, mitochondrial ATPase alpha subunit, cysteine protease, DWARF1, and NIM1-like protein 2. These newly identified
proteins are involved in several cellular processes, including hormone and secondary metabolite synthesis, programmed cell death,
and stress and defense mechanisms. Five differentially accumulated proteins were further analyzed at the mRNA level, which
confirmed the differential gene expression, and revealed that the transcript levels were not always consistent with the translation level.
The identification of these novel proteins in the waterlogging stress response provides new insight that can lead to a better
understanding of the mol. basis of waterlogging-sensitivity in plants.
Answer 206:
Suppression subtractive hybridization identifies genes induced in response to UV-B irradiation in apple skin: isolation of a
putative UDP-glucose 4-epimerase. Ban, Yusuke; Honda, Chikako; Bessho, Hideo; Pang, Xiao-Ming; Moriguchi, Takaya.
Graduate School of Life and Environmental Sciences, University of Tsukuba, Tsukuba, Ibaraki, Japan. Journal of Experimental
Botany (2007), 58(7), 1825-1834. Publisher: Oxford University Press, CODEN: JEBOA6 ISSN: 0022-0957. Journal written in
Abstract
flavanone
Suppression subtractive hybridization (SSH) successfully identified 11 cDNAs in apple skin with highly induced expression as a result
of UV-B irradn. Apart from three putative flavonoid biosynthetic genes, chalcone synthase (CHS; A5C), flavanone-3-hydroxylase
(F3H; B5F), and flavonol synthase (FLS; D1F), five clones (A1H, A10E, B11G, D5F, and D11H) were induced by low temp. (17°) as
well, which is also known to induce anthocyanin accumulation in apple skin. Moreover, four clones (A1H, A10E, B11G, and D11H),
showing higher expression levels in the skin, accumulated higher anthocyanin concns. than their counterparts. Of the four clones, only
A10E, a putative UDP-glucose 4-epimerase (UGE), was deemed to play an important role in anthocyanin accumulation in apple skin
based on the facts that:. (i) its transcription level was higher in the deep red cultivar, 'Jonathan', than in the pale red cultivar,
'Tsugaru'; and. (ii) it could reversibly catalyze UDP-glucose to UDP-galactose, and the latter mol. is a major sugar donor for
cyanidin-glycoside in apple. Therefore, the full-length cDNA of A10E was isolated by rapid amplification of cDNA ends (RACE) and
designated as MdUGE1. Further anal. demonstrated that UGE enzymic activity was pos. correlated with anthocyanin accumulation in
apple skin. Thus, MdUGE1 isolated by SSH could play an important role in anthocyanin biosynthesis in apple skin in concert with other
flavonoid biosynthetic genes.
Answer 207:
Ultraviolet A-specific induction of anthocyanin biosynthesis in the swollen hypocotyls of turnip (Brassica rapa). Zhou, Bo;
Li, Yuhua; Xu, Zhiru; Yan, Haifang; Homma, Shinichiro; Kawabata, Saneyuki. College of Life Sciences, Northeast Forestry
University, Harbin, Peop. Rep. China. Journal of Experimental Botany (2007), 58(7), 1771-1781. Publisher: Oxford University
Press, CODEN: JEBOA6 ISSN: 0022-0957. Journal written in English. CAN 147:296237 AN 2007:653111 CAPLUS
Abstract
UV A (UV-A)-mediated regulation of anthocyanin biosynthesis was investigated in swollen hypocotyls of the red turnip 'Tsuda'. The
shaded swollen hypocotyls which contained negligible anthocyanin were exposed to artificial light sources including low fluence UV-B,
UV-A, blue, red, far-red, red plus UV-A, far-red plus UV-A, and blue plus red. Among these lights, only UV-A induced anthocyanin
biosynthesis and co-irradn. of red or far-red with UV-A did not affect the extent of UV-A-induced anthocyanin accumulation. The
expression of phenylalanine ammonia lyase (PAL; EC 4.3.1.5), chalcone synthase (CHS; EC 2.3.1.74), flavanone 3-hydroxylase
(F3H; EC 1.14.11.9), dihydroflavonol 4-reductase (DFR; EC 1.1.1.219), and anthocyanidin synthase (ANS; EC 1.14.11.19) genes was
increased with time during a 24 h exposure to UV-A. In contrast, irradn. with red, blue, UV-B, and a combination of blue with red failed
to induce CHS expression. Microarray anal. showed that only a few genes, including CHS and F3H, were induced significantly by
UV-A, while a sep. set of many genes was induced by low fluence UV-B. The UV-A-specific induction of anthocyanin biosynthesis
and the unique gene expression profile upon UV-A irradn. as compared with blue and UV-B demonstrated that the obsd. induction of
anthocyanin biosynthesis in red turnips was mediated by a distinct UV-A-specific photoreceptor, but not by phytochromes, UV-A/blue
photoreceptors, or UV-B photoreceptors.
Answer 208:
Multiparallel chiral separation screening. Screening of chiral stationary and mobile phases. Francotte, Eric; Huynh, Dan;
Wetli, Herbert A. Novartis Institutes for BioMedical Research, Basel, Switz. GIT Labor-Fachzeitschrift (2006), 50(5), 452-455.
Publisher: GIT Verlag GmbH & Co. KG, CODEN: GLFAF5 Journal written in German. CAN 147:102352 AN 2007:650107
Abstract
A HPLC system for the chiral sepn. is presented allowing the parallel simultaneous testing of 8 chiral columns with different mobile
phases. The immobilized chiral stationary phases are based on aryl carbamate and benzoate derivs. of cellulose and amylose. The
flavanone
configuration allows the test of 230 resp. 460 (chromatog. run of 40 resp. 15 min) conditions in 24 h. Conditions were found to sep. the
enantiomers of racemic glutethimide and flavanone.
Answer 209:
Kinetic Model for the Antiradical Activity of the Isolated p-Catechol Group in Flavanone Type Structures Using the Free
Stable Radical 2,2-Diphenyl-1-picrylhydrazyl as the Antiradical Probe. Sendra, Jose M.; Sentandreu, Enrique; Navarro, Jose L.
Instituto de Agroquimica y Tecnologia de Alimentos, Burjassot, Spain. Journal of Agricultural and Food Chemistry (2007), 55(14),
5512-5522. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN
Abstract
The time evolution of 2,2-diphenyl-1-picrylhydrazyl radical (DPPH.bul.) concn. in four solvents (methanol, ethanol, propanol, and
acetonitrile) during its redn. by three flavanones contg. an isolated p-catechol group (taxifolin, eriodyctiol, and fustin) as well as the
time evolution of the mass spectra of the reaction mixt. has been detd. by spectrophotometry and liq. mass spectrometry, resp. In
alc. solvents the redn. curves consisted of an initial short but fast kinetics step followed by a longer slow kinetics step; in contrast, in
acetonitrile the redn. curves completely lacked the slow kinetics step. From the results, a kinetic model for the reaction of redn. of the
DPPH.bul. by the isolated p-catechol group in flavanone type structures is proposed. According to this model, the p-catechol group
rapidly transfers two hydrogen atoms to DPPH.bul., through a fast rate const. k1, yielding the corresponding o-quinone. Then, the
intermediate o-quinone forms an adduct with the alc. solvent, through a slow rate const. k2, and regenerates the p-catechol group. The
regenerated p-catechol group reduces addnl. DPPH.bul. through a fast rate const. k3, yielding the corresponding o-quinone, which can
form a new adduct with the solvent to regenerate the p-catechol group, and so on. From the kinetics model, two explicit kinetics
equations have been derived that fit very well the exptl. data points acquired from all assayed compds. in all of the expts. carried out,
thus allowing an accurate detn. of the corresponding rate and stoichiometric consts.
Answer 210:
Relationship of structure and antioxidant activity of synthetic silybin- and isosilybin derived molecules: identification of
molecular structure responsible for antioxidant activity employing various models for inducing oxidative stress. Varga,
Zsuzsa; Nagy, Emoke; Katko, Monika; Jeney, Viktoria; Ujhelyi, Laszlo; Seres, Ildiko; Paragh, Gyorgy; Balla, Jozsef; Antus, Sandor.
Division of Nephrology, University of Debrecen, Hung. Editor(s): Panglossi, Harold V. New Developments in Antioxidants
Research (2006), 113-151. Publisher: Nova Science Publishers, Inc., Hauppauge, N. Y CODEN: 69JGNB Conference written in
Abstract
Natural non-enzymic-antioxidants (vitamin E, polyphenols and flavonoids) prevent overprodn. of reactive oxygen species playing
important role in oxidative-stress-mediated diseases. To improve potential use of natural compds. we need to explore mechanism of
their action. Structure-activity-relationship (SAR) of flavonoids was studied in details. However, only a few data are known regarding
SAR of flavonolignans such as (+)-silybin (1a,b). Previously, we demonstrated that (+)-silybin (1a,b) suppressed superoxide anion
prodn. (O2⋅-) prodn. in phorbol-myristate-acetate (PMA) stimulated polymorphonuclear leukocytes (PMNLs) via inhibition of protein
kinase C (PKC) activity and an increase in its lipid soly. (1a,b → 5a,b) improves its effect. Removal of 3'-methoxy-4'-hydroxyphenyl
and hydroxyl group at ring C of 1a,b resulting in flavanone derivs. did not modify, while introduction of a double bond in ring C
improved its inhibition on PMNLs. Silybum marianum contains beside (+)-silybin (1a,b), its regioisomer (+)-isosilybin (2a,b). Little is
known about the effect of this structural modification on the antioxidant activity of mol. Therefore, several flavanone and flavone
analogs of (+)-silybin (1a,b) and (+)-isosilybin (2a,b) were synthesized removal of 3'-methoxy-4'-hydroxyphenyl group at ring D and
flavanone
hydroxyl group at ring C of 1a,b and 2a,b resulted in flavanone derivs. of racemic (rac.-7 and -8) and optically active form [(-)-7 and
-8]; introduction of a double bond in rac.-7 and -8 served the corresponding flavone derivs. rac.-10 and -11, and basic skeleton (rac-9) -
and their antioxidant activities were compared. We found that both series of derivs. (rac.-7 vs. rac.-8, (-)-7 vs. (-)-8 and rac.-10 vs.
rac.-11) have almost same effects on O2⋅- prodn. in PMA-stimulated neutrophils, but flavone analogs (rac.-10, -11) have been found to
be more active ones via inhibition of PKC activity. The highest inhibition in PKC activity of PMA-stimulated neutrophils has been
obsd.
in case of the basic skeleton (rac.-9) of (+)-silybin (1a,b), suggesting that this skeleton is the binding site for PKC.
Inhibition of xanthine oxidase activity was the most pronounced in case of flavone analogs of 1a,b (rac.-10) and 2a,b
(rac.-11), and silybin-like derivs. were more potent than isosilybin-like ones. Silybin (1a,b), and flavone analogs of silybin
(rac.-10) and isosilybin (rac.-11) enhanced markedly oxidative resistance of LDL, and there were no differences between
the action of silybin and isosilybin analogs. In summary, these results suggest that different moieties of (+)-silybin
(1a,b) and (+)-isosilybin (2a,b) are responsible for the antioxidant action in PMA stimulated PMNLs, xanthine oxidase
activity, and LDL oxidn.
Answer 211:
Differential regulation of closely related R2R3-MYB transcription factors controls flavonol accumulation in different parts of
the Arabidopsis thaliana seedling. Stracke, Ralf; Ishihara, Hirofumi; Huep, Gunnar; Barsch, Aiko; Mehrtens, Frank; Niehaus,
Karsten; Weisshaar, Bernd. Department of Biology, Genome Research, Bielefeld University, Bielefeld, Germany. Plant Journal
(2007), 50(4), 660-677. Publisher: Blackwell Publishing Ltd., CODEN: PLJUED ISSN: 0960-7412. Journal written in English. CAN
Abstract
The genes MYB11, MYB12 and MYB111 share significant structural similarity and form subgroup 7 of the Arabidopsis thaliana
R2R3-MYB gene family. To det. the regulatory potential of these three transcription factors, we used a combination of genetic,
functional genomics and metabolite anal. approaches. MYB11, MYB12 and MYB111 show a high degree of functional similarity and
display very similar target gene specificity for several genes of flavonoid biosynthesis, including CHALCONE SYNTHASE,
CHALCONE ISOMERASE, FLAVANONE 3-HYDROXYLASE and FLAVONOL SYNTHASE1. Seedlings of the triple mutant myb11
myb12 myb111, which genetically lack a complete subgroup of R2R3-MYB genes, do not form flavonols while the accumulation of
anthocyanins is not affected. In developing seedlings, MYB11, MYB12 and MYB111 act in an additive manner due to their differential
spatial activity; MYB12 controls flavonol biosynthesis mainly in the root, while MYB111 controls flavonol biosynthesis primarily in
cotyledons. We identified and confirmed addnl. target genes of the R2R3-MYB subgroup 7 factors, including the
UDP-glycosyltransferases UGT91A1 and UGT84A1, and we demonstrate that the accumulation of distinct and structurally identified
flavonol glycosides in seedlings correlates with the expression domains of the different R2R3-MYB factors. Therefore, we refer to
these genes as PFG1-3 for 'Prodn. OF FLAVONOL GLYCOSIDES.
Answer 212:
Two new flavonoids from Bonannia graeca: a DFT-NMR combined approach in solving structures. Rosselli, Sergio; Bruno,
Maurizio; Maggio, Antonella; Bellone, Gabriella; Formisano, Carmen; Mattia, Carlo Andrea; Di Micco, Simone; Bifulco, Giuseppe.
Dipartimento di Chimica Organica, Universita di Palermo, Palermo, Italy. European Journal of Organic Chemistry (2007), (15),
2504-2510. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: EJOCFK ISSN: 1434-193X. Journal written in English.
Abstract
flavanone
Two new cyclized C-geranylated flavonoids, the dihydroflavonol bonanniol C and the flavanone bonannione B, were isolated as minor
compds. from the aerial parts. of B. graeca (Umbelliferae). Their structures were elucidated by a combined approach of extensive
spectroscopic means and quantum mech. methods.
Answer 213:
Capillary electrochromatography of selected phenolic compounds of Chamomilla recutita. Fonseca, Fabiana N.; Tavares,
Marina F. M.; Horvath, Csaba. Institute of Chemistry, University of Sao Paulo, Sao Paulo, SP, Brazil. Journal of
Abstract
This article explores the use of capillary electrochromatog. for the anal. of chamomile (Chamomilla recutita L.) exts. After a thorough
study of anal. parameters such as mobile and stationary phase compn., applied voltage, and temp., a methodol. to det. 11 bioactive
phenolic compds. (coumarins: herniarin, umbelliferone; phenylpropanoids: chlorogenic acid, caffeic acid; flavones: apigenin,
apigenin-7-O-glucoside, luteolin, luteolin-7-O-glucoside; flavonols: quercetin, rutin and flavanone: naringenin) in chamomile exts. was
proposed. The method was performed in a Hypersil SCX/C18 column with pH 2.8 phosphate buffer at 50 mmol L-1 contg. 50%
acetonitrile (pH adjusted before the addn. of the org. solvent). All compds. were sepd. in less than 7.5 min under isocratic conditions.
Figures of merit include linearity (peak area vs. apigenin concn.) from 50.0-1000 μg/mL (r2 = 0.995), and intra-day precision of
retention time and peak area better than 1.3% CV and 15%, resp. The limits of detection and quantification for apigenin were 35.0
μg/mL and 150.0 μg/mL, resp. This article also describes an NMR 1H study, carried out to monitor a new clean-up procedure for exts.
contg. propyleneglycol, whose components are poorly retained in conventional octadecyl silica cartridges.
Answer 214:
Extracting of total flavanone from Ficus benghalensis silk and its effect on scavenging of hydroxyl radicals. Huang, Suoyi;
Jiang, Lifang; Liu, Haihua; Li, Rong. Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Peop. Rep.
China. Huaxue Shijie (2006), 47(11), 689-691, 646. Publisher: Shanghaishi Huaxue Huagong Xuehui, CODEN: HUAKAB ISSN:
Abstract
In order to make use of the resources of Ficus benghalensis silk and to avoid wasting, the extn. of total flavanone of Ficus
benghalensis silk and its effects on scavenging of hydroxyl radicals were studied. The flavonoids were extd. using ethanol petroleum
ether or water as solvent from Ficus benghalensis silk under ultrasonic radiation. Using spectrophotometry to analyze the flavanone
of Ficus benghalensis silk, the d. of the total flavanone was 0.7240 mg/mL, 0.5962 mg/mL and 0.4529 mg/mL, resp., and the rate of
recovery were 101.0%, 99.8% and 100.9%. The rate of prodn. of ethanol extn. was the highest. The effect of the exts. on
scavenging of hydroxyl radicals was studied. This method is a purely phys. process and does not cause any pollution. It is an ideal
way to ext. the flavanone of Ficus benghalensis silk.
Answer 215:
Synthesis and antimicrobial activities of some new flavanones from 3,4-methylenedioxybenzaldehyde. Kadu, M. V.;
flavanone
Khadsan, R. E. Department of Applied Chemistry, Anuradha Engineering College, Chikhli, India. Journal of Ultra Scientist of
Physical Sciences (2007), 19(1), 89-92. Publisher: Journal of Ultra Scientist of Physical Sciences, CODEN: JUSPB3 Journal
Abstract
Some new flavanone derivs. have been prepd. by condensation of 1,3-propanediones with 3,4-methylenedioxybenzaldehyde (piperonal)
in alk. ethanol. The structures of these compds. have been confirmed by spectral anal. IR and NMR etc. The antimicrobial activities
of these compds. have been assessed against test organisms and were compared with std. drug chloramphenicol.
Answer 216:
Herbicidal activity of microbially produced flavanoids. Tao, Liming; Gu, Xuebin; Wang, Weijiong; Yang, Xing; Zhang, Yulian; Xu,
Wenping. Shanghai Pesticide Research Institute, Shanghai, Peop. Rep. China. Nongyao (2006), 45(3), 180-181, 203.
Publisher: Nongyao Bianjibu, CODEN: NONGFP ISSN: 1006-0413. Journal written in Chinese. CAN 148:208139 AN
Abstract
A Streptomyces strain, SPRI 94166, producing herbicidally active substances, was isolated from soil samples collected in Guangxi
Province. Based on morphol., physiol., and biochem. as well as mol. biol. characteristics, SPRI 94166 was identified as Streptomyces
lavendulae. Three active compds. were sepd. after isolation from the fermn. broth of strain SPRI 94166. Using NMR, and IR and
mass spectroscopy anal. methods, these compds. were identified as 4',5,7-trihydoxyisoflavone, flavanone and quercetin.
Answer 217:
Identification, property and biological activity of the pigments of harvested litchi fruit. Jiang, Yueming; Li, Jianrong; Zhao,
Mouming; Shi, John. South China Botanical Garden, Chinese Academy of Sciences, Guangzhou, Peop. Rep. China. Editor(s):
Benkeblia, Noureddine; Shiomi, Norio. Advances in Postharvest Technologies for Horticultural Crops (2006), 341-352. Publisher:
Research Signpost, Trivandrum, India CODEN: 69JFYJ Conference; General Review written in English. CAN 147:485110 AN
Abstract
A review. Litchi (Litchi chinensis Sonn.) is a tropical to subtropical crop that originates in South-east Asia. Litchi fruit pericarp tissue
contains large amt. of pigments which contribute the attractive red skin. However, the fruit lose rapidly the red color after harvest.
Postharvest handling has been emphasized on the control of the pigment degrdn. Storage of modified atmospheres in plastic bags and
sealed containers or controlled atmospheres has been reported to inhibit pigment degrdn. and reduce pericarp browning in litchi fruit.
The major pigments in ripe litchi fruit pericarp include flavonols, flavones, flavanones and anthocyanins. The major flavonoids are
detd. to be proanthocyanidin B4, proanthocyanidin B2 and epicatechin while cyanindin-3-rutinside, cyanidin-3-glucoside,
quercetin-3-rutinosde and quercetin-3-glucoside are identified as the important colored anthocyanins. Litchi pigments exhibit a strong
antioxidant capability. The hydroxyl radical and superoxide anion scavenging activities of proanthocyanidin B2 is greater than those of
proanthocyanidin B4 and epicatechin while the epicatechin has the highest DPPH scavenging activity. In similarity to the antioxidant
activity, litchi fruit pericarp ext. demonstrates a dose- and time-dependent inhibitory effect on human breast cancer. Furthermore, the
anti-cancer activities of epicatechin, proanthocyanidin B2, proanthocyanidin B4 and the Et acetate fraction from litchi pericarp tissues
are obsd. In in vitro trials of MCF-7 and HELF proliferation, proanthocyanidin B4 and the Et acetate fraction show a stronger inhibitory
flavanone
effect on HELF than MCF-7 while epicatechin and proanthocyanidin B2 have lower cytotoxicities to MCF-7 and HELF than paclitaxel.
It is suggested that the constituents from litchi fruit pericarp tissues might serve as a powerful novel anti-tumor agent but need to be
investigated further.
Answer 218:
Use of flavonoids and fruit acid as anti-viral compositions. Ripley, Ian. (UK). Brit. UK Pat. Appl. (2007), 9pp. CODEN:
BAXXDU GB 2432528 A 20070530 Patent written in English. Application: GB 2005-24375 20051129. Priority: . CAN 146:528354

GB 2432528 A 20070530 GB 2005-24375 20051129
GB 2005-24375 20051129
Abstract
The compn. comprises flavonoids, preferably flavanone glycosides (bioflavonoids) and fruit org. acids, preferably ascorbic, malic or
citric acids, which may be partially neutralised with 2-hydroxyethyltrimethyl ammonium hydroxide (choline) base. Preferably the
flavonoid and acid are dissolved in a non-toxic solvent mixt. comprising water and a co-solvent glycerin, polyhydric alcs. A preferred
embodiment comprises 15% sol. bioflavonoid, 15% citric acid, 15% malic acid, 5% ascorbic acid, 15% aq. soln. choline (45%n soln.),
15% glycerin, 20% water.
Answer 219:
New flavanone oligoglycosides, theaflavanosides I, II, III, and IV, with hepatoprotective activity from the seeds of tea plant
(Camellia sinensis). Li, Ning; Morikawa, Toshio; Matsuda, Hisashi; Ninomiya, Kiyofumi; Li, Xian; Yoshikawa, Masayuki. Kyoto
Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto, Japan. Heterocycles (2007), 71(5), 1193-1201. Publisher: Japan
Institute of Heterocyclic Chemistry, CODEN: HTCYAM ISSN: 0385-5414. Journal written in English. CAN 147:138396 AN
Abstract
Four new flavanone oligoglycosides, theaflavanosides I, II, III, and IV, were isolated from the seeds of C. sinensis. The structures of
theaflavanosides were elucidated on the basis of chem. and physicochem. evidence. Among them, theaflavanoside III was found to
show hepatoprotective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes.
Answer 220:
flavanone
Allergy-preventive flavonoids from Xanthorrhoea hastilis. Ogawa, Yuko; Oku, Hisae; Iwaoka, Emiko; Iinuma, Munekazu;
Ishiguro, Kyoko. School of Pharmaceutical Sciences, Mukogawa Women's University, 11-68 Koshien, Kyuban-cho, Nishinomiya,
Japan. Chemical & Pharmaceutical Bulletin (2007), 55(4), 675-678. Publisher: Pharmaceutical Society of Japan, CODEN:
CPBTAL ISSN: 0009-2363. Journal written in English. CAN 147:113847 AN 2007:562835 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Allergy-preventive activity was demonstrated for an ext. of resins from Xanthorrhoea hastilis R. BR. in a search for allergy-preventive
substances from natural sources. By bioassay-directed fractionation of this plant ext., a new flavanone,
3',5'-dihydroxy-7,4'-dimethoxyflavanone (1), and two new chalcones, 3,5,2'-trihydroxy-4,4'-dimethoxychalcone (2) and
5,2'-dihydroxy-3,4,4'-trimethoxychalcone (3), were isolated together with five known compds., 5'-hydroxy-7,3',4'-trimethoxyflavanone
(4), 3'-hydroxy-7,4'-dimethoxyflavanone (5), liquiritigenin 7-Me ether (6), 4,2'-dihydroxy-4'-methoxychalcone (7) and sakuranetin (8).
The structures of 1, 2 and 3 were elucidated by spectroscopic methods. All of these compds. showed allergy-preventive effects.
Answer 221:
Synthesis and Biological Evaluation of (±)-Abyssinone II and Its Analogues as Aromatase Inhibitors for Chemoprevention of
Breast Cancer. Maiti, Arup; Cuendet, Muriel; Croy, Vicki L.; Endringer, Denise C.; Pezzuto, John M.; Cushman, Mark. Department
of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy and Pharmaceutical Sciences, and The Purdue Cancer
Center, Purdue University, West Lafayette, IN, USA. Journal of Medicinal Chemistry (2007), 50(12), 2799-2806. Publisher:
American Chemical Society, CODEN: JMCMAR ISSN: 0022-2623. Journal written in English. CAN 147:166076 AN 2007:546064
Abstract
An efficient and economical synthesis of the naturally occurring aromatase inhibitor abyssinone II was performed. The synthesis
features an optimized arom. prenylation reaction in which an arylcopper intermediate is reacted with prenyl bromide to afford a key
intermediate that was converted to a prenylated arom. aldehyde. Condensation of the aldehyde with an o-hydroxyacetophenone under
Claisen-Schmidt conditions afforded a chalcone that was deprotected and cyclized in the presence of sodium acetate in refluxing
ethanol to afford (±)-abyssinone II. The synthesis proved to be versatile enough to provide an array of abyssinone II derivs. that
were evaluated as aromatase inhibitors. Methylation of the 4'-hydroxyl group of (±)-abyssinone II resulted in a significant increase in
aromatase inhibitory activity, and further smaller increases in activity resulted from the methylation of the 7-hydroxyl group and
removal of the prenyl side chain. As a result of these structural changes, the most active flavanone of the series (I) was 20 times
more potent than (±)-abyssinone II (IC50 40.95 μM).
OMe
MeO O
O I
Answer 222:
flavanone
Rapid qualitative and quantitative analyses of flavanone aglycons in Fructus aurantii by HPLC ion-trap MS. Zhou,
Da-yong; Xu, Qing; Xue, Xing-ya; Zhang, Fei-fang; Jing, Yu; Liang, Xin-miao. Dalian Institute of Chemical Physics, Chinese
Academy of Sciences, Dalian, Peop. Rep. China. Journal of Separation Science (2007), 30(6), 858-867. Publisher: Wiley-VCH
Verlag GmbH & Co. KGaA, CODEN: JSSCCJ ISSN: 1615-9306. Journal written in English. CAN 147:207715 AN 2007:541799
Abstract
IT-MS operated in the pos. mode was applied for the rapid characterization/quantification of the flavanones in exts. from Fructus
aurantii. APCI-MS and CID MS/MS provide unequivocal mol. wt. (MW) data of these compds. and useful information about their
structures (diagnostic fragment ions). Main fragment pathways include neutral losses of H2O, C2H2O, and B-ring as well as a
retro-Diels-Alder (RDA) fragment giving rise to [1,3A + H]+, [1,3B + H]+, and [1,4B-H2 + H]+ ions, which form the characteristic MS/MS
"fingerprint" of flavanone aglycons. When screening exts. of F. aurantii for flavanone aglycons, 8 target compds. were characterized
using this fingerprint. Meanwhile, ESI-MS in full-scan mode was developed and validated for the quantification of the main flavanone
aglycons in F. aurantii. This method is simple, accurate, fast and requires only 16 min per sample for direct detection and
quantification of naringenin and hesperetin. All the results and these characteristic fragments showed that the IT-MS is a powerful tool
for the structural characterization and quant. detn. of flavanone aglycons.
Answer 223:
Preparation of naringenin derivatives with selectivity on estrogen receptors. De Keukeleire, Denis; Roelens, Frederik;
Dhooge, Willem. (Universiteit Gent, Belg.). PCT Int. Appl. (2007), 54pp. CODEN: PIXXD2 WO 2007053915 A2 20070518
Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ,
EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS,
LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG,
SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE,
IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO
2006-BE121 20061109. Priority: EP 2005-447250 20051109. CAN 146:521587 AN 2007:538912 CAPLUS (Copyright (C) 2008

WO 2007053915 A2 20070518 WO 2006-BE121 20061109
WO 2007053915 A3 20070802
EP, OA
flavanone
EP 2005-447250 A 20051109
Abstract
Naringenin derivs., such as I [R8 = alkyl, alkenyl, alkynyl], with selective anti-estrogenic activity were prepd. for use in
pharmaceutical compns. for treatment of estrogen-dependent diseases or disorders, i.e. estrogen-deficiency dependent disorders and
diseases with excessive estrogen prodn. or conditions benefiting from modulated estrogen prodn., such as estrogen-dependent
cancers, endometriosis, gynecomastia, impaired hypothalamo-pituitary regulation of gonadal function and bone homeostasis. Thus,
flavanone I [R8 = (CH2)6Me] was prepd. via a seven step synthetic sequence starting from hexyllithium or hexylmagnesium bromide,
2,4,6-trimethoxybenzaldehyde, acetyl chloride and 4-(methoxymethoxy)benzaldehyde. The prepd. naringenin derivs. were assayed for
α- and β-estrogen receptor agonist/antagonist activity and for effect on bone mineral d. and uterus wt. in ovariectomized rats.
OH
R8
HO O
HO O I
Answer 224:
Synthesis of flavanone inhibitors of FtsZ as antibiotics. Shaw, Jared; Urgaonkar, Sameer; Raychaudhuri, Debabrata; La Pierre,
Henry. (President and Fellows of Harvard College, USA). PCT Int. Appl. (2007), 129pp. CODEN: PIXXD2 WO 2007056188 A1
20070518 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE,
DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC,
LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC,
SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR,
GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English.
Application: WO 2006-US43042 20061103. Priority: US 2005-733543 20051104. CAN 146:521598 AN 2007:537785 CAPLUS

WO 2007056188 A1 20070518 WO 2006-US43042 20061103
flavanone
US 2005-733543P P 20051104
Abstract
Polyphenol compds. of formula I [R1-R4 = H, halo, cycloalkyl, alkyl, acyl, aryl, etc.; R5, R6 = absent, H, halo, alkyl, etc.; P = H,
alkyl, protecting group, acyl, aryl, etc.] are prepd. which inhibit the GTPase activity of FtsZ. These compds. are useful in treating
infections, particularly infections caused by gram-pos. organisms. Methods of prepg. the inventive compds. are also provided. The
compds. are prepd. by the benzylation of pinocembrin or chrysin core structure. Pharmaceutical compns. and method of using the
compds. to treat disease are also provided. These compds. may be screened for antimicrobial activity as well as other biol. activities
such as anti-neoplastic, anti-inflammatory, immunosuppressive, and cytotoxic activity. Thus, (±)-2'''-hydroxy-5''-benzylisouvarinol-B
(II) was prepd., and had IC50 value of 8.3 μM for inhibition of E. coli FtsZ GTPase activity.
HO HO
R1
R5
PO O R3 OH HO O Ph
R2 R4
R6
OP O I OH OH O II
Answer 225:
Peroxisome proliferator-activated receptor activators, and skin compositions containing the same. Nanami, Yoshihiko; Ito,
Kenichi; Idamarcoda, Alnasili. (Ichimaru Pharcos Inc., Japan). Jpn. Kokai Tokkyo Koho (2007), 34pp. CODEN: JKXXAF JP
2007119429 A 20070517 Patent written in Japanese. Application: JP 2005-317153 20051031. Priority: . CAN 146:467928 AN

JP 2007119429 A 20070517 JP 2005-317153 20051031
JP 2005-317153 20051031
Abstract
The invention provides a peroxisome proliferator-activated receptor (PPAR) β/δ activator, characterized by contg. a flavone, flavonol,
flavanone
flavanone, flavanol, and/or isoflavone as an active component, wherein the PPAR β/δ-activator is suitable for use in a skin compn. for
prevention and treatment of rough skin, skin inflammation, and decrease of skin barrier function. For example, the effect of luteolin
on PPAR β/δ activation was in vitro tested. Also, a cosmetic emulsion contg. rhoifolin 0.1 % was formulated.
Answer 226:
Modified aromatic ring dioxygenase and uses in production of hydroxylated flavones. Kagami, Osamu; Misawa, Norihiko;
Shindo, Kazutoshi. (Marine Biotechnology Institute, Japan). Jpn. Kokai Tokkyo Koho (2007), 27pp. CODEN: JKXXAF JP

JP 2007116975 A 20070517 JP 2005-313177 20051027
JP 2005-313177 20051027
Abstract
Provided is a method for introducing hydroxyl group into the Ph group (benzene ring) of a flavones compd. and producing hydroxylated
flavones. A hydroxylated flavone compd. is a diol body where two hydroxyl groups are introduced into position 2 and 3 of the Ph
group of a flavone chem. compd. The method comprises the following steps: (a) transformation of a vector carrying a modified arom.
ring dioxygenase gene (modified BphA) and dihydrodiol dehydrogenase gene (BphB) into a microorganism; (b) expression of modified
BphA and BphB in the microorganism; (c) prodn. of hydroxylated flavones by adding at least one of the culture products of the
microorganism to a sample contg. flavones compd., mixing or cultivating, and obtaining the hydroxylated flavones compd. from the
mixt. or culture products. The modified arom. ring dioxygenase has mutations at position 324-325 introduced by mutagenesis. The
sequences of two arom. ring dioxygenase mutants are provided.
Answer 227:
Large-pore cubic Ia-3d mesoporous silicas: Synthesis, modification and catalytic applications. Huang, Jiahui; Tian, Ge;
Wang, Hongsu; Xu, Ling; Kan, Qiubin. Department of Chemistry, Jilin University, Changchun, Peop. Rep. China. Journal of
Molecular Catalysis A: Chemical (2007), 271(1-2), 200-208. Publisher: Elsevier B.V., CODEN: JMCCF2 ISSN: 1381-1169. Journal
Abstract
Large-pore cubic Ia-3d mesoporous silicas were synthesized by co-condensation of tetraethoxysilane (TEOS) and a small amt. of
phenyltriethoxysilane (PTES) under acidic conditions using triblock copolymer P123 (EO20PO70EO20) as the template. In the
synthesis procedure, the amt. of PTES added in the range of 3.0-10% was very vital for the formation of the ordered Ia-3d structure.
In addn., the prehydrolysis of PTES prior to TEOS in the template soln. was also important for the prepn. of ordered Ia-3d materials. If
TEOS was prehydrolyzed, ordered 2d-hexagonal materials were obtained. After mild calcination at 250° to selectively remove the
flavanone
template, Ia-3d and 2d-hexagonal materials with 10% PTES were selected to be sulfonated to introduce sulfonic acid sites into the
channels. Both Ia-3d and 2d-hexagonal mesoporous sulfonic acid catalysts can effectively catalyze the liq. phase condensation
reaction of phenol with acetone to Bisphenol A. The catalytic activity of the Ia-3d catalyst was slightly higher than that of the
2d-hexagonal one. Addnl., after calcination at 550 °C to remove the template and Ph groups, Ia-3d mesoporous materials with
different pore sizes (3.8-6.8 nm) were further functionalized with amino groups by postsynthesis grafting. It was found that in the
synthesis of flavanone the catalytic performance of amino-functionalized Ia-3d mesoporous base catalysts increased with the
increase in their pore sizes.
Answer 228:
Cotton flavonoid structural genes related to the pigmentation in brown fibers. Xiao, Yue-Hua; Zhang, Zheng-Sheng; Yin,
Meng-Hui; Luo, Ming; Li, Xian-Bi; Hou, Lei; Pei, Yan. Key Laboratory of Biotechnology and Crop Quality Improvement of the Ministry
of Agriculture, Peop. Rep. China. Biochemical and Biophysical Research Communications (2007), 358(1), 73-78. Publisher:
Elsevier, CODEN: BBRCA9 ISSN: 0006-291X. Journal written in English. CAN 147:113929 AN 2007:523867 CAPLUS
Abstract
Five flavonoid structural genes, encoding chalcone isomerase, flavanone 3-hydroxylase, dihydroflavonol 4-reductase, anthocyanidin
synthase, and anthocyanidin reductase, were cloned from a brown-fiber cotton line (T586). The predicted proteins of these genes
exhibit high sequence similarity with corresponding enzymes from various plants. RT-PCR anal. showed these genes are
developmentally co-regulated and preferentially expressed in developing fibers of T586. Expression analyses and
dimethylaminocinnaldehyde staining demonstrated that high transcript levels of these genes in developing fibers and presence of
proanthocyanidins in mature fibers co-segregated with brown fiber in a recombination inbred line population. Our results indicated that
the cloned flavonoid structural genes and proanthocyanidins were involved in the pigmentation in brown cotton fibers.
Answer 229:
Stimulation of the phenylpropanoid biosynthesis by plant activators in apple leaves. Strissel, T.; Hoyer, U.; Zistler, C.;
Treutter, D.; Halbwirth, H.; Stich, K. Weihenstephan Chair of Fruit Science, Technical University Munich, Freising, Germany.
Acta Horticulturae (2007), 732(Proceedings of the VIIIth International Symposium on Canopy, Rootstocks and Environmental
Physiology in Orchard Systems, 2004), 549-554. Publisher: International Society for Horticultural Science, CODEN: AHORA2 ISSN:
Abstract
The present work studied the influence of the plant activators Biokal 01, Milsana VP 2001, potassic silicate and SilKaBen on the
phenylpropanoid metab. of apple leaves. Chem. anal. and detn. of enzyme activities were carried out in leaves of the scab
susceptible apple cv. 'Golden Delicious' and the scab resistant cv. 'Rewena'. The activity of several enzymes of the flavonoid
biosynthesis [phenylalanine ammonia lyase (PAL), chalcone synthase/-isomerase (CHS/CHI), flavanone 3-hydroxylase (FHT) and
dihydroflavonol 4-reductase (DFR)] was detd. An increasing activity of these enzymes did not stringently cause higher contents of
phenylpropanoids. However, changes in the phenylpropanoid content of the apple leaves were related to changes at the enzyme level.
Effects of enzyme stimulation could be obsd. within the first 3 days after application of activating reagents. The phenylpropanoid
metab. was induced faster and stronger in young leaves than adult ones. Changes in the phenylpropanoid metab. could be found at all
times tested within 4 h to 3 days.
Answer 230:
flavanone
The tumor-growth inhibitory activity of flavanone and 2'-OH flavanone in vitro and in vivo through induction of cell cycle
arrest and suppression of cyclins and CDKs. Hsiao, Yung-Chin; Hsieh, Yih-Shou; Kuo, Wu-Hsien; Chiou, Hui-Ling; Yang,
Shun-Fa; Chiang, Whei-Ling; Chu, Shu-Chen. Institute of Biochemistry and Biotechnology, Chung Shan Medical University,
Taichung, Taiwan. Journal of Biomedical Science (Dordrecht, Netherlands) (2007), 14(1), 107-119. Publisher: Springer, CODEN:
JBCIEA ISSN: 1021-7770. Journal written in English. CAN 148:69416 AN 2007:491606 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
Natural products, including flavonoids, are suggested to be involved in the protective effects of fruits and vegetables against cancer.
However, studies concerning the effect of flavonoids frequently lacked data regarding to flavanones. In this study, we investigated
the inhibitory effect of flavanone compds., including flavanone, 2'-OH flavanone, 4'-OH flavanone, 6-OH flavanone, naringin and
naringenin, on cell growth of various cancer cells. We detd. that flavanone and 2'-OH flavanone inhibited cell growth of A549, LLC,
AGS, SK-Hep1 and HA22T cancer cells, while other flavanones showed little or no inhibition. We evaluated growth-inhibitory activity of
flavanone and 2'-OH flavanone against highly proliferative human lung cancer cells (A549) via anchorage-independent and -dependent
colony formation assay, and further showed that treatment of flavanone resulted in a G1 cell cycle arrest with redn. of cyclin D, E and
cyclin-dependent kinase (CDK) 2, while treatment of 2'-OH flavanone led to a G2/M phase accumulation with redn. of cyclin B, D and
Cdc2. Moreover, we demonstrated the improvement effect of flavanone and 2'-OH flavanone with anti-cancer drug, doxorubicin, on
A549 cells. Finally, flavanone and 2'-OH flavanone were evidenced by its inhibition on the growth of A549 and Lewis lung carcinoma
cells in vivo.
Answer 231:
Super/subcritical fluid chromatography separations with four synthetic polymeric chiral stationary phases. Han, X.;
Berthod, A.; Wang, C.; Huang, K.; Armstrong, D. W. Department of Chemistry, University of Texas at Arlington, Arlington, TX,
USA. Chromatographia (2007), 65(7/8), 381-400. Publisher: Vieweg Verlag/GWV Fachverlage GmbH, CODEN: CHRGB7 ISSN:
Abstract
New synthetic polymeric chiral selectors were developed recently as chiral stationary phases. They were tested with supercrit. fluid
mobile phases made of CO2 plus an alc. modifier and 0.2% vol./vol. trifluoroacetic acid. The polymeric
N,N'-(1S,2S)-1,2-cyclohexanediyl-bis-2-propenamide (P-CAP), the polymeric N,N'-[(1R,2R)-1,2-diphenyl-1,2-ethanediyl]
bis-2-propenamide (P-CAP-DP), the polymeric trans-9,10-dihydro-9,10-ethanoanthracene-(11S,12S)-11,12-dicarboxylic acid
bis-4-vinylphenylamide (DEABV) and the polymeric N,N'-[(1R,2R)-1,2-diphenyl-1,2-ethanediyl] bis-4-vinylbenzamide (DPEVB) were
bonded to 5 μm silica particles and used to prep. four columns that were tested with a set of 88 chiral compds. with a wide variety of
chem. functionalities. All 88 test compds. were sepd. on one or more of these related polymeric CSPs. Forty-three enantiomeric pairs
were sepd. in SFC conditions by only one of the CSPs. Twenty pairs were sepd. by two CSPs and 18 and 7 enantiomeric pairs were
sepd. by 3 and all 4 CSPs, resp. The three P-CAP, P-CAP-DP and DEABV CSPs have equiv. success being able to sep. 49
enantiomeric pairs of the studied set with resp. 12, 14 and 20 at baseline (Rs > 1.5). The DPEVB CSP was significantly less efficient
sepg. only 18 chiral compds. with only one at baseline. The great advantage of the SFC mobile phases is the rapid sepn., witch most
achieved in <5 min.
Answer 232:
flavanone
Total, cumulative fast-kinetics and cumulative slow-kinetics antiradical activities of juices from clementine (Citrus
clementina), clementine-hybrids and satsuma (Citrus unshiu) cultivars and their utility as discriminant variables.
Sentandreu, Enrique; Izquierdo, Luis; Sendra, Jose M. Instituto de Agroquimica y Tecnologia de Alimentos, Valencia, Spain.
European Food Research and Technology (2007), 225(2), 271-278. Publisher: Springer GmbH, CODEN: EFRTFO ISSN: 1438-2377.
Abstract
Mandarin juices from three pure clementine (Citrus clementina Hort. ex Tan.) cultivars: Clemenules, Hernandine and Marisol, two
clementine-hybrid cultivars: Nova (clementine × tangelo Orlando) and Fortune (clementine × mandarin Dancy), one mandarin-hybrid
cultivar: Ortanique (mandarin × orange) and one satsuma (Citrus unshiu Marc) cultivar: Clauselline have been analyzed for detn. of
total, cumulative fast-kinetics and cumulative slow-kinetics antiradical activities. Total antiradical activity followed the order: pure
clementine and Nova > Ortanique > Fortune and Clauselline. Cumulative fast-kinetics antiradical activity was the major contributor to
total antiradical activity, accounting for about 87% as av. Ascorbic acid content was the major contributor to cumulative fast-kinetics
antiradical activity, accounting for about 93.5% as av. A weak correlation (r2 = 0.151) between total flavanone-7-O-glycosides (FGs,
Narirutin, Hesperidin and Didymin) content and cumulative slow-kinetics antiradical activity was obsd. However, ascorbic acid and
total FGs contents showed a significant neg. correlation (r2 = 0.658). By using the cumulative fast-kinetics and slow-kinetics
antiradical activities as variables, all the assayed juices were significantly discriminated (<0.05) by statistical multivariate discriminant
anal.
Answer 233:
Two new flavanone glycosides of Jasminum lanceolarium and their anti-oxidant activities. Sun, Jia-Ming; Yang, Jun-Shan;
Zhang, Hui. Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College,
Beijing, Peop. Rep. China. Chemical & Pharmaceutical Bulletin (2007), 55(3), 474-476. Publisher: Pharmaceutical Society of
Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN 147:113819 AN 2007:483227 CAPLUS
Abstract
Two new flavanone glucosides, (2S)-5,7,3',5'-tetrahydroxy-flavanone 7-O-β-D-allopyranoside (1) and

(2S)-5,7,3',5'-tetrahydroxy-flavanone 7-O-β-D-glucopyranosine (2) were isolated from the stems and leaves of Jasminum lanceolarium,
along with five known compds.: Betulinaldehyde (3), betulinic acid (4), betulin (5), syringin (6) and Liriodendrin (7). Their structures were
detd. on the basis of spectroscopic and chem. methods. The isolated compds. were screened for their in vitro antioxidant activity
through DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging assay. Compds. 2 demonstrated significant radical scavenging
activity.
Answer 234:
Secondary metabolites from Andrographis paniculata. Li, Wenkui; Xu, Xudong; Zhang, Hongjie; Ma, Cuiying; Fong, Harry; van
Breemen, Richard; Fitzloff, John. Department of Medicinal Chemistry and Pharmacognosy (m/c 781), University of Illinois at
Chicago, Chicago, IL, USA. Chemical & Pharmaceutical Bulletin (2007), 55(3), 455-458. Publisher: Pharmaceutical Society of
Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN 147:113817 AN 2007:483221 CAPLUS
Abstract
flavanone
Two new flavonoid glycosides, 5-hydroxy-7,8-dimethoxy (2R)-flavanone-5-O-β-D-glucopyranoside (1) and

5-hydroxy-7,8,2',5'-tetramethoxy-flavone-5-O-β-D-glucopyranoside (2), and a new diterpenoid, androg. acid (3), along with
andrographidin A (4) were isolated from Andrographis paniculata, and their structures were detd. on the basis of physicochem. and
spectroscopic anal. Compd. 3 was evaluated for cytotoxicity to KB cells along with andrographolide, isoandrographolide,
neoandrographolide and 14-deoxy-11,12-didehydroandrographolide obtained from A. paniculata in the present study. Cytotoxicity was
obsd. for andrographolide and isoandrographolide with ED50 values of 6.5 and 5.1 μg/mL, resp.
Answer 235:
Chemical structure-dependent differential effects of flavonoids on the catalase activity as evaluated by a chemiluminescent
method. Doronicheva, Nataliya; Yasui, Hiroyuki; Sakurai, Hiromu. Department of Analytical and Bioinorganic Chemistry, Kyoto
Pharmaceutical University, 5 Nakauchi-cho, Misasagi, Yamashina-ku, Kyoto, Japan. Biological & Pharmaceutical Bulletin (2007),
30(2), 213-217. Publisher: Pharmaceutical Society of Japan, CODEN: BPBLEO ISSN: 0918-6158. Journal written in English. CAN
Abstract
The antioxidative activity of flavonoids depends upon a combination of many factors, such as the concn. and chem. structure of the
flavonoids and the arrangement of functional groups in their structure. In the present study, to evaluate the antioxidative effect of
several types of flavonoids on catalase activity at a physiol. H2O2 concn., a chemiluminescent (CL) method was used. The
H2O2/luminol-dependent CL intensity in a system contg. 3.7 nM catalase and low concns. (10-100 nM) of green tea flavanols
(epigallocatechin gallate; EGCG and epicatechin gallate; EG) was enhanced in comparison with that of a system without catalase,
suggesting that EGCG and EG partially suppressed catalase activity. On the other hand, flavone and flavonols such as rutin (a
3-glycosidic flavone), quercitrin (a 3-glycosidic flavonol), myricetin, and kaempferol (flavonols), resp., lowered the CL intensity to a
greater extent at low concns. (<0.1 μM) when catalase was present than when catalase was absent, indicating that these flavonoids
activate catalase. In addn., isoflavone and flavanone such as daidzein and naringenin, resp., exhibited weak antioxidative activities
against H2O2 without any effect on the catalase activity over a wide range of flavonoid concns. (0.04-0.4 μM). From these results, it
was for the first time suggested that the binding of flavonoids to the heme moiety or a protein region of catalase contributes to the
enhancement of catalase activity.
Answer 236:
A new bioactive prenylated dihydroflavanoid from Dolichos tenuicaulis (Baker) Craib. Peng, Jin Yong; Liu, Hai Yan; Qi, Yan;
Han, Xu; Xu, You Wei; Xu, Li Na; Xu, Qi Wei. School of Pharmacy, Dalian Medical University, Dalian, Peop. Rep. China.
Chinese Chemical Letters (2007), 18(3), 293-296. Publisher: Chinese Chemical Society, CODEN: CCLEE7 ISSN: 1001-8417.
Abstract
A new prenylated dihydroflavonoid was obtained from the root of Dolichos tenuicaulis (Baker) Craib. The structure was elucidated as
(2S)-5,2',6'-trihydroxy-3''',8-di(γ,γ-dimethylallyl)-2''',2'''-dimethylpyrano[5''',6''':6,7]-2''''',4'''''-cyclohexadiene-1'''''-one[2''''',3''''':3',4']flavan
one, named dolichnin A, by spectroscopic methods including UV, IR, HR-EI-MS, 1D NMR and 2D NMR techniques, and subsequently,
the anticancer activity of this compd. to inhibit human cancer cells' growth including A549, BEL-7402, Hep-3B, SMMC7721, HT-29,
MCF-7, SGC-7902, K562, A498 and PC3 cell lines by MTT method was evaluated in vitro.
Answer 237:
flavanone
Recovery of anthocyanins, flavanones and sugars from by-products of pigmented orange processing. Scordina, Monica; Di
Mauro, Alfio; Passerini, Amedeo; Maccarone, Emanuele. Dipartimento di OrtoFloroArboricoltura e Tecnologie Agroalimentari
(DOFATA), Tecnologie Agroalimentari, Universita degli Studi di Catania, Catania, Italy. Ingredienti Alimentari (2007), 6(1), 23-31.
Publisher: Chiriotti Editori sas, CODEN: IANLBJ ISSN: 1594-0543. Journal written in Italian. CAN 147:141802 AN 2007:474864
Abstract
Pigmented orange pulp wash, a liq. byproduct of citrus processing, was used to obtain alc. ext. of anthocyanins and
hydroxycinnamates, flavanones, and purified sugar conc. by a series of resin adsorptions and membrane techniques. The final
products and the intermediates were characterized by chem. and microbiol. methods. The anthocyanins, limonoids, flavanones, and
hydroxycinnamates were fully removed by a neutral polystyrene-divinylbenzene resin and could be selectively recovered by using
appropriate solvents as eluents; they could be used as ingredients in dietary supplements and/or as raw materials in cosmetic,
pharmaceutical, and nutraceutical prepns. The acidity of the decolored eluate was diminished by weakly basic ion-exchange matrix,
while the ultrafiltration process stabilized the product by removal of enzymes and microorganisms. Reverse osmosis treatment
removed 80% of water and increased the sugar concn. 4-times. The final product with 28°Brix sol. solids contained .apprx.250 g
sugars (glucose, fructose, sucrose), .apprx.9 g citric acid, and 1 g pectins per L. The conc. was a transparent liq. of slight amber color
with very low microbial count. It may be used as a natural sweetener in foods and beverages.
Answer 238:
A flavanone and other constituents of the Brazilian endemic species Trembleya laniflora (D. Don) Cogn. (Melastomataceae)
[Biochemical Systematics and Ecology 35(2007) 40-41]. Ventura, Claiton Pires; Dias de Souza Filho, Jose; Braga de Oliveira,
Alaide; Braga, Fernao Castro. Faculdade de Farmacia, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil. Biochemical
Systematics and Ecology (2007), 35(7), 472. Publisher: Elsevier Ltd., CODEN: BSECBU ISSN: 0305-1978. Journal; Miscellaneous
Answer 239:
Phytochemical genomics in Arabidopsis thaliana: a case study for functional identification of flavonoid biosynthesis genes.
Tohge, Takayuki; Yonekura-Sakakibara, Keiko; Niida, Rie; Watanabe-Takahashi, Akiko; Saito, Kazuki. RIKEN Plant Science Center,
1-7-22, Suehiro-cho, Tsurumi-ku, Yokohama-shi, Kanagawa, Japan. Pure and Applied Chemistry (2007), 79(4), 811-823. Publisher:
International Union of Pure and Applied Chemistry, CODEN: PACHAS ISSN: 0033-4545. Journal written in English. CAN
Abstract
The completion of the whole genome sequence of Arabidopsis thaliana has made it possible to explore the phytochem. genomics in this
species by detg. gene-to-metabolite correlation through the comprehensive anal. of metabolite accumulation and gene expression. In
this study, flavonoid profiling of wild-type plants and T-DNA insertion mutants was analyzed using ultra-performance liq. chromatog.
(UPLC)/photodiode array detection (PDA)/electrospray ionization (ESI)/multiple-stage mass spectrometry (MSn). Detailed anal. of the
metabolite changes in the mutants suggested the functions of genes that have been mutated. In silico coexpression anal. of genes
involved in flavonoid metab. in Arabidopsis was performed using a publicly available transcriptome database of DNA microarrays. We
flavanone
inferred a coexpression framework model of the genes involved in the pathways of flavonol, anthocyanin, and proanthocyanidin
synthesis, suggesting specific functions and coregulation of the genes of pathway enzymes and transcription factors. The metabolic
profiling of the omt1 mutant lacking a methyltransferase gene narrowed down by the coexpression anal. showed that AtOMT1
(At5g54160) is involved not only in the prodn. of lignins and sinapoyl esters but also in the methylation of flavonols forming
isorhamnetin. These results suggest that the functional genomics approach by detailed target-metabolite profiling with transcriptome
coexpression anal. provides an efficient way of identifying novel gene functions involved in plant metab.
Answer 240:
Chemopreventive effect of naringin on the benzo(a)pyrene-induced forestomach carcinoma in mice. Jagetia, Ganesh
Chandra; Reddy, Tiyyagura Koti. Department of Radiobiology, Kasturba Medical College, Manipal, India. International Journal of
Cancer Prevention (2004), 1(6), 429-444. Publisher: Nova Science Publishers, Inc., CODEN: IJCPC6 ISSN: 1554-1134. Journal
Abstract
The chemopreventive activity of 1, 2.5, 5, 10, 25, 50, 100 or 250 mg/kg b. wt. naringin, a citrus flavanone was studied on the
benzo(a)pyrene (BaP)-induced forestomach carcinoma in female Swiss albino mice. Naringin was given before, after or both (before &
after) orally or i.p. to mice receiving BaP for the induction of chem. carcinogenesis. The optimum chemopreventive dose was found to
be 10 mg/kg p.o. and oral administration was more effective than the i.p. treatment. A max. chemopreventive activity of naringin was
obsd. when it was given during and after the termination of BaP treatment. The tumor incidence and tumor multiplicity were reduced in
a dose dependent manner, and highest redn. of 78% in tumor multiplicity was obsd. at 10 mg/kg, where a 20% redn. in tumor incidence
was also obsd. However, a reduced chemopreventive effect was obsd. when naringin was given either before or after chem. induced
carcinogenesis. These observations were further confirmed by PCNA labeling where naringin pretreatment reduced the PCNA labeling
index by four folds. The micronuclei anal. in splenocytes also confirms to the chemopreventive activity of naringin. BaP treatment
increased the frequency of micronuclei bearing splenocytes (MNBNC) by six folds. Naringin treatment during and after BaP
administration reduced the frequency of MNBNC in a dose dependent manner up to 10 mg/kg where a highest redn. in MNBNC was
obsd., thereafter the frequency of MNBNC showed a marginal increase up to a dose of 250 mg/kg naringin however it was two folds
lower than BaP treatment alone. A similar effect on MNBNC decline was obsd. for pre or post-naringin treated group however, the
degree of decline in MNBNC was lesser when compared to pre-post naringin treatment. Our study demonstrates, that the naringin
possesses chemopreventive activity and this may be due to redn. in DNA damage as evidenced by lower frequency of MNBNC in the
group treated with naringin during and after chem. carcinogenesis.
Answer 241:
Naringin, a grapefruit flavanone, protects V79 cells against the bleomycin-induced genotoxicity and decline in survival.
Jagetia, Abhinav; Jagetia, Ganesh Chandra; Jha, Shalini. Department of Metallurgy, Malviya National Institute of Technology,
Jaipur, India. Journal of Applied Toxicology (2007), 27(2), 122-132. Publisher: John Wiley & Sons Ltd., CODEN: JJATDK ISSN:
Abstract
The effect of naringin, a grapefruit flavanone was studied on bleomycin-induced genomic damage and alteration in the survival of
cultured V79 cells. Exposure of V79 cells to bleomycin induced a concn. dependent elevation in the frequency of binucleate cells
bearing micronuclei (MNBNC) and a max. no. of MNBNCs were obsd. in the cells treated with 50 μg ml-1 bleomycin, the highest concn.
evaluated. This genotoxic effect of bleomycin was reflected in the cell survival, where a concn. dependent decline was obsd. in the
cells treated with different concns. of bleomycin. Treatment of cells with 1 mM naringin before exposure to different concns. of
flavanone
bleomycin arrested the bleomycin-induced decline in the cell survival accompanied by a significant redn. in the frequency of
micronuclei when compared with bleomycin treatment alone. The cell survival and micronuclei induction were inversely correlated. The
repair kinetics of DNA damage induced by bleomycin was evaluated by exposing the cells to 10 μg ml-1 bleomycin using single cell
gel electrophoresis. Treatment of V79 cells with bleomycin resulted in a continuous increase in DNA damage up to 6 h post-bleomycin
treatment as evident by migration of more DNA into the tails (% tail DNA) of the comets and a subsequent increase in olive tail
moment (OTM), an index of DNA damage. Treatment of V79 cells with 1 mM naringin reduced bleomycin-induced DNA damage and
accelerated DNA repair as indicated by a redn. in % tail DNA and OTM with increasing assessment time. A max. redn. in the DNA
damage was obsd. at 6 h post-bleomycin treatment, where it was 5 times lower than bleomycin alone. Our study, which was conducted
on the basis of antioxidant, free radical scavenging and metal chelating properties of naringin demonstrates that naringin reduced the
genotoxic effects of bleomycin and consequently increased the cell survival and therefore may act as a chemoprotective agent in
clin. situations.
Answer 242:
Effect of flavonoids on glutathione level, lipid peroxidation and cytochrome P450 CYP1A1 expression in human laryngeal
carcinoma cell lines. Durgo, Ksenija; Vukovic, Lidija; Rusak, Gordana; Osmak, Maja; Colic, Jasna Franekic. Faculty of Food
Technology and Biotechnology, University of Zagreb, Zagreb, Croatia. Food Technology and Biotechnology (2007), 45(1), 69-79.
Publisher: University of Zagreb, Faculty of Food Technology and Biotechnology, CODEN: FTBRFD ISSN: 1330-9862. Journal
Abstract
Flavonoids are phytochems. exhibiting a wide range of biol. activities, among which are antioxidant activity, the ability to modulate
activity of several enzymes or cell receptors and possibility to interfere with essential biochem. pathways. Using human laryngeal
carcinoma HEp2 cells and their drug-resistant CK2 subline, we examd. the effect of five flavonoids, three structurally related flavons
(quercetin, fisetin, and myricetin), one flavonol (luteolin) and one glycosylated flavanone (naringin) for: (i) their ability to inhibit
mitochondrial dehydrogenases as an indicator of cytotoxic effect, (ii) their influence on glutathione level, (iii) antioxidant/prooxidant
effects and influence on cell membrane permeability, and (iv) effect on expression of cytochrome CYP1A1. Cytotoxic action of the
investigated flavonoids after 72 h of treatment follows this order: luteolin>quercetin>fisetin>naringin>myricetin. Our results show that
CK2 were more resistant to toxic concns. of flavonoids as compared to parental cells. Quercetin increased the total GSH level in both
cell lines. CK2 cells are less perceptible to lipid peroxidn. and damage caused by free radicals. Quercetin showed prooxidant effect in
both cell lines, luteolin only in HEp2 cells, whereas other tested flavonoids did not cause lipid peroxidn. in the tested cell lines. These
data suggest that the same compd., quercetin, can act as a prooxidant, but also, it may prevent damage in cells caused by free
radicals, due to the induction of GSH, by forming less harmful complex. Quercetin treatment damaged cell membranes in both cell
lines. Fisetin caused higher cell membrane permeability only in HEp2 cells. However, these two compds. did not enhance the damage
caused by hydrogen peroxide. Quercetin, naringin, myricetin and fisetin increased the expression of CYP1A1 in both cell lines, while
luteolin decreased basal level of CYP1A1 only in HEp2 cells. In conclusion, small differences in chem. structure of flavonoids led to
drastic change of their biol.
effects.
Answer 243:
In vivo metabolic effects of naringenin in the ethanol consuming rat and the effect of naringenin on adipocytes in vitro.
Szkudelska, K.; Nogowski, L.; Nowicka, E.; Szkudelski, T. Department of Aninal Physiology and Biochemistry, University of
Agriculture, Poznan, Pol. Journal of Animal Physiology and Animal Nutrition (2007), 91(3-4), 91-99. Publisher: Blackwell Verlag
GmbH, CODEN: JAPNEF ISSN: 0931-2439. Journal written in English. CAN 147:159813 AN 2007:451913 CAPLUS
flavanone
Abstract
Naringenin is a bioactive flavanone involved in the inhibition of drug metab. which exhibits antioxidant, anti-inflammatory and
anticancerogenic properties and which recently appeared to be a factor mitigating the hyperlipidemic effects in rats and rabbits. In the
performed expt., the effect of naringenin, administered intragastrically (50 mg/kg) for 2 wk to normal and ethanol drinking rats, on
insulin and leptin levels and on some metabolic parameters was investigated. Naringenin did not change the hormone levels in any
group of rats. Blood glucose, triglyceride, total, esterified and free cholesterol and high-d. lipoprotein-cholesterol concns. were also
unaffected by this compd. Only free fatty acids were elevated after the naringenin treatment in the water-drinking rats. In spite of
unchanged glucose and insulin concns. in blood, the tested flavanone reduced the glucose/insulin ratio in ethanol-receiving rats. Liver
triglycerides, elevated due to ethanol ingestion, were partially normalized by naringenin. Other tested parameters like liver glycogen
and cholesterol, muscle triglycerides and glycogen were not altered in any group of rats. The influence of naringenin (62.5, 125, 250
and 500 μM) on basal and insulin-stimulated glucose conversion to lipids (lipogenesis) as well as on basal and epinephrine-stimulated
glycerol release (lipolysis) in the isolated rat adipocytes was also tested. The basal and the stimulated lipogenesis tended to be
decreased in the presence of the flavanone (250 μM). This inhibitory effect intensified and was statistically significant at the highest
concn. of naringenin. The tested compd. did not evoke any effect on basal lipolysis while the epinephrine-stimulated process was
limited at the highest concn. of the flavanone. Naringenin (62.5, 125, 250 and 500 μM) had no effect on leptin secretion from the
isolated rat adipocytes. Results obtained in our studies demonstrate that naringenin exerts a very weak influence on carbohydrate and
lipid metab.
of normal and ethanol-consuming rats and on metab. of isolated rat adipocytes.
Answer 244:
Activity-guided isolation of antiplasmodial dihydrochalcones and flavanones from Piper hostmannianum var. berbicense.
Portet, Benedicte; Fabre, Nicolas; Roumy, Vincent; Gornitzka, Heinz; Bourdy, Genevieve; Chevalley, Severine; Sauvain, Michel;
Valentin, Alexis; Moulis, Claude. Faculte des Sciences Pharmaceutiques, UMR 152, IRD - Universite Paul Sabatier Toulouse 3,
Toulouse, Fr. Phytochemistry (Elsevier) (2007), 68(9), 1312-1320. Publisher: Elsevier Ltd., CODEN: PYTCAS ISSN: 0031-9422.
Abstract
The bioassay-guided purifn. of an n-hexane ext. from the leaves of Piper hostmannianum var. berbicense led to the isolation of four
monoterpene or prenyl-substituted dihydrochalcones (1a, 1b, 2, 3) as well as the known compds.
2',6'-dihydroxy-4'-methoxydihydrochalcone (4), linderatone (5), strobopinin (6), adunctin E (7) and (-)-methyllinderatin (8). Their
structures were established on the basis of NMR and X-ray anal. (-)-Methyllinderatin, linderatone and
2',6'-dihydroxy-4'-methoxydihydrochalcone exhibited the most potent antiplasmodial activity with IC50 values of 5.64, 10.33 and 12.69
μM, resp. against both chloroquine-sensitive and resistant strains of Plasmodium falciparum (F32, FcB1). The activity of
(-)-methyllinderatin was confirmed in vivo against Plasmodium vinckei petteri in mice (80% of redn. of parasitemia) at a dose of 20
mg/kg/day.
Answer 245:
New reports on surface flavonoids from Chamaebatiaria (Rosaceae), Dodonaea (Sapindaceae), Elsholtzia (Lamiaceae), and
Silphium (Asteraceae). Wollenweber, Eckhard; Roitman, James N. Institut fuer Botanik der TU Darmstadt, Darmstadt,
Germany. Natural Product Communications (2007), 2(4), 385-389. Publisher: Natural Product Inc., CODEN: NPCACO ISSN:
Abstract
flavanone
Lipophilic exudates of one species each of Chamaebatiaria and Elsholtzia, two species of Silphium and four Dodonaea species were
analyzed for flavonoid aglycons. In addn. to a no. of well-known and widely distributed flavonoids, several very rare and one novel
natural flavonol were isolated and identified. 1H and 13C NMR data of four flavanones and two flavones are reported.
Answer 246:
Combinatorial mutasynthesis of flavonoid analogues from acrylic acids in microorganisms. Chemler, Joseph A.; Yan,
Yajun; Leonard, Effendi; Koffas, Mattheos A. G. Department of Chemical and Biological Engineering, State University of New York
at Buffalo, Buffalo, NY, USA. Organic Letters (2007), 9(10), 1855-1858. Publisher: American Chemical Society, CODEN:
ORLEF7 ISSN: 1523-7060. Journal written in English. CAN 147:71077 AN 2007:440630 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
Flavonoids are plant secondary metabolites often used as nutraceutical supplements, but a growing no. of unnatural flavonoids are
being investigated as therapeutic agents. Cultures of Saccharomyces cerevisiae expressing recombinant flavonoid enzymes,
including 4-coumaroyl:CoA ligase (4CL), chalcone synthase (CHS), chalcone isomerase (CHI), and flavanone 3β-hydroxylase (FHT),
produced novel flavanones and dihydroflavonols when fed with a no. of arom. acrylic acids. The flavonoid network also exhibited
broad substrate specificity by converting muconic acid into a unique polypropanoid.
Answer 247:
Genes for enzymes of phenylpropanoid and flavonoid biosynthesis of Coffea and their uses in plant improvement.
Lepelley, Maud; Cheminade, Gerald; McCarthy, James Gerard; Petiard, Vincent; Lin, Chenwei; Tanksley, Steven D. (Cornell Research
Foundation, USA; Nestec S.A.). PCT Int. Appl. (2007), 159pp. CODEN: PIXXD2 WO 2007044992 A2 20070419 Designated
States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE,
EG, ES, FI, GB, GD, GE, GH, GM, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV,
LY, MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM,
SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU,
MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO
2006-US40686 20061013. Priority: US 2005-726298 20051013. CAN 146:436266 AN 2007:438164 CAPLUS (Copyright (C)

WO 2007044992 A2 20070419 WO 2006-US40686 20061013
WO 2007044992 A3 20071129
KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI,
NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT,
TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW
flavanone
EP, OA
US 2005-726298P P 20051013
Abstract
Genes for the enzymes of biosynthesis of phenylpropanoids and flavonoids in the coffee plant are cloned and characterized for use in
crop improvement. They may be used to alter plant metabolite profiles for the manipulation of flavor, aroma, and other features of
coffee beans, as well as the manipulation resistance to pathogen, herbivore, and insect attack in the coffee plant. Candidate genes
were identified by sequence comparison.
Answer 248:
Preparation of microporous crystalline molecular sieve possessing mesoporous frameworks. Ryoo, Ryong; Choi, Minkee.
(KAIST, S. Korea). PCT Int. Appl. (2007), 37pp. CODEN: PIXXD2 WO 2007043731 A1 20070419 Designated States W: AE,
AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB,
GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KZ, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW,
MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG,
US, UZ, VC, VN, YU, ZA, ZM. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT,
SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2006-KR720
20060302. Priority: KR 9716-1 20051014. CAN 146:382785 AN 2007:433844 CAPLUS (Copyright (C) 2008 ACS on SciFinder
(R))

WO 2007043731 A1 20070419 WO 2006-KR720 20060302
DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP,
KZ, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG,
PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC,
VN, YU, ZA, ZM, ZW
KR 2007041239 A 20070418 KR 2005-97161 20051014
KR 2005-97161 A 20051014
Abstract
Microporous cryst. mol. sieves having a mesoporous skeleton are prepd. by (a) adding a meso-SDA (structure directing agent) to a gel
flavanone
compn. of a mol. sieve, (b) subjecting the mixt. obtained in the above step (a) to crystn. by a hydrothermal reaction, a microwave
reaction, a dry-gel synthesis, etc., and (c) removing selectively org. materials from the resulted material obtained in the above step (b)
by a calcination or a chem. treatment. The SDA can be an organosilane, an organophosphonic acid, or a silica precursor functionalized
with the organosilane or organophosphonic acid. The obtained zeolites can be post-treated by alk. soln. treatment, ion exchange,
dealumination, metal incorporation, or org. functionalization. The prepd. mol. sieves have a good mol. diffusion ability and a greatly
improved catalytic activity.
Answer 249:
Synthesis of 7-hydroxyflavonols, 7-hydroxyflavanones and their derivatives. Wang, Qiu-an; Zhou, Qiang; Fan, Hua-fang.
College of Chemistry and Chemical Engineering, Hunan University, Changsha, Peop. Rep. China. Hecheng Huaxue (2007),
15(1), 50-54. Publisher: Hecheng Huaxue Bianjibu, CODEN: HEHUE2 ISSN: 1005-1511. Journal written in Chinese. CAN
Abstract
Five novel 7-hydroxyflavonols, 7-hydroxyflavanones and their derivs. were synthesized by aldol condensation, cyclization,
Algar-Flynn-Oyamada reaction, deprotection and O-prenylation. The overall yields were 22-36%. Target compds. thus prepd. included
resokaempferide [i.e., 3,7-dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one],
2-(3,5-dimethoxyphenyl)-3,7-dihydroxy-4H-1-benzopyran-4-one, etc. Their structures were confirmed by 1H NMR, 13C NMR, IR and
MS.
Answer 250:
New prenylated flavanones from Esenbeckia berlandieri ssp. acapulcensis. Cano, Arturo; Espinoza, Marina; Ramos, Clara H.;
Delgado, Guillermo. Facultad de Estudios Superiores Zaragoza, Universidad Nacional Autonoma de Mexico, Iztapalapa, Mex.
Journal of the Mexican Chemical Society (2006), 50(2), 71-75. Publisher: Sociedad Quimica de Mexico, CODEN: JMCSCD ISSN:
Abstract
Three new (1-3) and four known prenylated flavanones as well as friedelin were isolated from the aerial parts of Esenbeckia berlandieri
ssp acapulcensis (Rutaceae). The structures of the new compds. were elucidated as
5,7-dihydroxy-8-(2,3-epoxy-3-methyl-butyl)flavanone (1), 5,4'-dihydroxy-7-methoxy-8-(2,3-dihydroxy-3-methylbutyl)flavanone (2), and
5,7,4'-trihydroxy-8-(2,3-dihydroxy-3-methylbutyl)flavanone (3). The isolated flavanones possess diferentially functionalized isoprene
units at C-8, and this is the first report of flavanones isolated from Esenbeckia species.
Answer 251:
Na+-Glucose cotransporter (SGLT) inhibitory flavonoids from the roots of Sophora flavescens. Sato, Seizo; Takeo, Jiro;
Aoyama, Chihiro; Kawahara, Hiroyuki. Central Research Laboratory, Nippon Suisan Kaisha, Ltd, Hachioji, Tokyo, Japan.
Bioorganic & Medicinal Chemistry (2007), 15(10), 3445-3449. Publisher: Elsevier Ltd., CODEN: BMECEP ISSN: 0968-0896.
flavanone
Abstract
The methanol ext. of Sophora flavescens, which is used in traditional Chinese medicine (sophorae radix), showed potent Na+-glucose
cotransporter (SGLT) inhibitory activity. Our search for active components identified many well-known flavonoid antioxidants:
kurarinone, sophoraflavanone G, kushenol K, and kushenol N.
Answer 252:
Synthetic chalcones, flavanones, and flavones as antitumoral agents: Biological evaluation and structure-activity
relationships. Cabrera, Mauricio; Simoens, Macarena; Falchi, Gabriela; Lavaggi, M. Laura; Piro, Oscar E.; Castellano, Eduardo E.;
Vidal, Anabel; Azqueta, Amaia; Monge, Antonio; Lopez de Cerain, Adela; Sagrera, Gabriel; Seoane, Gustavo; Cerecetto, Hugo;
Gonzalez, Mercedes. Departamento de Quimica Organica, Facultad de Quimica-Facultad de Ciencias, Universidad de la Republica,
Montevideo, Urug. Bioorganic & Medicinal Chemistry (2007), 15(10), 3356-3367. Publisher: Elsevier Ltd., CODEN: BMECEP
SciFinder (R))
Abstract
A series of synthetic chalcones, flavanones, and flavones has been synthesized and evaluated for antitumor activity against the
human kidney carcinoma cells TK-10, human mammary adenocarcinoma cells MCF-7 (estrogen receptor-pos.), and human colon
adenocarcinoma cells HT-29. The most active series is the chalcone ones with the best results against TK-10 and HT-29 cells.
Fourteen out of 53 analyzed compds. resulted very active against at least two of the studied tumoral cells. Alk. single cell gel
electrophoresis, comet assay, was performed as a study of the chromosomal aberrations promoted by the compds. on normal cells.
Four active and two inactive chalcones were studied in the comet assay against normal human kidney cells (HK-2). A
structure-activity relationship anal. of these compds. was performed and for 4- and 3,4-disubstituted derivs. a quant. correlation was
obtained in the case of anti-HT-29 activity.
Answer 253:
Flavanone and 2'-OH flavanone inhibit metastasis of lung cancer cells via down-regulation of proteinases activities and
MAPK pathway. Hsiao, Yung-Chin; Kuo, Wu-Hsien; Chen, Pei-Ni; Chang, Horng-Rong; Lin, Tseng-Hsi; Yang, Wei-En; Hsieh,
Yih-Shou; Chu, Shu-Chen. Institute of Biochemistry and Biotechnology, Chung Shan Medical University, Taichung, Taiwan.
Chemico-Biological Interactions (2007), 167(3), 193-206. Publisher: Elsevier Ireland Ltd., CODEN: CBINA8 ISSN: 0009-2797.
Abstract
Flavanones richly exist in citrus and have been well characterized to have various bioactive properties. However, the anti-metastasis
properties of flavanones remain unclear. The anti-metastatic effects of six flavanones including flavanone, 2'-OH flavanone, 4'-OH
flavanone, 6-OH flavanone, naringin, and naringenin were investigated in lung cancer cells. Despite little influence on cell viability,
flavanone and 2'-OH flavanone markedly inhibited the invasion, motility, and cell-matrix adhesion of A549 cells. This was assocd. with
a reduced expression of matrix metalloproteinase (MMP)-2 and urokinase-type plasminogen activator (u-PA) in treated cells. Treatment
with flavanone and 2'-OH flavanone also potently attenuated the phosphorylations of extracellular signal-regulated kinase 1/2 (ERK
1/2) and p38MAPK, as well as the activations of NF-κB and AP-1. The reduced expressions of MMP-2 and u-PA, as well as inhibition
of cell invasion were obtained in the cultures treated with U0126 (ERK 1/2 inhibitor) and SB203580 (p38MAPK inhibitor). Thus, the
inhibitory effects of flavanone and 2'-OH flavanone on the expression of MMP-2 and u-PA may be at least partly through inactivation
flavanone
of ERK 1/2 and p38MAPK signaling pathways. Finally, oral administration of flavanone and 2'-OH flavanone were evidenced by its
inhibition on the metastasis of A549 cells and Lewis lung carcinoma (LLC) cells in vivo. In conclusion, flavanone and 2'-OH flavanone
perturb the invasion and metastasis of lung cancer cells, thereby constituting an adjuvant treatment for metastasis control.
Answer 254:
Racemization at C-2 of Naringin in Sour Oranges with Increasing Maturity Determined by Chiral High-Performance Liquid
Chromatography. Caccamese, Salvatore; Bianca, Salvatore; Santo, Davide. Dipartimento di Scienze Chimiche, Universita di
Catania, Catania, Italy. Journal of Agricultural and Food Chemistry (2007), 55(10), 3816-3822. Publisher: American Chemical
Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 147:29770 AN 2007:390851 CAPLUS
Abstract
Naringin is the major flavanone-7-O-glycoside of sour orange, and it is mainly responsible for the bitter taste of the fruit. The relative
content of (2S)- and (2R)-naringin in the albedo of sour oranges during maturation in the entire season was detd. by normal phase
HPLC using Chiralcel OD-H as chiral stationary phase and n-hexane/ethanol doped with 0.5% of TFA as mobile phase. HPLC traces
were complicated by the presence of (2S)-neohesperidin, and a software-guided anal. was developed to assess the relative amt. of the
C-2 diastereomers of naringin. A sigmoid curve was obtained showing variation from 94% of (2S)-naringin in very immature fruits to
69.7% in mature fruit samples. Spontaneous epimerization of (2S)-naringin in the ethanolic solns. of the albedo was noted after
prolonged keeping for less acid samples. The sepn. of the C-2 diastereomers of other flavanoid-7-O-glycosides present in Citrus
(neoeriocitrin, neohesperidin, and eriocitrin) was also obtained by chiral HPLC and afforded the identification, including stereochem., of
the eluting peaks in the HPLC traces of the albedo exts.
Answer 255:
Iron for collagen regeneration and other topics. Fox, Charles. USA. Cosmetics & Toiletries (2007), 122(3), 44,46-48,50.
Publisher: Allured Publishing Corp., CODEN: CTOIDG ISSN: 0361-4387. Journal; General Review written in English. CAN
Abstract
A review discusses the mechanisms and efficacy of iron for collagen regeneration. It also discusses the effect of t-flavanone on hair
growth and the use of sunscreens to enhance UV-induced ROS in the skin. Improvement of periodontal tissue damage and
antiperspirants and deodorants are tackled.
Answer 256:
Differential effect of dietary antioxidant classes (carotenoids, polyphenols, vitamins C and E) on lutein absorption.
Reboul, Emmanuelle; Thap, Sinay; Tourniaire, Franck; Andre, Marc; Juhel, Christine; Morange, Sophie; Amiot, Marie-Josephe; Lairon,
Denis; Borel, Patrick. INSERM, U476, Marseille, Fr. British Journal of Nutrition (2007), 97(3), 440-446. Publisher: Cambridge
University Press, CODEN: BJNUAV ISSN: 0007-1145. Journal written in English. CAN 146:461179 AN 2007:380179 CAPLUS
flavanone
Abstract
Lutein is assumed to protect the human retina from blue light and oxidative stress and diminish the incidence of age-related macular
degeneration. This antioxidant is commonly ingested with other dietary antioxidants. The aim of the present study was to assess
whether the main dietary antioxidants, i.e. carotenoids, polyphenols and vitamins C and E, affect lutein absorption. We measured the
effect of adding a mixt. of antioxidants (500 mg vitamin C, 67 mg (100 IU) vitamin E and 1 g polyphenols) to a lutein-contg. meal (18
mg) on the postprandial lutein response in the chylomicron-rich fraction in eight healthy men. Lutein response was weakest (-23 %; P =
0⋅07) after ingestion of the meal contg. antioxidants (21⋅9 (SEM 4⋅6) v. 28⋅4 (SEM 7⋅2) nmol × h/l). To assess the effect of each class
of antioxidants and potential interactions, the authors subsequently evaluated the effect of various combinations of antioxidants on
lutein uptake by human intestinal Caco-2 TC-7 cells. A full factorial design showed that both a mixt. of polyphenols (gallic acid,
caffeic acid, (+)-catechin and naringenin) and a mixt. of carotenoids (lycopene plus β-carotene) significantly (P<0⋅05) impaired lutein
uptake by (-10 to -30 %), while vitamins C and E had no significant effect. Subsequent expts. showed that the aglycon flavanone
naringenin was the only polyphenol responsible for the effect of the polyphenol mixt., and that the carotenoid effect was not
carotenoid species-dependent. Taken together, the present results suggest that lutein absorption is not markedly affected by physiol.
concns. of vitamins C and E but can be impaired by carotenoids and naringenin.
Answer 257:
Pharmacokinetics of the citrus flavanone aglycones hesperetin and naringenin after single oral administration in human
subjects. Kanaze, F. I.; Bounartzi, M. I.; Georgarakis, M.; Niopas, I. Department of Pharmacy, Aristotle University of
Thessaloniki, Thessaloniki, Greece. European Journal of Clinical Nutrition (2007), 61(4), 472-477. Publisher: Nature Publishing
Group, CODEN: EJCNEQ ISSN: 0954-3007. Journal written in English. CAN 147:314137 AN 2007:373993 CAPLUS
Abstract
Background and objective: Hesperetin and naringenin, the aglycons of the flavanone glycosides hesperidin and naringin, occur
naturally in citrus fruits. They exert interesting pharmacol. properties such as antioxidant, anti-inflammatory, blood lipid and cholesterol
lowering and are considered to contribute to health benefits in humans. However, no information is available on the pharmacokinetics
of the citrus flavanones hesperetin and naringenin after their oral administration to humans as pure aglycons. Therefore, the objective
of the present investigation was the evaluation of the pharmacokinetic parameters of hesperetin and naringenin in plasma and urine,
after their single oral administration in humans in the form of solid dispersion capsules, and also to improve the absorption rate of
flavanones by using aglycons rather than the naturally occurring glycosides. Design: Six healthy volunteers received orally 135 mg
of each compd., hesperetin and naringenin, under fasting conditions. Blood samples were collected at 14 different time points over a
12 h period. Urine was collected over 24 h, in five sequential timed intervals. Plasma and urine hesperetin and naringenin concns.,
after enzymic hydrolysis of their conjugated forms, were measured using validated high-pressure liq. chromatog. methods.
Pharmacokinetic parameters for hesperetin and naringenin, such as Cmax, Tmax, AUC0-t, AUC0-∞, CL/F, V/F, t1/2, MRT, Ae,
Ae(0-24), and Rmax were calcd. from their plasma or urine concns. Results: Pharmacokinetic anal. showed that both hesperetin and
naringenin were rapidly absorbed and their concns. in plasma obsd. 20 min after dosing and reached a peak in 4.0 and 3.5 h, resp. The
mean peak plasma concn. (Cmax) for hesperetin and naringenin were 825.78±410.63 ng/mL (2731.8±1358.4 nmol/l) and
2009.51±770.82 ng/mL (7386.6±2833.4 nmol/l), resp. and the mean AUC0-∞ values were 4846.20±1675.99 ng h/mL and
9424.52±2960.52 ng h/mL for hesperetin and naringenin, resp.
The elimination half-life for hesperetin was 3.05±0.91 h and for naringenin 2.31±0.40 h, resp. The mean values of the relative
cumulative urinary excretion, as percentage of the administered dose, for hesperetin and naringenin, were 3.26±0.44 and 5.81±0.81%,
resp. Conclusions: Oral administration of the flavanone aglycons, hesperetin and naringenin, lead to their rapid absorption as their
conjugated forms. The cumulative urinary recovery data indicated low bioavailability for both flavanone aglycons, owing to extensive
first-pass metab. partly by cleavage of the C-ring by the enzymes of intestinal bacteria leading to degrdn. products such as phenolic
acids.
Answer 258:
flavanone
In vitro antimicrobial activity of the leaf extract of Harungana madagascariensis Lam. ex poir. (Hypericaceae) against strains
causing otitis externa in dogs and cats. Moulari, B.; Pellequer, Y.; Chaumont, J.-P.; Guillaume, Y. C.; Millet, J. Equipe
Sciences Separatives et Biopharmaceutiques EA-3924, UFR de Medecine et de Pharmacie, Universite de Franche-comte, Besancon,
Fr. Acta Veterinaria Hungarica (2007), 55(1), 97-105. Publisher: Akademiai Kiado, CODEN: AVHUEA ISSN: 0236-6290. Journal
Abstract
Otitis externa in dogs and cats is always caused by a combination of yeasts and bacteria, among which the most important are
Malassezia pachydermatis, Staphylococcus intermedius and Pseudomonas species. These organisms often develop resistance to
classical antimicrobial agents. Therefore, the aim of this study was to investigate the antimicrobial activities of an Et acetate leaf ext.
of Harungana madagascariensis against the organisms cited, to carry out the phytochem. investigation of this ext. and to det. its
bioactive chem. class using diln. techniques, the bioautog. method and the std. phytochem. method described by Harborne (1973).
Phytochem. anal. revealed the presence of saponins, tannins, flavonoids, alkaloids and anthracenic derivs. The bioassay showed that
the antimicrobial properties may be attributed to astilbin, a flavanone deriv. identified on the basis of its spectroscopic data. The
results suggest that the ext. could be used in an antimicrobial prepn. effective against the whole range of organisms incriminated in
otitis externa in dogs and cats, with a minimal inhibitory concn. (MIC) of 250 μg/mL.
Answer 259:
Studies on chemical constituents of Glycyrrhiza uralensis Fisch. Wu, Hankui; Zhao, Yun; Mou, Xinli; Ba, Hang; Hajiakber,
Aisa. Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Wurumuqi, Peop. Rep. China.
Tianran Chanwu Yanjiu Yu Kaifa (2006), 18(3), 415-417. Publisher: Tianran Chanwu Yanjiu Yu Kaifa Bianjibu, CODEN: TCYKE5
SciFinder (R))
Abstract
From Radix Glycyrrhizae, five compds. were isolated and identified as: quercetin(1), liquorice(2), ferulaic acid(3), 5, 7, 3',
4'-tetrahydroxy- 7-glu-flavanone(4), 8, 5'-dihydroxy-3'-α-rha-flavone(5). Compds. 4 and 5 were isolated from this plant for the first
time.
Answer 260:
Methods of analysis and separation of chiral flavonoids. Yanez, Jaime A.; Andrews, Preston K.; Davies, Neal M. College of
Pharmacy, Department of Pharmaceutical Sciences and Pharmacology and Toxicology Graduate Program, Washington State
University, Pullman, WA, USA. Journal of Chromatography, B: Analytical Technologies in the Biomedical and Life Sciences
(2007), 848(2), 159-181. Publisher: Elsevier B.V., CODEN: JCBAAI ISSN: 1570-0232. Journal; General Review written in English.
Abstract
flavanone
A review. Although the anal. of the enantiomers and epimers of chiral flavanones has been carried out for over 20 years, there often
remains a deficit within the pharmaceutical, agricultural, and medical sciences to address this issue. Hence, despite increased interest
in the potential therapeutic uses, plant physiol. roles, and health-benefits of chiral flavanones, the importance of stereoselectivity in
agricultural, nutrition, pharmacokinetic, pharmacodynamic, pharmacol. activity and disposition has often been ignored. This review
presents both the general principles that allow sepn. of chiral flavanones, and discusses both the advantages and disadvantages of
the available chromatog. assay methods and procedures used to sep. quantify flavanone enantiomers and epimers in biol. matrixes.
Answer 261:
Preparation and evaluation of a new synthetic polymeric chiral stationary phase for HPLC based on the
trans-9,10-dihydro-9,10-ethanoanthracene-(11S,12S)-11,12-dicarboxylic acid bis-4-vinylphenylamide monomer. Han, Xinxin;
Wang, Chunlei; He, Lingfeng; Beesley, Thomas E.; Armstrong, Daniel W. Chemistry & Biochemistry Department, The University of
Texas at Arlington, Arlington, TX, USA. Analytical and Bioanalytical Chemistry (2007), 387(8), 2681-2697. Publisher: Springer,
CODEN: ABCNBP ISSN: 1618-2642. Journal written in English. CAN 146:533594 AN 2007:331591 CAPLUS (Copyright (C)
Abstract
A new synthetic polymeric chiral stationary phase for liq. chromatog. was prepd. via free-radical-initiated polymn. of
trans-9,10-dihydro-9,10-ethanoanthracene-(11S,12S)-11,12-dicarboxylic acid bis-4-vinylphenylamide. The new polymeric chiral
stationary phase (CSP) showed enantioselectivity for many chiral compds. in multiple mobile phases. High stability and sample
capacities were obsd. on this polymeric chiral stationary phase. Mobile phase components and additives affected chiral sepn. greatly.
This new synthetic chiral stationary phase is complementary to two other related com. available CSPs: the P-CAP and P-CAP-DP
columns. Interactions between the chiral stationary phase and analytes that lead to retention and chiral recognition include hydrogen
bonding, dipolar, and π-π interactions. Repulsive (steric) interactions also contribute to chiral recognition.
Answer 262:
Basic helix-turn-helix transcription factor Rc controlling red or white pigmentation in rice pericarp and seed coat.
McCouch, Susan; Sweeney, Megan. (Cornell Research Foundation, Inc., USA). PCT Int. Appl. (2007), 222pp. CODEN: PIXXD2
WO 2007033370 A2 20070322 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN,
CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN,
KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL,
PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US. Designated States RW: AT, BE, CH,
CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG.
Patent written in English. Application: WO 2006-US36020 20060914. Priority: US 2005-717060 20050914. CAN 146:373746 AN

WO 2007033370 A2 20070322 WO 2006-US36020 20060914
KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI,
NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT,
flavanone
TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW

US 2005-717060P P 20050914
Abstract
The present invention relates to the prodn. of red pericarp and seed coat in rice, and in particular, compns. comprising a basic
helix-turn-helix red anthocyanin transcription factor, Rc, and methods using Rc for identifying rice germplasm comprising Rc including
but not limited to grain quality grading and seed certification anal. Nucleic acid and amino acid sequences are provided for Rc alleles
in rice varieties. Single nucleotide polymorphisms are discovered that when present indicate that red pigmentation will not be produced
when when nucleotide sequences the Rc transcriptional protein are present. Also, novel PCR primers are provided for identifying rice
germplasm indicating the potential for red and non-red pigmentation i rice pericarp and seed coat. The present invention further relates
to promoter sequences of Rc binding elements including but not limited to regulatory elements of genes assocd. with
anthocyanidin/proanthocyanidin pathways and the use of these elements for controlling weedy red rice plants and controlling the
spread of transgenes into weedy red rice plants.
Answer 263:
Chemical constituents of Euryale ferox seed. Li, Mei-Hong; Yang, Xue-Qiong; Wan, Zhi-Jian; Yang, Ya-Bin; Li, Fan; Ding,
Zhong-Tao. Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, School of Chemical Science and
Technology, Yunnan University, Kunming, Peop. Rep. China. Zhongguo Tianran Yaowu (2007), 5(1), 24-26. Publisher: Zhongguo
Tianran Yaowu Bianjibu, CODEN: ZTYHA7 ISSN: 1672-3651. Journal written in Chinese. CAN 147:474475 AN 2007:327043
Abstract
The chem. constituents in the seeds of Euryale ferox Salisb were investigated for obtaining more comprehensive understanding on its
effective components. Compds. were sepd. by reversed-phase column chromatog. with silica gel and Pharmadex LH-20 gel. Their
structures were elucidated by spectral anal. and chem. evidence. Seven compds. and a mixt. of two compds. were obtained. Their
structures were identified as: cyclo(proline-serine) (compd. 1), cyclo(isoleucine-alanine) (compd. 2), cyclo(leucine-alanine) (compd. 3),
5,7,4'-trihydroxyl flavanone (compd. 4), 5,7,3',4',5'-pentahydroxyl flavanone (compd. 5), isolariciresinol-9-O-β-D-glucopyranoside
(compd. 6), α-tocopherol (compd. 7), β-locopherol (compd. 8), and δ-tocopherol (compd. 9). Compd. 1 was isolated from natural
sources for the first time. Compds. 2-6 was isolated from this plant for the first time.
Answer 264:
Spectral assignments and reference data NMR assignments of unusual flavonoids from the kino of Eucalyptus citriodora.
Freitas, Marinalva Oliveira; Lima, Mary Anne S.; Silveira, Edilberto R. Curso de Pos-Graducao em Quimica Organica, Departamento
de Quimica Organica e Inorganica, Centro de Ciencias, Universidade Federal do Ceara, Fortaleza, Brazil. Magnetic Resonance in
Chemistry (2007), 45(3), 262-264. Publisher: John Wiley & Sons Ltd., CODEN: MRCHEG ISSN: 0749-1581. Journal written in
flavanone
Abstract
Two unusual flavonoids, 3,5,4',5''-tetrahydroxy-7-methoxy-6-[1-(p-hydroxy-phenyl)ethyl]flavanone (I, R = Me) and

3,5,7,4',5''-pentahydroxy-6-[1-(p-hydroxy-phenyl)ethyl]flavanone (I, R=H ), were isolated from the kino of Eucalyptus citriodora.
Structural elucidation of the new compds. were established on the basis of spectral data, particularly by the use of 1D NMR and
several 2D shift-correlated NMR pulse sequences (1H, 1H-COSY, HMQC, HMBC).
RO O p-C 6 H 4 OH
Me
OH
p-C 6 H 4 OH O
OH I
Answer 265:
Flavonoid accumulation in Arabidopsis repressed in lignin synthesis affects auxin transport and plant growth. Besseau,
Sebastien; Hoffmann, Laurent; Geoffroy, Pierrette; Lapierre, Catherine; Pollet, Brigitte; Legrand, Michel. Institut de Biologie
Moleculaire des Plantes, Laboratoire Propre du Centre National de la Recherche Scientifique, Unite Propre de Recherche 2357,
Conventionne a l'Universite Louis Pasteur, Strasbourg, Fr. Plant Cell (2007), 19(1), 148-162. Publisher: American Society of
Plant Biologists, CODEN: PLCEEW ISSN: 1040-4651. Journal written in English. CAN 147:27029 AN 2007:318450 CAPLUS
Abstract
In A. thaliana, silencing of hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyl transferase (HCT), a lignin biosynthetic gene,
results in a strong redn. of plant growth. In HCT-silenced plants, lignin synthesis repression leads to the redirection of the metabolic
flux into flavonoids through chalcone synthase activity. Several flavonol glycosides and acylated anthocyanin were shown to
accumulate in higher amts. in silenced plants. By contrast, sinapoylmalate levels were barely affected, suggesting that the synthesis
of that phenylpropanoid compd. might be HCT-independent. The growth phenotype of HCT-silenced plants was shown to be controlled
by light and to depend on chalcone synthase expression. Histochem. anal. of silenced stem tissues demonstrated altered tracheary
elements. The level of plant growth redn. of HCT-deficient plants was correlated with the inhibition of auxin transport. Suppression of
flavonoid accumulation by chalcone synthase repression in HCT-deficient plants restored normal auxin transport and wild-type plant
growth. By contrast, the lignin structure of the plants simultaneously repressed for HCT and chalcone synthase remained as severely
altered as in HCT-silenced plants, with a large predominance of nonmethoxylated H units. Thus, the reduced size phenotype of
HCT-silenced plants is not due to the alteration of lignin synthesis but to flavonoid accumulation.
Answer 266:
Isolation and characterization of flavanone glycoside 4',5,7-trihydroxy flavanone rhamnoglucose from Garcinia kola seeds.
Okwu, D. E.; Morah, F. N. I. Department of Chemistry, Michael Okpara University of Agriculture Umudike, Nigeria. Journal of
Applied Sciences (2007), 7(2), 306-309. Publisher: Asian Network for Scientific Information, CODEN: JASODW ISSN: 1812-5654.
flavanone
Abstract
The ethanolic ext. of Garcinia kola, Heckel (Guttiferae), which had previously been shown to have biol. activity were studied.
Preliminary phytochem. screening of the plants showed the presence of flavonoids, phenolic compds., tannins and saponins. The
ethanolic ext. of Garcinia kola seeds resulted in the isolation and characterization of flavanone glycoside 4',5,7-trihydroxyflavonone
rhamnoglucose (that is naringin-7-rharmnoglucoseside) from its spectral data. 1H NMR spin system anal. and acid hydrolysis were
performed to characterize the higher order rhamnoglucosyl moiety comprising glucose and rhamnose linked to carbon 7 of the
flavanone ring system of the isolate. It is concluded that 4',5,7-trihydroxyflavanone rhamnoglucose may be a contributor to the
antioxidants, anti-inflammatory, anti-microbial, anti-tumor and anti-hepatotoxic properties exhibited by Garcinia kola seed.
Answer 267:
Catalytic enantioselective synthesis of flavanones and chromanones. Scheidt, Karl A.; Biddle, Margaret. Department of
Chemistry, Northwestern University, Evanston, IL, USA. Abstracts of Papers, 233rd ACS National Meeting, Chicago, IL, United
States, March 25-29, 2007 (2007), ORGN-598. Publisher: American Chemical Society, Washington, D. C CODEN: 69JAUY
Conference; Meeting Abstract; Computer Optical Disk written in English. AN 2007:296624 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
The flavanone core is abundant in natural products that possess significant bioactivity, including anti-tumor, anti-inflammatory, and
aromatase inhibition. A limited no. of strategies have been developed for the asym. synthesis of flavanones, including resoln. of the
related alcs., or displacement reactions. Our strategy is to incorporate a functional group on the potential substrate (1) that (a)
enhances the reactivity of the conjugate acceptor, (b) favors the cyclized flavanones over the acyclic chalcones and (c) provides a
second Lewis basic site for interaction with a catalyst. The use of catalytic chiral thioureas catalyzed the asym. conjugate addn. of 1
to form 2 in high yield with excellent enantioselectivity. The scope and details of the process will be presented.
Answer 268:
Synthesis and antiviral activity of Abyssinone II analogs. Moriarty, Robert M.; Surve, Bhushan C.; Naithani, Rajesh;
Chandersekera, Susantha N.; Tiwari, Vaibhav; Shukla, Deepak. Department of Chemistry, University of Illinois, Chicago, IL,
USA. Abstracts of Papers, 233rd ACS National Meeting, Chicago, IL, United States, March 25-29, 2007 (2007), MEDI-063.
Publisher: American Chemical Society, Washington, D. C CODEN: 69JAUY Conference; Meeting Abstract; Computer Optical Disk
Abstract
Several novel analogs of Abyssinone II, a naturally occurring prenylated flavanone, were synthesized using isoprene as source of
isoprenyl group. This synthesis involves prenylation of p-hydroxybenzaldehyde using prenyl bromide, formation of prenylated
polyhydroxychalcone and cyclization to 1, 1I and III. Flavanones IV and V were synthesized using Stille coupling. The compds. were
tested in Hela 5 cells using a recombinant a-galactosidase expressing strain of HSV-1(Herpes simplex virus Type 1). The ONPG
(ortho-nitrophenol galactoside) viral entry assay was used to measure the viral entry into the treated and untreated cells. The
syntheses of analogs I-V will be presented along with antiviral data.
Answer 269:
flavanone
Genes up-regulated during red coloration in UV-B irradiated lettuce leaves. Park, Jong-Sug; Choung, Myoung-Gun; Kim,
Jung-Bong; Hahn, Bum-Soo; Kim, Jong-Bum; Bae, Shin-Chul; Roh, Kyung-Hee; Kim, Yong-Hwan; Cheon, Choong-Ill; Sung, Mi-Kyung;
Cho, Kang-Jin. Research Planning & Information Division, National Institute of Agricultural Biotechnology, Suwon, S. Korea.
Plant Cell Reports (2007), 26(4), 507-516. Publisher: Springer, CODEN: PCRPD8 ISSN: 0721-7714. Journal written in English.
Abstract
Mol. anal. of gene expression differences between green and red lettuce leaves was performed using the SSH method. BlastX
comparisons of subtractive expressed sequence tags (ESTs) indicated that 7.6% of clones encoded enzymes involved in secondary
metab. Such clones had a particularly high abundance of flavonoid-metab. proteins (6.5%). Following SSH, 566 clones were
rescreened for differential gene expression using dot-blot hybridization. Of these, 53 were found to overexpressed during red
coloration. The up-regulated expression of six genes was confirmed by Northern blot analyses. The expression of chalcone synthase
(CHS), flavanone 3-hydroxylase (F3H), and dihydroflavonol 4-reductase (DFR) genes showed a pos. correlation with anthocyanin
accumulation in UV-B-irradiated lettuce leaves; flavonoid 3',5'-hydroxylase (F3',5'H) and anthocyanidin synthase (ANS) were
expressed continuously in both samples. These results indicated that the genes CHS, F3H, and DFR coincided with increases in
anthocyanin accumulation during the red coloration of lettuce leaves. This study show a relationship between red coloration and the
expression of up-regulated genes in lettuce. The subtractive cDNA library and EST database described in this study represent a
valuable resource for further research for secondary metab. in the vegetable crops.
Answer 270:
Synthesis of 7,3',5'-trisubstituted flavanones and flavonols. Wang, Qiu-an; Fang, Wei-qin; Liao, Tou-gen. College of
Chemistry and Chemical Engineering, Hunan Univ., Changsha, Hunan, Peop. Rep. China. Hunan Daxue Xuebao, Ziran Kexueban
(2006), 33(6), 98-102. Publisher: Hunan Daxue Qikanshe, CODEN: HDAXE3 Journal written in Chinese. CAN 147:448550 AN
Abstract
7,3',5'-Trisubstituted flavanones and flavonols were synthesized by esterification, acetylation, methoxymethyl protection or
methylation, hydrazidation, oxidn., aldol condensation, cyclization, Algar-Flynn-Oyamada reaction and deprotection, using
3,5-dihydroxybenzoic acid and resorcinol as the starting materials in overall yield of 21 % .apprx. 32 %. Their structures were
confirmed by 1HNMR, IR and mass spectra. The compd. I, a new natural flavanone isolated from the medicinal plant Caragana
intermedia Kang et H. C. Fu, was firstly synthesized.
OH
HO O
OH
O I
flavanone
Answer 271:
The total flavanone of onion extraction and the identification by ultrasonic wave. Huang, Suo-yi; Luo, Jian-hua; Feng, Ling.
Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Guangxi, Peop. Rep. China. Weiliang Yuansu Yu
Jiankang Yanjiu (2007), 24(1), 31-33. Publisher: Weiliang Yuansu Yu Jiankang Yanjiu Zazhishe, CODEN: WYYJAF ISSN:
Abstract
The objective is to in order to make use of the resources of onion, avoid wasting and approach the extn. of total flavanone of onion.
The flavonoids were extd. by ethanol as the solvent from onion with ultrasonic wave and ethanol extn. Spectrophotometry used in the
ext. and check the flavanone of onion. By this method getting the c d. of the total flavanone of onion is C=20.58% and the rate of
av. recovery is 102.1%. This text provides the extn. and purifying methods to get the outcome and the purity of the flavanone are all
very high. This method is a purely phys. process and has not any pollution. It is an ideal way to ext. the flavanone of onion.
Answer 272:
Performance of a new HPLC chiral stationary phase derived from N-(3,5-dinitrobenzoyl)-D-α-phenylglycine with a
quinoxaline branching unit. Forjan, D. Moslavac; Vinkovic, V.; Kontrec, D. Laboratory for Stereoselective Catalysis and
Biocatalysis, Rudjer Boskovic Institute, Zagreb, Croatia. Acta Chromatographica (2006), 17 97-107. Publisher: Silesian
University, Institute of Chemistry, CODEN: ATCREU ISSN: 1233-2356. Journal written in English. CAN 147:397402 AN
Abstract
A new brush-type HPLC chiral stationary phase (CSP) comprising π-acidic N-(3,5-dinitrobenzoyl)-D-α-phenylglycine chiral units bound
to the quinoxaline units of modified γ-aminopropyl silica gel by a 1,2-diaminoethane spacer was prepd. by solid-phase synthesis. To
test the CSP attempts were made to sep. the enantiomers of twenty-two racemates with different functional groups and the results
were compared with those obtained using three structurally related chiral stationary phases.
Answer 273:
Synthesis of 5,7-dihydroxyflavanone. Cheng, Yong-hao; Duan, Ya-bo; Qi, Yan; Guo, Xiao-yun; Tong, Yuan-feng; Du, Guan-hua;
Wu, Song. Inst. Materia Med., Chinese Acad. Med. Sci. and Peking Union Med. Coll., Beijing, Peop. Rep. China. Huaxue Shiji
(2006), 28(7), 437-438. Publisher: Huaxue Shiji Bianjibu, CODEN: HUSHDR ISSN: 0258-3283. Journal written in Chinese. CAN
Abstract
Synthesis of 5,7-dihydroxyflavanone [i.e, 2,3-dihydro-5,7-dihydroxy-2-phenyl-4H-1-benzopyran-4-one] using palladium/carbon as

catalyst. The effects of reaction time, reaction temp. and amt. of catalyst on the reaction were discussed. The optimized reaction
conditions were: reaction temp. 53°, reaction time 2h and catalyst 1.0 g. The yield of the reaction was 83.26%.
flavanone
Answer 274:
Flavonoids and risk of squamous cell esophageal cancer. Rossi, Marta; Garavello, Werner; Talamini, Renato; La Vecchia,
Carlo; Franceschi, Silvia; Lagiou, Pagona; Zambon, Paola; Dal Maso, Luigino; Bosetti, Cristina; Negri, Eva. Istituto di Ricerche
Farmacologiche "Mario Negri", Milan, Italy. International Journal of Cancer (2007), 120(7), 1560-1564. Publisher: Wiley-Liss, Inc.,
CODEN: IJCNAW ISSN: 0020-7136. Journal written in English. CAN 146:273425 AN 2007:269135 CAPLUS (Copyright (C)
Abstract
The relation between 5 classes of flavonoids (flavanones, flavan-3-ols, flavonols, flavones and anthocyanidines) and esophageal
cancer was investigated using data from a case-control study conducted between 1992 and 1997 in 3 areas of northern Italy. The
study included 304 cases (275 men, 29 women) with a first diagnosis of squamous-cell carcinoma of the esophagus and 743 controls
(593 men, 150 women) with no history of cancer, admitted for acute illnesses, unrealted to tobacco and alc. consumption, to major
hospitals of the areas under surveillance. Dietary habits were investigated using a validated food frequency questionnaire. Odds
ratios (ORs) and 95% confidence intervals (CI) were computed after allowance for age, sex, study center, years of education, alc.
drinking, tobacco smoking, body mass index and energy intake. An inverse assocn. emerged between flavanone intake and
esophageal cancer risk (OR = 0.38 for the highest vs. the lowest quintile, 95% CI = 0.23-0.66). The inverse relation between
flavanones and esophageal cancer tended to be stronger in those who drank ≥6 drinks/day. In conclusion, this study suggests that
flavanone intake is inversely assocd. with esophageal cancer risk and may account, with vitamin C, for the protective effect of fruit,
esp. citrus fruit, on esophageal cancer.
Answer 275:
Application of flavanone compound in medicine for treating cardiovascular disease. Zhao, Jinhua; Kang, Hui; Yao,
Guanghui; Zeng, Weizhen; Liu, Xiaorou; Li, Jing; Feng, Hanlin; Yu, Lin. (Shenzhen Neptunus Pharmaceutical Co., Ltd., Peop. Rep.
China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 13pp. CODEN: CNXXEV CN 1923191 A 20070307 Patent
written in Chinese. Application: CN 1009-3643 20050831. Priority: . CAN 146:365638 AN 2007:265819 CAPLUS (Copyright

CN 1923191 A 20070307 CN 2005-10093643 20050831
CN 2005-10093643 20050831
Abstract
The title flavanone compd. (I, R1 = H or CH3; R2 = H or CH3; R3 = H or OH) can be used for treating cardiovascular disease, such as
myocardial infarction, angina pectoris, hypertension, arteriosclerosis, hyperlipemia, and coronary artery disease. The flavanone
compds. are extd. from Blumea balsamifera. The content of flavanone in unit formulation is 5-1000 mg.
flavanone
OH
OR 2
R1O O
R3
OH O I
Answer 276:
Catalytic Enantioselective Synthesis of Flavanones and Chromanones. Biddle, Margaret M.; Lin, Michael; Scheidt, Karl A.
Department of Chemistry, Northwestern University, Evanston, IL, USA. Journal of the American Chemical Society (2007),
129(13), 3830-3831. Publisher: American Chemical Society, CODEN: JACSAT ISSN: 0002-7863. Journal written in English. CAN
Abstract
Nonracemic dihydrobenzopyranones I (R = Ph, 2-ClC6H4, 4-MeC6H4, 4-MeOC6H4, 4-BrC6H4, cyclohexyl, PhCH2CH2; R1 = H, Me,
MeO; R2 = H; R1R2 = CH:CHCH:CH) are prepd. in 65-92% yields and in 78-94% ee by cyclization of the
(E)-(hydroxyaroyl)propenoates II (R = Ph, 2-ClC6H4, 4-MeC6H4, 4-MeOC6H4, 4-BrC6H4, cyclohexyl, PhCH2CH2; R1 = H, Me, MeO;
R2 = H; R1R2 = CH:CHCH:CH) in the presence of nonracemic thiourea III followed by acid-mediated decarboxylation in the presence
of either p-toluenesulfonic acid or magnesium bromide-diethyl ether complex. I (R = PhCH2CH2; R1 = R2 = H) is prepd. in 77% yield
and 80% ee in one pot from 2-HOC6H4COCH2CO2CMe3 and hydrocinnamaldehyde using a nonracemic thiourea catalyst; the one-pot
procedure avoids difficultly-sepd. byproducts of nonselective cyclization formed in the Knoevenagel condensation reactions of alkyl
aldehydes with hydroxyaroylacetates. The structure of II (R = 4-BrC6H4; R1 = R2 = H) is detd. by X-ray crystallog.
flavanone
O O R
R2 R2
C O 2 CMe 3
R1 O R I R1 OH II
CF 3
HN N CF 3
H
PhCH 2O
H
N
H2 C N
III
Answer 277:
Warm and cold parental reproductive environments affect seed properties, fitness, and cold responsiveness in Arabidopsis
thaliana progenies. Bloedner, C.; Goebel, C.; Feussner, I.; Gatz, C.; Polle, A. Institut fuer Forstbotanik, Georg-August
Universitaet Goettingen, Germany. Plant, Cell and Environment (2007), 30(2), 165-175. Publisher: Blackwell Publishing Ltd.,
CODEN: PLCEDV ISSN: 0140-7791. Journal written in English. CAN 147:360853 AN 2007:260702 CAPLUS (Copyright (C)
Abstract
Conditions in the parental environment during reprodn. can affect the performance of the progenies. The goals of this study were to
investigate whether warm or cold temps. in the parental environment during flowering and seed development affect Arabidopsis thaliana
seed properties, growth performance, reprodn. and stress tolerance of the progenies, and to find candidate genes for progeny-related
differences in stress responsiveness. Parental plants were raised at 20 °C and maintained from bolting to seed maturity at warm (25
°C) or cold (15 °C) temps. Anal. of seed properties revealed significant increases in nitrogen in seeds from warm temp. and significant
increases in lipids and in the ratio of α-linolenic to oleic acid in seeds from the cold parental environment. Progenies of the warm
parental environment showed faster germination rates, faster root elongation growth, higher leaf biomass and increased seed prodn. at
various temps. compared with those from the cold parental environment. This indicates that under stable environmental conditions,
progenies from warm parental environments had a clear adaptive advantage over those from cold parental environments. This
parental effect was presumably transmitted by the higher nitrogen content of the seeds developed in warm conditions. When offspring
from parents grown at different temps. were exposed to chilling or freezing stress, photosynthetic yield recovered faster in progenies
originating from cold parental environments. Cold acclimation involved up-regulation of transcripts of flavanone 3-hydroxylase (F3H)
and pseudo response regulator 9 (PRR9) and down-regulation of growth-assocd. transcription factors (TFs) NAP and AP2 domain contg.
RAP2.3. NAP, a regulator of senescence, and PRR9, a temp.-sensitive modulator of the circadian clock, were probably involved in
flavanone
mediating parent-of-origin effects, because they showed progeny-related expression differences under chilling. Because low temps.
also delay senescence, cold responsiveness of NAP suggests that this factor is linked with the regulatory network that is
important for environmental acclimation of plants.
Answer 278:
Artificial sweetener. Abushqara, Elias. R&D Department, Frutarom, Haifa, Israel. Speciality Chemicals Magazine (2007),
27(1), 26-28. Publisher: DMG World Media (uk) Ltd., CODEN: SPCHEY ISSN: 0262-2262. Journal; General Review written in
Abstract
A review. A discussion on the need for artificial sweeteners and the parameters that should be considered with regard to intense
sweetener. These parameters include: stability in heat and pH, soly., taste profile, toxicity, and the possibility of use in combination
with bulk sweeteners, bulking agents and preserving agents.
Answer 279:
Extraction of total flavanone from mango leaves by ultrasonic wave. Huang, Suo-yi; Li, Hai-ni; Tang, Yu-lian; Zhang,
Jing-xuan. Department of Chemistry, Youjiang Ethnic Medical College, Baise, Peop. Rep. China. Zhongguo Xiandai Yingyong
Yaoxue (2006), 23(6), 455-456. Publisher: Zhongguo Xiandai Yingyong Yaoxue Zazhi Bianji Weiyuanhui, CODEN: ZXYYAI ISSN:
Abstract
The ext. method for total flavanone from mango leaves was studied in order to make full use of the resources of mango leaves. The
flavanone was extd. by ethanol from mango leaves with ultrasonic wave and detd. by spectrophotometry. The d. amt. of the total
flavanone of ext. from mango leaves was 2.900 mg/mL and the recovery was 100.2%. This method is a purely phys. process and
has not any pollution. It is an ideal way to ext. the flavanone from mango leaves.
Answer 280:
Tunable Transition Metal-Ligand Complexation for Enhanced Elucidation of Flavonoid Diglycosides by Electrospray
Ionization Mass Spectrometry. Pikulski, Michael; Aguilar, Apolonio; Brodbelt, Jennifer S. Department of Chemistry and
Biochemistry, The University of Texas at Austin, Austin, TX, USA. Journal of the American Society for Mass Spectrometry
(2007), 18(3), 422-431. Publisher: Elsevier Inc., CODEN: JAMSEF ISSN: 1044-0305. Journal written in English. CAN 146:353990
Abstract
A tunable ESI-MS/MS strategy for differentiation of flavone and flavanone diglycoside isomers based on metal complexation with
auxiliary ligands is reported. The addn. of a metal salt and an auxiliary ligand to a flavonoid soln. results in the formation of [M(II)
(flavonoid-H) auxiliary ligand]+ complexes, where M(II) is a transition metal. A series of auxiliary ligands with electron-withdrawing
flavanone
substituents were synthesized to tailor the relative metal binding affinities of the ligands and thus directly influence the stabilities, and
consequently the dissocn. pathways, of the complexes. Upon collisionally activated dissocn., the complexes yield fragmentation
patterns in which the abundances of key diagnostic ions are enhanced, thus facilitating isomer differentiation.
Answer 281:
Effect of the Citrus flavanone naringenin on oxidative stress in rats. Andrade, Juan E.; Burgess, John R. Department of
Foods and Nutrition, Purdue University, West Lafayette, IN, USA. Journal of Agricultural and Food Chemistry (2007), 55(6),
Abstract
Flavonoids are non-nutrient plant phenolic compds. proposed to provide health benefits in humans. The antioxidant and prooxidant
effects of the citrus flavanone naringenin have been tested only in vitro. The dose-response effect of naringenin consumption was
tested in weanling rats (n = 6-8/group) with a 2 × 4 factorial design using high or low oxidative stress (Hox or Lox, resp.) diets, created
by adequate or deficient amts. of vitamin E and selenium, with three increasing naringenin concns. (30, 60, or 120 mg/kg of diet). Hox
compared to Lox rats exhibited reduced growth and liver hypertrophy, which was not prevented by naringenin consumption. Also, Hox
rats exhibited severalfold higher liver NAD(P)H:quinone oxidoreductase-1 activity, which was further elevated in proportion to
naringenin intake, but this was not sufficient to protect against oxidative stress indicated by higher liver total aldehydes. In addn.,
dietary naringenin did not affect antioxidant nutrient status or physiol. markers of growth under Lox conditions. Thus, dietary
naringenin did not exhibit antioxidant or prooxidant effects in vivo in this rat model.
Answer 282:
Effect of storage on the content of polyphenols, vitamin C and the antioxidant activity of orange juices. Klimczak, Inga;
Malecka, Maria; Szlachta, Miroslawa; Gliszczynska-Swiglo, Anna. Faculty of Commodity Science, Poznan University of Economics,
Poznan, Pol. Journal of Food Composition and Analysis (2007), 20(3-4), 313-322. Publisher: Elsevier, CODEN: JFCAEE ISSN:
Abstract
The effect of time and temp. on the content of vitamin C, total polyphenols and individual phenolic compds. as well as on the
antioxidant activity of two com. orange juices was studied. The polyphenol content was detd. using Folin-Ciocalteu and HPLC
methods. The two methods, SPE vs. direct injection following a simple treatment of samples, were compared to assess two
techniques of sample prepn. For antioxidant capacity detn., DPPH and FRAP assays were used. All analyses were carried out for
fresh juices and after storage at 18, 28 and 38 °C for 2, 4 and 6 mo. It was found that vitamin C and free and conjugated
hydroxycinnamic acids were the most affected by both duration and temp. of storage. The decrease in the content of polyphenols
and vitamin C upon storage was reflected by the decrease in the antioxidant capacity of orange juices. Small changes in flavanone
content were obsd., indicating high stability of these compds. upon storage.
Answer 283:
Construction of a flavonoid database for assessing intake in a population-based sample of women on Long Island, New
flavanone
York. Fink, Brian N.; Steck, Susan E.; Wolff, Mary S.; Kabat, Geoffrey C.; Gammon, Marilie D. Department of Epidemiology,
School of Public Health, University of North Carolina, Chapel Hill, NC, USA. Nutrition and Cancer (2006), 56(1), 57-66.
Publisher: Lawrence Erlbaum Associates, Inc., CODEN: NUCADQ ISSN: 0163-5581. Journal written in English. CAN 146:337124
Abstract
Flavonoids have been hypothesized to reduce cancer risk. Previous epidemiol. studies conducted to evaluate this hypothesis have
not assessed all flavonoids, including classes that could contribute to intake among Americans, which would result in an
underestimation of intake. This misclassification could mask variability among individuals, resulting in attenuated effect ests. for the
assocn. between flavonoids and cancer. To augment flavonoid and lignan intake ests., we developed a database that can be used in
conjunction with a food-frequency questionnaire (FFQ). Coupling information derived from the available literature with the U.S.
Department of Agriculture databases, we estd. content of 6 flavonoid classes and lignans for 50 food group items. We combined
these ests. with responses from a modified Block FFQ that was self-completed in 1996-1997 by a population-based sample of women
without breast cancer on Long Island, New York (n = 1,500). Total flavonoid and lignan content of food items ranged from 0 to 129
mg/100 g, and the richest sources were tea, cherries, and grapefruit. Individual intake ests., from highest to lowest, were flavan-3-ols,
flavanones, flavonols, lignans, isoflavones, anthocyanidins, and flavones. Each class of flavonoids and lignans exhibited a wide
range of intake levels. This database is useful to quantify flavonoid and lignan intake for other observational studies conducted in the
United States that utilize the Block FFQ.
Answer 284:
Cytochrome P 450s in flavonoid metabolism. Ayabe, Shin-ichi; Akashi, Tomoyoshi. Department of Applied Biological Sciences,
Nihon University, 1866 Kameino, Fujisawa, Kanagawa, Japan. Phytochemistry Reviews (2006), 5(2-3), 271-282. Publisher:
Springer, CODEN: PRHEBS ISSN: 1568-7767. Journal; General Review written in English. CAN 146:223183 AN 2007:187112
Abstract
A review. Cytochrome P 450s (CYPs) that catalyze arom. hydroxylations, aliph. hydroxylations, and skeleton formation in flavonoid
metab. are surveyed. They are involved in the biosynthesis of anthocyanin pigments and condensed tannins CYP75 (flavonoid
3',5'-hydroxylase and 3'-hydroxylase); flavones [CYP93B, (2S)-flavanone 2-hydroxylase and flavone synthase II]; and leguminous
isoflavonoid phytoalexins [CYP71D9, flavonoid 6-hydroxylase; CYP81E, isoflavone 2'-hydroxylase and 3'-hydroxylase; CYP93A,
3,9-dihydroxypterocarpan 6a-hydroxylase; and CYP93C, 2-hydroxyisoflavanone synthase (IFS)]. Other P 450s of flavonoid metab.
include the methylenedioxy bridge-forming enzyme, cyclases producing glyceollins, flavonol 6-hydroxylase, and
8-dimethylallylnaringenin 2'-hydroxylase. Mechanistic studies on the unusual aryl migration by CYP93C, regulation of IFS expression
in plant organs and its biotechnol. applications, and flavonoid metab. by non-plant P 450s are also briefly discussed.
Answer 285:
Prohexadione-Ca: modes of action of a multifunctional plant bioregulator for fruit trees. Rademacher, W.; Spinelli, F.;
Costa, G. BASF Agricultural Center, Global Research Agricultural Products, Limburgerhof, Germany. Acta Horticulturae (2006),
727(Proceedings of the Xth International Symposium on Plant Bioregulators in Fruit Production, 2005), 97-106. Publisher: International
Society for Horticultural Science, CODEN: AHORA2 ISSN: 0567-7572. Journal; General Review written in English. CAN
flavanone
Abstract
A review. Prohexadione-Ca is a plant bioregulator that is primarily used to inhibit excessive vegetative growth in fruit trees and other
crop plants. Addnl., effects on the incidence of bacterial and fungal diseases and on insect pests are often obsd. Furthermore, the
compd. may reduce abortion of fruitlets, thereby increasing fruit set. Prohexadione-Ca is relatively short-lived and possesses very
favorable toxicol. and ecotoxicol. features. The compd. acts as a structural mimic of 2-oxoglutaric acid. Therefore, distinct
dioxygenases involved in gibberellin biosynthesis, which require this compd. as a co-substrate, are blocked (e.g. GA20
3β-hydroxylase). As a result, less growth-active gibberellins are formed and treated plants remain compact. 2-Oxoglutaric
acid-dependent dioxygenases are also involved in flavonoid metab. In shoots of apples and pears, prohexadione-Ca causes
considerable changes in the formation of flavonoids and their phenolic precursors by inhibiting flavanone 3-hydroxylase.
Prohexadione-Ca triggers pathogen resistance by inducing the formation of 3-deoxyflavonoids, in particular luteoforol, with
phytoalexin-like properties. A similar mechanism may explain the lowered incidence of insect pests. Finally, treatments with
prohexadione-Ca lead to reduced ethylene formation. This is due to structural similarities with ascorbic acid, the co-substrate of
aminocyclopropanecarboxylic acid oxidase, another dioxygenase, which is involved in ethylene biosynthesis. Lowered ethylene
levels, together with elevated availability of assimilates that are no longer needed for shoot growth, explains increases in fruit set.
Answer 286:
Optimization of the synthesis of 2,6-dinitro-4-trifluoromethylphenyl ether substituted cyclodextrin bonded chiral stationary
phases. Zhong, Q.; He, L.; Beesley, T. E.; Trahanovsky, W. S.; Sun, P.; Wang, C.; Armstrong, D. W. Department of Chemistry,
Iowa State University, Ames, IA, USA. Chromatographia (2006), 64(3-4), 147-155. Publisher: Vieweg Verlag/GWV Fachverlage
GmbH, CODEN: CHRGB7 ISSN: 0009-5893. Journal written in English. CAN 147:335089 AN 2007:176205 CAPLUS
Abstract
The comparisons of five different chiral stationary phases (CSPs) based on 2,6-dinitro-4-trifluoromethylphenyl (DNP-TFM) ether
substituted β-cyclodextrin are presented. The five CSPs differ from each other in the linkage/spacer chem., or on the position of the
substituents on β-cyclodextrin, or in the sequence of the synthetic procedure. There are two optimum combinations: (1) DNP-TFM
randomly substituted on the β-cyclodextrin as the chiral selector along with a carbamate linkage chain bonding it to the silica support;
and (2) β-cyclodextrin derivatized by DNP-TFM substituents only on the C-2 and C-3 positions of the cyclodextrin with an ether linkage
chain anchoring it to the silica gel. These two combinations show complementary sepns. for some enantiomers. The spacer chain
effect is much more pronounced for the CSP based on the β-cyclodextrin derivs. with DNP-TFM substituents only on C-2 and C-3
positions than its randomly substituted counterpart. The sequence of derivatizing the cyclodextrin and attaching it to silica gel also
affects its selectivity and efficiency. The β-cyclodextrin should be derivatized before it is linked to the silica gel.
Answer 287:
Antibacterial Pterocarpans from Erythrina subumbrans. Rukachaisirikul, Thitima; Innok, Phongsak; Aroonrerk, Nuntana;
Boonamnuaylap, Woraluk; Limrangsun, Saranya; Boonyon, Chanakan; Woonjina, Umpawan; Suksamrarn, Apichart. Department of
Chemistry, Faculty of Science, Ramkhamhaeng University, Bangkok, Thailand. Journal of Ethnopharmacology (2007), 110(1),
171-175. Publisher: Elsevier B.V., CODEN: JOETD7 ISSN: 0378-8741. Journal written in English. CAN 147:537750 AN
Abstract
flavanone
Seven pterocarpans, erybraedin B (1), erybraedin A (2), phaseolin (3), erythrabyssin II (4), erystagallin A (5), erythrabissin-1 (6) and
erycristagallin (7), two flavanones, 5-hydroxysophoranone (8) and glabrol (9), and one isoflavone, erysubin F (10), were isolated from
the stems of Erythrina subumbrans (Leguminosae). Their structures were identified by means of spectroscopy. This is the first report
of the isolation of the non-alkaloidal compds. from Erythrina subumbrans and the obsd. dehydration of 6a-hydroxypterocarpans 5 and
6 in CDCl3 to the corresponding pterocarpenes 11 and 12, resp. Compds. 8 and 9 were isolated for the first time from the genus
Erythrina. Compds. 2 and 4 exhibited the highest degree of activity against Streptococcus strains with an MIC range of 0.78-1.56
μg/mL, whereas compd. 7 exhibited the highest degree of activity against Staphylococcus strains, including drug-resistant strains
(MRSA and VRSA), with an MIC range of 0.39-1.56 μg/mL. Interestingly, compds. 2, 4, 5 and 7 were more active against several
strains of Streptococcus and Staphylococcus than the std. antibiotics vancomycin and oxacillin. Compd. 7 showed the highest level
of activity against all VRSA strains tested, with an MIC range of 0.39-1.56 μg/mL, which were resistant to both antibiotics. These
compds. may prove to be potent phytochem. agents for antibacterial activity, esp. against the MRSA and VRSA strains.
Answer 288:
Enantioseparation of some chiral flavanones using microbial cyclic β-(1→3),(1→6)-glucans as novel chiral additives in
capillary electrophoresis. Kwon, Chanho; Park, Heylin; Jung, Seunho. Department of Bioscience and Biotechnology, Konkuk
University, Seoul, S. Korea. Carbohydrate Research (2007), 342(5), 762-766. Publisher: Elsevier B.V., CODEN: CRBRAT
SciFinder (R))
Abstract
Cyclic β-(1→3),(1→6)-glucans, microbial cyclooligosaccharides produced by Bradyrhizobium japonicum USDA 110, were used as novel
chiral additives for the enantiomeric sepn. of some flavanones such as eriodictyol, homoeriodictyol, hesperetin, naringenin, and
isosakuranetin in capillary electrophoresis (CE). Among the flavanones, eriodictyol was sepd. with the highest resoln. (Rs 5.66) and
selectivity factor (α 1.18) when 20 mM cyclic β-(1→3),(1→6)-glucans were added to the background electrolyte (BGE) at pH 8.3.
Answer 289:
Andrology in the skin: pathogenesis and therapy of androgenetic alopecia. Inui, Shigeki. Dep. Regenerative Dermatol.,
Course Mol. Med., Grad. Sch. Med., Osaka University, Suita, Japan. Nippon Hifuka Gakkai Zasshi (2006), 116(13), 2142-2146.
Publisher: Nippon Hifuka Gakkai, CODEN: NHKZAD ISSN: 0021-499X. Journal; General Review written in Japanese. CAN
Abstract
A review. I described here two important aspects of pathogenesis of androgenetic alopecia (AGA): (1) Regulators of androgen
sensitivity in hair follicles and (2) Sol. mediators involved in AGA pathomechanism. Moreover, we discussed about the therapeutic
agents for AGA and their putative action in the pathomechanism.
Answer 290:
Prenylflavonoid formulations. Kuhrts, Eric. (Bioactives, Inc., USA). PCT Int. Appl. (2007), 35pp. CODEN: PIXXD2 WO
2007016578 A2 20070208 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO,
flavanone
CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP,
KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO,
RS, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC. Designated States RW: AT, BE, CH, CY,
DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent
written in English. Application: WO 2006-US29962 20060731. Priority: US 2005-703677 20050729. CAN 146:235839 AN

WO 2007016578 A2 20070208 WO 2006-US29962 20060731
WO 2007016578 A3 20070816
KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO,
NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA,
UG, US, UZ, VC, VN, ZA, ZM, ZW
EP, OA
AU 2006275491 A1 20070208 AU 2006-275491 20060731
CA 2617209 A1 20070208 CA 2006-2617209 20060731
EP 1909584 A2 20080416 EP 2006-789123 20060731
PT, RO, SE, SI, SK, TR
US 2005-703677P P 20050729
WO 2006-US29962 W 20060731
Abstract
Methods and formulations for increasing the water soly. and/or bioavailability of prenylfiavonoids are disclosed. The formulations may
be employed to treat a disease states, including cancer.
Answer 291:
Characteristics of flavonoids in Niihime fruit - a new sour citrus fruit. Miyake, Yoshiaki. Faculty of Human Wellness,
Tokaigakuen University, Nagoya, Japan. Food Science and Technology Research (2006), 12(3), 186-193. Publisher: Japanese
Society for Food Science and Technology, CODEN: FSTRFS ISSN: 1344-6606. Journal written in English. CAN 147:187778 AN
Abstract
flavanone
Niihime fruit, produced in the coastal area of the Sea of Kumano in Mie prefecture, is a new sour citrus fruit. This is the first study to
examine the characteristics of the flavonoids in niihime fruit. The content of flavonoids in the juice and peel of niihime fruit was detd.
by HPLC and their distribution was examd. in comparison with seven other species of sour citrus fruits. Niihime fruit was found to
contain a comparatively high quantity of bioactive flavonoids of the flavanone glycosides with rutinose sugar chain such as eriocitrin
and hesperidin as well as the polymethoxyflavones such as nobiletin and tangeretin. The peel ext. of niihime fruit exhibited
comparatively high antioxidative activity among sour citrus fruits using the DPPH radical scavenging assay. Furthermore, the
flavonoids eluted from niihime fruit by over time in hot and cold solns. of water, 5% ethanol, and 25% ethanol, which are commonly
used in the field of food processing and cooking, were examd. The flavonoids eluted from niihime fruit in hot 25% ethanol soln. was
highest content in solns., and the content of flavonoids eluted in 5 min was an approx. half of content eluted in 60 min. The flavanone
glycosides, eriocitrin and hesperidin, were eluted in higher contents in hot solns. than in cold solns. The polymethoxyflavones,
nobiletin and tangeretin, were eluted to some extent in hot 5% ethanol but were found in low contents in cold solns. The highest
contents were eluted in hot 25% ethanol. The difference in the elution properties between flavanone glycosides and
polymethoxyflavones is considered to be a result of their hydrophobic properties. The scavenging activity of DPPH radical for
eluates was shown to increase over time, and the activity was suggested to be related to the elution content of eriocitrin, which is an
antioxidant in niihime fruit. This study showed that niihime fruit contains a comparative abundance of bioactive flavonoids and these
flavonoids are able to be eluted using hot solns. of water and ethanol.
Answer 292:
Synthesis and characterization of some nitro-substituted 3,5-diarylisoxazolines, thioisoxazolines, and their derivatives.
Parmar, P. J.; Rajput, S. I. Department of Chemistry, B.P. Arts, S.M.A. Science and K.K.C. Commerce College, Chalisgaon,
India. Asian Journal of Chemistry (2007), 19(2), 1519-1523. Publisher: Asian Journal of Chemistry, CODEN: AJCHEW ISSN:
Abstract
Chalcones or flavanones were reacted with ethanol, hydroxylamine hydrochloride and aq. KOH to give isoxazolines I (X = O with R =
R1 = H; R = OMe, R1 = H; R = H, R1 = NO2; RR1 = OCH2O). Subsequent reaction with P2S5 under reflux with pyridine gave
thioisoxazolines I (X = S; II), while treatment with Ac2O and a pinch of anhyd. NaOAc yields 3-(2-acetoxy)isoxazolines.
Thioisoxazolines II reacted with Ac2O in presence of anhyd. NaOAc to give 3-(2-acetoxy)thioisoxazolines.
R1
OH N X
O2 N R
Me I
Answer 293:
Method for producing chrysanthemum cultivar of which flower color is changed from red to yellow according to flowering
time, and chrysanthemum cultivar produced thereby. Liu, Jang Ryol; Seo, Jin Wook; Kim, Suk Weon; Oh, Seung Cheol; Cha,
Hyun Wook. (Korea Research Institute of Bioscience and Biotechnology, S. Korea). Repub. Korean Kongkae Taeho Kongbo (2006),
flavanone
No pp. given. CODEN: KRXXA7 KR 2006080067 A 20060707 Patent written in Korean. Application: KR 2005-609 20050104.

KR 2006080067 A 20060707 KR 2005-609 20050104
KR 2005-609 20050104
Abstract
A method for producing novel Chrysanthemum cultivar and the Chrysanthemum cultivar produced thereby are provided to change the
flower color of Chrysanthemum cultivar from red to yellow according to the flowering time by inserting flavonoid 3',5'-hydroxylase
gene into the Chrysanthemum cultivar. The method for producing Chrysanthemum cultivar comprises the steps of: (a) inserting the
genes assocd. with anthocyanin biosynthesis into the Agrobacterium; (b) inducing the adventitious bud from the cotyledon or embryo
axis segment of Chrysanthemum; (c) co-culturing the Agrobacterium of step (a) with the induced adventitious bud to introduce the
genes assocd. with anthocyanin biosynthesis into the adventitious bud; (d) selecting the transformed adventitious bud; and (e)
regenerating the selected adventitious bud, wherein the gene assocd. with anthocyanin biosynthesis is selected from chalcone
synthase (CHS) gene, chalcone isomerase (CHI) gene, flavanone 3-hydroxylase (F3H) gene, flavonoid 3'-hydroxylase (F3'H) gene,
flavonoid 3', 5'-hydroxylase (F3',5'H) gene, dihydroflavonol 4-reductase (DFR) gene, anthocyanidin synthase (ANS) gene and
flavonoid glucosyl transferase (FGT) gene.
Answer 294:
Heterosmilax extract, and its preparation method and application in treating tumors. Lin, Ruichao; Wang, Gangli; Dai,
Zhong; Yao, Lingwen; Qin, Wenjie. (National Research Center of Pharmaceutical and Biological Products Standardization, Peop. Rep.
China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 19pp. CODEN: CNXXEV CN 1903340 A 20070131 Patent
written in Chinese. Application: CN 1008-9055 20060801. Priority: . CAN 146:280892 AN 2007:132062 CAPLUS (Copyright

CN 1903340 A 20070131 CN 2006-10089055 20060801
CN 2006-10089055 20060801
Abstract
The title Heterosmilax ext. contains phenolic glycosides not less than 10% and flavonoid glycosides not less than 10%. The title
method comprises: (1) extg. Heterosmilax with 10-95% alc., concg., suspending in water, standing, and filtering, (2) performing liq.-liq.
flavanone
extn. with low-polarity solvent (petroleum ether, Et ether, acetone, and isopropanol), medium-polarity solvent (chloroform and/or Et
acetate) and high-polarity solvent (n-butanol) in order, and (3) feeding into macroporous resin, eluting with water until the eluate exhibits
neg. reducing sugar reaction, eluting with 90% alc. to collect eluate, and concg. The ext. has antitumor activity, and can be used in
manuf. of antitumor drugs.
Answer 295:
Disordered 4'-hydroxyflavanone. Bialonska, Agata; Ciunik, Zbigniew; Kostrzewa-Suslow, Edyta; Dmochowska-Gladysz, Jadwiga.
Faculty of Chemistry, University of Wroclaw, Wroclaw, Pol. Acta Crystallographica, Section E: Structure Reports Online (2007),
E63(2), o432-o433. Publisher: Blackwell Publishing Ltd., CODEN: ACSEBH ISSN: 1600-5368.
http://journals.iucr.org/e/issues/2007/02/00/lh2267/lh2267.pdf Journal; Online Computer File written in English. CAN 146:510790
Abstract
Unlike the crystals of 4'-hydroxyflavanone, C15H12O3 obtained from a MeOH soln. (Shoja, M., 1998), in crystals grown from a
hexane-acetone mixt. (10:1), both the S and R enantiomers appear to occupy in a random way the 4 symmetry-equiv. sites of the unit
cell in an .apprx.4:1/1:4 ratio.
Answer 296:
Disordered 6-hydroxyflavanone. Bialonska, Agata; Ciunik, Zbigniew; Kostrzewa-Suslow, Edyta; Dmochowska-Gladysz, Jadwiga.
Faculty of Chemistry, University of Wroclaw, Wroclaw, Pol. Acta Crystallographica, Section E: Structure Reports Online (2007),
E63(2), o430-o431. Publisher: Blackwell Publishing Ltd., CODEN: ACSEBH ISSN: 1600-5368.
http://journals.iucr.org/e/issues/2007/02/00/lh2266/lh2266.pdf Journal; Online Computer File written in English. CAN 146:510789
Abstract
In contrast to M. Shoja et al.'s (1998) crystal structure of 6-hydroxyflavanone, C15H12O3, in the present crystal structure, both S and
R enantiomers appear to occupy randomly the 4 crystallog. sites of the unit cell in an .apprx.3:1/1:3 ratio. Crystallog. data are given.
Answer 297:
Quantitation of bioactive compounds in citrus fruits cultivated in Taiwan. Wang, Yuan-Chuen; Chuang, Yueh-Chueh; Ku,
Yu-Hua. Department of Food Science and Biotechnology, National Chung Hsing University, Taichung, Taiwan. Food Chemistry
(2007), 102(4), 1163-1171. Publisher: Elsevier B.V., CODEN: FOCHDJ ISSN: 0308-8146. Journal written in English. CAN
Abstract
The aim of this study was to det. the levels of bioactive compds. in the edible portions of 8 varieties of citrus fruits (Ponkan, Tonkan,
Murcott, Wendun, Peiyou, Kumquat, Liucheng, and Lemon) cultivated in Taiwan. The amt. of total polyphenol and flavonoid exceeded
flavanone
that of total carotenoid. Hesperidin was the major flavanone, which abounded in Liucheng and Tonkan (5.36 ± 0.145 and 4.13 ± 0.050
mg/g db, resp.). Naringin abounded in Peiyou and Wendun (1250 ± 0.82 and 2205 ± 11.1 μg/g db, resp.). Diosmin was the major
flavone, and Kumquat (0.699 ± 0.021 mg/g db) and Lemon (0.323 ± 0.004 mg/g db) had the highest contents. Kaempferol was the
most abundant flavanol except in Wendun, Peiyou, and Kumquat, and Murcott had the highest content (1.04 ± 0.007 mg/g db).
Chlorogenic acid was the major phenolic acid, and Wendun and Lemon had the highest contents (103 ± 11.5 and 92.6 ± 8.90 μg/g db,
resp.). β-Cryptoxanthin was the main carotenoid (0.764 ± 0.031-6.67 ± 0.329 μg/g db), followed by β-carotene (0.435 ± 0.016-3.77 ±
0.154 μg/g db), and these 2 compds. abounded in Murcott. Tonkan, Wendun, Peiyou, and Lemon had high levels of ascorbic acid.
Total pectin levels ranged from 40.4 ± 1.65 to 87.3 ± 3.69 mg/g db.
Answer 298:
Synthesis of dispiro[flavanone/chromanone/tetralone]-pyrrolo[1,2-a]isoquinolinespiro[3.2'']acenaphthen-1''-one systems

through three component 1,3-dipolar cycloaddition reaction. Jayashankaran, Jayadevan; Manian, Rathna Durga R. S.;
Raghunathan, Raghavachary. Laboratoire de Chimie Moleculaire et Thioorganique (LCMT) UMR CNRS 6507, Ensicaen et Universite
de Caen Basse Normandie, Caen, Fr. Letters in Organic Chemistry (2006), 3(12), 917-921. Publisher: Bentham Science
Publishers Ltd., CODEN: LOCEC7 ISSN: 1570-1786. Journal written in English. CAN 148:33601 AN 2007:123306 CAPLUS
Abstract
The cycloaddn. reaction of non-stabilized azomethine ylides with (E)-3-arylidene-4-flavanone, (E)-3- arylidene-4-chromanone and
(E)-2-arylidene-1-tetralone as dipolarophiles has been investigated. High degree of regioselectivity has been obsd. in the synthesis of
a new class of functionalized dispiroheterocyclic compd. contg. dispiro pyrroloisoquinoline and acenaphthequinone framework.
Answer 299:
Chemical constituents of Nepalese propolis: isolation of new dalbergiones and related compounds. Shrestha, Suraj
Prakash; Narukawa, Yuji; Takeda, Tadahiro. Kyoritsu University of Pharmacy, 1-5-30 Shibakoen, Minato-ku, Tokyo, Japan.
Journal of Natural Medicines (2007), 61(1), 73-76. Publisher: Springer Tokyo, CODEN: JNMOBN Journal written in English. CAN
Abstract
Two new dalbergiones (1-2) and a new flavanone (3) were isolated along with nine other known flavonoids (4-12) from the methanolic
ext. of propolis collected from Chitwan, Nepal. The structures were detd. on the basis of spectral anal.
Answer 300:
A new flavanone from the leaves of Cassia alata. Rahman, M. S.; Hasan, A. J. M. Moynul; Ali, M. Y.; Ali, M. U. BCSIR
Laboratories, Rajshahi, Bangladesh. Bangladesh Journal of Scientific and Industrial Research (2005), 40(1-2), 123-126. Publisher:
Bangladesh Council of Scientific and Industrial Research, CODEN: BJSIBL ISSN: 0304-9809. Journal written in English. CAN
flavanone
Abstract
Studies were carried out on the leaves of Cassia alata. A new flavanone 5,7,4'-trihydroxy flavanone was isolated from the leaves of
Cassia alata with the help of column and thin layer chromatog. using a gradient of org. solvents with increasing polarity. The compd.
was characterized on the basis of UV, IR, 1H-NMR and Mass spectrometry.
Answer 301:
Isolation and purification of prenylated flavonoids from Patrinia villosa Juss by reversed phase preparative liquid
chromatography. Peng, Jinyong; Fan, Guorong; Wu, Yutian; Chen, Hongyuan. Shanghai Key Laboratory for Drug Metabolism,
College of Pharmacy, The Second Military Medical University, Shanghai, Peop. Rep. China. Fenxi Huaxue (2006), 34(7),
983-986. Publisher: Kexue Chubanshe, CODEN: FHHHDT ISSN: 0253-3820. Journal written in Chinese. CAN 146:149251 AN
Abstract
A semi-preparative reversed phase liq. chromatog. (RPLC) was used to isolate the chem. constituents from the chloroform ext. of
Patrinia villosa Juss. The sepn. condition was optimized as follows: the column was YWG C18 (10.0 mm × 200 mm i.d., 10 μm), the
mobile phase was composed of CH3CN-H2O-HAC (55:45:2, V/V) at a flow rate of 4.0 mL/min, the detection wavelength and sample
size were set at 280 nm and 750 μL (30 g/L). Under the optimized conditions, five compds. were isolated by RPLC in one run. Their
chem. structures were identified as bolusanthol B (1); (2S)-5,7,2',6'-tetrahydroxy-6-lavandulylated flavanone (2);
(2S)-5,2',6'-trihydroxy-2",2"-dimethylpyrano[5",6":6,7]flavanone (3); orotinin (4) and orotinin-5-Me ether (5) by spectroscopic methods
including UV, IR, electrospray mass spectrometry, one-dimensional NMR and two-dimensional NMR techniques. Among them,
compds. 2 and 3 were new compds., and compds. 1, 4 and 5 were isolated from the P. genius for the first time.
Answer 302:
The effects of total flavanones from alpinia officinarum Rhizoma extracts on the activity of isolated ileum muscle in rabbits.
Tang, Chunping; Jiang, Tao; Chen, Shaoyi; Chen, Yanfen; Yang, Chaoyan. Research Institute of Chinese Mater. Med. Pharmacol.,
Guangdong College of Pharmacy, Guangzhou, Peop. Rep. China. Zhongyao Yaoli Yu Linchuang (2006), 22(5), 23-25. Publisher:
Zhongyao Yaoli Yu Linchuang Bianjibu, CODEN: ZYYLBL ISSN: 1001-859X. Journal written in Chinese. CAN 146:415023 AN
Abstract
The mechanism of total flavanone from Alpinia Officinarum Rhizoma (AOR) exts. on the ileum myoelec. activity of rabbits in vitro was
studied. The samples of isolated ileum segment were prepd., the contraction intensity were measured. Effects of AOR exts. on the
contraction induced by BaCl2, histamine and actions on 2-component contraction evoked by ACh in the rabbit ileum were studied.
Results showed that AOR exts. could significantly inhibit spontaneous constriction of ileum, exert an inhibitory effect on the
contraction induced by BaCl2, histamine. It also inhibited the inflow of intracellular Ca2+ induced by ACh. It was concluded that AOR
exts. could restrain the contraction on the rabbit ileum, this effect could be related to Ca2+ channel, M-receptor, H-receptor and direct
action.
Answer 303:
flavanone
Implantable medical devices comprising flavonoids' coating for prevention of restenosis. Managoli, Nandkishore.
(Sahajanand Biotech Private Limited, India). PCT Int. Appl. (2007), 30pp. CODEN: PIXXD2 WO 2007010342 A1 20070125
EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT,
LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL,
SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE,
2006-IB1848 20060626. Priority: EP 2005-106528 20050715; US 2005-699509 20050715. CAN 146:190620 AN 2007:87257

WO 2007010342 A1 20070125 WO 2006-IB1848 20060626
CA 2617728 A1 20070125 CA 2006-2617728 20060626
GB 2443576 A 20080507 GB 2008-1525 20060626
EP 2005-106528 A 20050715
US 2005-699509P P 20050715
WO 2006-IB1848 W 20060626
Abstract
The present invention relates to implantable medical devices, such as stents, that comprise a compn. for controlled delivery of
flavonoids or a deriv. thereof. The flavonoids are aimed at preventing or reducing secondary complications which can occur following
implantation of the device such as e.g. occlusive and catastrophic vascular phenomena. The invention further relates to the inclusion
of addnl. therapeutic agents in the system that may have antiproliferative, antimitotic, antimicrobial, anticoagulant, fibrinolytic,
anti-inflammatory, immunosupressive, and anti-angiogenic activities. The compn. comprising the flavonoids and optional further
therapeutic agents may be used in methods for treating or preventing narrowing or obstruction of a body passageway. In particular the
devices and compns. of the invention are useful in methods for treating or preventing restenosis, e.g. subsequent to angioplasty
and/or for preventing or reducing acute, subacute and chronic secondary complications assocd. with angioplasty, such as e.g.
thrombus. For example, a stent made from 316L was coated with paclitaxel and genistein dissolved in polymers solns. of
poly(L-lactide), poly(glycolide-lactide) and polyvinyl pyrrolidone with dichloromethane as the solvent.
Answer 304:
A new flavanone and a new flavanone glycoside from Scutellaria baicalensis. Yin, Jun Gang. Department of Applied
flavanone
Chemistry, Yantai University, Yantai, Peop. Rep. China. Chinese Chemical Letters (2006), 17(11), 1457-1459. Publisher:
Chinese Chemical Society, CODEN: CCLEE7 ISSN: 1001-8417. Journal written in English. CAN 146:354687 AN 2007:69112
Abstract
A new flavanone (2S)-5,7,2',5'-tetrahydroxyflavanone (1) together with a new flavanone glycoside (2S)-5,7,2',5'-tetrahydroxyflavanone
7-O-β-D-glucopyranoside (2), were isolated from the dry roots of S. baicalensis. Their structures were elucidated on the basis of
spectroscopic data.
Answer 305:
ADME data for polyphenols characterized by reversed-phase thin-layer chromatography. Mornar, Ana; Medic-Saric, Marica;
Jasprica, Ivona. Department of Medicinal Chemistry, University of Zagreb, Zagreb, Croatia. Journal of Planar
Chromatography--Modern TLC (2006), 19(112), 409-417. Publisher: Research Institute for Medicinal Plants, CODEN: JPCTE5
ISSN: 0933-4173. Journal written in English. CAN 147:419280 AN 2007:67019 CAPLUS (Copyright (C) 2008 ACS on SciFinder
(R))
Abstract
The chromatog. behavior of polyphenols (flavonoids and phenolic acids) was studied by reversed-phase thin-layer chromatog.
(RP-TLC) to establish relations between chromatog. data and selected ADME (absorption, distribution, metab., and elimination) data.
Good correlation between chromatog. RM values (a measure of the interactions of the solute with the lipophilic stationary phase and
with the hydrophilic mobile phase) and the concn. of the buffer in the mobile phase (r ≥ 0.994) might be taken as a measure of the
suitability of the system for estn. of the lipophilicity of the polyphenols. Exptl. obtained RMw values (a measure of the interactions of
the solute with the lipophilic stationary phase and with pure water as mobile phase) and ϕ0 (the vol. fraction of org. modifier/buffer in
the mobile phase for which retention is zero) were compared with ADME data calcd. by software packages based on different theor.
approaches. From the authors' results the authors could establish correlations between chromatog. behavior and lipophilicity, soly.,
plasma-protein binding, and oral absorption of the polyphenols studied.
Answer 306:
Compositions for treating or preventing obesity, insulin resistance and mitochondrial-associated disorders. Milburn,
Michael; Milne, Jill; Auwerx, Johan; Argmann, Carmen; Lagouge, Marie; Dipp, Michelle. (Sirtris Pharmaceuticals, Inc., USA). PCT Int.
Appl. (2007), 337pp. CODEN: PIXXD2 WO 2007008548 A2 20070118 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA,
BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HN, HR,
HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA,
NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ,
VC. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG,
CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2006-US26272 20060707. Priority: US
2005-697443 20050707; US 2005-736528 20051114; US 2005-753606 20051223; US 2006-783802 20060316. CAN 146:169320

flavanone
WO 2007008548 A2 20070118 WO 2006-US26272 20060707

WO 2007008548 A3 20070809
EP, OA
US 20070149466 A1 20070628 US 2006-374295 20060316
AU 2006269459 A1 20070118 AU 2006-269459 20060707
CA 2613141 A1 20070118 CA 2006-2613141 20060707
EP 1898897 A2 20080319 EP 2006-786429 20060707
US 2005-697443P P 20050707
US 2005-736528P P 20051114
US 2005-753606P P 20051223
US 2006-783802P P 20060316
WO 2006-US26272 W 20060707
Abstract
Provided herein are methods and compns. for treating or preventing metabolic disorders, such as obesity and diabetes. Methods may
comprise modulating the activity or level of a sirtuin, such as SIRT1 or Sir2. Exemplary methods comprise contacting a cell with a
sirtuin activating compd., such as a flavone, stilbene, flavanone, isoflavone, catechin, chalcone, tannin or anthocyanidin, or an
inhibitory compd., such as nicotinamide. Resveratrol increases the PGC-1 protein deacetylation.
Answer 307:
Flavonoids and the Risk of Renal Cell Carcinoma. Bosetti, Cristina; Rossi, Marta; McLaughlin, Joseph K.; Negri, Eva; Talamini,
Renato; Lagiou, Pagona; Montella, Maurizio; Ramazzotti, Valerio; Franceschi, Silvia; LaVecchia, Carlo. Istituto di Ricerche
Farmacologiche "Mario Negri", Universita degli Studi di Milano, Milan, Italy. Cancer Epidemiology, Biomarkers & Prevention (2007),
16(1), 98-101. Publisher: American Association for Cancer Research, CODEN: CEBPE4 ISSN: 1055-9965. Journal written in
Abstract
Intake of flavonoids has been inversely related to the risk of various common neoplasms, but limited data exist on renal cell
carcinoma (RCC). We used data from a case-control study conducted between 1994 and 2002 in four Italian areas to study the
relation between major flavonoid classes and RCC. The study included 767 cases with incident, histol. confirmed RCC and 1,534
flavanone
hospital controls admitted for acute, nonneoplastic conditions and matched with cases by study center, sex, and quinquennia of age.
We applied published data on food and beverage content of six major classes of flavonoids to dietary information collected through a
validated food frequency questionnaire. After adjustment for major recognized confounding factors and total energy intake, the odds
ratios for subjects in the highest vs. the lowest quintile of intake were 0.80 [95% confidence interval (95% CI), 0.58-1.11] for total
flavonoids, 0.76 (95% CI, 0.56-1.03) for isoflavones, 0.94 (95% CI, 0.60-1.47) for anthocyanidins, 0.77 (95% CI, 0.56-1.06) for
flavan-3-ols, 0.90 (95% CI, 0.67-1.21) for flavanones, 0.68 (95% CI, 0.50-0.93) for flavones, and 0.69 (95% CI, 0.50-0.95) for
flavonols. Allowance for vegetable and fruit consumption only partly explained these inverse relations. Thus, flavonoids, and
particularly flavones and flavonols, may account, at least in part, for the favorable role of plant foods on RCC.
Answer 308:
Kinetic study of the photosensitized oxygenation of the flavanone naringin and its chalcone. Montenegro, Mariana A.;
Nazareno, Monica A.; Borsarelli, Claudio D. Instituto de Ciencias Quimicas, Facultad de Agronomia y Agroindustrias, Universidad
Nacional de Santiago del Estero, Santiago del Estero, Argent. Journal of Photochemistry and Photobiology, A: Chemistry (2007),
186(1), 47-56. Publisher: Elsevier B.V., CODEN: JPPCEJ ISSN: 1010-6030. Journal written in English. CAN 147:448986 AN
Abstract
The kinetic of the O2(1Δg)-photosensitized oxidn. of the flavanone naringin (7-rhamnoglucosyl-4',5-dihydroxyflavanone, FL) and its
chalcone isomer (4'-rhamnoglucosyl-2',6',4-trihydroxychalcone, CH) in neutral and 1 mM NaOH ethanol solns. was studied using Rose
Bengal as photosensitizer. The rate consts. for the chem. quenching of O2(1Δg) by the flavonoids (kr) were detd. using either UV-vis
absorption spectroscopy or HPLC techniques, and for the total (phys. + chem.) quenching (k t) were detd. using time-resolved
phosphorescence detection of O2(1Δg) at 1270 nm. A larger reactivity towards O2(1Δg) of CH than for FL in neutral ethanol solns.
was obsd., due to the extra conjugated double bond in CH. However, in alk. media the reactivity of both isomers was larger than in
neutral conditions. This behavior was assocd. to the increment of electron d. by the formation of a carbanion in FL and to the
presence of the extended conjugated π-system in the CH isomer by deprotonation of phenolic groups. In all cases, the formation of
4-hydroxybenzoic acid as ending product was detected by HPLC. Based on reported mechanisms of O2(1Δg)-mediated oxidn. of
flavonoids, the formation of 7-rhamnoglucosyl-5,4'-dihydroxyflavonol as primary photo-oxidn. product was proposed. The reactivity
towards O2(1Δg) of the aglycon of naringin (5,7,4'-trihydroxyflavanone or naringenin, NG) in alk. conditions was lower than for the
parent naringin, due to incapability of NG to form a carbanion species. These results are expected to have significance in
biosynthesis, antioxidant properties and stability of naturally occurring flavonoids.
Answer 309:
Differentiation of juices from clementine (Citrus clementina), clementine-hybrids and satsuma (Citrus unshiu) cultivars by
statistical multivariate discriminant analysis of their flavanone-7-O-glycosides and fully methoxylated flavones content as
determined by liquid chromatography. Sentandreu, E.; Izquierdo, L.; Sendra, J. M. Instituto de Agroquimica y Tecnologia de
Alimentos, Burjassot, Spain. European Food Research and Technology (2007), 224(4), 421-429. Publisher: Springer GmbH,
CODEN: EFRTFO ISSN: 1438-2377. Journal written in English. CAN 146:357444 AN 2007:41444 CAPLUS (Copyright (C)
Abstract
Mandarin juices from 3 pure clementine (Citrus clementina Hort. ex Tan.) cultivars: Clemenules, Hernandine and Marisol, 3
clementine-hybrids: Nova (clementine×tangelo Orlando), Ortanique (clementine×orange) and Fortune (clementine×mandarin Dancy) and
one satsuma (Citrus unshiu Marc) cultivar: Clauselline were analyzed for simultaneous detn. of their flavanone-7-O-glycosides (FGs)
flavanone
and fully methoxylated flavones (FMFs) content, using HPLC. Statistical multivariate discriminant anal. from the FGs concn. data
showed that its discriminant power was rather poor, leading to overlapping between some groups of the assayed cultivars. By
contrast, the discriminant power from the FMFs concn. data was very high and only two concn. ratios were needed as discriminant
parameters to significantly differentiate between all the assayed cultivars. Moreover, the values of the discriminant parameters were
almost independent of the location of the orchards and the maturity stage of the fruits.
Answer 310:
Flavonoids from Rosa damascena Mill. Kumar, Neeraj; Singh, Bikram; Kaul, Vijay K. Natural Plant Products Division, Institute
of Himalayan Bioresource Technology, Palampur, India. Natural Product Communications (2006), 1(8), 623-626. Publisher:
Natural Product Communications, CODEN: NPCACO ISSN: 1555-9475. Journal written in English. CAN 146:334108 AN
Abstract
A new flavanone glycoside, butin 4'-O-(2''-O-β-D-apiofuranosyl)-β-D-glucopyranoside (1), together with liquiritin (2), liquiritin apioside (3),
isoliquiritin apioside (4), davidioside (5), quercetin (6), kaempferol (7), kaempferol 3-O-β-D-glucopyranoside (8) and kaempferol
3-O-α-L-arabinofuranoside (9) were isolated from the marc of R. damascena flowers after industrial distn. of essential oil. This is the
1st report of the occurrence of compds. 2, 3, 4 and 5 in R. damascena. The structures of the isolated constituents were established
on the basis of spectroscopic {UV, IR, 1D, 2D NMR (DEPT, HMQC, HMBC and COSY)}, spectrometric (ESI-QTOF-MS), and chem.
evidence.
Answer 311:
Radical scavenging-flavonoids from Erythrina abyssinica. Machumi, Francis; Bojase-Moleta, Gomotsang; Mapitse,
Renameditswe; Masesane, Ishmael; Majinda, Runner R. T. Department of Chemistry, University of Botswana, Gaborone,
Botswana. Natural Product Communications (2006), 1(4), 287-292. Publisher: Natural Product Communications, CODEN:
NPCACO ISSN: 1555-9475. Journal written in English. CAN 147:48600 AN 2007:34673 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
Phytochem. anal. of twigs and roots of Erythrina abyssinica, a traditionally used medicinal plant, gave a new radical scavenging
flavanone, 7,3',4'-trihydroxy-5'-prenylflavanone (abyssinone VII; 1), along with 21 known compds., whose radical scavenging and
antimicrobial activities were also assessed.
Answer 312:
Anti-inflammatory agents containing natural products from Angelica keiskei. Akihisa, Toshihiro; Yasukawa, Tadashi; Ukiya,
Motohiko; Hasegawa, Daisuke. (Nihon University, Japan). Jpn. Kokai Tokkyo Koho (2007), 14pp. CODEN: JKXXAF JP
flavanone

JP 2007001898 A 20070111 JP 2005-182196 20050622
JP 2005-182196 20050622
Abstract
Title agents contain chalcones I [R = OH, OMe; R1 = prenyl, geranyl, CH2CH(OH)CMe:CH2, CH2CH2CMe(OH)CH2CH2CH:CMe2; R1
and the adjacent OH may be linked to form 6-membered substituted ring], coumarins II (R6 = H, OH, O2CCMe:CHMe, O2CCH:CMe2),
coumarin deriv. III , and/or flavanones IV (R7 = H, OH, OMe; R8 = OH, OMe; R9 prenyl, geranyl; R10 = H, geranyl) as active
ingredients. Thus, 13 compds. isolated from A. keiskei inhibited TPA-induced edema in mouse ears. The ID50 value of
4-hydroxyderricin was 68 μg/ear, vs. 300 μg/ear, for indomethacin.
OH
R
O O O
Me
R1 Me R6
OH O I R5 II
OR 10
R9
HO O O R8 O
Me Me III R7 O IV
Answer 313:
New insight into the ring contraction of 2'-benzyloxyflavanones. Nemeth, Istvan; Gulacsi, Katalin; Antus, Sandor; Keki,
Sandor; Zsuga, Miklos. Department of Organic Chemistry, University of Debrecen, Debrecen, Hung. Natural Product
Communications (2006), 1(11), 991-996. Publisher: Natural Product Communications, CODEN: NPCACO ISSN: 1555-9475.
Abstract
flavanone
The reactions of 2'-benzyloxyflavanones I (RR1 = OCH2O; R = OMe, R1 = H) with thallium(III) nitrate or iodobenzene diacetate in the
presence of perchloric or sulfuric acid in tri-Me orthoformate was studied. Depending on the substitution pattern and the conditions,
these compds. underwent 2-aryl migration and/or ring contraction and dehydrogenation. A probable mechanism of these
transformations is discussed.
R
OCH 2 Ph
R1 O
Answer 314:
Carbon-13 NMR chemical shift of methyl group: a useful parameter for structural analysis of C-methylated flavonoids.
Agrawal, Pawan K.; Agrawal, Chandan; Agrawal, Shravan. Natural Product Inc., Westerville, OH, USA. Natural Product
Communications (2006), 1(11), 957-959. Publisher: Natural Product Communications, CODEN: NPCACO ISSN: 1555-9475.
Abstract
The 13C NMR resonances corresponding to the C-Me group of C(6) and/or C(8) C-methylated-flavonoids absorb between 6.7-10.0 ppm
and typically between 6.7-8.7 ppm. A comparative 13C NMR study reflects that the 13C NMR chem. shifts reported for
6-hydroxy-5-methyl-3',4',5'-trimethoxyaurone-4-O-α-L-rhamnoside from Pterocarpus santalinus and
C(8)-methyl-5,7,2',4'-tetramethoxyflavanone from Terminalia alata are inconsistent with the assigned structures, and therefore need
reconsideration.
Answer 315:
Processes for the preparation of protected-(+)-catechin and (-)-epicatechin monomers, for coupling the protected monomers
with an activated, protected epicatechin monomer, and for the preparation of epicatechin-(4b,8)-epicatechin or -catechin
dimers and their digallates. Romanczyk, Leo; Sharma, Pradeep K.; Kolchinski, Alexander G.; Shea, Helene A.; Gou, Yanni.
(USA). U.S. Pat. Appl. Publ. (2007), 9pp. CODEN: USXXCO US 2007004796 A1 20070104 Patent written in English.
Application: US 2005-169860 20050629. Priority: . CAN 146:121750 AN 2007:17789 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))

US 20070004796 A1 20070104 US 2005-169860 20050629
AU 2006266287 A1 20070111 AU 2006-266287 20060619
CA 2611878 A1 20070111 CA 2006-2611878 20060619
flavanone
WO 2007005248 A2 20070111 WO 2006-US23698 20060619

WO 2007005248 A3 20070726
KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ,
OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG,
US, UZ, VC, VN, ZA, ZM, ZW
EP, OA
EP 1896444 A2 20080312 EP 2006-773470 20060619
US 2005-169860 A 20050629
WO 2006-US23698 W 20060619
Abstract
Improved processes for the prepn. of tetra-O-benzyl protected catechin (I), for the coupling of the tetra-O-benzyl protected catechin or
epicatechin (II) with a C-4 activated, tetra-O-benzyl protected epicatechin for the galloylation of the epicatechin-(4β,8)-catechin or
-epicatechin dimer-the dimer digallates, and for the deprotection (i.e., debenzylation) of the protected epicatechin dimers and protected
epicatechin dimer digallates are disclosed.
OH OH
OH OH
HO O HO O
OH OH
OH OH
I II
Answer 316:
Production of soybean isoflavone genistein in non-legume plants via genetically modified secondary metabolism pathway.
Liu, Rongrong; Hu, Yuanlei; Li, Jialin; Lin, Zhongping. National Laboratory of Protein Engineering and Plant Genetic Engineering,
Peking University, Beijing, Peop. Rep. China. Metabolic Engineering (2007), 9(1), 1-7. Publisher: Elsevier B.V., CODEN:
MEENFM ISSN: 1096-7176. Journal written in English. CAN 146:291720 AN 2007:12422 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
flavanone
Abstract
Genetic modification of secondary metabolic pathways to produce desirable natural products is an attractive approach in plant
biotechnol. In our study, we attempted to produce a typical soybean isoflavone genistein, a well-known health-promoting metabolite, in
non-legume plants via genetic engineering. Both overexpression and antisense suppression strategies were used to manipulate the
expression of several genes encoding key enzymes in the flavonoids/isoflavonoids pathway in transgenic tobacco, lettuce, and
petunia. Introducing soybean isoflavone synthase (IFS) into these plants, which naturally do not produce isoflavonoids due to a lack
of this leguminous enzyme, resulted in genistein biosynthesis in tobacco petals, petunia leaves and petals, and lettuce leaves. In
tobacco, when flavanone 3-hydroxylase (F3H) expression was suppressed by its antisense gene while soybean IFS was
overexpressed at the same time, genistein yield increased prominently. In addn., overexpression of phenylalanine ammonia-lyase
(PAL) also led to an enhanced genistein prodn. in tobacco petals and lettuce leaves in the presence of IFS than in the plants that
overexpressed only IFS.
Answer 317:
Topical aromatase inhibitors and estradiol receptor blockers for treatment of wrinkles. Okigami, Henry; Okigami, Paulo
Takao. (Brazil). Braz. Pedido PI (2005), 10pp. CODEN: BPXXDX BR 2004000668 A 20051011 Patent written in Portuguese.
Application: BR 2004-668 20040220. Priority: . CAN 146:49750 AN 2007:3240 CAPLUS (Copyright (C) 2008 ACS on SciFinder
(R))

BR 2004000668 A 20051011 BR 2004-668 20040220
BR 2004-668 20040220
Abstract
Topical formulations are disclosed that contain aromatase P 450 and/or estrogen receptor blockers (particularly tamoxifen) for
treatment or prevention of wrinkles. Active agents are present at 0.1-5.0%.
Answer 318:
Biodiversity conservation and drug discovery in madagascar, part 22: cytotoxic compounds of Physena madagascariensis
from the Madagascar rain forest. Cao, Shugeng; Norris, Andrew; Miller, James S.; Ratovoson, Fidy; Birkinshaw, Chris;
Andriantsiferana, Rabodo; Rasamison, Vincent E.; Rakotonandrasana, Stephan; Kingston, David G. I. Department of Chemistry,
Virginia Polytechnic Institute and State University, Blacksburg, VA, USA. Natural Product Research, Part A: Structure and
Synthesis (2006), 20(13), 1157-1163. Publisher: Taylor & Francis Ltd., CODEN: NPRPC8 Journal written in English. CAN
Abstract
flavanone
Two new flavanones, remangiflavanones D and E (1 and 2), were isolated from an ext. of the twigs, leaves, and flowers of Physena
madagascariensis together with 3 known flavanones, remangiflavanones A-C (3-5), and (E)-N-feruloyltyramine (6). The structures of
the new compds. 1 and 2 were established on the basis of one-dimensional and two-dimensional NMR spectroscopic data interpretation.
All compds. were evaluated for their cytotoxicity in the A2780 human ovarian cancer cell line. Compd. 5 was the most active with an
IC50 value of 2.5 μg mL-1.
Answer 319:
Induction of polyphenol gene expression in apple (Malus × domestica) after the application of a dioxygenase inhibitor.
Fischer, Thilo C.; Halbwirth, Heidrun; Roemmelt, Susanne; Sabatini, Emidio; Schlangen, Karin; Andreotti, Carlo; Spinelli, Francesco;
Costa, Guglielmo; Forkmann, Gert; Treutter, Dieter; Stich, Karl. Lehrstuhl fuer Zierpflanzenbau, Department fuer
Pflanzenwissenschaften, Technische Universitaet Muenchen Weihenstephan, Freising, Germany. Physiologia Plantarum (2006),
128(4), 604-617. Publisher: Blackwell Publishing Ltd., CODEN: PHPLAI ISSN: 0031-9317. Journal written in English. CAN
Abstract
A comprehensive study of the complex polyphenol biosynthesis in developing leaves of apple (Malus domestica) was performed
comprising gene expression, enzyme activities and polyphenol compn. During leaf development, an early increase in gene expression
was obsd. for phenylalanine ammonia lyase (PAL, EC 4.3.1.5), chalcone synthase (CHS, EC 2.3.1.74), flavanone 3-hydroxylase
(FHT, EC 1.14.11.9) and dihydroflavonol 4-reductase/flavanone 4-reductase (DFR/FNR, EC 1.1.1.219). Their enzyme activities
showed a corresponding trend during the time course. A parallel set of expts. was carried out with leaves treated with prohexadione-Ca
(ProCa), which is an enzyme inhibitor of 2-oxoglutarate dependent dioxygenases (2-ODDs). ProCa is known to induce changes in
polyphenol biosynthesis, which are accompanied by a reduced incidence of fire blight and scab, the two major pome fruit diseases.
The application of ProCa led to an increase in activities of PAL, CHS, FHT and DFR/FNR, which was based on an enhanced gene
expression. In contrast, an inhibition of gene expression was detected for anthocyanidin synthase (EC 1.14.11.19). These effects are
interpreted as a feedback regulation by changed polyphenol levels. Because of the inhibition of the 2-ODDs FHT and flavonol
synthase (EC 1.14.11.23), some pronounced changes in polyphenol compn. were obsd. Eriodictyol, the substrate of FHT,
accumulated as eriodictyol-7-O-glucoside and 6''-O-trans-p-coumaroyleriodictyol 3'-O-glucoside. In addn., the 3-deoxycatechin
luteoliflavan was formed which is not present in untreated apple leaves. Hence, beyond the redirection of polyphenol biosynthesis by
the enzyme inhibitor, changed polyphenol levels obviously cause a distinct induction of gene expression by feedback regulation.
Answer 320:
(+)-Apollineanin: a new flavanone from Tephrosia apollinea. Hisham, A.; John, Shaly; Al-Shuaily, Wafa; Asai, Teigo; Fujimoto,
Yoshinori. Department of Chemistry, College of Science, Sultan Qaboos University, Al-Khode, Oman. Natural Product
Research, Part A: Structure and Synthesis (2006), 20(12), 1046-1052. Publisher: Taylor & Francis Ltd., CODEN: NPRPC8 Journal
Abstract
Chem. investigation of the leaves of Tephrosia apollinea has yielded a new flavanone named (+)-apollineanin, together with 2 known
flavones: (-)-semiglabrin and (-)-semiglabrinol. The structure of the new compd. was detd. on the basis of mass, 1D and 2D NMR
spectroscopies including NOE difference spectroscopy. The abs. stereochem. of (+)-apollineanin was detd. by Mosher ester methodol.
and from CD data.
flavanone
Answer 321:
First synthesis of (±)-monotesone B and new syntheses of (±)-lonchocarpol A and (±)-bavachin. Kenez, Agnes; Antus,
Sandor. Department of Organic Chemistry, University of Debrecen, Debrecen, Hung. Natural Product Communications (2006),
1(1), 51-55. Publisher: Natural Product Communications, CODEN: NPCACO ISSN: 1555-9475. Journal written in English. CAN
Abstract
The first synthesis of (±)-monotesone B and new syntheses of (±)-lonchocarpol A and (±)-bavachin were achieved starting from the
corresponding methoxymethyl-protected C-prenylated acetophenone derivs. Their antifungal activity was tested against Candida
albicans.
Answer 322:
Inhibition of matrix metalloproteinase-2 secretion by chalcones from the twigs of Dorstenia barteri Bureau. Ngameni,
Bathelemy; Touaibia, Mohamed; Belkaid, Anissa; Ambassa, Pantaleon; Watchueng, Jean; Patnam, Ramesh; Ngadjui, Bonaventure T.;
Annabi, Borhane; Roy, Rene. Department of Chemistry, Universite du Quebec a Montreal, Montreal, QC, Can. ARKIVOC
(Gainesville, FL, United States) (2007), (9), 91-103. Publisher: Arkat USA Inc., CODEN: AGFUAR
http://www.arkat-usa.org/ARKIVOC/JOURNAL_CONTENT/manuscripts/2007/BA-2092LP%20as%20published%20mainmanuscript.pdf
Journal; Online Computer File written in English. CAN 146:74866 AN 2006:1345336 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
Chalcones and their analogs were extd. from the twigs of Dorstenia barteri and investigated for their capacity to inhibit matrix
metalloproteinase (MMP)-2 secretion from brain tumor-derived U87 glioblastoma cells. Among all tested compds., potent inhibitory
activities were recorded for chalcones 1, 4, 5, and 6 and to a lesser extent for 2 and 3. Semi-synthetic derivs. 7-9 displayed low
(<30%) MMP-2 secretion inhibitory activity at concns. ranging from 0.025 to 250 μM. Chalcones 1, 4, 5, and 6 were found to be more
active in comparison to the documented MMP secretion inhibitors chlorogenic acid (CHL) and epigallocatechin-3-gallate (EGCg).
Hydrogenation of 1 and acid-catalyzed cyclization of 3 were performed, thus generating three semi-synthetic derivs. (7-9). The newly
synthesized flavanone 7 (cycloglabrol) and its chalcone analog 8 (isocycloglabrol) exhibited low MMP-2 secretion inhibitory activity with
30% inhibition at 250 μM. The activity of Dorstenia barteri crude exts. could be attributable to the high concn. of prenylated chalcones
and more specifically to stipulin 5. Altogether, the structure-activity relationships established indicated that the hydroxyl, 2,3-double
bond, the prenyl group, and its positioning could account for their role in inhibiting MMP-2 secretion, a process involved in extracellular
matrix degrdn. and brain tumor progression.
Answer 323:
Structural characterization for flavonoids through MEDV and xanthine-oxidase inhibition activity prediction by QSAR.
Zhang, Meng-Jun; Wu, Shi-Rong; Liao, Chun-Yang; Li, Zhi-Liang. Dep. Analytical Chem., Fac. Clinical Lab. Sci., The Third Miliary
Medical Univ., Chongqing, Peop. Rep. China. Jiefangjun Yaoxue Xuebao (2006), 22(5), 328-332. Publisher: Zhongguo Renmin
Jiefangjun Zonghouqinbu Weishengbu Yaopin Yiqi Jianyansuo, CODEN: JYXIAY ISSN: 1008-9926. Journal written in Chinese.
flavanone
Abstract
The aim of this paper is to predict xanthine-oxidase inhibition activity of flavonoids. A novel set of structural descriptors with ten
elements, called the mol. electronegativity-distance vector(MEDV), was developed according to classification of four connection
formula for various local carbon and pseudo-carbon atoms in the mols. under examn. The MEDV-d vector was then used to describe
the chem. structures of 21 flavonoids by a multiple linear regression(MLR). The performance of the six-parameter model was tested
through cross-validation by the leave-one-out procedure(LOO). A reasonable mol. modeling result was achieved with a very high
correlation coeff. (r=0.925) and a satisfactory result of cross-validation was obtained with a fairly resemble correlation coeff. (r=0.843).
The model based on the MEDV descriptors showed good estimative stability and predictive ability, and could be used for designing and
developing efficient inhibitors of xanthine-oxidase.
Answer 324:
Effect of Heat Treatment on the Phenolic Compounds and Antioxidant Capacity of Citrus Peel Extract. Xu, Guihua; Ye,
Xingqian; Chen, Jianchu; Liu, Donghong. Department of Food Science and Nutrition, Zhejiang University, Hangzhou, Peop. Rep.
China. Journal of Agricultural and Food Chemistry (2007), 55(2), 330-335. Publisher: American Chemical Society, CODEN:
JAFCAU ISSN: 0021-8561. Journal written in English. CAN 146:80740 AN 2006:1328958 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
This paper reports the effects of heat treatment on huyou (Citrus paradisi Changshanhuyou) peel in terms of phenolic compds. and
antioxidant capacity. High-performance liq. chromatog. (HPLC) coupled with a photodiode array (PDA) detector was used in this study
for the anal. of phenolic acids (divided into 4 fractions: free, ester, glycoside, and ester-bound) and flavanone glycosides (FGs) in
huyou peel (HP) before and after heat treatment. The results showed that after heat treatment, the free fraction of phenolic acids
increased, whereas ester, glycoside, and ester-bound fractions decreased and the content of total FGs declined (P < 0.05).
Furthermore, the antioxidant activity of methanol ext. of HP increased (P < 0.05), which was evaluated by total phenolics contents
(TPC) assay, 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) (ABTS.bul.+) method, and ferric reducing antioxidant power (FRAP)
assay. The correlation coeffs. among TPC, ABTS, FRAP assay, and total cinnamics and benzoics (TCB) in the free fraction were
significantly high (P < 0.05), which meant that the increase of total antioxidant capacity (TAC) of HP ext. was due at least in part to the
increase of TCB in free fraction. In addn., FGs may be destroyed when heated at higher temp. for a long time (for example, 120 °C
for 90 min or 150 °C for 30 min). Therefore, it is suggested that a proper and reasonable heat treatment could be used to enhance the
antioxidant capacity of citrus peel.
Answer 325:
Synthesis of some nitro-substituted flavanones, pyrazolines, and their derivatives. Parmar, P. J.; Rajput, S. I.; Doshi, A. G.
Department of Chemistry, B.P. Arts, S.M.A. Science and K.K.C. Commerce College, Chalisgaon, India. Asian Journal of
Chemistry (2007), 19(1), 493-498. Publisher: Asian Journal of Chemistry, CODEN: AJCHEW ISSN: 0970-7077. Journal written in
Abstract
2-Hydroxy-3-nitro-5-methylacetophenone condenses with 3,4-substituted benzaldehydes in EtOH in presence of aq. NaOH to give
chalcones. Subsequent heating under reflux with 80% ethanol and concd. H2SO4 gave flavanones I (R = H, R1 = NO2; RR1 =
OCH2O; R = R1 = H; R = OMe, R1 = H), while reaction with N2H4.H2O in EtOH led to the resp. pyrazolines II. The latter are also
flavanone
obtained by treatment of I with N2H4.H2O, piperidine, and EtOH under reflux. Pyrazolines II reacted with AcOH to form
1-acetylpyrazolines. Pyrazolines II or the 1-acetyl derivs. reacted with Ac2O and a pinch of anhyd. NaOAc to give
1-acetyl-2-acetoxypyrazolines. Condensation of II with BzCl in pyridine yields 1-benzoylpyrazolines. The structures of all compds.
were established on the basis of spectral data (UV, IR, NMR), elemental anal., and chem. properties.
R1
R
NO 2
Me I
O
R1
OH N NH
O2 N R
Me II
Answer 326:
Flavonoids as antagonists at A1 adenosine receptors. Alexander, Stephen P. H. Institute of Neuroscience and School of
Biomedical Sciences, University of Nottingham Medical School, Nottingham, UK. Phytotherapy Research (2006), 20(11),
1009-1012. Publisher: John Wiley & Sons Ltd., CODEN: PHYREH ISSN: 0951-418X. Journal written in English. CAN 146:198589
Abstract
This study aimed to investigate the potential for flavonoid action at A1 adenosine receptors in vitro. In a radioligand binding assay for
A1 adenosine receptor occupancy in particulate prepns. from guinea-pig cerebral cortex, flavonoids competed in concn.-dependent
manners with Hill slopes typically not different from unity. Of the flavonoids tested, quercetin showed highest affinity (pKi value of
5.33). At a concn. of 28 μM, quercetin evoked a rightward shift in the N6-cyclopentyladenosine-induced inhibition of elec. evoked
contractions of the guinea-pig isolated ileum, allowing the calcn. of a pKi value of 4.71. These data suggest, therefore, that flavonoids
represent an addnl. dietary source of A1 adenosine receptor antagonists (beyond the methylxanthines, caffeine and theophylline).
Answer 327:
flavanone
Hesperidin and bone metabolism. Uehara, Mariko. Faculty of Applied Bio-Science, Department of Nutritional Science, Tokyo
University of Agriculture, Japan. Clinical Calcium (2006), 16(10), 1669-1676. Publisher: Iyaku Janarusha, CODEN: CLCCEJ
ISSN: 0917-5857. Journal written in Japanese. CAN 146:378942 AN 2006:1307537 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
Among the naturally occurring citrus flavonoids, hesperidin, a flavanone glycoside, may be assocd. with potential benefits in the
prevention of diseases, such as decreasing capillary permeability, anti inflammatory, antimicrobial and anti carcinogenic effects.
Hesperidin also regulates hepatic cholesterol synthesis by inhibiting the activity of 3-hydroxy-3-methylglutaryl CoA (HMG-CoA)
reductase. Recently, Mundy et al. reported that statins, cholesterol lowering agents, induce bone formation and inhibit bone resorption
both in vitro and in vivo. Thus, considerable attention has focused on the relationship between the inhibitory activity on HMG-CoA
reductase and bone action. We examd. the effects of hesperidin on bone metab. in ovariectomized mice, orhiectomized mice and
magnesium deficient rats, animal models of osteoporosis. Hesperidin inhibited bone loss the animals with lowering serum and hepatic
cholesterol. These results suggest hesperidin may act on bone by the same mechanism as that of statins. Further studies are
needed to define hesperidin's mechanisms of action on bone.
Answer 328:
Synthesis, biological evaluation and in silico metabolic and toxicity prediction of some flavanone derivatives. Moorthy,
Narayana Subbiah Hari Narayana; Singh, Rahul Jitendra; Singh, Hemendra Pratap; Gupta, Sayan Dutta. School of Pharmaceutical
Sciences, Rajiv Gandhi Proudyogiki Vishwavidyalaya, Bhopal, India. Chemical & Pharmaceutical Bulletin (2006), 54(10),
1384-1390. Publisher: Pharmaceutical Society of Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN
Abstract
Flavones chem. are anthoxanthins, occur either in the free state or as glycosides assocd. with tannins (Flavanoids). Flavanoids
(derivs. of flavone) possess various pharmacol. activities and due to its xanthine-oxidase enzyme inhibitory effect it also has
superoxide-scavenging activities. A series of 2-phenyl-2,3-dihydrochromon-4-one derivs. (flavanone derivs.) were synthesized from
chalcones by cyclization method and their activities were evaluated against some gram pos. and gram-neg. bacteria. IR, NMR and
CHN anal. confirmed the structure of the synthesized compds. The results of the antibacterial studies shows that compds. 2b, 2e, 2f
and 2h possess activity against many bacterial strains. Among that the compd. (2h) has remarkable activity against all strains viz. 25
μg/mL inhibitory concn. against S. aureus, S. sonnei, E. coli, S. typhimurium and V. cholerae. Compd. 2f possess min. inhibitory
concn. of 200 μg/mL against E. coli and S. typhimurium and 25 μg/mL against S. sonnei, S. dysenteriae and V. cholerae. In silico
metabolic and toxicity study of the synthesized compds. were performed and the predicted result showed that the compd. having
hydroxyl functional group undergo sulfate and O-glucuronide conjugation reaction and methoxy derivs. undergo demethylation reaction.
The biol. active compds. are free of toxicity in oncogene, teratogen, sensitivity and immunotoxicity.
Answer 329:
Exotic flora dependence of an unusual Brazilian propolis: The pinocembrin biomarker by capillary techniques. Adelmann,
Juliana; Passos, Mauricio; Breyer, Daniel Henrique; Rocha dos Santos, Maria Helena; Lenz, Cesar; Leite, Natalicio Ferreira; Lancas,
Fernando Mauro; Fontana, Jose Domingos. Biomass Chemo/Biotechnology Laboratory (LQBB), Department of Pharmacy, R.
Lothario Meissner, Federal University of Parana (UFPR), Subsede Botanico, Curitiba PR, Brazil. Journal of Pharmaceutical and
Biomedical Analysis (2007), 43(1), 174-178. Publisher: Elsevier B.V., CODEN: JPBADA ISSN: 0731-7085. Journal written in
flavanone
Abstract
Significant amts. of pinocembrin (>10%), a dihydroxy-flavanone, was found in the compn. of an unusual brand of a subtropical
Brazilian propolis. Incidentally, this sealing material was obtained from hives surrounding a large forestry site based on a single exotic
flora, namely poplar (Populus sp.). Examn. of the different botanical parts of poplar revealed the buds as the main source of the
flavanone. Techniques used for the establishment of the chem. correlation between the propolis brand and the poplar buds were
TLC/densitometry, capillary GC-MS in the e.i. mode, and capillary zone electrophoresis with DAD monitoring. Since color enhancement
after Al3+ complexation applies just for more hydroxylated flavonoids, the alternative techniques herein applied were of value for
pinocembrin detection and estn. Anal. data indicated the dominance of the main phenolic pinocembrin biomarker as well as the
presence of other related flavonoids in the botanical source and in the propolis derived thereof.
Answer 330:
Prevention and treatment of aging and age-related disorders. Omoigui, Osemwota Sota. (USA). U.S. Pat. Appl. Publ.
(2006), 60pp., Cont.-in-part of U.S. Ser. No. 268,609. CODEN: USXXCO US 2006275294 A1 20061207 Patent written in
English. Application: US 2006-279239 20060410. Priority: US 2002-224743 20020822; US 2004-961037 20041012; US
2005-58371 20050216; US 2005-122030 20050505; US 2005-268609 20051108. CAN 146:20347 AN 2006:1286190 CAPLUS

US 20060275294 A1 20061207 US 2006-279239 20060410
US 20040038874 A1 20040226 US 2002-224743 20020822
US 20060078531 A1 20060413 US 2004-961037 20041012
US 20050152905 A1 20050714 US 2005-58371 20050216
US 20060078532 A1 20060413 US 2005-122030 20050505
US 20060078533 A1 20060413 US 2005-268609 20051108
US 2002-224743 B2 20020822
US 2004-961037 A2 20041012
US 2005-58371 A2 20050216
US 2005-122030 A2 20050505
US 2005-268609 A2 20051108
Abstract
The invention relates to a method for prevention and treatment of aging, age-related disorders and/or age-related manifestations
including atherosclerosis, peripheral vascular disease, coronary artery disease, osteoporosis, type 2 diabetes, dementia, and some
forms of arthritis and cancer in a subject comprising administration sep., sequentially, or simultaneously of a therapeutically effective
dosage of each component or combination of statins, bisphosphonates, cholesterol-lowering agents, or biol. or biochem. inhibitors
targeting the interleukin-6 signaling pathway. Inhibition of the signal transduction pathway for interleukin 6-mediated inflammation is
key to the prevention and treatment of atherosclerosis, peripheral vascular disease, coronary artery disease, aging, age-related
disorders and/or age-related manifestations including osteoporosis, type 2 diabetes, dementia and some forms of arthritis and tumors.
flavanone
Said method for prevention and treatment of said disorders is based on inhibition of interleukin-6 inflammation through regulation of
cholesterol metab., isoprenoid depletion and/or inhibition of the signal transduction pathway.
Answer 331:
Antiallergic action of mandarin orange. Kobayashi, Shoko; Takayanagi, Masayoshi; Tanabe, Shoichi. Dep. of Health and
Welfare, Takasaki Univ. of Health and Welfare, Japan. New Food Industry (2006), 48(11), 15-22. Publisher: Shokuhin Shizai
Kenkyukai, CODEN: NYFIAM ISSN: 0547-0277. Journal; General Review written in Japanese. CAN 147:94707 AN
Abstract
A review. Topics discussed are development mechanism of pollen allergy and antiallergic effect of mandarin orange, effect of
mandarin orange powder on histamine release inhibition in pollen allergic patients, effect of mandarin orange powder on inhibition of
RBL-2H3 cell degranulation, mechanism of flavanone in mandarin orange on inhibition of cell degranulation and inhibitory components
in mandarin orange.
Answer 332:
Cosmetic method for treating gynoid lipodystrophy. Okigami, Henry; Guerra Filho, Samuel dos Santos; Lacerda, Jorge Renato
Guimaraes. (Brazil). Braz. Pedido PI (2005), 23pp. CODEN: BPXXDX BR 2003003724 A 20050412 Patent written in
Portuguese. Application: BR 2003-3724 20030821. Priority: . CAN 145:495713 AN 2006:1266854 CAPLUS (Copyright (C)

BR 2003003724 A 20050412 BR 2003-3724 20030821
BR 2003-3724 20030821
Abstract
Cellulite in women can be treated with a compn. contg. an aromatase inhibitor and an estrogen receptor blocker encapsulated in
nanocapsules, liposomes, or in cyclodextrin.
Answer 333:
Dehydrogenation of flavanones, 1H-3-(2-hydroxy-3-nitro-5-methylphenyl)-5-(substituted phenyl)-2-pyrazolines and their

derivatives. Parmar, P. J.; Rajput, S. I. Department of Chemistry, B. P. Arts, S.M.A. Science and K.K.C. Commerce College,
flavanone
Chalisgaon, India. International Journal of Chemical Sciences (2006), 4(3), 629-634. Publisher: Sadguru Publications, CODEN:
IJCSIL ISSN: 0972-768X. Journal written in English. CAN 147:406736 AN 2006:1255634 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Pyrazolines or flavanones were treated with I in DMSO to give 1H-3-(2-hydroxy-3-nitro-5-methylphenyl)-5-arylpyrazoles or

6-methyl-8-nitroflavones.
Answer 334:
Microwave enhanced palladium catalyzed coupling reactions: A diversity-oriented synthesis approach to functionalized
flavones. Fitzmaurice, Richard J.; Etheridge, Zac C.; Jumel, Emelie; Woolfson, Derek N.; Caddick, Stephen. Department of
Chemistry, Christopher Ingold Laboratories, University College London, London, UK. Chemical Communications (Cambridge,
United Kingdom) (2006), (46), 4814-4816. Publisher: Royal Society of Chemistry, CODEN: CHCOFS ISSN: 1359-7345. Journal
Abstract
Microwave enhanced diversity-oriented synthesis (MEDOS) using palladium catalyzed protocols was introduced as a powerful new
strategy for the synthesis of systematically modified small mols. and was highlighted by application to functionalized flavones. E.g.,
brominated flavone I (R = Br) was reacted with phenylboronic acid using POPd and CsF in THF at 85° under microwave irradn. to give
the corresponding arylation product I (R = Ph) with 98% yield.
R I
Answer 335:
A flavanone and other constituents of the Brazilian endemic species Trembleya laniflora (D. Don) Cogn. (Melastomataceae).
Ventura, Claiton Pires; Dias de Souza Filho, Jose; Braga de Oliveira, Alaide; Braga, Fernao Castro. Faculdade de Farmacia,
Universidade Federal de Minas Gerais, Belo Horizonte, Pampulha, Brazil. Biochemical Systematics and Ecology (2006), Volume
Date 2007, 35(1), 40-41. Publisher: Elsevier Ltd., CODEN: BSECBU ISSN: 0305-1978. Journal written in English. CAN
Abstract
A chemotaxonomic study carried out for the leaves of Trembleya laniflora (D. Don) Cogn. (Melastomataceae) resulted in the
flavanone
identification of 5-hydroxy-7,4'-dimethoxyflavone, along with mixts. of α-amirin (major constituent), β-amirin and lupeol; β-sitosterol
(84%) and stigmasterol (16%). The isolated compds. were evaluated in the antimicrobial agar diffusion assay and none of them
inhibited the growth of Staphylococcus aureus and Micrococcus luteus in the concn. of 50 μg/disk.
Answer 336:
Dietary flavonoids attenuate tumor necrosis factor α-induced adhesion molecule expression in human aortic endothelial
cells. Structure-function relationships and activity after first pass metabolism. Lotito, Silvina B.; Frei, Balz. Linus Pauling
Institute, Oregon State University, Corvallis, OR, USA. Journal of Biological Chemistry (2006), 281(48), 37102-37110.
Publisher: American Society for Biochemistry and Molecular Biology, CODEN: JBCHA3 ISSN: 0021-9258. Journal written in English.
Abstract
Flavonoids can be beneficial for human health via antioxidant and anti-inflammatory mechanisms. We investigated whether and by
what mechanisms dietary flavonoids inhibit expression of cellular adhesion mols., which is relevant to inflammation and
atherosclerosis. The capacity of flavonoids to inhibit tumor necrosis factor α-induced adhesion mol. expression in human aortic
endothelial cells in vitro was dependent on specific structural features of the flavonoids. The 5,7-dihydroxyl substitution of a flavonoid
A ring and 2,3-double bond and 4-keto group of the C ring were the main structural requirements for inhibition of adhesion mol.
expression. Hydroxyl substitutions of the B and C rings but not the A ring, were essential for antioxidant activities. Thus, only
hydroxyl flavones, such as apigenin and chrysin, and flavonols, such as galangin, kaempferol and quercetin, were able to inhibit
endothelial adhesion mol. expression, whereas flavone, chromone, the flavanone naringenin, and the flavanol (-)-epicatechin, were not
effective. At low concns., the active flavonoids attenuated the expression of E-selectin and intercellular adhesion mol. 1 (ICAM-1), but
not vascular cell adhesion mol. 1 (VCAM-1). Exposure of cultured hepatocytes to apigenin and kaempferol mimicked the first pass
metab. and greatly diminished the inhibitory effect of flavonoids on endothelial ICAM-1 expression. Thus, the effects of dietary
flavonoids on endothelial adhesion mol. expression depend on their mol. structure, concn., and metabolic transformation, but not their
antioxidant activity.
Answer 337:
Novel flavanoids as chemotherapeutic, chemopreventive, and antiangiogenic agents. Zaveri, Nurulain; Waleh, Nahid. (Sri
International, USA). U.S. Pat. Appl. Publ. (2006), 37pp., Cont.-in-part of U.S. Ser. No. 418,736. CODEN: USXXCO US
2006264500 A1 20061123 Patent written in English. Application: US 2006-404230 20060414. Priority: US 2002-126407

US 20060264500 A1 20061123 US 2006-404230 20060414
US 20030229136 A1 20031211 US 2002-126407 20020418
US 20040029914 A1 20040212 US 2003-418736 20030418
US 7329687 B2 20080212
US 2002-126407 A2 20020418
flavanone
US 2003-418736 A2 20030418
Abstract
Flavanoids, flavanones and flavanols, such as I [R1, R2, R3 = H, OH, sulfhydryl, halogen alkoxy, etc.; R5 = O, S, :NH, OH, SH,
NH2, acyloxy, etc.; R6, R7, R8, R9 = H, OH, alkoxy, etc. or neighboring groups may form fused carbocyclic rings, such as R6R7 =
-CH:CHCH:CH- or R7R8 = -(CH2)4-; X = O, S, NH, CH2; bonds a and b may be double or single as appropriate for substituents], and
related chalcones were prepd. for use in pharmaceutical compns. as chemotherapeutic, chemopreventive, and antiangiogenic agents.
These flavanoids and chalcones were claimed for therapeutic use in the treatment of cancer of the brain, breast, ovary, prostate, lung,
kidney or colon. Thus, flavanol II was prepd. via a cyclocondensation reaction of 1-hydroxy-2-acetonaphthone with
3,4,5-trimethoxybenzaldehyde using piperidine and pyridine in EtOH to form the corresponding flavanone and subsequent redn. of the
resulting flavanone using NaBH4 in THF/EtOH. Pharmaceutical compns. were provided, as well as, methods of synthesis and use.
R1 OMe
R2 OMe
R9
R8 X O
R3 OMe
a
R7
b
R6 R5 I OH II
Answer 338:
Navigating the network of floral scent production. Zvi, M. Moyal Ben; Spitzer, B.; Vainstein, A. The Institute of Plant
Sciences and Genetics in Agriculture, Faculty of Agricultural, Food and Environmental Quality Sciences, The Hebrew University of
Jerusalem, Rehovot, Israel. Acta Horticulturae (2006), 714(Proceedings of the XXIInd International Eucarpia Symposium, Section
Ornamentals, 2006), 143-154. Publisher: International Society for Horticultural Science, CODEN: AHORA2 ISSN: 0567-7572.
Abstract
Flower fragrance is a composite character detd. by secondary metabolites of diverse biosynthetic origin. Together with other traits,
such as flower color, it is used by plants to lure pollinators and seed dispersers, thus ensuring plant survival. Research into the
regulatory mechanisms leading to floral scent prodn./emission is still in its infancy and even less is known regarding flow within and
crosstalk between secondary metabolic pathways leading to floral scent prodn. Using transgenic plants modified in anthocyanin
prodn., we revealed an intriguing interrelationship between the branches of the phenylpropanoid pathway leading to the prodn. of
anthocyanins and volatiles. Specifically, we recorded five- to seven-fold higher levels of the volatile phenylpropanoids Me benzoate
and 2-hydroxy-Me benzoate in flavanone 3-hydroxylase (F3h)-suppressed carnation flowers with dramatically reduced anthocyanin
levels, as compared to control non-transgenic flowers. Furthermore, over-expression in petunia flowers of the transcriptional regulator
Pap1 (prodn. of anthocyanin pigment 1), which activates the phenylpropanoid pathway, led to increases in both anthocyanin
accumulation and volatile phenylpropanoid emission. Using virus-induced gene silencing (VIGS) for large-scale identification of floral
scent genes, we further characterized metabolic flow within the pathway. The advantages of VIGS and of petunia as a model plant
create a solid infrastructure for the future isolation of regulatory factors involved in floral scent prodn./emission. Knowledge gained
flavanone
from an understanding of mechanisms leading to floral scent prodn./emission should provide us with better insight into nature's way of
ensuring evolutionary success, as well as with advanced tools for the metabolic engineering of fragrance.
Answer 339:
Antihyperglycemic Activity and Chemical Constituents of Eysenhardtia platycarpa. Narvaez-Mastache, Jose M.;
Garduno-Ramirez, Maria Luisa; Alvarez, Laura; Delgado, Guillermo. Instituto de Quimica, Universidad Nacional Autonoma de Mexico,
Coyoacan, Mex. Journal of Natural Products (2006), 69(12), 1687-1691. Publisher: American Chemical Society-American Society
of Pharmacognosy, CODEN: JNPRDF ISSN: 0163-3864. Journal written in English. CAN 146:118105 AN 2006:1212282
Abstract
The methanolic exts. from branches (BEP) and leaves (LEP) of Eysenhardtia platycarpa significantly decreased the blood glucose
levels in normal and streptozotocin (STZ)-induced diabetic rats. One new flavone,
(1''R)-5,4',1''-trihydroxy-6,7-(3'',3''-dimethylchroman)flavone (1), together with the known compds.
5,7-dihydroxy-6-methyl-8-prenylflavanone (3), 5,7-dihydroxy-8-methyl-6-prenylflavanone (4), 5,7-dihydroxy-6-prenylflavanone (5),
5,7-dihydroxy-8-prenylflavanone (6), 3-O-acetyloleanolic acid (7), oleanolic acid, 3β-acetoxy-11α,12α-epoxy-oleanan-28,13β-olide,
lupeol, betulinic acid, β-sitosterol, β-sitosteryl β-D-glucopyranoside, β-sitosteryl palmitate, and 3-O-methyl-myo-inositol were isolated
from BEP. Addnl., one new flavanone, (2S)-4'-O-methyl-6-methyl-8-prenylnaringenin (2), as well as the known compds.
3,4,6,4'-O-methyl-8-prenylnaringenin (8), and 5-hydroxy-7-methoxy-8-prenylflavanone (9) were isolated from LEP. 3-O-Acetyloleanolic
acid (7), identified as the major constituent of BEP, showed a significant decrease (31 mg/kg of body wt., P < 0.05) in the glucose
level of STZ-induced diabetic rats. The obtained results correlate with the traditional use of this species.
Answer 340:
The total flavanones of peanut hulls extraction and the identification by ultrasonic wave. Yang, Wen-hui; Li, Wei-bin; Huang,
Suo-yi; Li, Rong. Youjiang Med. College for Nationalities, Baise, Guangxi, Peop. Rep. China. Weiliang Yuansu Yu Jiankang
Yanjiu (2006), 23(5), 28-30. Publisher: Weiliang Yuansu Yu Jiankang Yanjiu Zazhishe, CODEN: WYYJAF ISSN: 1005-5320.
Abstract
In order to make use of the resources of peanut hulls, avoid wasting and approach the extn. of total flavanone of peanut hulls. The
flavonids were extd. by ethanol as the solvent from peanut hulls with ultrasonic wave and ethanol extn. Using spectrophotometry to
ext. and check the flavanone of peanut hulls. By this method getting the d. of the total flavanone of peanut hulls is C = 0.5937mg/mL
and the rate of recovery is 101.1 %. This text provides the extn. and purifying methods to get the outcome and the purity of the
flavanone are all very high. This method is a purely phys. process and has not any pollution. It is an ideal way to ext. the flavanone
of peanut hulls.
Answer 341:
Isolation and characterization of antioxidant components from oregano (Origanum heracleoticum). Tsimogiannis, Dimitrios;
Stavrakaki, Maria; Oreopoulou, Vassiliki. School of Chemical Engineering, National Technical University of Athens, Athens,
flavanone
Greece. International Journal of Food Science and Technology (2006), 41(Suppl. 1), 39-48. Publisher: Blackwell Publishing Ltd.,
CODEN: IJFTEZ ISSN: 0950-5423. Journal written in English. CAN 146:141367 AN 2006:1159345 CAPLUS (Copyright (C)
Abstract
In this study, Origanum heracleoticum was examd. as potential source of phenolic antioxidants. The components of the plant were
extd. in a Soxhlet app. sequentially with solvents of increasing polarity, specifically with petroleum ether (P), di-Et ether (D) and
ethanol (E); the ethanol ext. was further fractionated to obtain a di-Et ether (ED) and an Et acetate (EEAc) fraction. The activity of the
exts. to scavenge 2'2'-diphenyl-1-picrylhydrazyl followed the order ED > E> D > EEAc > > P. Moreover, the antioxidant activity in
refined cottonseed oil at a concn. of 500 ppm was monitored through peroxide value measurements and revealed that ED resulted in
the highest decrease in the rate of peroxide formation followed by D. Specific flavonoids and rosmarinic acid were detected as the
main components of D, ED through HPLC-DAD and HPLC-MS/MS analyses.
Answer 342:
Polysaccharide formulation from Juglans mandshurica for treating cerebral cancer. Miao, Zhiqi; Yu, Xiangli; Wang, Yechun;
Miao, Haibin; Tang, Kexuan. (Shanghai Jiao Tong University, Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu
(2006), 11pp. CODEN: CNXXEV CN 1850102 A 20061025 Patent written in Chinese. Application: CN 1002-4276 20060302.

CN 1850102 A 20061025 CN 2006-10024276 20060302
CN 2006-10024276 20060302
Abstract
The invention pertains to a polysaccharide formulation purified from Juglans mandshurica for treating cerebral cancer, which comprises
Juglans mandshurica polysaccharide 85-98% and flavonoids e.g. flavone, flavonol, flavanone, flavanol 15-2%. The formulation
0.1-200g is dissolved in water or 0.1-20% ethanol soln. for oral administration. Method for extg. antitumor ingredients comprises
pulvering, extg. with water twice, filtering, concg. the supernatant, extg. with chloroform, pptg. the aq. phase with ethanol, drying and
pulverizing to obtain Juglans mandshurica polysaccharide powder for use.
Answer 343:
Acetylated Flavanone Glycosides from the Rhizomes of Cyclosorus acuminatus. Fang, Wei; Ruan, Jinlan; Wang, Zhong;
Zhao, Zhongxiang; Zou, Jian; Zhou, Daonian; Cai, Yaling. College of Pharmacy, Tongji Medical Center, Huazhong University of
Science and Technology, Wuhan, Peop. Rep. China. Journal of Natural Products (2006), 69(11), 1641-1644. Publisher: American
Chemical Society-American Society of Pharmacognosy, CODEN: JNPRDF ISSN: 0163-3864. Journal written in English. CAN
flavanone
Abstract
Six new flavanone glycosides (1-6) were isolated from the methanol ext. of the rhizomes of C. acuminatus, together with the parent
flavanone glycoside. Their structures were established on the basis of spectroscopic and chem. methods. All compds. showed
moderate activity against Streptococcus pneumoniae and Haemophilus influenzae.
Answer 344:
Determination of diastereomerization barrier of some flavanones by high-performance liquid chromatography methods.

Asztemborska, Monika; Zukowski, Janusz. Institute of Physical Chemistry, Polish Academy of Sciences, Warsaw, Pol. Journal
of Chromatography, A (2006), 1134(1-2), 95-100. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in
Abstract
The rate consts. and activation energy barriers ΔG.thermod. of diastereomerization reaction of flavanones: naringin, narirutin,
hesperidin and neohesperidin were detd. The stopped-flow HPLC (SFM-HPLC), dynamic HPLC (D-HPLC) and enantioselective HPLC
combined with the classical kinetic method were applied for detn. of these parameters. It was found that the rate consts. of
diastereomerization were about eight times higher for naringin and narirutin (1.9 × 10-5 s-1) than for hesperidin and neohesperidin (2.4 ×
10-6 s-1). No significant differences in the rate of diastereomerization were found between neohesperidosides and corresponding
rutinosides.
Answer 345:
Flavanone metabolism in healthy and tumor-bearing rats. Silberberg, M.; Gil-Izquierdo, A.; Combaret, L.; Remesy, C.; Scalbert,
A.; Morand, C. Unite des Maladies Metaboliques et Micronutriments, Inra, Centre de Recherche de Clermont-Ferrant/Theix,
Saint-Gene` s-Champanelle, Fr. Biomedicine & Pharmacotherapy (2006), 60(9), 529-535. Publisher: Elsevier SAS, CODEN:
BIPHEX ISSN: 0753-3322. Journal written in English. CAN 147:202969 AN 2006:1138113 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Flavanones, the main polyphenols of citrus fruits, are thought to contribute to the protective effects of these fruits against
cardiovascular diseases and cancer. The metab. of naringin (naringenin 7-O-neohesperidoside) is studied here in healthy
(sham-operated, ShO) and tumor-bearing (TuB) rats. The tumor was induced by implanting Yoshida's sarcoma in hindlimb. Both groups
received for 7 days a semi-synthetic diet contg. 0.5% naringin in per feeding conditions. Flavanones were analyzed in plasma, liver,
kidney and urine by tandem mass spectrometry. Naringenin conjugates (essentially glucuronides) accounted for up to 98% of the total
flavanones in plasma. Low amts. of hesperetin (4'-O-Me naringenine) and isosakuranetin (3'-hydroxy-4'-O-methylnaringenin) were also
detected in all biol. samples and accounted for 2% of the total flavanones in plasma. They were largely present as aglycons. The in
vivo hydroxylation of flavanones is described here for the first time. Total concns. of naringenin metabolites reached 17.3 ± 2.7 μM in
plasma 6 h after the beginning of the meal in healthy rats and only 10.6 ± 1.3 μM in TuB rats. The nature of metabolites was similar in
both healthy and TuB rats and in plasma, tissues and urine. The lower concn. of flavanones in the TuB rats suggests that disease and
more particularly cancer, may affect the bioavailability of flavonoids.
Answer 346:
flavanone
Extraction method and its application of (2S)-5,7,2',6'-tetrahydroxy-6,8-di(γ, γ-dimethylallyl)-flavanone. Fan, Guorong; Peng,
Jinyong; Chai, Yifeng; Wu, Yutian. (Second Military Medical University, Peop. Rep. China). Faming Zhuanli Shenqing Gongkai
Shuomingshu (2006), 11pp. CODEN: CNXXEV CN 1850816 A 20061025 Patent written in Chinese. Application: CN
1002-6825 20060524. Priority: . CAN 145:500049 AN 2006:1136719 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))

CN 1850816 A 20061025 CN 2006-10026825 20060524
CN 2006-10026825 20060524
Abstract
The title method comprises extg. Patrinia villosa with ethanol to obtain crude ext., grade-extg. the crude ext. with org. solvent, and
purifying with silica gel column chromatog. to obtain the final product. The obtained product has high purity over 99%, and can be
prepd. in large scale. The product has antitumor activity, and can be applied to prepn. of antitumor agents.
Answer 347:
Composition for prevention and treatment of cancer comprising 2',4',5,7-tetrahydroxy-5',6-diprenylflavanone compound for
preventing propagation of tumor cells by inhibiting casein kinase 2(ckii). Bae, Young Seuk; Kim, Soon Hee; Lee, Byong
Won; Park, Ki Hun. (Industry-Academic Coorperation Foundation Daegu Haany University, S. Korea). Repub. Korean Kongkae
Taeho Kongbo (2006), No pp. given. CODEN: KRXXA7 KR 2006055083 A 20060523 Patent written in Korean. Application: KR

KR 2006055083 A 20060523 KR 2004-94403 20041118
KR 2007083237 A 20070823 KR 2007-81393 20070813
KR 773133 B1 20071102
KR 2004-94403 A3 20041118
Abstract
A compn. for the prevention and treatment of cancer comprising a 2',4',5,7-tetrahydroxy-5',6-diprenylflavanone compd. is provided to
inhibit casein kinase 2, thereby being able to inhibit propagation of tumor cells. The compn. for the prevention and treatment of cancer
flavanone
comprises a 2',4',5,7-tetrahydroxy-5',6-diprenylflavanone or a pharmaceutically acceptable salt thereof, wherein the flavanone is extd.
from the roots of Cudrania tricuspidata with a polar solvent including hexane, chloroform or Et acetate.
Answer 348:
Inhibitory agent for estrone-3-sulfate transporter activity. Tamai, Ikumi; Yabuuchi, Hikaru. (Genomembrane Co., Ltd., Japan).
PCT Int. Appl. (2006), 30pp. CODEN: PIXXD2 WO 2006112330 A1 20061026 Designated States W: AE, AG, AL, AM, AT, AU,
AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM,
HR, HU, ID, IL, IN, IS, KE, KG, KM, KN, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG,
NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN,
YU, ZA, ZM. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ,
CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in Japanese. Application: WO 2006-JP307751 20060412. Priority:
JP 2005-119098 20050415. CAN 145:449189 AN 2006:1123248 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))

WO 2006112330 A1 20061026 WO 2006-JP307751 20060412
DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, KE, KG, KM, KN, KP, KR,
VN, YU, ZA, ZM, ZW
JP 2006298781 A 20061102 JP 2005-119098 20050415
JP 2005-119098 A 20050415
Abstract
Disclosed is an agent for inhibiting the transporter activity of an estrone-3-sulfate transporter, an agent for inhibiting the growth of
breast cancer cells, or an agent for the treatment of breast cancer, which does not need to be incorporated in cells, has excellent drug
delivery property and has few side effects. The agent comprises at least one component selected from genistein, quercetin,
ginkgolide C, theaflavin, theaflavin 3-o-gallate, chalcone, rutin, daidzein, daidzin, flavanone, flavonol, geraldol, hesperetin,
hespereridine, ipriflavone, luteolin-7-o-glucoside, methoxychalcone, 4'-methyl-7-methoxy-isoflavone, 5-morin, myricetin, naringenin,
naringenin-7-glycoside, naringin, neohesperidin dihydrochalcone, nomilin, primuletin, poncirin, scutellarein, catechin hydrate, and chem.
modified products thereof.
Answer 349:
The new use of 3,5,7,3',4',5'-hexa-hydroxyl-2,3-flavanone in pharmaceutical. Zhu, Banghao; Liu, Deyu. (Sun Yat-Sen
flavanone
University, Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 13pp. CODEN: CNXXEV CN 1846695
A 20061018 Patent written in Chinese. Application: CN 1003-3775 20060221. Priority: . CAN 145:511418 AN 2006:1112871

CN 1846695 A 20061018 CN 2006-10033775 20060221
CN 2006-10033775 20060221
Abstract
The patent relates to new use of 3,5,7,3',4',5'-hexa-hydroxyl-2,3-flavanone to prep. inhibitor of saccharifying end product, antioxidant,
inhibitor of diacylglycerol-protein kinase C. Said medicine is comprised of 3,5,7,3',4',5'-hexa-hydroxyl-2,3-flavanone and
pharmaceutically acceptable adjuvant. The dose type may be injections, oral prepns., and targeting prepns. Said
3,5,7,3',4',5'-hexa-hydroxyl-2,3-flavanone is extd. from Vitis vinifera with alcs.
Answer 350:
TCDD-Induced CYP1A1 Expression, an Index of Dioxin Toxicity, Is Suppressed by Flavonoids Permeating the Human
Intestinal Caco-2 Cell Monolayers. Hamada, Mika; Satsu, Hideo; Natsume, Yayoi; Nishiumi, Shin; Fukuda, Itsuko; Ashida,
Hitoshi; Shimizu, Makoto. Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The
University of Tokyo, Yayoi, Bunkyo-ku, Japan. Journal of Agricultural and Food Chemistry (2006), 54(23), 8891-8898.
Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 146:56725 AN
Abstract
Since the toxicol. effects of dioxins are mainly mediated by the aryl hydrocarbon receptor (AhR), an in vitro assessment system for
AhR activity was used in this study to search for flavonoids that attenuated dioxin toxicity through the intestinal epithelial monolayer.
When AhR transformation in Hepa-1c1c7 cells was examd. by southwestern ELISA, nine flavonoids among 34 kinds of flavonoids
inhibited the transformation by more than one-half. When each flavonoid with 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) was added to
dioxin-responsive HepG2 cells, seven flavonoids significantly restrained the TCDD-induced transcriptional activity of the CYP1A1
promoter. Furthermore, those seven flavonoids that had permeated the Caco-2 cell monolayers demonstrated an inhibitory effect on
both the AhR transformation and on the transcriptional activity of the CYP1A1 promoter. The expression level of the CYP1A1 mRNA
and protein induced by TCDD was suppressed by flavone, galangin, and tangeretin. It is proposed from these results that some
flavonoids have the ability to suppress dioxin-induced AhR activity after permeating the human intestinal epithelial cell monolayer.
Answer 351:
Montamine, a unique dimeric indole alkaloid, from the seeds of Centaurea montana (Asteraceae), and its in vitro cytotoxic
activity against the CaCo2 colon cancer cells. Shoeb, Mohammad; MacManus, Stephen M.; Jaspars, Marcel; Trevidu, Jioji;
flavanone
Nahar, Lutfun; Kong-Thoo-Lin, Paul; Sarker, Satyajit D. Department of Chemistry, University of Dhaka, Dhaka, Bangladesh.
Tetrahedron (2006), 62(48), 11172-11177. Publisher: Elsevier Ltd., CODEN: TETRAB ISSN: 0040-4020. Journal written in English.
Abstract
Reversed-phase HPLC anal. of the methanol ext. of the seeds of Centaurea montana afforded a flavanone, montanoside (4), 6
epoxylignans, berchemol (7), berchemol 4'-O-β-D-glucoside (5), pinoresinol (10), pinoresinol 4-O-β-D-glucoside (8), pinoresinol
4,4'-di-O-β-D-glucoside (6), pinoresinol 4-O-apiose-(1→2)-β-D-glucoside (9), two quinic acid derivs., trans-3-O-p-coumaroylquinic acid
(1), cis-3-O-p-coumaroylquinic acid (2), and 8 indole alkaloids, tryptamine (3), N-(4-hydroxycinnamoyl)-5-hydroxytryptamine (11),
cis-N-(4-hydroxycinnamoyl)-5-hydroxytryptamine (12), centcyamine (16), cis-centcyamine (17), moschamine (13), cis-moschamine
(14) and a dimeric indole alkaloid, montamine (15). While the structures of 2 new compds., montanoside (4) and montamine (15), were
established unequivocally by UV, IR, MS and a series of 1D and 2D NMR analyses, all known compds. were identified by comparison
of their spectroscopic data with literature data. The antioxidant properties of these compds. were assessed by the DPPH assay, and
their toxicity towards brine shrimps and cytotoxicity against CaCo-2 colon cancer cells were evaluated by the brine shrimp lethality and
the MTT cytotoxicity assays, resp. The novel dimer, montamine (15), showed significant in vitro anticolon cancer activity (IC50 = 43.9
μM) while that of the monomer, moschamine (13), was of a moderate level (IC50 = 81.0 μM).
Answer 352:
Protein Tyrosine Phosphatase-1B Inhibitory Activity of Isoprenylated Flavonoids Isolated from Erythrina mildbraedii. Na,
MinKyun; Jang, JunPil; Njamen, Dieudonne; Mbafor, Joseph Tanyi; Fomum, Zacharias Tanee; Kim, Bo Yeon; Oh, Won Keun; Ahn,
Jong Seog. Korea Research Institute of Bioscience and Biotechnology (KRIBB), Daejeon, S. Korea. Journal of Natural Products
(2006), 69(11), 1572-1576. Publisher: American Chemical Society-American Society of Pharmacognosy, CODEN: JNPRDF ISSN:
Abstract
Inhibition of protein tyrosine phosphatase-1B (PTP1B) has been proposed as a therapy for treatment of type-2 diabetes and obesity.
Bioassay-guided fractionation of an EtOAc-sol. ext. of the root bark of Erythrina mildbraedii, using an in vitro PTP1B inhibitory assay,
resulted in the isolation of three new isoprenylated flavonoids, abyssinone-IV-4'-O-Me ether (2),
7-hydroxy-4'-methoxy-3'-(3-hydroxy-3-methyl-trans-but-1-enyl)-5'-(3-methylbut-2-enyl)flavanone (3), and abyssinone-VI-4-O-Me ether
(6), along with six known flavonoids, abyssinone-V-4'-O-Me ether (1), abyssinone-V (4), abyssinone-IV (5), sigmoidin E (7),
4'-hydroxy-5,7-dimethoxyisoflavone (8), and alpinumisoflavone (9). Compds. 1 and 2, 4-7, and 9 inhibited PTP1B activity, with IC50
values ranging from 14.8 ± 1.1 to 39.7 ± 2.5 μM. On the basis of the data obtained, flavanones and chalcones with isoprenyl groups
may be considered as a new class of PTP1B inhibitors.
Answer 353:
Development of DNA markers for identification of onion cultivars. Usui, Yuichi; Adachi, Shizuka; Kamiya, Motokazu;
Nakashima, Toshiki; Yamamoto, Yoshihisa; Suzuki, Tadanao; Yasui, Akemi. Incorporated Administrative Agency Center for Food
Quality, Labeling and Consumer Services, 2-1 Shintoshin, Chuuou-ku, Saitama City, Saitama, Japan. Nippon Shokuhin Kagaku
Kogaku Kaishi (2006), 53(9), 498-504. Publisher: Nippon Shokuhin Kagaku Kogakkai, CODEN: NSKKEF ISSN: 1341-027X. Journal
written in Japanese. CAN 146:398322 AN 2006:1107441 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
flavanone
The possibility of identification of onion (Allium cepa L.) cultivars by DNA anal. was investigated. The genetic diversity of twenty
onion cultivars from Japan, New Zealand, Australia, the USA and Thailand were examd., and 19 sets of sequence-tagged site (STS)
primers were designed. Discriminating bands were amplified by each set of STS primers using DNA extd. from 24 onion bulbs of each
cultivar. Individual variations in DNA bands in each cultivar were shown, which caused difficulties in discrimination between cultivars
in the case of two sets of STS primers which were designed from cytoplasmic DNA (chloroplastic and mitochondrial DNA). However,
some individual variations were shown in each cultivar by using the other seventeen sets of STS primers which were designed based
on genomic DNA. These results suggested that the identification of onion cultivars using a single onion bulb is impossible. However,
because it was shown that the population of allele frequency derived from each cultivar tended to be const., it may be possible to
identify onion cultivars using a significance test to compare allele frequencies of two populations derived from multiple onion bulbs of
two varieties.
Answer 354:
Modulation of the age-related nuclear factor-κB (NF-κB) pathway by hesperetin. Kim, Ji Young; Jung, Kyung Jin; Choi, Jae
Sue; Chung, Hae Young. College of Pharmacy, Pusan National University, Pusan, S. Korea. Aging Cell (2006), 5(5), 401-411.
Publisher: Blackwell Publishing Ltd., CODEN: ACGECQ ISSN: 1474-9718. Journal written in English. CAN 145:389298 AN
Abstract
Nuclear factor-κB (NF-κB), a redox-sensitive transcription factor, plays an important role in the aging process. Thus, developing and
identifying specific components that modulate NF-κB without adverse side-effects would be of major importance. Hesperetin, a
flavanone abundant in citrus fruits, has a variety of pharmacol. properties being antioxidant, cholesterol-lowering, and
anti-inflammatory. In this study, we investigated how hesperetin fed to 6- and 24-mo-old rats modulates NF-κB in their kidneys.
Results showed that hesperetin suppressed NF-κB activation and related gene expressions. An even more interesting finding is that
hesperetin suppressed NF-κB through four signal transduction pathways, NIK/IKK, ERK, p38, and JNK. Further evidence showed the
remarkable efficacy of hesperetin to suppress the translocation of Trx/Ref-1, indicating its beneficial effect on the redox status. The
most significant findings of the current study report new information on the use of hesperetin as a potential anti-aging agent.
Answer 355:
Genome-wide analysis of the structural genes regulating defense phenylpropanoid metabolism in Populus. Tsai,
Chung-Jui; Harding, Scott A.; Tschaplinski, Timothy J.; Lindroth, Richard L.; Yuan, Yinan. Biotechnology Research Center, School
of Forest Resources and Environmental Science, Michigan Technological University, Houghton, MI, USA. New Phytologist
(2006), 172(1), 47-62. Publisher: Blackwell Publishing Ltd., CODEN: NEPHAV ISSN: 0028-646X. Journal written in English. CAN
Abstract
Salicin-based phenolic glycosides, hydroxycinnamate derivs. and flavonoid-derived condensed tannins comprise up to one-third of
Populus leaf dry mass. Genes regulating the abundance and chem. diversity of these substances have not been comprehensively
analyzed in tree species exhibiting this metabolically demanding level of phenolic metab. Here, shikimate-phenylpropanoid pathway
genes thought to give rise to these phenolic products were annotated from the Populus genome, their expression assessed by
semiquant. or quant. reverse transcription polymerase chain reaction (PCR), and metabolic evidence for function presented. Unlike
Arabidopsis, Populus leaves accumulate an array of hydroxycinnamoyl-quinate esters, which is consistent with broadened function of
the expanded hydroxycinnamoyl-CoA transferase gene family. Greater flavonoid pathway diversity is also represented, and flavonoid
gene families are larger. Consistent with expanded pathway function, most of these genes were upregulated during wound-stimulated
flavanone
condensed tannin synthesis in leaves. The suite of Populus genes regulating phenylpropanoid product accumulation should have
important application in managing phenolic carbon pools in relation to climate change and global carbon cycling.
Answer 356:
Regioselectivity of 7-O-methyltransferase of poplar to flavones. Kim, Bong-Gyu; Kim, Hojung; Hur, Hor-Gil; Lim, Yoongho; Ahn,
Joong-Hoon. Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Seoul, S. Korea.
Journal of Biotechnology (2006), 126(2), 241-247. Publisher: Elsevier B.V., CODEN: JBITD4 ISSN: 0168-1656. Journal written in
Abstract
POMT-7, an O-methyltransferase from poplar (Populus deltoids) was used to modify a variety of flavonoid compds. POMT-7 was able
to transfer a Me group to several flavonoids contg. a C-7 hydroxyl group. However, POMT-7 showed a higher affinity toward flavonol
and flavone such as apigenin, kaempferol, luteolin, and quercetin than flavanone and isoflavone. Based on comparison of HPLC
retention times with authentic compds. and corresponding NMR spectroscopy data, the methylation position of the reaction products
was detd. to be at the hydroxyl group of C-7. Biotransformation kinetics indicated that the enzyme converted more than 80% of the
apigenin, kaempferol, luteolin and quercetin substrates, which were added at concn. of 70 μM, into corresponding 7-methoxy compds.
within 24 h.
Answer 357:
Medical composition containing flavones of Sarcandra glabra extract and its application. Lian, Xiaoyuan; Zhang, Zhizhen;
Tang, Zulin. (Jiangxi Boshilian Science and Technology Research and Development Co., Ltd., Peop. Rep. China). Faming Zhuanli
Shenqing Gongkai Shuomingshu (2006), 14pp. CODEN: CNXXEV CN 1839903 A 20061004 Patent written in Chinese.
SciFinder (R))

CN 1839903 A 20061004 CN 2006-10049219 20060118
CN 2006-10049219 20060118
Abstract
The medical compn. contains effective position or effective constituent extd. Sarcandra glabra which comprises flavones, and/or
saponin, and/or polyoses such as isofraxidin-7-O-glucoside, 5,7-dihydroxy flavanone, 2',6'-dihydroxy-4'-methoxyl chalcone,
pinostrobin, dihydromyricetin, pelargonidin, astilbin, naringenin-4',7-dimethyl ether. The purity of effective constituent is 50-99 %. The
medical compn. comprises oral tablets, buccal tablets, chewing tablets; injections comprising small injections, large injections, powder
injections, emulsions, suspensions, pills, dripping pills, capsules, soft capsules, granules, intumescent prepns., oral solns., syrups,
mixts., sustained-release prepns., controlled-release prepns., and targeting prepns. The invention may be used in antitumor agents,
flavanone
synergistic attenuation, toxic response of radiotherapy and chemotherapy. The injection can treat bleeding due to blood-heat, skin
purple plague, primary thrombocytopenic purpura and secondary thrombocytopenic purpura, thrombocythemia, pharyngolaryngitis,
tracheobronchitis, pulmonitis, keratitis, cellulitis, and appendicitis.
Answer 358:
Anti-inflammatory agent and immuno-reaction inhibition agent comprising flavonoid isolated from Artemisia sylvatica which
inhibit expression of inflammation factor. Lee, Jung Joon; Lee, Jeong Hyung; Lee, Dong Ho; Hong, Young Soo. (Korea
Research Institute of Bioscience and Biotechnology, S. Korea). Repub. Korean Kongkae Taeho Kongbo (2006), No pp. given.
CODEN: KRXXA7 KR 2006014534 A 20060216 Patent written in Korean. Application: KR 2004-63108 20040811. Priority: .

KR 2006014534 A 20060216 KR 2004-63108 20040811
KR 2004-63108 20040811
Abstract
An anti-inflammatory agent and an immuno-reaction inhibition agent comprising novel flavonoid are provided to inhibit
transcriptional-promotion activity of RelA/p65, thereby inhibiting nuclear factor kappa B activity, generation of NO and secretion of
TNF-α. The compd. is selected from the group consisting of 4'-demethyl eupatilin, cirsilineol, 5,6,4'-trihydroxy-7,3'-dimethoxyflavone,
8,4'-dihydroxy-3,7,2'-trimethoxyflavone, chrysoplenetin, and 5,8,4'-trihydroxy-flavanone. The method for isolating the compd. from
Artemisia sylavatica comprises the steps of: (a) extg. stem of Artemisia sylavatica with water, alc., or a mixt. solvent thereof; (b)
partitioning the ext. into a hexane layer and a water layer; (c) repeatedly extg. the water layer with ethylacetate; and (d) resp. purifying
the hexane layer and the ethylacetate layer through repetitive chromatog.
Answer 359:
Molecular evolution and functional specialization of chalcone synthase superfamily from Phalaenopsis Orchid. Han,
Ying-Ying; Ming, Feng; Wang, Wei; Wang, Jing-Wen; Ye, Ming-Ming; Shen, Da-Leng. Institute of Genetics, State Key Laboratory of
Genetic Engineering, Research Centre of Gene Diversity and Designed Agriculture, Ministry of Education Key Laboratory for
Biodiversity Science and Ecological Engineering, School of Life Science, Fudan University, Shanghai, Peop. Rep. China. Genetica
(Dordrecht, Netherlands) (2006), 128(1-2-3), 429-438. Publisher: Springer, CODEN: GENEA3 ISSN: 0016-6707. Journal written in
Abstract
Plant genomes appear to exploit the process of gene duplication as a primary means of acquiring biochem. and developmental
flexibility. The best example is the gene encoding chalcone synthase (CHS, EC2.3.1.74), the first committed step in flavonoid
biosynthesis. In this study, we examd. the mol. evolution of three CHS family members of Phalaenopsis including a novel chs gene
flavanone
(phchs5), which is slowly evolved. The inferred phylogeny of the chs genes of Phalaenopsis with other two orchid plants, Bromoheadia
finlaysoniana and Dendrobium hybrid, suggested that gene duplication and divergence have occurred before divergence of these three
genera. Relatively quant. RT-PCR anal. identified expression patterns of these three chs genes in different floral tissues at different
developmental stages. Phchs5 was the most abundantly expressed chs gene in floral organs and it was specifically transcribed in
petal and lip at the stages when anthocyanin accumulated (stage 1-4). Phchs3 and phchs4 were expressed at much lower levels than
phchs5. Phchs3 was expressed in pigmented tissue (including lip, petal and sepal) at middle stages (stages 2-4) and in colorless
reproductive tissue at late stage (stage 5). Phchs4 was only expressed in petal at earlier stages (stage 1-3) and in lip at middle stage
(stage 4). These results present new data on differentiation of gene expression among duplicate copies of chs genes in Phalaenopsis.
Answer 360:
Antioxidant and neuroprotective effects of hesperidin and its aglycone hesperetin. Cho, Jungsook. Department of
Pharmacology, College of Medicine, Dongguk University, Gyeongbuk, S. Korea. Archives of Pharmacal Research (2006), 29(8),
699-706. Publisher: Pharmaceutical Society of Korea, CODEN: APHRDQ ISSN: 0253-6269. Journal written in English. CAN
Abstract
The present study evaluated antioxidant and neuroprotective activities of hesperidin, a flavanone mainly isolated from citrus fruits,
and its aglycon hesperetin using cell-free bioassay system and primary cultured rat cortical cells. Both hesperidin and hesperetin
exhibited similar patterns of 1,1-diphenyl-2-picrylhydrazyl radical scavenging activities. While hesperidin was inactive, hesperetin was
found to be a potent antioxidant, inhibiting lipid peroxidn. initiated in rat brain homogenates by Fe2+ and L-ascorbic acid. In
consistence with these findings, hesperetin protected primary cultured cortical cells against the oxidative neuronal damage induced by
H2O2 or xanthine and xanthine oxidase. In addn., it was shown to attenuate the excitotoxic neuronal damage induced by excess
glutamate in the cortical cultures. When the excitotoxicity was induced by the glutamate receptor subtype-selective ligands, only the
N-methyl-D-aspartic acid-induced toxicity was selectively and markedly inhibited by hesperetin. Furthermore, hesperetin protected
cultured cells against the Aβ25-35-induced neuronal damage. Hesperidin, however, exerted minimal or no protective effects on the
neuronal damage tested in this study. Taken together, these results demonstrate potent antioxidant and neuroprotective effects of
hesperetin, implying its potential role in protecting neurons against various types of insults assocd. with many neurodegenerative
diseases.
Answer 361:
Two new antibacterial flavanones from Sophora flavescens. Cao, Mei Ai; Sun, Xiao Bai; Zhao, Pei Hua; Yuan, Cheng Shan.
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou,
Peop. Rep. China. Chinese Chemical Letters (2006), 17(8), 1048-1050. Publisher: Chinese Chemical Society, CODEN: CCLEE7
SciFinder (R))
Abstract
Two new lavandulylated flavanones, (2R,3R)-8-lavandulyl-2'-methoxy-5,7,4'-trihydroxyflavanonol (1) and

8-lavandulyl-5,7,4'-trihydroxyflavonol (2), were isolated from the dry roots of Sophara flavescens. Their structures were elucidated on
the basis of spectroscopic data. Compds. 1 and 2 exhibited significant antibacterial activities.
Answer 362:
flavanone
Phytoestrogens as inhibitors of the human progesterone metabolizing enzyme AKR1C1. Brozic, Petra; Smuc, Tina; Gobec,
Stanislav; Rizner, Tea Lanisnik. Institute of Biochemistry, Medical Faculty, University of Ljubljana, Ljubljana, Slovenia.
Molecular and Cellular Endocrinology (2006), 259(1-2), 30-42. Publisher: Elsevier Ltd., CODEN: MCEND6 ISSN: 0303-7207.
Abstract
Phytoestrogens are plant-derived, non-steroidal constituents of our diets. They can act as agonists or antagonists of estrogen
receptors, and they can modulate the activities of the key enzymes in estrogen biosynthesis. Much less is known about their actions
on the androgen and progesterone metabolizing enzymes. We have examd. the inhibitory action of phytoestrogens on the key human
progesterone-metabolizing enzyme, 20α-hydroxysteroid dehydrogenase (AKR1C1). This enzyme inactivates progesterone and the
neuroactive 3α,5α-tetrahydroprogesterone, to form their less active counterparts, 20α-hydroxyprogesterone and
5α-pregnane-3α,20α-diol, resp. We overexpressed recombinant human AKR1C1 in Escherichia coli, purified it to homogeneity, and
examd. the selected phytoestrogens as inhibitors of NADPH-dependent redn. of a common AKR substrate, 9,10-phenanthrenequinone,
and progesterone. The most potent inhibitors were 7-hydroxyflavone, 3,7-dihydroxyflavone and flavanone naringenin with IC50 values
in the low μM range. Docking of the flavones in the active site of AKR1C1 revealed their possible binding modes, in which they are
sandwiched between the Leu308 and Trp227 of AKR1C1.
Answer 363:
Determination of total flavanone quantity hawthorn by micellar enhanced fluorimetry. Li, Man-Xiu; Bai, Bao-Lin; Zhang,
Xiao-Li; Li, Hai-Ping. Department of Chemistry, Xinzhou Teachers University, Xinzhou, Shanxi, Peop. Rep. China. Guangpu
Shiyanshi (2006), 23(4), 690-693. Publisher: Kexue Chubanshe, CODEN: GUSHEH ISSN: 1004-8138. Journal written in Chinese.
Abstract
The fluorimetry was applied to det. the total flavanone quantity of hawthorn and hyperin was used as the comparison. The exptl.
conditions were optimized as follows abs. alc. was used as solvent, the amts. of pure ethanolamine and surface active agent CTMAB
(1.2 × 10-3 mol/L) was 0.5 mL and 0.6 mL, resp., the soln. was detd. under the room temp. At max. excitation wavelength of 457 nm
and emission wavelength of 531 nm, the fluorescence intensity was measured. The detective limits is 2.4 × 10-7 mol/L in the linear
range of 4 × 10-7 - 1.5 × 10-5 mol/L, RSD of the method is 1.64%. The method is simple, rapid, and accurate with a potential in anal.
applications.
Answer 364:
Skin care compositions comprising hydrolyzed fucoidan. Mower, Thomas E. (USA). U.S. Pat. Appl. Publ. (2006), 15pp.,
Cont.-in-part of U.S. Ser. No. 83,826. CODEN: USXXCO US 2006210524 A1 20060921 Patent written in English. Application: US
2006-306997 20060118. Priority: US 2005-83826 20050318. CAN 145:362868 AN 2006:978988 CAPLUS (Copyright (C) 2008

flavanone

US 20060210524 A1 20060921 US 2006-306997 20060118
US 20060210609 A1 20060921 US 2005-83826 20050318
WO 2007084721 A2 20070726 WO 2007-US1536 20070118
WO 2007084721 A3 20080214
EP, OA
US 2005-83826 A2 20050318
US 2006-306996 A 20060118
US 2006-306997 A 20060118
US 2006-307031 A 20060119
US 2006-307032 A 20060119
Abstract
Skin care compns. for the care of wrinkles including partially hydrolyzed fucoidan, a base, and an anti-wrinkle compd. The partially
hydrolyzed fucoidan may be sulfonated. The partially hydrolyzed fucoidan may be derived from Japanese mozuku seaweed,
Japanese kombu seaweed, or Tongan limu moui seaweed. Also disclosed is a method of making the skin care compn.
Answer 365:
Enhanced therapeutic potential of naringenin-phospholipid complex in rats. Maiti, Kuntal; Mukherjee, Kakali; Gantait,
Arunava; Saha, Bishnu Pada; Mukherjee, Pulok K. School of Natural Product Studies, Department of Pharmaceutical Technology,
Faculty of Engineering and Technology, Jadavpur University, Kolkata, India. Journal of Pharmacy and Pharmacology (2006),
58(9), 1227-1233. Publisher: Pharmaceutical Press, CODEN: JPPMAB ISSN: 0022-3573. Journal written in English. CAN
Abstract
Naringenin is a naturally occurring flavanone, possessing a variety of biol. activity. Due to its rapid elimination, naringenin needs
frequent administration to maintain an effective plasma concn. We have evaluated the therapeutic potential of naringenin-phospholipid
complex under oxidative stress conditions compared with free naringenin. Naringenin-phospholipid complex was prepd. and assessed
for antioxidant activity in carbon tetrachloride intoxicated rats at a dose level of 100 mg kg-1 (p.o.). Liver function tests were studied
by assessing serum glutamate oxaloacetate transaminase, serum glutamate pyruvate transaminase, serum alk. phosphatase and total
bilirubin. Marker enzymes of liver, namely glutathione peroxidase, superoxide dismutase, catalase and thiobarbituric acid reactive
substances, were measured to evaluate the antioxidant potential at the same dose level. The plasma concn. of naringenin was also
flavanone
measured. It was obsd. that the naringenin-phospholipid complex enhanced the antioxidant activity of the biomol. and protected the
liver significantly for a longer time as compared with free naringenin at the same dose level. Phospholipid complex of naringenin
produced better antioxidant activity than the free compd. with a prolonged duration of action, which may be helpful in reducing the fast
elimination of the mol. from body.
Answer 366:
Identification of O-diglycosyl flavanones in Fructus aurantii by liquid chromatography with electrospray ionization and
collision-induced dissociation mass spectrometry. Zhou, Da-yong; Xu, Qing; Xue, Xin-ya; Zhang, Fei-fang; Liang, Xin-miao.
Biotechnology Department, Dalian Institute of Chemical Physics, The Chinese Academy of Sciences, Dalian, Peop. Rep. China.
Journal of Pharmaceutical and Biomedical Analysis (2006), 42(4), 441-448. Publisher: Elsevier B.V., CODEN: JPBADA ISSN:
Abstract
This study reported the application of LC-ESI/MS method to characterize O-diglycosyl flavanones of traditional Chinese medicine
Fructus aurantii(Zhiqiao) and UPLC retention parameters method to expatiate the structure-retention relationship of these O-diglycosyl
flavanones. The ext. of F. aurantii was found contg. neoeriocitrin, isonaringin, naringin, hesperidin, neohesperidin, and neoponcirin.
Tandem mass spectrometric method was utilized to elucidate structure and differentiate the interglycosidic linkage of isomeric
O-diglycosyl flavanones. Based on the relative abundance of fragments formed by fragmentation at glycosidic bonds in pos. ion
mode and CID MS spectra of deprotonated mol. [M-H]- in neg. ion mode, the interglycosidic linkage of O-diglycosyl flavanones
(flavonoid O-neohesperidosides and O-rutinosides, 1,2- and 1,6-) can be unambiguously differentiated. UPLC and a CSASS software
were performed to obtain the retention parameters a, c and k values of these compds. The Δa, Δc, and α values within compd. pair
naringin to neoriocitrin, neoponcirin to neohesperidin, naringin to isonaringin, neohesperidin to hesperidin, hesperidin to isonaringin,
neohesperidin to naringin were calcd. We found there were some relationship between structure and retention parameters.
Answer 367:
High-performance liquid chromatographic enantioseparations on capillary columns containing crosslinked polysaccharide

phenylcarbamate derivatives attached to monolithic silica. Chankvetadze, Bezhan; Kubota, Takateru; Ikai, Tomoyuki;
Yamamoto, Chiyo; Kamigaito, Masami; Tanaka, Nobuo; Nakanishi, Kazuki; Okamoto, Yoshio. Molecular Recognition and Separation
Science Laboratory, School of Chemistry, Tbilisi State University, Tbilisi, Georgia. Journal of Separation Science (2006), 29(13),
1988-1995. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: JSSCCJ ISSN: 1615-9306. Journal written in English.
Abstract
Monolithic capillary columns contg. native silica gel were covalently modified with 3,5-disubstituted phenylcarbamate derivs. of
cellulose and amylose and applied for enantiosepns. in capillary LC. The method previously used for covalent immobilization of
polysaccharide phenylcarbamate derivs. onto the surface of microparticulate silica gel was successfully adapted for in situ
modification of monolithic fused-silica capillary columns. The effects of the nature of polysaccharide and the substituents, and of
multiple covalent immobilization of polysaccharide deriv. on chromatog. performance of capillary columns were studied. The capillary
columns obtained using this technique are stable in all solvents commonly used in LC and exhibit promising enantiomer resolving
ability.
Answer 368:
flavanone
Quantum chemistry study on fluorescence spectra of four flavanone derivatives. Su, Yu; Liu, Shan; Yang, Ming; Liao,
Xian-wei. Teaching and Research Group of Chemistry, Northern Sichuan Medical College, Nanchong, Peop. Rep. China. Xinan
Minzu Daxue Xuebao, Ziran Kexueban (2006), 32(4), 693-696. Publisher: Xinan Minzu Daxue Xuebao, Ziran Kexueban Bianjibu,
CODEN: XMDXAF Journal written in Chinese. CAN 147:157260 AN 2006:958381 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
Flavanone compds. generally have a bigger conjugate system. They are good electronic luminescence materials. Four kinds of
flavanone derivs. have been optimized at the B3LYP/6-311G level. There is no imaginary frequency in vibrational anal. On these
bases, their electronic spectra are calcd. by CIS method at B3LYP/6-311G level. The calcd. results are basically consistent with exptl.
values. In addn., the results also indicate that the intramol. hydrogen bonding of the three compds. has been formed and the bond
length is about 1.75-1.82°.
Answer 369:
Composition for improving skin, hair and coat health containing flavanones. Richelle, Myriam; Offord-Cavin, Elizabeth;
Bortlik, Karlheinz; Bureau-Franz, Isabelle; Williamson, Gary; Nielsen, Inge Lise; Steiling, Heike; Moodycliffe, Angus. (Nestec S.A.,
Switz.). PCT Int. Appl. (2005), 26 pp. CODEN: PIXXD2 WO 2005058255 A1 20050630 Designated States W: AE, AG, AL, AM,
AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH,
GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO,
NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM,
ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG,
CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2004-EP14416 20041217. Priority: EP
2003-29183 20031218. CAN 145:299737 AN 2006:956792 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))

WO 2005058255 A1 20050630 WO 2004-EP14416 20041217
DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ,
LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT,
RO, RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM,
ZW
RW: BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ,
TM, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LT, LU, MC, NL, PL, PT,
RO, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG
EP 1543810 A1 20050622 EP 2003-29183 20031218
R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT, IE, SI, LT, LV, FI, RO, MK, CY, AL,
TR, BG, CZ, EE, HU, SK
AU 2004298356 A1 20050630 AU 2004-298356 20041217
CA 2549509 A1 20050630 CA 2004-2549509 20041217
CN 1893909 A 20070110 CN 2004-80037849 20041217
EP 1750651 A1 20070214 EP 2004-804019 20041217
flavanone
R: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LI, LT, LU, MC, NL, PL, PT,
RO, SE, SI, SK, TR
BR 2004017723 A 20070403 BR 2004-17723 20041217
JP 2007514695 T 20070607 JP 2006-544359 20041217
IN 2006DN03349 A 20070824 IN 2006-DN3349 20060609
US 20070129428 A1 20070607 US 2006-596468 20060614
MX 2006PA06773 A 20060904 MX 2006-PA6773 20060615
NO 2006003200 A 20060912 NO 2006-3200 20060710
EP 2003-29183 A 20031218
WO 2004-EP14416 W 20041217
Abstract
The present invention pertains to a compn. for preventing, decreasing and/or treating skin and hair/coat disorders, such as is effected
by inflammatory reactions, environmental factors, aging or cancer. In particular, the present invention relates to the use of
flavanones compds. or their derivs. in nutritional, cosmetic or pharmaceutical compns. for improvement of human or pet animal skin
and coat conditions. For example, mineral water was prepd. by adding hesperetin-7-glucose, in an amt. of 0.01 mg to 200 mg per L,
estg. that the av. consumption is of about 1 L per day.
Answer 370:
cDNA cloning and expression of anthocyanin biosynthetic genes in wild potato (Solanum pinnatisectum). Lu, Qi-Neng;
Yang, Qing. Department of Biochemistry and Molecular Biology, College of Life Sciences, Nanjing Agricultural University, Nanjing,
Peop. Rep. China. African Journal of Biotechnology (2006), 5(10), 811-818. Publisher: Academic Journals, CODEN: AJBFAH
ISSN: 1684-5315. http://www.academicjournals.org/AJB/PDF/pdf2006/16May/Semagn%20et%20al.pdf Journal; Online Computer File
Abstract
The purple anthocyanins in potato tuber skin and flesh are primarily derived from petunidin. CDNA clones encoding the enzymes
involved in anthocyanin biosynthesis, chalcone synthase (CHS), flavanone 3-hydroxylase (F3H), dihydroflavonol 4-reductase (DRF),
and UDP-glucose:flavonoid 3-O-glucosyltransferase (3GT), were isolated from Solanum pinnatisectum by RT-PCR with degenerated
primers. Sequence comparison showed that they share 76-96% identities with each corresponding solanaceous gene reported
previously. Each gene is a member of a multigene family. The spatial expression anal. indicated that these genes were preferentially
expressed in flowers, stolons and terminal buds, and their transcripts could not detected in roots except 3GT. All the genes were
induced expression in tuber skins by white light, and followed by anthocyanin accumulation. This is the first report cloning and
expression of anthocyanin biosynthetic genes in wild potato (Solanum pinnatisectum).
Answer 371:
Transcriptional regulation of the flavonoid pathway in the skin of dark-grown 'Cripps' Red' apples in response to sunlight.
flavanone
Takos, Adam M.; Robinson, Simon P.; Walker, Amanda R. Division of Plant Industry, Adelaide Laboratory, Commonwealth
Scientific and Industrial Research Organisation, Glen Osmond, South Australia, Australia. Journal of Horticultural Science &
Biotechnology (2006), 81(4), 735-744. Publisher: Headley Brothers Ltd., CODEN: JHSBFA ISSN: 1462-0316. Journal written in
Abstract
Flavonoids, including anthocyanins, flavonols, and condensed tannins (CTs), are synthesized by a common biosynthetic pathway.
Anthocyanins are responsible for the red color in apple fruits, while CTs and flavonols are potent anti-oxidants which may be beneficial
in the human diet. The effect of sunlight on flavonoid accumulation and gene transcription was investigated in fruit skin of the red
apple variety Malus × domestica cv. 'Cripps' Red'. Individual fruit growing on trees and covered with bags 46 d after full bloom
(DAFB) failed to accumulate anthocyanins by 147 DAFB, 2 wk before harvest. In contrast, control fruit, grown under natural light
conditions, accumulated anthocyanins up to 140 ng/mg fresh wt. (FW) of skin. The accumulation of flavonols was moderately
reduced in bagged fruit, but the synthesis of CTs was unaffected. Exposure of bagged fruit to sunlight induced anthocyanin synthesis
up to .apprx.30 ng/mg FW of skin after 13 d (harvest), but had no effect on the synthesis of flavonols or CTs. The synthesis of
anthocyanins correlated with an increase in the steady-state transcript levels of all flavonoid pathway genes except those specific for
CT synthesis. These data suggest that transcription of most apple flavonoid genes is controlled by a common regulatory mechanism
that is light-responsive.
Answer 372:
The inhibition of superoxide anion generation in human neutrophils by Viscum coloratum. Leu, Yann-Lii; Hwang,
Tsong-Long; Chung, Yu-Ming; Hong, Pao-Yun. Graduate Institute of Natural Products, College of Medicine, Chang Gung University,
Tao-Yuan, Taiwan. Chemical & Pharmaceutical Bulletin (2006), 54(7), 1063-1066. Publisher: Pharmaceutical Society of Japan,
CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN 145:431906 AN 2006:896921 CAPLUS (Copyright (C)
Abstract
One new 1,3-diphenylpropane, viscolin (1), and one new flavanone, (2S)-7,4'-dihydroxy-5,3'-dimethoxyflavanone (2), together with
thirty-nine known compds., which included eleven known flavanones, two chromones, fourteen benzenoids, one inositol, two
pyrimidines, four triterpenoids and five steroids, were isolated and characterized from Viscum coloratum. Structures of new compds.
were detd. by spectral anal. Among them, viscolin (1) showed the most significant inhibition on superoxide anion generation by human
neutrophils in response to fMLP (formyl-L-methionyl-L-leucyl-L-phenylalanine).
Answer 373:
Dissolution enhancement of flavonoids by solid dispersion in PVP and PEG matrixes: a comparative study. Kanaze, F. I.;
Kokkalou, E.; Niopas, I.; Georgarakis, M.; Stergiou, A.; Bikiaris, D. Department of Pharmacy, School of Health Sciences, Aristotle
University of Thessaloniki, Thessaloniki, Greece. Journal of Applied Polymer Science (2006), 102(1), 460-471. Publisher: John
Wiley & Sons, Inc., CODEN: JAPNAB ISSN: 0021-8995. Journal written in English. CAN 145:455609 AN 2006:896610
Abstract
Polyvinylpyrrolidone (PVP) and poly(ethylene glycol) (PEG) solid dispersion systems with flavanone glycosides, naringin and
flavanone
hesperidin, and their aglycons, naringenin and hesperetin, were prepd., using solvent evapn. method, to enhance their dissoln. rates
that may affect their bioavailability. Drug release of both flavanone glycosides and their aglycons was directly affected by the phys.
state of solid dispersions. Powder-x-ray diffraction technique in combination with scanning and TEM revealed that PVP polymer
formed amorphous nanodispersion systems with flavanone aglycons, while such systems could not be formed with their glycosides,
which are bulkier mols. Fourier transform IR spectra suggest the presence of hydrogen bonds between PVP carbonyl groups and
hydroxyl groups of both flavanone aglycons. These interactions prevent the crystn. of naringenin and hesperetin aglycons in PVP
matrix. The ability of PEG carrier to form hydrogen bonds with flavanone glycosides or aglycons was limited, and as a result both
flavanone glycosides and their aglycons remain in the cryst. form. For this reason, the soly. enhancement of PEG solid dispersions
was lower than when PVP was used as drug carrier. At pH 6.8, the % release of naringenin and hesperetin from
PVP/naringenin-hesperetin (80/20) solid dispersion was 100% while in PEG solid dispersions, it was not higher than 60-70%.
Answer 374:
Study on aromatic chemical constituents in Aralia subcapitata Hoo. Xu, Xudong; Yang, Lingshan. Institute of Medicinal Plant,
Chinese Academy of Medicinal Sciences, Peking Union Medical College, Beijing, Peop. Rep. China. Zhongguo Zhongyao Zazhi
(2005), 30(5), 398-399. Publisher: Zhongguo Zhongyao Zazhishe, CODEN: ZZZAE3 ISSN: 1001-5302. Journal written in Chinese.
Abstract
The arom. chem. constituents in Aralia subcapitata Hoo were studied. The dry bark of Aralia subcapitata Hoo was extd. by
dichloromethane and n-butanol, and the exts. were purified by silica gel column chromatog., Sephadex LH-20, and macroporous resin
column chromatog. resp. 4 Arom. chem. constituents were obtained and their structures were identified as 6,7-dimethoxycoumarin,
caffeic acid, 4'-hydroxy-flavanone-7-O-β-D-glucopyranoside, and isoliquiritin.
Answer 375:
Beneficial effect of hesperidin on lipopolysaccharide-induced hepatotoxicity. Kaur, Gaganjit; Tirkey, Naveen; Chopra,
Kanwaljit. Pharmacology Division, University Institute of Pharmaceutical Sciences, Panjab University, Chandigarh, India.
Toxicology (2006), 226(2-3), 152-160. Publisher: Elsevier Ltd., CODEN: TXCYAC ISSN: 0300-483X. Journal written in English.
Abstract
Hesperidin (HDN) is a flavanone glycoside abundantly found in citrus fruits. HDN has been reported to possess significant activities
against allergy, hemorrhoids, hormonal disorders and ulcers. Other reported activities include anti-inflammatory, analgesic,
antibacterial, antifungal, antiviral, antioxidant and free radical scavenger activity. A potentially important effect of endotoxin is the
increased prodn. of reactive oxygen intermediates as O2⋅-, peroxides and nitric oxide. The study reported here show a beneficial
effect of HDN in amelioration of endotoxin-induced hepatic dysfunction and oxidative stress in the liver of rats. Hepatotoxicity was
induced by administering lipopolysaccharide (LPS), in a single dose of 1 mg/kg i.p. to the rats. A marked hepatic dysfunction evident
by rise in serum levels of liver enzymes (ALT, AST, ALP) and total bilirubin (p < 0.05) was obsd. Serum and tissue nitrite levels were
also increased. LPS challenge further increased thiobarbituric acid reactive substances (TBARS) levels, whereas glutathione (GSH)
content and superoxide dismutase (SOD) activity were decreased in the liver homogenates of the rats showing a marked oxidative
stress. HDN administration successfully and dose dependently attenuated these effects of LPS. In conclusion, these findings
suggest that HDN attenuates LPS-induced hepatotoxicity possibly by preventing cytotoxic effects of NO and oxygen free radicals.
Answer 376:
flavanone
New flavanone from Dryopteris sublaeta. Feng, Weisheng; Cao, Xinwei; Zheng, Xiaoke; Kuang, Haixue. Henan College of
Traditional Chinese Medicine, Zhengzhou, Peop. Rep. China. Yaoxue Xuebao (2005), 40(5), 443-446. Publisher: Yaoxue Xuebao
Bianjibu, CODEN: YHHPAL ISSN: 0513-4870. Journal written in English. CAN 146:375811 AN 2006:868420 CAPLUS
Abstract
The chem. constituents of Dryopteris sublaeta Ching et Hsu were studied. Fresh plant of Dryopteris sublaeta Ching et Hsu was extd.
twice with boiling water, the ext. was concd. under reduced pressure at 50°. The concd. material was partitioned with ether, Et acetate,
and n-butanol. The fraction of ether ext. was chromatographed over silica gel column. The compds. were identified on the basis of
their physicochem. and spectral data. Four compds. were obtained and identified as
2(S)-5,7,3'-trihydroxy-6,8-dimethyl-5'-methoxy-flavanone (1), matteucinol (2), desmethoxymatteucinol (3), and
5,7,2'-trihydroxy-6,8-dimethyl-flavanone (4). Compd. 1 is a new one, the others are isolated from Dryopteris for the first time.
Answer 377:
Secondary metabolites from Phlomis syriaca and their antioxidant activities. Harput, U. Sebnem; Calis, Ihsan; Saracoglu,
Iclal; Donmez, Ali A.; Nagatsu, Akito. Faculty of Pharmacy, Department of Pharmacognosy, Hacettepe University, Ankara, Turk.
Turkish Journal of Chemistry (2006), 30(3), 383-390. Publisher: Scientific and Technological Research Council of Turkey, CODEN:
TJCHE3 ISSN: 1300-0527. Journal written in English. CAN 146:270143 AN 2006:866118 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
An iridoid glucoside, lamiide (1); 4 phenylethanoid glycosides, acteoside (2), β-OH acteoside (3), leucosceptoside A (4) and samioside
(5); a caffeic acid ester, chlorogenic acid (6); 2 flavone glucosides, luteolin-7-O-glucopyranoside (7) and
chrysoeriol-7-O-glucopyranoside (8); and a flavanone aglycon, naringenin (9), were isolated from the aerial parts of Phlomis syriaca.
The structures of the isolated compds. were elucidated by means of spectroscopic (UV, IR, 1D- and 2D-NMR, and FAB-MS) methods.
Free radical scavenging activity of the isolated compds. was detd. using the radical 2,2-diphenyl-1-picrylhydrazyl (DPPH),
spectroscopically.
Answer 378:
Gene-for-gene defense of wheat against the hessian fly lacks a classical oxidative burst. Giovanini, Marcelo P.; Puthoff,
David P.; Nemacheck, Jill A.; Mittapalli, Omprakash; Saltzmann, Kurt D.; Ohm, Herbert W.; Shukle, Richard H.; Williams, Christie E.
Department of Agronomy, Purdue University, West Lafayette, IN, USA. Molecular Plant-Microbe Interactions (2006), 19(9),
1023-1033. Publisher: APS Press, CODEN: MPMIEL ISSN: 0894-0282. Journal written in English. CAN 145:500633 AN
Abstract
Genetic similarities between plant interactions with microbial pathogens and wheat interactions with Hessian fly larvae prompted us to
flavanone
investigate defense and counterdefense mechanisms. Plant oxidative burst, a rapid increase in the levels of active oxygen species
(AOS) within the initial 24 h of an interaction with pathogens, commonly is assocd. with defenses that are triggered by gene-for-gene
recognition events similar to those involving wheat and Hessian fly larvae. RNAs encoded by Hessian fly superoxide dismutase
(SOD) and catalase (CAT) genes, involved in detoxification of AOS, increased in first-instar larvae during both compatible and
incompatible interactions. However, mRNA levels of a wheat NADPH oxidase (NOX) gene that generates superoxide (O2-) did not
increase. In addn., inhibiting wheat NOX enzyme with diphenyleneiodonium did not result in increased survival of avirulent larvae.
However, nitro blue tetrazolium staining indicated that basal levels of O2- are present in both uninfested and infested wheat tissue.
MRNA encoded by wheat genes involved in detoxification of the cellular environment, SOD, CAT, and glutathione-S-transferase did not
increase in abundance. Histochem. staining with 3,3-diaminobenzidine revealed no increases in wheat hydrogen peroxide (H2O2) during
infestation that were correlated with the changes in larval SOD and CAT mRNA. However, treatment with 2',7'-dichlorofluorescin
demonstrated the presence of basal levels of H2O2 in the elongation zone of both infested and uninfested plants. The accumulation
of a wheat flavanone 3-hydroxylase mRNA did show some parallels with larval gene mRNA profiles. These results suggested that
larvae encounter stresses imposed by mechanisms other than an oxidative burst in wheat seedlings.
Answer 379:
Theoretical calculations of circular dichroism of 3, 8"-biflavonoids. Ding, Yuanqing; Li, Xing Cong; Ferreira, Daneel. National
Center for Natural Products Research, The University of Mississippi, University, MS, USA. Abstracts of Papers, 232nd ACS
National Meeting, San Francisco, CA, United States, Sept. 10-14, 2006 (2006), CELL-105. Publisher: American Chemical Society,
Washington, D. C CODEN: 69IHRD Conference; Meeting Abstract; Computer Optical Disk written in English. AN 2006:857512
Abstract
CD (CD) has played an important role in detg. the abs. configuration of chiral mols. In particular, the recent advances on theor.
calcns. of CD spectra have greatly enhanced its value in this regard. The 3,8"-biflavonoids represent a biosynthetically important
group of natural products with significant biol. activities. The restricted rotation about the C3 - C8" interflavanyl bond has made it
extremely difficult to assign their abs. configurations. Although the empirical CD rule has attempted to address this issue, no solid
evidence, e.g., from total synthesis and X-ray crystallog., has been available to support the deduced abs. configurations. In the
current study, theor. calcns. of the electronic CD spectra of flavanone-(3->8")-flavone type and flavanone-(3->8")-dihydroflavonol
type biflavonoids have been carried out using time-dependant d. functional theory (TDDFT) with 6-31G* basis set in Gaussian03. The
results have provided profound evidence in interpreting the exptl. obsd. CD spectra, and thus unequivocally detg. the abs.
configurations of this class of compds.
Answer 380:
Production of composition of citrus fruits having increased content of flavanone compound by addition of glycosidase to
citrus fruits. Ahn, Jong Seog; Ahn, Soon Cheol; Kim, Bo Yeon; Kim, Min Soo; Oh, Won Keun. (Cheju Provincial Government, S.
Korea; Korea Research Institute of Bioscience and Biotechnology). Repub. Korean Kongkae Taeho Kongbo (2005), No pp. given.
CODEN: KRXXA7 KR 2005006562 A 20050117 Patent written in Korean. Application: KR 2003-46437 20030709. Priority: .

KR 2005006562 A 20050117 KR 2003-46437 20030709
flavanone
KR 2003-46437 20030709
Abstract
A method of making a compn. of citrus fruits increased in the content of a flavanone compd. by the addn. of glycosidase to citrus
fruits is provided. Therefore, the compn. contains active aglycon type flavonoids excellent in physiol. activity in large quantities and
can be effectively used as food such as functional food, health supplementary food and processing food, or feed additives. Citrus
fruits are subjected to an enzyme reaction by the addn. of 0.001 to 10% by wt. of glycosidase to citrus fruits. The enzyme reaction is
performed at 20 to 70 °C at a pH of 5 to 7 for 30 to 48h. For the optimization of the enzyme reaction, the citrus fruits are ground and
added with 1 to 10 times with distd. water. The glycosidase is selected from cellulase, hemicellulase, pectinase, xylanase,
beta-glucosidase, glucoamylase and amylase to transfer an inactive glycon flavonoid compd. to an active aglycon flavonoid compd.
The flavonoid compd. is naringenin, hesperetin, tangeretin and sinensetin.
Answer 381:
Enantiomer separation on monolithic silica HPLC columns using chemically bonded methylated and methylated/acetylated
6-O-tert-butyldimethyl-silylated β-cyclodextrin. Bayer, Mathias; Haensel, Clarissa; Mosandl, Armin. Institut fuer
Lebensmittelchemie, Biozentrum J.W. Goethe-Universitaet, Frankfurt/Main, Germany. Journal of Separation Science (2006),
29(11), 1561-1570. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: JSSCCJ ISSN: 1615-9306. Journal written in
Abstract
A new 2,3-methylated 3-monoacetylated 6-O-tert-butyldimethylsilylated β-CD deriv. was synthesized and chem. bonded onto
aminopropyl derivatized monolithic silica HPLC columns. In this CD deriv., only one of seven Me groups in 3-position was substituted
by an acetyl group. Its applicability as a chiral stationary phase for HPLC was tested and compared with exclusively 2,3-methylated
6-O-tert-butyldimethylsilylated β-CD immobilized onto aminopropyl-modified monoliths. Thirty-two chiral compds. from different chem.
classes and different functionalities were tested under RP conditions. Fourteen compds. were resolved into their enantiomers by
methylated 6-O-tert-butyldimethylsilylated β-CD. Using methylated/acetylated 6-O-tert-butyldimethylsilylated β-CD as the chiral
stationary phase 7 analytes were successfully stereodifferentiated.
Answer 382:
Liposomes containing ganglioside and trivalent chromium for lowering blood sugare and treating diabetes. Du, Shiming.
(Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 15pp. CODEN: CNXXEV CN 1813774 A
20060809 Patent written in Chinese. Application: CN 1002-3740 20050201. Priority: . CAN 145:299489 AN 2006:819613

CN 1813774 A 20060809 CN 2005-10023740 20050201
flavanone
CN 2005-10023740 20050201
Abstract
The compn. comprising ganglioside 1-60 parts, trivalent chromium ion 0.15-0.2 parts, e.g chromium picolinate, and optionally flavonoids
0.001-10000 parts, inositol 0.001-10000 parts is used for treating and prevent diabete or prepg. relevant health-care food.
Answer 383:
Transgenic plant transformed with a vector carrying aromatic hydrocarbon receptor gene AhR and its uses in detection of
environmental burden chemicals. Togami, Junichi; Okuhara, Hiroaki; Tanaka, Yoshikazu. (Suntory Limited, Japan). PCT Int.
Appl. (2006), 52pp. CODEN: PIXXD2 WO 2006085699 A1 20060817 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA,
BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU,
ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI,
NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU,
ZA. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI,
CM, GA, ML, MR, NE, SN, TD, TG. Patent written in Japanese. Application: WO 2006-JP302918 20060214. Priority: JP

WO 2006085699 A1 20060817 WO 2006-JP302918 20060214
KR, KZ, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM,
PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ,
VC, VN, YU, ZA, ZM, ZW
AU 2006213213 A1 20060817 AU 2006-213213 20060214
CA 2597742 A1 20060817 CA 2006-2597742 20060214
EP 1857550 A1 20071121 EP 2006-714059 20060214
CN 101115837 A 20080130 CN 2006-80004631 20070810
KR 2007102737 A 20071019 KR 2007-720389 20070906
JP 2005-36338 A 20050214
WO 2006-JP302918 W 20060214
flavanone
Abstract
Described is a transgenic plant transformed with a vector carrying mouse arom. hydrocarbon receptor gene AhR. The vector contains
a chimeric gene encoding for the DNA binding domain from Escherichia coli LexA, AhR, and the transactivation domain from human
herpesvirus VP16. The chimeric gene is under control of an AhR ligand stimulus-inducible promoter. The vector also contains a
nucleotide sequence encoding for dsRNA for RNA silencing of a gene involved in the synthesis of anthocyanin, for example
flavanone 3 hydroxylase gene or flavonoid 3',5' hydroxylase gene. The transgenic plant is useful in detecting an environmental
burden chem., for example dioxin and arom. hydrocarbon analogs, by observing a change in its flower color.
Answer 384:
Solid dispersion of hydrophobic bioactive comprising polymers. Buckton, Graham; Brocchini, Stephen; Fletcher, John;
Al-Obaidi, Hisham. (Pharmaterials Limited, UK). PCT Int. Appl. (2006), 37pp. CODEN: PIXXD2 WO 2006085089 A1 20060817
EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV,
LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ,
TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE,
2006-GB467 20060210. Priority: GB 2005-2790 20050210. CAN 145:218024 AN 2006:817430 CAPLUS (Copyright (C) 2008

WO 2006085089 A1 20060817 WO 2006-GB467 20060210
EP 1853225 A1 20071114 EP 2006-709705 20060210
GB 2005-2790 A 20050210
WO 2006-GB467 W 20060210
Abstract
A stable compn. of an amorphous component (such as a bioactive) and a carrier polymer is formed by mixing a bridging polymer with
the bioactive and the carrier polymer, wherein the bridging polymer is a hydrogen bond donor to both the bioactive and the carrier
polymer, thereby forming a compn. in which the bioactive and the carrier polymer have less of a tendency to crystallize than if the
flavanone
bridging polymer were not present. Thus, addn. of poly(hydroxypropyl methacrylate) (PHPMA) as a secondary component to
griseofulvin/polyvinylpyrrolidone dispersion improved the amorphous stability of griseofulvin during storage for 13 wk at 50° and 0%
relative humidity, over the griseofulvin/polyvinylpyrrolidone dispersion.
Answer 385:
Cytotoxic components in Amorpha fruticosa. Jiang, Hong; Bai, Liping; Kang, Tingguo. Liaoning College of Traditional Chinese
Medicine, Shenyang, Liaoning Province, Peop. Rep. China. Zhongcaoyao (2005), 36(10), 1469-1471. Publisher: Zhongcaoyao
Zazhi Bianjibu, CODEN: CTYAD8 ISSN: 0253-2670. Journal written in Chinese. CAN 147:5682 AN 2006:800816 CAPLUS
Abstract
The cytotoxic components in Amorpha fruticosa were extd. by 75% ethanol and Et acetate, resp. A total of five cytotoxic compds.
were obtained and they were identified as β-sitosterol (I), 5,7-dihydroxy-8-geranyl flavanone (II), tephrosin (III),
7',4-dimethoxyisoflavone (IV) an 7,2',4',5'-tetramethoxyisoflavone (V). Compds. I and IV were isolated from A. fruticosa for the first
time. In vitro cytotoxic expt. showed that Et acetate ext. had better antitumor activity.
Answer 386:
Antileukemia activity of MSFTZ-a novel flavanone analog. He, Qiaojun; Li, Runping; Fang, Liang; Ying, Huazhou; Hu, Yongzhou;
Yang, Bo. Institute of Pharmacology and Toxicology, School of Pharmaceutical Sciences, Zhejiang University, Hangzhou, Peop.
Rep. China. Anti-Cancer Drugs (2006), 17(6), 641-647. Publisher: Lippincott Williams & Wilkins, CODEN: ANTDEV ISSN:
Abstract
A newly synthesized flavanone deriv., (±)-(3aRS,4SR)-2-(2-chloro-4-methyl- sulfonylphenyl)-4'-chloro-3a,

4-diethoxy-flavane[4,3-d]-Δ1,9b-1,2,3-thiadiazoline (MSFTZ), was investigated for its antileukemia activity and mol. mechanisms.
Cytotoxicity assay confirmed the high antiproliferative efficiency of MSFTZ in six leukemia cell lines (including two drug-resistant cell
lines), with 50% inhibition of cell viability values ranging from 1.0 to 9.2 μmol/l. The results of flow cytometry assay showed that the
percentage of apoptotic HL-60 cells was 68.3% after 48 h treatment with MSFTZ, suggesting that the activation of the apoptosis
pathway was an anticancer property of MSFTZ. Furthermore, the protein changes related to apoptosis were investigated. Exposure of
HL-60 cells to MSFTZ induced pro-caspase-9 and pro-caspase-3 cleavage, X-linked inhibitor of apoptosis protein and Bcl-XL
downregulation, and poly(ADP-ribose) polymerase degrdn. Treatment of cells with MSFTZ resulted in a time-dependent redn. in
phosphorylation (activation) of extracellular signal-regulated kinase 1/2 and an increase in phosphorylation (activation) of Jun
N-terminal kinase. Taken together, our results demonstrated that activation of mitogen-activated protein kinase and apoptotic cascade
is involved in MSFTZ-induced antileukemia activity. All data suggest that MSFTZ is a promising chemotherapy drug.
Answer 387:
Microwave-Assisted Reaction of 2'-Hydroxychalcones with Hydrazides to Synthesize Flavanone Hydrazone and

4,5-Dihydropyrazole Derivatives. Nie, Aihua; Huang, Ziwei. Burnham Institute for Medical Research, La Jolla, CA, USA.
Journal of Combinatorial Chemistry (2006), 8(5), 655-658. Publisher: American Chemical Society, CODEN: JCCHFF ISSN:
flavanone
Abstract
Two distinct combinatorial libraries of flavanone hydrazones I (R1 = H, F; R2 = Ph, 4-FC6H4, 4-ClC6H4, 4-MeC6H4; R3 = 4-MeC6H4,
4-F3CC6H4, 4-pyridyl) and 4,5-dihydropyrazoles II were conveniently synthesized from the same reagents, chalcones III and arom.
hydrazides R3CONHNH2, under microwave irradn. conditions with the reaction pathway depending only on the reaction temp.
O
H
N R3 R3
N N N
R1
R1 O
R2
O R2 I OH II
R1
R2
OH III
Answer 388:
Structure-activity relationships of antimutagenic flavonoids. Mustafaev, O. N.; Abilev, S. K.; Melnik, V. A.; Tarasov, V. A.
Inst. Obshch. Genet. im. N. I. Vavilova, RAN, Russia. Ekologicheskaya Genetika (2005), 3(4), 11-18. Publisher: OOO
"IzdatelÏstvo N-L", CODEN: EGKEAE ISSN: 1811-0932. Journal written in Russian. CAN 146:352822 AN 2006:786121
Abstract
Influence of structural features of mols. on anti-mutagenic activity of flavonoids is investigated. For this purpose the new principle of
the description of dependence of biol. activity of chem. compds. from their structure is used. It is based on the use of compd.
descriptors. It is established that antimutagenic flavonoids contain C4 keto-group and double bond at positions C2 and C3, contain
hydroxyl group/s. Antimutagenic flavonoids do not have amino and nitro groups in their structures.
Answer 389:
Reduction kinetics of the free stable radical 2,2-diphenyl-1-picrylhydrazyl (DPPH.bul.) for determination of the antiradical
activity of citrus juices. Sendra, Jose M.; Sentandreu, Enrique; Navarro, Jose L. Instituto de Agroquimica y Tecnologia de
Alimentos, Valencia, Spain. European Food Research and Technology (2006), 223(5), 615-624. Publisher: Springer GmbH,
flavanone
CODEN: EFRTFO ISSN: 1438-2377. Journal written in English. CAN 145:355445 AN 2006:785531 CAPLUS (Copyright (C)
Abstract
An approxn. is made to the redn. kinetics of the stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH.bul.) by the free radical
scavenging activity of juices from sweet orange (Citrus sinensis L.), clementine (Citrus reticulata Blanco) and satsuma (Citrus unshiu
K. Marc), as well as the deduction of a kinetic equation to fit the exptl. data. This equation contains two contributions. The first
contribution accounts for the concn. of DPPH.bul. reduced by the cumulative antiradical activity of those citrus juice components that
are capable of fast hydrogen atom transfer (fast-kinetics), mainly ascorbic acid and some polyphenolic derivs.; the second accounts
for the concn. of DPPH.bul. reduced by the cumulative antiradical activity of those citrus juice components that are capable of slow
hydrogen atom transfer (slow-kinetics), mainly flavanone-7-O-glycosides and some polyphenolic derivs. This methodol. thus permits
the detn. of the total antiradical activity of a citrus juice (expressed as molar equivalents of ascorbic acid), as well as the partial
contributions of the cumulative antiradical activities (also expressed as molar equivalents of ascorbic acid) due to both fast-kinetics
and slow-kinetics.
Answer 390:
Flavonoids and Colorectal Cancer in Italy. Rossi, Marta; Negri, Eva; Talamini, Renato; Bosetti, Cristina; Parpinel, Maria;
Gnagnarella, Patrizia; Franceschi, Silvia; Dal Maso, Luigino; Montella, Maurizio; Giacosa, Attilio; La Vecchia, Carlo. Istituto di
Ricerche Farmacologiche "Mario Negri", Milan, Italy. Cancer Epidemiology, Biomarkers & Prevention (2006), 15(8), 1555-1558.
Publisher: American Association for Cancer Research, CODEN: CEBPE4 ISSN: 1055-9965. Journal written in English. CAN
Abstract
Because of their several biol. activities, flavonoids may have an important role in explaining the protective effects of vegetables,
fruit, and, possibly, tea against cancer. The potential relation between flavonoids and colorectal cancer risk was investigated using
data from a multicentric Italian case-control study, including 1,953 cases of colorectal cancers (1,225 colon cancers and 728 rectal
cancers) and 4,154 hospital controls admitted for acute nonneoplastic diseases. We have applied recently published data on the
compn. of foods and beverages, in terms of six principal classes of flavonoids, on dietary information collected through a validated
food-frequency questionnaire. Odds ratios (OR) were estd. by multiple logistic regression models, including terms for sex, age, study
center, family history of colorectal cancer, education, alc. consumption, body mass index, phys. activity, and energy intake. A
reduced risk of colorectal cancer was found for increasing intake of isoflavones (OR, 0.76, for the highest vs. the lowest quintile,
Ptrend = 0.001), anthocyanidins (OR, 0.67, Ptrend < 0.001), flavones (OR, 0.78, Ptrend = 0.004), and flavonols (OR, 0.64, Ptrend <
0.001). No significant assocn. was found for flavan-3-ols (OR, 0.98), flavanones (OR, 0.96), and total flavonoids (OR, 0.97). The
ests. did not substantially differ for colon and rectal cancers, as well as in strata of sex, age, and body mass index. The findings of
this large study provide support for an inverse assocn. of selected classes of flavonoids with colorectal cancer risk.
Answer 391:
A novel chalcone from Coreopsis tinctoria Nutt. Zhang, Yuan; Shi, Shepo; Zhao, Mingbo; Jiang, Yong; Tu, Pengfei.
Department of Natural Medicines, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing, Peop. Rep.
China. Biochemical Systematics and Ecology (2006), 34(10), 766-769. Publisher: Elsevier Ltd., CODEN: BSECBU ISSN:
flavanone
Abstract
Anal. of the dried flowers of Coreopsis tinctoria Nutt. led to the isolation and characterization of a novel compd., namely,
okanin-4'-O-β-(6''-O-malonyl)glucopyranoside (I), together with 11 known flavonoids.
OH
OH
H2 C CO O CH 2
O
O
CO 2 H OH
OH HO
OH OH O I
Answer 392:
Modulation of peroxynitrite-induced fibroblast injury by hesperetin: A role for intracellular scavenging and modulation of
ERK signalling. Pollard, Susan E.; Whiteman, Matthew; Spencer, Jeremy P. E. Molecular Nutrition Group, School of Chemistry,
Food Biosciences and Pharmacy, University of Reading, Reading, UK. Biochemical and Biophysical Research Communications
(2006), 347(4), 916-923. Publisher: Elsevier, CODEN: BBRCA9 ISSN: 0006-291X. Journal written in English. CAN 145:241649
Abstract
Peroxynitrite is thought to contribute to the progression of many diseases including cardiovascular disease, cancer, and
neurodegenerative disorders. The authors report that pretreatment of fibroblasts with the citrus flavanone, hesperetin, prior to
peroxynitrite exposure protects against peroxynitrite-mediated cytotoxicity. This protection was partially mediated by the intracellular
scavenging of peroxynitrite by hesperetin as exposure of fibroblasts to peroxynitrite following hesperetin loading led to the formation
of two intracellular nitro-hesperetin derivs. In addn., protection appeared to be mediated by hesperetin-induced changes in MAP kinase
signaling. Exposure of fibroblasts to hesperetin led to concn.-dependent increases in the phosphorylation of ERK1/2 and was obsd. to
restore peroxynitrite-mediated decreases in ERK1/2 phosphorylation. The authors propose that the protective potential of hesperetin in
fibroblasts may be mediated both by intracellular scavenging of peroxynitrite and by modulation of fibroblast signaling.
Answer 393:
Supercritical fluid extraction of antioxidant compounds from oregano. Cavero, Sofia; Garcia-Risco, Monica R.; Marin,
Francisco R.; Jaime, Laura; Santoyo, Susana; Senorans, F. Javier; Reglero, Guillermo; Ibanez, Elena. Area de Tecnologia de
Alimentos, Facultad de Ciencias, Unidad Asociada al IFI-CSI, Universidad Autonoma de Madrid, Madrid, Cantoblanco, Spain.
Journal of Supercritical Fluids (2006), 38(1), 62-69. Publisher: Elsevier B.V., CODEN: JSFLEH ISSN: 0896-8446. Journal written
Abstract
flavanone
The possibility of using oregano leaves as a new source of natural antioxidants has been investigated. Oregano leaves were extd.
using a pilot-scale SFE plant under a wide range of extg. conditions (at different extn. pressures and temps. and considering the addn.
of ethanol as modifier) with the objective of knowing not only the best extn. conditions but also the variables that control the process in
terms of extn. and fractionation of products of high antioxidant activity. The different fractions obtained at each exptl. condition
tested were characterized in terms of chem. compn. by using liq. chromatog.-diode array detection (LC-DAD) and liq. chromatog.-mass
spectrometry (LC-MS). Nine compds. have been tentatively identified as belonging to a specific family of compds. (flavone,
flavanone and flavonol); their aglycon structures have been proposed using UV spectra profile while a tentative pattern of substitution,
based on their mass spectra and mol. ion (MH+) major fragments, has been also given. Antioxidant activity was measured using 2
different in vitro assays (1,1-diphenyl-2-picrylhydrazyl (DPPH) antiradical test and bleaching β-carotene method).
Answer 394:
Methods and compositions using sirtuin modulators for treating flushing and drug-induced weight gain. Sinclair, David;
Milburn, Michael; Langer, Robert S.; Westphal, Christoph H. (Sirtris Pharmaceuticals, Inc., USA). PCT Int. Appl. (2006), 268 pp.
CODEN: PIXXD2 WO 2006079021 A2 20060727 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY,
BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE,
KG, KM, KN, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH,
PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA. Designated States
RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE,
SN, TD, TG. Patent written in English. Application: WO 2006-US2267 20060120. Priority: US 2005-645916 20050120; US

WO 2006079021 A2 20060727 WO 2006-US2267 20060120
WO 2006079021 A3 20070322
AU 2006206274 A1 20060727 AU 2006-206274 20060120
CA 2595486 A1 20060727 CA 2006-2595486 20060120
US 20060276416 A1 20061207 US 2006-336258 20060120
EP 1841415 A2 20071010 EP 2006-719216 20060120
US 2005-645916P P 20050120
US 2005-645962P P 20050121
WO 2006-US2267 W 20060120
flavanone
Abstract
The invention provides methods and compns. for treating and/or preventing flushing and/or wt. gain. The methods may comprise
modulating the activity or level of a sirtuin, such as SIRT1 or Sir2. Exemplary embodiments include methods and compns. for
counteracting drug-induced wt. gain and/or drug-induced flushing by administering a sirtuin-activating compd. Compds. of the invention
include e.g.resveratrol analogs (prepn. described).
Answer 395:
Hair conditioning composition containing flavone derivatives. Molenda, Michael; Lateulere, Magali; Golinski, Frank; Lichtl,
Rixa. (Kpss-Kao Professional Salon Services G.m.b.H., Germany). Eur. Pat. Appl. (2006), 15 pp. CODEN: EPXXDW EP
1683512 A1 20060726 Designated States R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT, IE, SI, LT, LV, FI,
RO, MK, CY, AL, TR, BG, CZ, EE, HU, PL, SK, BA, HR, IS, YU. Patent written in English. Application: EP 2004-30563 20041223.

EP 1683512 A1 20060726 EP 2004-30563 20041223
TR, BG, CZ, EE, HU, PL, SK, BA, HR, IS, YU
EP 2004-30563 20041223
Abstract
The present invention is related to a conditioning compn. for hair comprising flavone derivs. and particularly on enhanced deposition of
flavone derivs. onto hair. Accordingly, the compns. comprise at least one conditioning agent, at least one org. solvent, at least one
flavone deriv. and at least one hydroxycarboxylic and/or dicarboxylic acid and has a pH below 4.5. The conditioning compn. of the
present invention can be in the form of a shampoo, cleansing - conditioning compn., or in the form of a conditioner used after washing
hair with cleansing compns. Thus, a conditioning shampoo contained Sodium lauryl ether sulfate 11.0, coco glucoside 4.0,
cocoamidopropylbetaine 1.5, cationic polymer (Polyquaternium-10) 0.2, benzyl alc. 0.25, perfume, preservative as needed,
PEG-60-hydrogenated castor oil 0.5, PEG-18 glyceryl cocoate/oleate 2.0, t-flavanone (trans-3,4'-dimethylflavanone) 0.3, malic acid
1.00, and water to 100.0%, resp.
Answer 396:
Novel compositions for preventing and treating neurodegenerative and blood coagulation disorders. Milburn, Michael;
Milne, Jill; Westphal, Christopher H.; Normington, Karl D.; Fujii, Jennifer; Dipp, Michelle; Elliot, Peter. (Sirtris Pharmaceuticals, Inc.,
USA). PCT Int. Appl. (2006), 294 pp. CODEN: PIXXD2 WO 2006076681 A2 20060720 Designated States W: AE, AG, AL, AM,
GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ,
NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ,
flavanone
VC, VN, YU, ZA. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF,
BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2006-US1428 20060113. Priority:
US 2005-643921 20050113; US 2005-667179 20050330; US 2005-692785 20050622; US 2005-736528 20051114; US

WO 2006076681 A2 20060720 WO 2006-US1428 20060113
WO 2006076681 A3 20070628
EP, OA
AU 2006204699 A1 20060720 AU 2006-204699 20060113
CA 2595159 A1 20060720 CA 2006-2595159 20060113
US 20060276393 A1 20061207 US 2006-332056 20060113
EP 1850840 A2 20071107 EP 2006-718495 20060113
US 2005-643921P P 20050113
US 2005-667179P P 20050330
US 2005-692785P P 20050622
US 2005-736528P P 20051114
US 2005-753606P P 20051223
WO 2006-US1428 W 20060113
Abstract
Provided herein are methods and compns. for treating or preventing neurodegenerative disorders or blood coagulation disorders.
Methods may comprise modulating the activity or level of a sirtuin, such as SIRT1 or Sir2. Exemplary methods comprise contacting a
cell with a sirtuin activating compd., such as a flavone, stilbene, flavanone, isoflavone, catechin, chalcone, tannin or anthocyanidin; or
an inhibitory compd., such as nicotinamide.
Answer 397:
Flavonones and dihydroflavonols. Grayer, Renee J.; Veitch, Nigel C. Jodrell Laboratory, Royal Botanic Gardens, Kew,
flavanone
Richmond, Surrey, UK. Editor(s): Andersen, Oeyvind M.; Markham, Kenneth R. Flavonoids (2006), 917-1002. Publisher: CRC
Press LLC, Boca Raton, Fla CODEN: 69IHBV Conference; General Review written in English. CAN 146:291504 AN
Abstract
A review. A review discusses the flavanones and dihydroflavonols that have been newly reported from 1992 to 2003.
Answer 398:
Citrus flavonoids in fruit and traditional Chinese medicinal food ingredients in China. Lu, Yanhua; Zhang, Chongwei;
Bucheli, Peter; Wei, Dongzhi. State Key Laboratory of Bioreactor Engineering, New World Institute of Biotechnology, East China
University of Science and Technology, Shanghai, Peop. Rep. China. Plant Foods for Human Nutrition (New York, NY, United
States) (2006), 61(2), 57-65. Publisher: Springer, CODEN: PFHNE8 ISSN: 0921-9668. Journal written in English. CAN
Abstract
Flavonoids-enriched tissues of citrus such as peel, immature fruit and flower are consumed as culinary seasonings, tea ingredients in
China for centuries. This HPLC quant. study on the five citrus flavonoids, naringin, hesperidin, neohesperidin, sinensetin and nobiletin
on a wide range of Chinese citrus fruits and several Traditional Chinese Medicinal food ingredients in East China, revealed a great
diversity in flavonoid compn. Huyou peel (C. paradisi cv. Changshanhuyou) was found to be the best naringin (3.25%) and
neohesperidin (2.76%) source; C. aurantium, a major ingredient of several citrus-related TCM, is also a suitable source of naringin and
neohesperidin, and a good juice source for flavanone glycosides; the peel of Wenzhoumiju (C. unshiu) is one of the richest local
species in hesperidin (up to 6.25%); Zaoju (C. subcompressa) has the highest content of nobiletin (0.59%), a polymethoxylated
flavone. LC-ES-MS anal. of Zanthoxylum genus for flavonoids revealed for the first time the presence of significant amts. (0.74%) of
hesperidin in the root of Liangmianzhen (Z. nitidum (Roxb.) DC), a relative of Sichuan pepper, which is a spice widely used in China.
Answer 399:
Effect of Different Flavonoids on Collagen Synthesis in Human Fibroblasts. Stipcevic, Tamara; Piljac, Jasenka; Vanden
Berghe, Dirk. Department of Molecular Medicine, Rudjer Boskovic Institute, Zagreb, Croatia. Plant Foods for Human Nutrition
(New York, NY, United States) (2006), 61(1), 29-34. Publisher: Springer, CODEN: PFHNE8 ISSN: 0921-9668. Journal written in
Abstract
In this study, we discovered that flavonoids belonging to the subclasses: (flavanone, flavone, and flavonol) display differential
effects on the synthesis of collagen in human dermal fibroblasts. At 80 μg/mL flavonoids quercetin-3,3',4', 5,7-pentahydroxyflavone,
3-Me quercetin, and 7-hydroxyflavone significantly decreased the total protein concn. which was a direct consequence of their
cytotoxic effect, while naringenin exhibited no effect on total collagen and total protein concn. Quercetin-3,3'4',7-tetramethyl ether,
4'-hydroxyflavanone, flavanone, and fisetin significantly decreased collagen concn. while morin, rutin, and chrysin increased collagen
concn. without changing the overall protein concn. The initial screening performed in this study enables the identification of compds.
that exert significant effects on fibroblast function and show potential as starting material for pharmaceutical prepns. targeted against
various disorders centered around disturbed collagen metab.
Answer 400:
flavanone
Stimulation of melanogenesis by the citrus flavonoid naringenin in mouse B16 melanoma cells. Ohguchi, Kenji; Akao,
Yukihiro; Nozawa, Yoshinori. Gifu International Institute of Biotechnology, 1-1 Naka-Fudogaoka, Kakamigahara, Gifu, Japan.
Bioscience, Biotechnology, and Biochemistry (2006), 70(6), 1499-1501. Publisher: Japan Society for Bioscience, Biotechnology, and
Agrochemistry, CODEN: BBBIEJ ISSN: 0916-8451. Journal written in English. CAN 145:224470 AN 2006:671794 CAPLUS
Abstract
Naringenin is a naturally occurring citrus flavanone. In this study, the authors examd. the effect of naringenin on melanogenesis in
mouse B16 melanoma cells. Melanin contents and tyrosinase activities were strongly increased by naringenin. Naringenin was found
to cause marked increases in the expression levels of melanogenic enzymes.
Answer 401:
Compounds for treating hepatitis B and its pharmaceutical composition. Lee, Lien-Tzu; Chang, Hsiu-Feng; Yeh, Chun-Pang.
(The Industrial Technology Research Institute, Taiwan). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 19 pp. CODEN:

CN 1796381 A 20060705 CN 2004-10104164 20041230
CN 2004-10104164 20041230
Abstract
The structure of compd. I (R1-R5,R1'-R5'= H, methoxyl, or ethoxyl) for treating hepatitis B are presented. The compds. I are prepd.
by extg. natural plants; and/or methylation or ethylation with di-Me sulfate or di-Et sulfate. Compd. I can be fisetin Me, baicalein Me,
quercetin Me, morin Me, 7,8-dimethoxyflavone, tangeretin, naringenin Me, or flavanone.
flavanone
R' 2
R' 1 R' 3
R1
R2 O
R' 4
R' 5
R3 R5
R4 O I
Answer 402:
Cloning, functional identification and sequence analysis of flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase cDNAs
reveals independent evolution of flavonoid 3',5'-hydroxylase in the Asteraceae family. Seitz, Christian; Eder, Christian; Deiml,
Bettina; Kellner, Sandra; Martens, Stefan; Forkmann, Gert. Chair of Floriculture Crops and Horticultural Plant Breeding, Technical
University Munich, Freising, Germany. Plant Molecular Biology (2006), 61(3), 365-381. Publisher: Springer, CODEN: PMBIDB
SciFinder (R))
Abstract
Flavonoids are ubiquitous secondary plant metabolites which function as protectants against UV light and pathogens and are involved
in the attraction of pollinators as well as seed and fruit dispersers. The hydroxylation pattern of the B-ring of flavonoids is detd. by the
activity of two members of the vast and versatile cytochrome P 450 protein (P 450) family, the flavonoid 3'-hydroxylase (F3'H) and
flavonoid 3',5'-hydroxylase (F3'5'H). Phylogenetic anal. of known sequences of F3'H and F3'5'H indicated that F3'5'H was recruited
from F3'H before the divergence of angiosperms and gymnosperms. Seven cDNAs were isolated from species of the Asteraceae
family, all of which were predicted to code for F3'Hs based on their sequences. The recombinant proteins of four of the
heterologously in yeast expressed cDNAs exhibited the expected F3'H activity but surprisingly, three recombinant proteins showed
F3'5'H activity. Phylogenetic analyses indicated the independent evolution of an Asteraceae-specific F3'5'H. Furthermore, sequence
anal. of these unusual F3'5'H cDNAs revealed an elevated rate of nonsynonymous substitutions as typically found for duplicated
genes acquiring new functions. Since F3'5'H is necessary for the synthesis of 3',4',5'-hydroxylated delphinidin-derivs., which normally
provide the basis for purple to blue flower colors, the evolution of an Asteraceae-specific F3'5'H probably reflects the adaptive value
of efficient attraction of insect pollinators.
Answer 403:
Preparation of benzopyrano[4,3-d][1,2,3]thiadiazoline derivatives as antitumor agents. Hu, Yongzhou; Ying, Huazhou; He,
Qiaojun; Yang, Bo. (Zhejiang University, Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 27 pp.
CODEN: CNXXEV CN 1793148 A 20060628 Patent written in Chinese. Application: CN 1009-7012 20051231. Priority: . CAN

flavanone

CN 1793148 A 20060628 CN 2005-10097012 20051231
CN 2005-10097012 20051231
Abstract
The title benzopyrano[4,3-d][1,2,3]thiadiazoline derivs. I [wherein R1 = independently H, Cl, OMe, or Me; R2 = independently H, Cl,
OMe, Me, or OCH2O; R3 = NO2, SO2Me, or NHC(=O)Me; R4 = Me, Et, Pr, or iso-Pr] were prepd. as antitumor agents (no data). For
example, II was prepd. in a multi-step synthesis. II showed antitumor activity with IC50 of 1.59 μg/mL against PC-3 human prostatic
tumor cell.
R2
R2 R2 Cl
R1
OR 4 OEt
R1 O O
R2
OR 4 OEt
R2
R1 S Me S
R1 N N Cl N N Cl
R3 I HN COCH 3 II
Answer 404:
Solvent-free synthesis of flavanones over aminopropyl-functionalized SBA-15. Wang, Xueguang; Cheng, Soofin.
Department of Chemistry, National Taiwan University, Taipei, Taiwan. Catalysis Communications (2006), 7(9), 689-695.
Publisher: Elsevier B.V., CODEN: CCAOAC ISSN: 1566-7367. Journal written in English. CAN 146:316646 AN 2006:625429
Abstract
Flavanone was synthesized through the Claisen-Schmidt condensation between benzaldehyde and acetophenone and subsequent
intramol. Michael addn. over aminopropyl-functionalized SBA-15 materials. The catalysts with well-ordered hexagonally arranged
mesopores were synthesized by one-pot co-condensation of tetraethoxysilane and aminopropyltriethoxysilane using amphiphilic block
copolymer as the template under acidic condition. The results showed that the catalysts had good activities and very high selectivities
to flavanone in solvent-free condition, while the use of org. solvents decreased the catalytic activities and flavanone selectivities.
The influence of substituents in the arom. rings of benzaldehyde and 2'-hydroxyacetophenone was also investigated under the
flavanone
solvent-free condition.
Answer 405:
Excited state acidity of bifunctional compounds 9. Excited state intramolecular proton transfer in
3,5-dihydroxy-7,4'-dimethoxyflavone and 3,5-dihydroxy-7,4'-dimethoxyflavanone: spectral and fluorescence decay results.
Portugal, Samira G. M.; Montero-Cabrera, Luis A.; Diaz, Lourdes A.; Brinn, Ira M. Laboratorio de Espectroscopia Resolvida no Tempo
(LERT), Instituto de Quimica, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil. Journal of Photochemistry and
Photobiology, A: Chemistry (2006), 181(2-3), 370-377. Publisher: Elsevier B.V., CODEN: JPPCEJ ISSN: 1010-6030. Journal
Abstract
Both title compds. show two fluorescence bands, with maxima at approx. 290 nm and 340 nm in non-protic (hexane, cyclohexane) and
protic (ethanol) solvents. Approx. MO calcns. suggest that these two bands can be assocd. with an excitation partially localized on the
anisolyl moiety and a more delocalized excitation, resp., present in both compds. In cyclohexane both compds. exhibit a fluorescence
band with a max. at 550 nm, which can be assocd. with the proton transferred species. In the case of the flavanone this band is very
weak and attributed to Excited State Intramol. Proton Transfer (ESIPT) of the proton at the 5-position. In the flavone the corresponding
band is considerably more intense and the theor. calcns. point to the proton being transferred as originating from the 5-position also. In
cyclohexane the flavanone exhibits monoexponential decay under the band at 290 nm. In all other combinations solute/solvent/band
studied here the fluorescence was found to follow a biexponential decay. In the case of the flavanone these results are interpreted as
indicating that the localized anisolyl excitation is not coupled to the delocalized excitation, whereas the decay of the latter is coupled to
ESIPT. The time-resolved results of the flavone are interpreted as indicating coupling between all three excited states obsd.
Answer 406:
Effect of Silibinin on the Growth and Progression of Primary Lung Tumors in Mice. Singh, Rana P.; Deep, Gagan;
Chittezhath, Manesh; Kaur, Manjinder; Dwyer-Nield, Lori D.; Malkinson, Alvin M.; Agarwal, Rajesh. Department of Pharmaceutical
Sciences, School of Pharmacy, University of Colorado Health Sciences Center, Denver, CO, USA. Journal of the National
Cancer Institute (2006), 98(12), 846-855. Publisher: Oxford University Press, CODEN: JNCIEQ ISSN: 0027-8874. Journal written
Abstract
Background: Silibinin, a flavanone from milk thistle, inhibits the growth of tumors in several rodent models. We examd. the effects of
dietary silibinin on the growth, progression, and angiogenesis of urethane-induced lung tumors in mice. Methods: A/J mice (15 per
group) were injected with urethane (1 mg/g body wt.) or saline alone and fed normal diets for 2 wk, after which they were fed diets
contg. different doses of silibinin (0%-1% [wt/wt] silibinin) for 18 or 27 wk. Immunohistochem. and Western blot anal. were used to
examine angiogenesis and enzymic markers of inflammation, proliferation, and apoptosis. All statistical tests were two-sided. Results:
Urethane-injected mice exposed to silibinin had statistically significantly lower lung tumor multiplicities than urethane-injected mice fed
the control diet lacking silibinin (i.e., control mice). Mice that received urethane and 1% (wt/wt) dietary silibinin for 18 wk had 93% fewer
large (i.e., 1.5-2.5-mm-diam.) lung tumors than control mice (mean no. of tumors/mouse: 27 in the urethane group vs. 2 in the urethane
+ 1% silibinin group, difference = 25 tumors/mouse, 95% confidence interval [CI] = 13 to 37 tumors/mouse, P = .005). Lung tumors of
silibinin-fed mice had 41%-74% fewer cells pos. for the cell proliferation markers proliferating cell nuclear antigen and cyclin D1 than
lung tumors of control mice. Tumor microvessel d. was reduced by up to 89% with silibinin treatment (e.g., 56 microvessels/400× field
in tumors from control mice vs. 6 microvessels/400× field in tumors from urethane + 1% silibinin-treated mice [difference = 50
microvessels/400× field, 95% CI = 46 to 54 microvessels/400× field; P<.001]). Silibinin decreased lung tumor expression of vascular
flavanone
endothelial growth factor (VEGF) and of inducible nitric oxide synthase and cyclooxygenase-2, two enzymes that promote lung tumor
growth and progression by inducing VEGF expression.
Conclusions: Silibinin inhibits lung tumor angiogenesis in an animal model and merits investigation as a chemopreventive
agent for suppressing lung cancer progression.
Answer 407:
A new geranyl flavanone from Macaranga triloba. Dinh, Vinh; Zhang, Hua-Ping; Duc, Nguyen Minh; Tuu, Nguyen Viet; Qin,
Guo-Wei. Faculty of Pharmacy, Ho Chi Minh City College of Pharmacy and Medicine, Ho ChiMinh City, Vietnam. Journal of
Asian Natural Products Research (2005), Volume Date 2006, 8(1-2), 155-158. Publisher: Taylor & Francis Ltd., CODEN: JANRFI
SciFinder (R))
Abstract
A new geranyl flavanone, 2'-hydroxy-macarangaflavone A (I), and a known 4',7-dihydroxy-8-methylflavan were isolated from the
leaves of Macaranga triloba (Euphorbiceae). The structure of I was elucidated based on spectroscopic methods, including 1D and 2D
NMR anal.
Me
Me
Me
HO OH
HO O
OH O I
Answer 408:
Structure-activity relations of inhibitory effects of various flavonoids on lipopolysaccharide-induced prostaglandin E2

production in rat peritoneal macrophages: comparison between subclasses of flavonoids. Takano-Ishikawa, Y.; Goto, M.;
Yamaki, K. National Food Research Institute, Kannondai, Tsukuba, Ibaraki, Japan. Phytomedicine (2006), 13(5), 310-317.
Publisher: Elsevier GmbH, CODEN: PYTOEY ISSN: 0944-7113. Journal written in English. CAN 145:448573 AN 2006:616708
Abstract
A study of the structure-activity relations of the inhibitory effect of flavonoids on lipopolysaccharide (LPS)-induced prostaglandin
flavanone
prodn. was carried out via a comparative examn. of 39 flavonoids and related compds. A comparison of the subclasses showed that
flavones were most effective, followed by flavanones. Flavonols were less effective than those two groups. These results suggest
that the C2-C3 double-bond and 4-oxo functional group of the C-ring are important factors for the high inhibition activities. Flavonoids
showed the strongest inhibitory effect on the expression of Cox-2 protein. These results help to explain part of the reason for the
pharmacol. efficacy of flavonoids as anti-inflammatory compds.
Answer 409:
Cloning and characterization of a flavanone 3-hydroxylase gene from Ginkgo biloba. Shen, Guoan; Pang, Yongzhen; Wu,
Weisheng; Deng, Zhongxiang; Zhao, Lingxia; Cao, Youfang; Sun, Xiaofen; Tang, Kexuan. Shanghai Key Laboratory of
Biotechnology, Plant Biotechnology Research Center, Fudan-SJTU-Nottingham Plant Biotechnology R&D Center, School of Agriculture
and Biology, Shanghai Jiao Tong University, Shanghai, Peop. Rep. China. Bioscience Reports (2006), 26(1), 19-29. Publisher:
Springer, CODEN: BRPTDT ISSN: 0144-8463. Journal written in English. CAN 145:242592 AN 2006:587712 CAPLUS
Abstract
Flavanone 3-hydroxylase (F3H) activity is necessary for the biosynthesis of flavonoids, the main ingredients of Gingko biloba ext.
The full-length cDNA and genomic DNA sequences of F3H gene were isolated from G. biloba for the first time. The full-length cDNA
of G. biloba F3H gene (designated as GbF3H) contained a 1071-bp open reading frame (ORF) encoding a 357-amino-acid protein with a
calcd. mol. wt. of about 40 kDa and isoelec. point (pI) of 5.57. Genomic DNA anal. showed that GbF3H gene has 3 exons and 2
introns. The deduced GbF3H protein showed high identities to other plant F3Hs. The conserved amino acids ligating ferrous iron and
residues participating in 2-oxoglutarate binding (R-X-S) were found in GbF3H at the similar positions like other F3Hs. Three-dimensional
structure modeling showed that GbF3H had a jerry roll in the enzyme core consisted of β-sheet, a typical structure shared by all
2-oxoglutarate-dependent dioxygenases including F3Hs. Phylogenetic tree anal. revealed that GbF3H shared the same ancestor in
evolution with other F3Hs and had a further relationship with other angiosperms species. Southern blot anal. indicated that GbF3H
belonged to a multi-gene family. Transcription anal. revealed that GbF3H expressed in stem and leaf with the highest transcription
level in leaf. The isolation and characterization of GbF3H gene will be helpful to further study the role of GbF3H gene in the
biosynthesis of flavonoids in G. biloba.
Answer 410:
Antibacterial activity of propolis and its active principles alone and in combination with macrolides, beta-lactams and
fluoroquinolones against microorganisms responsible for respiratory infections. Speciale, A.; Costanzo, R.; Puglisi, S.;
Musumeci, R.; Catania, M. R.; Caccamo, F.; Iauk, L. Department of Microbiological and Gynecological Sciences, University of
Catania, Italy. Journal of Chemotherapy (Firenze, Italy) (2006), 18(2), 164-171. Publisher: E.S.I.F.T. srl, CODEN: JCHEEU
ISSN: 1120-009X. Journal written in English. CAN 146:96648 AN 2006:581258 CAPLUS (Copyright (C) 2008 ACS on SciFinder
(R))
Abstract
Propolis is produced by bees and is reported to have several pharmaceutical properties. Its antibacterial activity against strains
causing upper respiratory tract infections is particularly important: propolis might be used as a therapeutic agent to prevent the
bacterial infections that sometimes overlap viral infections. In this study the in vitro activity of both an alc. soln. and a hydroglyceric
ext. of propolis, as well as its active principles, was tested against bacteria responsible for respiratory infections (Streptococcus
pneumoniae, Haemophilus influenzae, Haemophilus parainfluenzae, Moraxella catarrhalis and Streptococcus pyogenes). We also
evaluated the in vitro activity of a combination of propolis and its active principles and some beta-lactams, macrolides and
flavanone
fluoroquinolones. Our results, though not demonstrating a clearly synergistic activity between antibiotics and propolis and its
constituents, show the possibility of using natural prepns., due to their antimicrobial and anti-inflammatory properties, to enhance
antibacterial therapy.
Answer 411:
Antioxidant activity with flavonoidal constituents from Aerva persica. Ahmed, Ejaz; Imran, Muhammad; Malik, Abdul; Ashraf,
Muhammad. International Center for Chemical Sciences, H.E.J. Research Institute of Chemistry, University of Karachi, Karachi,
Pak. Archives of Pharmacal Research (2006), 29(5), 343-347. Publisher: Pharmaceutical Society of Korea, CODEN: APHRDQ
SciFinder (R))
Abstract
A new flavanone Persinol (1) and the new flavanone glucosides persinosides A (2) and B (3), along with known flavonoids (4 and 5)
have been isolated from the Et acetate sol. fraction of the whole plants of Aerva persica. Their structures were elucidated on the basis
of extensive anal. of NMR (1D & 2D-NMR) spectral data. All of them showed profound antioxidative activities by DPPH and
cytochrome-c-redn. assays using the HL-60 cell culture system.
Answer 412:
Multi-parallel chiral screening: screening of chiral stationary and mobile phases for method development of preparative
separations. Francotte, Eric; Huynh, Dan; Wetli, Herbert A. Discovery Technologies, Novartis Institutes for BioMedical
Research, Basel, Switz. G.I.T. Laboratory Journal, Europe (2006), 10(3), 46-48. Publisher: GIT Verlag GmbH & Co. KG, CODEN:
GLJEAW ISSN: 1611-6038. Journal written in English. CAN 146:213033 AN 2006:551088 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
A fast and automated chiral sepn. screening platform was developed, allowing the parallel and simultaneous testing of eight different
chiral columns with a broad variety of mobile phases within a short period of time. In particular for preparative applications, this
approach considerably accelerates the method development of chiral sepns., leading to a significant gain of time and productivity.
Answer 413:
Synthesis and immunosuppressive activity of L-rhamnopyranosyl flavonoids. Yang, Xiaoliang; Sun, Yang; Xu, Qiang; Guo,
Zijian. Department of Chemistry, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, Peop. Rep.
China. Organic & Biomolecular Chemistry (2006), 4(12), 2483-2491. Publisher: Royal Society of Chemistry, CODEN: OBCRAK
SciFinder (R))
Abstract
flavanone
Astilbin, a flavonoid isolated from different plants, shows diverse biol. activities. Synthesis and immunosuppressive activity of seven
analogs of astilbin are reported, which may shed light on the structure-activity relationship of the compds. The following glycosyl
flavonoids, 6-α-L-rhamnopyranosyloxyflavanone (I), 3-α-L-rhamnopyranosyloxyflavone (II), 3-α-l-rhamnopyranosyloxyflavanone (III),
3-α-L-rhamnopyranosyloxychromanone (IV), 4-α-L-rhamnopyranosyloxychromanol (V),
7-hydroxy-3-α-L-rhamnopyranosyloxyflavanone (VI) and 4'-hydroxy-3-α-L-rhamnopyranosyloxyflavanone (VII) were prepd. resp. by
glycosylation of 6-hydroxyflavanone, 3-hydroxyflavone, 3-hydroxyflavanone, 3-hydroxychromanone, 4-chromanol,
7-benzyloxy-3-hydroxyflavanone, 4'-benzyloxy-3-hydroxyflavanone. Similar to astilbin, II, III, IV, VI and VII significantly inhibited the
single mixed lymphocytes reaction (sMLR) and enhanced the apoptosis of spleen cells isolated from mice with sheep red blood
cell-induced delayed-type hypersensitivity resp. However, I only showed a slight tendency to inhibit sMLR at higher concn. Both
compds. I and V did not influence the cell apoptosis. These data suggest that the position at which the sugar is linked to the flavone
and the presence of carbonyl on C-4 and phenol hydroxyl group in A or B ring play essential roles in detg. the biol. activity of the
flavonoids. However, the presence of a B ring is unfavorable for the biol. activity and the double bond at C(2)-C(3) in C-ring shows
little effect on the activity.
Answer 414:
Radioprotective effects of hesperidin against gamma irradiation in mouse bone marrow cells. Hosseinimehr, S. J.; Nemati,
A. Department of Medicinal Chemistry, Faculty of Pharmacy, Mazandarn University Medical Sciences, Sari, Iran. British Journal
of Radiology (2006), 79(941), 415-418. Publisher: British Institute of Radiology, CODEN: BJRAAP ISSN: 0007-1285. Journal
Abstract
The radioprotective effects of hesperidin (HES), a flavanone glucoside, were investigated by using the micronucleus test for
anticlastogenic and cell proliferation activity. A single i.p. (i.p.) administration of hesperidin at doses of 10 mg kg-1, 20 mg kg-1, 40
mg kg-1, 80 mg kg-1 and 160 mg kg-1 45 min prior to gamma irradn. (2 Gy) reduced the frequencies of micronuleated polychromatic
erythrocytes (MnPCEs). All five doses of HES significantly reduced the frequencies of MnPCEs and increased PCE/PCE+NCE ratio
in mice bone marrow compared with non-drug-treated irradiated control (p<0.0001). There was a drug dose-response effect of HES in
reducing MnPCE and increasing the PCE/PCE+NCE ratio in bone marrow cells. The max. redn. in MnPCE was obsd. in mice treated
with HES at a dose of 80 mg kg-1. The total MnPCE values were 2.85 fold less in the 80 mg kg-1 HES group after being exposed to 2
Gy of γ-rays than those in the resp. irradiated control. Our study demonstrates that hesperidin has powerful protective effects on the
radiation-induced DNA damage and on the decline in cell proliferation in mouse bone marrow.
Answer 415:
Antiproliferative activity of several phenolic compounds against melanoma cell lines: relationship between structure and
activity. Benavente-Garcia, Obdulio; Castillo, J.; Lorente, J.; Alcaraz, M.; Yanez, J.; Martinez, C.; Vicente, V.; Lozano, J. A.
Research and Development Department, Nutrafur-Furfural Espanol S.A. Camino Viejo de Pliego, Murcia, Spain. Agro Food
Industry Hi-Tech (2005), 16(4), 30-34. Publisher: Tekno Scienze srl, CODEN: AIHTEI ISSN: 1722-6996. Journal written in English.
Abstract
Polyphenolic compds. are widely distributed in the vegetable kingdom and are therefore consumed regularly in the human diet.
Epidemiol. studies suggest that foods rich in polyphenolic compds. contribute to reducing the risk of cancer. We study the possible
cytotoxicity and antiproliferative effects in vitro of twelve phenolic compds. on three cell lines of melanocytes, two of melanoma
(B16F10 and SK-MEL-1) and one of non-transformed melanocytes (Melan-a) and identify the possible relationship between the chem.
flavanone
structure of the tested compds. and their effect on cellular viability. The said phenolic compds. corresponded to eight flavonoids with
varying hydroxyl and methoxyl substituents, related structurally through the oxidn. state of their flavonoid skeleton, and four phenolic
acids. The cytotoxic activity of all the studied compds. was modest or not apparent. The flavonoids, luteolin, tangeretin, baicalein,
quercetin and myricetin, and gallic acid showed antiproliferative effects on the tested lines. Our results suggest that a correlation
exists between the structural oxidn. state and the position, no. and nature of substituents of the polyphenolic compds. studied and their
antiproliferative effects.
Answer 416:
Screening for inhibitors of 2-oxoglutarate-dependent dioxygenases: Flavanone 3β-hydroxylase and flavonol synthase.
Halbwirth, Heidrun; Fischer, Thilo C.; Schlangen, Karin; Rademacher, Wilhelm; Schleifer, Klaus-Juergen; Forkmann, Gert; Stich, Karl.
Institut fuer Verfahrenstechnik, Umwelttechnik und Technische Biowissenschaften, Technische Universitaet Wien, Vienna, Austria.
Plant Science (Amsterdam, Netherlands) (2006), 171(2), 194-205. Publisher: Elsevier B.V., CODEN: PLSCE4 ISSN: 0168-9452.
Abstract
2-Oxoglutarate-dependent dioxygenases (2-ODDs) catalyze numerous steps in biosynthetic pathways of plants. Prohexadione-Ca is a
known inhibitor of such reactions, due to its structural similarity to 2-oxoglutarate. In apple (Malus domestica) and pear (Pyrus
communis) leaves, the transient inhibition of 2-ODDs flavanone 3β-hydroxylase (FHT) and flavonol synthase (FLS) by
prohexadione-Ca results in distinct changes in the flavonoid spectrum, which are responsible for an enhanced resistance against two
major pome fruit diseases, fire blight (caused by Erwinia amylovora) and apple scab (caused by Venturia inaequalis). We used
recombinant apple and pear FHT and apple FLS for screening 23 structural analogs of 2-oxoglutarate, mostly cyclohexanediones,
pyridine dicarboxylic acids and N-heterocycles with carbonyl functions for other dioxygenase inhibitors. Activations, which were also
obsd. for some compds., are interpreted as in vitro effects due to Fe2+-chelating ability. Apart from structural similarity to
2-oxoglutarate, close structural similarity of cyclohexanediones and some pyridine dicarboxylic acids to flavonoid substrates was
identified. Beyond the competitive inhibition for the co-substrate 2-oxoglutarate, flavonoid converting 2-ODDs may also be inhibited at
the substrate binding site by these inhibitors. All compds. found to be active as inhibitors may prove useful for studying the reaction
mechanisms and substrate specificities of various 2-ODDs.
Answer 417:
Effect of t-flavanone on hair growth. Hotta, Mitsuyuki; Imokawa, Genji. Lab. of Biosciences, Kao Corp., Japan. Anchi -
Eijingu Shirizu (2005), 1(Shiraga, Datsumo, Ikumo no Jissai), 105-116. Publisher: Enu - Ti - Esu, CODEN: AESNBO Journal;
General Review written in Japanese. CAN 146:189863 AN 2006:529276 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
A review. The development of a hair growth stimulant trans-3,4'-Dimethyl-3-hydroxyflavanone (t-flavanone) by modification of a hair
growth-stimulating component in Hypericum perforatum ext. (astilbin), and the clin. trials of t-flavanone in male patients with alopecia
are discussed in this article.
Answer 418:
flavanone
Isolation and structure elucidation of glycosides in n-butanol extracts from rhizome of Periploca calophylla. Guo, Hongli;
Zhou, Jinyun. Institute of Materia Medica, Chinese Academy of Medical Sciences + Peking Union Medical College, Beijing, Peop.
Rep. China. Zhongguo Zhongyao Zazhi (2005), 30(1), 44-46. Publisher: Zhongguo Zhongyao Zazhishe, CODEN: ZZZAE3 ISSN:
Abstract
The isolation and structure elucidation of glycosides in n- butanol exts. from rhizome of Periploca calophylla were studied. The chem.
constituents from n-butanol exts. of Periploca calophylla were isolated and purified by chromatog. technol. and their structures were
elucidated on the basis of physicochem. property and spectroscopic methods. Eight glycosides were isolated and identified as
periplocin, kaempferol 3-α-D-arabinoside, kaempferol 3-O-β-D-glucoside,
3',4',5,7-tetrahydroxy-flavanone-2(S)-3'-O-β-D-glucopyranoside, (+)-syringaresinol-4'-O-β-D-monoglucoside, 1-sinapoylglucoside,
erigeside C, 2,6-dimethoxy-4-hydroxyphenol 1-O-β-D-glucoside. All the compds. were isolated first time from Periploca calophylla
Falc.
Answer 419:
Central nervous system depressant action of flavonoid glycosides. Fernandez, Sebastian P.; Wasowski, Cristina; Loscalzo,
Leonardo M.; Granger, Renee E.; Johnston, Graham A. R.; Paladini, Alejandro C.; Marder, Mariel. Instituto de Quimica y
Fisicoquimica Biologicas, Facultad de Farmacia y Bioquimica, Buenos Aires, Argent. European Journal of Pharmacology (2006),
539(3), 168-176. Publisher: Elsevier B.V., CODEN: EJPHAZ ISSN: 0014-2999. Journal written in English. CAN 145:159619 AN
Abstract
The pharmacol. effects on the central nervous system (CNS) of a range of available flavonoid glycosides were explored and
compared to those of the glycosides 2S-hesperidin and linarin, recently isolated from valeriana. The glycosides 2S-neohesperidin,
2S-naringin, diosmin, gossypin and rutin exerted a depressant action on the CNS of mice following i.p. injection, similar to that found
with 2S-hesperidin and linarin. We demonstrate in this work that these behavioral actions, as measured in the hole board, thiopental
induced sleeping time and locomotor activity tests, are unlikely to involve a direct action on γ-aminobutyric acid type A (GABAA)
receptors. The corresponding aglycons were inactive, pointing to the importance of the sugar moieties in the glycosides in their CNS
depressant action following systemic administration. The pharmacol. properties of the flavonoid glycosides studied here, in addn. to
our previous results with hesperidin and linarin, opens a promising new avenue of research in the field.
Answer 420:
Isolation and in vitro antibacterial activity of astilbin, the bioactive flavanone from the leaves of Harungana
madagascariensis Lam. ex Poir. (Hypericaceae). Moulari, B.; Pellequer, Y.; Lboutounne, H.; Girard, C.; Chaumont, J.-P.; Millet,
J.; Muyard, F. Laboratoire de Galenique et Biopharmacie, EA-3924 Sciences Separatives et Biopharmaceutiques, UFR Sciences
Medicales et Pharmaceutiques, Universite de Franche-Comte, Besancon, Fr. Journal of Ethnopharmacology (2006), 106(2),
272-278. Publisher: Elsevier B.V., CODEN: JOETD7 ISSN: 0378-8741. Journal written in English. CAN 146:117912 AN
Abstract
Harungana madagascariensis is well known for its topical antibacterial properties used in the elaboration of a lot of skin hygiene
flavanone
products. The aim of this study was, on the one hand, to evaluate the in vitro antibacterial activities of aq., ethanolic and Et acetate
crude exts. of Harungana madagascariensis leaves against bacterial strains representative of skin microflora and, on the other hand,
to det. the chem. structure of the active compd. Only the Et acetate leaf ext. presented important antibacterial activity. Its
fractionation was carried out by column chromatog. using silica gel 60 and it yielded 11 fractions. A bioautog. method, revealed in
these fractions the presence of a flavanone as the active compd. astilbin or 3-O-α-L-rhamnoside-5,7,3',4'-tetrahydroxydihydroflavonol
which was identified on the basis of its spectroscopic data. Concerning the antibacterial activity against the representative skin
microflora of the armpit and feet, MIC and MBC ranged from 25 to 250 and 100 to 750 μg ml-1, resp. The results showed that some
bacteria considered to be responsible for bad odours at the armpit and feet levels, were destroyed at 200 μg ml-1 (MBC), a concn.
sparing most of the useful saprophytic microflora. The minimal inhibitory quantity (MIQs) of astilbin ranged from 50 to 100 μg.
Answer 421:
Combinatorial biosynthesis of flavones and flavonols in Escherichia coli. Miyahisa, Ikuo; Funa, Nobutaka; Ohnishi, Yasuo;
Martens, Stefan; Moriguchi, Takaya; Horinouchi, Sueharu. Department of Biotechnology, Graduate School of Agriculture and Life
Sciences, The University of Tokyo, Bunkyo-ku, Tokyo, Japan. Applied Microbiology and Biotechnology (2006), 71(1), 53-58.
Publisher: Springer, CODEN: AMBIDG ISSN: 0175-7598. Journal written in English. CAN 145:247558 AN 2006:511679
Abstract
(2S)-Flavanones (naringenin and pinocembrin) are key intermediates in the flavonoid biosynthetic pathway in plants. Recombinant
Escherichia coli cells contg. four genes for a phenylalanine ammonia-lyase, cinnamate/coumarate:CoA ligase, chalcone synthase, and
chalcone isomerase, in addn. to the acetyl-CoA carboxylase, have been established for efficient prodn. of naringenin from tyrosine
and pinocembrin from phenylalanine. Further introduction of the flavone synthase I gene from Petroselinum crispum under the control
of the T7 promoter and the synthetic ribosome-binding sequence in pACYCDuet-1 caused the E. coli cells to produce flavones:
apigenin (13 mg/l) from tyrosine and chrysin (9.4 mg/l) from phenylalanine. Introduction into the E. coli cells of the flavanone
3β-hydroxylase and flavonol synthase genes from the plant Citrus species led to prodn. of flavonols: kaempferol (15.1 mg/l) from
tyrosine and galangin (1.1 mg/l) from phenylalanine. The combinatorial biosynthesis of the flavones and flavonols in E. coli is
promising for the construction of a library of various flavonoid compds. and un-natural flavonoids in bacteria.
Answer 422:
Influence of naringenin on oxytetracycline mediated oxidative damage in rat liver. Pari, Leelavinothan; Gnanasoundari,
Muthurangam. Department of Biochemistry, Faculty of Science, Annamalai University, Annamalainagar, India. Basic & Clinical
Pharmacology & Toxicology (2006), 98(5), 456-461. Publisher: Blackwell Publishing Ltd., CODEN: BCPTBO ISSN: 1742-7835.
Abstract
Naringenin is a naturally occurring citrus flavanone, which has been reported to have a wide range of pharmacol. properties. The
present work was carried out to evaluate the effect of naringenin on antioxidant and lipid peroxidn. status in the liver of
oxytetracycline-intoxicated rats. Intraperitonial administration of oxytetracycline 200 mg/kg for 15 days resulted in a significant
elevation in serum hepatospecific markers such as aspartate transaminase, alanine transaminase, alk. phosphatase, lactate
dehydrogenase, and bilirubin and the levels of lipid peroxidn. markers [thiobarbituric acid-reactive substances (TBARS) and lipid
hydroperoxides] in liver. Oxytetracycline also caused a significant redn. in the activities of superoxide dismutase, catalase,
glutathione peroxidase, reduced glutathione (GSH), vitamin C, and vitamin E in liver. Oral administration of naringenin (50 mg/kg
b.w.t.) with oxytetracycline significantly decreased the activities of serum aspartate transaminase, alanine transaminase, alk.
flavanone
phosphatase, lactate dehydrogenase, and the levels of bilirubin along with a significant decrease in the levels of lipid peroxidn. markers
in the liver. In addn., naringenin significantly increased the activities of superoxide dismutase, catalase, and GSH peroxidase as well
as the level of GSH, vitamin C, and vitamin E in the liver of the oxytetracycline-treated rats. Thus, naringenin exhibited an antioxidant
property and decreased the lipid peroxidn. against oxytetracycline-induced oxidative stress in the liver.
Answer 423:
Relationship between structures and cytotoxicities of flavone derivatives against HIV with quantum-chemical descriptors.
Du, Juan; Li, Zerong; Li, Xiangyuan; Yang, Shengyong. College of Chemical Engineering, Sichuan University, Sichuan, Peop. Rep.
China. Huaxi Yaoxue Zazhi (2005), 20(2), 95-98. Publisher: Huaxi Yike Daxue Yaoxueyuan, CODEN: HYZAE2 ISSN:
Abstract
The quant. relationship between structures and cytotoxicities of 33 flavone derivs. against HIV was studied. 14 Quantum-chem.
descriptors were calcd. at B3LYP/6- 31G** level. A total of 5 important descriptors was selected by stepwise regression anal. (SRA).
These descriptors were: energy of the lowest occupied mol. orbit (ELUMO), mol. hardness (η), mol. polarizalsility (α), mol. dipole
moment (μ), and net charge on the seventh C atom (Q7). A leave-one-out cross-validation method was used to select the no. of latent
variables for the building of the QSAR models by principal component regression (PCR) and partial least square regression (PLS)
method. resp. The cross-validation squared correlation coeffs. Rcv2 were 0.70 for PCR and 0.74 for PLS, showing that both of these
two models had good prediction ability and the PLS model was superior to the PCR model. The QSAR model shows the effects of the
five descriptors, and directs the research of the flavonoids with low toxicity.
Answer 424:
Effect of t-flavanone on hair growth. Moriwaki, Shigeru. Biological Science Laboratories, Kao Corporation, Haga, Tochigi,
Japan. Nippon Koshohin Gakkaishi (2006), 30(1), 23-28. Publisher: Nippon Koshohin Gakkai, CODEN: NKGIBW ISSN:
1880-2532. Journal; General Review written in Japanese. CAN 145:459902 AN 2006:505547 CAPLUS (Copyright (C) 2008
Abstract
A review. In 1998 the domestic market for hair growth agent was about 30 billion yen in Japan. The market's growth spurt was set off
by the launch of RiUP, which is a hair growth stimulant hit shelves in 1999. The market has been sliding down since its peak of 60
billion yen. The recent market research ests. that more than 8 million men in Japan suffer some degree of hair loss. Industry sources
est. the size of the market will grow again due to the marketing of powerful products, such as Propecia, which was launched in Dec.
2005 as the first oral medication for androgenic alopecia. Accordingly, a great amt. of R&D effort in cosmetic, pharmaceutical, and
bio-venture industries centers on developing a hair growth agent with higher efficacy. This paper aims to outline the mechanism of
action of chief ingredients for hair growth agents on the market, and to explain the mechanism and efficacy of t-flavanone with
detailed information.
Answer 425:
Use of ecotilling as an efficient SNP discovery tool to survey genetic variation in wild populations of Populus trichocarpa.
flavanone
Gilchrist, Erin J.; Haughn, George W.; Ying, Cheng C.; Otto, Sarah P.; Zhuang, Jun; Cheung, Dorothy; Hamberger, Bjorn; Aboutorabi,
Fariba; Kalynyak, Tatyana; Johnson, Lee; Bohlmann, Joerg; Ellis, Brian E.; Douglas, Carl J.; Cronk, Quentin C. B. Department of
Botany, University of British Columbia, Vancouver, BC, Can. Molecular Ecology (2006), 15(5), 1367-1378. Publisher: Blackwell
Publishing Ltd., CODEN: MOECEO ISSN: 0962-1083. Journal written in English. CAN 146:39536 AN 2006:498630 CAPLUS
Abstract
Ecotilling was used as a simple nucleotide polymorphism (SNP) discovery tool to examine DNA variation in natural populations of the
western black cottonwood, Populus trichocarpa, and was found to be more efficient than sequencing for large-scale studies of genetic
variation in this tree. A publicly available, live ref. collection of P. trichocarpa from the University of British Columbia Botanical
Garden was used in this study to survey variation in nine different genes among individuals from 41 different populations. A large
amt. of genetic variation was detected, but the level of variation appears to be less than in the related species, Populus tremula, based
on reported statistics for that tree. Genes examd. varied considerably in their level of variation, from PoptrTB1 which had a single
SNP, to PoptrLFY which had more than 23 in the 1000-bp region examd. Overall nucleotide diversity, measured as πTotal, was
relatively low at 0.00184. Linkage disequil., on the other hand, was higher than reported for some woody plant species, with mean R2
equal to 0.34. This study reveals the potential of Ecotilling as a rapid genotype discovery method to explore and utilize the large pool
of genetic variation in tree species.
Answer 426:
Methods and compositions using sirtuin modulators for treating or preventing obesity and insulin resistance disorders.
Sinclair, David A.; Alexander-Bridges, Maria. (President and Fellows of Harvard College, USA; The General Hospital Corporation).
U.S. Pat. Appl. Publ. (2006), 154 pp., Cont.-in-part of U.S. Ser. No. 27,779. CODEN: USXXCO US 2006111435 A1 20060525
Patent written in English. Application: US 2005-174000 20050701. Priority: US 2003-533712 20031229; US 2004-588643

US 20060111435 A1 20060525 US 2005-174000 20050701
US 20050171027 A1 20050804 US 2004-27779 20041229
AU 2006266125 A1 20070111 AU 2006-266125 20060628
CA 2613636 A1 20070111 CA 2006-2613636 20060628
WO 2007005453 A2 20070111 WO 2006-US25138 20060628
WO 2007005453 A3 20070614
EP, OA
EP 1912632 A2 20080423 EP 2006-774176 20060628
PT RO SE SI SK TR
flavanone
US 2003-533712P P 20031229
US 2004-588643P P 20040716
US 2004-27779 A2 20041229
US 2005-174000 A 20050701
WO 2006-US25138 W 20060628
Abstract
The invention provides methods and compns. for modulating the activity or level of a sirtuin, thereby treating or preventing obesity or
an insulin resistance disorder, e.g. diabetes, in a subject. Exemplary methods comprise contacting a cell with a sirtuin activating
compd. or an inhibitory compd. to thereby increase or decrease fat accumulation, resp.
Answer 427:
Carcinogenesis inhibitors containing natural chalcones, coumarins, flavanones, and/or diacetylene derivative. Akihisa,
Toshihiro; Tokuda, Harukuni; Ukiya, Motohiko; Hasegawa, Daisuke. (Nihon University, Japan). Jpn. Kokai Tokkyo Koho (2006),
14 pp. CODEN: JKXXAF JP 2006131594 A 20060525 Patent written in Japanese. Application: JP 2004-325369 20041109.

JP 2006131594 A 20060525 JP 2004-325369 20041109
JP 2004-325369 20041109
Abstract
Title inhibitors contain dorsmanin A, xanthoangelol I, J, xanthotoxin, isopimpinellin, osthenol, isobavachin, mundulea flavanone B,
8-geranylnaringenin, and/or (11S,16R)-dihydroxyoctadeca-9Z,17-diene-12,14-diyn-1-yl acetate. They may be added to foods,
beverages, and feeds. Thus, xanthoangelol I and J completely inhibited TPA-induced expression of Epstein-Barr virus early antigen in
Raji cells with their survival rate 70%, vs. 60%, for curcumin.
Answer 428:
Flavonones in grapefruit, lemons, and limes: A compilation and review of the data from the analytical literature. Peterson,
Julia J.; Beecher, Gary R.; Bhagwat, Seema A.; Dwyer, Johanna T.; Gebhardt, Susan E.; Haytowitz, David B.; Holden, Joanne M.
Tufts University Friedman School of Nutrition Science & Policy, Boston, MA, USA. Journal of Food Composition and Analysis
(2006), 19(Suppl.), S74-S80. Publisher: Elsevier, CODEN: JFCAEE ISSN: 0889-1575. Journal; General Review written in English.
flavanone
Abstract
A review. In order to develop a database for flavanones, the dominant flavonoid class in the genus citrus, the relevant scientific
literature on flavonoids in grapefruit, lemons, and limes was searched, abstracted, documented, standardized by taxons and units
(mg/100 g) and examd. for quality. Values for eight flavanones (didymin, eriocitrin, hesperidin, naringin, narirutin, neoeriocitrin,
neohesperidin, poncirin) are presented. Grapefruit had a total flavanone content (summed means) of 27 mg/100 g as aglycons and a
distinct flavanone profile, dominated by naringin. White grapefruit varieties tended to be slightly but not significantly higher in total
flavanones than pink and red varieties. For lemons, total flavanones (summed means) were 26 mg/100 g and for limes 17 mg/100 g.
The flavanone profiles of both lemons and limes were dominated by hesperidin and eriocitrin.
Answer 429:
Flavanones in oranges, tangerines (mandarins), tangors, and tangelos: a compilation and review of the data from the
analytical literature. Peterson, Julia J.; Dwyer, Johanna T.; Beecher, Gary R.; Bhagwat, Seema A.; Gebhardt, Susan E.;
Haytowitz, David B.; Holden, Joanne M. Tufts University Friedman School of Nutrition Science & Policy, Boston, MA, USA.
Journal of Food Composition and Analysis (2006), 19(Suppl.), S66-S73. Publisher: Elsevier, CODEN: JFCAEE ISSN: 0889-1575.
Journal; General Review written in English. CAN 145:417209 AN 2006:488077 CAPLUS (Copyright (C) 2008 ACS on SciFinder
(R))
Abstract
A review. Flavanones constitute the majority of flavonoids in citrus fruits such as sweet (Citrus sinensis) and sour oranges (C.
aurantium) and their near relatives-tangerines/mandarins (C. reticulata), tangors and tangelos. The relevant chem. analytic literature
was searched, abstracted, documented, standardized, examd. for quality, enumerated, and summarized in a database for these citrus
flavanones: hesperidin, naringin, narirutin, eriocitrin, neohesperidin, didymin, neoeriocitrin, and poncirin. Sour oranges had a distinct
flavanone profile dominated by naringin and neohesperidin, and were highest in total flavanones (summed means) (48 mg/100 g
aglycons). Total flavanones (summed means) in sweet oranges, tangerines, and tangors were similar (.apprx.20 mg/100 g), and
hesperidin and narirutin dominated the flavanone profiles for these three fruits. Total flavanones (summed means) in tangelos (30
mg/100) were midway between sour and sweet oranges and the tangelo flavanone profile exhibited characteristics of both species. The
database provides information on several varieties of citrus and eight flavanone compds.
Answer 430:
Studies on the constituents of Scutellaria species (XXII). Constituents of the roots of Scutellaria amabilis Hara. Miyaichi,
Yukinori; Hanamitsu, Eiji; Kizu, Haruhisa; Tomimori, Tsuyoshi. Department of Pharmacognosy, Pharmaceutical Sciences, Hokuriku
University, Ho-3, Kanagawa-machi, Kanazawa, Ishikawa, Japan. Chemical & Pharmaceutical Bulletin (2006), 54(4), 435-441.
Publisher: Pharmaceutical Society of Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN 145:141189
Abstract
From the roots of Scutellaria amabilis, eleven new flavonoids, 5,7,2'-trihydroxy-8-methoxyflavone 7-O-β-D-glucopyranoside,
5,7,2'-trihydroxy-8-methoxyflavone 2'-O-β-D-glucopyranoside, 5,7-dihydroxy-8,2'-dimethoxyflavone 7-O-β-D-glucopyranoside,
5,7,2'-trihydroxyflavone 2'-O-β-D-glucopyranoside, 5,7,2',5'-tetrahydroxyflavone 7-O-β-D-glucuronopyranoside,
flavanone
(2S)-5,7,2',5'-tetrahydroxyflavanone, (2S)-5,7,2',5'-tetrahydroxyflavanone 7-O-β-D-glucopyranoside,

(2S)-5,7,2',5'-tetrahydroxyflavanone 7-O-β-D-glucuronopyranoside, (2S)-7,2'-dihydroxy-5-methoxyflavanone
7-O-β-D-glucuronopyranoside, (I-2S)-I-5,II-5,I-7,II-7,I-2',II-2',II-5'-heptahydroxy-[I-6,II-6']-flavanonylflavone and
(I-2S)-I-5,II-5,I-7,II-7,I-2',II-2',I-5',II-5'-octahydroxy-[I-6,II-6']-flavanonylflavone, were isolated, together with ten known flavonoids,
wogonin (5,7-dihydroxy-8-methoxyflavone), 5,7-dihydroxy-8,2'-dimethoxyflavone, (2S)-5,7,2'-trihydroxyflavanone, scutevulin
(5,7,2'-trihydroxy-8-methoxyflavone), 5,7,4'-trihydroxy-8-methoxyflavone, alpinetin ((2S)-7-hydroxy-5-methoxyflavanone),
5,7,2'-trihydroxyflavone, 5,7,2',5'-tetrahydroxyflavone, (2S)-7,2'-dihydroxy-5-methoxyflavanone and
5,7-dihydroxy-8,2'-dimethoxyflavone 7-O-β-D-glucuronopyranoside. The structures were detd. on the basis of chem. and spectral
data.
Answer 431:
Hepatoprotective compounds of the roots of Cudrania tricuspidata on tacrine-induced cytotoxicity in Hep G2 cells. An,
Ren-Bo; Sohn, Dong-Hwan; Kim, Youn-Chul. College of Pharmacy, Wonkwang University, Iksan, S. Korea. Biological &
Pharmaceutical Bulletin (2006), 29(4), 838-840. Publisher: Pharmaceutical Society of Japan, CODEN: BPBLEO ISSN: 0918-6158.
Abstract
The bioassay-guided fractionation of the MeOH ext. of the root barks of Cudrania tricuspidata furnished three hepatoprotective
compds., gerontoxanthone A (2), cudraflavone B (4), gericudranin E (5), together with four prenylated xanthones, cudraxanthone B (3),
isocudraxanthone K (6), cudraxanthone C (7), cudraxanthone H (8), and a prenylated flavanone, euchrestaflavanone C (1). Compds. 4
and 5 showed significant hepatoprotective effects with the EC50 values of 37.39±0.4 and 39.87±0.7 μM, resp., and compd. 2 showed
moderate hepatoprotective effect with an EC50 value of 125.9±1.5 μM, against tacrine-induced cytotoxicity in Hep G2 cells. Silybin
as pos. control showed an EC50 value of 84.76±0.5 μM. Isocudraxanthone K is a new compd.
Answer 432:
The Discovery of New 11β-Hydroxysteroid Dehydrogenase Type 1 Inhibitors by Common Feature Pharmacophore Modeling
and Virtual Screening. Schuster, Daniela; Maurer, Evelyne M.; Laggner, Christian; Nashev, Lyubomir G.; Wilckens, Thomas;
Langer, Thierry; Odermatt, Alex. Institute of Pharmacy, Department of Pharmaceutical Chemistry, University of Innsbruck,
Innsbruck, Austria. Journal of Medicinal Chemistry (2006), 49(12), 3454-3466. Publisher: American Chemical Society, CODEN:
JMCMAR ISSN: 0022-2623. Journal written in English. CAN 145:137256 AN 2006:476237 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
11β-Hydroxysteroid dehydrogenase (11β-HSD) enzymes catalyze the conversion of biol. inactive 11-ketosteroids into their active
11β-hydroxy derivs. and vice versa. Inhibition of 11β-HSD1 has considerable therapeutic potential for glucocorticoid-assocd. diseases
including obesity, diabetes, wound healing, and muscle atrophy. Because inhibition of related enzymes such as 11β-HSD2 and
17β-HSDs causes sodium retention and hypertension or interferes with sex steroid hormone metab., resp., highly selective 11β-HSD1
inhibitors are required for successful therapy. Here, the authors employed the software package Catalyst to develop ligand-based
multifeature pharmacophore models for 11β-HSD1 inhibitors. Virtual screening expts. and subsequent in vitro evaluation of promising
hits revealed several selective inhibitors. Efficient inhibition of recombinant human 11β-HSD1 in intact transfected cells as well as
endogenous enzyme in mouse 3T3-L1 adipocytes and C2C12 myotubes was demonstrated for compd. (I), which was able to block
subsequent cortisol-dependent activation of glucocorticoid receptors with only minor direct effects on the receptor itself. Our results
suggest that inhibitor-based pharmacophore models for 11β-HSD1 in combination with suitable cell-based activity assays, including
flavanone
such for related enzymes, can be used for the identification of selective and potent inhibitors.
Me CH 2 CH 2 CO 2 H
CH
Me
O
Me
Me
AcO O
Me H
Me I
Answer 433:
Naringenin is a novel inhibitor of Dictyostelium cell proliferation and cell migration. Misty, Russ; Martinez, Raquel; Ali,
Hind; Steimle, Paul A. Department of Biology, University of North Carolina, Greensboro, NC, USA. Biochemical and
Biophysical Research Communications (2006), 345(1), 516-522. Publisher: Elsevier, CODEN: BBRCA9 ISSN: 0006-291X. Journal
Abstract
Naringenin is a flavanone compd. that alters crit. cellular processes such as cell multiplication, glucose uptake, and mitochondrial
activity. The social amoeba Dictyostelium discoideum was used as a model system for examg. the cellular processes and signaling
pathways affected by naringenin. Naringenin inhibited Dictyostelium cell division in a dose-dependent manner (IC50 .apprx. 20 μM).
Assays of Dictyostelium chemotaxis and multicellular development revealed that naringenin possesses a previously unrecognized
ability to suppress amoeboid cell motility. Naringenin, which is known to inhibit phosphatidylinositol 3-kinase activity, had no apparent
effect on phosphatidylinositol 3,4,5-trisphosphate synthesis in live Dictyostelium cells; suggesting that this compd. suppresses cell
growth and migration via alternative signaling pathways. In another context, the discoveries described here highlight the value of using
the Dictyostelium model system for identifying and characterizing the mechanisms by which naringenin, and related compds., exert
their effects on eukaryotic cells.
Answer 434:
Lipopolysaccharide plus 12-o-tetradecanoylphorbol 13-acetate induction of migration and invasion of glioma cells in vitro
and in vivo: Differential inhibitory effects of flavonoids. Shen, S. C.; Lin, C. W.; Lee, H. M.; Chien, L. L.; Chen, Y. C.
Department of Dermatology, School of Medicine, Taipei Medical University, Taipei, Taiwan. Neuroscience (San Diego, CA, United
States) (2006), 140(2), 477-489. Publisher: Elsevier, CODEN: NRSCDN ISSN: 0306-4522. Journal written in English. CAN
Abstract
In an earlier study, we reported that nitric oxide is involved in lipopolysaccharide plus 12-o-tetradecanoylphorbol 13-acetate-induced
flavanone
malignant transformation via increases in metalloproteinase 9 enzyme activity and inducible nitric oxide synthase gene expression in
rat glioma C6 cells, however the mechanism has remained undefined. Lipopolysaccharide plus 12-o-tetradecanoylphorbol 13-acetate,
but not lipopolysaccharide or 12-o-tetradecanoylphorbol 13-acetate alone, induced transformation in glioma C6 cells (but not in human
glioblastoma cells GBM-8401 cells) without affecting their viability. An increase in inducible nitric oxide synthase protein expression,
nitric oxide prodn., and metalloproteinase 9 enzyme activity is identified lipopolysaccharide/12-o-tetradecanoylphorbol
13-acetate-treated C6 cells, however lipopolysaccharide/12-o-tetradecanoylphorbol 13-acetate and 12-o-tetradecanoylphorbol
13-acetate (but not lipopolysaccharide) addn. shows the similar inductive pattern on metalloproteinase 9 enzyme activity without
affecting inducible nitric oxide synthase protein expression and nitric oxide prodn. in GBM-8401 cells. Treatment of C6 cells with
lipopolysaccharide/12-o-tetradecanoylphorbol 13-acetate increases the expression of phosphorylated extracellular regulated protein
kinases and Jun N-terminal kinases, but not p38, proteins, and an addn. of the extracellular regulated protein kinases inhibitor PD98059
or Jun N-terminal kinases inhibitors SP600125, but not the p38 inhibitor SB203580, significantly blocked
lipopolysaccharide/12-o-tetradecanoylphorbol 13-acetate-induced inducible nitric oxide synthase protein expression and
metalloproteinase 9 enzyme activity accompanied by blocking morphol. transformation in C6 cells. Among 19 structurally related
flavonoids, kaempferol and wogonin exhibit significant inhibitory effects on lipopolysaccharide/12-o-tetradecanoylphorbol
13-acetate-induced morphol.
transformation and colony formation, and attenuation of inducible nitric oxide synthase, phosphorylated extracellular regulated protein
kinases protein expression, and metalloproteinase 9 enzyme activity was obsd. 2'-OH flavone at a dose of 100 μM inhibition of
lipopolysaccharide/12-o-tetradecanoylphorbol 13-acetate-induced events via apoptosis induction is identified. Furthermore,
lipopolysaccharide/12-o-tetradecanoylphorbol 13-acetate, but not lipopolysaccharide or 12-o-tetradecanoylphorbol 13-acetate, induces
tumoral invasion and migration in vitro and in vivo, and those are blocked by kaempferol and wogonin addn. These data suggest that
combination of lipopolysaccharide and 12-o-tetradecanoylphorbol 13-acetate promotes tumoral progression via activating
metalloproteinase 9 enzyme activity and inducible nitric oxide synthase gene expression, which is located downstream of
mitogen-activated protein kinases activation, in rat glioma cells C6. Kaempferol and wogonin exhibit effective inhibitory effects on
lipopolysaccharide/12-o-tetradecanoylphorbol 13-acetate-induced events, and thus possess the potential for further development.
Answer 435:
Total synthesis of three naturally occurring 6,8-di-C-glycosylflavonoids: phloretin, naringenin, and apigenin
bis-C-β-D-glucosides. Sato, Shingo; Akiya, Toshiki; Nishizawa, Hiroaki; Suzuki, Toshiyuki. Department of Chemistry and
Chemical Engineering, Faculty of Engineering, Yamagata University, 4-3-16 Jonan, Yonezawa-shi, Yamagata, Japan.
Carbohydrate Research (2006), 341(8), 964-970. Publisher: Elsevier B.V., CODEN: CRBRAT ISSN: 0008-6215. Journal written in
Abstract
Three naturally occurring di-C-glycosylflavonoids, phloretin (dihydrochalcone) I, naringenin (flavanone) II, and apigenin (flavone) III
bis-6,8-C-β-D-glucopyranosides, were synthesized in total yields of 52.3%, 53.5%, and 36.4%, resp., starting from the key compd.,
di-C-β-D-glucopyranosylphloroacetophenone (IV). Benzyl protection of the phenolic hydroxyls in IV and a subsequent aldol
condensation with benzyloxybenzaldehyde led to the prodn. of chalcone, which, after hydrogenolysis or acid hydrolysis and
deprotection, gave I and II, resp. The acetylation of II, followed by DDQ oxidn. and deprotection, gave III.
flavanone
OH
OH OH
HO O
HO OH OH
HO O
HO HO OH
OH O I
OH
OH OH
HO O OH
HO O
HO O
HO HO OH
OH O II
OH
OH OH
HO O OH
HO O
HO O
HO HO OH
OH O III
Answer 436:
flavanone
Molecular modeling of polyphenols from Croatian wines. Medic-Saric, M.; Mornar, A.; Rastija, V.; Jasprica, I.; Nikolic, S.
Department of Pharmaceutical Chemistry, Faculty of Pharmacy and Biochemistry, University of Zagreb, Zagreb, Croatia. Lecture
Series on Computer and Computational Sciences (2005), 4 B(Advances in Computational Methods in Sciences and Engineering),
1566-1569. Publisher: Brill Academic Publishers, CODEN: LSCCAR ISSN: 1573-4196. Journal written in English. CAN 145:375961
Abstract
Because of health benefits of phenolic compds. in wine, it is important to investigate their structure-property relationship. We have
investigated linear and nonlinear (polynomial) relationships between given topol. indexes and lipophilicity of polyphenols, main
pharmacol. active components of wine.
Answer 437:
Structure-radical scavenging activity relationships of phenolic compounds from traditional Chinese medicinal plants.
Cai, Yi-Zhong; Sun, Mei; Jie Xing; Luo, Qiong; Corke, Harold. Department of Botany, The University of Hong Kong, Hong Kong,
Peop. Rep. China. Life Sciences (2006), 78(25), 2872-2888. Publisher: Elsevier B.V., CODEN: LIFSAK ISSN: 0024-3205.
Abstract
Traditional Chinese medicinal plants assocd. with anticancer contain a wide variety of natural phenolic compds. with various structural
features and possessing widely differing antioxidant activity. The structure-radical scavenging activity relationships of a large no. of
representative phenolic compds. (e.g., flavanols, flavonols, chalcones, flavones, flavanones, isoflavones, tannins, stilbenes,
curcuminoids, phenolic acids, coumarins, lignans, and quinones) identified in the traditional Chinese medicinal plants were evaluated
using the improved ABTS⋅+ and DPPH methods. Different categories of tested phenolics showed significant mean differences in
radical scavenging activity. Tannins demonstrated the strongest activity, while most quinones, isoflavones, and lignans tested
showed the weakest activity. This study confirmed that the no. and position of hydroxyl groups and the related glycosylation and
other substitutions largely detd. radical scavenging activity of the tested phenolic compds. The differences in radical scavenging
activity were attributed to structural differences in hydroxylation, glycosylation and methoxylation. The ortho-dihydroxy groups were
the most important structural feature of high activity for all tested phenolic compds. Other structural features played a modified role
in enhancing or reducing the activity. Within each class of phenolic compds., the structure-activity relation was elucidated and
discussed. This study reveals the structure-activity relationships of a large series of representative natural phenolic compds. more
systematically and fully than previous work. Structure-radical scavenging activity relationships of some natural phenolics identified in
the medicinal plants were evaluated for the first time.
Answer 438:
Inhibition of CYP6B1-Mediated Detoxification of Xanthotoxin by Plant Allelochemicals in the Black Swallowtail (Papilio
polyxenes). Wen, Zhimou; Berenbaum, May R.; Schuler, Mary A. Department of Cell and Developmental Biology, University of
Illinois, Urbana, IL, USA. Journal of Chemical Ecology (2006), 32(3), 507-522. Publisher: Springer, CODEN: JCECD8 ISSN:
Abstract
flavanone
The structural and biosynthetic diversity of allelochems. in plants is thought to arise from selection for additive toxicity as a
consequence of toxin mixt. or for enhanced toxicity as a result of synergism. In order to understand how insects cope with this type
of plant defense, we tested the effects of some allelochems. in host plants of the black swallowtail Papilio polyxenes on the
xanthotoxin-metabolic activity of CYP6B1, the principal enzyme responsible for the detoxification of furanocoumarins in this
caterpillar. Addnl., the effects of some synthetic compds. not normally encountered by P. polyxenes on CYP6B1 were tested. These
studies demonstrate that the integrity of furanocoumarin structure is important for competitive binding to the active site of CYP6B1,
even though the carbonyl group on the pyranone ring apparently does not affect its inhibitory capacity, as in the case of
furanochromones. Angular furanocoumarins are generally less phototoxic to many organisms than linear furanocoumarins due to their
reduced capacity for crosslinking DNA strands, yet they are more toxic than linear furanocoumarins to black swallowtail larvae. This
enhanced toxicity in vivo may be due to the ability of angular furanocoumarins to bind to the active site of CYP6B1 without being
rapidly metabolized. This binding reduces the availability of CYP6B1 to metabolize other linear furanocoumarins. The
structure-activity relationships for methylenedioxyphenyl compds., flavonoids, imidazole, and imidazole derivs. are also discussed in
light of their capacity to inhibit the xanthotoxin-metabolic activity of CYP6B1.
Answer 439:
Two new dihydroflavanoids from Patrinia villosa Juss (II). Peng, Jin Yong; Fan, Guo Rong; Wu, Yu Tian. Shanghai Key
Laboratory for Pharmaceutical Metabolite Research, School of Pharmacy, Second Military Medical University, Shanghai, Peop. Rep.
China. Chinese Chemical Letters (2006), 17(4), 485-488. Publisher: Chinese Chemical Society, CODEN: CCLEE7 ISSN:
Abstract
Two new dihydroflavonoids named villosin A and villosin B were obtained from the traditional Chinese medicinal herb Patrinia villosa
Juss. Their structures were elucidated as (2S)-5,2',6'-trihydroxy-2'',2''-dimethylpyrano [5'',6'':6,7]flavanone and
(2S,3''S)-5,2',6'-trihydroxy-3''-γ,γ-dimethylallyl-2'',2''-dimethyl-3'',4''-dihydropyrano [5'',6'':6, 7]flavanone by spectroscopic methods
including UV, IR, HR-TOF-MS, 1D NMR and 2D NMR techniques.
Answer 440:
(±)-Diinsininone: made nature's way. Selenski, Carolyn; Pettus, Thomas R. R. University of California, Santa Barbara,
Department of Chemistry & Biochemistry, Santa Barbara, CA, USA. Tetrahedron (2006), 62(22), 5298-5307. Publisher: Elsevier
B.V., CODEN: TETRAB ISSN: 0040-4020. Journal written in English. CAN 145:103457 AN 2006:428115 CAPLUS (Copyright
Abstract
The synthesis of (±)-diinsininone (I), the racemic aglycon of diinsinin, was reported. This was the first construction of a
proanthocyanidin (PA) type-A compd. incorporating a [3.3.1]-bicyclic ketal as its characteristic core. The strategy utilized a coupling
between a benzopyrilium salt and a flavanone that proved applicable to other PA type-A compds. During this undertaking, treatment of
(±)-naringenin with 2-iodoxybenzoic acid (IBX) followed by reductive work-up afforded (±)-eriodictyol. This reactivity mirrors that of
catechol hydroxylase (F3H) found in the flavonoid pathway. Other interesting transformations included the formation of flavonoids
through an ortho-quinone methide (o-QM) cycloaddn.-oxidn. sequence and regioselective β-glycosidations of several unprotected
flavanones suggesting a likely synthesis of diinsinin from the aglycon I.
flavanone
OH
OH
O
O
HO
OH O OH
HO I
Answer 441:
Enantioseparation using alkoxyphenylcarbamates of cellulose and amylose as chiral stationary phase for high-performance
liquid chromatography. Yamamoto, Chiyo; Inagaki, Shinji; Okamoto, Yoshio. Department of Applied Chemistry, Graduate
School of Engineering, Nagoya University, Chikusa-ku, Nagoya, Japan. Journal of Separation Science (2006), 29(6), 915-923.
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: JSSCCJ ISSN: 1615-9306. Journal written in English. CAN 146:74176
Abstract
Cellulose and amylose phenylcarbamates having one or two alkoxy groups on a Ph ring were synthesized, and their chiral recognition
abilities as chiral stationary phases for HPLC were evaluated. Compared to the 4-methoxyphenylcarbamates of cellulose and
amylose, which are known to show a poor chiral recognition, the 3-methoxyphenylcarbamates exhibited much higher chiral recognitions.
For cellulose derivs., as the bulkiness of the 3-alkoxy group increased, the chiral recognition ability increased. However, for the
amylose derivs., a clear relation between the chiral recognition and the bulkiness of the alkoxy group was not obsd., and the
3-methoxy, ethoxy, and isopropoxyphenylcarbamates showed relatively high chiral recognitions. The introduction of two methoxy
groups to the meta-positions decreased the chiral recognition ability. To discuss the relation between the structure and chiral
recognition ability of the alkoxyphenylcarbamates, their mol. models were constructed.
Answer 442:
Roles of HMGB-1 and soluble RAGE in endotoxic shock. Hasunuma, Ryoichi; Kawaguchi, Kiichiro; Maruyama, Hiroko;
Takimoto, Hiroaki; Kumazawa, Yoshio. Dep. of Science, Kitasato University, Japan. Endotokishin Kenkyu (2005), 8 4-11.
Publisher: Igaku Tosho Shuppan K.K., CODEN: EKNEBO Journal; General Review written in Japanese. CAN 145:373465 AN
Abstract
flavanone
A review discussing (1) endotoxin shock induced by Salmonella infection in mice, (2) pathol. opinion of the mouse liver with
infection-induced endotoxic shock, (3) expression of HMGB-1 in mice with infection-induced endotoxic shock, (4) expression of sol.
RAGE in mice with infection-induced endotoxic shock, (5) expression of HMGB-1 in galactosamine-sensitized mice, (6) sol. RAGE
expression in galactosamine-sensitized mice and (7) suppression of endotoxic shock in mice by a citrus flavanone naringin and
hesperidin.
Answer 443:
Isolation of cDNAs for R2R3-MYB, bHLH and WDR transcriptional regulators and identification of c and ca mutations
conferring white flowers in the Japanese morning glory. Morita, Yasumasa; Saitoh, Miho; Hoshino, Atsushi; Nitasaka, Eiji; Iida,
Shigeru. National Institute for Basic Biology, Okazaki, Japan. Plant and Cell Physiology (2006), 47(4), 457-470. Publisher:
Japanese Society of Plant Physiologists, CODEN: PCPHA5 ISSN: 0032-0781. Journal written in English. CAN 145:227471 AN
Abstract
The transcriptional regulators for anthocyanin biosynthesis include members of proteins contg. an R2R3-MYB domain, a bHLH (basic
helix-loop-helix) domain and conserved WD40 repeats (WDRs). Spacial and temporal expression of the structural genes encoding the
enzymes for anthocyanin biosynthesis is thought to be detd. by combinations of the R2R3-MYB, bHLH and WDR factors and their
interactions. While the wild-type Japanese morning glory (Ipomoea nil) exhibits blue flowers with colored stems and dark-brown seeds,
the c mutants display white flowers with red stems and colored seeds, and the ca mutants exhibit white flowers with green stems and
ivory seeds. Here, the authors characterize the tissue-specific expression of three MYB genes, three bHLH genes and two WDR
genes in I. nil. The authors also show that the recessive c-1 and ca alleles are frameshift mutations caused by a 2 bp deletion and 7
bp insertions in the genes for the R2R3-MYB and WDR transcriptional regulators designated as InMYB1 and InWDR1, resp. In addn.
to defects in flower, stem and seed pigmentations, the ca mutants were found to show reduced trichome formation in seeds but to
produce leaf and stem trichomes and root hairs normally. Except for the gene for chalcone synthase E in the ca mutant, all structural
genes tested were coordinately reduced in both c-1 and ca mutant flower limbs. However, slight but significant expression of the
genes for chalcone synthase D, chalcone isomerase and flavanone 3-hydroxylase in the pathway for flavonol biosynthesis was
detectable in c-1 and ca mutants, whereas no such residual expression could be obsd. in other genes involved in the later anthocyanin
biosynthesis pathway. The biol. roles of the C-1 and Ca genes in I. nil epidermal traits and their evolutionary implications are also
discussed.
Answer 444:
Structurally unique biflavonoids from Selaginella chrysocaulos and Selaginella bryopteris. Swamy, Ramalla Chidananda;
Kunert, Olaf; Schuhly, Wolfgang; Bucar, Franz; Ferreira, Daneel; Rani, Vanapatla Swarupa; Kumar, Bobbala Ravi; Rao, Achanta
Venkata Narasimha Appa. University College of Pharmaceutical Sciences, Kakatiya University, Warangal, India. Chemistry &
Biodiversity (2006), 3(4), 405-413. Publisher: Verlag Helvetica Chimica Acta AG, CODEN: CBHIAM ISSN: 1612-1872. Journal
Abstract
Chem. investigation of S. chrysocaulos from Northeast India yielded 3 new (i.e., 1-3) and 2 known biflavonoids. From S. bryopteris,
collected in the southern part of India, 1 new and 11 known biflavonoids of the amentoflavone- and hinokiflavone-type were isolated
and identified. The structures of the compds. were elucidated by 1D- and 2D-NMR spectroscopy, and by mass spectrometry. The
abs. configurations of chiral biflavonoids with flavanone subunits (from S. bryopteris) were detd. with the aid of circular-dichroism (CD)
spectroscopy. Several very rare or even unprecedented substructures in biflavonoids were found.
flavanone
Answer 445:
Cytotoxic chalcones and flavanones from the tree bark of Cryptocarya costata. Usman, Hanapi; Hakim, Euis H.; Harlim, Tjodi;
Jalaluddin, Muhammad N.; Syah, Yana M.; Achmad, Sjamsul A.; Takayama, Hiromitsu. Chemistry Department, Hasanuddin
University, Makassar, Indonesia. Zeitschrift fuer Naturforschung, C: Journal of Biosciences (2006), 61(3/4), 184-188. Publisher:
Verlag der Zeitschrift fuer Naturforschung, CODEN: ZNCBDA ISSN: 0939-5075. Journal written in English. CAN 146:32542 AN
Abstract
A new flavanone, 7-hydroxy-5,6-dimethoxyflavanone (1), together with three other flavonoids, didymocarpin (2),
2',4'-dihydroxy-5',6'-dimethoxychalcone (3), and isodidymocarpin (4), had been isolated from the methanol ext. of the tree bark of
Cryptocarya costata. The structures of these compds. were detd. based on spectral evidence, including UV, IR, 1-D and 2-D NMR,
and mass spectra. Cytotoxic properties of compds. 1-4 were evaluated against murine leukemia P-388 cells. The chalcones 3 and 4
were found to have substantial cytotoxicity with IC50 of 5.7 and 11.1 μM, resp.
Answer 446:
Molecular characterization of the flavonoid biosynthetic pathway and flower color modification of Nierembergia sp.
Ueyama, Yukiko; Katsumoto, Yukihisa; Fukui, Yuko; Fukuchi-Mizutani, Masako; Ohkawa, Hideo; Kusumi, Takaaki; Iwashita, Takashi;
Tanaka, Yoshikazu. Division of Molecular Science, Graduate School of Science and Technology, Kobe University, 1-1 Rokkodai,
Nada, Kobe, Japan. Plant Biotechnology (Tokyo, Japan) (2006), 23(1), 19-24. Publisher: Japanese Society for Plant Cell and
Molecular Biology, CODEN: PLBIF6 ISSN: 1342-4580. Journal written in English. CAN 145:468033 AN 2006:412907 CAPLUS
Abstract
Nierembergia sp., a popular floricultural species, only has violet and white flower color and lacks pink to red. To elucidate the reason,
we analyzed its flavonoids. Its major anthocyanin was detd. to be delphinidin
3-O-(6-O-(4-O-(4-O-(6-O-caffeoyl-β-D-glucopyranosyl)-p-coumaroyl)-α-L-rhamnosyl)-β-D-glucopyranosyl)-5-O-β-D-glucopyranoside.
The petals rarely contained cyanidin and pelargonidin, and they contained more flavonols than anthocyanins. We also characterized
the biosynthetic pathway by cloning the cDNAs encoding enzymes involved in the flavonoid biosynthesis pathway: chalcone synthase
(CHS), flavanone 3-hydrozylase (F3H), flavonoid 3'-hydroxylase (F3'H), flavonoid 3',5'-hydroxylase (F3'5'H), dihydroflavonol
4-reductase (DFR), flavonol synthase (FLS), and UDP-rhamnose: anthocyanidin 3-glucoside rhamnosyltransferase (3RT). Northern
blot anal. revealed that the expressions of CHS, F3'5'H, DFR, and 3RT genes were coordinately regulated in parallel with anthocyanin
accumulation in the petals, indicating that anthocyanin biosynthesis is transcriptionally regulated; on the other hand, the transcripts of
the F3'H gene were rarely detected. Antisense suppression of the F3'5'H gene decreased the amt. of F3'5'H transcripts and that of
delphinidin. It was noteworthy that the color of the transgenic flower changed from violet to white rather than to reddish, which was the
expectation.
Answer 447:
Molecular characterization of the flavonoid biosynthesis of Verbena hybrida and the functional analysis of verbena and
Clitoria ternatea F3'5'H genes in transgenic verbena. Togami, Junichi; Tamura, Mihoko; Ishiguro, Kanako; Hirose, Chika;
flavanone
Okuhara, Hiroaki; Ueyama, Yukiko; Nakamura, Noriko; Yonekura-Sakakibara, Keiko; Fukuchi-Mizutani, Masako; Suzuki, Ken-ichi;
Fukui, Yuko; Kusumi, Takaaki; Tanaka, Yoshikazu. Institute for Advanced Technology, Suntory, Ltd., 1-1-1 Wakayamadai,
Shimamoto, Osaka, Japan. Plant Biotechnology (Tokyo, Japan) (2006), 23(1), 5-11. Publisher: Japanese Society for Plant Cell
and Molecular Biology, CODEN: PLBIF6 ISSN: 1342-4580. Journal written in English. CAN 145:468083 AN 2006:412905
Abstract
Homologues of the flavonoid 3',5'-hydroxylase (F3'5'H) gene, a key gene detg. flower color, were obtained from a Verbena hybrida
(verbena) cultivar Temari Violet, verbena cultivar Tapien Pink, and Clitoria ternatea (butterfly pea). The expression of the Temari and
butterfly pea homologues in yeast confirmed that they encoded F3'5'H. The two genes under the control of an enhanced cauliflower
mosaic virus 35S promoter were introduced into verbena Temari Sakura. Some of the transgenic verbena plants had elevated
delphinidin contents and flower color altered toward violet. Interestingly, the butterfly pea F3'5'H gene yielded more delphinidin and
gave clearer flower color change than the verbena Temari gene in the transgenic verbena plants. The results indicate that the choice
of the gene source should be considered to obtain strong phenotypic changes, even if the genes encode the same enzymic activity.
We also cloned some flavonoid biosynthetic genes from verbenas. The potential usefulness of verbena in the phytomonitoring of
environmental pollutants is also discussed.
Answer 448:
Use of glycosylated flavanones for the browning of skin or hair. Vielhaber, Gabriele; Jacobs, Karin; Herrmann, Martina.
(Symrise Gmbh & Co. KG, Germany). PCT Int. Appl. (2006), 69 pp. CODEN: PIXXD2 WO 2006045760 A1 20060504
EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, LY,
MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM,
TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE,
2005-EP55464 20051021. Priority: US 2004-621855 20041025. CAN 144:439568 AN 2006:411812 CAPLUS (Copyright (C)

WO 2006045760 A1 20060504 WO 2005-EP55464 20051021
DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KP, KR,
VN, YU, ZA, ZM, ZW
AU 2005298653 A1 20060504 AU 2005-298653 20051021
CA 2584767 A1 20060504 CA 2005-2584767 20051021
EP 1807039 A1 20070718 EP 2005-808058 20051021
flavanone
US 2004-621855P P 20041025
WO 2005-EP55464 W 20051021
Abstract
The use of a compd. having formula (I) is described as an agent for the browning of skin or hair wherein: R1 and R2 are mutually
independently H, OH, C1-C10-alkyl, C1 -C10-O-alkyl or O-prenyl, R3 is H, OH, O-glucose or O-rhamnose and R4 is a monosaccharide
radical or an oligosaccharide radical having 2, 3, 4 or 5 carbohydrate units, with the proviso that the compd. having formula I is not
used in the form of a prepn. based on Citrus aurantium dulcis.
R1
R4O O
R2
R3
OH O I
Answer 449:
Development of dinitrophenylated cyclodextrin derivatives for enhanced enantiomeric separations by high-performance

liquid chromatography. Zhong, Qiqing; He, Lingfeng; Beesley, Thomas E.; Trahanovsky, Walter S.; Sun, Ping; Wang, Chunlei;
Armstrong, Daniel W. Department of Chemistry, Iowa State University, Ames, IA, USA. Journal of Chromatography, A (2006),
1115(1-2), 19-45. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. CAN 145:136942
Abstract
The synthesis and evaluation of new dinitrophenyl (DNP) substituted β-cyclodextrin (β-CD) chiral stationary phases (CSPs) for the
enantiosepn. of various classes of chiral analytes by HPLC are presented. The dinitrophenyl substituted β-CD derivs. were
synthesized and covalently bonded to functionalized 5 μm spherical porous silica gel. These are the 1st reported derivatized
cyclodextrin which contains π-electron deficient substituents (i.e., π-acidic moieties). The column performance in terms of their ability
to sep. enantiomers is evaluated. A variety of different dinitro-substituted aryl groups were studied and compared. The pH of the
mobile phase buffers, the buffer compn., the no. and position of the dinitro groups on the Ph ring substituent, the degree of
substitution, and the bonding strategy all greatly affect the performance of the CSPs. A large variety of racemic compds. were sepd.
successfully on these CSPs. The bonded dinitrophenyl-derivatized cyclodextrins are stable in all three mobile phase modes, namely,
the reversed-phase, polar org., and normal phase modes. No degrdn. in column performance was obsd. in any mode of operation
even after >1000 injections. The anal. applicability of these types of CSPs for enantiomeric sepns. is discussed.
Answer 450:
flavanone
Preparative isolation of four new and two known flavonoids from the leaf of Patrinia villosa Juss. by counter-current
chromatography and evaluation of their anticancer activities in vitro. Peng, Jinyong; Fan, Guorong; Wu, Yutian. Shanghai
Key Laboratory for Pharmaceutical Metabolite Research, School of Pharmacy, Second Military Medical University, Shanghai, Peop.
Rep. China. Journal of Chromatography, A (2006), 1115(1-2), 103-111. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN:
Abstract
A preparative counter-current chromatog. (CCC) was used to isolate and sep. chem. constituents from the leaf of Patrinia villosa, a
famous traditional Chinese medicinal herb. Six flavonoids including two known and four novel compds. were successfully
simultaneous purified by CCC with a two-phase solvent system composed of n-hexane-Et acetate-methanol-water (10: 13: 13: 10,
vol./vol.) by increasing the flow rate of the mobile phase from 1.0 mL/min to 2.0 mL/min after 110 min to bring out the late eluters.
The sepn. produced total of 44.9 mg fraction I with 99.1% purity, 35.5 mg fraction II with 98.8% purity, 79.8 mg fraction III with 99.3%
purity, 45.8 mg fraction IV with 98.8% purity, 39.8 mg fraction V with 98.6% purity and 9.6 mg fraction VI with 97.5% purity from 400
mg crude ext. in one single isolation procedure and less than 10 h, and the obtained fractions were all analyzed by high performance
liq. chromatog. (HPLC). Their chem. structures were elucidated as (2S)-5,7,2',6'-tetrahydroxy-6,8-di (γ,γ-dimethylallyl) flavanone (1),
(2S)-5,7,2',6'-tetrahydroxy-6-lavandulylated flavanone (2), (2S)-5,7,2',6'-tetrahydroxy-4'-lavandulylated flavanone (3),
(2S)-5,2',6'-trihydroxy-2'',2''-dimethylpyrano [5'', 6'': 6, 7] flavanone (4), (2S,
3''S)-5,2',6'-trihydroxy-3''-γ,γ-dimethylallyl-2'',2''-dimethyl-3'',4''-dihydropyrano [5'', 6'': 6, 7] flavanone (5) and licoagrochalcone B (6),
resp., by spectrum methods including UV, IR, high resoln. (HR)-electrospray ionization (ESI)-MS, 1-dimension (1D) and 2-dimension
(2D) NMR techniques. Among them, compds. 2, 3, 4, and 5 were new compds. and discovered from nature for the first time. The
recoveries of the six compds. were 91.2%, 91.4%, 92.1%, 90.5%, 90.3% and 89.7%, resp., in CCC step. Subsequently, their
anticancer activities were also examd. to inhibit human cancer cells' growth including A549, BEL-7402, SGC-7901, MCF-7, HT-29, K562
and A498 cell lines by MTT method in vitro. The results indicated that the compds.
1, 2 and 3 exhibited high anticancer activities (IC50 < 7 μg/mL), esp. to K562 cancer cell (IC50 < 3.1 μg/mL), and the compds. 4, 5 and
6 exhibited weaker inhibition effect (IC50 < 30 μg/mL).
Answer 451:
Cosmetic composition containing an active agent and a urea compound. Burnier, Veronique; Lorant, Raluca. (L'Oreal, Fr.).
Fr. Demande (2006), 36 pp. CODEN: FRXXBL FR 2877221 A1 20060505 Patent written in French. Application: FR
2004-12368 20041122. Priority: FR 2004-52518 20041104. CAN 144:439565 AN 2006:409419 CAPLUS (Copyright (C) 2008

FR 2877221 A1 20060505 FR 2004-12368 20041122
FR 2877223 A1 20060505 FR 2004-52518 20041104
WO 2006048339 A2 20060511 WO 2005-EP13527 20051104
WO 2006048339 A3 20060727
flavanone
FR 2004-52518 A 20041104
US 2004-627284P P 20041115
FR 2004-12368 A 20041122
Abstract
A cosmetic compn. comprises a hydroxylated urea compd. and an active agent chosen from dermorelaxants, agents stimulating the
synthesis of dermal or epidermal extracellular matrix fibers located on the dermo-epidermal junction and/or preventing their degrdn.,
anti-glycation agents, lipolytic agents or lipogenesis inhibitors, anti-irritants agents and their mixts. The invention also discloses a
compn. contg. a hydroxylated urea compd. and an agent chosen from carotenoids, retinoids, flavanones, flavonols, isoflavones,
coumarins, lignans, stilbenoids, sapogenins, triterpene pentacyclic acids, β-hydroxy acids, their derives., ethers, or heterosides,
phenolic acids, precursor monomers of tannins, aminosugars, peptides, and their mixts. for the care and make-up of the skin. A lotion
contained carbomer 0.20, Me paraben 0.2, 2-hydroxyethyl urea 5, caffeine 0.5, oils 5, stearic acid 3, glyceryl stearate 0.50,, cetyl alc.
0.20, triethanolamine 0.5, diazolidinyl urea 0.3, and water q.s. 100%.
Answer 452:
Determination of flavonoid and limonoid compounds in citron (Citrus junos Sieb. et Tanaka) seeds by HPLC and HPLC/MS.
Woo, Kang-Lyung; Kim, Je-I.; Kim, Min-Chul; Chang, Duck-Kyu. Division of Food Science and Biotechnology, Kyungnam
University, Masan, S. Korea. Han'guk Sikp'um Yongyang Kwahak Hoechi (2006), 35(3), 353-358. Publisher: Korean Society of
Food Science and Nutrition, CODEN: HSYHFB ISSN: 1226-3311. Journal written in Korean. CAN 145:487881 AN 2006:407514
Abstract
Flavonoid and limonoid compds. were detd. by HPLC on the methanol and ethanol exts. from citron seeds. The quantities of the
compds. in these categories were higher in the ethanol ext. than methanol ext. The types of these compds. were detected in larger
nos. in the ethanol ext. The content of limonin was the largest in both methanol and ethanol ext. among the detectable compds.;
140.34 mg/100 g and 170.98 mg/100 g, resp., and the contents of other compds., caffeic acid, naringin, lutin, nomilin, were found in
large amt. in this order. The mol. wts. of forty two compds. in ethanol ext. were detd. with mass spectra and extd. ion current
chromatograms by HPLC/MS.
Answer 453:
New anti-inflammatory active flavanone glycoside from the Echinops echinatus Roxb. Yadava, R. N.; Singh, S. K. Natural
Products Laboratory, Department of Chemistry, Dr. H. S. Gour University, Sagar, India. Indian Journal of Chemistry, Section B:
Organic Chemistry Including Medicinal Chemistry (2006), 45B(4), 1004-1008. Publisher: National Institute of Science Communication
and Information Resources, CODEN: IJSBDB ISSN: 0376-4699. Journal written in English. CAN 145:351890 AN 2006:391088
Abstract
flavanone
A new antiinflammatory active flavanone glycoside

5,7-dihydroxy-8,4'-dimethoxyflavanone-5-O-α-L-rhamnopyranosyl-7-O-β-D-arabinopyranosyl-(1→4)-O-β-D-glucopyranoside A along with
a known compd. dihydroquercetin-4'-Me ether B have been isolated from the leaves of Echinops echinatus.
Answer 454:
A new flavanone from the wood of Amorpha fruticosa L. Lee, Hyun-Jung; Lee, Oh-Kyu; Kwon, Yeong-Han; Choi, Don-Ha; Kang,
Ha-Young; Lee, Hyeon-Yong; Paik, Ki-Hyon; Lee, Hak-Ju. Div. Wood Chemistry & Microbiology, Korea Forest Research Institute,
Seoul, S. Korea. Bulletin of the Korean Chemical Society (2006), 27(3), 426-428. Publisher: Korean Chemical Society, CODEN:
BKCSDE ISSN: 0253-2964. Journal written in English. CAN 145:99565 AN 2006:384363 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
A new flavanone, 3',5',7-trihydroxyflavanone, was isolated from the methanol ext. of the wood of A. fruticosa by column chromatog.
Its chem. structure was identified by instrumental anal. using UV, IR, mass, and NMR spectrometer.
Answer 455:
Glycosidase inhibitory flavonoids from Sophora flavescens. Kim, Jin Hyo; Ryu, Young Bae; Kang, Nam Suk; Lee, Byong
Won; Heo, Jong Soo; Jeong, Ill-Yun; Park, Ki Hun. Division of Applied Life Science (BK21 Program), Institute of Agricultural & Life
Sciences, Department of Agricultural Chemistry, Gyeongsang National University, Jinju, S. Korea. Biological & Pharmaceutical
Bulletin (2006), 29(2), 302-305. Publisher: Pharmaceutical Society of Japan, CODEN: BPBLEO ISSN: 0918-6158. Journal written
Abstract
The MeOH ext. of Sophora flavescens showed a potent glycosidase inhibitory activity. Active components were identified as
well-known flavonoid antioxidants: kushenol A (1), (-)-kurarinone (2), sophoraflavanone G (3), 2'-methoxykurarinone (4), kurarinol (5),
8-prenylkaempferol (6), isoxanthohumol (7), kuraridine (8), and maackiain (9). All flavonoids were effective inhibitors of α-glucosidase
and β-amylase. Interestingly, lavandulylated flavanones 1-5 had strong α-glucosidase inhibitory activities, with IC50 values of 45, 68,
37, 155, and 179 μM, resp. Kushenol A (1) which does not bear a 4'-hydroxy group showed selective α-glucosidase inhibitory activity.
Lavandulylated chalcone, kuraridine (8), exhibited IC50 value of 57 μM against β-glucosidase, which is the 1st report of a chalcone
displaying glycosidase inhibition. Results showed that 8-lavandulyl group in B-ring was a key factor of the glycosidase inhibitory
activities. The inhibition pattern was noncompetitive for α-glucosidase, whereas mixed inhibition was obsd. for β-amylase.
Answer 456:
Antioxidative flavanone glycosides from the branches and leaves of Viscum coloratum. Yao, Hui; Liao, Zhi-Xin; Wu, Qiong;
Lei, Guang-Qing; Liu, Zhi-Jun; Chen, Dao-Feng; Chen, Jia-Kuan; Zhou, Tong-Shui. Department of Pharmacognosy, School of
Pharmacy, Fudan University, Shanghai, Peop. Rep. China. Chemical & Pharmaceutical Bulletin (2006), 54(1), 133-135.
Publisher: Pharmaceutical Society of Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN 144:447888
flavanone
Abstract
Two new flavanone glucosides, (2S)-homoeriodictyol 7,4'-di-O-β-D-glucopyranoside (4) and (2R)-eriodictyol

7,4'-di-O-β-D-glucopyranoside (5) were isolated from the branches and leaves of Viscum coloratum (KOMAR) NAKAI (Loranthaceae),
along with three known flavanone glucosides: (2S)-homoeriodictyol 7-O-β-D-glucopyranoside (1), (2S)-eriodictyol
7-O-β-D-glucopyranoside (2), and (2S)-naringenin 7-O-β-D-glucopyranoside (3). The structures of these compds. were elucidated using
spectroscopic methods. The antioxidant activities of these isolated compds. were evaluated by colorimetric methods based on their
scavenging effects on hydroxyl radicals and superoxide anion radicals, resp. All the compds. showed potent albeit varied degrees of
antioxidative activities and the structure-activity relationship is discussed.
Answer 457:
Syntheses of 1,5-benzothiazepines. Part XXIX. Syntheses and antimicrobial studies of

10-substituted-6a,7-dihydro-6H-7-(4-ethoxyphenyl)-6-phenyl[1]benzopyrano[3,4-c][1,5]benzothiazepines. Pant, Seema;
Sharma, Priyanka; Chandra, Hem; Pant, Umesh C. LBS Government P.G. College, Kotputli, India. Indian Journal of Heterocyclic
Chemistry (2006), 15(3), 289-290. Publisher: Prof. R. S. Varma, CODEN: IJCHEI ISSN: 0971-1627. Journal written in English.
Abstract
The reactions of 5-substituted-2-aminobenzenethiols, were carried out with the flavindogenide, 3-(4-ethoxybenzylidene)-flavanone in
parallel sets that is in acidic and basic media, to obtain
10-substituted-6a,7-dihydro-6H-7-(4-ethoxyphenyl)-6-Ph[1]benzopyrano[3,4-c][1,5]benzothiazepines. The structural assignments are
based on microestimations for the elements and IR, 1H NMR and mass spectral analyses. Antibacterial activity studies against
Escherichia coli and GFC, using Bacitracin as ref. compd., and antifungal studies against Aspergillus niger, A. flavus and Curvularia
lunata, using Mycostatin as the ref. compd., were carried out. All the compds. showed moderate antibacterial activity but significant
antifungal activity.
Answer 458:
Microbial transformations of flavanone and 6-hydroxyflavanone by Aspergillus niger strains. Kostrzewa-Suslow, Edyta;
Dmochowska-Gladysz, Jadwiga; Bialonska, Agata; Ciunik, Zbigniew; Rymowicz, Waldemar. Department of Chemistry, Agricultural
University, Wroclaw, Pol. Journal of Molecular Catalysis B: Enzymatic (2006), 39(1-4), 18-23. Publisher: Elsevier B.V., CODEN:
JMCEF8 ISSN: 1381-1177. Journal written in English. CAN 145:123081 AN 2006:366220 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Flavanone (1) and 6-hydroxyflavanone (2) were subjected to transformation by means of Aspergillus niger strains (one wild and three
UV mutants). For both substrates the biotransformation resulted in redn. of the carbonyl group (products 5 and 7) and
dehydrogenation at C-2 and C-3 (3 and 8). Addnl., for flavanone (1) redn. of C-4 together with hydroxylation at C-7 (6) and
dehydrogenation at C-2, C-3 along with hydroxylation at C-3 (4) were obsd.
Answer 459:
flavanone
Flavonoids from the pods of Millettia erythrocalyx. Sritularak, Boonchoo; Likhitwitayawuid, Kittisak. Department of
Pharmacognosy, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok, Thailand. Phytochemistry (Elsevier)
(2006), 67(8), 812-817. Publisher: Elsevier Ltd., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN
Abstract
From the pods of Millettia erythrocalyx, 2'-hydroxy-3,4-dimethoxy-[2'',3'':4',3']-furanochalcone,

2',3-dihydroxy-4-methoxy-4'-γ,γ-dimethylallyloxychalcone, (-)-(2S)-6,3',4'-trimethoxy-[2'',3'':7,8]-furanoflavanone,
3',4'-methylenedioxy-[2'',3'':7,8]-furanoflavonol and 6,3'-dimethoxy-[2'',3'':7,8]-furanoflavone were isolated, along with six other known
flavonoids. Their structures were elucidated through anal. of their spectroscopic data.
Answer 460:
Pinostrobin - an anti-leukemic flavonoid from Polygonum lapathifolium L. ssp. nodosum (Pers.) Dans. Smolarz, Helena D.;
Mendyk, Ewaryst; Bogucka-Kocka, Anna; Kocki, Janusz. Chief and Department of Pharmaceutical Botany, Medical University of
Lublin, Lublin, Pol. Zeitschrift fuer Naturforschung, C: Journal of Biosciences (2006), 61(1/2), 64-68. Publisher: Verlag der
Zeitschrift fuer Naturforschung, CODEN: ZNCBDA ISSN: 0939-5075. Journal written in English. CAN 144:445030 AN
Abstract
Aim of study: Search for plant compds. possessing anti-leukemic properties. Results: We have shown that 5-hydroxy-7-methoxy
flavanone (pinostrobin) isolated from Polygonum lapathifolium ssp. nodosum quickly penetrates through cytoplasm to the cellular
nucleus of the cultured cells, and gives intensive apoptotic response in stimulating leukemic cells in vitro. The no. of apoptotic cells
increased with the concn. of pinostrobin: 10 nM - 25% and 60%; 100 nM - 45% and 76%; 1 μM - 70% and 88% for Jurkat and HL60 cell
lines, resp. Conclusion: Pinostrobin may be considered as a good candidate for a leukemia chemopreventive agent.
Answer 461:
Sucrose-specific induction of the anthocyanin biosynthetic pathway in Arabidopsis. Solfanelli, Cinzia; Poggi, Alessandra;
Loreti, Elena; Alpi, Amedeo; Perata, Pierdomenico. Department of Crop Plant Biology, University of Pisa, Pisa, Italy. Plant
Abstract
Sugars act as signaling mols., whose signal transduction pathways may lead to the activation or inactivation of gene expression.
Whole-genome transcript profiling reveals that the flavonoid and anthocyanin biosynthetic pathways are strongly up-regulated following
sucrose (Suc) treatment. Besides mRNA accumulation, Suc affects both flavonoid and anthocyanin contents. We investigated the
effects of sugars (Suc, glucose, and fructose) on genes coding for flavonoid and anthocyanin biosynthetic enzymes in Arabidopsis
(Arabidopsis thaliana). The results indicate that the sugar-dependent up-regulation of the anthocyanin synthesis pathway is Suc
specific. An altered induction of several anthocyanin biosynthetic genes, consistent with in vivo sugar modulation of mRNA
accumulation, is obsd. in the phosphoglucomutase Arabidopsis mutant accumulating high levels of sol. sugars.
flavanone
Answer 462:
Characterization of a grapevine R2R3-MYB transcription factor that regulates the phenylpropanoid pathway. Deluc,
Laurent; Barrieu, Francois; Marchive, Chloe; Lauvergeat, Virginie; Decendit, Alain; Richard, Tristan; Carde, Jean-Pierre; Merillon,
Jean-Michel; Hamdi, Said. Unite Mixte de Recherche 619, Physiologie et Biotechnologie Vegetales, Institut National de la Recherche
Agonomique, Centre de Recherche de Bordeaux, Universite Bordeaux 1, Universite Bordeaux 2, Villenave d'Ornon, Fr. Plant
Abstract
The ripening of grape (Vitis vinifera) berry is characterized by dramatic changes in gene expression, enzymic activities, and metab.
that lead to the prodn. of compds. essential for berry quality. The phenylpropanoid metabolic pathway is one of the components
involved in these changes. In this study, the authors describe the cloning and functional characterization of VuMYB5a, a cDNA
isolated from a grape L. cv Cabernet Sauvignon berry library. VuMYB5a encodes a protein belonging to a small subfamily of
R2R3-MYB transcription factors. Expression studies in grapevine indicate that the VvMYB5a gene is mainly expressed during the
early steps of berry development in skin, flesh, and seeds. Overexpression of VvMYB5a in tobacco (Nicotiana tabacum) affects the
expression of structural genes controlling the synthesis of phenylpropanoid and impacts on the metab. of anthocyanins, flavonols,
tannins, and lignins. Overexpressing VvMYB5a induces a strong accumulation of several phenolic compds., including keracyanin
(cyanidin-3-rhamnoglucoside) and quercetin-3-rhamnoglucoside, which are the main anthocyanin and flavonol compds. in tobacco. In
addn., VvMYB5a overexpression increases the biosynthesis of condensed tannins and alters lignin metab. These findings suggest
that VvMYB5a may be involved in the control of different branches of the phenylpropanoid pathway in grapevine.
Answer 463:
Kinetic model for wastewater treatment: spectroscopic determination of pollutants. Luna-Pabello, V. M.; Pandiyan, T.;
Dominguez, A. E. Facultad de Quimica, Universidad Nacional Autonoma de Mexico, Mexico D.F., Mex. Research Journal of
Chemistry and Environment (2006), 10(1), 67-74. Publisher: Research Journal of Chemistry and Environment, CODEN: RJCEF7
(R))
Abstract
Agro-industry wastewater was degraded by biodegradability method and the results predict that the wastewater is easily biodegradable.
Furthermore, at different substrates concns., the wastewater undergoes two kinetic phases; for example, the oxygen consumption for
the oxidn. of carbon source compds. is proportional to first phase degrdn. rate (k1 = 3.9 × 10-3 mg/L⋅h); however, the oxygen
consumption and the second phase degrdn. rate (k2 = 0.8 × 10-3 mg/L⋅h) are disagreed; thus, a kinetic model is proposed to explain the
biodegrdn. process of the waste and compared with Monod and Alexander-diagrams. Furthermore, the low degrdn. rate of second
phase is explained by isolating the non-degradable compds. such as 4'-methoxy-5-hydroxy-7-acetyl flavanone, 2,4-diclorophenol,
4-chlorophenol, and 4-chloroethyl-1,3-benzenedithiol, which were detd. spectroscopically.
Answer 464:
Structure prerequisite for antioxidant activity of silybin in different biochemical systems in vitro. Varga, Zs.; Seres, I.;
flavanone
Nagy, E.; Ujhelyi, L.; Balla, G.; Balla, J.; Antus, S. Division of Nephrology, First Department of Medicine, Hung. Phytomedicine
(2006), 13(1-2), 85-93. Publisher: Elsevier GmbH, CODEN: PYTOEY ISSN: 0944-7113. Journal written in English. CAN
Abstract
Structural analogs (flavanone: 2-4 and flavone: 5 and 6, resp.) of silybin (1a) were synthesized and tested for inhibitory activity on
O⋅-2 release and PKC translocation in PMA-stimulated neutrophils as well as xanthine oxidase activity in order to identify the mol.
structures responsible for the antioxidant property of silybin. Concerning the prevention of hem-mediated oxidative modification of
LDL by silybin, the hydroxyl radical scavenging activity of its structural analogs was also detd. We demonstrated that the basic
skeleton of 1a (4) is responsible for its inhibitory activity on O⋅-2 release in PMA-stimulated neutrophils via inhibition of PKC
translocation, since introduction of a double bound and hydroxyl groups at C-5 and C-7 position (5 and 6) did not result in further
increase in inhibition of O⋅-2 release. It has been shown that the presence of the phenolic hydroxyl group at C-5 and C-7 of 1a is
essential for the inhibition of xanthine oxidase activity. Moreover, introduction of a double bond into the C-ring of 2 and 3, resulting in
flavone derivs. (5 and 6), markedly enhanced the antioxidant effect in all the tested systems. Finally, silybin (1a) and its flavone
derivs. (5 and 6) directly scavenged hydroxyl radicals as well. On the basis of these results it might be concluded that different
moiety of silybin is responsible for inhibition of overprodn. of O⋅-2 in stimulated neutrophils, xanthine oxidase activity, and for
prevention of hem-mediated oxidative modification of LDL.
Answer 465:
Bronchodilators and anti-inflammatory activity of flavone/flavanone derivatives. Kroeger, Edwin A. (University of Manitoba,
Can.). PCT Int. Appl. (2006), 17 pp. CODEN: PIXXD2 WO 2006030322 A2 20060323 Designated States W: AE, AG, AL, AM,
GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG,
NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN,
YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF,
BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2005-IB3591 20050913. Priority:
US 2004-611020 20040917. CAN 144:324843 AN 2006:332240 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))

WO 2006030322 A2 20060323 WO 2005-IB3591 20050913
WO 2006030322 A3 20060629
KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH,
PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN,
YU, ZA, ZM, ZW
US 2004-611020P P 20040917
flavanone
Abstract
Use of flavone/flavanone derivs. as bronchodilators and anti-inflammatory compds. to treat respiratory and nasal diseases. The
bronchodilator activity of 30 mg/kg 3,3'-dihydroxyflavone at i.v. was shown in dogs.
Answer 466:
Stereoisomeric separation of flavanones and flavanone-7-O-glycosides by capillary electrophoresis and determination of

interconversion barriers. Wistuba, Dorothee; Trapp, Oliver; Gel-Moreto, Nuria; Galensa, Rudolf; Schurig, Volker. Institut fuer
Organische Chemie, Universitaet Tuebingen, Tuebingen, Germany. Analytical Chemistry (2006), 78(10), 3424-3433. Publisher:
American Chemical Society, CODEN: ANCHAM ISSN: 0003-2700. Journal written in English. CAN 145:20108 AN 2006:326570
Abstract
The stereoisomeric sepn. of several flavanones and flavanone-7-O-glycosides was achieved with capillary electrophoresis by adding
native cyclodextrins or cyclodextrin derivs. to the background electrolyte. As an alternative method, micellar electrokinetic chromatog.
with sodium cholate as a chiral surfactant was used for the epimeric sepn. of two flavanone-7-O-glycosides. The effect of buffer
systems contg. mixts. of cyclodextrin with either sodium dodecyl sulfate or sodium cholate upon the chiral recognition of flavanones
and flavanone-7-O-glycosides as well as the variation of the background electrolyte (concn. of buffer and surfactant, pH value, org.
modifier), and its influence on the resoln. factor Rs was studied. Temp.- and pH-dependent enantiomerization or epimerization barriers
of several flavanones (naringenin, homoeriodictyol) and flavanone-7-O-glycosides (naringin, neohesperidin, prunin, narirutin) in basic
media (pH values of 9-11) were obsd. Interconversion profiles featuring characteristic plateau formation of the elution pattern were
obsd. at high pH and evaluated with the simulation software ChromWin to det. rate consts. k(T) and Eyring activation parameters,
ΔG#(T), ΔH#, and ΔS#.
Answer 467:
Effects of 8-prenylnaringenin on the hypothalamo-pituitary-uterine axis in rats after 3-month treatment. Christoffel, J.;
Rimoldi, G.; Wuttke, W. Division of Clinical and Experimental Endocrinology, Department of Obstetrics and Gynecology, University
of Goettingen, Goettingen, Germany. Journal of Endocrinology (2006), 188(3), 397-405. Publisher: Society for Endocrinology,
CODEN: JOENAK ISSN: 0022-0795. Journal written in English. CAN 144:425637 AN 2006:326047 CAPLUS (Copyright (C)
Abstract
Phytoestrogens are increasingly consumed in artificially high doses as herbal prepns. and nutritional supplements. The flavanone
8-prenylnaringenin (8PN) is a potent phytoestrogen, but its benefits and risks after long-term application are poorly identified.
Therefore, we tested two doses of 8PN and 17β-estradiol-3-benzoate (E2B) (EDs: 6⋅8 and 68⋅4 mg/kg body wt. (BW) of 8PN, and 0⋅17
and 0⋅7 mg/kg BW of 17β-estradiol (E2)) and compared their effects on uterine wt., pituitary hormones (LH, FSH and prolactin) and the
expression of estrogen-regulated genes and of estrogen receptor (ER)α and ERβ in the hypothalamus, pituitary and uterus. Both
doses of E2 and the high dose of 8PN suppressed serum LH and FSH, and stimulated serum prolactin levels, uterine wt., and
progesterone receptor, insulin-like growth factor I and complement protein C3 mRNA transcripts. In the preoptic and the mediobasal
areas of the hypothalamus, all treatments had negligible effects on ERα and ERβ and gonadotropin-releasing hormone (GnRH)
receptor gene expression, while ERβ and GnRH receptor transcripts in the anterior pituitary were reduced under both E2 doses and the
high 8PN dose. The mRNA concns. of the LHα and -β subunits in the pituitary were suppressed by E2 and 8PN. In summary, 8PN
flavanone
had very similar though milder effects than E2 on all tested parameters. Inhibition of climacteric complaints by E2 takes place in the
hypothalamus, where it inhibits the overactive GnRH pulse generator. Hence, 8PN may be used to inhibit climacteric symptoms
effectively. Human pharmacol. studies will show whether the stimulatory effect on the uterus that was found in the present animal
model would require the concomitant administration of progestins to prevent endometrial overstimulation.
Answer 468:
Synthesis of 1,5-benzothiazepines. Part XXX. Synthesis and antimicrobial studies of 10-substituted

6a,7-dihydro-6H-7-(4-fluorophenyl)-6-phenyl[1]benzopyrano[3,4-c][1,5]benzothiazepines. Pant, Umesh C.; Chandra, Hem;
Goyal, Shweta; Sharma, Priyanka; Pant, Seema. Department of Chemistry, University of Rajasthan, Jaipur, India. Indian
Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (2006), 45B(3), 752-757. Publisher: National
Institute of Science Communication and Information Resources, CODEN: IJSBDB ISSN: 0376-4699. Journal written in English.
Abstract
Flavindogenide, 3-(4-fluorobenzylidene)flavanone was reacted with six 5-substituted 2-aminobenzenethiols, the substituents being F, Cl,
Br, Me, MeO, and EtO, to obtain a series of 10-substituted
6a,7-dihydro-6H-7-(4-fluorophenyl)-6-phenyl[1]benzopyrano[3,4-c][1,5]benzothiazepines. The products are characterized by elemental
anal. and IR, 1H NMR, 19F NMR, and mass spectra. The synthesized compds. showed antimicrobial activity against the bacteria
Escherichia coli and GFC (Alteromonas tetraodonis, a new Gram-neg. bacteria family) and fungi, Aspergillus niger, A. flavus and
Curvularia lunata.
Answer 469:
Temporal and spatial expression of genes involved in anthocyanin biosynthesis during sweet potato (Ipomoea batatas [L.[
Lam.) root development. Lalusin, Antonio G.; Ohta, Masaru; Fujimura, Tatsuhito. Laboratory of Plant Genetic Engineering,
Graduate School of Life and Environmental Sciences, University of Tsukuba, Tennoudai 1-1-1, Tsukuba City, Ibaraki, Japan.
International Journal of Plant Sciences (2006), 167(2), 249-256. Publisher: University of Chicago Press, CODEN: IPLSE2 ISSN:
Abstract
To elucidate the gene regulation of pigmentation in sweet potato, expressions of the genes involved in anthocyanin biosynthesis were
investigated in correlation with the accumulation of the anthocyanins during plant development. Fragments of the anthocyanin
biosynthetic pathway genes involved in the central flavonoid pathway, including those for chalcone synthase (CHS), chalcone
isomerase (CHI), flavone 3-hydroxylase (F3H), dihydroflavonol 4-reductase (DFR), anthocyanidin synthase (ANS), and
UDPG-flavonoid-3-O-glucosyltransferase (UF3GT) were investigated in sweet potato, and their expressions were characterized in
various tissues and developmental stages in both purple- and yellow-fleshed varieties. Transcription patterns of the anthocyanin
biosynthetic genes show accumulation at the early stages of root development (10-30 d after planting), followed by a decline. The
anthocyanin biosynthetic genes were expressed throughout all stages of root development, wherein their expressions were activated at
the stages corresponding to anthocyanin accumulation. Quantification of total anthocyanin content in various sweet potato tissues
showed that the anthocyanin content of the purple-fleshed variety was highly concd. in all root types except in the lateral roots, while
in the yellow-fleshed variety, anthocyanin content was highest in the pigmented roots. The anthocyanin content at the different
developmental stages of the sweet potato plant is highest during the early stages of development (10-30 d after planting), which is in
accordance with the transcription levels of the anthocyanin biosynthetic genes.
Answer 470:
flavanone
Research progress in the chemistry of metallic complexes of flavanones. Zhao, Bing; Xu, Qing-hai; Duan, Li-ying. Sch.
Pharmaceutical Eng., Shenyang Pharmaceutical Univ., Shenyang, Peop. Rep. China. Huaxue Shiji (2006), 28(3), 141-143.
Publisher: Huaxue Shiji Bianjibu, CODEN: HUSHDR ISSN: 0258-3283. Journal; General Review written in Chinese. CAN
Abstract
A review. The present research status, the synthesizing and testing methods, pharmacol. functions on some metallic complexes of
flavanones were reviewed in this paper.
Answer 471:
Effect of basic properties of MgO on the heterogeneous synthesis of flavanone. Liu, Zheng; Cortes-Concepcion, Jose A.;
Mustian, Michael; Amiridis, Michael D. Department of Chemical Engineering, University of South Carolina, Columbia, SC, USA.
Applied Catalysis, A: General (2006), 302(2), 232-236. Publisher: Elsevier B.V., CODEN: ACAGE4 ISSN: 0926-860X. Journal
Abstract
The effect of the surface basicity of MgO on the heterogeneous synthesis of flavanone from benzaldehyde and
2'-hydroxyacetophenone was examd. through a series of MgO samples modified with different anions. CO2 temp. programmed
desorption (TPD) was used to characterize the basic properties of these samples. The results indicate that basic sites with different
strengths exist on the MgO surface. Introduction of different anions completely eliminates the weak basic sites (i.e., those desorbing
CO2 in the 300-420 K range) and reduces substantially the no. of medium strength sites (i.e., those desorbing CO2 in the 420-650 K
range). In contrast, no substantial effect was obsd. - with the exception of the chloride-treated sample - on the stronger basic sites
(i.e., those desorbing CO2 above 650 K). A strong correlation was obsd. between the no. of basic sites of "medium" strength and the
catalytic activity of these samples for the heterogeneous synthesis of flavanone. These sites are most likely involved in the
activation of 2'-hydroxyacetophenone for the Claisen-Schmidt condensation with benzaldehyde, which represents the first step in the
synthesis of flavanone.
Answer 472:
Down-regulation of the strawberry Bet v 1-homologous allergen in concert with the flavonoid biosynthesis pathway in
colorless strawberry mutant. Hjernoe, Karin; Alm, Rikard; Canback, Bjorn; Matthiesen, Rune; Trajkovski, Karin; Bjork, Lars;
Roepstorff, Peter; Emanuelsson, Cecilia. Department of Biochemistry and Molecular Biology, University of Southern Denmark,
Odense, Den. Proteomics (2006), 6(5), 1574-1587. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: PROTC7 ISSN:
Abstract
Proteomic screening of strawberry (Fragaria ananassa) yielded a 58% success rate in protein identification in spite of the fact that no
genomic sequence is available for this species. This was achieved by a combination of MALDI-MS/MS de novo sequencing of
flavanone
double-derivatized peptides and indel-tolerant searching against local protein databases built on both EST and full-length nucleotide
sequences. The amino acid sequence of a strawberry allergen, homologous to the well-known major birch pollen allergen Bet v 1, was
partially detd. This strawberry allergen, named Fra a 1 according to the nomenclature for allergen proteins, showed sequence identity
of 54 and 77%, resp., with corresponding allergens from birch and apple. Differential expression, as evaluated by 2-D DIGE, occurred
in 10% of protein spots when red strawberries were compared to a colorless (white) strawberry mutant. White strawberries, known to be
tolerated by individuals affected by allergy, were virtually free from the strawberry allergen. Also several enzymes in the pathway for
biosynthesis of flavonoids, to which the red color pelargonidin belongs, were down-regulated. This approach to assess differential
protein expression without access to genomic sequence information can also be applied to other crop plants and phenotypic traits.
Answer 473:
Synthesis of Abyssinone II and related compounds as potential chemopreventive agents. Moriarty, Robert M.; Grubjesic,
Simonida; Surve, Bhushan C.; Chandersekera, Susantha N.; Prakash, Om; Naithani, Rajesh. Department of Chemistry, University
of Illinois at Chicago, Chicago, USA. European Journal of Medicinal Chemistry (2006), 41(2), 263-267. Publisher: Elsevier B.V.,
CODEN: EJMCA5 ISSN: 0223-5234. Journal written in English. CAN 144:467925 AN 2006:274159 CAPLUS (Copyright (C)
Abstract
A facile and efficient approach to the synthesis of prenylated flavonoids as potential chemopreventive agents was described. This
features the synthesis of prenyl halide, prenylation of p-hydroxybenzaldehyde, formation of prenylated polyhydroxychalcone and
cyclization of prenylated polyhydroxychalcone to (±)-abyssinone II I (R3 = H), abyssinone cyclic analog II and flavanol I (R3 = OH)
starting from isoprene. The structures of all three compds. were characterized by NMR, IR and mass spectroscopy and
(±)-abyssinone II was assayed for aromatase inhibition.
OH
HO O Me
Me
R3
O I
Me
O
Me
HO O
O II
Answer 474:
flavanone
Antitumor activity of some natural flavonoids and synthetic derivatives on various human and murine cancer cell lines.
Cardenas, Mariano; Marder, Mariel; Blank, Viviana C.; Roguin, Leonor P. Facultad de Farmacia y Bioquimica, Instituto de Quimica y
Fisicoquimica Biologicas (UBA-CONICET), Buenos Aires, Argent. Bioorganic & Medicinal Chemistry (2006), 14(9), 2966-2971.
Publisher: Elsevier B.V., CODEN: BMECEP ISSN: 0968-0896. Journal written in English. CAN 144:460302 AN 2006:263188
Abstract
The effect of various natural flavonoids, cinnamic acid derivs., and a series of synthetic flavones on cell proliferation was evaluated
in vitro in a panel of established human and murine tumor cell lines. The most potent antiproliferative agents were caffeic acid Bu
ester (12) > 2'-nitroflavone (26) > caffeic acid Et ester (11) .apprx. 2',6-dinitroflavone (27) > apigenin (3) > 3'-bromoflavone (20) .apprx.
2'-fluoro-6-bromoflavone (31). Some compds. showed a moderate effect, the order of cytotoxic activities being chrysin (2) >
2'-fluoro-6-chloroflavone (30) .apprx. 2'-chlorochrysin (32) > α-naphthoflavone (7) > β-naphthoflavone (8) .apprx.6-chloroflavone (14)
.apprx. 6-bromoflavone (15) .apprx. 4'-nitroflavone (23). A structure-activity relationship anal. of each group of compds. was
performed. None of the natural or synthetic compds. tested affected the proliferation of epithelial cells derived from normal
mammary gland of mice or fibroblastic cells from mouse embryo, suggesting a selective action against tumor cells.
Answer 475:
Difference in plasma metabolite concentration after ingestion of lemon flavonoids and their aglycones in humans. Miyake,
Yoshiaki; Sakurai, Chika; Usuda, Mika; Fukumoto, Syuichi; Hiramitsu, Masanori; Sakaida, Kazuhiro; Osawa, Toshihiko; Kondo, Kazuo.
Faculty of Human Wellness, Tokaigakuen University, Nagoya, Japan. Journal of Nutritional Science and Vitaminology (2006),
52(1), 54-60. Publisher: Center for Academic Publications Japan, CODEN: JNSVA5 ISSN: 0301-4800. Journal written in English.
Abstract
The concns. of metabolites in human plasma after ingestion of flavanone glycosides (FG) and their aglycons (FA) in lemon were
examd. FG consisting abundantly of eriocitrin were prepd. from lemon peel and FA consisting abundantly of eriodictyol were prepd.
from FG by treatment with β-glucosidase. Eriodictyol, homoeriodictyol, and hesperetin in plasma up to 4 h after ingestion of FG with
water or FA with water by subjects were not detected in plasma of non-enzyme treatment but in plasma after treatment with
β-glucronidase and sulfatase. Metabolites in plasma after ingestion of FG and FA in humans were shown to exist as the glucuro-
and/or sulfo-conjugates of eriodictyol, homoeriodictyol, and hesperetin. After ingestion of FA, the concn. of metabolites in plasma
exhibited a high max. peak at 1 h. The AUC (area under the blood concn. time curve) level of metabolites of FA was higher than that
of FG. FA were suggested to be absorbed faster and in higher amts. than FG. The AUC of metabolites in subject plasma after
ingestion of FG with flavonoid-depleted lemon juice was shown to change to a low level in comparison with that of FG with water. The
max. concn. peak of metabolites in plasma was faster at 0.5 h than FA with water but the AUC level was similar to FA with water, when
subjects ingested FA with vodka (40% ethanol). The absorption hour of FG and FA was shown to be affected by the co-existing soln.
Answer 476:
Inhibitory effect of ponciretin on Helicobacter pylori VacA toxin-induced vacuolation in HeLa cells. Kim, Jong-Mi; Shin,
Ji-Eun; Bae, Eun-Ah; Han, Myung Joo; Kim, Dong-Hyun. College of Pharmacy, Kyung Hee University, Seoul, S. Korea. Journal
of Microbiology and Biotechnology (2006), 16(1), 46-51. Publisher: Korean Society for Microbiology and Biotechnology, CODEN:
JOMBES ISSN: 1017-7825. Journal written in English. CAN 145:180272 AN 2006:251887 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
flavanone
Abstract
The inhibitory effects of flavanone derivs. on Helicobacter pylori (HP) growth, infection and VacA toxin-induced vacuolation were
investigated. Among flavanones tested, ponciretin potently inhibited the growth of HP with a MIC value of 0.01 mg/mL and VacA
toxin-induced vacuolation in HeLa cells with IC50 value of 0.078 mM. However, other flavanones inhibited neither HP growth nor VacA
toxin-induced vacuolation. All flavanones tested did not inhibit HP infection to KATO III cells. Ponciretin also inhibited activation of
procaspase-3 to caspase-3 in HeLa cell induced by HP VacA toxin, but did not affect Bax and Bcl-2 protein levels. These findings
indicate that ponciretin inhibits growth as well as vacuolation by HP VacA toxin, which induces cell death via proteolytic activation of a
cascade of caspases.
Answer 477:
Selective ABTS radical-scavenging activity of prenylated flavonoids from Cudrania tricuspidata. Lee, Byong Won; Lee, Jin
Hwan; Gal, Sang Wan; Moon, Yea Hwang; Park, Ki Hun. Division of Applied Life Science (BK21 Program), Department of Agricultural
Chemistry, Institute of Agriculture & Life Sciences, Gyeongsang National University, Jinju, S. Korea. Bioscience, Biotechnology,
and Biochemistry (2006), 70(2), 427-432. Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry, CODEN:
BBBIEJ ISSN: 0916-8451. Journal written in English. CAN 145:206376 AN 2006:240911 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
The antioxidative properties of five prenylated flavonoids, including new flavanone (2), from the root bark of Cudrania tricuspidata
were examd. against the ABTS, DPPH, and hydroxyl radicals. In most of the assays to det. their antioxidative properties, the ABTS
activity was strongly correlated with DPPH because both methods are responsible for the same chem. property of hydrogen- or
electron-donation to the antioxidant. On the other hand, the prenylated flavonoids (1-5) acted differently with both methods; namely,
all the prenylated flavonoids strongly scavenged the ABTS radical (IC50 < 10 μM), while they were inactive against the DPPH radical
(IC50 > 300 μM). Even though isolated 5,7,2',4',-tetrahydroxy-6,5'-diprenylflavanone (3) showed weak reducing power (746 mV) by
cyclic voltammetry when compared to quercetin (394 mV), both had similar ABTS activity (IC50 < 5 μM).
Answer 478:
Thermal analysis study of flavonoid solid dispersions having enhanced solubility. Kanaze, F. I.; Kokkalou, E.; Niopas, I.;
Georgarakis, M.; Stergiou, A.; Bikiaris, D. Department of Pharmacy, School of Health Sciences, Aristotle University of
Thessaloniki, Thessaloniki, Greece. Journal of Thermal Analysis and Calorimetry (2006), 83(2), 283-290. Publisher: Springer,
CODEN: JTACF7 ISSN: 1388-6150. Journal written in English. CAN 144:337781 AN 2006:232700 CAPLUS (Copyright (C)
Abstract
Purposes of this paper were to prep. and study new drug delivery systems for both flavanone glycosides and their aglycons based on
solid-dispersion systems. These compds. are poor water sol. drugs, so an enhancement of their dissoln. is a high priority.
Solid-dispersion systems were prepd. using PVP, PEG and mannitol as drug carrier matrixes. Characterizations of these dispersions
were done by differential scanning calorimeter (DSC) and x-ray diffraction (XRD). The glass transition (Tg) temp. of PVP was only
recorded in the DSC thermograms of PVP solid-dispersions of both flavanone glycosides and their aglycons, while in case of PEG and
mannitol solid-dispersions endotherms of both glycosides and aglycons were noticed with low peak intensity, indicating that high
percent of drug is in amorphous state. The XRD patterns of all PVP solid-dispersions of aglycons show typical amorphous materials,
flavanone
but XRD patterns of their glycosides reveal the presence of cryst. material. However, in all solid dispersions shifts in Tg of PVP as
well as Tm of PEG were obsd., indicating the existence of some interactions between drugs and matrixes. SEM and TEM microscopy
revealed that PVP/aglycon flavanone compds. are nanodispersed systems while all the other solid dispersions are microcryst.
dispersions. The soly. of both flavanone glycosides and their aglycons was directly affected by the new phys. state of solid
dispersions. Due to the amorphous drug state or nano-dispersions in PVP matrixes, the soly. was enhanced and found to be 100% at
pH 6.8 in the nano-dispersion contg. 20 mass% of aglycons. Also soly. enhancement was occurred in solid dispersions of PEG and
mannitol, but it was lower than that of PVP nano-dispersions due to the presence of the drug compds. in cryst. state in both matrixes.
Answer 479:
High-performance liquid chromatographic enantioseparations on capillary columns containing monolithic silica modified
with amylose tris(3,5-dimethylphenylcarbamate). Chankvetadze, Bezhan; Yamamoto, Chiyo; Kamigaito, Masami; Tanaka,
Nobuo; Nakanishi, Kazuki; Okamoto, Yoshio. Molecular Recognition and Separation Science Laboratory, School of Chemistry, Tbilisi
State University, Tbilisi, Georgia. Journal of Chromatography, A (2006), 1110(1-2), 46-52. Publisher: Elsevier B.V., CODEN:
JCRAEY ISSN: 0021-9673. Journal written in English. CAN 144:460010 AN 2006:228895 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Monolithic capillary columns contg. native silica were modified by in situ coating with amylose tris(3,5-dimethylphenylcarbamate) and
applied for enantiosepns. in capillary liq. chromatog. Capillary columns were examd. for 10 std. racemic compds. to compare the
performance of monolithic silica columns with the common, 4.6 mm I.D. HPLC columns packed with particulate silica. The effects of
polysaccharide coating and of the linear velocity of the mobile phase on peak performance were studied. Enantiosepns. with an anal.
time <1 min were achieved for some chiral analytes.
Answer 480:
Error-based nonlinear partial least squares method embedded least squares support vector machine and its application to
quantitative structure-activity relationships. Li, Jian; Chen, Dezhao; Cheng, Zhong; Ye, Ziping. Department of Chemical
Engineering, Zhejiang University, Hangzhou, Peop. Rep. China. Fenxi Huaxue (2006), 34(2), 263-266. Publisher: Kexue
Chubanshe, CODEN: FHHHDT ISSN: 0253-3820. Journal written in Chinese. CAN 144:266504 AN 2006:223751 CAPLUS
Abstract
A new nonlinear partial least squares algorithm embedded least squares support vector machine (LSSVM) into the regression framework
of partial least squares(PLS) method was proposed. In this approach, LSSVM was used to fit the nonlinear inner relations between PLS
components, thus a multi-input multi-output nonlinear modeling task was decompd. into linear outer relations and simple nonlinear inner
relations that were performed by a no. of single-input single-output LSSVM models. By using the universal approxn. property of
LSSVM, the PLS modeling method was generalized to a non-linear framework. Subsequently, to increase PLS components
interpretative capability, the error-based wts. updating procedure in the PLS input outer model was deduced and implemented in the
LSSVM-PLS regression framework. Finally, the EB-LSSVM-PLS was applied to quant. structure-activity relationships modeling of
flavanone compd. Compared with the other three approach partial-east squares regression (PLSR), EB-neural network (NN) PLS and
LSSVM, the EB-LSSVM-PLS approach has better prediction performance and stability.
Answer 481:
flavanone
Citrus paradisi and Citrus sinensis flavonoids: Their influence in the defense mechanism against Penicillium digitatum.
Ortuno, A.; Baidez, A.; Gomez, P.; Arcas, M. C.; Porras, I.; Garcia-Lidon, A.; Del Rio, J. A. Departamento de Biologia Vegetal
(Fisiologia Vegetal), Facultad de Biologia, Universidad de Murcia, Murcia, Spain. Food Chemistry (2006), 98(2), 351-358.
Publisher: Elsevier B.V., CODEN: FOCHDJ ISSN: 0308-8146. Journal written in English. CAN 145:6987 AN 2006:222311
Abstract
Citrus peel is rich in flavanone glycosides and polymethoxyflavones. In view of their importance for industrial application as well as
for their pharmacol. properties, their content was analyzed in the mature fruits of several C. paradisi (grapefruit) and C. sinensis
(orange) varieties, with a view to select the most interesting for isolation. The results shows that the Star Ruby grapefruit and the
Sanguinelli orange stand out for their high contents of naringin and hesperidin, resp. The presence of the polymethoxyflavones
nobiletin, heptamethoxyflavone and tangeretin, could be ascertained in all the grapefruit varieties analyzed. Higher
polymethoxyflavone levels were recorded in orange, with Valencia Late showing the greatest nobiletin, sinensetin and tangeretin
contents and Navelate the highest heptamethoxyflavone levels. An in vitro study revealed that these compds. acted as antifungal
agents against Penicillium digitatum, the polymethoxyflavones being more active than the flavanones in this respect. The possible
participation of these phenolic compds. in the defense mechanism of Citrus against P. digitatum is discussed.
Answer 482:
Additive genetic variation of secondary and primary metabolites in mountain birch. Haviola, Sanna; Saloniemi, Irma;
Ossipov, Vladimir; Haukioja, Erkki. Dept of Biology, Univ. of Turku, Turku, Finland. Oikos (2006), 112(2), 382-391. Publisher:
Blackwell Publishers Ltd., CODEN: OIKSAA ISSN: 0030-1299. Journal written in English. CAN 146:23564 AN 2006:219232
Abstract
Evolutionary adaptations require genetic variation in the traits concerned. Mountain birch populations suffer from regular autumnal
moth defoliations that affect tree survival and growth. Earlier studies have found that birch individuals show clear differences in their
leaf chem., which may be relevant to herbivore performance. A large part of this variation is assumed to be genetic, since quant.
differences between trees remain the same in different years. The authors estd. the genetic parameters of several herbivory-related
chem. compds. The material consisted of 30 mature wild trees and their progenies. The authors treated the data both as half-sib and
full-sib families, and calcd. parent-offspring comparisons as well. The compds. included 12 individual phenolics, 5 carbohydrates and
16 protein-bound amino acids. For comparison, the authors also analyzed the wt. and germination percent of seeds and the height of
seedlings. Two of the most abundant phenylpropanoids (chlorogenic acid and kaempferol-3-O-α-L-rhamnopyranoside) showed
significant genetic variation, but this was not true of all individual phenolic compds. Amino acids had less genetic variation than
phenolic compds. The high genetic variation of the phenolic compds. indicates that the mountain birch is able to evolve its
phenol-based resistance.
Answer 483:
Two new dihydroflavanoids from Patrinia villosa Juss. Peng, Jin Yong; Fan, Guo Rong; Wu, Yu Tian. Shanghai Key
Laboratory for Pharmaceutical Metabolite Research, School of Pharmacy, Second Military Medical University, Shanghai, Peop. Rep.
China. Chinese Chemical Letters (2006), 17(2), 218-220. Publisher: Chinese Chemical Society, CODEN: CCLEE7 ISSN:
flavanone
Abstract
Two new dihydroflavonoids were obtained from the traditional Chinese medicinal herb Patrinia villosa Juss. Their structures were
elucidated as (2S)-5, 7, 2', 6'-tetrahydroxy-6, 8-di (γ, γ-dimethylallyl) flavanone (1) and (2S)-5, 7, 2', 6'-tetrahydroxy-6-lavandulylated
flavanone (2) by spectroscopic methods including UV, IR, HR-TOF-MS, 1D NMR and 2D NMR techniques.
Answer 484:
Synthesis and characterization of PEG-scutellarin conjugates, a potential PEG ester prodrug for the oral delivery of
scutellarin. Zhou, Qing Song; Jiang, Xue Hua; Yu, Jia Rui; Li, Ke Jia. West China School of Pharmacy, Sichuan University,
Chengdu, Peop. Rep. China. Chinese Chemical Letters (2006), 17(1), 85-88. Publisher: Chinese Chemical Society, CODEN:
CCLEE7 ISSN: 1001-8417. Journal written in English. CAN 146:163331 AN 2006:218675 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Highly water sol. esters of scutellarin I with variable mol. wt. polyethylene glycol (PEG) were prepd. via PEGylation. The
physicochem. properties and the stabilities under different conditions were investigated. By PEG modification, water soly. and
desirable partition coeff. of scutellarin were greatly increased. The results showed that these conjugates were potential prodrugs for
the oral delivery of scutellarin.
OH
O
O O O
PEG
HO
HO
OH
OH OH O I
Answer 485:
Heterologous Expression of Two Gentian Cytochrome P450 Genes can Modulate the Intensity of Flower Pigmentation in
Transgenic Tobacco Plants. Nakatsuka, Takashi; Nishihara, Masahiro; Mishiba, Keiichiro; Yamamura, Saburo. Iwate
Biotechnology Research Center, Kitakami, Iwate, Japan. Molecular Breeding (2006), 17(2), 91-99. Publisher: Springer, CODEN:
MOBRFL ISSN: 1380-3743. Journal written in English. CAN 146:41986 AN 2006:194769 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Two different heterologous expression systems, microsomal fractions of Saccharomyces cerevisiae and transgenic tobacco plants,
were used to investigate the enzymic activities of flavonoid 3'-hydroxylase (GtF3'H) and flavone synthase II (GtFSII) homologues
flavanone
isolated from gentian petals. Recombinant GtF3'H expressed in yeast showed hydroxylation activities in the 3' position with several
flavonoid substrates, while recombinant GtFSII was able to produce flavone from flavanone. GtF3' H-expressing transgenic tobacco
plants showed a slight increase in anthocyanin content and flower color intensity, and conversion of the flavonol quercetin from
kaempferol. On the other hand, GtFSII-expressing plants showed a remarkable redn. in anthocyanin content and flower color intensity,
and addnl. accumulation of flavone, esp. luteolin derivs. We demonstrated that two cytochrome P450s from gentian petals have F3'H
and FSII enzymic activities both in vitro and in vivo, and might therefore be useful in modification of flower color using genetic
engineering.
Answer 486:
Functional expression of a P450 flavonoid hydroxylase for the biosynthesis of plant-specific hydroxylated flavonols in
Escherichia coli. Leonard, Effendi; Yan, Yajun; Koffas, Mattheos A. G. Department of Chemical and Biological Engineering,
University at Buffalo, the State University of New York, Buffalo, NY, USA. Metabolic Engineering (2006), 8(2), 172-181.
Publisher: Elsevier, CODEN: MEENFM ISSN: 1096-7176. Journal written in English. CAN 144:466608 AN 2006:181868
Abstract
Flavonols are plant polyphenolic compds. that belong to the class of mols. collectively known as flavonoids. Because of their
demonstrated health benefits towards a wide array of human pathol. conditions, a great interest has emerged for their biosynthesis
from well-characterized microbial hosts. We present the functional expression in Escherichia coli of a plant P 450 flavonoid
3',5'-hydroxylase (F3'5'H) as a fusion protein with a P 450 reductase. This expression allowed metabolic engineering of E. coli to
produce the flavonol kaempferol and the 3',4' B-ring hydroxylated flavonol quercetin from the p-coumaric acid precursor by
simultaneously co-expressing the fusion protein with 4-coumaroyl:CoA-ligase (4CL), chalcone synthase (CHS), chalcone isomerase
(CHI), flavanone 3β-hydroxylase (FHT) and flavonol synthase (FLS). Biosynthesis of the B-ring tri-hydroxylated flavonol myricetin
from the engineered strains was accomplished when flavanones rather than phenylpropanoid acids were used as precursor mols.
Cultivation of the recombinant strains in rich medium increased the synthesis of all flavonoids with the exception of myricetin. The
present work opens the possibility of the future prodn. of several other hydroxylated flavonoid mols. in E. coli.
Answer 487:
Skin lighting and antiaging compositions containing a flavonoid compound and vitamin B3. Chen, Minghua; Sun, Peiwen;
Date, Akira; Yuyama, Etsuko; Bissett, Donald Lynn. (The Procter & Gamble Company, USA). PCT Int. Appl. (2006), 32 pp.
KG, KM, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT,
RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States
RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE,
SN, TD, TG. Patent written in English. Application: WO 2005-US25346 20050715. Priority: US 2004-590559 20040723. CAN

WO 2006020164 A1 20060223 WO 2005-US25346 20050715
flavanone
DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KP, KR, KZ,
LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL,
PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU,
ZA, ZM, ZW
CN 1988879 A 20070627 CN 2005-80024942 20050715
EP 1833456 A1 20070919 EP 2005-772259 20050715
JP 2008507523 T 20080313 JP 2007-522609 20050715
US 2004-590559P P 20040723
WO 2005-US25346 W 20050715
Abstract
The present invention is directed to a skin case compn. comprising: (1) from about 0.001% to about 10% of a flavonoid compd.; (2)
from about 0.01% to about 15% of a vitamin B3 compd.; and (3) a dermatol. acceptable oil-in-water carrier comprising at least about
2% by wt. of the entire compn. of an oil component; wherein the compn. is substantially free of titanium dioxide. The present
invention is also directed to a method of providing skin lightening benefit and anti-aging benefit comprising the steps of applying to the
skin the aforementioned compn.
Answer 488:
Quantitative modeling (QSPR) of flavonoids from Croatian propolis. Smolcic-Bubalo, Asja; Mornar, Ana; Jasprica, Ivona;
Medic-Saric, Marica. Department of Pharmaceutical Chemistry, Faculty of Pharmacy and Biochemistry, University of Zagreb,
Zagreb, Croatia. Periodicum Biologorum (2005), 107(4), 457-464. Publisher: Hrvatsko Prirodoslovno Drustvo, CODEN: PDBIAD
SciFinder (R))
Abstract
Background and Purpose: Flavonoids and phenolic acids are two groups of recently popular phytochems. The most concd. source of
those plant polyphenols is propolis - a natural product made by honeybees. Material and Methods: In this paper we focus on the
nonempirical structure-property anal. of a certain no. of flavonoids and phenolic acids, usually present in Croatian propolis. Using mol.
modeling procedures, we investigated the relationships between structure and properties of these compds. Topol. indexes used for
correlation anal. include Wiener index, W, valence connectivity index, χv, Balaban index, J, information-theoretic index, I, and Schultz
Index, MTI. All indexes were calcd. using TAM software. Investigated physicochem. properties were mol. wt. (M.w.), van der Waals
vol. (Vw) and lipophilicity (log P). Van der Waals vol. was calcd. according to the method described by Moriguchi and log P values
were calcd. using ALOGPs program. Result and Conclusion: The best QSPR models were obtained using Wiener index and valence
connectivity index. Together with the indexes mentioned above, information-theoretic index also showed good correlation with certain
physicochem. properties.
flavanone
Answer 489:
Silymarin and silibinin cause G1 and G2-M cell cycle arrest via distinct circuitries in human prostate cancer PC3 cells: a
comparison of flavanone silibinin with flavanolignan mixture silymarin. Deep, G.; Singh, R. P.; Agarwal, C.; Kroll, D. J.;
Agarwal, R. Department of Pharmaceutical Sciences, School of Pharmacy, University of Colorado Health Sciences Center,
Denver, CO, USA. Oncogene (2006), 25(7), 1053-1069. Publisher: Nature Publishing Group, CODEN: ONCNES ISSN:
Abstract
Here, we assessed and compared the anticancer efficacy and assocd. mechanisms of silymarin and silibinin in human prostate cancer
(PCA) PC3 cells; silymarin is comprised of silibinin and its other stereoisomers, including isosilybin A, isosilybin B, silydianin,
silychristin and isosilychristin. Silymarin and silibinin (50-100 μg/mL) inhibited cell proliferation, induced cell death, and caused G1 and
G2-M cell cycle arrest in a dose/time-dependent manner. Mol. studies showed that G1 arrest was assocd. with a decrease in cyclin D1,
cyclin D3, cyclin E, cyclin-dependent kinase (CDK)4, CDK6 and CDK2 protein levels, and CDK2 and CDK4 kinase activity, together
with an increase in CDK inhibitors (CDKIs) Kip1/p27 and Cip1/p21. Further, both agents caused cytoplasmic sequestration of cyclin
D1 and CDK2, contributing to G1 arrest. The G2-M arrest by silibinin and silymarin was assocd. with decreased levels of cyclin B1,
cyclin A, pCdc2 (Tyr15), Cdc2, and an inhibition of Cdc2 kinase activity. Both agents also decreased the levels of Cdc25B and cell
division cycle 25C (Cdc25C) phosphatases with an increased phosphorylation of Cdc25C at Ser216 and its translocation from nucleus
to the cytoplasm, which was accompanied by an increased binding with 14-3-3β. Both agents also increased checkpoint kinase (Chk)2
phosphorylation at Thr68 and Ser19 sites, which is known to phosphorylate Cdc25C at Ser216 site. Chk2-specific small interfering
RNA largely attenuated the silymarin and silibinin-induced G2-M arrest. An increase in the phosphorylation of histone 2AX and ataxia
telangiectasia mutated was also obsd. These findings indicate that silymarin and silibinin modulate G1 phase cyclins-CDKs-CDKIs for
G1 arrest, and the Chk2-Cdc25C-Cdc2/cyclin B1 pathway for G2-M arrest, together with an altered subcellular localization of crit. cell
cycle regulators. Overall, we obsd. comparable effects for both silymarin and silibinin at equal concns.
by wt., suggesting that silibinin could be a major cell cycle-inhibitory component in silymarin. However, other silibinin
stereoisomers present in silymarin also contribute to its efficacy, and could be of interest for future investigation.
Answer 490:
Preparation of flavanone glycosides as immunosuppressant. Guo, Zijian; Yang, Xiaoliang; Xu, Qiang; Sun, Yang; Zhang,
Zichao. (Nanjing University, Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 20 pp. CODEN:

CN 1594346 A 20050316 CN 2004-10041063 20040623
CN 2004-10041063 20040623
Abstract
flavanone
Title compds., e.g. I, are prepd. by treating hydroxyflavanone with 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate or
2,3,4,6-tetraacetyl-D-glucopyranosyl trichloroacetimidate in CH2Cl2 in the presence of trimethylsilyl triflate at -42°--78° followed by
deprotection with NH3 in MeOH. I was prepd. and showed immunosuppressant activity comparable to that of astilbin.
O Ph
O OH
O
Me OH
OH I
Answer 491:
A selective transformation of flavanones to 3-bromoflavones and flavones under microwave irradiation. Zhou, Zhongzhen;
Zhao, Peiliang; Huang, Wei; Yang, Guangfu. Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, College of
Chemistry, Central China Normal University, Wuhan, Peop. Rep. China. Advanced Synthesis & Catalysis (2006), 348(1 + 2),
63-67. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: ASCAF7 ISSN: 1615-4150. Journal written in English. CAN
Abstract
This paper presents the first report of a highly selective transformation of flavanones to 3-bromoflavones or flavones by microwave
irradn. of the corresponding flavanone reactants and N-bromosuccinimide (NBS) in the presence of a catalytic amt. of
2,2'-azobis(isobutyronitrile) (AIBN). The combination of good to excellent yields, shorter reaction time (10 min), and high levels of
functional group compatibility make this an attractive synthetic approach to 3-bromoflavones and flavones.
Answer 492:
Aromatic prenyltransferases for creating natural products deversification. Kazuyama, Tomohisa; Kumano, Takuto; Nishiyama,
Makoto. Research Center for Advanced Science and Technology, The University of Tokyo, Japan. Fain Kemikaru (2006), 35(2),
5-14. Publisher: Shi Emu Shi Shuppan, CODEN: FNKMAU ISSN: 0913-6150. Journal; General Review written in Japanese. CAN
Abstract
A review, on the discovery of arom. prenyltransferases; biochem. anal. of arom. prenyltransferases; and cryst. structure anal. of
ORF2. Arom. prenyltransferases.
Answer 493:
flavanone
Synthesis of raspberry ketone by bacteria expressing heterologous chalcone synthase gene. Beekwilder, Martinus Julius;
Sibbesen, Ole; Mikkelsen, Jurn Dalgaard; Van Der Meer, Ingrid Maria; Hall, Robert David; Qvist, Ingmar. (Danisco A/S, Den.). Brit.
UK Pat. Appl. (2006), 113 pp. CODEN: BAXXDU GB 2416770 A 20060208 Patent written in English. Application: GB

GB 2416770 A 20060208 GB 2004-16845 20040728
GB 2004-16845 20040728
Abstract
A host cell producing a chalcone synthase (CHS) and a 4-coumarate CoA: ligase (4CL) in which one or both are heterologous to the cell
is disclosed. A method of enabling benzalacetone synthase activity of a CHS protein comprises exposing the CHS to a microbial
cellular environment, preferably an E. coli cell. The benzalacetone may be reduced by benzalacetone reductase (BAR) in the bacterial
cell to make raspberry ketone. The host cell may be supplied with a raspberry ketone precursor, preferably benzalacetone or
p-coumaric acid. Sequences of raspberry CHS, tobacco 4CL and raspberry BAR genes and polypeptides are described as are vectors
comprising CHS and 4CL sequences, preferably in combination with a PAL (phenylalanine ammonia-lyase) gene or a cinnamic acid
4-hydroxylase (C4H) gene. The invention is based on the surprising discovery that chalcone synthase has benzalacetone synthase
(BAS) activity. Thus, transgenic E. coli expressing raspberry CHS cDNA and tobacco 4CL cDNA produced raspberry ketone from
coumaric acid. A no. of other CHS cDNA's, e.g., those of grape, Medicago, Arabidopsis, snapdragon, maize, and parsley, could be
substituted for the raspberry CHS cDNA.
Answer 494:
Constitutive expression of the Flavanone 3-hydroxylase gene related to pathotype-specific ascochyta blight resistance in
Cicer arietinum L. Cho, Seungho; Chen, Weidong; Muehlbauer, Fred J. School of Molecular Biosciences, Washington State
University, Pullman, WA, USA. Physiological and Molecular Plant Pathology (2006), Volume Date 2005, 67(2), 100-107.
Publisher: Elsevier B.V., CODEN: PMPPEZ ISSN: 0885-5765. Journal written in English. CAN 146:1261 AN 2006:104962
Abstract
Quant. resistance of chickpea (Cicer arietinum L.) to a necrotrophic fungal pathogen, Ascochyta rabiei (Pass) Labr., is conferred in a
pathotype-dependent manner. Unlike race-specific or qual. resistance, identification of genetic factors for blight resistance is difficult
because diverse pathogenic and environmental factors cause significant variation in resistance patterns. To identify genes assocd.
with blight resistance in chickpea, the authors conducted bulk segregation anal. of differential transcript patterns between blight
resistant and susceptible recombinant inbred lines (RILs) generated from a cross of PI 359075(1) (blight susceptible)×FLIP84-92C(2)
(blight resistant). Constitutive expression of a cDNA-AFLP fragment homologous to flavanone 3-hydroxylase (F3H) was lower in RILs
susceptible to pathotypes I and II of A. rabiei than in RILs resistant to both pathotypes. F3H was mapped to linkage group 5. Based
flavanone
on expression pattern of F3H between resistant and susceptible RIL bulks, F3H or its genomic vicinity on linkage group 5 was thought
to be related to blight resistance in chickpea. Further study is required to validate the genetic role of F3H and its genomic vicinity on
linkage group 5 in blight resistance in chickpea.
Answer 495:
Sirtuin related therapeutics and diagnostics for neurodegenerative diseases. Sinclair, David A.; Tsai, Li-Huei; Nguyen, Minh
Dang; Howitz, Konrad T.; Zipkin, Robert E.; Bitterman, Kevin J. (President and Fellows of Harvard College, USA). U.S. Pat. Appl.
Publ. (2006), 163 pp., Cont.-in-part of U.S. Ser. No. 884,022. CODEN: USXXCO US 2006025337 A1 20060202 Patent written
in English. Application: US 2005-74374 20050307. Priority: US 2003-483949 20030701; US 2003-532158 20031223; US
2004-884022 20040701; US 2004-884879 20040702. CAN 144:184697 AN 2006:104637 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))

US 20060025337 A1 20060202 US 2005-74374 20050307
US 20050096256 A1 20050505 US 2004-884022 20040701
US 20050136537 A1 20050623 US 2004-884879 20040702
AU 2006220554 A1 20060914 AU 2006-220554 20060307
CA 2599125 A1 20060914 CA 2006-2599125 20060307
WO 2006096780 A2 20060914 WO 2006-US8290 20060307
WO 2006096780 A3 20070118
EP 1863461 A2 20071212 EP 2006-737459 20060307
JP 2007326872 A 20071220 JP 2007-203287 20070803
US 2003-483949P P 20030701
US 2003-532158P P 20031223
US 2004-884022 A2 20040701
US 2004-884879 A2 20040702
US 2005-74374 A 20050307
WO 2006-US8290 W 20060307
JP 2006-518817 A3 20040701
flavanone
Abstract
Provided herein are methods and compns. for modulating the activity of sirtuin deacetylase protein family members; p53 activity;
apoptosis; lifespan and sensitivity to stress of cells and organisms. Exemplary methods comprise contacting a cell with an activating
compd., such as a flavone, stilbene, flavanone, isoflavone, catechin, chalcone, tannin or anthocyanidin; or an inhibitory compd., such
as a sphingolipid, e.g., sphingosine. Also disclosed herein are methods for treating, preventing or diagnosing a disease assocd. with
neuronal cell death, e.g., a neurodegenerative disease.
Answer 496:
Metabolic capacity enhancing compositions and methods for use in a mammal. Pedersen, Mark A. (USA). U.S. Pat. Appl.
Publ. (2006), 22 pp. CODEN: USXXCO US 2006024385 A1 20060202 Patent written in English. Application: US 2004-900038

US 20060024385 A1 20060202 US 2004-900038 20040727
US 2004-900038 20040727
Abstract
Metabolic energy capacity enhancing compns. and methods for reducing oxidative stress and improving vitality in a mammal are
disclosed. A compn. for increasing metabolic energy capacity may be in a palatable liq. formulation or a solid dosage form and
typically includes an anti-oxidant contg. phytonectar and an energy catalyst. An anti-oxidant may include a polyphenol, anthocyanin,
bioflavonoid, proanthocyanidin, and a xanthone. An energy catalyst may include a mineral, vitamin, co-vitamin, carbohydrate and a
lipid. In a presently preferred embodiment a compn. includes phytonectar exts. from grape, aloe vera, apple, morinda citrifolia,
scullcap, blueberry, prune, cranberry, elderberry, bilberry, and gentain and a mineral blend contg. calcium, magnesium, manganese,
zinc, chromium, selenium, iron, copper, molybdenum, vanadium, potassium, iodine, and cobalt. A method for increasing metabolic
energy capacity in a mammal may include consuming a chem. component having the ability to undergo oxidn., producing free radicals
and administering a compn. having an anti-oxidant contg. phytonectar and an energy catalyst.
Answer 497:
MITF gene expression promoting agents for the prevention of gray hair. Izuta, Tatsuo; Takeda, Shunsuke; Tajima, Masahiro.
(Shiseido Co., Ltd., Japan; Kirin Brewery Co., Ltd.). Jpn. Kokai Tokkyo Koho (2006), 21 pp. CODEN: JKXXAF JP 2006028143
A 20060202 Patent written in Japanese. Application: JP 2004-213569 20040721. Priority: . CAN 144:156165 AN 2006:99909

flavanone

JP 2006028143 A 20060202 JP 2004-213569 20040721
JP 2004-213569 20040721
Abstract
Disclosed are MITF gene expression promoting agents comprising isomerized hop exts. or ≥ 1 compds. selected from the group
consisting of chalcones, flavanones, and isohumulones. The MITF gene expression promoting agents stimulate the activities of
melanocytes and prevent gray hair. For example, a hair cream for inhibiting gray hair contained isohumulone 0.001,
stearyldimethylamineoxide 0.5, ethoxylated hydrogenated castor oil 1, 95 % ethanol 54.0, and ion-exchanged water balance to 100 %.
Answer 498:
Growth-promoting nitrogen nutrition affects flavonoid biosynthesis in young apple (Malus domestica Borkh.) leaves.
Strissel, T.; Halbwirth, H.; Hoyer, U.; Zistler, C.; Stich, K.; Treutter, D. Department fuer Pflanzenwissenschaften, Fachgebiet
Obstbau, Technische Universitaet Muenchen-Weihenstephan, Freising, Germany. Plant Biology (Stuttgart, Germany) (2005), 7(6),
677-685. Publisher: Georg Thieme Verlag, CODEN: PBIOFN ISSN: 1435-8603. Journal written in English. CAN 145:468069 AN
Abstract
Enhanced shoot growth and a decrease in flavonoid concn. in apple trees grown under high nitrogen (N) supply was obsd. in previous
studies, along with increasing scab susceptibility of cultivar Golden Delicious after high N nutrition. Several hypotheses have
suggested that there is a tradeoff between primary and secondary metab. because of competition for common substrates, but nothing
is known about regulation at the enzyme level. In this study, a set of expts. was performed to elucidate the effect of N nutrition on
the activities of key enzymes involved in flavonoid biosynthesis (phenylalanine ammonia-lyase [PAL], chalcone synthase/chalcone
isomerase [CHS/CHI], flavanone 3-hydroxylase [FHT], flavonol synthase [FLS], dihydroflavonol 4-reductase [DFR]) and the
accumulation of different groups of phenylpropanoids. The inhibition of flavonoid accumulation by high N nutrition could be confirmed,
but the influence of N supply on the flavonoid enzymes CHS/CHI, FHT, DFR, and FLS was not evident. However, PAL activity
seems to be down-regulated, thus forming a bottleneck resulting in a generally decreased flavonoid accumulation. Furthermore, the
response of the scab-resistant cultivar Rewena to high N nutrition was not as strong as that of the susceptible cultivar Golden
Delicious.
Answer 499:
Beech leaf colonization by the endophyte Apiognomonia errabunda dramatically depends on light exposure and climatic
conditions. Bahnweg, G.; Heller, W.; Stich, S.; Knappe, C.; Betz, G.; Heerdt, C.; Kehr, R. D.; Ernst, D.; Langebartels, C.; Nunn,
A. J.; Rothenburger, J.; Schubert, R.; Wallis, P.; Mueller-Starck, G.; Werner, H.; Matyssek, R.; Sandermann, H., Jr. GSF - National
Research Centre for Environment and Health, Institute of Biochemical Plant Pathology, Neuherberg, Germany. Plant Biology
(Stuttgart, Germany) (2005), 7(6), 659-669. Publisher: Georg Thieme Verlag, CODEN: PBIOFN ISSN: 1435-8603. Journal written
flavanone
Abstract
Ozone and light effects on endophytic colonization by Apiognomonia errabunda of adult beech trees (Fagus sylvatica) and their
putative mediation by internal defense compds. were studied at the Kranzberg Forest free-air ozone fumigation site. A. errabunda
colonization was quantified by "real-time PCR" (QPCR). A. errabunda-specific primers allowed detection without interference by DNA
from European beech and several species of common genera of plant pathogenic fungi, such as Mycosphaerella, Alternaria, Botrytis,
and Fusarium. Colonization levels of sun and shade leaves of European beech trees exposed either to ambient or twice ambient ozone
regimes were detd. Colonization was significantly higher in shade compared to sun leaves. Ozone exhibited a marginally inhibitory
effect on fungal colonization only in young leaves in 2002. The hot and dry summer of 2003 reduced fungal colonization dramatically,
being more pronounced than ozone treatment or sun exposure. Levels of sol. and cell wall-bound phenolic compds. were approx. twice
as high in sun than in shade leaves. Acylated flavonol 3-O-glycosides with putatively high UV-B shielding effect were very low in
shade canopy leaves. Ozone had only a minor influence on secondary metabolites in sun leaves. It slightly increased kaempferol
3-O-glucoside levels exclusively in shade leaves. The frequently prominent hydroxycinnamic acid deriv., chlorogenic acid, was tested
for its growth inhibiting activity against Apiognomonia and showed an IC50 of approx. 8 mM. Appearance of Apiognomonia-related
necroses strongly correlated with the occurrence of the stress metabolite, 3,3',4,4'-tetramethoxybiphenyl. Infection success of
Apiognomonia was highly dependent on light exposure, presumably affected by the endogenous levels of constitutive phenolic
compds. Ozone exerted only minor modulating effects, whereas climatic factors, such as pronounced heat periods and drought, were
dramatically overriding.
Answer 500:
Nucleotide diversity and linkage disequilibrium in cold-hardiness- and wood quality-related candidate genes in Douglas fir.
Krutovsky, Konstantin V.; Neale, David B. Institute of Forest Genetics, Pacific Southwest Research Station, U.S. Department of
Agriculture Forest Service, Davis, CA, USA. Genetics (2005), 171(4), 2029-2041. Publisher: Genetics Society of America,
CODEN: GENTAE ISSN: 0016-6731. Journal written in English. CAN 145:138538 AN 2006:88802 CAPLUS (Copyright (C)
Abstract
Nuclear sequence variation and linkage disequil. (LD) were studied in 15 cold-hardiness- and 3 wood quality-related candidate genes in
Douglas fir [Pseudotsuga menziesii (Mirb.) Franco]. This set of genes was selected on the basis of its function in other plants and
collocation with cold-hardiness-related quant. trait loci (QTL). The single-nucleotide polymorphism (SNP) discovery panel represented
24 different trees from six regions in Washington and Oregon plus parents of a segregating population used in the QTL study. The
frequency of SNPs was one SNP per 46 bp across coding and noncoding regions on av. Haplotype and nucleotide diversities were
also moderately high with Hd = 0.827 ± 0.043 and π = 0.00655 ± 0.00082 on av., resp. The nonsynonymous (replacement) nucleotide
substitutions were almost five times less frequent than synonymous ones and substitutions in noncoding regions. LD decayed
relatively slowly but steadily within genes. Haploblock anal. was used to define haplotype tag SNPs (htSNPs). These data will help to
select SNPs for assocn. mapping, which is already in progress.
Answer 501:
A new route for the synthesis of flavanones from 2-methoxybenzoic acids. Lee, Jae In; Jung, Mi Gung. Department of
Chemistry, College of Natural Science, Duksung Women's University, Seoul, S. Korea. Bulletin of the Korean Chemical Society
(2005), 26(12), 2044-2046. Publisher: Korean Chemical Society, CODEN: BKCSDE ISSN: 0253-2964. Journal written in English.
Abstract
flavanone
Treatment of 2-methoxybenzoates with 2 equiv MeLi in THF at -78° yielded 2'-methoxyacetophenones. Subsequent enolization with
LiN(CHMe2)2 and reaction with benzaldehydes afforded β-aryl-β-hydroxy-2'-methoxypropiophenones, which cyclized on dehydration of
the β-OH and successive conjugate addn. of the phenolic OH generated by cleavage of the 2'-MeO using HBr/AcOH. Thus, various
flavanones were synthesized in 38-62% yields.
Answer 502:
Production of flavonoids by recombinant microorganisms expressing plant metabolic pathway genes. Koffas, Mattheos;
Leonard, Effendi; Yan, Yajun; Chemler, Joseph. (The Research Foundation of State University of New York, USA). PCT Int. Appl.
(2006), 98 pp. CODEN: PIXXD2 WO 2006010117 A2 20060126 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB,
BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL,
IN, IS, JP, KE, KG, KM, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG,
PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW.
Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM,
20040710. CAN 144:169672 AN 2006:79417 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))

WO 2006010117 A2 20060126 WO 2005-US24525 20050711
WO 2006010117 A3 20060622
KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH,
PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN,
YU, ZA, ZM, ZW
CA 2573490 A1 20060126 CA 2005-2573490 20050711
US 20060019334 A1 20060126 US 2005-178912 20050711
US 7338791 B2 20080304
EP 1778850 A2 20070502 EP 2005-789029 20050711
JP 2008505657 T 20080228 JP 2007-521533 20050711
KR 2007035599 A 20070330 KR 2007-703269 20070209
US 2004-586903P P 20040710
WO 2005-US24525 W 20050711
Abstract
flavanone
Methods and compns. are provided for prodn. of flavonoids in microbial hosts. The compns. comprises a set of genes which encode
for enzymes involved in one or more steps in the biosynthetic pathway for the conversion of phenylpropanoids to various flavonoids.
The method comprises the steps of introducing the set of genes into a heterologous host cell, allowing growth of the cells in a suitable
medium such that the expression of the genes results in prodn. of enzymes. When specific substrate(s) is/are provided to the
transformed cell, the enzymes act on the substrate(s) to produce the desired flavonoids.
Answer 503:
Two-Phase Flavonoid Formation in Developing Strawberry (Fragaria x ananassa) Fruit. Halbwirth, Heidrun; Puhl, Iva; Haas,
Ursula; Jezik, Karoline; Treutter, Dieter; Stich, Karl. Institut fuer Verfahrenstechnik, Umwelttechnik und Technische
Biowissenschaften, Technische Universitaet Wien, Vienna, Austria. Journal of Agricultural and Food Chemistry (2006), 54(4),
Abstract
Flavonoids are important secondary metabolites in strawberry as they fulfill a wide variety of physiol. functions. In addn., they are
beneficial for human health. Previous studies have shown for selected enzymes from the flavonoid pathway that flavonoid
biosynthesis shows two peaks during fruit development. We provide optimized protocols for the detn. of the activities of the key
flavonoid enzymes: phenylalanine ammonia lyase, chalcone synthase/chalcone isomerase, flavanone 3-hydroxylase, dihydroflavonol
4-reductase, flavonol synthase, flavonoid 3-O-glucosyltransferase, and flavonoid 7-O-glucosyltransferase. Using these protocols we
were able to demonstrate two distinct activity peaks during fruit ripening at early and late developmental stages for all enzymes with
the exception of flavonol synthase. The first activity peak corresponds to the formation of flavanols, while the second peak is clearly
related to anthocyanin and flavonol accumulation. The results indicate that flavonoid 3-O-glucosyltransferase activity is not essential
for redirection from flavanol to anthocyanin formation in strawberry.
Answer 504:
Structure-activity relationships of the inhibitory effects of flavonoids on P-glycoprotein-mediated transport in KB-C2 cells.
Kitagawa, Shuji; Nabekura, Tomohiro; Takahashi, Tomoharu; Nakamura, Yutaka; Sakamoto, Hiromi; Tano, Hiromi; Hirai, Midori;
Tsukahara, Go. Niigata University of Pharmacy and Applied Life Sciences, 5-13-2 Kamishin'el-cho, Niigata, Japan. Biological &
Pharmaceutical Bulletin (2005), 28(12), 2274-2278. Publisher: Pharmaceutical Society of Japan, CODEN: BPBLEO ISSN:
Abstract
We studied the effects of flavonoids, naringenin (flavanone), baicalein (flavone), kaempferol, quercetin, myricetin, morin, and fisetin
(flavonols) as well as two glycosides of quercetin on P-glycoprotein (P-gp) function in multidrug-resistant P-gp overexpressing KB-C2
cells. Flavonoids such as kaempferol and quercetin increased the accumulation of rhodamine-123 dependent on their chem. structure.
Anal. by flow cytometry indicated that the increase in substrate accumulation was due to the inhibition of substrate efflux. Naringenin,
which lacks the 2,3-double bond in the C ring, had no effect, although it was more hydrophobic than myricetin, fisetin and morin.
Therefore, the planar structure of the flavonoids seemed to be important for their interaction with P-gp. The effects of other
flavonoids on the accumulation of daunorubicin were in the order of kaempferol >quercetin, baicalein >myricetin >fisetin, morin.
Quercetin-3-O-glucoside and rutin had no effect. The order of the effects corresponded with that of the partition coeffs. Difference in
the no. and position of hydroxyl groups in flavonoid mols. by themselves seemed to have little effect. These results suggested that
hydrophobicity as well as planar structure is important for the inhibitory effects of flavonoids on P-gp-mediated transport.
Answer 505:
flavanone
Scavenging capacities of some wines and wine phenolic extracts. Roussis, Ioannis G.; Lambropoulos, Ioannis; Soulti, Kalliopi.
Laboratory of Food Chemistry, Department of Chemistry, University of Ioannina, Ioannina, Greece. Food Technology and
Biotechnology (2005), 43(4), 351-358. Publisher: University of Zagreb, Faculty of Food Technology and Biotechnology, CODEN:
FTBRFD ISSN: 1330-9862. Journal written in English. CAN 144:273102 AN 2006:66062 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
The aim of this study was to assess the ability of different wines - a sweet red, a dry red, a sweet white, and a dry white - to
scavenge the stable 1,1'-diphenyl-2-picryl-hydrazyl radical (DPPH⋅) and to det. their phenolic compn. Both red wines contained, apart
from anthocyanins, also higher concn. of total phenolics, tartaric esters, and flavonols than the two white wines. All wines exhibited
scavenging activity analogous to their total phenolic content. However, their phenolics differed in antiradical potency, which was
visible in their EC50 values. The dry red wine, Xinomavro, had a lower EC50 value, indicating the higher antiradical potency of its
phenolics. The scavenging capacities of phenolic exts. from Xinomavro red wine on hydroxyl radicals, superoxide radicals, and singlet
oxygen were also assessed. Wine total ext. was fractionated by extn., and each of the three fractions was then subfractionated by
column chromatog. into two subfractions. Wine total ext., and its fractions and subfractions exhibited scavenging capacity on
hydroxyl radicals, superoxide radicals, and singlet oxygen, indicating the activity of many wine phenolics. The most active wine exts.
towards hydroxyl radicals were characterized by the high peaks of flavanols, anthocyanins and flavonols in their HPLC-DAD
chromatograms. The most active ext. towards superoxide radicals was rich in flavanols and anthocyanins. The characteristic
phenolics of the most active wine exts. towards singlet oxygen were flavanols, flavonols and phenolic acids. The ability of all red wine
phenolic exts. to scavenge singlet oxygen, along with hydroxyl and superoxide radicals, emphasizes its health functionality.
Answer 506:
Synthesis of (14C)-labeled 5-deoxyflavonoids and their application in the study of dihydroflavonol/leucoanthocyanidin

interconversion by dihydroflavonol 4-reductase. Halbwirth, Heidrun; Kahl, Stefan; Jaeger, Walter; Reznicek, Gottfried;
Forkmann, Gert; Stich, Karl. Institut fuer Verfahrenstechnik, Umwelttechnik und Technische Biowissenschaften, Technische
Universitaet Wien, Vienna, Austria. Plant Science (Amsterdam, Netherlands) (2006), 170(3), 587-595. Publisher: Elsevier B.V.,
CODEN: PLSCE4 ISSN: 0168-9452. Journal written in English. CAN 145:182793 AN 2006:58561 CAPLUS (Copyright (C)
Abstract
Biosynthesis is well elucidated for 5-hydroxyflavonoids (phloroglucinol type), but for 5-deoxyflavonoids (resorcinol type) the knowledge
is still limited. We provide detailed and optimized protocols for the synthesis of (14C)-labeled 6'-deoxychalcones, 5-deoxyflavanones,
5-deoxydihydroflavonols and 5-deoxyleucoanthocyanidins. With the exception of the formation of 6'-deoxychalcones, all steps were
performed enzymically using enzymes normally involved in the formation of 5-hydroxyflavonoids. The availability of (14C)-labeled
substrates will facilitate future work on the hitherto largely unknown biosynthesis of 5-deoxyflavonoids. In particular, the
5-deoxyleucoanthocyanidins, which are more stable than the corresponding 5-hydroxy compds., may provide excellent tools for
investigating enzymes, which use the unstable 5-hydroxyleucoanthocyanidins as natural substrates. As a first example, the
conversion of (14C)-labeled 5-deoxyleucoanthocyanidins to dihydroflavonols in the presence of NADP+ was shown. Studies with
defined genotypes of Matthiola incana possessing or lacking dihydroflavonol 4-reductase activity and genetically modified yeast
expressing the Matthiola enzyme confirmed that the reaction is catalyzed by the well-known dihydroflavonol 4-reductase, which
catalyzes the conversion of dihydroflavonols to leucoanthocyanidins (forward reaction). Thus, the reverse reaction of dihydroflavonol
4-reductase could be demonstrated for the first time. The forward reaction shows an optimum at pH 6.25, the reverse reaction at pH
7.75. The impact of the results on the regulation of flavonoid accumulation is discussed.
flavanone
Answer 507:
Expression analysis of anthocyanin biosynthetic genes in apple skin: Effect of UV-B and temperature. Ubi, Benjamin Ewa;
Honda, Chikako; Bessho, Hideo; Kondo, Satoru; Wada, Masato; Kobayashi, Shozo; Moriguchi, Takaya. Department of Plant, Cell
and Environment, National Institute of Fruit Tree Science, Tsukuba, Ibaraki, Japan. Plant Science (Amsterdam, Netherlands)
(2006), 170(3), 571-578. Publisher: Elsevier B.V., CODEN: PLSCE4 ISSN: 0168-9452. Journal written in English. CAN
Abstract
We investigated the expression of the five anthocyanin biosynthetic genes, chalcone synthase (CHS), flavanone 3-hydroxylase
(F3H), dihydroflavonol 4-reductase (DFR), anthocyanidin synthase (ANS), and UDP-glucose:flavonoid 3-O-glucosyltransferase
(UFGluT) during ripening in five early ripening apple cultivars ('Iwai', 'Sansa', 'Tsugaru', 'Homei-Tsugaru', and 'Akane'), as well as under
UV-B and temp. treatments. Anthocyanin biosynthesis increased progressively during ripening, with the onset of rapid accumulation
occurring at 107 days after full bloom (DAFB) in the four apple cultivars except Iwai'. Generally, increase in the expression levels of
all five biosynthetic genes in fruit skin coincided with increase of anthocyanin concn. When the fruit was bagged about 1 mo prior to
com. harvest to prevent anthocyanin biosynthesis, the expression of CHS, ANS and UFGluT was substantially depressed in fruit skin,
whereas that of all five genes including CHS, ANS and UFGluT was enhanced by UV-B and low temp. treatments with the
accumulation of anthocyanins. The accumulation level of the main anthocyanin pigment, cyanidin 3-galactoside, in the fruits under
UV-B and low temp. treatment, was less than that in the field-ripened fruits, while cyanidin 3-arabinoside was relatively the same level.
Our results showed that UV-B and low temp. were important factors for anthocyanin accumulation in apple fruit skin by inducing the
expression of the anthocyanin biosynthetic genes, esp. CHS, ANS and UFGluT genes.
Answer 508:
The mechanism of hair growth promotion by t-flavanone. Sasajima, Michiyo. Biological Science Laboratories, Tochigi,
Japan. Fragrance Journal (2005), 33(12), 36-43. Publisher: Fureguransu Janaru Sha, CODEN: FUJAD7 ISSN: 0288-9803.
Journal; General Review written in Japanese. CAN 144:418982 AN 2006:47790 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
A review with new data. We previously identified astilbin as a hair growth promoter contained in Hypericum perforatum. In order to
find a compd. that is safe and effective on hair growth, we made a lot of derivs. of taxifolin, the aglycon of astilbin and finally found
trans-3,4'-dimethyl-3-hydroxyflavanone, t-flavanone. T-Flavanone promoted hair growth in C3H mouse assay, in rat vibrissa organ
culture and in use test on male pattern baldness. To clarify the mechanism of the hair growth effect of t-flavanone, we focused on
TGF-β that is considered as a catagen inducer and a crucial key mol. of male pattern baldness. In the co-culture system of
keratinocytes and dermal papilla cells, t-flavanone decreased active-formed TGF-β2, however did not change the amt. of total TGF-β2.
When keratinocytes were incubated with t-flavanone, their ability to activate TGF-β2 decreased. These results suggest that
t-flavanone may affect on the TGF-β activating cascade and prevent the increase of active-formed TGF-β2. The redn. of TGF-β2
must extend the anagen period, so it can be an effective cure for many kind of balding disease. We tried the use test on women who
were suffering from baldness, and verified that t-flavanone has efficacy on women's baldness. T-Flavanone might be helpful for
people with various kind of baldness.
Answer 509:
flavanone
A new flavanoid from the flowers of Azadirachta indica. Siddiqui, Bina S.; Tariq Ali, Syed; Kashif Ali, Syed. H.E.J. Research
Institute of Chemistry, International Centre for Chemical Sciences, University of Karachi, Karachi, Pak. Natural Product
Research, Part A: Structure and Synthesis (2006), 20(3), 241-245. Publisher: Taylor & Francis Ltd., CODEN: NPRPC8 Journal
Abstract
Studies on the chem. constituents of the flowers of Azadirachta indica have led to the isolation of one new flavanone named as
azharone (5,7,4'-trihydroxy-3'-(3''-methyl-2'',3''-epoxybutyl)flavan-4-one) along with two known constituents azadirone, and
isoazadironolide. Their structures have been elucidated through spectral studies including 2D-NMR (COSY-45, NOESY, J-resolved,
HMQC, HMBC) expts.
Answer 510:
Manufacture of flavanones from Macaranga tanarius. Kumasawa, Shigenori; Nakayama, Tsutomu; Arakaki, Tsutomu; Fukumoto,
Shuichi. (Pokka Corp., Japan). Jpn. Kokai Tokkyo Koho (2006), 11 pp. CODEN: JKXXAF JP 2006008552 A 20060112 Patent
written in Japanese. Application: JP 2004-185655 20040623. Priority: . CAN 144:94232 AN 2006:34945 CAPLUS (Copyright

JP 2006008552 A 20060112 JP 2004-185655 20040623
JP 2004-185655 20040623
Abstract
5,7,3',4'-Tetrahydroxy-2'-(7''-hydroxy-3'',7''-dimethyloct-2''-enyl)flavanone (propolin A), 5,7,3',4'-tetrahydroxy-2'-geranylflavanone

(nymphaeol B), 5,7,3',4'-tetrahydroxy-5'-geranylflavanone (isonymphaeol B), and 5,7,3',4'-tetrahydroxy-6-geranylflavanone
(nymphaeol A) are manufd. by extn. of M. tanarius and purifn. of the obtained flavanones. Thus, pulverized M. tanarius leaves,
stems, trunks, and seeds were extd. with EtOH and purified by photodiode array-HPLC to give propolin A, nymphaeol A, B, and
isonymphaeol B at 48.7, 20.3, 62.9, and 5.2 μg/mg, resp.
Answer 511:
Regiospecific Flavonoid 7-O-Methylation with Streptomyces avermitilis O-Methyltransferase Expressed in Escherichia coli.
Kim, Bong-Gyu; Jung, Bo-Ra; Lee, Youngshim; Hur, Hor-Gil; Lim, Yoongho; Ahn, Joong-Hoon. Bio/Molecular Informatics Center,
Department of Molecular Biotechnology, Konkuk University, Seoul, S. Korea. Journal of Agricultural and Food Chemistry (2006),
54(3), 823-828. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN
flavanone
Abstract
O-Methylation, commonly found in synthesis of secondary metabolites of plants and micro-organisms, appears to transfer a Me group
to the hydroxyl group of the recipient which increases the hydrophobicity of the recipient. O-Methyltransferase (OMT), SaOMT-2, was
isolated and characterized from Streptomyces avermitilis MA-4680. Its amino acid sequence showed 68% similarity with antibiotic
C-1027 OMT and 53% similarity with the carminomycin 4-OMT. SaOMT-2 was expressed in E. coli as a His-tag fusion protein and
showed that the Me was transferred onto the 7- hydroxyl group of the isoflavones, daidzein and genistein, and the flavones,
kaempferol and quercetin, as well as the flavanone naringenin. NMR and liq. chromatog.-mass spectrometry were used to confirm the
location of the Me group on the recipient compd. of naringenin, which was biotransformed into sakuranetin by E. coli transformant
expressing SaOMT-2 (E. coli Sa-2). Therefore, E. coli Sa-2 would be used for the synthesis of the antifungal flavonoid, sakuranetin,
through biotransformation.
Answer 512:
Isolation and structure identification of a new flavanone from Dryopteris sublaeta. Feng, Wei-Sheng; Cao, Xin-Wei; Kuang,
Hai-Xue; Zheng, Xiao-Ke. Sch. Pharm., Henan Coll. Traditional Chinese Med., Zhengzhou, Peop. Rep. China. Zhongguo Tianran
Yaowu (2005), 3(6), 336-339. Publisher: Zhongguo Tianran Yaowu Bianjibu, CODEN: ZTYHA7 ISSN: 1672-3651. Journal written in
Abstract
Water extn., silica gel, Diaion HP-20, Toyopearl HW-40, Sephadex LH-20 column hromatog. were used. for studying the chem.
constituents of Dryopteris sublaeta Ching et Hsu. The structures of isolated compds. were elucidated by various physiochem. and
spectral data. Six compds. were obtained and identified as 2(S)-5,7,3'-trihydroxy-6,8-dclimethyl-4'-methoxy-flavanone
(3'-hydroxy-matteucinol) (1), matteucinol-7-O-β-D-glucopyranoside (2), spinasterol (3), spinasterol-3-O-β-D-glucopyranoside (4),
sitosterol (5) and daucosterol (6). Compd. 1 is new; compds. 2, 3 and 4 were isolated from Dryopteris for the first time.
Answer 513:
Synthesis of isoflavones containing naturally occurring substitution pattern by oxidative rearrangement of respective
flavanones using thallium(III) p-tosylate. Singh, Om V.; Muthukrishnan, M.; Sunderavadivelu, M. Phytochemistry Division,
Tropical Botanic Garden and Research Institute, Thiruvanathapuram, India. Indian Journal of Chemistry, Section B: Organic
Chemistry Including Medicinal Chemistry (2005), 44B(12), 2575-2581. Publisher: National Institute of Science Communication and
Information Resources, CODEN: IJSBDB ISSN: 0376-4699. Journal written in English. CAN 146:142391 AN 2006:1051
Abstract
Claisen condensation of substituted 2'-hydroxyacetophenones I (R = R2 = H, R1 = MeO; R = H, R1 = R2 = MeO; R = R1 = MeO, R2 =

H) with arom. aldehydes II (R3, R4, R5, R6 = H, MeO; R3 = R6 = H, R4R5 = OCH2O) affords resp. substituted 2'-hydroxychalcones
III which on base catalyzed cyclization in pyridine:methanol:water (1:1:1) give resp. flavanones IV. The oxidative rearrangement of
flavanones IV with thallium(III) p-tosylate furnishes resp. isoflavones V in overall 62-72% yields starting from I. The present
methodol. has been successfully applied for the synthesis of naturally occurring isoflavones such as di-O-methyldaidzein, cabruvin,
pseudobabtigenin methylether, 5,7-dimethoxyisoflavone, 5,7,4'-trimethoxyisoflavone, derrustone, 7,8,3',4'-tetramethoxyisoflavone,
purpuranin-A and 7,8,3',4',5'-pentamethoxyisoflavone (VI) and thus the first synthesis of VI is reported.
flavanone
R R4
R1 OH R3 R5
Me H
R6
R2 O I O II
R4 R4
R3 R5 R3 R5
R R
R1 OH R1 O
R6 R6
R2 O III R2 O IV
R1 O
R3
R4
R2 O
R5
R6 V
Answer 514:
Antiherpetic activities of flavonoids against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) in vitro. Lyu, Su-Yun;
Rhim, Jee-Young; Park, Won-Bong. Immune Modulation Research Group, The School of Pharmacy, University of Nottingham,
Nottingham, UK. Archives of Pharmacal Research (2005), 28(11), 1293-1301. Publisher: Pharmaceutical Society of Korea,
CODEN: APHRDQ ISSN: 0253-6269. Journal written in English. CAN 144:403824 AN 2005:1355075 CAPLUS (Copyright (C)
Abstract
Flavonoids, a group of low mol. wt. phenylbenzopyrones, have various pharmacol. properties including antioxidant, anticancer,
bactericidal, and anti-inflammatory. We carried out anti-herpetic assays on 18 flavonoids in five classes and a virus-induced
cytopathic effect (CPE) inhibitory assay, plaque redn. assay, and yield redn. assay were performed. When flavonoids were applied at
various concns. to Vero cells infected by HSV-1 and 2, most of the flavonoids showed inhibitory effects on virus-induced CPE.
flavanone
Among the flavonoids, EC, ECG (flavanols), genistein (isoflavone), naringenin (flavanone), and quercetin (flavonol) showed a high
level of CPE inhibitory activity. The antiviral activity of flavonoids were also examd. by a plaque redn. assay. EC, ECG, galangin,
and kaempferol showed a strong antiviral activity, and catechin, EGC, EGCG, naringenin, chrysin, baicalin, fisetin, myricetin,
quercetin, and genistein showed moderate inhibitory effects against HSV-1. In these expts., flavanols and flavonols appeared to be
more active than flavones. Furthermore, treatment of Vero cells with ECG and galangin (which previously showed strong antiviral
activities) before virus adsorption led to a slight enhancement of inhibition as detd. by a yield redn. assay, indicating that an
intracellular effect may also be involved.
Answer 515:
Studies on dihydroflavonol glycosides from rhizome of Smilax glabra. Yuan, Jiuzhi; Dou, Deqiang; Chen, Yingjie; Li, Wei;
Kazuo, Koike; Tamotsu, Nikaido; Yao, Xinsheng. Department of Natural Products Chemistry, Shenyang Pharmaceutical University,
Shenyang, Peop. Rep. China. Zhongguo Zhongyao Zazhi (2004), 29(9), 867-869, 870. Publisher: Zhongguo Zhongyao Zazhishe,
CODEN: ZZZAE3 ISSN: 1001-5302. Journal written in Chinese. CAN 145:24149 AN 2005:1346876 CAPLUS (Copyright (C)
Abstract
The chem. constituents from the rhizomes of Smilax glabra were studied. The compds. were isolated by column chromatog. with silica
gel, Diaion HP-20 and ODS as packing materials, and HPLC. Their structures were detd. on the basis of their spectral evidence. Five
dihydroflavonol glycosides were identified as: astilbin (1), neoastilbin (2), isoastilbin (3), neoisoastilbin (4), and
(2R,3R)-taxifolin-3'-O-β-D-glucopyranoside (5). Compds. 2, 4, 5 were isolated from the plant for the first time.
Answer 516:
Preparation of flavanone derivatives as inducers of heme oxygenase or induction promoters of heme oxygenase. Miyaji,
Hiroyuki; Eiraku, Tomohiko; Ishiguro, Hanae. (Kyorin Pharmaceutical Co., Ltd., Japan). Jpn. Kokai Tokkyo Koho (2005), 42 pp.
CODEN: JKXXAF JP 2005350362 A 20051222 Patent written in Japanese. Application: JP 2004-170090 20040608. Priority: .

JP 2005350362 A 20051222 JP 2004-170090 20040608
JP 2004-170090 20040608
Abstract
Flavanone derivs. (I) [X = each (un)substituted Ph or heteroaryl; Y = (un)substituted Ph, pyridyl; R1 -R3 = H, halo, C1-12 alkoxy, HO,
each (un)substituted C2-6 cyclic or noncyclic amino, Ph, PhO, benzyloxy,, or heteroaryl; X is in E or Z form or in its mixt.] are prepd.
These compds. are useful for the treatment of acute lung injury (ALI) and acute respiratory distress syndrome (ARDS), chronic
obstructive pulmonary disease (COPD), and asthma and for protection of transplanted organs. Thus, 224 mg flavanone, 174 mg
flavanone
4-trifluoromethylbenzaldehyde, and 0.03 mL piperidine were mixed and stirred at 150° for 2 h to give, after silica gel chromatog.,
3-(4-trimethoxybenzylidene)flavanone. 3-(3,4,5-Trimethoxybenzylidene)flavanone at 3 μM increased heme oxygenase activity by
10.13 fold in human umbilical vein endothelial cells (HUVECs) based on the increased prodn. of bilirubin.
R1 O Y
X
R2
R3 O I
Answer 517:
Investigation of two distinct flavone synthases for plant-specific flavone biosynthesis in Saccharomyces cerevisiae.
Leonard, Effendi; Yan, Yajun; Lim, Kok Hong; Koffas, Mattheos A. G. Department of Chemical and Biological Engineering,
University at Buffalo, The State University of New York, Buffalo, NY, USA. Applied and Environmental Microbiology (2005),
71(12), 8241-8248. Publisher: American Society for Microbiology, CODEN: AEMIDF ISSN: 0099-2240. Journal written in English.
Abstract
Flavones are plant secondary metabolites that have wide pharmaceutical and nutraceutical applications. We previously constructed a
recombinant flavanone pathway by expressing in Saccharomyces cerevisiae a four-step recombinant pathway that consists of
cinnamate-4 hydroxylase, 4-coumaroyl:CoA ligase, chalcone synthase, and chalcone isomerase. In the present work, the
biosynthesis of flavones by two distinct flavone synthases was evaluated by introducing a sol. flavone synthase I (FSI) and a
membrane-bound flavone synthase II (FSII) into the flavanone-producing recombinant yeast strain. The resulting recombinant strains
were able to convert various phenylpropanoid acid precursors into the flavone mols. chrysin, apigenin, and luteolin, and the
intermediate flavanones pinocembrin, naringenin, and eriodictyol accumulated in the medium. Improvement of flavone biosynthesis
was achieved by overexpressing the yeast P 450 reductase CPR1 in the FSII-expressing recombinant strain and by using acetate
rather than glucose or raffinose as the carbon source. Overall, the FSI-expressing recombinant strain produced 50% more apigenin
and six times less naringenin than the FSII-expressing recombinant strain when p-coumaric acid was used as a precursor
phenylpropanoid acid. Further expts. indicated that unlike luteolin, the 5,7,4'-trihydroxyflavone apigenin inhibits flavanone biosynthesis
in vivo in a nonlinear, dose-dependent manner.
Answer 518:
Synthesis and application of mono-2A-azido-2A-deoxyperphenylcarbamoylated β-cyclodextrin and

mono-2A-azido-2A-deoxyperacetylated β-cyclodextrin as chiral stationary phases for high-performance liquid
chromatography. Poon, Yin-Fun; Muderawan, I. Wayan; Ng, Siu-Choon. Innovation Centre, Division of Chemical and
Biomolecular Engineering, College of Engineering, Nanyang Technological University, Singapore, Singapore. Journal of
Abstract
flavanone
Two novel chiral stationary phases (CSPs) were prepd. based upon the regioselective immobilizations of β-cyclodextrin (β-CD) at its C2
position to the silica support. The mono-2A-azido-2A-deoxyperphenylcarbamoylated β-cyclodextrin and
mono-2A-azido-2A-deoxyperacetylated β-cyclodextrin were synthesized by selective tosylation and azidolysis followed by
perfunctionalization. The derivatized cyclodextrins were then immobilized onto the aminised silica gel via the Staudinger reaction to
provide new chiral stationary phases. Their application to high-performance liq. chromatog. (HPLC) enantiosepn. of racemic compds.
was demonstrated using β-adrenergic blockers, flavanone compds., benzodiazepinones, antihistamines and weakly protolytic compds.,
of which good sepns. were achieved for some racemic compds., for instance, bendroflumethiazide (R s 6.26), oxazepam (R s 5.99),
temazepam (R s 2.85) and althiazide (R s 1.13) when compared with the corresponding CSPs where the β-CD mol. was regioselectively
immobilized at the C6 position. The enantio-discriminatory properties of these CSPs were found to be affected by the orientation of
the CD cavity under reversed-phase conditions, and also by the derivitizing groups of the CD. The HPLC results inferred that the
mono-6A-azido-6A-deoxyperphenylcarbamoylated CD CSP (CD bonded at C6 position to silica) exhibited slightly better chiral
recognition ability than mono-2A-azido-2A-deoxyperphenylcarbamoylated CD CSP under the normal-phase and reversed-phase modes
on the sepn. of 31 different racemic compds. and drugs. On the contrary, higher chiral recognition abilities were obsd. on the
mono-2A-azido-2A-deoxyperacetylated CD CSP compared to mono-6A-azido-6A-deoxyperacetylated CD CSP.
Answer 519:
Differential antibacterial activity of genistein arising from global inhibition of DNA, RNA and protein synthesis in some
bacterial strains. Ulanowska, Katarzyna; Tkaczyk, Aleksandra; Konopa, Grazyna; Wegrzyn, Grzegorz. Department of Molecular
Biology, University of Gdansk, Gdansk, Pol. Archives of Microbiology (2006), 184(5), 271-278. Publisher: Springer, CODEN:
AMICCW ISSN: 0302-8933. Journal written in English. CAN 144:250223 AN 2005:1317507 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Antibacterial activities of various flavonoids were reported previously, but mechanism(s) of their action on bacterial cells remain(s)
largely unknown. Here, the authors investigated effects of genistein, an isoflavone, and representatives of other flavonoids: daidzein
(another isoflavone), apigenin (a flavone), naringenin (a flavanone), and kaempferol (a flavonol), on commonly used lab. strains of
model bacterial species: Escherichia coli, Vibrio harveyi, and Bacillus subtilis. The authors found that E. coli was resistant to all tested
flavonoids at concns. up to 0.1 mM, while high sensitivity of V. harveyi to most of them (except daidzein, which exhibited significantly
less pronounced effect) was obsd. Effects of the flavonoids on B. subtilis were relatively intermediate to the 2 extremes, i.e., E. coli
and V. harveyi. Action of genistein on bacterial cells was investigated in more detail to indicate changed cell morphol. (formation of
filamentous cells) of V. harveyi and drastic inhibition of global synthesis of DNA and RNA as shortly as 15 min after addn. of this
isoflavone to a bacterial culture to a final concn. of 0.1 mM. Protein synthesis inhibition was also apparent, but delayed. Both cell
morphol. and synthesis of nucleic acids and proteins were unaffected in E. coli cultures under analogous conditions. Studies on cell
survival suggest that genistein is a bacteriostatic agent rather than a bactericidal compd.
Answer 520:
Characterization of Flavonoids and Pectins from Bergamot (Citrus bergamia Risso) Peel, a Major Byproduct of Essential Oil
Extraction. Mandalari, Giuseppina; Bennett, Richard N.; Bisignano, Giuseppe; Saija, Antonella; Dugo, Giacomo; Lo Curto, Rosario
B.; Faulds, Craig B.; Waldron, Keith W. Department of Pharmaco-Biology and Department of Organic and Biological Chemistry,
University of Messina, Messina, Italy. Journal of Agricultural and Food Chemistry (2006), 54(1), 197-203. Publisher: American
Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 144:190814 AN 2005:1302713
Abstract
flavanone
Bergamot peel is an underutilized byproduct of the essential oil and juice-processing industry. As with other Citrus peels, it still
contains exploitable components, such as pectins and flavonoids. Com. glycoside hydrolases, specifically a combination of
pectolytic and cellulolytic enzymes, solubilized a high percentage of the material (81.94%). The flavonoid profile of the peel consisted
of characteristic Citrus species flavanone rutinosides and neohesperosides derived from naringenin, eriodictyol, and hesperetin. In
addn., a no. of minor flavanone and flavone glycosides, not found in orange and lemon peels, were identified. The majority of
flavonoids were extd. in the 2 70% vol./vol. EtOH extns. Processing this material clearly has economic potential leading to low
environmental impact.
Answer 521:
Application of support vector machine (SVM) for prediction toxic activity of different data sets. Zhao, C. Y.; Zhang, H. X.;
Zhang, X. Y.; Liu, M. C.; Hu, Z. D.; Fan, B. T. Department of Chemistry, Lanzhou University, Lanzhou, Peop. Rep. China.
Toxicology (2006), 217(2-3), 105-119. Publisher: Elsevier Ltd., CODEN: TXCYAC ISSN: 0300-483X. Journal written in English.
Abstract
As a new method, support vector machine (SVM) were applied for prediction of toxicity of different data sets compared with other two
common methods, multiple linear regression (MLR) and RBFNN. Quant. structure-activity relationships (QSAR) models based on
calcd. mol. descriptors have been clearly established. Among them, SVM model gave the highest q 2 and correlation coeff. R. It
indicates that the SVM performed better generalization ability than the MLR and RBFNN methods, esp. in the test set and the whole
data set. This eventually leads to better generalization than neural networks, which implement the empirical risk minimization principle
and may not converge to global solns. We would expect SVM method as a powerful tool for the prediction of mol. properties.
Answer 522:
Variation in the content of bioactive flavonoids in different brands of orange and grapefruit juices. Vanamala, Jairam;
Reddivari, Lavanya; Yoo, Kil Sun; Pike, Leonard M.; Patil, Bhimanagouda S. Department of Horticultural Sciences, Vegetable and
Fruit Improvement Center, College Station, TX, USA. Journal of Food Composition and Analysis (2005), Volume Date 2006,
19(2-3), 157-166. Publisher: Elsevier, CODEN: JFCAEE ISSN: 0889-1575. Journal written in English. CAN 145:270471 AN
Abstract
Citrus flavonoids have been shown to possess biol. activities such as anti-inflammatory properties, cholesterol lowering and immune
system modulation. In this study, 12 made-from-conc. (MFC) and 14 not-from-conc. (NFC) orange juices, and five NFC grapefruit
juices available in the US market were analyzed for their flavonoid content by reverse phase HPLC. Individual and total flavonoid
content was detd. for all of the brands. The correlation between flavonoid content (mg) and price (US dollar) per unit vol. of orange and
grapefruit juices were also evaluated. Significant differences ( P ≤ 0.05 ) among the brands and within the brand were obsd. for all of
the prominent flavanone glucosides. Within the brand, juice types contg. added antioxidant vitamins C and E were not superior in
flavonoid content compared to orange juice types devoid of added antioxidant vitamins. Total flavonoid content of MFC orange juices
(53 mg/100 mL; n = 12 ) was significantly ( P ≤ 0.05 ) higher than NFC orange juices (36.5 mg/100 mL; n = 14 ). Hesperidin was found
to be the major flavonoid followed by narirutin and didymin in orange juice. Naringin, narirutin, and poncirin were the major flavonoids
in all brands of grapefruit juices. The concn. of didymin was considerably higher in NFC orange juices compared to MFC orange
juices. Interestingly, no correlation was obsd. between price and the total flavonoid content of MFC orange juices and NFC grapefruit
juices. However, a significant neg. correlation ( r = - 0.49 ; P = 0.001 ) was obsd. for NFC orange juices. This study provides valuable
information on flavonoid compn. of orange and grapefruit juices commonly available in the US market.
flavanone
Answer 523:
Cytotoxic chalcones and flavonoids from the leaves of Muntingia calabura. Chen, Jih-Jung; Lee, Hsinn-Hsing; Duh,
Chang-Yih; Chen, Ih-Sheng. Graduate Institute of Pharmaceutical Technology, Tajen Institute of Technology, Pingtung, Taiwan.
Planta Medica (2005), 71(10), 970-973. Publisher: Georg Thieme Verlag, CODEN: PLMEAA ISSN: 0032-0943. Journal written in
Abstract
Two new dihydrochalcones, 2',4'-dihydroxy-3'-methoxydihydrochalcone, (-)-3'-methoxy-2',4',β-trihydroxydihydrochalcone, a new

flavanone, (2S)-(-)-5'-hydroxy-7,3',4'-trimethoxyflavanone, and a new flavonol deriv., muntingone, along with sixteen known compds.,
were isolated from the leaves of Muntingia calabura. The structures of these new compds. were detd. using spectral analyses
including extensive 2D NMR data. Among the isolates, (2S)-5'-hydroxy-7,3',4'-trimethoxyflavanone, 4'-hydroxy-7-methoxyflavanone,
2',4'-dihydroxychalcone, and 2',4'-dihydroxy-3'-methoxychalcone exhibited cytotoxicity (IC50 values < 4 μg/mL) against P-388 and/or
HT-29 cell lines in vitro.
Answer 524:
Compositions comprising extracts from Zanthoxylum and Anogeissus and citrus juice for the treatment of HIV-associated
infections and complications. Ashiagbor, Kwame Titus; Ashiagbor, Stephen; Wutoh, Anthony K.; Kallia, Yaw Foster; Wutoh, Rita
Delores; Wutoh, Jeffrey K.; Aidoo, Elnora. (Ghana). U.S. Pat. Appl. Publ. (2005), 16 pp. CODEN: USXXCO US 2005266105
A1 20051201 Patent written in English. Application: US 2005-62769 20050222. Priority: US 2004-545508 20040219. CAN

US 20050266105 A1 20051201 US 2005-62769 20050222
WO 2006118553 A1 20061109 WO 2005-US5492 20050222
RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA,
ZM, ZW
RW: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LT, LU, MC, NL, PL, PT, RO,
SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG, BW, GH, GM,
KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM
US 2004-545508P P 20040219
Abstract
flavanone
The present invention pertains to compns. for the treatment of HIV-related opportunistic infections and complications. More
specifically, the present invention is directed to a compn. comprising Zanthoxylum gillettii and Anogeissus leiocarpus, in combination
with citrus juice, or biomass exts. isolated therefrom, and methods of using and manufg. the same. For example, an i.p. compns.
contg. exts. from Zanthoxylum and Anogeissus and citrus juice was found to be able to effectively treat HIV assocd. infections.
Answer 525:
Chemical constituents from Schisandra plena. Li, R.-T.; Zhao, A.-H.; Sheng, Y.-H.; Na, Z.; Sun, H.-D. State Key Laboratory
of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming,
Peop. Rep. China. Journal of Asian Natural Products Research (2005), 7(6), 847-852. Publisher: Taylor & Francis Ltd., CODEN:
JANRFI ISSN: 1028-6020. Journal written in English. CAN 145:414060 AN 2005:1256605 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
The chem. constituents of the leaves and stems of Schisandra plena are described for the first time. This investigation has resulted in
the isolation of a new sesquiterpenoid, plenoxide (I). In addn., eleven known compds., including sesquiterpenoids, coumarins,
flavanones, triterpenoids and steroids have also been isolated. The structure and stereochem. of 1 has been detd. on the basis of
spectroscopic anal. Detailed anal. of 2D NMR data led to the conclusion that the chem. shifts of earlier compds. similar to bullatantriol
need revision.
OH
Me
Me
H
Me Me
O I
Answer 526:
Molecular mechanism of the naringin low uptake by intestinal Caco-2 cell. Tourniaire, Franck; Hassan, Meryl; Andre, Marc;
Ghiringhelli, Odette; Alquier, Christian; Amiot, Marie-Josephe. Faculte de Medecine, UMR U-476 INSERM/U-1260 INRA, Marseille,
Fr. Molecular Nutrition & Food Research (2005), 49(10), 957-962. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN:
MNFRCV ISSN: 1613-4125. Journal written in English. CAN 145:7045 AN 2005:1252115 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Naringin, the main flavanone of grapefruit, was reported to display numerous biol. effects: antioxidant, hypocholesteremic,
anti-atherogenic and favoring drug absorption. Naringin absorption mechanisms were studied in Caco-2 cells (TC7 clone). We
investigated the possible involvement of several membrane transporters implicated in polyphenolic compds. intestinal transport
(sodium-dependent glucose transporter 1, monocarboxylate transporter, multidrug-assocd. resistance proteins 1 and 2, and
P-glycoprotein). Naringin was poorly absorbed by Caco-2 cells, according to its low value of apparent permeability coeff. (Papp = 8.1
flavanone
± 0.9 × 10-8 cm/s). In the presence of verapamil, a specific inhibitor of P-glycoprotein, cellular uptake was increased by almost
threefold after 5 min, and Papp was doubled after 30 min. Our results indicated the involvement of P-glycoprotein, an ATP-driven
efflux pump, capable of transporting naringin from the Caco-2 cell to the apical side. This phenomenon could explain, at least in part,
the low absorption of this flavanone at the upper intestinal level.
Answer 527:
Protection against nuclear DNA damage offered by flavonoids in cells exposed to hydrogen peroxide: The role of iron
chelation. Melidou, Maria; Riganakos, Kyriakos; Galaris, Dimitrios. Laboratory of Biological Chemistry, School of Medicine,
University of Ioannina, Ioannina, Greece. Free Radical Biology & Medicine (2005), 39(12), 1591-1600. Publisher: Elsevier,
CODEN: FRBMEH ISSN: 0891-5849. Journal written in English. CAN 144:45018 AN 2005:1233685 CAPLUS (Copyright (C)
Abstract
The ability of a no. of flavonoids belonging to the flavone, flavonol, flavanone, and flavan-3-ol subclasses to protect cellular DNA
from H2O2-induced single-strand breaks and the underlying mol. mechanisms were investigated in this work. Formation of
single-strand breaks on nuclear DNA, after exposure of Jurkat cells to continuously generated H2O2 in the presence or absence of the
flavonoid compds., was evaluated by the comet assay (single-cell gel electrophoresis). The results indicate the following structural
requirements of flavonoids for effective DNA protection: (a) the ortho-dihydroxy structure in either ring A or ring B, (b) the hydroxyl
moiety on position 3 in combination with the oxo group at position 4, and (c) the presence of a C2, C3 double bond in ring C. In
contrast to free flavonoids, the ability of complexes of [Fe2+]/[flavonoid] to protect nuclear DNA was decreased as the ratio
increased, and the complex was completely inactive when the ratio reached a certain value. Moreover, it was obsd. that several of the
flavonoids tested were able to remove iron from calcein loaded into cells and that this property was in excellent correlation with their
ability to protect DNA (Spearman's correlation coeff., ρ = 0.9, p = 0.005). The antioxidant (electron donating) capacities of the same
flavonoids were also evaluated by a conventional method, but no relation with their DNA-protective ability could be established even
when their membrane-penetrating abilities were taken into account (p = 0.64). In conclusion, the results presented in this work strongly
support the notion that intracellular binding of iron is responsible for the protection offered by flavonoids against H2O2-induced DNA
damage.
Answer 528:
Inhibition of collagenase by naturally-occurring flavonoids. Sin, Bo Young; Kim, Hyun Pyo. College of Pharmacy,
Kangwon National University, Chunchon, S. Korea. Archives of Pharmacal Research (2005), 28(10), 1152-1155. Publisher:
Pharmaceutical Society of Korea, CODEN: APHRDQ ISSN: 0253-6269. Journal written in English. CAN 143:452796 AN
Abstract
We examd. the inhibitory activities of various flavonoids, including the flavanones, flavones/isoflavones and flavonols, on
collagenase from Clostridium histolyticum to establish their therapeutic potential against skin inflammation and photoaging. In general,
the flavonols were stronger inhibitors than the flavones/isoflavones, and this indicated the importance of the C-3 hydroxyl substitution.
Quercetin was the most active flavonoid among those tested, and it showed an IC50 of 286 μM. These novel results suggest that
certain flavonoids, particularly the flavonols, may prevent collagen breakdown by inhibiting collagenase in inflamed skin as well as
photoaged skin.
Answer 529:
flavanone
Metabolic engineering of plant cells for biotransformation of hesperedin into neohesperidin, a substrate for production of
the low-calorie sweetener and flavor enhancer NHDC. Frydman, Ahuva; Weisshaus, Oori; Huhman, David V.; Sumner, Lloyd
W.; Bar-Peled, Maor; Lewinsohn, Efraim; Fluhr, Robert; Gressel, Jonathan; Eyal, Yoram. Institute of Horticulture, Volcani Center,
Bet-Dagan, Israel. Journal of Agricultural and Food Chemistry (2005), 53(25), 9708-9712. Publisher: American Chemical Society,
CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 144:107017 AN 2005:1211342 CAPLUS (Copyright (C)
Abstract
Neohesperidin dihydrochalcone (NHDC) is a seminatural, safe, low-calorie sweetener, bitterness blocker, and flavor enhancer with
unique properties and applications for the food, beverage, pharmaceutical, and animal feed industries. Current prodn. is limited by the
availability of the substrate neohesperidin, a flavonoid that accumulates to significant levels only in the inedible bitter citrus species.
We propose a process to convert hesperidin, a tasteless flavonoid extd. from orange peels that are abundant byproducts of the vast
orange juice industry, into neohesperidin using metabolic engineering and biotransformation via three steps: (i) extn. of hesperidin from
orange peels, (ii) hydrolysis of sugar moieties, and (iii) biotransformation of hesperidin hydrolysis products into neohesperidin. We
overcame the current technol. bottleneck in biotransformation of hesperidin hydrolysis products into neohesperidin using metabolically
engineered plant cell cultures expressing a recombinant flavanone-7-O-glucoside-2-O-rhamnosyltransferase. A small-scale prodn. expt.
established the feasibility of the proposed process.
Answer 530:
Additional flavonoids from Lonchocarpus yucatanensis and L. xuul. Borges-Argaez, Rocio; Diaz, Maria Esther Poot;
Waterman, Peter G.; Pena-Rodriguez, Luis M. Unidad de Biotecnologia, Centro de Investigacion Cientifica de Yucatan, Merida,
Mex. Journal of the Brazilian Chemical Society (2005), 16(5), 1078-1081. Publisher: Sociedade Brasileira de Quimica, CODEN:
JOCSET ISSN: 0103-5053. Journal written in English. CAN 144:408136 AN 2005:1206260 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Two new natural flavanones, 5-hydroxy-6,7-(2'',2''-dimethylchromene)flavanone and

5-methoxy-3-hydroxy-6,7-(2'',2''-dimethylchromene)flavanone, were isolated from the root exts. of L. yucatanensis and L. xuul, resp.
Addnl., 4 known metabolites, the glycosidic flavonoids quercetin-3-rhamnoglucoside and kaempferol-3-rhamnoglucoside, together with
4-hydroxy-N-methyl-proline, and p-coumaric acid Me ester, were isolated for the first time from the leaves of L. xuul. The various
metabolites were identified on the basis of their spectroscopic data and by comparison with those reported in the literature.
Answer 531:
Capillary electrochromatography on methacrylate based monolithic columns: Evaluation of column performance and
separation of polyphenols. Messina, A.; Desiderio, C.; De Rossi, A.; Bachechi, F.; Sinibaldi, M. Dipartimento di Chimica,
Universita di Roma "La Sapienza", Rome, Italy. Chromatographia (2005), 62(7/8), 409-416. Publisher: Vieweg Verlag/GWV
Fachverlage GmbH, CODEN: CHRGB7 ISSN: 0009-5893. Journal written in English. CAN 144:169758 AN 2005:1204471
flavanone
Abstract
Fused-silica capillary columns (100 μm I.D.) englobing a porous monolithic stationary phase were prepd. by in situ copolymn. of
2-ethylhexyl methacrylate, ethylene glycol dimethacrylate and 2-acrylamido-2-methylpropanesulfonic acid (AMPS) in the presence of a
porogenic mixt. contg. 1-propanol, 1,4 butanediol and water. The influence of the monomers ratio and the porogen solvent compn. as
well as the content of AMPS in the polymn. mixt. on column total porosity and efficiency was investigated to attain min. HETP values
for the reversed-phase capillary electrochromatog. sepn. of bioflavonoids. For the most promising column, the van Deemter plots, in
both μ-HPLC and CEC, were also evaluated. In CEC the reduced plate height was found almost const. (1.6-2.0) within the range of
linear mobile phase velocity between 0.2-2.0 mm/s. The chem. and mech. stabilities of the monolithic column over a wide range of
buffer pH (2-10) and time were satisfactory. Furthermore, the effects of mobile phase parameters, such as buffer concn. and org.
modifier content, on the electroosmotic flow were studied systematically. CEC sepns. of std. mixts. of polyphenols, including
flavonols, flavanones and flavanones-7-O-glycosides, were accomplished in less than 8 min. The CEC sepn. of the major flavanone
glycoside constituents in the ext. from a freshly squeezed grapefruit juice was also reported.
Answer 532:
Manganese(III) acetate-mediated oxidation of flavanones. A facile synthesis of flavones. Singh, Om V.; Muthukrishnan, M.;
Raj, Gopan. Phytochemistry Division, Tropical Botanic Garden and Research Institute, Thiruvananthapuram, India. Synthetic
Communications (2005), 35(20), 2723-2728. Publisher: Taylor & Francis, Inc., CODEN: SYNCAV ISSN: 0039-7911. Journal
Abstract
Oxidn. of flavanones with manganese(III) acetate by heating in acetic acid in presence of perchloric acid afforded exclusively
flavones by dehydrogenation in almost quant. yields.
Answer 533:
Flavonoid components and flower color change in transgenic tobacco plants by suppression of chalcone isomerase gene.
Nishihara, Masahiro; Nakatsuka, Takashi; Yamamura, Saburo. Iwate Biotechnology Research Center, Narita, Kitakami, Iwate,
Japan. FEBS Letters (2005), 579(27), 6074-6078. Publisher: Elsevier B.V., CODEN: FEBLAL ISSN: 0014-5793. Journal written
Abstract
A cDNA encoding chalcone isomerase (CHI) was isolated from the petals of Nicotiana tabacum and the effect of its suppression on
flavonoid biosynthesis was analyzed in transgenic tobacco plants. CHI-suppression by RNA interference (RNAi) showed reduced
pigmentation and change of flavonoid components in flower petals. The plants also accumulated high levels of chalcone in pollen,
showing a yellow coloration. Our results first demonstrated that suppression of CHI by genetic transformation is possible in higher
plants. This suggests that CHI plays a major part in the cyclization reaction from chalcone to flavanone, and that spontaneous
reactions are few, if any, in tobacco plants.
Answer 534:
flavanone
5,2'-Dihydroxy-7-methoxyflavanone. Krishnaiah, M.; Ravi Kumar, R.; Kumar, N. Jagadeesh; Gunasekar, D.; Jayaprakasam, B.
Department of Physics, Sri Venkateswara University, Tirupati (AP), India. Acta Crystallographica, Section E: Structure Reports
Online (2005), E61(11), o3565-o3567. Publisher: Blackwell Publishing Ltd., CODEN: ACSEBH ISSN: 1600-5368.
http://journals.iucr.org/e/issues/2005/11/00/ci6641/index.html Journal; Online Computer File written in English. CAN 144:321849
Abstract
Crystals of the title compd. are monoclinic, space group P21/c, with a 10.1961(10), b 7.5600(8), c 18.243(2) .ANG., β 105.59(2)°; Z =
4, dc = 1.404, dm = 1.40; R = 0.064, Rw(F2) = 0.201 for 2346 reflections. The γ-pyranone ring adopts an envelope conformation. The
crystal packing is stabilized by O-H⋅⋅⋅O and C-H⋅⋅⋅O H bonding.
Answer 535:
Studies of the pharmacodynamics of flavanone extract tinctures for treating vulva leukoplakia. Li, Shou-Xiang; Zhang,
Xue-Jun; Meng, Hong; Han, Ru; Wu, Hong-Ying; Zheng, Yun-Xia; Ma, Jin-Feng; Zhu, Hua. Shandong Institute of Prevention and
Control of Professional Health and Occupational Diseases, Ji'nan, Peop. Rep. China. Yaoxue Fuwu Yu Yanjiu (2005), 5(3),
296-299. Publisher: Yaoxue Fuwu Yu Yanjiu Zazhishe, CODEN: YFYYAH ISSN: 1671-2838. Journal written in Chinese. CAN
Abstract
The pharmacodynamics of flavanone exts. for treatment of vulva leukoplakia and its mechanism was studied. The flavanone ext.
was made up into 0.2% tincture (contained 25% ethanol). The pharmacodynamics and the preliminary clin. effects of flavanone ext.
tincture were explored by inhibition of virus in vitro; anti-inflammation, relieving itch, and alleviating pain in mice; anti-granuloma expt.
in rats; and treatment of 116 patients with vulva leukoplakia. The drug had obvious effects to relieve pain and itch, accelerated the
healing of the damaged tissues, anti-chronic granuloma and the acute inflammatory seeps and anti-virus. The prepn. of flavanone is
substantiated that it is quick to take effect, easy to operate, less of toxic and side effect after treatment of patients with vulva
leukoplakia.
Answer 536:
Reactions of hydroxy-substituted flavanones with nitric oxide. Zhang, Hong-Rui; Wu, Long-Min. State Key Laboratory of
Applied Organic Chemistry, Lanzhou University, Lanzhou, Peop. Rep. China. Youji Huaxue (2005), 25(10), 1248-1253.
Publisher: Youji Huaxue Bianjibu, CODEN: YCHHDX ISSN: 0253-2786. Journal written in Chinese. CAN 145:292740 AN
Abstract
Hydroxy-substituted flavanones reacted with NO to afford mono- and multi-nitro derivs. The mononitration occurred at the ortho- or
para-position with respect to the hydroxy group. Dinitrations occurred at two ortho-positions or both ortho- and para-positions to the
hydroxy group with longer reaction time than that of mononitration. The reaction of polyhydroxy-substituted flavanones with NO gave
polynitrated derivs.
Answer 537:
flavanone
The wp mutation of Glycine max carries a gene-fragment-rich transposon of the CACTA superfamily. Zabala, Gracia; Vodkin,
Lila O. Department of Crop Sciences, University of Illinois, Urbana, IL, USA. Plant Cell (2005), 17(10), 2619-2632. Publisher:
American Society of Plant Biologists, CODEN: PLCEEW ISSN: 1040-4651. Journal written in English. CAN 144:287221 AN
Abstract
We used soybean (Glycine max) cDNA microarrays to identify candidate genes for a stable mutation at the Wp locus in soybean,
which changed a purple-flowered phenotype to pink, and found that flavanone 3-hydroxylase cDNAs were overexpressed in purple
flower buds relative to the pink. Restriction fragment length polymorphism anal. and RNA gel blots of purple and pink flower isolines,
as well as the presence of a 5.7-kb transposon insertion in the wp mutant allele, have unequivocally shown that flavanone
3-hydroxylase gene 1 is the Wp locus. Moreover, the 5.7-kb insertion in wp represents a novel transposable element (termed
Tgm-Express1) with inverted repeats closely related to those of other Tgms (transposable-like elements, G. max) but distinct in several
characteristics, including the lack of subterminal inverted repeats. More significantly, Tgm-Express1 contains four truncated cellular
genes from the soybean genome, resembling the Pack-MULEs (Mutator-like transposable elements) found in maize (Zea mays), rice
(Oryza sativa), and Arabidopsis thaliana and the Helitrons of maize. The presence of the Tgm-Express1 element causing the wp
mutation, as well as a second Tgm-Express2 element elsewhere in the soybean genome, extends the ability to acquire and transport
host DNA segments to the CACTA family of elements, which includes both Tgm and the prototypical maize Spm/En.
Answer 538:
A new flavanone, reflexin, from Cuscuta reflexa and its selective sensing of nitric oxide. Tripathi, V. J.; Yadav, S. B.;
Upadhyay, A. K. Department of Chemistry, Banaras Hindu University, Varanasi, India. Applied Biochemistry and Biotechnology
(2005), 127(1), 63-67. Publisher: Humana Press Inc., CODEN: ABIBDL ISSN: 0273-2289. Journal written in English. CAN
Abstract
A new compd., reflexin, 5-hydroxy-7-methoxy-6-(2,3-epoxy-3-methylbutyl)-flavanone, is isolated from the stems of Cuscuta reflexa
along with three other known compds. This new compd. has good potential for application esp. in the photoactivity of reflexin. It was
found to be sensitive to glutathione, forming a fluorescent product that is utilized for sensing nitric oxide (NO). The lowest detection
limit of NO anal. was found to be 0.05 μM.
Answer 539:
Colour genes (R and Rc) for grain and coleoptile upregulate flavonoid biosynthesis genes in wheat. Himi, Eiko; Nisar,
Ahmed; Noda, Kazuhiko. Research Institute for Bioresources, Okayama University, Kurashiki, Okayama, Japan. Genome
(2005), 48(4), 747-754. Publisher: National Research Council of Canada, CODEN: GENOE3 ISSN: 0831-2796. Journal written in
Abstract
flavanone
Pigmentation of wheat grain and coleoptile is controlled by the R gene on chromosomes of the homoeologous group 3 and the Rc gene
on chromosomes of the homoeologous group 7, resp. Each of these genes is inherited monogenically. The pigment of grain has been
suggested to be a deriv. of catechin-tannin and that of coleoptile to be anthocyanin. These polyphenol compds. are known to be
synthesized through the flavonoid biosynthesis pathway. We isolated 4 partial nucleotide sequences of the early flavonoid
biosynthesis genes (CHS, CHI, F3H, and DFR) in wheat. The expression of these genes was examd. in the developing grain of
red-grained and white-grained wheat lines. CHS, CHI, F3H, and DFR were highly upregulated in the grain coat tissue of the red-grained
lines, whereas there was no significant expression in the white-grained lines. These results indicate that the R gene is involved in the
activation of the early flavonoid biosynthesis genes. As for coleoptile pigmentation, all 4 genes were expressed in the red coleoptile;
however, DFR was not activated in the white coleoptile. The Rc gene appears to be involved in DFR expression. The possibility that
wheat R and Rc genes might be transcription factors is discussed.
Answer 540:
Skin-lightening cosmetics containing acidic xylooligosaccharides, natural products, and polyhydric alcohols. Tanaka,
Hiroshi; Azumi, Naoya. (Narisu Cosmetic Co., Ltd., Japan; Oji Paper Co., Ltd.). Jpn. Kokai Tokkyo Koho (2005), 16 pp.
CODEN: JKXXAF JP 2005289880 A 20051020 Patent written in Japanese. Application: JP 2004-107255 20040331. Priority: .

JP 2005289880 A 20051020 JP 2004-107255 20040331
JP 2004-107255 20040331
Abstract
Skin-lightening cosmetics comprise (1) acidic xylooligosaccharides (av. polymn. degree ≤ 5), (2) keratinocyte prodn. signal transduction
inhibitors, such as reduced NAD, and (3) ≥ 1 substances from the group consisting of melanin prodn. inhibitors, antioxidants,
inflammation inhibitors, high-mol. wt. compds., and polyhydric alcs. For example, a cream was formulated contg. beeswax 2, stearyl
alc. 5, stearic acid 8, squalane 10, glyceryl monostearate 3, polyoxyethylene cetyl ether 1, Helianthus annus seed exts. 5, acidic
xylooligosaccharides 5, KOH 0.3, preservatives q.s., reduced NAD 0.1, and distd. water balance to 100 %.
Answer 541:
Synthesis and Characterization of Cellulose Carbamates Having α-Amino Acid Moieties. Shen, Xiande; Sugie, Norihiko; Duan,
Qian; Kitajyo, Yoshikazu; Satoh, Toshifumi; Kakuchi, Toyoji. Division of Biotechnology and Macromolecular Chemistry, Graduate
School of Engineering, Hokkaido University, Sapporo, Japan. Polymer Bulletin (Heidelberg, Germany) (2005), 55(5), 317-322.
Publisher: Springer, CODEN: POBUDR ISSN: 0170-0839. Journal written in English. CAN 144:53224 AN 2005:1127171
Abstract
flavanone
The reaction of cellulose with N-carbonyl α-amino acid ester leading to corresponding cellulose carbamate was carried out in
N,N-dimethylacetamide at 100 °C. For N-carbonyl L-leucine Et ester (I), the degree of the carbamate substituent (DS) in cellulose
carbamate was 2.5 for I/[glucose units in cellulose] = 3.0 and reached ca. 3.0 for I/[glucose units in cellulose] = 4.0. One cellulose
carbamate was highly sol. in not only aprotic polar solvents but also other org. solvents such as Et ether and Me alc. The chiral
discrimination ability of this product was higher than those of the cellulose carbamates having L-phenylalanine and L-aspartic acid
moieties.
Answer 542:
Efficient production of (2S)-flavanones by Escherichia coli containing an artificial biosynthetic gene cluster. Miyahisa,
Ikuo; Kaneko, Masafumi; Funa, Nobutaka; Kawasaki, Hisashi; Kojima, Hiroyuki; Ohnishi, Yasuo; Horinouchi, Sueharu. Department
of Biotechnology, Graduate School of Agriculture and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo, Japan. Applied
Microbiology and Biotechnology (2005), 68(4), 498-504. Publisher: Springer, CODEN: AMBIDG ISSN: 0175-7598. Journal written in
Abstract
For the fermentative prodn. of plant-specific flavanones (naringenin, pinocembrin) by Escherichia coli, a plasmid was constructed
which carried an artificial biosynthetic gene cluster, including PAL encoding a phenylalanine ammonia-lyase from a yeast, ScCCL
encoding a cinnamate/coumarate:CoA ligase from the actinomycete Streptomyces coelicolor A3(2), CHS encoding a chalcone
synthase from a licorice plant and CHI encoding a chalcone isomerase from the Pueraria plant. The recombinant E. coli cells produced
(2S)-naringenin from tyrosine and (2S)-pinocembrin from phenylalanine. When the two subunit genes of acetyl-CoA carboxylase from
Corynebacterium glutamicum were expressed under the control of the T7 promoter and the ribosome-binding sequence in the
recombinant E. coli cells, the flavanone yields were greatly increased, probably because enhanced expression of acetyl-CoA
carboxylase increased a pool of malonyl-CoA that was available for flavanone synthesis. Under cultural conditions where E. coli at a
cell d. of 50 g/l was incubated in the presence of 3 mM tyrosine or phenylalanine, the yields of naringenin and pinocembrin reached
about 60 mg/l. The fermentative prodn. of flavanones in E. coli is the first step in the construction of a library of flavonoid compds.
and un-natural flavonoids in bacteria.
Answer 543:
ESR study of the flavonoid effect on the metal ion breakdown of lipid peroxidation system. Djilas, S. M.;
Canadanovic-Brunet, J. M.; Cetkovic, G. S.; Tumbas, V. T. Organic Chemistry Department, Faculty of Technology, University of
Novi Sad, Novi Sad, Oxidation Communications (2005), 28(3), 547-554. Publisher: SciBulCom Ltd., CODEN: OXCODW ISSN:
Abstract
The formation of alkoxyl radical during metal ion breakdown of hydroperoxide-enriched Me linoleate of sunflower oil has been
established by a combination of spin trapping and ESR spectroscopy. The influence of different concns. (10-100 μmol dm-3) of
myricetin, quercetin, morin, kaempferol, rutin, fisetin, diosmetin, apigenin, luteolin, and naringenin, resp., on the formation and
transformation of alkoxyl radical was evaluated. Results demonstrated that the antioxidative activity depends on the structure and
concn. of applied flavonoids and it decreases in the following order: flavonol > flavone > flavanone. The formation of relatively stable
free radicals for these flavonoid derivs. was studied. Under exptl. conditions employed, the generation of stable free radicals has
been evidenced for myricetin, quercetin, rutin, and luteolin and their hyperfine coupling consts. were detd. The 2,3-double bond in
conjugation with 4-oxo function and the addnl. presence of both 3- and 5-hydroxyl groups as well as o-dihydroxyl groups in the B-ring
are very important for antioxidant activity of the investigated flavonoids and aroxyl radical stabilization.
flavanone
Answer 544:
Direct synthesis of highly ordered large-pore functionalized mesoporous SBA-15 silica with methylaminopropyl groups and
its catalytic reactivity in flavanone synthesis. Wang, Xueguang; Tseng, Yao-Hung; Chan, Jerry C. C.; Cheng, Soofin.
Department of Chemistry, National Taiwan University, Taipei, Taiwan. Microporous and Mesoporous Materials (2005), 85(3),
241-251. Publisher: Elsevier B.V., CODEN: MIMMFJ ISSN: 1387-1811. Journal written in English. CAN 145:271516 AN
Abstract
Functionalized SBA-15 mesoporous silica materials with a p6mm symmetry have been synthesized through a simple co-condensation
approach of tetraethylorthosilicate (TEOS) and (3-(methylamino)propyl)trimethoxysilane (MAPTMS) using amphiphilic block co-polymers
under acidic conditions. The influence of the amt. of MAPTMS in the initial synthesis mixt. on the mesostructural properties of the
resultant materials was studied by varying the molar ratios of MAPTMS to TEOS. X-ray powder diffraction (XRD) and N2 sorption
results indicated that the ordering of the mesoporous structure was dependent on the amt. of MAPTMS added in the initial mixt.
Solid-state NMR, thermogravimetric anal. (TGA) and elemental anal. showed that the incorporation of the org. groups in the silica
framework increased with the MAPTMS concn. in the synthesis mixt. TEOS pre-hydrolysis prior to the addn. of MAPTES had great
influence on the crystallog. ordering, pore size, surface area and pore vol. of the resultant functionalized mesoporous silica materials.
Moreover, the addn. of inorg. salt in the initial mixt. could greatly enhance the mesostructure ordering and stability of the mesoporous
materials. With the aid of NaCl salt, the modified SBA-15 materials with the content of methylaminopropyl groups up to 2.37 mmol/g
still possessed well-ordered mesoporous structure and had high specific area and pore vol. The modified SBA-15 showed high catalytic
activities and selectivities toward flavanones synthesis through the Claisen-Schmidt condensation of substituted acetophenones and
benzaldehyde derivs. and subsequent intramol. Michael addn. in the absence of solvent.
Answer 545:
Plantphysiological investigations of non-parasitic leaf spots of barley Hordeum vulgare L. Zahn, Martina. Institut fuer
Meteorologie und Klimaforschung, Facultaet fuer Biologie, Universitaet Freiburg, Germany. Wissenschaftliche Berichte -
Forschungszentrum Karlsruhe (2005), (FZKA 7128), i-xiii, 1-149. CODEN: WBFKF5 ISSN: 0947-8620. Report written in German.
Abstract
Non-parasitic leaf spots (NPLS) of barley cultivars Hordeum vulgare L. are a leaf damage which was obsd. only in the last fifteen
years. It is unknown what the main reasons for these damages may be. The hypothesis that oxidative burst is the origin for these
spots relies on the observation that they mostly occur when the radiation is high and the plants are in a defined stage of development.
Several trials in climate chambers were made to investigate the development of the NPLS. For this reason the plants underwent
different conditions, like enhanced sun radiation and high ozone concns. It could be demonstrated that the photon flux is important for
the spot formation. In comparison to the resistant cultivar IPZ 24727 a significant higher level of superoxide anion radicals was found
in the sensitive NPLS cultivar cv. Ricarda. Leaves of barley plants developed much more NPLS than the control plants when they
were tested under high radiation conditions during the expts. This observations were also made in freeland trials. There was no
correlation found between higher ozone concns. and the development of NPLS, but between stage of development of the barley and
decrease of the spots. Even when the ears began to arise the spots developed very quickly. In view of this observation the
antioxidative systems were analyzed. The concns. of ascorbate and glutathione decreased with growing age like the enzyme activity
of Cu/Zn-SOD in the chloroplasts. A decrease of superoxide anion radicals was obsd. when the plants are grew older. In this stage of
development it may be that the older leaves switch over to put their supply at seed's disposal. The hypothesis is that cultivars which
are sensitive regarding to NPLS getting senescent earlier than the resistant cultivars. In this stage of development the plants are more
flavanone
sensitive against oxidative burst and it may be that they react to high radiation with a marked manifestation of spots.
The results of this investigations strengthen the assumption that the main reason for NPLS is an oxidative burst which is
generated by environmental conditions. Radiation is an important factor but not the only one. In the NPLS sensitive
cultivars ROS were not reduced in the way of the resistant cultivars because of an lower enzyme activity of Cu/Zn-SOD.
Answer 546:
Isolation and identification of flavonoids, including flavone rotamers, from the herbal drug Crataegi folium cum flore
(hawthorn). Rayyan, S.; Fossen, T.; Nateland, H. Solheim; Andersen, Oe. M. Department of Chemistry, University of Bergen,
Bergen, Norway. Phytochemical Analysis (2005), 16(5), 334-341. Publisher: John Wiley & Sons Ltd., CODEN: PHANEL ISSN:
Abstract
Twelve flavonoids, including seven flavones, four flavonols and one flavanone, were isolated from methanolic ext. of the herbal drug
'Crataegi folium cum flore' (hawthorn leaves and flowers) by a combination of CC (over Amberlite XAD-7 and Sephadex LH-20) and
preparative HPLC. Their structures, including that of the novel flavonol 8-methoxykaempferol 3-O-(6''-malonyl-β-glucopyranoside),
were elucidated by homo- and heteronuclear NMR and electrospray/MS. The 1H- and 13C-NMR of all compds., including rotameric
pairs of five flavone C-glycosides, were assigned. The presence and relative proportion of each rotamer was shown by various NMR
expts., including two-dimensional nuclear Overhauser and exchange spectroscopy, to depend on solvent, linkage position and structure
of the C-glycosyl substituent.
Answer 547:
Flavanones, their manufacture from propolis derived from Macaranga tanarius, and antioxidants containing them.
Kumasawa, Shigenori; Nakayama, Tsutomu; Arakaki, Tsutomu; Fukumoto, Shuichi. (Pokka Corp., Japan). Jpn. Kokai Tokkyo Koho
(2005), 16 pp. CODEN: JKXXAF JP 2005272374 A 20051006 Patent written in Japanese. Application: JP 2004-89552

JP 2005272374 A 20051006 JP 2004-89552 20040325
JP 2004-89552 20040325
Abstract
Flavanones I, II, and III are manufd. by purifn. from propolis derived from plants including M. tanarius. Also claimed are antioxidants,
useful as food additives, health foods, drugs, cosmetics, quasi-drugs, etc., contg. I, II, or III. Thus, propolis collected in Okinawa was
extd. with EtOH under ultrasonication and fractionated by silica gel column and HPLC to give I, II, and III. Radical scavenging activity
of I was comparable to that of eriodictyol.
flavanone
OH
OH
HO O
HO
Me Me Me OH O I
OH
HO O OH
Me Me Me
OH O II
OH
HO O Me
Me Me
OH O III
Answer 548:
QSAR study of natural, synthetic and environmental endocrine disrupting compounds for binding to the androgen receptor.
Zhao, C. Y.; Zhang, R. S.; Zhang, H. X.; Xue, C. X.; Liu, H. X.; Liu, M. C.; Hu, Z. D.; Fan, B. T. Department of Chemistry, Lanzhou
University, Lanzhou, Peop. Rep. China. SAR and QSAR in Environmental Research (2005), 16(4), 349-367. Publisher: Taylor &
Francis Ltd., CODEN: SQERED ISSN: 1062-936X. Journal written in English. CAN 143:320310 AN 2005:1069421 CAPLUS
Abstract
flavanone
A large data set of 146 natural, synthetic and environmental chems. belonging to a broad range of structural classes have been tested
for their relative binding affinity (expressed as log (RBA)) to the androgen receptor (AR). These chems. commonly termed endocrine
disrupting compds. (EDCs) present a variety of adverse effects in humans and animals. As assays for binding affinity remains a
time-consuming task, it is important to develop predictive methods. In this work, quant. structure-activity relationships (QSARs) were
detd. using three methods, multiple linear regression (MLR), radical basis function neural network (RBFNN) and support vector machine
(SVM). Five descriptors, accounting for hydrogen-bonding interaction, distribution of at. charges and mol. branching degree, were
selected from a heuristic method to build predictive QSAR models. Comparison of the results obtained from three models showed that
the SVM method exhibited the best overall performances, with a RMS error of 0.54 log (RBA) units for the training set, 0.59 for the test
set, and 0.55 for the whole set. Moreover, six linear QSAR models were constructed for some specific families based on their chem.
structures. These predictive toxicol. models, should be useful to rapidly identify potential androgenic endocrine disrupting compds.
Answer 549:
Surface composition of myrmecophilic plants: cuticular wax and glandular trichomes on leaves of Macaranga tanarius.
Guhling, Ortwin; Kinzler, Christian; Dreyer, Michael; Bringmann, Gerhard; Jetter, Reinhard. Julius-von-Sachs Institut fuer
Biowissenschaften, Universitaet Wuerzburg, Wuerzburg, Germany. Journal of Chemical Ecology (2005), 31(10), 2323-2341.
Publisher: Springer Science+Business Media, Inc., CODEN: JCECD8 ISSN: 0098-0331. Journal written in English. CAN
Abstract
Primary plant surfaces, covered with cuticles consisting of cutin and waxes, are important substrates for interaction with insects. The
compn. of leaf surfaces of the myrmecophilic plant Macaranga tanarius was studied. The prenylated flavanone nymphaeol-C was
identified in surface exts. and was localized exclusively in glandular trichomes on the abaxial leaf side. The epidermal pavement cells
surrounding these trichomes were covered with a smooth film of epicuticular wax from which few small wax crystals protruded. The
epicuticular wax amounted to approx. 8 μg cm-2, corresponding to 85% of the wax load on the adaxial as well as the abaxial leaf sides.
The epicuticular wax mixts. from both leaf surfaces contained more than 70% primary alcs., 14% fatty acids, 2% aldehydes, and
traces of alkyl acetates, with chain lengths ranging from C20 to C38. In contrast, the intracuticular wax layer was largely dominated
by triterpenoid alcs. α-amyrin, β-amyrin, and lupeol. Consequently, these characteristic compds. are not available for direct contact
with insects on the plant surface.
Answer 550:
Preparative isolation and separation of a novel and two known flavonoids from Patrinia villosa Juss by high-speed
counter-current chromatography. Peng, Jinyong; Yang, Genjin; Fan, Guorong; Wu, Yutian. Shanghai Key Laboratory for
Pharmaceutical Metabolite Research, School of Pharmacy, Second Military Medical University, Shanghai, Peop. Rep. China.
Journal of Chromatography, A (2005), 1092(2), 235-240. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal
Abstract
Preparative high-speed counter-current chromatog. (HSCCC) was successfully used for isolation and sepn. 3 of flavonoids including
bolusanthol B, a novel compd. named 5,7,2',6'-tetrahydroxy-6,8-di(γ,γ-dimethylallyl) flavanone and tetrapterol I from Patrinia villosa
Juss using 2-phase solvent system composed of n-hexane-Et acetate-methanol-water at the vol. ratio of 10:11:11:8 (vol./vol.). A total
of 25.4 mg bolusanthol B, 52.5 mg 5,7,2',6'-tetrahydroxy-6,8-di(γ,γ-dimethylallyl) flavanone and 50.2 mg tetrapterol I were obtained
from 250 mg crude ext. with purities of 96.8%, 99.2% and 99.3%, resp. detd. by HPLC in one single operation and less than 5 h. The
structure identification was performed by UV, IR, MS, 1H NMR, 13C NMR and 2D NMR. Among them, bolusanthol B and tetrapterol I
flavanone
were obtained from the plant of Patrinia genius for the first time, and 5,7,2',6'-tetrahydroxy-6,8-di(γ,γ-dimethylallyl) flavanone was a
novel prenylated flavonoid and discovered from nature for the first time.
Answer 551:
Novel formation of spirocyclic oxazolines in the reaction of some (E)-3-(4-methoxybenzylidene)flavanones with

NaN3/concentrate H2SO4-HOAc. Mallik, Asok K.; Chattopadhyay, Falguni; Patra, Amarendra. Department of Chemistry,
Jadavpur University, Kolkata, India. Journal of Chemical Research (2005), (8), 543-545. Publisher: Science Reviews, CODEN:
JCROA4 Journal written in English. CAN 144:390608 AN 2005:1027583 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
On treatment with NaN3/conc. H2SO4-HOAc, some (E)-3-(4-methoxybenzylidene)flavanones yield a new type of flavonoid-derived
spirocyclic oxazolines in moderate yield. A plausible mechanism for formation of these products is suggested.
Answer 552:
Biosynthesis of natural flavanones in Saccharomyces cerevisiae. Yan, Yajun; Kohli, Abhijeet; Koffas, Mattheos A. G.
Department of Chemical and Biological Engineering, University at Buffalo, State University of New York, Buffalo, NY, USA.
Applied and Environmental Microbiology (2005), 71(9), 5610-5613. Publisher: American Society for Microbiology, CODEN: AEMIDF
SciFinder (R))
Abstract
A four-step flavanone biosynthetic pathway was constructed and introduced into Saccharomyces cerevisiae. The recombinant yeast
strain was fed with phenylpropanoid acids and produced the flavanones naringenin and pinocembrin 62 and 22 times more efficiently
compared to previously reported recombinant prokaryotic strains. Microbial biosynthesis of the flavanone eriodictyol was also
achieved.
Answer 553:
Epoxide formation on the aromatic B ring of flavanone by biphenyl dioxygenase of Pseudomonas pseudoalcaligenes KF707.
Han, Jaehong; Kim, Song-Young; Jung, Jihyun; Lim, Yoongho; Ahn, Joong-Hoon; Kim, Su-Il; Hur, Hor-Gil. Metalloenzyme Research
Group, BET Research Institute and Department of Biotechnology, Chung-Ang University, Anseong, S. Korea. Applied and
Environmental Microbiology (2005), 71(9), 5354-5361. Publisher: American Society for Microbiology, CODEN: AEMIDF ISSN:
Abstract
Prokaryotic dioxygenase is known to catalyze arom. compds. into their corresponding cis-dihydrodiols without the formation of an
epoxide intermediate. Biphenyl dioxygenase from Pseudomonas pseudoalcaligenes KF707 showed novel monooxygenase activity by
converting 2(R)- and 2(S)-flavanone to their corresponding epoxides
flavanone
(2-(7-oxabicyclo[4.1.0]hepta-2,4-dien-2-yl)-2,3-dihydro-4H-chromen-4-one), whereby the epoxide bond was formed between C2' and C3'
on the B ring of the flavanone. The enzyme also converted 6-hydroxyflavanone and 7-hydroxyflavanone, which do not contain a
hydroxyl group on the B-ring, to their corresponding epoxides. In a previous report, however, the authors found that the same enzyme
showed dioxygenase activity toward flavone, resulting in the prodn. of flavone cis-2',3'-dihydrodiol. Extensive structural identification
of the metabolites of flavanone by using HPLC, liq. chromatog./mass spectrometry, and NMR confirmed the presence of an epoxide
functional group on the metabolites. Epoxide formation as the initial activation step of arom. compds. by oxygenases has been
reported to occur only by eukaryotic monooxygenases. To the best of the authors' knowledge, biphenyl dioxygenase from P.
pseudoalcaligenes KF707 is the first prokaryotic enzyme detected that can produce an epoxide deriv. on the arom. ring structure of
flavanone.
Answer 554:
Flavonols, Flavones, Flavanones, and Human Health: Epidemiological Evidence. Graf, Brigitte A.; Milbury, Paul E.;
Blumberg, Jeffrey B. Antioxidants Research Laboratory, Jean Mayer USDA Human Nutrition Research Center on Aging, Tufts
University, Boston, MA, USA. Journal of Medicinal Food (2005), 8(3), 281-290. Publisher: Mary Ann Liebert, Inc., CODEN:
JMFOFJ ISSN: 1096-620X. Journal; General Review written in English. CAN 144:232126 AN 2005:1020091 CAPLUS
Abstract
A review. Polyphenolic flavonoids are among a wide variety of phytochems. present in the human diet. Basic research, animal
model, and human studies suggest flavonoid intake may reduce the risk of several age-related chronic diseases. The vast no. of
flavonoids and mixts. of their subclasses, including flavonols, flavones, and flavanones, and the variety of agricultural practices that
affect their concn. in foods have presented a challenge to the development of adequate food compn. databases for these compds.
Nonetheless, dietary assessments have been applied to cohort and case-control epidemiol. studies, and several reveal an inverse
assocn. with risk of some forms of cancer, cardiovascular disease, and other chronic conditions. Those observational studies that
have examd. these relationships with regard to flavonols, flavones, and flavanones are reviewed. The requirement for caution in
interpreting these studies is discussed with regard to the limited information available on the bioavailability and biotransformation of
these flavonoids. As the totality of the available evidence on these flavonoids suggests a role in the prevention of cancer and
cardiovascular disease, further research is warranted, particularly in controlled clin. trials.
Answer 555:
Determination of flavanone content and antioxidant activity of Citrus aurantium. Hosseinimehr, S. J. Department of
Medicinal Chemistry, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran. Chemistry (Rajkot, India)
(2004), 1(9), 635-638. Publisher: Trade Science Inc., CODEN: CHEMCT ISSN: 0972-8376. Journal written in English. CAN
Abstract
The flavonoid content of citrus ext. were investigated with using Mg method, and its antioxidant activity was detd. with DPPH and
H2O2 assay. Hesperidin was shown to be the main flavonoid present in citrus family, it is chelated with Mg in an acidic envuronment
and displays a cherry red color having UV absorbance max. at 560 nm. Flavanone content was 9.2±017 g/100g in citrus aurantium
peel ext. Citrus ext. showed excellent scavenging effects on stable radical DPPH at a concn. of 1.6 mg/mL. Citrus ext. showed
H2O2 scavenging ability. These results demonstrated that citrus ext. possess high amt. of flavonoids and excellent antioxidant
activity.
Answer 556:
flavanone
Conversion from arenes having a benzene ring to those having a picolinic acid using Escherichia coli that express bacterial
genes involved in biphenyl catabolism. Shindo, Kazutoshi; Kagami, Osamu; Misawa, Norihiko; Furukawa, Kensuke. (Marine
Biotechnology Institute Co., Ltd., Japan). PCT Int. Appl. (2005), 60 pp. CODEN: PIXXD2 WO 2005085435 A1 20050915
EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD,
MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT,
TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT,
LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in Japanese. Application: WO
2005-JP2755 20050222. Priority: JP 2004-61238 20040304. CAN 143:304749 AN 2005:1004874 CAPLUS (Copyright (C) 2008

WO 2005085435 A1 20050915 WO 2005-JP2755 20050222
RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA,
ZM, ZW
EP 1726645 A1 20061129 EP 2005-719369 20050222
R: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LI, LT, LU, MC, NL, PL, PT,
RO, SE, SI, SK, TR
JP 2004-61238 A 20040304
WO 2005-JP2755 W 20050222
Abstract
A process for producing picolinic acid compds. from phenyl-contg. arom. compds. by enzymic synthesis in engineered microbes
expressing biphenyl catabolic enzyme genes, is disclosed. The process, which is for producing picolinic acid compds., comprises
reacting phenyl-contg. arom. compds. represented by the following formula (I; Y = (substituted) heterocycly, Ph, or cyclic
hydrocarbyl; Y ≠ diphenylacetylene; X = single bond, (substituted)-C1-4-alkylene or alkenylene) with an arom. ring dioxygenase, an
arom. ring dihydrodiol dehydrogenase, and an arom. ring diol dioxygenase to obtain picolinic acid compds. (II; X,Y as in I). The
comprehensive bioconversion of arom. compds. with a benzene ring to a picolinic acid was achieved with a recombinant Escherichia
coli strain that expressed the six genes involved in biphenyl catabolism, these being the bphA1(2072)A2A3A4 genes encoding the
evolved biphenyl dioxygenase, the bphB gene encoding dihydrodiol dehydrogenase, and the bphC gene encoding catechol
2,3-dioxygenase.
flavanone
CO 2 H
N
Y X Y X
I II
Answer 557:
New synthesis of flavanones catalyzed by L-proline. Chandrasekhar, S.; Vijeender, K.; Reddy, K. Venkatram. Indian Institute
of Chemical Technology, Hyderabad, India. Tetrahedron Letters (2005), 46(41), 6991-6993. Publisher: Elsevier B.V., CODEN:
TELEAY ISSN: 0040-4039. Journal written in English. CAN 143:422169 AN 2005:980491 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Proline is utilized as an efficient organocatalyst for the synthesis of substituted flavanones and chalcones in good yields. The
efficiency of the catalyst was proved with a variety of substrates ranging from electron-deficient to electron-rich aryl aldehydes and
2-hydroxyacetophenones.
Answer 558:
Mechanisms and preclinical efficacy of silibinin in preventing skin cancer. Singh, Rana P.; Agarwal, Rajesh. Department of
Pharmaceutical Sciences, School of Pharmacy, University of Colorado at Denver and Health Sciences Center, Denver, CO, USA.
European Journal of Cancer (2005), 41(13), 1969-1979. Publisher: Elsevier Ltd., CODEN: EJCAEL ISSN: 0959-8049. Journal;
General Review written in English. CAN 144:100090 AN 2005:978152 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
A review. Eukaryotic cellular machineries including the genome face continuous challenge from environmental deleterious agents, as
well as from the by products of their own metab. Our skin is the most important barrier. It protects us from xenobiotic and genotoxic
agents including UV solar radiation and potential carcinogens, which are notorious for causing skin cancer. There is a rise in
non-melanoma skin cancer (NMSC), which is diagnosed in more than a million people every year in the United States alone, and is also
prevalent in the other Western countries. In addn. to sunscreens, chemoprevention of skin cancer by natural non-toxic compds. is
suggested as an effective strategy to prevent the incidence of skin cancer. Our extensive animal studies on silibinin, a non-toxic
bioactive component in milk thistle, suggest that it has a strong potential to prevent skin cancer incidence, promotion and progression
in response to chem. carcinogens and tumor promoters as well as UV radiation. Our data suggest that silibinin has multiple targets in
the cell, and can be protective against the harmful effects of cytotoxic agents such as reactive oxygen species and inflammation.
Further, silibinin modulates mitogenic and survival signaling, p53, Cip1/p21 and other cell cycle regulatory mols. to prevent
UVB-induced skin carcinogenesis. Our ongoing studies also suggest the pos. effect of silibinin on the repair of UVB-induced DNA
damage in mouse skin. Overall, the protective efficacy of silibinin against skin cancer is supported by sound mechanistic rationale in
animal and cell culture studies, and suggests its potential use for humans.
Answer 559:
flavanone
Comparative enzymology of 11β-hydroxysteroid dehydrogenase type 1 from six species. Arampatzis, Spyridon; Kadereit,
Bert; Schuster, Daniela; Balazs, Zoltan; Schweizer, Roberto A. S.; Frey, Felix J.; Langer, Thierry; Odermatt, Alex. Division of
Nephrology and Hypertension, Department of Clinical Research, University of Berne, Bern, Switz. Journal of Molecular
Endocrinology (2005), 35(1), 89-101. Publisher: Society for Endocrinology, CODEN: JMLEEI ISSN: 0952-5041. Journal written in
Abstract
11β-Hydroxysteroid dehydrogenase type 1 (11β-HSD1), catalyzing the intracellular activation of cortisone to cortisol, is currently
considered a promising target to treat patients with metabolic syndrome; hence, there is considerable interest in the development of
selective inhibitors. For preclin. tests of such inhibitors, the characteristics of 11β-HSD1 from the commonly used species have to be
known. Therefore, we detd. differences in substrate affinity and inhibitor effects for 11β-HSD1 from six species. The differences in
catalytic activities with cortisone and 11-dehydrocorticosterone were rather modest. Human, hamster and guinea-pig 11β-HSD1
displayed the highest catalytic efficiency in the oxoredn. of cortisone, while mouse and rat showed intermediate and dog the lowest
activity. Murine 11β-HSD1 most efficiently reduced 11-dehydrocorticosterone, while the enzyme from dog showed lower activity than
those from the other species. 7-Ketocholesterol (7KC) was stereospecifically converted to 7β-hydroxycholesterol by recombinant
11β-HSD1 from all species analyzed except hamster, which showed a slight preference for the formation of 7α-hydroxycholesterol.
Importantly, guinea-pig and canine 11β-HSD1 displayed very low 7-oxoreductase activities. Furthermore, we demonstrate significant
species-specific variability in the potency of various 11β-HSD1 inhibitors, including endogenous compds., natural chems. and
pharmaceutical compds. The results suggest significant differences in the three-dimensional organization of the hydrophobic
substrate-binding pocket of 11β-HSD1, and they emphasize that species-specific variability must be considered in the interpretation of
results obtained from different animal expts. The assessment of such differences, by cell-based test systems, may help to choose
the appropriate animal for safety and efficacy studies of novel potential drug candidates.
Answer 560:
Two different mutations are involved in the formation of white-flowered gentian plants. Nakatsuka, Takashi; Nishihara,
Masahiro; Mishiba, Keiichiro; Yamamura, Saburo. Iwate Biotechnology Research Center, Kitakami, Iwate, Japan. Plant Science
(Amsterdam, Netherlands) (2005), 169(5), 949-958. Publisher: Elsevier B.V., CODEN: PLSCE4 ISSN: 0168-9452. Journal written
Abstract
Japanese cultivated gentian plants have naturally blue flowers, but some white-flowered cultivars are being bred through the utilization
of spontaneous mutants. To det. the mol. basis of white coloration in gentian flowers, we compared two white-flowered cultivars Homoi
and Polano White to a blue-flowered cultivar Maciry using biochem. and mol. approaches. High performance liq. chromatog. (HPLC)
analyses showed that flavone levels in cv. Polano White were only about one-half the amts. measured in the other two cultivars, while
anthocyanins were absent in the two white-flowered cultivars compared to cv. Maciry in which high levels accumulated. Northern blot
anal. of 10 flavonoid biosynthetic structural genes, previously reported to be temporally regulated in cv. Maciry showed that cv.
Homoi lacked transcripts for the anthocyanidin synthase (ANS) gene while cv. Polano White had decreased expressions for ANS as
well as for chalcone synthase (CHS), flavanone 3-hydroxylase (F3H), flavonoid 3',5'-hydroxylase (F3',5'H), dihydroflavonol
4-reductase (DFR), UDP-glucose:flavonoid 3-glucosyltransferase (3GT) and anthocyanin 5-arom. acyltransferase (5AT). Southern blot
anal. confirmed the deficiency of one of two ANS loci in cv. Homoi. Transient expression of ANS in flower petals also strongly
suggested that white flowers of cv. Homoi were derived from ANS mutation. Furthermore, anal. of stress-induced flower pigmentation
suggested that rather than mutations in multiple structural genes being the cause, a defect in one or more regulatory factors controlling
the later steps of flavonoid biosynthesis is responsible for white coloration in cv. Polano White.
flavanone
Answer 561:
Metabolic engineering of isoflavonoid biosynthesis in alfalfa. Deavours, Bettina E.; Dixon, Richard A. Plant Biology
Division, Samuel Roberts Noble Foundation, Ardmore, OK, USA. Plant Physiology (2005), 138(4), 2245-2259. Publisher:
American Society of Plant Biologists, CODEN: PLPHAY ISSN: 0032-0889. Journal written in English. CAN 143:418993 AN
Abstract
The potential health benefits of dietary isoflavones have generated considerable interest in engineering the synthesis of these
phytoestrogens into plants. Genistein glucoside prodn. (up to 50 nmol g-1 fresh wt.) was engineered in alfalfa (Medicago sativa) leaves
by constitutive expression of isoflavone synthase from Medicago truncatula (MtIFS1). Glucosides of biochanin A
(4'-O-methylgenistein) and pratensein (3'-hydroxybiochanin A) also accumulated. Although MtIFS1 was highly expressed in all organs
examd., genistein accumulation was limited to leaves. MtIFS1-expressing lines accumulated several addnl. isoflavones, including
formononetin and daidzein, in response to UV-B or Phoma medicaginis, whereas the chalcone and flavanone precursors of these
compds. accumulated in control lines. Enhanced accumulation of the phytoalexin medicarpin was obsd. in P. medicaginis-infected
leaves of MtIFS1-expressing plants. Microarray profiling indicated that MtIFS1 expression does not significantly alter global gene
expression in the leaves. Our results highlight some of the challenges assocd. with metabolic engineering of plant natural products,
including tissue-specific accumulation, potential for further modification by endogenous enzyme activities (hydroxylation, methylation,
and glycosylation), and the differential response of engineered plants to environmental factors.
Answer 562:
Stability of methanolic extract activity for leaves, peels and citrus seeds under UV irradiation. Shaker, Emad S.
Agricultural Chemistry Department, Faculty of Agriculture, Minia University, Minia, Egypt. Special Publication - Royal Society of
Chemistry (2005), 300(Food Flavor and Chemistry), 472-483. Publisher: Royal Society of Chemistry, CODEN: SROCDO ISSN:
Abstract
Grapefruit (Citrus paradise Macf.) (gr); Valencia orange (C. sinensis Osbeck) (vi); Sour orange (C. aurantium L.) (lr); Lemon (C. limon
L.) (ad); Balady mandarin (C. reticulate Blanco) (y); Balady orange (C. sinensis Osbeck) (or) methanolic HCl exts. have been analyzed
for antioxidative properties in their leaves L, peels P and seeds S. For the last two citrus, only leaves were extd. and evaluated. The
results showed that grapefruit leaves, lemon seeds and valencia peel exts. have the highest antioxidative property (AOA). Comparing
phenol content, lemon leaves, grapefruit seeds and sour orange peel exts. have the highest phenolic amts. of all analyzed samples. In
spite of that citrus seeds contain the lowest mean phenols amts., they showed mean AOA more than 93% comparing to that for
control. The chem. compn. was investigated using GC-MS for the citrus seed methanolic exts. (SME). Three major peaks were
detected and identified as hexadecanoic acid Me ester (I), flavanone derivs. specifically a pentahydroxy dimethoxy flavone (II), and
Kaempferide (III) a methoxy deriv. The grapefruit seed methanolic ext. has the highest amt. of compds. (I, III). Valencia seed ext.
has the highest amt. of compd. (II). Valencia seed ext. has the lowest content of compds. (I, III) and the lemon seed ext. has the
lowest content for compd. (II).
Answer 563:
flavanone
Method of quantitative determination of flavanones. Menteshashvili, M.; Samsonia, Sh.; Shalashvili, A.; Targamadze, I. Tbilisi
State Univ., Tbilisi, Georgia. Sakartvelos Mecnierebata Akademiis Macne, Kimiis Seria (2005), 31(1-2), 181-183. Publisher:
Proizvodstvenno-IzdatelÏskoe ObÏedinenie "Metsniereba", CODEN: IANKEJ Journal written in English. CAN 145:58540 AN
Abstract
A method for quant. detn. of flavanones existing in mandarin (Citrus unshiu) fruit skin is described. Maximal extn. of flavanones from
the air-dried skin was performed with methanol and the measurement was by spectrometry.
Answer 564:
Kinetics of radical-scavenging activity of hesperetin and hesperidin and their inhibitory activity on COX-2 expression.
Hirata, Atsusi; Murakami, Yukio; Shoji, Masao; Kadoma, Yoshinori; Fujisawa, Seiichiro. Department of Oral Diagnosis, Meikai
University School of Dentistry, Saitama, Japan. Anticancer Research (2005), 25(5), 3367-3374. Publisher: International Institute
of Anticancer Research, CODEN: ANTRD4 ISSN: 0250-7005. Journal written in English. CAN 143:318303 AN 2005:966362
Abstract
The radical-scavenging activities of the flavanones hesperetin and hesperidin were investigated by differential scanning calorimetry
(DSC) monitoring of the polymn. of Me methacrylate initiated by 2,2'-azobisisobutyronitrile (AIBN, an R.bul. radical) or benzoyl
peroxide (BPO, a PhCOO.bul. radical) at 70°C under nearly anaerobic conditions. Their stoichiometric factor (no. of free radicals
trapped by one mole of antioxidant moiety (n)) and the ratio of the rate const. of inhibition to that of propagation (kinh/kp) were detd.
and compared with that for trolox. The n value declined in the order trolox (2.0) > hesperetin (0.8) > hesperidin (0.2) in the AIBN
system, whereas it declined in the order hesperetin (0.9) > trolox (0.1) > hesperidin (0.0) in the BPO system. The kinh/kp value
declined in the order hesperidin (195) > hesperetin (33) > trolox (12) in the AIBN system, whereas it declined in the order hesperidin
(362) > trolox (127) > hesperetin (18) in the BPO system. The n value of about 1 for hesperetin with a relatively small kinh/kp value
suggests the formation of dimers, as a result of the coupling reaction of phenolic monomers. In contrast, n values < < 1 for hesperidin
and trolox in the BPO system resulted in very high values for kinh/kp Hesperidin was also much more able to suppress the growth of
Me methacrylate radicals, although its n value was small, suggesting that this compd. may also suppress polyunsatd. fatty acid
radicals. In the concn. range 250-500 μM, hesperetin and hesperidin showed potent inhibition of LPS-induced expression of the COX-2
gene in RAW 264.7 cells, suggesting the anti-inflammatory activity of these compds. The ability of hesperetin and hesperidin to
suppress COX-2 gene expression may be a consequence of their antioxidant activity.
Answer 565:
CCC sample cutting for isolation of prenylated phenolics from hops. Chadwick, Lucas R.; Fong, Harry H. S.; Farnsworth,
Norman R.; Pauli, Guido F. UIC/NIH Center for Botanical Dietary Supplements Research, Department of Medicinal Chemistry and
Pharmacognosy, Program for Collaborative Research in the Pharmaceutical Sciences, College of Pharmacy, University of Illinois at
Chicago, Chicago, IL, USA. Journal of Liquid Chromatography & Related Technologies (2005), 28(12-13), 1959-1969. Publisher:
Taylor & Francis, Inc., CODEN: JLCTFC ISSN: 1082-6076. Journal written in English. CAN 144:166583 AN 2005:965909
Abstract
flavanone
One of the most potent estrogenic substances from the plant kingdom is the prenylated flavanone, 8-prenylnaringenin (8PN), present
in hops (Humulus lupulus L., Cannabaceae) in low (<10 ppm) concns. The prenylated chalcone desmethylxanthohumol (DMX), which is
also present in this plant material, serves as a precursor to 8PN. A method for the preparative isolation of these and related bioactive
phytochems. has been developed that involves the use of multiple chromatog. techniques including complementary countercurrent
chromatog. (CCC) solvent systems. This paper describes the isolation of 8PN and DMX employing "sample-cutting CCC". The
Hexanes-EtOAc-MeOH-H2O (HEMWat) solvent systems found to be effective for isolation of prenylated phenolics from hops range
from HEMWat 8-2-8-2 for diprenylxanthohumol and 6,8-diprenylnaringenin, to HEMWat 6-4-6-4 for xanthohumol (XH),
6-prenylnaringenin (6PN) and 8PN, to HEMW at 5-5-5-5 for DMX, hydroxylated derivs. of XH, and humulinones.
Answer 566:
High-performance liquid chromatographic enantioseparation of flavanones on 2-hydroxy-3-methacryloyloxypropyl

β-cyclodextrin copolymer coated silica phase. Carbonnier, Benjamin; Janus, Ludovic; Morcellet, Michel. Laboratoire de Chimie
Macromoleculaire, UMR CNRS 8009, Universite des Sciences et Technologies de Lille, Villeneuve d'Ascq, Fr. Journal of
Chromatographic Science (2005), 43(7), 358-361. Publisher: Preston Publications, CODEN: JCHSBZ ISSN: 0021-9665. Journal
Abstract
Chromatog. resoln. of four flavanones is achieved by reversed-phase HPLC on a chiral stationary phase based on silica coated with a
(2-hydroxy-3-methacryloyloxypropyl β-cyclodextrin-co-N-vinylpyrrolidone) copolymer. The influence of the mobile phase water
content and the nature of the org. modifier on the retention and resoln. is evaluated. Monosubstituted flavanones are better resolved
than the unsubstituted one. Nevertheless, the 6- and 7-methoxy substituents enhance retention and chiral recognition to polymeric
β-cyclodextrin stationary phase less than the 6-hydroxy group. (c) 2005 Preston Publications.
Answer 567:
Reactions of α-hydroxyethyl radicals with flavonoids of various structures. Hryntsevich, I. B.; Shadyro, O. I. Department
of Chemistry of the Belarussian State University, Minsk, Belarus. Bioorganic & Medicinal Chemistry Letters (2005), 15(19),
4252-4255. Publisher: Elsevier B.V., CODEN: BMCLE8 ISSN: 0960-894X. Journal written in English. CAN 143:367110 AN
Abstract
Flavonoids (FL) are able to reduce, add or oxidize α-hydroxyethyl radicals (HER). The probability of these processes to occur
depends on the structure of the FL under study. Namely, to cause redn. of HER, the presence of hydroxyl groups is necessary, and
to effect oxidn. or addn. of HER, the presence of a carbonyl group at C4 and a C2-C3 double bond in the C ring is required.
Answer 568:
Natural Products as Scaffolds for Chemical Diversification: Solution-Phase Parallel Synthesis of a Series of Naringin
Analogs. Hanessian, Stephen; Kothakonda, Kiran Kumar. Department of Chemistry, University of Montreal, Montreal, QC,
Can. Journal of Combinatorial Chemistry (2005), 7(6), 837-842. Publisher: American Chemical Society, CODEN: JCCHFF ISSN:
flavanone
Abstract
The flavanone glycoside naringin hydrate is widely abundant in various citrus plants. As an ongoing effort toward the exploitation of
natural products as scaffolds for chem. diversification at readily accessible positions, we have prepd. a series of analogs of naringin
in which the 6-hydroxyl group of the β-D-glucopyranosyl subunit was converted to sulfonamides, amides, urethanes, and secondary
and tertiary amines via the corresponding 6-amino deriv. using a soln.-phase parallel array protocol.
Answer 569:
Isolation of a novel flavanone 6-glucoside from the flowers of Carthamus tinctorium (Honghua) by high-speed
counter-current chromatography. Zhao, Mingbo; Ito, Yoichiro; Tu, Pengfei. School of Pharmaceutical Sciences, Peking
University Health Science Center, Beijing, Peop. Rep. China. Journal of Chromatography, A (2005), 1090(1-2), 193-196.
Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. CAN 143:382028 AN 2005:901347
Abstract
A novel flavanone glycoside, (2S)-4',5,6,7-tetrahydroxyflavavone 6-O-β--glucopyranoside was isolated from the Et acetate ext. of the
flowers of Carthamus tinctorium by high-speed counter-current chromatog. (HSCCC). Using an optimized two-phase solvent system
composed of Et acetate-methanol-water (5:1:5, vol./vol.), target compd. (52 mg) with purity of 98.0% was obtained from 2.0 g of
sample by HSCCC in seven times run. The structure of the target compd. was elucidated by spectroscopic methods including IR, MS,
1D and 2D NMR techniques.
Answer 570:
Microwave-accelerated solvent-free synthesis of flavanones. Sagrera, Gabriel J.; Seoane, Gustavo A. Departamento de
Quimica Organica, Facultad de Ciencias Universidad de la Republica, Montevideo, Urug. Journal of the Brazilian Chemical Society
(2005), 16(4), 851-856. Publisher: Sociedade Brasileira de Quimica, CODEN: JOCSET ISSN: 0103-5053. Journal written in English.
Abstract
Microwave irradn. of chalcones under solvent-free conditions resulted in a green chem. procedure for the prepn. of flavanones in very
good yields. Using an unmodified household microwave oven, different mineral supports, and catalysts were tested. By irradn. of
chalcones with 30% TFA over silica gel, eleven known flavanones and five new compds. were prepd. in high yields.
Answer 571:
Remedy containing 3-hydroxy-3-methylglutaryl-CoA reductase inhibitor and/or cell foaming inhibitor. Enoki, Tatsuji; Kudo,
Yoko; Sugiyama, Katsumi; Ohnogi, Hiromu; Sagawa, Hiroaki; Kato, Ikunoshin. (Takara Bio Inc., Japan). PCT Int. Appl. (2005),
91 pp. CODEN: PIXXD2 WO 2005074906 A1 20050818 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW,
BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP,
KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO,
flavanone
RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT,
BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD,
TG. Patent written in Japanese. Application: WO 2005-JP1655 20050204. Priority: JP 2004-31173 20040206. CAN 143:199938

WO 2005074906 A1 20050818 WO 2005-JP1655 20050204
ZW
JP 2004-31173 A 20040206
Abstract
It is intended to provide a drug, a food, a drink or a feed for treating or preventing diseases, wherein an effect of inhibiting
3-hydroxy-3-methylglutaryl-CoA reductase and/or an effect against cell foaming are needed for the prevention or treatment,
characterized by contg., as the active ingredient, at least one compd. selected from the group consisting of chalcone compds.,
flavanone compds., 3',4'-dihydroseseline compds., derivs. thereof and salts thereof. The above-described drug, food, drink or feed is
useful in treating or preventing, for example, hyperlipemia, arteriosclerosis and various diseases caused mainly thereby. For example,
xanthoangelol was isolated from Angelica Keiskei root ext., and examd. for its HMG-CoA reductase inhibitory effect in vitro.
Answer 572:
Structural and mechanistic studies on anthocyanidin synthase catalyzed oxidation of flavanone substrates: the effect of C-2
stereochemistry on product selectivity and mechanism. Welford, Richard W. D.; Clifton, Ian J.; Turnbull, Jonathan J.; Wilson,
Stuart C.; Schofield, Christopher J. Chemical Research Laboratory, Department of Chemistry, Oxford Centre for Molecular
Sciences, Oxford, UK. Organic & Biomolecular Chemistry (2005), 3(17), 3117-3126. Publisher: Royal Society of Chemistry,
CODEN: OBCRAK ISSN: 1477-0520. Journal written in English. CAN 143:381656 AN 2005:800501 CAPLUS (Copyright (C)
Abstract
During the biosynthesis of the tricyclic flavonoid natural products in plants, oxidative modifications to the central C-ring are catalyzed
by Fe(II) and 2-oxoglutarate dependent oxygenases. The reactions catalyzed by three of these enzymes; flavone synthase I,
flavonol synthase and anthocyanidin synthase (ANS), are formally desaturations. In comparison, flavanone 3β-hydroxylase
catalyzes hydroxylation at the C-3 pro-R position of 2S-naringenin. Incubation of ANS with the unnatural substrate (±)-naringenin
results in predominantly C-3 hydroxylation to give cis-dihydrokaempferol as the major product; trans-dihydrokaempferol and the
flavanone
desatn. product, apigenin are also obsd. Labeling studies have demonstrated that some of the formal desatn. reactions catalyzed by
ANS proceed via initial C-3 hydroxylation followed by dehydration at the active site. We describe analyses of the reaction of ANS
with 2S- and 2R-naringenin substrates, including the anaerobic crystal structure of an ANS-Fe-2-oxoglutarate-naringenin complex.
Together the results reveal that for the 'natural' C-2 stereochem. of 2S-naringenin, C-3 hydroxylation predominates (>9:1) over desatn.,
probably due to the inaccessibility of the C-2 hydrogen to the iron center. For the 2R-naringenin substrate, desatn. is significantly
increased relative to C-3 hydroxylation (.apprx.1:1); this is probably a result of both the C-3 pro-S and C-2 hydrogen atoms being
accessible to the reactive oxidizing intermediate in this substrate. In contrast to the hydroxylation-elimination desatn. mechanism for
some ANS substrates, the results imply that the ANS catalyzed desatn. of 2R-naringenin to form apigenin proceeds with a
syn-arrangement of eliminated hydrogen atoms and not via an oxygenated (gem-diol) flavonoid intermediate. Thus, by utilizing
flavonoid substrates with different C-2 stereochemistries, the balance between C-3 hydroxylation or C-2, C-3 desatn. mechanisms can
be altered.
Answer 573:
Characterization and bioscreening of a new triterpenoid and a flavanone isolated from Salvia nubicola. Ali, Muhammad S.;
Ahmed, Shakeel; Ibrahim, Syed A.; Tareen, Rasool B. H. E. J. Research Institute of Chemistry, International Center for Chemical
Sciences, University of Karachi, Karachi, Pak. Chemistry & Biodiversity (2005), 2(7), 910-916. Publisher: Verlag Helvetica
Chimica Acta AG, CODEN: CBHIAM ISSN: 1612-1872. Journal written in English. CAN 144:146515 AN 2005:781141 CAPLUS
Abstract
A new lupane triterpenoid, 3α-hydroxy-20-oxo-30-norlupane (I) plus its β epimer (II), and a new flavanone (nubatin; III) have been
isolated from Salvia nubicola collected from Quetta, Pakistan. The structures of these constituents were elucidated with the aid of
spectroscopic techniques, including two-dimensional NMR and NOE expts. Both the metabolites were found to be moderately
bio-active.
flavanone
CH 3 CH 3
CO CO
H Me H Me
Me Me H Me Me H
H Me H Me
HO HO
Me H Me H
Me I Me II
OH
OH
MeO O
MeO
OH O III
Answer 574:
Determination of flavonoids in citrus juices by micro-HPLC-ESI/MS. Dugo, Paola; Lo Presti, Maria; Oehman, Marcus; Fazio,
Alessia; Dugo, Giovanni; Mondello, Luigi. Dipartimento di Chimica Organica e Biologica, Facolta di Scienze, Universita di Messina,
Messina, Italy. Journal of Separation Science (2005), 28(11), 1149-1156. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA,
Abstract
Flavonoids are a large class of naturally occurring arom. secondary plant metabolites. They constitute one of the most characteristic
classes found in nature and more than 4000 flavonoids have been identified and divided into several subclasses. Flavonoids have
several effects on human health, mainly related to their antioxidant activity. As a result of the increased interest in the biol. active
compds. in food, many research studies have investigated the detection and quantification of antioxidants. Citrus plants are of great
interest since they accumulate large amts. of flavonoids and fruit and juices of these species are consumed in large quantities.
Despite the extensive research performed on Citrus flavonoids, many compds. still remain unidentified. In this work, flavonoids of 5
citrus juices: lemon, grapefruit, bergamot, orange, and mandarin were analyzed by micro-HPLC coupled online with an MS detector
equipped with an ESI source operating in neg. mode. The use of microcolumn HPLC greatly enhanced detection performance. In total,
20 flavonoids of two different subclasses (flavanone and flavone glycosides) were identified with the help of retention data and MS
spectral information.
flavanone
Answer 575:
Impact of Induced Fit on Ligand Binding to the Androgen Receptor: A Multidimensional QSAR Study To Predict
Endocrine-Disrupting Effects of Environmental Chemicals. Lill, Markus A.; Winiger, Fabienne; Vedani, Angelo; Ernst, Beat.
Institute for Molecular Pharmacy, University of Basel, Basel, Switz. Journal of Medicinal Chemistry (2005), 48(18), 5666-5674.
Publisher: American Chemical Society, CODEN: JMCMAR ISSN: 0022-2623. Journal written in English. CAN 143:243261 AN
Abstract
The authors investigated the influence of induced fit of the androgen receptor binding pocket on free energies of ligand binding. On the
basis of a novel alignment procedure using flexible docking, mol. dynamics simulations, and linear-interaction energy anal., the authors
simulated the binding of 119 mols. representing six compd. classes. The superposition of the ligand mols. emerging from the
combined protocol served as input for Raptor, a receptor-modeling tool based on multidimensional QSAR allowing for ligand-dependent
induced fit. Throughout the authors' study, protein flexibility was explicitly accounted for. The model converged at a cross-validated
R2 = 0.858 (88 training compds.) and yielded a predictive R2 = 0.792 (26 test compds.), thereby predicting the binding affinity of all
compds. close to their exptl. value. The authors then challenged the model by testing five mols. not belonging to compd. classes used
to train the model: the IC50 values were predicted within a factor of 4.5 compared to the exptl. data. The demonstrated predictivity of
the model suggests that the authors' approach may well be beneficial for both drug discovery and the screening of environmental
chems. for endocrine-disrupting effects, a problem that has recently become a cause for concern among scientists, environmental
advocates, and politicians alike.
Answer 576:
Investigation of the biosynthesis of 3-deoxyanthocyanins in Sinningia cardinalis. Winefield, Chris S.; Lewis, David H.;
Swinny, Ewald E.; Zhang, Huaibi; Arathoon, H. Steve; Fischer, Thilo C.; Halbwirth, Heidrun; Stich, Karl; Gosch, Christian; Forkmann,
Gert; Davies, Kevin M. New Zealand Institute for Crop and Food Research Limited, Palmerston North, N. Z. Physiologia
Plantarum (2005), 124(4), 419-430. Publisher: Blackwell Publishing Ltd., CODEN: PHPLAI ISSN: 0031-9317. Journal written in
Abstract
3-Deoxyanthocyanins provide bright orange-red colors to flowers of some members of the Gesneriaceae, including sinningia (Sinningia
cardinalis). We examd. 3-deoxyanthocyanin biosynthesis in sinningia, in particular, the expression of key flavonoid biosynthetic
genes and the activities of the encoded proteins. Two abundant 3-deoxyanthocyanins, luteolinidin 5-O-glucoside and apigeninidin
5-O-glucoside, three flavone glycosides, luteolin 7-O-glucoside, luteolin 7-O-glucuronide and apigenin 7-O-glucuronide, and the cinnamic
acid verbascoside were identified in sinningia petal tissue. Small amts. of a 3-hydroxyanthocyanin were also detected in a limited
region of the petal. CDNA clones for three flavonoid enzymes, flavanone 3-hydroxylase (F3H), dihydroflavonol
4-reductase/flavanone 4-reductase (DFR/FNR) and anthocyanidin synthase (ANS), were isolated from a sinningia cDNA library made
from petal RNA and used to measure transcript abundance during petal development. Only very low levels of F3H transcript were
detected, while DFR/FNR transcript was highly abundant. ANS transcript levels were intermediate between these two. The F3H cDNA
was shown to encode a functional F3H protein by complementation of the phenotype of an Antirrhinum majus F3H mutant. The
recombinant DFR/FNR had activity against both flavanone and dihydroflavonol substrates to a comparable extent. The results
suggest a mechanism of 3-deoxyflavonoid biosynthesis in sinningia similar to that reported for Zea mays, in which lack of F3H
activity allows action of the DFR/FNR on flavanone substrates and prodn. of flavan-4-ols. These are then likely converted to
3-deoxyanthocyanins through the action of the ANS and subsequent glucosylation.
flavanone
Answer 577:
Methacryloylpropyl-β-cyclodextrin and vinylpyrrolidone copolymers: Synthesis and characterization as potential chiral

selector. Carbonnier, B.; Janus, L.; Deratani, A.; Morcellet, M. Laboratoire de Chimie Macromoleculaire, UPRESA CNRS 8009,
Universite des Sciences et Technologies de Lille, Villeneuve d'Ascq, Fr. Journal of Applied Polymer Science (2005), 97(6),
2364-2374. Publisher: John Wiley & Sons, Inc., CODEN: JAPNAB ISSN: 0021-8995. Journal written in English. CAN 143:359184
Abstract
The free radical copolymn. of vinylpyrrolidone (VP) with 2-hydroxy-3-methacryloyloxypropyl β-cyclodextrin (βW7 MAHP), a deriv. of
hydroxypropyl β-cyclodextrin (CD) substituted by polymerizable methacryloyl groups, is carried out in water by varying the molar ratio
of the comonomers. The higher the molar ratio of βW7 MAHP to VP, the larger the molar mass of the water-sol. copolymer. A size
exclusion chromatog. anal. coupled with multiangle laser light scattering detection (SEC-MALLS) suggests that VP-rich copolymers with
a mass-av. molar mass (MM) of about 2.5 × 104 g mol-1 may consist of βW7 MAHP dimers, trimers, and oligomers contg. few CD
units whereas βW7 MAHP rich copolymers with an MM of about 5.5 × 106 g mol-1 are likely to be dominated by crosslinked polymer
materials. βW7 MAHP-co-VP copolymers coated on porous silica are used as high-performance liq. chromatog. chiral selectors. The
effects of the structural features of the guest mol. and the characteristics of the chiral stationary phases on the retention and resoln.
are evaluated. SEC-MALLS detection shows that, by varying the comonomer feed, copolymers with different molar masses and
macromol. structures are formed. The chiral sepn. ability of Copo VP is evaluated toward enantiomers having one or more arom. rings
as a function of the amt. of copolymer adsorbed onto the silica surface, the βW7 MAHP content, and the concn. of solute. The
column combining the greater amts. of adsorbed copolymer and βW7 MAHP exhibits better resolving power. Moreover, the size,
geometry, and functionality of the guest mol. are important factors that strongly affect the enantioselectivity.
Answer 578:
Flavanones isolated from Ricinus Communis L. (Euphorbiaceae). Bahroun, A.; Ben Ameur, N.; Damak, M. Laboratoire de
chimie des Substances Naturelles, Faculte des Sciences de Sfax, Sfax, Tunisia. Journal de la Societe Chimique de Tunisie
(2002), 4(11), 1427-1431. Publisher: Societe Chimique de Tunisie, CODEN: JSCTDP ISSN: 0253-1208. Journal written in French.
Abstract
Two flavanones have been isolated from the pericarps of Ricinus communis (Euphorbiaceae). By means of spectroscopic methods
their structures, were established as naringenin 7-O-(3''-p-coumaroylglucoside) and naringenin 7-O-(3'',6''-di-p-coumarylglucoside).
Answer 579:
Red grain colour gene (R) of wheat is a Myb-type transcription factor. Himi, Eiko; Noda, Kazuhiko. Research Institute for
Bioresources, Okayama University, Kurashiki, Japan. Euphytica (2005), 143(3), 239-242. Publisher: Springer, CODEN:
EUPHAA ISSN: 0014-2336. Journal written in English. CAN 144:268250 AN 2005:710259 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
flavanone
Red pigment of wheat grain was reported to be polyphenol compds., phlobaphene or proanthocyanidin, which were synthesized through
the flavonoid biosynthesis pathway. We examd. the expression of four genes in the flavonoid pathway in developing wheat grains:
chalcone synthase (CHS), chalcone isomerase (CHI), flavanone 3-hydroxylase (F3H), and dihydroflavonol 4-reductase (DFR). The
expression of these genes in the white-grained wheat lines was reduced, compared with that in the red-grained wheats. These results
suggest that the R genes for grain color, located on the long arms of chromosomes 3A, 3B and 3D, are transcriptional activators of the
flavonoid synthesis genes. We identified three Myb-type transcription factors (Tamyb10-A1 on 3A, Tamyb10-B1 on 3B and
Tamyb10-D1 on 3D), which were also located in the same region as the R loci, and were expressed predominantly in developing grains.
In wheat lines with the recessive allele r3 (3B) Tamyb10-B1 had a deletion which caused a frame-shift in its open reading frame.
Tamyb10-A1, and -D1 were not expressed in wheats with r2 (3A) and r1 (3D).
Answer 580:
Flavanones in citrus fruit: Structure-antioxidant activity relationships. Di Majo, Danila; Giammanco, Marco; La Guardia,
Maurizio; Tripoli, Elisa; Giammanco, Santo; Finotti, Enrico. Institute of Physiology and Human Nutrition, University of Palermo,
Palermo, Italy. Food Research International (2005), 38(10), 1161-1166. Publisher: Elsevier B.V., CODEN: FORIEU ISSN:
Abstract
Epidemiol. surveys have shown an inverse relationship between the intake of fruit and the incidence of coronary heart disease and
some type of cancer. Data found in the literature regarding the flavonoids in general while this study focuses on flavanones, a
subclass of flavonoids which occurs in Citrus fruit. The aim of this work is to elucidate the antioxidant or pro-oxidant behaviors of
some common flavanones and to det. their activity-structure relationships as antioxidant using the crocin bleaching inhibition assay.
The compds. studied were regarding both the aglycon form and the glycoside form. Data evidence that the substitution of the 7th OH
group of the flavanones by a neohesperidoside influences the relationship between structure and antioxidant activity. In fact, the
3',4'-catechol structure and the O-methylation, in the aglycon forms, do not result significant. On the other hands, in the glycosylate
forms, the 3',4'-catechol structure noticeably increases the antioxidant power and the O-methylation decreases the antioxidant activity.
The influence of the O-glycosylation with a rutinose mol. is neglectable.
Answer 581:
HPLC separation of hesperidin and the C-2 epimer in commercial hesperidin samples and herbal medicines. Uchiyama,
Nahoko; Kim, Ik Hwi; Kawahara, Nobuo; Goda, Yukihiro. National Institute of Health Sciences (NIHS), Tokyo, Japan. Chirality
(2005), 17(7), 373-377. Publisher: Wiley-Liss, Inc., CODEN: CHRLEP ISSN: 0899-0042. Journal written in English. CAN
Abstract
Hesperidin (2S-form), the flavanone 7-O-glycoside, is the main constituent of some Citrus species. The peels of 2 Citrus species are
used as a crude drug, Aurantii nobilis pericarpium, in the Japanese Pharmacopoeia and as components in Kampo formulas. Thus,
HPLC anal. of hesperidin as a marker compd. is needed for quality control of medicines. Hesperidin was sepd. from the corresponding
C-2 epimer by normal-phase HPLC using a chiral column. Moreover, narirutin and neohesperidin were also sepd. from the
corresponding C-2 epimer. The analyses of com. hesperidin samples revealed that they contained the C-2 epimer and that the relative
ratio of hesperidin to the epimer ranged from 92:8 to 59:41. The HPLC application to Citrus exts. suggested that naturally occurring
hesperidin in Citrus has the 2S configuration; however, the dry exts. of rikkunshito and chotosan, which are Kampo formulations contg.
Aurantii nobilis pericarpium, were found to contain a considerable amt. of the (2R)-epimer. These data suggest that the decoction
process of the formulas partly converts hesperidin to the epimer. Because diastereomers differ from each other in physicochem. and
flavanone
biol. activities, HPLC to sep. hesperidin from the C-2 epimer should be introduced into the letter of approval for herbal medicines.
Answer 582:
Chemical diversity of propolis and the problem of standardization. Bankova, Vassya. Institute of Organic Chemistry with
Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulg. Journal of Ethnopharmacology (2005), 100(1-2),
114-117. Publisher: Elsevier Ireland Ltd., CODEN: JOETD7 ISSN: 0378-8741. Journal written in English. CAN 144:376144 AN
Abstract
Chem. variability of propolis is discussed with respect to the problem of standardization. Several chem. types of propolis are
formulated, based on their plant source. Reliable criteria for chem. standardization of different propolis types are needed but such
generally accepted criteria do not yet exist. The chem. profile of "poplar" propolis, typical for the temperate zone, can be characterized
by the following parameters: total flavone and flavonol content, total flavanone and dihydroflavonol content, and total phenolics
content. These parameters correlate better with the biol. activity and are more informative that the quantification of individual
components. There is still a lot of work to be done to achieve standardization of other propolis types. Working with standardized
material will allow scientists to connect a particular chem. propolis type to a specific type of biol. activity and formulate
recommendations for mainstream practitioners.
Answer 583:
Components of Artemisia pontica. Talzhanov, N. A.; Sadyrbekov, D. T.; Smagulova, F. M.; Mukanov, R. M.; Raldugin, V. A.;
Shakirov, M. M.; Tkachev, A. V.; Atazhanova, G. A.; Tuleuov, B. I.; Adekenov, S. M. Institute of Phytochemistry, Ministry of
Education and Science, Karaganda, Kazakhstan. Chemistry of Natural Compounds (2005), 41(2), 178-181. Publisher: Springer
Science+Business Media, Inc., CODEN: CHNCA8 ISSN: 0009-3130. Journal written in English. CAN 144:124962 AN
Abstract
Chem. components from the aerial part of the Kazakhstan population of Artemisia pontica, from which the rarely encountered
flavonoids 7-O-methyl- and 4',7-di-O-Me esters of apigenin were isolated for the first time, were identified. The complete chem.
compn. of the essential oil was established using GC-MS.
Answer 584:
Antioxidant activity of extracts from fruit of Aroeira (Schinus terebenthifolius Raddi). Degaspari, C. H.; Waszczynskyj, N.;
dos Santos, R. J. Aluna do Doulorado em Tecnologia de Alimentos, Universidade Federal do Parana, Brazil. Visao Academica
(2004), 5(2), 83-89. Publisher: Universidade Federal do Parana, Dep. de Farmacia, CODEN: VAICA7 ISSN: 1518-5192. Journal
written in Portuguese. CAN 143:365854 AN 2005:648219 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
flavanone
This work had as objective analyzes the antioxidant activity of aq. and alc. exts. obtained from of the Schinus terebenthifolius Raddi
fruits or aroeira-vermelha, directly linked to the amt. of phenolics compds. existent in these exts. The aroeira fruits present an
intermediate quantity of phenolics compds.: inferior to fruits, however superior to grains, being of 88 g to catequine/g of sample dry
base for the ext. obtained by the extn. in hot water (aq. ext.) and 685 g of catequine/g of sample dry base for the ext. obtained by the
extn. with abs. ethanol (alc. ext.). The alc. ext. was shown with the presence of the flavone apigenin, besides elagic acid, while in the
aq. ext. was obsd. the flavanone naringine. As for its antioxidant power, it can be concluded that the antioxidant powers of both exts.
are good, when it is compared to the antioxidant powers of the commonly used BHT (butylated hydroxytoluene) and BHA (butylated
hydroxyanisole), because it is vegetable exts., whose antioxidant power is, in general, weaker than the artificial antioxidants. In the
case of the alc. ext., the same presented a power antioxidant four times smaller than BHT and BHA. The aq. ext. for its time,
presented a power antioxidant six times smaller than BHT and BHA.
Answer 585:
Metabolic engineering of anthocyanin biosynthesis in Escherichia coli. Yan, Yajun; Chemler, Joseph; Huang, Lixuan;
Martens, Stefan; Koffas, Mattheos A. G. Department of Chemical and Biological Engineering, University at Buffalo, The State
University of New York, Buffalo, NY, USA. Applied and Environmental Microbiology (2005), 71(7), 3617-3623. Publisher:
American Society for Microbiology, CODEN: AEMIDF ISSN: 0099-2240. Journal written in English. CAN 143:284773 AN
Abstract
Anthocyanins are red, purple, or blue plant pigments that belong to the family of polyphenolic compds. collectively called flavonoids.
Their demonstrated antioxidant properties and economic importance to the dye, fruit, and cut-flower industries have driven intensive
research into their metabolic biosynthetic pathways. In order to produce stable, glycosylated anthocyanins from colorless flavanones
such as naringenin and eriodictyol, a four-step metabolic pathway was constructed that contained plant genes from heterologous
origins: flavanone 3β-hydroxylase from Malus domestica, dihydroflavonol 4-reductase from Anthurium andraeanum, anthocyanidin
synthase (ANS) also from M. domestica, and UDP-glucose:flavonoid 3-O-glucosyltransferase from Petunia hybrida. Using two rounds
of PCR, each one of the four genes was first placed under the control of the trc promoter and its own bacterial ribosome-binding site
and then cloned sequentially into vector pK184. Escherichia coli cells contg. the recombinant plant pathway were able to take up either
naringenin or eriodictyol and convert it to the corresponding glycosylated anthocyanin, pelargonidin 3-O-glucoside or cyanidin
3-O-glucoside. The produced anthocyanins were present at low concns., while most of the metabolites detected corresponded to their
dihydroflavonol precursors, as well as the corresponding flavonols. The presence of side product flavonols is at least partly due to an
alternate reaction catalyzed by ANS. This is the first time plant-specific anthocyanins have been produced from a microorganism and
opens up the possibility of further prodn. improvement by protein and pathway engineering.
Answer 586:
Structure activity relationships and quantitative structure activity relationships for the flavonoid-mediated inhibition of
breast cancer resistance protein. Zhang, Shuzhong; Yang, Xinning; Coburn, Robert A.; Morris, Marilyn E. University at Buffalo,
School of Pharmacy and Pharmaceutical Sciences, Department of Pharmaceutical Sciences, State University of New York,
Amherst, NY, USA. Biochemical Pharmacology (2005), 70(4), 627-639. Publisher: Elsevier B.V., CODEN: BCPCA6 ISSN:
Abstract
Breast cancer resistance protein (BCRP) is a newly identified ABC transporter, which plays an important role in drug disposition and
represents an addnl. mechanism for the development of MDR. Flavonoids, a major class of natural compds. widely present in foods
flavanone
and herbal products, have been shown to be BCRP inhibitors. The objective of the present study was to elucidate the SAR and derive
a QSAR model for flavonoid-BCRP interaction. The EC50 values for increasing mitoxantrone accumulation in MCF-7 MX100 cells for
25 flavonoids, from five flavonoid subclasses, were detd. in this study or obtained from our previous publication [Zhang S, Yang X,
Morris ME. Combined effects of multiple flavonoids on breast cancer resistance protein (ABCG2)-mediated transport. Pharm Res
2004;21(7):1263-73], and ranged from 0.07±0.02 μM to 183±21.7 μM. We found that the presence of a 2,3-double bond in ring C, ring
B attached at position 2, hydroxylation at position 5, lack of hydroxylation at position 3 and hydrophobic substitution at positions 6, 7,
8 or 4', are important structural properties important for potent flavonoid-BCRP interaction. These structural requirements are similar
but not identical to those for potent flavonoid-NBD2 (P-glycoprotein) interaction, indicating that inhibition of BCRP by flavonoids may
involve, in part, the binding of flavonoids with the NBD of BCRP. In addn., a QSAR model consisting three structural descriptors was
constructed, and both internally and externally validated, suggesting the model could be used to quant. predict BCRP inhibition activity
of flavonoids. These findings should be useful for predicting BCRP inhibition activity of other untested flavonoids and for guiding the
synthesis of potent BCRP inhibitors for potential clin. application.
Answer 587:
Preparation of gene chips using biotin labelled probes of tea tree flavanone 3-hydroxylase cDNA fragments and uses
thereof. Zhao, Liping; Chen, Liang; Gao, Qikang. (Tea Inst., Chinese Agricultural Academy, Peop. Rep. China). Faming Zhuanli
Shenqing Gongkai Shuomingshu (2004), No pp. given. CODEN: CNXXEV CN 1552899 A 20041208 Patent written in Chinese.
SciFinder (R))

CN 1552899 A 20041208 CN 2003-10109523 20031218
CN 2003-10109523 20031218
Abstract
The present invention relates to prepn. of gene chip using biotin labeled probes of tea tree flavanone 3-hydroxylase cDNA fragments
and uses thereof. Specifically, the invention provides the sequence of tea tree flavanone 3-hydroxylase cDNA, and probes with 8-100
continuous nucleotides of the sequence. The invention can be used in evaluation of crop seed sources, early prediction of hybrid
vigor, research on plant disease resistance, detn. of plant SNP, inspection of transgenic crop security, and screen of herbicides, etc.
Answer 588:
Studies on the synthesis of flavonoids by a two component reaction using microwave heating. Seijas, Julio A.;
Vazquez-Tato, M. Pilar; Carballido-Reboredo, Raquel. Departamento de Quimica Organica, Facultad de Ciencias, Universidad de
Santiago de Compostela, Lugo, Spain. Editor(s): Seijas, Julio A. International Electronic Conferences on Synthetic Organic
Chemistry, 5th, 6th, Sept. 1-30, 2001 and 2002 [and] 7th, 8th, Nov. 1-30, 2003 and 2004 (2004), 1017-1019. Publisher: Molecular
Diversity Preservation International, Basel, Switz CODEN: 69GTCO Conference; Computer Optical Disk written in English. CAN
flavanone
Abstract
Preliminary results on the synthesis of flavanone I without the addn. of a second mol. of aldehyde to the 3 position of the flavanone
by a two component addn.-cyclization approach using microwave heating is reported.
OMe
OH O I
Answer 589:
Catalytic applications of aminopropylated mesoporous silica prepared by a template-free route in flavanones synthesis.
Wang, Xueguang; Tseng, Yao-Hung; Chan, Jerry C. C.; Cheng, Soofin. Department of Chemistry, National Taiwan University,
Taipei, Taiwan. Journal of Catalysis (2005), 233(2), 266-275. Publisher: Elsevier, CODEN: JCTLA5 ISSN: 0021-9517. Journal
Abstract
Aminopropylated silicas are prepd. as catalysts for cyclocondensation reactions of hydroxyacetophenones 5-R-2-HOC6H4COMe and
4-substituted benzaldehydes 4-R1C6H4CHO to yield flavanones I (R = H, Cl, MeO; R1 = H, Cl, MeO, O2N) ; the catalysts are
characterized by N2 sorption, TGA, FTIR, and solid-state NMR measurements. The amt. of aminopropyltriethoxysilane (APTES) used
in the prepn. influences the morphol. of the hybrid org.-inorg. catalysts; the use of ≤ 10 mol% APTES with tetra-Et orthosilicate (TEOS)
and a prehydrolysis step yields mesoporous structures with narrower pore size distributions and larger surface areas and pore vols.
than those prepd. without the TEOS prehydrolysis steps. The fraction of aminopropyl groups present in the catalysts and the width of
the size distribution for the mesopores det. the effectiveness of the aminopropylated silicas as catalysts for cyclocondensation
reactions. The selectivity of the cyclocondensation reactions for flavanones (vs. condensation reactions to give hydroxychalcones)
is highest for solvent-free reactions. Benzaldehydes contg. electron-donating groups are more reactive than benzaldehydes contg.
electron-withdrawing groups in condensations with 2'-hydroxyacetophenones but are less selective for flavanones over
hydroxychalcones, contrary to previous results obtained over solid acid or base catalysts; electron-donating or electron-withdrawing
groups on the hydroxyacetophenones component have little effect on conversions, while selectivities increase slightly when
electron-donating substituents are present on the hydroxyacetophenones. A mechanism for the generation of I over aminopropylated
silica is proposed; the key steps involve the generation of silica-bound imine intermediates.
R1
R
O I
flavanone
Answer 590:
Synthesis of 3-alkenyl-2-arylchromones and 2,3-dialkenylchromones via acid-catalysed retro-Michael ring opening of

3-acylchroman-4-ones. Clarke, David S.; Gabbutt, Christopher D.; Hepworth, John D.; Heron, B. Mark. Department of Colour
and Polymer Chemistry, University of Leeds, Leeds, UK. Tetrahedron Letters (2005), 46(33), 5515-5519. Publisher: Elsevier
B.V., CODEN: TELEAY ISSN: 0040-4039. Journal written in English. CAN 143:286191 AN 2005:614691 CAPLUS (Copyright
Abstract
3-Acylchromones and 3-acylflavones, readily available by acylation of 2'-hydroxydibenzoylmethane with acid anhydrides in the
presence of base, undergo efficient conjugate redn. with NaBH4 in pyridine to give the corresponding chroman-4-ones/flavanones in
high yields. The redn. is both regio- and chemoselective. Treatment of the chroman-4-ones with MeSO3H generates the
3-alkenyl-2-arylchromones by a dehydrative rearrangement initiated by retro-Michael cleavage of the pyranone ring. This
redn.-rearrangement sequence can be extended to 2-alkyl-3-alkenoylchromones to generate 3-alkenyl-2-styrylchromones, the first
examples of 2,3-dialkenylchromones.
Answer 591:
Phytoestrogens as inhibitors of fungal 17β-hydroxysteroid dehydrogenase. Kristan, Katja; Krajnc, Katja; Konc, Janez; Gobec,
Stanislav; Stojan, Jure; Rizner, Tea Lanisnik. Institute of Biochemistry, Medical Faculty, University of Ljubljana, Ljubljana,
Slovenia. Steroids (2005), 70(10), 694-703. Publisher: Elsevier B.V., CODEN: STEDAM ISSN: 0039-128X. Journal written in
Abstract
Different phytoestrogens were tested as inhibitors of 17β-hydroxysteroid dehydrogenase from the fungus Cochliobolus lunatus
(17β-HSDcl), a member of the short-chain dehydrogenase/reductase superfamily. Phytoestrogens inhibited the oxidn. of 100 μM
17β-hydroxyestra-4-en-3-one and the redn. of 100 μM estra-4-en-3,17-dione, the best substrate pair known. The best inhibitors of
oxidn., with IC50 below 1 μM, were flavones hydroxylated at positions 3, 5 and 7: 3-hydroxyflavone, 3,7-dihydroxyflavone,
5,7-dihydroxyflavone (chrysin) and 5-hydroxyflavone, together with 5-methoxyflavone. The best inhibitors of redn. were less potent;
3-hydroxyflavone, 5-methoxyflavone, coumestrol, 3,5,7,4'-tetrahydroxyflavone (kaempferol) and 5-hydroxyflavone all had IC50
values between 1 and 5 μM. Docking the representative inhibitors chrysin and kaempferol into the active site of 17β-HSDcl revealed
the possible binding mode, in which they are sandwiched between the nicotinamide moiety and Tyr212. The structural features of
phytoestrogens, inhibitors of both oxidn. and redn. catalyzed by the fungal 17β-HSD, are similar to the reported structural features of
phytoestrogen inhibitors of human 17β-HSD types 1 and 2.
Answer 592:
The Arabidopsis transcription factor MYB12 is a flavonol-specific regulator of phenylpropanoid biosynthesis. Mehrtens,
Frank; Kranz, Harald; Bednarek, Pawel; Weisshaar, Bernd. Max-Planck-Institute for Plant Breeding Research, Cologne, Germany.
Plant Physiology (2005), 138(2), 1083-1096. Publisher: American Society of Plant Biologists, CODEN: PLPHAY ISSN: 0032-0889.
flavanone
Abstract
Comprehensive functional data on plant R2R3-MYB transcription factors is still scarce compared to the manifold of their occurrence.
Here, we identified the Arabidopsis thaliana R2R3-MYB transcription factor MYB12 as a flavonol-specific activator of flavonoid
biosynthesis. Transient expression in Arabidopsis protoplasts revealed a high degree of functional similarity between MYB12 and the
structurally closely related factor P from maize (Zea mays). Both displayed similar target gene specificity, and both activated target
gene promoters only in the presence of a functional MYB recognition element. The genes encoding the flavonoid biosynthesis
enzymes chalcone synthase, chalcone flavanone isomerase, flavanone 3-hydroxylase, and flavonol synthase were identified as
target genes. Hence, our observations further add to the general notion of a close relationship between structure and function of
R2R3-MYB factors. High-performance liq. chromatog. analyses of myb12 mutant plants and MYB12 overexpression plants
demonstrate a tight linkage between the expression level of functional MYB12 and the flavonol content of young seedlings. Quant.
real time reverse transcription-PCR using these mutant plants showed MYB12 to be a transcriptional regulator of CHALCONE
SYNTHASE and FLAVONOL SYNTHASE in planta, the gene products of which are indispensable for the biosynthesis of flavonols.
Answer 593:
Antihyperglycaemic flavonoids from syzygium samarangense (Blume) Merr. and Perry. Resurreccion-Magno, Ma. Hanshella
C.; Villasenor, Irene M.; Harada, Nobuyuki; Monde, Kenji. Institute of Chemistry, University of the Philippines, Quezon City,
Philippines. Phytotherapy Research (2005), 19(3), 246-253. Publisher: John Wiley & Sons Ltd., CODEN: PHYREH ISSN:
Abstract
2',4'-Dihydroxy-3',5'-dimethyl-6'-methoxychalcone (1), its isomeric flavanone 5-O-methyl-4'-desmethoxymatteucinol (2) and

2'4'-dihydroxy-6'-methoxy-3'-methylchalcone (3) were isolated from the leaves of S. samarangense using a bioassay-directed scheme.
In an oral glucose tolerance test, at a dosage of 1.0 mg/20 g mouse, 1 and 2 significantly (α = 0.05) lowered the blood glucose levels
(BGLs) in glucose-hyperglycemic mice when administered 15 min after a glucose load. When co-administered with glucose, only 1
showed a significant lowering of BGLs 45 min after its oral administration. When administered 15 min before glucose, none of the
flavonoids showed a pos. effect. Only 1 decreased significantly, at α = 0.05, the BGLs of alloxan-diabetic mice at t = 90-150 min.
Answer 594:
Lipophilic C-methylflavonoids with no B-ring oxygenation in Metrosideros species (Myrtaceae). Mustafa, Kamarul'Ain;
Perry, Nigel B.; Weavers, Rex T. Department of Chemistry, University of Otago, Dunedin, N. Z. Biochemical Systematics and
Ecology (2005), 33(10), 1049-1059. Publisher: Elsevier B.V., CODEN: BSECBU ISSN: 0305-1978. Journal written in English.
Abstract
Five unusual C-methylflavonoids lacking B-ring oxygenation (2',4'-dihydroxy-3',5'-dimethyl-6'-methoxychalcone,

2',4'-dihydroxy-3'-methyl-6'-methoxychalcone, 2',6'-dihydroxy-3'-methyl-4'-methoxychalcone,
2'-hydroxy-3'-methyl-4',6'-dimethoxychalcone and 5,7-dihydroxy-6,8-dimethylflavanone) were found for the first time in Metrosideros
excelsa. The flavanone was the major constituent in leaves, whereas 2',6'-dihydroxy-3'-methyl-4'-methoxychalcone dominated all
other aerial plant parts studied. Other Metrosideros species were investigated for these five flavonoids. C19-C36 aldehydes and
C22-C32 alcs. were also identified from the dried seed capsules of M. excelsa.
flavanone
Answer 595:
Isolation and purification of closely related Citrus limonoid glucosides by flash chromatography. Raman, Girija; Cho,
Minhee; Brodbelt, Jennifer S.; Patil, Bhimanagouda S. Kingsville Citrus Center, Texas A and M University, Weslaco, TX, USA.
Phytochemical Analysis (2005), 16(3), 155-160. Publisher: John Wiley & Sons Ltd., CODEN: PHANEL ISSN: 0958-0344. Journal
Abstract
Several citrus limonoid glycosides have proved to be particularly difficult to purify using conventional techniques. A reversed-phase
flash chromatog. technique was developed for the sepn. and isolation of the closely related limonoid glucosides, nomilin
17-β-D-glucopyranoside and nomilinic acid 17-β-D-glucopyranoside, with confirmation of their identities by electrospray ionization mass
spectrometry. Furthermore, the semi-purifn. of the mixt. of glucosides enriched with flavanone glucosides such as naringin, narirutin
and other limonoid glucosides was obtained. The closely eluting glucosides were successfully sepd. to achieve a good yield and purity
of 93%.
Answer 596:
Evaluation of cyclodextrins modified with dichloro-, dimethyl-, and chloromethylphenylcarbamate groups as chiral
stationary phases for capillary electrochromatography. Kartozia, Irma; D'Orazio, Giovanni; Chankvetadze, Bezhan; Fanali,
Salvatore. Instituto di Metodologie Chimiche, Consiglio Nazionale delle Ricerche, Area della Ricerca di Roma, Rome, Italy.
Journal of Capillary Electrophoresis and Microchip Technology (2005), 9(3/4), 31-38. Publisher: ISC Technical Publications, Inc.,
CODEN: JCEMF6 Journal written in English. CAN 144:266139 AN 2005:590801 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
Capillary electrochromatog. using cyclodextrins modified with dichloro-, dimethyl-, and chloromethylcarbamate groups were used for
the enantiomeric sepn. of std. analytes. The chiral selector was chem. bonded to aminopropylsilanized silica particles, and these chiral
stationary phases (CSPs), mixed with aminopropylsilanized silica (1:1 wt.:wt.), were packed into 100-μm-internal diam. fused-silica
capillaries. The effect of the type of cyclodextrin, the nature and position of the substituents on the Ph ring, and the binding mode of
cyclodextrin phenyl-carbamates onto the silica gel surface on the chiral recognition were studied. Exptl. parameters such as org.
solvent concn. were varied to better understand the mechanism contributing to the chiral recognition of these CSPs. Good
enantiosepns. were achieved for a racemic flavanone (FLA) and trans-cyclopropanedicarboxylic acid dianilide (CAD).
Answer 597:
Radical scavenging activity of various extracts and fractions of sweet orange peel (Citrus sinensis). Anagnostopoulou, Maria
A.; Kefalas, Panagiotis; Papageorgiou, Vassilios P.; Assimopoulou, Andreana N.; Boskou, Dimitrios. Department of Chemical
Engineering, Faculty of Engineering, Aristotle University of Thessaloniki, Thessaloniki, Greece. Food Chemistry (2005), Volume
Date 2006, 94(1), 19-25. Publisher: Elsevier B.V., CODEN: FOCHDJ ISSN: 0308-8146. Journal written in English. CAN
Abstract
flavanone
Seven different exts., fractions and residues of Navel sweet orange (Citrus sinensis) peel were evaluated for their radical scavenging
activity by the DPPH⋅ and luminol induced chemiluminescence methods. Also, the Folin-Ciocalteu method was used to det. the total
phenolic content. High phenolic content and radical scavenging activities were found for the Et acetate fraction. Comparison was
made with ref. compds., Trolox, ascorbic acid, quercetin, which are already known for their good antioxidant activity. The radical
scavenging activity of the Et acetate fraction approached the activity of the stds. Total phenolic content showed a small relation with
radical scavenging activity. The radical scavenging activity examd. with the DPPH method correlated well to values obtained by
chemiluminescence. The antioxidant activity found in the fractions of Citrus sinensis, should be attributed to the presence of
flavonoids and other phenolic compds. Among the various classes of flavonoids: flavanone glycosides, flavones and flavonols seem
to prevail as indicated by two dimensional thin layer chromatog. and color reactions. This information shows that Et acetate fraction of
navel sweet orange peel can be used as antioxidant in food and medicinal prepns.
Answer 598:
Nucleic acids and encoded enzymes active in lignin, fructan and tannin biosynthesis from forage grasses. Demmer,
Jeroen; Forster, Richard L.; Shenk, Michael Andrew; Norriss, Michael Geoffrey; Glenn, Matthew; Saulsbury, Keith Martin; Hall, Claire.
(Agrigenesis Biosciences Ltd., N. Z.; Wrightson Seeds Ltd.). U.S. Pat. Appl. Publ. (2005), 38 pp., Cont.-in-part of U.S. Ser. No.
289,757. CODEN: USXXCO US 2005150008 A1 20050707 Patent written in English. Application: US 2004-955745 20040930.
Priority: US 2001-337703 20011107; US 2002-289757 20021107; US 2003-507991 20031002; US 2004-563879 20040420. CAN

US 20050150008 A1 20050707 US 2004-955745 20040930
US 20030180751 A1 20030925 US 2002-289757 20021107
US 7154027 B2 20061226
US 20070204363 A1 20070830 US 2006-560738 20061116
US 2001-337703P P 20011107
US 2002-289757 A2 20021107
US 2003-507991P P 20031002
US 2004-563879P P 20040420
Abstract
Polynucleotides encoding polypeptides active in lignin, fructan and tannin biosynthetic pathways are provided from Lolium perenne
(perennial ryegrass) and Festuca arundinaceae (tall fescue), together with expression vectors and host cells comprising such isolated
polynucleotides. The polynucleotides were taken at different times of the year, specifically in winter and spring, and from different
parts of the the plants, including leaf blades, leaf base, pseudostems, floral stems, roots, inflorescences, and stems. Methods for the
use of such polynucleotides and polypeptides are also provided.
Answer 599:
flavanone
Preparative monohydroxyflavanone syntheses and a protocol for gas chromatography-mass spectrometry analysis of
monohydroxyflavanones. Kagawa, Hitoshi; Shigematsu, Asako; Ohta, Shigeru; Harigaya, Yoshihiro. Department of Organic
Synthesis, School of Pharmaceutical Sciences, Kitasato University, Tokyo, Japan. Chemical & Pharmaceutical Bulletin (2005),
53(5), 547-554. Publisher: Pharmaceutical Society of Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN
Abstract
A facile efficient, and preparative approach for monohydroxyflavanone syntheses was described. Using this protocol, a hydroxyl is
regio-selectively introduced at one carbon of a flavanone A- or B-ring per synthesis. The seven possible isomers were each
synthesized from the corresponding monomethoxymethoxylated 2'-hydroxychalcones in acidic soln. These monohydroxyflavanones
were characterized using a gas chromatog.-mass spectrometry (GC-MS) system that incorporated a DB-5 capillary column. This is the
first report of a preparative synthetic method during which a single hydroxyl can be selectively added to a flavanone A- or B-ring at
any position. A procedure that separates the seven isomers by GC and characterizes the mass spectra of the isomers was
developed. Both the synthetic method and the GC-MS conditions may become important tools during future flavanone metab. and
oxidn. studies.
Answer 600:
Cloning and characterization of a flavanone 3-hydroxylase gene from Saussurea medusa. Jin, Zhiping; Grotewold, Erich; Qu,
Wenquan; Fu, Ghunxiang; Zhao, Dexiu. Institute of Botany, Chinese Academy of Sciences, Beijing, Peop. Rep. China. DNA
Sequence (2005), 16(2), 121-129. Publisher: Taylor & Francis Ltd., CODEN: DNSEES ISSN: 1042-5179. Journal written in
Abstract
Flavanone 3-hydroxylase (F3H) is a key enzyme in the flavonoid biosynthetic pathway, providing a branching point for the
biosynthesis of different flavonoids, including the formation of 3-deoxy and 3-hydroxy flavonoids found in the silks of maize. Here,
we report the cloning and characterization of a F3H gene (Smf3h) from a cDNA library derived from a red line callus of Saussurea
medusa, a traditional Chinese medicinal plant. The cDNA contains a 1032 bp open reading frame (ORF) encoding a protein of 343
amino acid residues, a 149 bp long 5'untranslated regions (UTR) and a 163 bp long 3'UTR contg. three putative polyadenylation signals
(AATAAA) and an ATTTA element. The secondary structure of the mRNA predicted by MFOLD is very complex, suggesting a role in a
post-transcriptional mechanism of regulation of Smf3h. The genomic structure of Smf3h includes four exons and three introns within
the coding region, with all the splice donor/acceptor site sequences in accordance with the "GU-AG" consensus rule. The deduced
SmF3H protein is 343 amino acid residues in length and has 40% and 39% identity and 60% and 58% similarity to the F3H of
Arabidopsis and rice, resp. Strikingly, the identity of SmF3H is higher to the H6H (hyoscyamine 3β-hydroxylase, 45%) from Atropa
belladonna. However, the anal. of the active center and the predicted protein secondary structure are more related to F3H than H6H.
Together, our studies provide the first identification of a S. medusa flavonoid gene and its similarities to metabolic enzymes from other
plants.
Answer 601:
Method of breeding plants with yellow flowers by regulating flavonoid biosynthesis system. Tanaka, Yoshikazu; Ono,
Eiichiro; Nakamura, Noriko; Mizutani, Masako. (Suntory Limited, Japan; Suntory Flowers Limited). PCT Int. Appl. (2005), 95 pp.
KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU,
flavanone
SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE,
CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG.
Patent written in Japanese. Application: WO 2004-JP19461 20041217. Priority: JP 2003-420046 20031217. CAN 143:92063 AN

WO 2005059141 A1 20050630 WO 2004-JP19461 20041217
ZW
AU 2004299755 A1 20050630 AU 2004-299755 20041217
CA 2550507 A1 20050630 CA 2004-2550507 20041217
EP 1702987 A1 20060920 EP 2004-807816 20041217
R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT, IE, SI, LT, FI, RO, CY, TR, BG, CZ,
EE, HU, PL, SK, IS
US 20080009032 A1 20080110 US 2006-583110 20060615
JP 2003-420046 A 20031217
WO 2004-JP19461 W 20041217
Abstract
A method of breeding the plants with yellow flowers by regulating flavonoid biosynthesis system has been developed. The regulation
process includes the introduction of the vector contg. the transgene encoding the enzyme that transfers sugars to 4'-position of
chalcones into host plant cells. The glycosyltransferase genes are cloned from Antirrhinum majus or Linaria bipartita in
Scrophulariaceae. The transformant cells, the purifn. method of the expressed transferase, whole transgenic plants and their tissues,
descendants and cut flowers are claimed. The process also includes the co-expressing of the gene for aureusidin synthase and
dsRNA-induced silencing of the genes for dihydroflavonol reductase and/or flavanone 3-hydroxlase to promote the coloring the flowers
in yellow. By the claimed method to manipulate the flavonoid biosynthesis system, a transgenic plant with flowers in an improved
vivid yellow color can be obtained. Flower color change by the claimed method was tested in Torenia fournieri.
Answer 602:
Chemical shifts of 1H and 13C in 5-H-flavanone and 5-H-flavonol isolated from Leguminosae. Alves do Nascimento, Ildomar;
Gomes, Mario Sergio da Rocha; Geraldo de Carvalho, Mario; Geraldo de Carvalho, Acacio. Doutorando do PPGQO do Departmento
de Quimica, Instituto de Ciencias Exatas, Universidade Federal Rural do Rio de Janeiro, Seropedica, Rio de Janeiro, Brazil.
Revista Universidade Rural, Serie Ciencias Exatas e da Terra (2003), 22(1-2), 81-87. Publisher: Editora da Universidade Federal
Rural do Rio de Janeiro, CODEN: RURSAQ ISSN: 1414-0578. Journal written in Portuguese. CAN 144:229262 AN 2005:551356
flavanone
Abstract
Unambiguous 1H and 13C chem. shift assignments in NMR spectra of 3,4',7-trihydroxyflavonone (garbanzol) isolated from
Schizolobium parahyba and 3',4',7,8-tetrahydroxyflavanone isolated from Piptadenia rigida were studied using 1D and 2D NMR
spectroscopic techniques.
Answer 603:
Flavonoids from the Stem of Eriophorum scheuchzeri. Maver, Milena; Queiroz, Emerson F.; Wolfender, Jean-Luc;
Hostettmann, Kurt. Laboratoire de Pharmacognosie et Phytochimie, Section de Sciences Pharmaceutiques, University of Geneva,
Geneva, Switz. Journal of Natural Products (2005), 68(7), 1094-1098. Publisher: American Chemical Society, CODEN: JNPRDF
SciFinder (R))
Abstract
Activity-guided isolation of antifungal, antibacterial, and antioxidant compds. from the dichloromethane ext. of the aerial parts of
Eriophorum scheuchzeri led to the isolation of eight flavonoids. Three isoflavones and one flavanone are new natural compds. The
isolation of the bioactive compds. was performed by centrifugal partition chromatog. Fractions and pure compds. were monitored by a
direct TLC bioautog. assay. Their structures were elucidated by spectroscopic and chem. methods.
Answer 604:
Evaluation of Bitter Masking Flavanones from Herba Santa (Eriodictyon californicum (H. & A.) Torr., Hydrophyllaceae).
Ley, Jakob P.; Krammer, Gerhard; Reinders, Gerald; Gatfield, Ian L.; Bertram, Heinz-Juergen. Research and Development, Symrise
GmbH & Company KG, Holzminden, Germany. Journal of Agricultural and Food Chemistry (2005), 53(15), 6061-6066. Publisher:
American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 143:210692 AN 2005:535269
Abstract
Products made from Herba Santa (Eriodictyon californicum (H. & A.) Torr.) have been used as bitter remedies for some
pharmaceutical applications for many years, but they are actually too arom. to be useful for many food or pharmaceutical
applications. In sensory studies flavanones homoeriodictyol (1), its sodium salt (1-Na), sterubin (2), and eriodictyol (4) could
significantly decrease the bitter taste of caffeine without exhibiting intrinsic strong flavors or taste characteristics. Further
investigations on 1-Na elicited a broad masking activity between 10 and 40% toward different chem. classes of bitter mols. (e.g.
salicin, amarogentin, paracetamol, quinine) but not toward bitter linoleic acid emulsions. For caffeine and amarogentin, dose-response
studies were performed; the masking activity toward bitter taste for both compds. reached a plateau at higher concns. of 1-Na. Due to
these facts, homoeriodictyol sodium salt (1-Na) seems to be a very interesting new taste modifier for food applications and
pharmaceuticals.
Answer 605:
flavanone
Novel, complex flavonoids from Mallotus philippensis (Kamala tree). Furusawa, Miyuki; Ido, Yoshimi; Tanaka, Toshiyuki; Ito,
Tetsuro; Nakaya, Ken-ichi; Ibrahim, Iliya; Ohyama, Masayoshi; Iinuma, Munekazu; Shirataka, Yoshiaki; Takahashi, Yoshikazu. Gifu
Prefectural Institute of Health and Environmental Sciences, Kakamigahara, Japan. Helvetica Chimica Acta (2005), 88(5),
1048-1058. Publisher: Verlag Helvetica Chimica Acta, CODEN: HCACAV ISSN: 0018-019X. Journal written in English. CAN
Abstract
One new flavanone, 4'-hydroxyisorottlerin (I), and two new chalcone derivs., kamalachalcones C (II) and D (III), were isolated from
Mallotus philippensis (kamala tree). The largest compd. (kamalachalcone D; Mr 1098 g/mol) was shown to possess a unique, fused-ring
system made of two hydroxy-chalcone units, giving rise to eight fused benzene/pyran units. From the same plant, the following six
known compds. were also isolated: kamalachalcone A and B, isoallorottlerin, isorottlerin, 5,7-dihydroxy-8-methyl-6-prenylflavanone,
6,6-dimethylpyrano(2'',3'':7,6)-5-hydroxy-8-methylflavanone, and rottlerin. The structures of the new compds. were confirmed by
in-depth spectral analyses, including 2D-NMR techniques, and the full 13C-NMR assignments of rottlerin, isoallorottlerin, isorottlerin,
5,7-dihydroxy-8-methyl-6-prenylflavanone, and 6,6-dimethylpyrano(2'',3'':7,6)-5-hydroxy-8-methylflavanone are published for the first
time.
flavanone
Me O
HO OH
Me OH
Me HO
O O
Me
OH O I
Me
HO O
Me
H
Me
H
OH O OH
Me
Me
OH O II
Me Me
O Me Me
O O Me Me
HO O O
O OH
HO O O
Me
O Me HO OH
HO OH
Me
Me III
flavanone
Answer 606:
Molecular evolution of flavonoid dioxygenases in the family Apiaceae. Gebhardt, Yvonne; Witte, Simone; Forkmann, Gert;
Lukacin, Richard; Matern, Ulrich; Martens, Stefan. Institut fuer Pharmazeutische Biologie, Philipps Universitaet Marburg,
Marburg/Lahn, Germany. Phytochemistry (Elsevier) (2005), 66(11), 1273-1284. Publisher: Elsevier B.V., CODEN: PYTCAS
SciFinder (R))
Abstract
Plant species of the family Apiaceae are known to accumulate flavonoids mainly in the form of flavones and flavonols. Three
2-oxoglutarate-dependent dioxygenases, flavone synthase or flavanone 3 β-hydroxylase and flavonol synthase are involved in the
biosynthesis of these secondary metabolites. The corresponding genes were cloned recently from parsley (Petroselinum crispum)
leaves. Flavone synthase I appears to be confined to the Apiaceae, and the unique occurrence as well as its high sequence similarity
to flavanone 3β-hydroxylase laid the basis for evolutionary studies. In order to examine the relationship of these two enzymes
throughout the Apiaceae, RT-PCR based cloning and functional identification of flavone synthases I or flavanone 3β-hydroxylases
were accomplished from Ammi majus, Anethum graveolens, Apium graveolens, Pimpinella anisum, Conium maculatum and Daucus
carota, yielding three addnl. synthase and three addnl. hydroxylase cDNAs. Mol. and phylogenetic analyses of these sequences were
compatible with the phylogeny based on morphol. characteristics and suggested that flavone synthase I most likely resulted from
gene duplication of flavanone 3β-hydroxylase, and functional diversification at some point during the development of the apiaceae
subfamilies. Furthermore, the genomic sequences from Petroselinum crispum and Daucus carota revealed two introns in each of the
synthases and a lack of introns in the hydroxylases. These results might be explained by intron losses from the hydroxylases
occurring at a later stage of evolution.
Answer 607:
Glucuronidation of bioflavonoids by human UGT1A10: Structure-function relationships. Lewinsky, R. H.; Smith, P. A.;
Mackenzie, P. I. Department of Clinical Pharmacology, Flinders Medical Centre, Flinders University School of Medicine, Bedford
Park, Australia. Xenobiotica (2005), 35(2), 117-129. Publisher: Taylor & Francis Ltd., CODEN: XENOBH ISSN: 0049-8254.
Abstract
The extrahepatic human UDP glucuronosyltransferase 1A10 is found throughout the gastrointestinal tract and is thought to participate
in the removal of orally ingested lipophilic chems. However, its substrate specificity towards these chems. has not been fully
characterized. The structurally diverse bioflavonoids are present in considerable amts. in fruits, vegetables and plant-derived
beverages and have been shown to have many biol. functions, including antioxidant properties. This study proposes features of the
bioflavonoid structure necessary to confer it as a substrate of UGT1A10. The preferred substrates of UGT1A10 contain the hydroxyl
group to be glucuronidated at C6 or C7, but not C5 of the A-ring or on C4' of the B-ring. Up to two addnl. hydroxyl groups on the A-ring
enhance activity, whereas the presence of other groups, notably sugar groups, decreases activity. The high glucuronidation efficiency
towards many bioflavonoids obsd. suggests that the contribution of UGT1A10 in the metab. of these dietary compds. in the
gastrointestinal tract may be significant.
Answer 608:
flavanone
Solvent free synthesis of chalcone and flavanone over zinc oxide supported metal oxide catalysts. Saravanamurugan, S.;
Palanichamy, M.; Arabindoo, Banumathi; Murugesan, V. Department of Chemistry, Anna University, Chennai, India. Catalysis
Communications (2005), 6(6), 399-403. Publisher: Elsevier B.V., CODEN: CCAOAC ISSN: 1566-7367. Journal written in English.
Abstract
Liq. phase Claisen-Schmidt condensation between 2'-hydroxyacetophenone and benzaldehyde to form 2'-hydroxychalcone, followed by
intramol. cyclization to form flavanone was carried out over zinc oxide-supported metal oxide catalysts under solvent free condition.
The reaction was carried out over ZnO-supported MgO, BaO, K2O and Na2O catalysts with 0.2 g of each catalyst at 140° for 3 h.
ZnO-supported MgO was obsd. to offer highest conversion of 2'-hydroxyacetophenone than other catalysts. Other supports, such as
HZSM-5, Al2O3 and SiO2, impregnated with MgO were also used for the reaction to assess the suitability of the support. The order of
activity of the catalyst support is ZnO > SiO2 > Al2O3 > HZSM-5. Various wt. percentage of MgO was loaded on ZnO to optimize max.
efficiency of the catalyst system. The impregnation of MgO (wt%) in ZnO was optimized for better conversion of
2'-hydroxyacetophenone. The effect of temp. and catalyst loading was studied for the reaction.
Answer 609:
Interaction between hesperetin and human serum albumin revealed by spectroscopic methods. Xie, Meng-Xia; Xu, Xiao-Yun;
Wang, Ying-Dian. Analytical & Testing Center, Beijing Normal University, Beijing, Peop. Rep. China. Biochimica et Biophysica
Acta, General Subjects (2005), 1724(1-2), 215-224. Publisher: Elsevier B.V., CODEN: BBGSB3 ISSN: 0304-4165. Journal written
Abstract
Hesperetin (5,7,3'-trihydroxyl-4'-methoxyl-flavanone) is an important bioactive compd. in Chinese traditional medicine and has multiple
biol. and pharmacol. activities. The interaction of hesperetin with human serum albumin (HSA) has been investigated by UV
absorption, fluorescence and Fourier transformed IR spectrometry. Fluorescence results showed that one mol. of protein combined
with one mol. of drug at the molar ratio of drug to HSA ranging from 0.3 to 7 and the binding affinity (KA) was 8.11×104 M-1. The
primary binding site was most likely located on subdomain IIA. The binding ability of the drug to protein decreased from pH 6.4 to 8.4
in the drug to protein molar ratio of 1. Combining the curve-fitting results of IR amide I band in D2O and H2O phosphate buffers, the
alterations of protein secondary structure after drug complexation were estd. With increasing the drug concn., the percentage of
protein α-helix structure decreased gradually. The redn. of protein α-helix structure reached about 7-9% after the protein interacted with
hesperetin in D2O and H2O buffer soln. at pH 7.4 when the drug to protein molar ratio was 10. This indicated a partial unfolding of
HSA in the presence of the drug. From the results of UV absorption, fluorescence and Fourier transformed IR spectrometry, the
binding mode was discussed. The main mechanism of protein fluorescence quenching was a static quenching process and the
hydroxyl groups of the drug in its neutral part played an important role in the binding process.
Answer 610:
Analysis of flavanone-7-O-glycosides in citrus juices by short-end capillary electrochromatography. Desiderio, Claudia; De

Rossi, Antonella; Sinibaldi, Massimo. Istituto di Metodologie Chimiche, CNR, Rome, Italy. Journal of Chromatography, A
(2005), 1081(1), 99-104. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. CAN
Abstract
flavanone
The sepn. of the major flavanone-7-O-glycoside constituents of Citrus was carried out by isocratic reversed phase capillary
electrochromatog. using a 75 μm i.d. silica fused column packed with 5 μm ODS silica gel. In comparison to HPLC mode, capillary
electrochromatog. resoln. of flavanone glycosides was obtained with a high selectivity factor. Optimum sepn. conditions were found
using a mixt. of ammonium formate (pH 2.5)-acetonitrile (8:2, vol./vol.) as the mobile phase by the short-end injection mode. Under
these conditions all the investigated flavanones were baseline-resolved within short anal. time (i.e. between 5 and 10 min). A study,
evaluating the intra- and inter-day repeatability as well as limit of detection and method linearity, was developed in accordance with the
anal. procedures for method validation. The developed method was applied for the quant. anal. of flavanone glycosides in com. fruit
juices (sweet orange, lemon and grapefruit).
Answer 611:
Studies on the constituents of Hypericum species. I. on the chemical constituents of Hypericum erectum Thunb.
Matsuoka, Erika; Machida, Koichi; Kikuchi, Masao. Fac. Pharm. Sci., Tohoku Pharm. Univ., Japan. Journal of Tohoku
Pharmaceutical University (2004), 51 41-48. Publisher: Tohoku Yakka Daigaku, CODEN: JTPUFY ISSN: 1345-157X. Journal
written in Japanese. CAN 143:189890 AN 2005:503827 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
Eleven constituents, 7-hydroxy-2,5-dimethylchromone (1), (-)-farrerol (2), (±)-4-hydroxy-4,7-dimethyl-α-tetralone (3), six ferulic acid
esters (4-9), eudesm-4 (15)-ene-1β,6α-diol (10) and opposit-4(15)-ene-1β,11-diol (11) were isolated from Hypericum erectum Thunb.
Their structures were established on the basis of spectral data. In addn., (±)-3 was sepd. into its enantiomers [(+)-3, (-)-3], and the abs.
configurations at C-4 of (+)-3 and (-)-3 were assigned as S and R, resp., from the CD (CD) spectral data.
Answer 612:
Production of cytokine and NO by RAW 264.7 macrophages and PBMC in vitro incubation with flavonoids. Lyu, Su-Yun;
Park, Won-Bong. Immune Modulation Research Laboratory, School of Pharmacy, University of Nottingham, Nottingham, UK.
Archives of Pharmacal Research (2005), 28(5), 573-581. Publisher: Pharmaceutical Society of Korea, CODEN: APHRDQ ISSN:
Abstract
Flavonoids, a group of low mol. wt. phenylbenzopyrones, have various pharmacol. properties including antioxidant activity, anticancer,
and immunomodulatory effects. In the present study, lipopolysaccharide (LPS) and phorbol 12-myristate
13-acetate/phytohemagglutinin (PMA/PHA) were used as stimulants for RAW 264.7 macrophages and human peripheral blood
mononuclear cell (hPBMC), and tumor necrosis factor (TNF)-α and interleukin (IL)-2 productions were measured. In addn., flavonoids
were examd. for their effects on LPS-induced NO prodn. in RAW 264.7 macrophages. The results showed that all compds. were not
strongly cytotoxic at the tested concns. on hPBMC and RAW 264.7 macrophages. On immunomodulatory properties, catechin,
epigallocatechin (EGC), naringenin, and fisetin repressed NO prodn. and TNF-α secretion. Furthermore, catechin, epigallocatechin
gallate (EGCG), epicatechin (EC), luteolin, chrysin, quercetin, and galangin increased IL-2 secretion while EGC, apigenin, and fisetin
inhibited the secretion. These results indicated that flavonoids have the capacity to modulate the immune response and have a
potential anti-inflammatory activity. There was no obvious structure-activity relationship regard to the chem. compn. of the flavonoids
and their cell biol. effects.
Answer 613:
flavanone
In vitro free radical and ONOO- scavengers from Sophora flavescens. Jung, Hee Jin; Kang, San Sik; Hyun, Sook Kyung; Choi,
Jae Sue. Faculty of Food Science and Biotechnology, Pukyong National University, Pusan, S. Korea. Archives of Pharmacal
Research (2005), 28(5), 534-540. Publisher: Pharmaceutical Society of Korea, CODEN: APHRDQ ISSN: 0253-6269. Journal
Abstract
Activity-guided fractionation of the CH2Cl2-sol. fraction of the roots of Sophora flavescens furnished five
1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavengers: trans-hexadecyl ferulic acid (1), cis-octadecyl ferulic acid (2),
trans-hexadecyl sinapic acid (3), (-)-4-hydroxy-3-methoxy-(6aR,11aR)-8,9-methylenedioxypterocarpan (4) and
desmethylanhydroicaritin (8), along with nine known inactive compds.: (-)-maackiain (5), xanthohumol (6), formononetin (7),
(2S)-2'-methoxykurarinone (9), (2S)-3β,7,4'-trihydroxy-5-methoxy-8-(γ,γ-dimethylallyl)-flavanone (10),
(2S)-7,4'-dihydroxy-5-methoxy-8-(γ,γ-dimethylallyl)-flavanone (11), umbelliferone (12), kuraridin (13), and trifolirhizin (14). Compds. 1-4
and 8 exhibited DPPH free radical scavenging effects at IC50 values of 33.01 ± 0.20, 57.06 ± 0.16, 39.84 ± 0.36, 35.83 ± 0.47, and
18.11 ± 0.04 μM, resp. L-Ascorbic acid, when used as a pos. control, exhibited an IC50 value of 7.39 ± 0.01 μM. Compds. 1-4 and 8
also appeared to exert significant scavenging effects on authentic ONOO-, with IC50 values of 5.76 ± 1.19, 15.06 ± 1.64, 8.17 ± 4.97,
1.95 ± 0.29, and 4.06 ± 2.41 μM, resp. Penicillamine (IC50 = 2.36 ± 0.79 μM) was used as a pos. control. In addn., compds. 2, 4, 6,
8, and 10 were isolated from this plant for the first time.
Answer 614:
Facile oxidation of flavanones to flavones using [hydroxy(tosyloxy)iodo]benzene in an ionic liquid. Muthukrishnan,

Murugan; Patil, Pratap S.; More, Shivaji V.; Joshi, Ramesh A. Division of Organic Chemistry: Technology, National Chemical
Laboratory, Pune, India. Mendeleev Communications (2005), (3), 100-101. Publisher: Russian Academy of Sciences, CODEN:
MENCEX ISSN: 0959-9436. Journal written in English. CAN 144:150151 AN 2005:494772 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
A method for the oxidn. of flavanones to flavones was developed using [hydroxy(tosyloxy)iodo]benzene in the room-temp. ionic liq.
1,3-di-n-butylimidazolium bromide.
Answer 615:
Bioavailability and antioxidant effects of orange juice components in humans. Franke, Adrian A.; Cooney, Robert V.;
Henning, Susanne M.; Custer, Laurie J. Cancer Research Center of Hawaii, University of Hawaii, Honolulu, HI, USA. Journal of
Abstract
Seven healthy women and six men consumed daily 256 mg vitamin C, 229 mg hesperidin (main flavonoid glycoside), 6 mg
carotenoids (mainly luteins and cryptoxanthins), and 0.16 mg folate incorporated in 236 mL of not-from-conc. orange juice (OJ) added
flavanone
to their habitual diet. At the end of 3 wk, mean vitamin C, folate, carotenoid, and flavanone blood plasma concns. were increased
relative to baseline by 59%, 46%, 22%, and 8-fold, resp. Flavanones were excreted in urine 9-fold more at the end of the 3-wk
intervention, but returned to baseline 2 days after study completion. After the 3-wk intervention, blood plasma concns. of vitamins A
and E did not change. White blood cell 8-hydroxydeoxyguanosine levels declined by 16% (n = 11) and in individuals with high baseline
concns. by 29% (n = 7). The low-d. lipoprotein/high-d. lipoprotein (LDL/HDL) cholesterol ratios decreased, but cholesterol (HDL, LDL,
total) and thiobarbituric acid-reactive substance plasma concns. did not much change. Thus, OJ is an excellent food source to
enhance circulating concns. of valuable hydrophilic and lipophilic phytochems.
Answer 616:
High-performance liquid chromatographic separation and chiroptical properties of the enantiomers of naringenin and other
flavanones. Caccamese, Salvatore; Caruso, Carmelo; Parrinello, Nunziatina; Savarino, Anna. Dipartimento di Scienze Chimiche,
Universita di Catania, Catania, Italy. Journal of Chromatography, A (2005), 1076(1-2), 155-162. Publisher: Elsevier B.V.,
CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. CAN 143:165631 AN 2005:427245 CAPLUS (Copyright (C)
Abstract
The HPLC enantiomeric sepn. of naringenin, eriodictyol, hesperetin and pinocembrin was accomplished in the normal-phase mode using
two polysaccharide-derived chiral stationary phases (Chiralcel OD-H and Chiralpak AS-H) and various n-hexane/alc. mobile phases.
The 3',4' substituents pattern affect the enantioselectivity of these phases. Single enantiomers of naringenin were isolated by
semipreparative HPLC and their CD spectra were measured and related to the abs. configuration by the exciton-coupling method.
Online coupling HPLC/spectropolarimeter afforded the CD sign of the eluted peaks at a single wavelength, and the complete CD
spectra of the eluted enantiomers were obtained by trapping them in the spectropolarimeter cell through a switching valve.
Answer 617:
Decreased anthocyanin biosynthesis in grape berries grown under elevated night temperature condition. Mori, Kentaro;
Sugaya, Sumiko; Gemma, Hiroshi. Doctoral Program in Agricultural Sciences, University of Tsukuba, Ibaraki, Japan. Scientia
Horticulturae (Amsterdam, Netherlands) (2005), 105(3), 319-330. Publisher: Elsevier B.V., CODEN: SHRTAH ISSN: 0304-4238.
Abstract
In grape cultivation, high night temp. generally reduces anthocyanin accumulation in berry skin. To clarify the regulatory mechanism
of anthocyanin biosynthesis under the conditions of high night temps., we examd. flavonoid accumulation, the activities of related
enzymes and gene expression in the anthocyanin biosynthetic pathway in grape berries grown under cool and warm night conditions.
Anthocyanin accumulation in the skin of berries grown at high night temps. (30 °C continuous) was reduced as compared to that of
berries grown at low night temps. (30 °C in daytime/15 °C in night time). On the other hand, flavonol levels in the skin of berries were
not significantly different between low and high night temp. conditions. High night temps. also inhibited the gene expression of
chalcone synthase (CHS), flavanone 3-hydroxylase (F3H), dihydroflavonol 4-reductase (DFR), leucoanthocyanidin dioxygenase
(LDOX) and UDP-glucose: flavonoid 3-O-glucosyltransferase (UFGT) at veraison and an increase in UFGT activity after veraison.
These results suggest that the inhibition of anthocyanin biosynthesis in grape berries grown under high night temp. condition could be
caused by lower expression levels of anthocyanin biosynthetic genes at an early stage of ripening and lower activities of anthocyanin
biosynthetic enzymes, particularly UFGT.
Answer 618:
flavanone
Enzymatic hydrolyzing for naringin increase antioxidant activity of grapefruit juice. Chien, Po J.; Sheu, Fuu; Shyu, Yuan T.;
Yen, Gow C. Department of Food Science, Yuanpei University of Science and Technology, Hsinchu, Taiwan. Taiwan Nongye
Huaxue Yu Shipin Kexue (2005), 43(1), 30-37. Publisher: Agricultural Chemical Society of Taiwan, CODEN: TNHKFW ISSN:
Abstract
Debittering of grapefruit juice could be accomplished through hydrolyzing the bitter flavanone naringin to purine by α-L-rhamnosidase,
and further hydrolyzing purine to naringenin by β-D-glucosidase. The objective of this study was to evaluate the change of antioxidant
activity of the partly/completely debittered grapefruit juices. Results demonstrated that all the debittered juices exhibited superior
activity (p < 0.05) in scavenging DPPH radicals, hydroxyl radicals, hydrogen peroxide, and superoxide radicals to the control. Addnl.,
the trolox equiv. antioxidant capacity (TEAC) value of grapefruit juice increased from 2.47 to 4.02 following the debitter processes
using both α-L-rhamnosidase and β-D-glucosidase. Moreover, the antioxidant activity of naringenin, the aglycon form of naringin, was
significantly (p < 0.05) higher than its glycosides purine and naringin. These results suggest that the enhancement of antioxidant
activity in debittered grapefruit juice could be contributed by the flavanones hydrolysis in the juice. This is the first report describes
that enzymic debittering could fortify the antioxidant activity of grapefruit juice.
Answer 619:
Medicago truncatula isoflavone 2'- or 3'-hydroxylase cDNA sequences and use thereof in transgenic plants for flavonoid and
isoflavonoid nutraceuticals biosynthesis. Dixon, Richard A.; Liu, Chang-Jun. (The Samuel Roberts Noble Foundation, Inc.,
USA). PCT Int. Appl. (2005), 78 pp. CODEN: PIXXD2 WO 2005042747 A2 20050512 Designated States W: AE, AG, AL, AM,
GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO,
NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, UZ, VC, VN, YU, ZA, ZM, ZW.
Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM,

WO 2005042747 A2 20050512 WO 2004-US35948 20041028
WO 2005042747 A3 20070419
RO, RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, UZ, VC, VN, YU, ZA, ZM, ZW,
US
TM, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IT, LU, MC, NL, PL, PT, RO,
SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG, AP, EA, EP, OA
AU 2004286279 A1 20050512 AU 2004-286279 20041028
US 20050172354 A1 20050804 US 2004-976190 20041028
EP 1720986 A2 20061115 EP 2004-810095 20041028
flavanone
R: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IT, LI, LU, MC, NL, PL, PT, RO,
SE, SI, SK, TR, AL, HR, LT, LV, MK
US 2003-515559P P 20031029
WO 2004-US35948 W 20041028
Abstract
The invention provides cDNA sequences of Medicago truncatula isoflavone 2'- or 3'-hydroxylase, and sequence homologs from other
plants. Also provided are constructs comprising these sequences, plants transformed therewith and methods of use thereof. In
certain aspects of the invention, plants transformed with the nucleic acids are provided exhibiting improved pest and disease
resistance. Plants provided by the invention may also exhibit improved nutritional qualities.
Answer 620:
Identification of inhibitors of flavanone 3-hydroxylase expression or activity in plants for screening of herbicides. Davis,
Keith; Zayed, Adel; Ascenzi, Robert; Boyes, Douglas; Hoffman, Neil; Gorlach, Jorn; Woessner, Jeffrey; Hamilton, Carol; Phillips,
Kenneth. (USA). U.S. Pat. Appl. Publ. (2005), 11 pp. CODEN: USXXCO US 2005100879 A1 20050512 Patent written in
English. Application: US 2003-702306 20031106. Priority: . CAN 142:459686 AN 2005:409119 CAPLUS (Copyright (C) 2008

US 20050100879 A1 20050512 US 2003-702306 20031106
US 2003-702306 20031106
Abstract
The present inventors have discovered that Flavanone 3-hydroxylase ("FHT") is essential for plant growth. Specifically, the inhibition
of FHT gene expression in plant seedlings results in small and chlorotic seedlings. Thus, FHT can be used as a target for the
identification of herbicides. Accordingly, the present invention provides methods for the identification of compds. that inhibit FHT
expression or activity. The present invention can be used to identify compds. having herbicide activity by contacting a compd. with
FHT and detecting the presence and/or absence of binding between the compd. and the FHT, or alternatively, detecting a decrease in
FHT expression or activity. The method comprises contacting naringenin, 2-oxoglutarate, and O2 with FHT and the candidate compd.,
and detg. the concn. of naringenin, 2-oxoglutarate, and O2 and/or 3-dihydrokaempferol, succinate and CO2 after the contact.
Answer 621:
flavanone
Linking tumor cell cytotoxicity to mechanism of drug action: An integrated analysis of gene expression, small-molecule
screening and structural databases. Covell, David G.; Wallqvist, Anders; Huang, Ruili; Thanki, Narmada; Rabow, Alfred A.; Lu,
Xiang-Jun. Developmental Therapeutics Program, Screening Technologies Branch, Laboratory of Computational Technologies,
National Cancer Institute-Frederick, Frederick, MD, USA. Proteins: Structure, Function, and Bioinformatics (2005), 59(3),
403-433. Publisher: Wiley-Liss, Inc., CODEN: PSFBAF Journal written in English. CAN 143:37868 AN 2005:400966 CAPLUS
Abstract
An integrated, bioinformatic anal. of three databases comprising tumor-cell-based small mol. screening data, gene expression
measurements, and PDB (Protein Data Bank) ligand-target structures has been developed for probing mechanism of drug action
(MOA). Clustering anal. of GI50 profiles for the NCI's database of compds. screened across a panel of tumor cells (NCI60) was used
to select a subset of unique cytotoxic responses for about 4000 small mols. Drug-gene-PDB relationships for this test set were
examd. by correlative anal. of cytotoxic response and differential gene expression profiles within the NCI60 and structural
comparisons with known ligand-target crystallog. complexes. A survey of mol. features within these compds. finds thirteen conserved
Compd. Classes, each class exhibiting chem. features important for interactions with a variety of biol. targets. Protein targets for an
addnl. twelve Compd. Classes could be directly assigned using drug-protein interactions obsd. in the crystallog. database. Results
from the anal. of constitutive gene expressions established a clear connection between chemo-resistance and overexpression of gene
families assocd. with the extracellular matrix, cytoskeletal organization, and xenobiotic metab. Conversely, chemo-sensitivity
implicated overexpression of gene families involved in homeostatic functions of nucleic acid repair, aryl hydrocarbon metab., heat
shock response, proteasome degrdn. and apoptosis. Correlations between chemo-responsiveness and differential gene expressions
identified chemotypes with nonselective (i.e., many) mol. targets from those likely to have selective (i.e., few) mol. targets.
Applications of data mining strategies that jointly utilize tumor cell screening, genomic, and structural data are presented for
hypotheses generation and identifying novel anti-cancer candidates.
Answer 622:
Inhibition of β-catenin-mediated transactivation by flavanone in AGS gastric cancer cells. Park, Chi Hoon; Hahm, Eun
Ryeong; Lee, Ju Hyung; Jung, Kyung Chae; Yang, Chul Hak. Division of Chemistry and Molecular Engineering, Seoul National
University, Seoul, S. Korea. Biochemical and Biophysical Research Communications (2005), 331(4), 1222-1228. Publisher:
Elsevier, CODEN: BBRCA9 ISSN: 0006-291X. Journal written in English. CAN 143:38040 AN 2005:393597 CAPLUS
Abstract
Recently, data which prove that Wnt pathway activation may be an early event in multistep carcinogenesis in the stomach have been
accumulating. We examd. the effect of flavanone against β-catenin/Tcf signaling in AGS gastric cancer cells. Reporter gene assay
showed that flavanone inhibited β-catenin/Tcf signaling efficiently. In addn., the inhibition of β-catenin/Tcf signaling by flavanone in
HEK293 cells transiently transfected with constitutively mutant β-catenin gene, whose product is not phosphorylated by GSK3β,
indicates that its inhibitory mechanism was related to β-catenin itself or downstream components. To investigate the precise inhibitory
mechanism, we performed immunofluorescence, Western blot, and EMSA. As a result, our data revealed that there is no change of
β-catenin distribution and of nuclear β-catenin levels through flavanone. In addn., the binding of Tcf complexes to DNA is not
influenced by flavanone. The β-catenin/Tcf transcriptional target gene cyclin D1 was downregulated by flavanone. These data
suggest that flavanone inhibits the transcription of β-catenin/Tcf responsive genes, by modulating Tcf activity without disrupting
β-catenin/Tcf complex formation.
Answer 623:
flavanone
Molecular linkage mapping and phylogeny of the chalcone synthase multigene family in soybean. Matsumura, H.;
Watanabe, S.; Harada, K.; Senda, M.; Akada, S.; Kawasaki, S.; Dubouzet, E. G.; Minaka, N.; Takahashi, R. Graduate School of Life
and Environmental Sciences, University of Tsukuba, Tsukuba, Ibaraki, Japan. Theoretical and Applied Genetics (2005), 110(7),
1203-1209. Publisher: Springer GmbH, CODEN: THAGA6 ISSN: 0040-5752. Journal written in English. CAN 143:456231 AN
Abstract
Chalcone synthase (CHS), the key enzyme in the flavonoid biosynthesis pathway, is encoded by a multigene family, CHS1-CHS8
and dCHS1 in soybean. A tandem repeat of CHS1, CHS3 and CHS4, and dCHS1 that is believed to be located in the vicinity
comprises the I locus that suppresses coloration of the seed coat. This study was conducted to det. the location of all CHS members
by using PCR-based DNA markers. Primers were constructed based on varietal differences in either the nucleotide sequence of the
5'-upstream region or the first intron of two cultivars, Misuzudaizu, with a yellow seed coat (II), and Moshidou Gong 503, with a brown
seed coat (ii). One hundred and fifty recombinant inbred lines that originated from a cross between these two cultivars were used for
linkage mapping together with 360 markers. Linkage mapping confirmed that CHS1, CHS3, CHS4, dCHS1, and the I locus are located
at the same position in mol. linkage group (MLG) A2. CHS5 was mapped at a distance of 0.3 cM from the gene cluster. CHS2 and
CHS6 were located in the middle region of MLGs A1 and K, resp., while CHS7 and CHS8 were found at the distal end of MLGs D1a and
B1, resp. Phylogenetic anal. indicated that CHS1, CHS3, CHS4, and CHS5 are closely related, suggesting that gene duplication may
have occurred repeatedly to form the I locus. In addn., CHS7 and CHS8 located at the distal end and CHS2, CHS6, and CHS
members around the I locus located around the middle of the MLG are also related. Ancient tetraploidization and repeated duplication
may be responsible for the evolution of the complex genetic loci of the CHS multigene family in soybean.
Answer 624:
Cloning and molecular analysis of the regulatory factor HlMyb1 in Hop (Humulus lupulus L.) and the potential of Hop to
produce bioactive prenylated flavonoids. Matousek, Jaroslav; Vrba, Lukas; Novak, Petr; Patzak, Josef; De Deeukeleire, Jelle;
Skopek, Josef; Heyerick, Arne; Roldan-Ruiz, Isabel; De Keukeleire, Denis. Institute of Plant Molecular Biology AS CR, Ceske
Budejovice, Czech Rep. Journal of Agricultural and Food Chemistry (2005), 53(12), 4793-4798. Publisher: American Chemical
Abstract
The concns. of prenylated chalcones and bitter acids were analyzed in Czech hop varieties. The highest levels of (xanthohumol +
desmethylxanthohumol) (0.97%, m/m) and of total bitter acids (17.19%, m/m) were obsd. for cv. Agnus. The concn. ratios of bitter
acids to prenylated chalcones varied depending on the genotype, thereby suggesting genetic detn. by different set(s) of structural and
regulatory genes. Promoter elements of the chs_H1 gene encoding a "true" chalcone synthase, a candidate gene to co-det. the
biosynthesis of prenylated chalcones, were analyzed, and several boxes for cis-regulatory elements including Myb transcription
factors were discovered. A cDNA library was established from glandular tissue-enriched cones of cv. Osvald's clone 72 and used to
screen for Myb regulatory elements. The cDNA of the first Myb regulatory factor from hop, called HlMyb1, was cloned and analyzed.
The HlMyb1 open reading frame encodes 272 amino acids (29.8 kDa), and the protein showed highest homol. to the light-regulated
factor AtMyb68 from Arabidopsis thaliana within the Myb domain, whereas there was no significant homol. with known MYB proteins
outside this domain. Unlike AtMyb68, which is expressed in mature leaves, HlMyb1 is strongly expressed in hop inflorescences and
could participate in the regulation of developmental processes involved in the prodn. of hop cones and bioactive secondary
metabolites.
Answer 625:
flavanone
Impact of High Pressure and Pulsed Electric Fields on Bioactive Compounds and Antioxidant Activity of Orange Juice in
Comparison with Traditional Thermal Processing. Sanchez-Moreno, Concepcion; Plaza, Lucia; Elez-Martinez, Pedro; De Ancos,
Begona; Martin-Belloso, Olga; Cano, M. Pilar. Department of Plant Foods Science and Technology, Instituto del Frio, CSIC, Madrid,
Spain. Journal of Agricultural and Food Chemistry (2005), 53(11), 4403-4409. Publisher: American Chemical Society, CODEN:
JAFCAU ISSN: 0021-8561. Journal written in English. CAN 143:77281 AN 2005:373734 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
Bioactive compds. (vitamin C, carotenoids, and flavanones) and DPPH.bul. radical scavenging capacity (RSC) were measured in
orange juice (OJ) subjected to different technologies. High pressure (HP) (400 MPa/40 °C/1 min), pulsed elec. fields (PEF) (35
kVcm-1/750 μs), low pasteurization (LPT) (70 °C/30 s), high pasteurization (HPT) (90 °C/1 min), HPT plus freezing (HPT+F) (-38 °C/15
min), and freezing (F) were studied. Among the treatments assayed, even though the losses in total vitamin C were <9%, treatments
with the higher temps. tended to show the higher decrease in the content of both forms of vitamin C. HP treatment led to an increased
carotenoid release (53.88%) and vitamin A value (38.74%). PEF treatment did not modify individual or total carotenoids content.
Traditional thermal treatments did not exert any effect on total carotenoid content or vitamin A value. With regard to individual
carotenoid extn., HPT and HPT+F led to different releases of carotenoids. With respect to flavanones, HP treatment led to increased
naringenin (20.16%) and hesperetin (39.88%) contents, whereas PEF treatment did not modify flavanone content. In general,
pasteurization and freezing process led to a diminished naringenin content (16.04%), with no modification in hesperetin. HP and PEF
treatments did not modify DPPH.bul. RSC. In the case of traditional thermal technologies, HPT treatment showed a decrease in RSC
(6.56%), whereas LPT, HPT+F, and F treatments did not modify RSC. Vitamin C modulated RSC, in terms of antioxidant concn.
(EC50) and kinetics (AE = 1/EC50TEC50), in the treated and untreated OJ. In summary, HP and PEF technologies were more
effective than HPT treatment in preserving bioactive compds. and RSC of freshly squeezed orange juice.
Answer 626:
Experimental Determination of Octanol-Water Partition Coefficients of Quercetin and Related Flavonoids. Rothwell, Joseph
A.; Day, Andrea J.; Morgan, Michael R. A. Procter Department of Food Science, University of Leeds, Leeds, UK. Journal of
Abstract
Octanol-water partition coeff. (log P) values were detd. for flavonoids from the flavone, flavonol, flavanone, and isoflavonoid
subclasses. Each flavonoid was dissolved in an octanol-water system and allowed to equilibrate, and then both fractions were
analyzed by high-performance liq. chromatog. Log P was calcd. as log[ratio of the concn. in the octanol phase to the concn. in the aq.
phase at pH 7.4]. The aglycons were more lipophilic than any conjugate. The conjugate moiety had a more significant effect on log P
than the aglycon moiety. Quercetin was the least lipophilic aglycon (log P = 1.82 ± 0.32) and, together with kaempferol (log P = 3.11 ±
0.54), gave the most variable results. The isoflavones genistein and daidzein and the isoflavone metabolite equol gave relatively high
log P values (3.04 ± 0.02, 2.51 ± 0.06, and 3.20 ± 0.13, resp.), while glycitein had an unexpectedly low value of 1.97 ± 0.05. The
conjugation characteristics and hydroxylation pattern were the most important determinants of log P in general, and log P was highly
variable within the flavonoid subclass. The results are discussed in terms of further understanding of the in vivo fate of the
flavonoids as important dietary bioactives.
Answer 627:
Partial reconstruction of flavonoid and isoflavonoid biosynthesis in yeast using soybean type I and type II chalcone
flavanone
isomerases. Ralston, Lyle; Subramanian, Senthil; Matsuno, Michiyo; Yu, Oliver. Donald Danforth Plant Science Center, St.
Louis, MO, USA. Plant Physiology (2005), 137(4), 1375-1388. Publisher: American Society of Plant Biologists, CODEN:
PLPHAY ISSN: 0032-0889. Journal written in English. CAN 143:55477 AN 2005:372992 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
Flavonoids and isoflavonoids are major plant secondary metabolites that mediate diverse biol. functions and exert significant ecol.
impacts. These compds. play important roles in many essential physiol. processes. In addn., flavonoids and isoflavonoids have
direct but complex effects on human health, ranging from reducing cholesterol levels and preventing certain cancers to improving
women's health. In this study, we cloned and functionally characterized five soybean (Glycine max) chalcone isomerases (CHIs), key
enzymes in the phenylpropanoid pathway that produces flavonoids and isoflavonoids. Gene expression and kinetics anal. suggest that
the soybean type I CHI, which uses naringenin chalcone as substrate, is coordinately regulated with other flavonoid-specific genes,
while the type II CHIs, which use a variety of chalcone substrates, are coordinately regulated with an isoflavonoid-specific gene and
specifically activated by nodulation signals. Furthermore, we found that some of the newly identified soybean CHIs do not require the
4'-hydroxy moiety on the substrate for high enzyme activity. We then engineered yeast (Saccharomyces cerevisiae) to produce
flavonoid and isoflavonoid compds. When one of the type II CHIs was coexpressed with an isoflavone synthase, the enzyme
catalyzing the first committed step of isoflavonoid biosynthesis, various chalcone substrates added to the culture media were
converted to an assortment of isoflavanones and isoflavones. We also reconstructed the flavonoid pathway by coexpressing CHI
with either flavanone 3β-hydroxylase or flavone synthase II. The in vivo reconstruction of the flavonoid and isoflavonoid pathways in
yeast provides a unique platform to study enzyme interactions and metabolic flux.
Answer 628:
Evaluation of the antioxidant activity by flow injection analysis method with electrochemically generated ABTS radical
cation. Ivekovic, Damir; Milardovic, Stjepan; Roboz, Mario; Grabaric, Bozidar S. Laboratory of General and Inorganic Chemistry
and Electroanalysis, Faculty of Food Technology and Biotechnology, University of Zagreb, Zagreb, Croatia. Analyst (Cambridge,
United Kingdom) (2005), 130(5), 708-714. Publisher: Royal Society of Chemistry, CODEN: ANALAO ISSN: 0003-2654. Journal
Abstract
A Trolox equiv. antioxidant capacity (TEAC) decolorization assay was adapted to a flow injection anal. (FIA) system and a simple and
rapid method for antioxidant activity evaluation was developed. To avoid the time consuming step of
2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical cation prepn. by chem. oxidn. of ABTS, as in the original TAEC
assay, and hence, to shorten the anal. time, the ABTS radical cation was generated online by electrochem. oxidn. of ABTS in the
flow-through electrolysis cell forming a part of the FIA system. The proposed method was optimized with respect to a flow rate,
injection vol. and ABTS radical cation/carrier ratio. Under the optimized conditions linear calibration graphs for Trolox were obtained
over the range 10-100 μM, with a limit of detection 1.6 μM. Good reproducibility (relative std. deviation 1.95%) and sample throughput
(32 samples per h) were achieved. The developed method was applied to the evaluation of the antioxidant activity of pure compds.
and samples of some common beverages. In both cases a good correlation between the results obtained by the proposed method and
TEAC values evaluated by the classic TAEC decolorization assay was obtained (r2 = 0.996 for pure compds. and r2 = 0.957 for
beverage samples).
Answer 629:
Hydrophobic properties of a number of monosubstituted flavone and flavanone derivatives. Pogodaeva, N. N.; Medvedeva,
flavanone
S. A. Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, Irkutsk, Russia. Russian Journal of
Physical Chemistry (2005), 79(4), 645-648. Publisher: Pleiades Publishing, Inc., CODEN: RJPCAR ISSN: 0036-0244. Journal
Abstract
The distribution of flavone, 7-,5-,3-,4'-hydroxyflavones, 3-, 4'-methoxyflavones, and 3-hydroxyflavanone in the octanol-water system
was studied. The hydrophobicity consts. of the flavonoids were detd. It was shown that, when a hydroxy group is substituted into
position 4', the hydrophobicity of flavone decreases, increasing, however, when it is substituted into positions 7, 5, or 3; the increase
is higher the closer it is located to the carbonyl (electron-acceptor) group.
Answer 630:
Preparation and use of 8-prenylnaringenin for hormone replacement therapy. Huempel, Michael; Schleuning, Wolf-Dieter;
Schaefer, Olaf; Isaksson, Paeivi; Bohlmann, Rolf. (Schering Aktiengesellschaft, Germany). Eur. Pat. Appl. (2005), 19 pp.
CODEN: EPXXDW EP 1524269 A1 20050420 Designated States R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC,
PT, IE, SI, LT, LV, FI, RO, MK, CY, AL, TR, BG, CZ, EE, HU, SK. Patent written in English. Application: EP 2003-90335

EP 1524269 A1 20050420 EP 2003-90335 20031007
WO 2005037816 A1 20050428 WO 2004-EP11466 20041006
ZW
SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG
EP 1670777 A1 20060621 EP 2004-765949 20041006
TR, BG, CZ, EE, HU, PL, SK, HR
JP 2007507462 T 20070329 JP 2006-530149 20041006
US 20070276032 A1 20071129 US 2007-575391 20070205
EP 2003-90335 A 20031007
WO 2004-EP11466 W 20041006
Abstract
flavanone
The present invention provides a method for the synthesis of phytoestrogen 8-prenylnaringenin (I) comprising the steps: (a)
diacetylation of naringenin, (b) prenylation using tributyl-phosphine and diisopropylazodicarboxylate, (c) rearrangement of prenyl side
chain using europium(III)-fod and (d) solvolysis using K2CO3 in methanol/H2O. The prepd. naringenin deriv. I was utilized for the
prodn. of a medicament for the prevention and treatment of hormone-dependent osteoporosis and of peri- and postmenopausal
symptoms in women wherein the effect of said medicament on uterus proliferation is less than 1/5 of that of estradiol (II) and the
doses of I and II which are compared are equieffective on bone mass redn.
Me Me
OH
HO O
OH O I
Answer 631:
Synergistic interaction between hesperidin, a natural flavonoid, and diazepam. Fernandez, Sebastian P.; Wasowski, Cristina;
Paladini, Alejandro C.; Marder, Mariel. Facultad de Farmacia y Bioquimica, Instituto de Quimica y Fisicoquimica Biologicas, Buenos
Aires, Argent. European Journal of Pharmacology (2005), 512(2-3), 189-198. Publisher: Elsevier B.V., CODEN: EJPHAZ ISSN:
Abstract
It has been recently reported the presence in Valeriana of the flavone 6-methylapigenin and the flavanone glycoside hesperidin. The
apigenin deriv. is a ligand for the benzodiazepine binding site in the γ-aminobutyric acid receptor type A (GABAA) and has anxiolytic
properties. Hesperidin has sedative and sleep-enhancing properties but is not a ligand for the benzodiazepine binding site.
6-Methylapigenin is able to potentiate the sleep-enhancing effect of hesperidin. In this work we demonstrate that this property is
shared with various GABAA receptor ligands, among them the agonist diazepam, which was used to study the potentiation as measured
in the hole board test. Isobolar anal. of the results showed the interaction being synergistic. We discarded pharmacokinetic effects or
a direct action of hesperidin on the benzodiazepine binding site. A possible use of hesperidin properties to decrease the effective
therapeutic doses of benzodiazepines is suggested.
Answer 632:
Development of restriction fragment length polymorphism (RFLP) markers for identification of strawberry cultivars. Kuniji,
Miyuki; Matsumoto, Akira; Fukino, Nobuko. (National Institute of Agro-Environmental Sciences, Japan). Jpn. Kokai Tokkyo Koho
(2005), 34 pp. CODEN: JKXXAF JP 2005102535 A 20050421 Patent written in Japanese. Application: JP 2003-337714

flavanone

JP 2005102535 A 20050421 JP 2003-337714 20030929
JP 4065951 B2 20080326
JP 2003-337714 20030929
Abstract
A method for identifying strawberry cultivars by PCR-RFLP is disclosed. Using one of 19 pairs of primers, DNA extd. from fruit,
calyx, leaf, or stalk of strawberry, are amplified by PCR. PCR amplified fragments are then digested with a restriction enzyme and
resulting restriction fragment length polymorphisms (RFLPs) are analyzed. The authors developed 19 restriction fragment length
polymorphism (RFLP) markers to identify strawberry (Fragaria × ananassa Duch.) cultivars, with an aim of protecting breeders' rights.
The DNA is extd. from calyx-contg. fruit and/or leaf of strawberry and analyzed by PCR for genotyping. They successfully used
them to distinguish 24 com. cultivars. The results were highly reproducible among different extn. methods, different organs and
different researchers.
Answer 633:
Transcriptome analysis of alfalfa glandular trichomes. Aziz, Naveed; Paiva, Nancy L.; May, Gregory D.; Dixon, Richard A.
Plant Biology Division, Samuel Roberts Noble Foundation, Ardmore, OK, USA. Planta (2005), 221(1), 28-38. Publisher: Springer
GmbH, CODEN: PLANAB ISSN: 0032-0935. Journal written in English. CAN 142:460124 AN 2005:339691 CAPLUS
Abstract
Glandular trichomes are a major site of plant natural product synthesis and accumulation for protection against insect predation.
However, to date few studies have attempted to obtain a global view of trichome gene expression. Two contrasting approaches have
been adopted to investigate genes expressed in glandular trichomes from alfalfa (Medicago sativa). In the first approach, 5674 clones
from an alfalfa glandular trichome cDNA library were sequenced. The most highly abundant expressed sequence tag (EST)
corresponded to a lipid transfer protein. The presence of ESTs corresponding to enzymes for all steps in the biosynthesis of
flavonoids suggests that these are important metabolites in alfalfa trichome biol., as confirmed by histochem. and metabolite profiling.
No ESTs corresponded to enzymes of cyclized terpenoid biosynthesis. In a second approach, microarray anal. was used to compare
levels of alfalfa transcripts corresponding to 16,086 Medicago truncatula A17 genes in stems with and without trichomes. This revealed
over 1000 genes with strong preferential expression in the trichome fraction of the stem, 70% of which are of unknown function.
These define a class of genes that are not trichome-specific, since M. truncatula A17 does not itself have glandular trichomes, but has
potential importance for trichome function within the stem. The EST sequences are deposited in GenBank/EMBL/DDBJ under
accession nos. CO511688-CO517334.
Answer 634:
Chalcones and other flavonoids from Asarum sensu lato (Aristolochiaceae). Iwashina, Tsukasa; Kitajima, Junichi; Shiuchi,
Toshiaki; Itou, Yutaka. Tsukuba Botanical Garden, National Science Museum, Tsukuba, Ibaraki, Japan. Biochemical Systematics
and Ecology (2005), 33(6), 571-584. Publisher: Elsevier B.V., CODEN: BSECBU ISSN: 0305-1978. Journal written in English.
flavanone
Abstract
Seventy-five taxa belonging to the genus Asarum sensu lato were studied for their compn. of flavonoids. Three chalcones and an
aurone were found as major components. The chalcones were identified as chalcononaringenin 2',4'-di-O-glucoside,
4,2',4'-tri-O-glucoside, 4-O-glucoside, and the aurone as aureisidin 4,6-di-O-glucoside. The glycoside, 2',4'-di-O-glucoside was detected
in all taxa examd., and is a chemotaxonomical feature of Asarum sensu lato. 4,2',4'-Tri-O-glucoside was found from the taxa classified
into the genera Asiasarum, Geotaenium and Heterotropa by Maekawa's system. On the other hand, the glycoside was not detected
from three Asarum sensu stricto species, A. caudigerum, A. caulescens and A. leptophyllum. In contrast, aurone, aureusidin
4,6-di-O-glucoside occurred in two Asarum s.s., A. caulescens and A. leptophyllum. Thus, the Asarum s.s. and other Maekawa's
genera, Asiasarum, Geotaenium and Heterotropa could distinguish by the presence or absence of some anthochlor pigments. Other
flavonoids were isolated from the selected 18 Asarum species. They were characterized as some flavonol 3- or 3,7-O-glycosides
based on kaempferol, quercetin and isorhamnetin, flavone, apigenin 6,8-di-C-glycoside, flavanone, naringenin 5,7-di-O-glucoside, and
xanthone, mangiferin.
Answer 635:
Anthocyaninless cultivars of sweet orange lack to express the UDP-glucose flavonoid 3-O-glucosyl transferase. Lo Piero,
Angela R.; Consoli, Alessandro; Puglisi, Ivana; Orestano, Greta; Recupero, Giuseppe Reforgiato; Petrone, Goffredo. Dipartimento di
Scienze Agronomiche, Agrochimiche e delle Produzioni Animali, Facolta di Agraria, Universita degli Studi, Catania, Italy. Journal of
Plant Biochemistry and Biotechnology (2005), 14(1), 9-14. Publisher: Society for Plant Biochemistry and Biotechnology, CODEN:
JPBBEE ISSN: 0971-7811. Journal written in English. CAN 143:382820 AN 2005:313748 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
In this study we isolated the partial cDNA clone of three enzymes active in the late steps of anthocyanins biosynthetic pathway such
as DFR, ANS and UFGT from Citrus sinensis (L) Osbeck. The predicted amino acids sequences shared very high identity values
ranging from 77% for DFR (Pyrus communis, Malus domestica), to 86% for ANS (Vitis vinifera) with homologous available protein
sequences. Only the UFGT sequence showed lower identity value (59%), but this finding is in accordance with data obtained for other
enzymes belonging to the plant glucosyl transferase superfamily. The expression of CHS, CHI, F3OH, DFR, ANS and UFGT was
also investigated in both colored and uncolored oranges juice vesicles. Transcripts encoding the enzymes involved in the earlier
reactions have been detected in either blood and blonde oranges by RT-PCR. Conversely, considerable difference emerged in the
case of the later gene ufgt which was totally unexpressed in blonde oranges juice vesicles probably detg. the lack of anthocyanins
prodn. in all blonde orange cultivars analyzed.
Answer 636:
Differential combinatorial interactions of cis-acting elements recognized by R2R3-MYB, BZIP, and BHLH factors control
light-responsive and tissue-specific activation of phenylpropanoid biosynthesis genes. Hartmann, Ulrike; Sagasser, Martin;
Mehrtens, Frank; Stracke, Ralf; Weisshaar, Bernd. Department of Plant Breeding and Yield Physiology, Max-Planck-Institute for
Plant Breeding Research, Cologne, Germany. Plant Molecular Biology (2005), 57(2), 155-171. Publisher: Kluwer Academic
Publishers, CODEN: PMBIDB ISSN: 0167-4412. Journal written in English. CAN 143:280320 AN 2005:309298 CAPLUS
Abstract
flavanone
Chalcone synthase (CHS), chalcone flavanone isomerase (CFI), flavanone 3-hydroxylase (F3H) and flavonol synthase (FLS)
catalyze successive steps in the biosynthetic pathway leading to the prodn. of flavonols. The authors show that in Arabidopsis
thaliana all four corresponding genes are coordinately expressed in response to light, and are spatially coexpressed in siliques, flowers
and leaves. Light regulatory units (LRUs) sufficient for light responsiveness were identified in all four promoters. Each unit consists
of two necessary elements, namely a MYB-recognition element (MRE) and an ACGT-contg. element (ACE). C1 and Sn, a R2R3-MYB
and a BHLH factor, resp., known to control tissue specific anthocyanin biosynthesis in Z. mays, were together able to activate the
AtCHS promoter. This activation of the CHS promoter required an intact MRE and a newly identified sequence designated R response
element (RREAtCHS) contg. the BHLH factor consensus binding site CANNTG. The RRE was dispensable for light responsiveness,
and the ACE was not necessary for activation by C1/Sn. These data suggest that a BHLH and a R2R3-MYB factor cooperate in
directing tissue-specific prodn. of flavonoids, while an ACE-binding factor, potentially a BZIP, and a R2R3-MYB factor work together in
conferring light responsiveness.
Answer 637:
Implication of cyclic nucleotide phosphodiesterase inhibition in the vasorelaxant activity of the citrus-fruits flavonoid
(±)-naringenin. Orallo, Francisco; Camina, Mercedes; Alvarez, Ezequiel; Basaran, Helene; Lugnier, Claire. Departamento de
Farmacologia, Facultad de Farmacia, Universidad de Santiago de Compostela, Santiago de Compostela, Spain. Planta Medica
(2005), 71(2), 99-107. Publisher: Georg Thieme Verlag, CODEN: PLMEAA ISSN: 0032-0943. Journal written in English. CAN
Abstract
The potential vasorelaxant, antioxidant, and cyclic nucleotide phosphodiesterase (PDE) inhibitory effects of the citrus-fruit flavonoids
naringin and (±)-naringenin were comparatively studied for the 1st time in this work. (±)-Naringenin (1 μM - 0.3 mM) did not affect the
contractile response induced by okadaic acid (OA, 1 μM). However, (±)-naringenin relaxed, in a concn.-dependent manner, the
contractions elicited by phenylephrine (PHE, 1 μM) or by a high extracellular KCl concn. (60 mM) in intact rat aortic rings. Mech.
removal of endothelium and/or pretreatment of aorta rings with glibenclamide (GB, 10 μM) or tetraethylammonium (TEA, 2 mM) did not
significantly modify the vasorelaxant effects of this flavanone. (±)-Naringenin (10 μM - 0.1 mM) did not alter the basal uptake of
45Ca2+ but decreased the influx of 45Ca2+ induced by PHE and KCl in endothelium-contg. and endothelium-denuded rat aorta.
(±)-Naringenin (10 μM - 0.1 mM) was ineffective to scavenge superoxide radicals (O2⋅-) generated by the hypoxanthine (HX)-xanthine
oxidase (XO) system and/or to inhibit XO activity. (±)-Naringenin (0.1 mM) significantly increased the prodn. of cGMP and cAMP
decreased by PHE (1 μM) and high KCl (60 mM) in cultured rat aortic myocytes. (±)-Naringenin preferentially inhibited calmodulin
(CaM)-activated PDE1, PDE4, and PDE5 isolated from bovine aorta with IC50 values of about 45, 60, and 68 μM, resp. In contrast,
the 7-rhamnoglucoside of (±)-naringenin, naringin (1 μM - 0.3 mM), was totally inactive in all expts. These results indicate that the
vasorelaxant effects of (±)-naringenin seem to be basically related to the inhibition of PDE1, PDE4, and PDE5 activities.
Answer 638:
Multiple mutagenesis of P450 isoflavonoid synthase reveals a key active-site residue. Sawada, Yuji; Ayabe, Shin-ichi.
Department of Applied Biological Sciences, Nihon University, Fujisawa, Kanagawa, Japan. Biochemical and Biophysical Research
Communications (2005), 330(3), 907-913. Publisher: Elsevier, CODEN: BBRCA9 ISSN: 0006-291X. Journal written in English.
Abstract
The leguminous isoflavonoid skeleton is constructed by P 450 2-hydroxyisoflavanone synthase (CYP93C). Two active-site residues
of CYP93C2, Ser 310 and Lys 375, are crit. for unusual aryl migration of the flavanone substrate. Leu 371 is located near the
flavanone
substrate in a homol. model, and mutant proteins regarding this residue were expressed in recombinant yeast microsomes. The single
mutant, L371V, yielded only inactive P420, but multiple mutants incorporating K375T restored the P 450 fold: the S310T-L371V-K375T
triple mutant showed four times higher P 450 level than the wild type. L371V-K375T and S310T-L371V-K375T produced a mixt. of major
3β-hydroxyflavanone and minor flavone, and 100% flavone, resp., from a flavanone. Thus, Leu 371 appeared to control the substrate
accommodation in favor of hydrogen abstraction from C-3 of the flavanone mol. and contribute to the P 450 fold under the presence
of Lys 375, the residue responsible for aryl migration. The mol. evolution of CYP93 enzymes is discussed.
Answer 639:
Flavonoids from the leaves of Impatiens bicolor. Hasan, Aurangzeb; Tahir, Muhammad Nawaz. Department of Chemistry,
Quaid-i-Azam University, Islamabad, Pak. Turkish Journal of Chemistry (2005), 29(1), 65-70. Publisher: Scientific and Technical
Research Council of Turkey, CODEN: TJCHE3 ISSN: 1300-0527. Journal written in English. CAN 143:208917 AN 2005:288821
Abstract
Three new flavanone glycosides, naringenin 4'-O-β-D-glucuronopyranoside, naringenin 4'-O-α-L rhamnopyranoside and naringenin
4'-O-β-D-xylopyranoside, were characterized from the leaves of Impatiens bicolor, together with 6 known glycosides: naringenin
4'-O-β-D-glucopyranoside, kaempferol 7-O-β-D-glucuronopyranoside, quercetin 3-O-β-D-glucopyranoside, kaempferol
5-O-β-D-xylopyranoside, kaempferol 3-O-β-D-galactopyranoside and kaempferol 7-O-β-D-xylopyranoside. The structures were detd.
by means of co-chromatog., UV, HPLC, EI-MS, FAB-MS and 1H NMR.
Answer 640:
Temporal expression of flavonoid biosynthesis-related genes regulates flower pigmentation in gentian plants. Nakatsuka,
Takashi; Nishihara, Masahiro; Mishiba, Keiichiro; Yamamura, Saburo. Iwate Biotechnology Research Center, Kitakami, Iwate,
Japan. Plant Science (Amsterdam, Netherlands) (2005), 168(5), 1309-1318. Publisher: Elsevier B.V., CODEN: PLSCE4 ISSN:
Abstract
The cDNA clones encoding homologs of flavanone 3-hydroxylase (F3H), anthocyanidin synthase (ANS), flavonoid 3'-hydroxylase
(F3'H) and flavone synthase II (FSII) genes were isolated from petals of Gentiana triflora. Deduced amino acid sequences exhibited
60-80% identities with the corresponding sequences from other dicotyledonous species. Southern blot anal. showed that they were
present as multiple copies in the gentian genome, and Northern blot anal. showed that the flavonoid biosynthesis-related genes could
be classified into three groups by their temporal expression patterns during gentian flower development. The first included chalcone
synthase (CHS) and chalcone isomerase (CHI) expressing during all flower development stages; the second included F3'H and FSII
expressing at flower early developmental stages; and the third included F3H, flavonoid 3',5'-hydroxylase (F3',5'H), dihydroflavonol
4-reductase (DFR), ANS, UDP-glucose:flavonoid 3-O-glucosyltransferase (3GT) and anthocyanin 5-arom. acyltransferase (5AT)
expressing at flower late developmental stages. In general, low or undetectable levels of expression were obsd. in both the leaves and
stems. High performance liq. chromatog. (HPLC) anal. revealed that flavone accumulates from the early flower bud stage, but
anthocyanin accumulation peaked at the later flower anthesis stage. A significant correlation between gene expression and pigment
accumulation has been found, indicating that flavonoid biosynthesis during gentian flower development is regulated by temporal
expression of these genes.
Answer 641:
flavanone
The differential tissue distribution of the citrus flavanone naringenin following gastric instillation. [Erratum to document
cited in CA142:168926]. Abd El Mohsen, Manal; Marks, Joanne; Kuhnle, Gunter; Rice-Evans, Catherine; Moore, Kevin; Gibson,
Glenn; Debnam, Edward; Srai, S. Kaila. Antioxidant Research Group, Wolfson Centre for Age-Related Diseases, GKT School of
Biomedical Sciences, Kings College London, London, UK. Free Radical Research (2005), 39(2), 221-223. Publisher: Taylor &
Francis Ltd., CODEN: FRARER ISSN: 1071-5762. Journal written in English. CAN 143:278325 AN 2005:279266 CAPLUS
Abstract
The cor. versions of Figures 1 and 3 and the legends to Figure 2, Figure 6, and Table 1 are given. On page 1330, left-hand column,
line 4 from the bottom should read: "Royal Free & University College Medical School". The cor. versions of paragraph 3 in the
right-hand column on page 1338 and the beginning of paragraph 2 in the left-hand column on page 1339 are given.
Answer 642:
Synthesis of 7,3'-dimethoxy-4',5'-ethylenedioxyflavanone. Wang, Qiu-an; Zhang, Chun-xiang; Ma, Qiu-juan. State Key
Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences,
Kunming, Peop. Rep. China. Hecheng Huaxue (2005), 13(1), 67-69, 72. Publisher: Hecheng Huaxue Bianjibu, CODEN: HEHUE2
SciFinder (R))
Abstract
A novel flavonolignan analog 7,3'-dimethoxy-4',5'-ethylenedioxyflavanone (I) was synthesized from Vanillin and m-benzenediol by
seven steps in 16.1 % overall yield. The structure was confirmed by 1H NMR, IR and MS.
OMe
MeO O
O
O I
Answer 643:
Cytotoxic lignans from Larrea tridentata. Lambert, Joshua D.; Sang, Shengmin; Dougherty, Ann; Caldwell, Colby G.; Meyers,
Ross O.; Dorr, Robert T.; Timmermann, Barbara N. Department of Chemical Biology, Ernest Mario School of Pharmacy, Rutgers,
flavanone
The State University of New Jersey, Piscataway, NJ, USA. Phytochemistry (Elsevier) (2005), 66(7), 811-815. Publisher:
Elsevier B.V., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 143:4145 AN 2005:265701 CAPLUS
Abstract
Six lignans, including the cyclolignan 3,4'-dihydroxy-3',4'-dimethoxy-6,7'-cyclolignan (I), were isolated from the flowering tops of Larrea
tridentata. Addnl. the flavanone, (S)-4',5-dihydroxy-7-methoxyflavanone, was isolated for the first time from L. tridentata or any
member of the family Zygophyllaceae. All of the compds. were assessed for their growth inhibitory activity against human breast
cancer, human colon cancer and human melanoma cell lines. The lignans had IC50 values of 5-60 μM with the linear butane-type
lignans being the most potent, and it was found that colon cancer cells were the least sensitive cell type tested. The relative potency
of linear butane type lignans against human breast cancer appears to correlate pos. with the no. of O-Me groups present on the mol.
HO Me
MeO Me
OMe
OH I
Answer 644:
Polymorphism and expression of isoflavone synthase genes from soybean cultivars. Kim, Hyo-Kyoung; Jang, Yun-Hee;
Baek, Il-Sun; Lee, Jeong-Hwan; Park, Min Joo; Chung, Young-Soo; Chung, Jong-Il; Kim, Jeong-Kook. School of Life Sciences and
Biotechnology, Korea University, Seoul, S. Korea. Molecules and Cells (2005), 19(1), 67-73. Publisher: Korean Society for
Molecular and Cellular Biology, CODEN: MOCEEK ISSN: 1016-8478. Journal written in English. CAN 143:302493 AN
Abstract
Isoflavones are synthesized by isoflavone synthases via the phenylpropanoid pathway in legumes. We have cloned two isoflavone
synthase genes, IFS1 and IFS2, from a total of 18 soybean cultivars. The amino acid residues of the proteins that differed between
cultivars were dispersed over the entire coding region. However, amino acid sequence variation did not occur in conserved domains
such as the ERR triad region, except that one conserved amino acid was changed in the IFS2 protein of the GS12 cultivar (R374G)
and the IFS1 proteins of the 99M06 and Soja99s65 cultivars (A109T, F105I). In three cultivars (99M06, 99M116, and Simheukpi), most
of amino acid changes were such that the difference between the amino acid sequences of IFS1 and IFS2 was reduced. The
expression profiles of three enzymes that convert naringenin to the isoflavone, genistein, chalcone isomerase (CHI), isoflavone
synthase (IFS) and flavanone 3-hydroxylase (F3H) were examd. In general, IFS mRNA was more abundant in etiolated seedings than
mature plants whereas the levels of CHI and F3H mRNAs were similar in the two stages. During seed development, IFS was
expressed a little later than CHI and F3H but expression of these three genes was barely detectable, if at all, during later seed
hardening. In addn., we found that the levels of CHI, F3H, and IFS mRNAs were under circadian control. We also showed that IFS
was induced by wounding and by application of Me jasmonate to etiolated soybean seedings.
Answer 645:
flavanone
Surface flavonoids in Satureja thymbra and Satureja spinosa. Skoula, Melpomeni; Grayer, Renee J.; Kite, Geoffrey C.
School of Plant Sciences, Reading, UK. Biochemical Systematics and Ecology (2005), 33(5), 541-544. Publisher: Elsevier B.V.,
CODEN: BSECBU ISSN: 0305-1978. Journal written in English. CAN 143:74827 AN 2005:234226 CAPLUS (Copyright (C)
Abstract
Satureja thymbra L. and Satureja spinosa L. are endemic plants of the Mediterranean region, characterized by a similar oregano-like
smell. S. thymbra is restricted to the Central and East Mediterranean while S. spinosa is found in Crete, Samos and South West
Anatolia. The qual. compn. of surface flavones of S. thymbra is very different from that of S. spinosa. Three out of five flavones
of S. thymbra were 6-hydroxylated and two of them were 4'-methoxylated. S. spinosa, also contained, in addn. to 6-hydroxylated
flavones, 6- and 8-methoxylated flavones, but no 4'-methoxyflavones. Regarding the quant. compn., it is notable that in both species
flavanones and dihydroflavonols comprise more than 60% of the total surface flavonoid fraction. Apart from this similarity the
surface flavonoid patterns of both species show that there are conspicuous differences at the infrageneric level.
Answer 646:
Syntheses of 1,5-benzothiazepines part XXXI: Syntheses and antimicrobial studies of 10-substituted

7-(monochlorophenyl/dichlorophenyl)-6H-6a,7-dihydro-6-phenyl[1]benzopyrano[3,4-c]-[1,5]benzothiazepines. Pant, Umesh
C.; Dandia, A.; Chandra, Hem; Goyal, Shweta; Pant, Seema. Department of Chemistry, University of Rajasthan, Jaipur, India.
Phosphorus, Sulfur and Silicon and the Related Elements (2005), 180(2), 559-571. Publisher: Taylor & Francis, Inc., CODEN:
PSSLEC ISSN: 1042-6507. Journal written in English. CAN 143:422332 AN 2005:229725 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Two flavindogenides, 3-(2-chlorobenzylidene)-flavanone and 3-(2,4-dichlorobenzylidene)-flavanone reacted with six

5-substituted-2-aminobenzenethiols, the substituents being fluoro, chloro, bromo, Me, methoxy, and ethoxy, to give resp. 12 new
compds., 10-substituted 7-(2-chlorophenyl/2,4-dichlorophenyl)-6H-6a,7-dihydro-6-phenyl[1]benzopyrano[3,4-c][1,5]benzothiazepines in
60-70% yields. The products were characterized on the basis of microanal. data for elements and IR, 1H, and 13C NMR and mass
spectral studies. All the synthesized compds. were evaluated for their antimicrobial activity against the bacteria, Escherichia coli and
GFC, and the fungi, Aspergillus niger, Aspergillus flavus, and Curvularia lunata.
Answer 647:
Spasmolytic flavonoids from Syzygium samarangense (Blume) Merr. & L.M. Perry. Amor, Evangeline C.; Villasenor, Irene M.;
Ghayur, M. Nabeel; Gilani, Anwar H.; Choudhary, M. Iqbal. Institute of Chemistry, College of Science, University of the Philippines,
Quezon City, Philippines. Zeitschrift fuer Naturforschung, C: Journal of Biosciences (2005), 60(1/2), 67-71. Publisher: Verlag der
Zeitschrift fuer Naturforschung, CODEN: ZNCBDA ISSN: 0939-5075. Journal written in English. CAN 143:235636 AN
Abstract
flavanone
The hexane ext. of Syzygium samarangense (Ss.Hex) dose-dependently (10-1000 μg/mL) relaxed the spontaneously contracting
isolated rabbit jejunum. Four rare C-methylated flavonoids with a chalcone and a flavanone skeleton were isolated from Ss.Hex and
were subsequently tested for spasmolytic activity. All flavonoids, identified as 2'-hydroxy-4',6'-dimethoxy-3'-methylchalcone (I),
2',4'-dihydroxy-6'-methoxy-3',5'-dimethylchalcone (II), 2',4'-dihydroxy-6'-methoxy-3'-methylchalcone (III), and
7-hydroxy-5-methoxy-6,8-dimethyl-flavanone (IV), showed dose-dependent spasmolytic activity in the rabbit jejunum with IC50 values
of 148.3±69.4, 77.2±43.5, 142.4±58.6 and 178.5±37.5 μg/mL (mean ± SEM), resp. The dihydrochalcone deriv. of compd. I,
2'-hydroxy-4',6'-dimethoxy-3'-methyldihydrochalcone (V), when tested for spasmolytic activity, did not significantly relax the smooth
muscle relative to the other compds. Verapamil, a std. spasmolytic, has an IC50 value of 0.16±0.04 μg/mL. This is the first report of
the relaxant activity of chalcones, specifically of compds. I-III.
flavanone
OMe
CH CO
CH
HO OMe
Me I
OMe
CH CO OMe
CH
HO OH
Me II
OMe
CH CO
CH
HO OH
Me III
Me
HO O
Me
OMe O IV
OMe
CH 2 CO
CH 2
HO OMe
Me V
Answer 648:
flavanone
Seasonal variation in anti-allergic activity of Citrus fruits and flavanone glycoside content. Kubo, Michinori; Fujita, Tadashi;
Nishimura, Sachiyo; Tokunaga, Masashi; Matsuda, Hideaki; Gato, Takeshi; Tomohiro, Norimichi; Sasaki, Katsuaki; Utsunomiya, Naoki.
School of Pharmaceutical Sciences, Kinki University, Higashiosaka, Osaka, Japan. Natural Medicines (Tokyo, Japan) (2004),
58(6), 284-294. Publisher: Japanese Society of Pharmacognosy, CODEN: NMEDEO ISSN: 1340-3443. Journal written in
Japanese. CAN 143:225963 AN 2005:223102 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
Four main flavanone glycosides (narirutin, hesperidin, naringin and neohesperidin) of Citrus fruits showed inhibitory activities on a
compd. 48/80-induced histamine release from mast cells and a dinitrofluorobenzene (DNFB)-induced triphasic skin reaction. In order to
examine seasonal variation of the content of flavanone glycosides exhibiting anti-allergic activity, seventeen kinds of Citrus fruits and
two kinds of Fortunella fruits were periodically collected from early in July to early in Dec. at Yuasa exptl. farm of Kinki University.
Their flavanone glycoside content was detd. by HPLC. Anti-allergic activity of the collected fruits was examd. by the compd.
48/80-induced histamine release assay. HPLC anal. of the collected Citrus fruits allowed us to assemble them into the following three
groups; (1) a group of which main glycosides are narirutin and hesperidin having rutinoside moiety, such as Citrus unshiu, C. iyo, and
C. sulcata: (2) a group of which main glycosides are naringin and neohesperidin having neohesperidoside moiety, such as C. daidai, C.
hassaku, and C. natsudaidai: (3) a group of which main glycoside is naringin, such as C. grandis, C. naruto, and C. paradis. Any
flavanone glycosides described above were not detected in Fortunella fruits. Anti-allergic activity of immature fruits was superior to
that of mature ones in accordance with the fact that the content of four flavanone glycosides in immature fruits was higher than that in
mature ones. On the basis of these findings, it is expected that immature Citrus fruits will be a medicinal resource for anti-allergic
agents.
Answer 649:
Pharmacognostical evaluation of arctii fructus (5). Chemical constituents from fruits of Amorpha fruticosa. Bai, Liping;
Jiang, Hong; Kang, Tingguo; Zhang, Heming; Jiang, Zhihong; Zhao, Zhongzhen. Department of Chinese Medicines, Liaoning College
of Traditional Chinese medicine, Shenyang, Peop. Rep. China. Natural Medicines (Tokyo, Japan) (2004), 58(6), 275-277.
Publisher: Japanese Society of Pharmacognosy, CODEN: NMEDEO ISSN: 1340-3443. Journal written in English. CAN
Abstract
From the fruits of Amorpha fruticosa L. (Leguminosae), a new natural compd. 6a,12a-dehydrosermundone along with 10 known
compds. (8 flavonoids, 1 bibenzyl and 1 terpene) were isolated. The structure of the new natural compd. was elucidated on the basis
of NMR spectroscopic technique.
Answer 650:
Expression profiling of the estrogen responsive genes in response to phytoestrogens using a customized DNA microarray.
Ise, Ryota; Han, Dalho; Takahashi, Yusuke; Terasaka, Shunichi; Inoue, Akio; Tanji, Masao; Kiyama, Ryoiti. InfoGenes Co., Ltd.,
Tsukuba, Ibaraki, Japan. FEBS Letters (2005), 579(7), 1732-1740. Publisher: Elsevier B.V., CODEN: FEBLAL ISSN: 0014-5793.
flavanone
Abstract
Here, we examd. phytoestrogens, isoflavones (genistein, daidzein, glycitein, biochanin A and ipriflavone), flavones (chrysin, luteolin
and apigenin), flavonols (kaempferol and quercetin), and a coumestan, a flavanone and a chalcone (coumestrol, naringenin and
phloretin, resp.) by means of a DNA microarray assay. A total of 172 estrogen responsive genes were monitored with a customized
DNA microarray and their expression profiles for the above phytoestrogens were compared with that for 17β-estradiol (E2) using
correlation coeffs., or R values, after a correlation anal. by linear regression. While R values indicate the similarity of the response
by the genes, we also examd. the genes by cluster anal. and by their specificity to phytoestrogens (specific to genistein, daidzein or
glycitein) or gene functions. Several genes were selected from p53-related genes (CDKN1A, TP53I11 and CDC14), Akt2-related genes
(PRKCD, BRCA1, TRIB3 and APPL), mitogen-activated protein kinase-related genes (RSK and SH3BP5), Ras superfamily genes
(RAP1GA1, RHOC and ARHGDIA) and AP-1 family and related genes (RIP140, FOS, ATF3, JUN and FRA2). We further examd. the
exts. from two local crops of soy beans (Kuro-daizu or Mochi-daizu) by comparing the gene expression profiles with those of E2 or
phytoestrogens as a first step in utilizing the expression profiles for various applications.
Answer 651:
Chemical constituents of Dendrobium trigonopus. Zhang, Ting; Zhang, Chao-Feng; Wang, Zheng-Tao; Xu, Luo-Shan.
Department of Pharmacognosy, China Pharmaceutical University, Nanjing, Peop. Rep. China. Zhongguo Tianran Yaowu (2005),
3(1), 28-30. Publisher: Zhongguo Tianran Yaowu Bianjibu, CODEN: ZTYHA7 ISSN: 1672-3651. Journal written in Chinese. CAN
Abstract
Compds. were isolated from D. trigonopus by silica gel, Sephadex LH-20 and RP-C18 column chromatog. and the structures were
elucidated on the basis of spectroscopic methods. Nine compds. were isolated and identified as a lignan ((+)-syringaresinol); a
fluorenone (dendroflorin); three bibenzyls (moscatilin, gigantol, tristin); a phenanthrene (moscatin); one flavanone (naringenin) and
phytosterols (β-sitosterol and daucosterol). All the compds. were obtained from this plant for the first time.
Answer 652:
Study of hepatoprotective activities of flavones, flavonols and flavanones in acute liver injury by tetrachloromethane.
Misyuryova, S. V.; Zupanets, I. A.; Zhuravel, I. A.; Kovalyov, V. N.; Hylya, V. P. Nats. Farm. Univ., Ukraine. Visnik Farmatsii
(2004), (3), 66-71. Publisher: Vidavnitstvo NFaU, CODEN: VFIAA2 ISSN: 1562-7241. Journal written in Ukrainian. CAN
Abstract
All investigated synthetical analogs of flavonoids were practically nontoxic, and had anticytolytic and antioxidant activities in a model
acute liver injury by tetrachloromethane. Among 27 investigated compds., 13 showed anticytolytic activity and 8 compds. antioxidant
activity. Among the flavone derivs. with high hepatoprotective activity, compd. I showed high anticytolytic (45.7%) and antioxidant
(60.9%) activity. In flavonol group with high membrane protective activity, compd. II had 42.7% anticytolytic activity and 72.2%
antioxidant activity. All 6 flavanone had high anticytolytic activity (69.7-82.4%).
flavanone
CO 2 H
O
O
O O
O
O OH
Me
O II
O I
Answer 653:
Synthesis and in vivo evaluation of Selenoflavanone: A new class of neuroprotective agent. Kim, Dong-myung; Ryu,
Jong-Hoon; Jeong, Jin-Hyun. College of Pharmacy, Kyung Hee University, Seoul, S. Korea. Abstracts of Papers, 229th ACS
National Meeting, San Diego, CA, United States, March 13-17, 2005 (2005), MEDI-201. Publisher: American Chemical Society,
Washington, D. C CODEN: 69GQMP Conference; Meeting Abstract written in English. AN 2005:191534 CAPLUS (Copyright (C)
Abstract
Selenoflavanone and Flavanone derivs. have been synthesized and evaluated for neuroprotection activity. Heterocyclic compds. with
oxygen atoms are known to possess potent biol. effects. The flavonoids, isoflavonoids, and coumarins which form the bulk of these
compds. are quite polar and have limited use as drugs that pass through membranes. The non-polar property is increased by
substituting oxygen with selenium in the heterocyclic compd. Our group focused on synthesizing selenoheterocyclic compds. with
more non-polar properties. In the Selenoflavanone treated group, the anterior and medial parts of the striatum, and large areas of the
cortex, remained unaffected compared with the control group. The total infarction vols. in the ipsilateral hemisphere of
ischemia-reperfusion mouse were significantly reduced by Selenoflavanone treatment.
Answer 654:
Promoter and expression cassettes for bidirectional gene expression in transgenic non-human cells and organisms.
Heim, Ute; Herbers, Karin; Kunze, Irene. (Sungene GmbH & Co. Kgaa, Germany). PCT Int. Appl. (2005), 62 pp. CODEN:
PIXXD2 WO 2005019459 A1 20050303 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA,
CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP,
KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD,
SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY,
DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent
written in German. Application: WO 2004-EP7255 20040703. Priority: DE 2003-10333479 20030722. CAN 142:274984 AN

flavanone
WO 2005019459 A1 20050303 WO 2004-EP7255 20040703

ZW
AU 2004267161 A1 20050303 AU 2004-267161 20040703
CA 2532903 A1 20050303 CA 2004-2532903 20040703
EP 1711612 A1 20061018 EP 2004-740603 20040703
EP 1711612 B1 20070725
R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT, IE, SI, FI, RO, CY, TR, BG, CZ, EE,
HU, PL, SK
AT 368121 T 20070815 AT 2004-740603 20040703
ES 2289529 T3 20080201 ES 2004-740603 20040703
US 20060150282 A1 20060706 US 2006-565221 20060228
DE 2003-10333479 A 20030722
WO 2004-EP7255 W 20040703
Abstract
The invention relates to transgenic expression cassettes for the expression of two genes in transgenic non-human cells or organisms,
esp. plant cells and plants. Said cassettes comprise the bidirectional promoter of Arabidopsis thaliana found between the ferridoxin and
cysteine synthase genes, or functional equiv. of this promoter. Expression vectors contg. such cassettes and transgenic non-human
organisms expressing the cassettes are also disclosed. The transgenic organisms may be used to prep. food and feed, drugs, and
fine chems. Thus, the expression of two selectable markers from the bidirectional promoter in tobacco and rape was demonstrated.
The genes were expressed in the green tissues, not in flowers or roots. In tobacco, but not in rape, the genes were also expressed in
the pollen.
Answer 655:
QSAR modeling on binding affinity of diverse estrogenic flavonoids: electronic, topological and spatial functions in
quantitative approximation. Mukherjee, Subhendu; Mukherjee, Arup; Saha, Achintya. Department of Chemical Technology,
University of Calcutta, Kolkata, India. THEOCHEM (2005), 715(1-3), 85-90. Publisher: Elsevier B.V., CODEN: THEODJ ISSN:
Abstract
Phytoestrogens have been explored as promising next generation estrogenic drug candidates with min. cardiovascular risks.
Investigating spatial, electronic and topol. properties of the mols., structure-activity relationships were drawn in an endeavor to find out
the basic pharmacophore features of flavonoids for binding with the estrogen receptor. Implementing multi-parameter linear regression
flavanone
anal., a significant relationship (R2=0.892 and Q2=0.805 for n=19) was established that explained 86.097% variance in binding affinity
to the receptor. This study revealed the importance of partial charges at atoms C2' and C4' in the Ph ring C, electrotoplogical state of
atom C7 in the Ph ring A and the mol. orientation and conformational stringency factors. It has been found that substitution by an e-
donating group in the Ph ring at C2', e- withdrawing groups at C4' and C7 of the mol. in conjunction with minimal conformational rigidity
could be important for estrogenic activity.
Answer 656:
Quinone reductase 2 substrate specificity and inhibition pharmacology. Boutin, Jean A.; Chatelain-Egger, Florence; Vella,
Fanny; Delagrange, Philippe; Ferry, Gilles. Pharmacologie Moleculaire et Cellulaire, Institut de Recherches Servier,
Croissy-sur-Seine, Fr. Chemico-Biological Interactions (2005), 151(3), 213-228. Publisher: Elsevier Ireland Ltd., CODEN:
CBINA8 ISSN: 0009-2797. Journal written in English. CAN 143:301200 AN 2005:174051 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Quinone reductase 2 is a mammalian cytosolic FAD-dependent enzyme, the activity of which is not supported by conventional
nicotinamide nucleotides. An endobiotic substrate has never been reported for this enzyme nor a set of mol. tools, such as inhibitors.
In the present work, we used the recombinant human enzyme, expressed in CHO cells for the systematic screening of both
co-substrates and substrates. The co-substrates survey showed that the natural occurring compd., N-ribosylnicotinamide, was a poor
co-substrate. The synthetic N-benzylnicotinamide is a better one compared to any other compds. tested. We found that
tetrahydrofolic acid acted as a co-substrate for the redn. of menadione catalyzed by quinone reductase 2, although with poor potency
(Km .apprx. 2 mM). Among a series of com. available quinones, a single one was found to be substrate of quinone reductase 2, in the
presence of N-benzyldihydronicotinamide: coenzyme Q0. Finally, we tested a series of 197 flavonoids as potential inhibitors. We
found apigenin, genistein or kaempferol as good inhibitor of quinone reductase 2 activity with IC50 in the 100 nM range. These
compds., co-substrate, substrate and inhibitors will permit to better know this enzyme, the role of which is still poorly understood.
Answer 657:
Varietal and interspecific influence on micronutrient contents in citrus from the Mediterranean area. Dhuique-Mayer,
Claudie; Caris-Veyrat, Catherine; Ollitrault, Patrick; Curk, Franck; Amiot, Marie-Josephe. Departement FLHOR, Centre de
Cooperation Internationale en Recherche Agronomique pour le Developpement (CIRAD), Montpellier, Fr. Journal of Agricultural and
Food Chemistry (2005), 53(6), 2140-2145. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal
Abstract
To specify the genotypic variation of Mediterranean Citrus juices, the contents of carotenoids, flavonoids, and vitamin C were detd.
by high-performance liq. chromatog. A selection of orange varieties and Mandarin species from the Mediterranean area (Citrus
sinensis, Citrus deliciosa Ten, and Citrus clementina Hort. ex Tan) was evaluated using carotenoid profiles and flavanones contents.
Among the eight varieties of orange (Salustiana, Hamlin, Shamouti, Pera, Valencia, Maltaise, Sanguinelli, and Cara-cara) and two
Mandarin species, only three cultivars (Pera, Sanguinelli, and Shamouti) and the two Mandarin species displayed a high content of
vitamin A (374, 381, and 272 ER L-1 for the three orange cultivars and 1156 and 960 retinol equiv. (RE) L-1 for the Mandarins) due to a
high content of β-cryptoxanthin. These same Citrus were also rich in hesperidin (502, 537, 552, 767, and 754 mg L-1, resp.). Principal
component anal. allowed the Mediterranean orange varieties and Mandarin species to be differentiated on the basis of nutritional
criteria. Strong correlations were obsd. between β-cryptoxanthin and hesperidin (r = 0.92) and between β-cryptoxanthin and β-carotene
(r = 0.98). In contrast, vitamin C content was not correlated with carotenoids and flavanone glycosides. The Mandarin and orange
flavanone
group was quite distinct. The orange varieties could be divided in two groups. In addn., a diversity tree allowed a genetic approach to
differentiating Citrus cultivars on the basis of Euclidean distances. This representation showed that the hybrid Clementine was nearer
to its parent Mandarin than to its parent orange, suggesting that β-cryptoxanthin was a dominant genetic factor. With regard to vitamin
A, Mandarin and its hybrid Clementine appeared to be the best Citrus species.
Answer 658:
A novel cytotoxic prenylated flavonoid from the root of Morus alba. Kofujita, Hisayoshi; Yaguchi, Masashi; Doi, Norio; Suzuki,
Koichi. Faculty of Agriculture, Iwate University, Morioka, Japan. Journal of Insect Biotechnology and Sericology (2004), 73(3),
113-116. Publisher: Japanese Society of Sericultural Science, CODEN: JIBSBD ISSN: 1346-8073. Journal written in English. CAN
Abstract
A novel prenylated flavanone was isolated from Et acetate exts. of the hard-wood cutting root of Kinuyutaka, a cultivar of Morus alba.
The structure, 7,2',4',6'-tetrahydoroxy-6-geranylflavanone (I), was revealed by spectral analyses. I exhibited cytotoxic activity
against rat hepatoma (dRLh84) cells with an IC50 of 52.8 μg/mL.
HO OH
HO O
Me OH
Me Me O I
Answer 659:
Passive cutaneous anaphylaxis-inhibitory activity of flavanones from Citrus unshiu and Poncirus trifoliata. Park,
Sung-Hwan; Park, Eun-Kyung; Kim, Dong-Hyun. Department of Food and Nutrition, College of Pharmacy, Kyung Hee University,
Seoul, S. Korea. Planta Medica (2005), 71(1), 24-27. Publisher: Georg Thieme Verlag, CODEN: PLMEAA ISSN: 0032-0943.
Abstract
This study examd. the passive cutaneous anaphylaxis-inhibitory activity of the flavanones isolated from the pericarp of Citrus unshiu
(Family Rutaceae) and the fruit of Poncirus trifoliata (Family Rutaceae). Naringenin, hesperetin and ponciretin potently inhibited
IgE-induced β-hexosaminidase release from RBL-2H3 cells and the PCA reaction. Among the flavanones examd., naringenin was the
most potent with an IC50 value for β-hexosaminidase release from RBL-2H3 cells of 0.029 mM. I.p. administered naringenin (5 mg/kg)
inhibited PCA by 70±1.7%, compared with the control group. The inhibitory activity of naringenin was found to be comparable to that
of azelastine, which is a com. available antiallergic drug. However, their glycosides, hesperidin, naringin and poncirin, did not inhibit the
in vitro release of β-hexosaminidase from the RBL-2H3 cells. On the other hand, these flavanones did not improve the
oxazolone-induced dermatitis in the mouse ears. When the flavanone glycosides were administered to rats, the aglycons, but not the
flavanone
flavanone glycosides, were excreted in urine. This suggests that the flavanone glycosides can be activated by intestinal bacteria, and
may be effective toward IgE-induced atopic allergies.
Answer 660:
Isoprenylated xanthones and flavonoids from Cudrania tricuspidata. Zou, Ying-Shu; Hou, Ai-Jun; Zhu, Guo-Fu. Department
of Pharmacognosy, School of Pharmacy, Fudan University, Shanghai, Peop. Rep. China. Chemistry & Biodiversity (2005), 2(1),
131-138. Publisher: Verlag Helvetica Chimica Acta AG, CODEN: CBHIAM ISSN: 1612-1872. Journal written in English. CAN
Abstract
Further phytochem. investigation on the roots of Cudrania tricuspidata afforded a new isoprenylated xanthone, cudratricusxanthone I
(I), two new isoprenylated flavanones, cudraflavanones C and D (II and III, resp.), and seven known compds.,
1,7-dihydroxy-3,6-dimethoxyxanthone, macluraxanthone C, cudraxanthones E, K, and L, cudraflavanone A, and cudraflavone C. Their
structures were identified by spectroscopic methods. Cudratricusxanthone H, macluraxanthone B, two xanthones previously isolated
from this plant, and macluraxanthone C, showed significant inhibitory effects on four kinds of human digestive app. tumor cell lines
(HCT-116, SMMC-7721, SGC-7901, and BGC-823) with IC50 values of 2.70-12.66 μM.
O OH
Me Me
HO
HO O O Me I
HO OMe
Me
HO O
Me CH 2 CH C Me
Me C CH CH 2
OH O II
HO OH
Me
HO O
Me CH 2 CH C Me
Me C CH CH 2
OH O III
flavanone
Answer 661:
The Baccharis genus (Asteraceae): Chemical, economical and biological aspects. Verdi, Luiz Gonzaga; Brighente, Ines Maria
Costa; Pizzolatti, Moacir Geraldo. Departamento de Quimica, Universidade Federal de Santa Catarina, Florianopolis-SC, Brazil.
Quimica Nova (2005), 28(1), 85-94. Publisher: Sociedade Brasileira de Quimica, CODEN: QUNODK ISSN: 0100-4042. Journal;
General Review written in Portuguese. CAN 143:263431 AN 2005:139257 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
A review. The plant genus Baccharis has >500 species growing mainly in the tropical areas of South America. Many of them are
extensively used in folk medicine in the treatment or prevention of anemias, inflammations, diabetes mellitus, and stomach, liver and
prostate diseases. Phytochem. and biol. investigations of .apprx.120 species led to the isolation numerous flavones, flavanones,
diterpenes, and triterpenes. Among them are several clerodane and labdane diterpenes and flavonoid aglycons, with the flavone
moiety being the most frequent.
Answer 662:
Naringenin attenuates cisplatin nephrotoxicity in rats. Badary, Osama A.; Abdel-Maksoud, Sahar; Ahmed, Wafaa A.; Owieda,
Gehan H. Department of Pharmacology and Toxicology, Faculty of Pharmacy, Helwan University, Cairo, Ain Helwan, Egypt.
Life Sciences (2005), 76(18), 2125-2135. Publisher: Elsevier B.V., CODEN: LIFSAK ISSN: 0024-3205. Journal written in English.
Abstract
The effect of naringenin (NAR), a naturally occurring citrus flavanone, on the acute nephrotoxicity produced by cisplatin (7 mg/kg, i.v.)
was investigated in the rat. Oral administration of NAR (20 mg/kg/day) for 10 days, starting 5 days before cisplatin single i.v.
injection, produced significant protection of renal function. NAR reduced the extent of cisplatin-induced nephrotoxicity, as evidenced
by significant redn. in serum urea and creatinine concns., decreased polyuria, redn. in body wt. loss, marked redn. in urinary fractional
sodium excretion and glutathione S-transferase (GST) activity, and increased creatinine clearance. Cisplatin-induced alterations in
renal cortex lipid peroxides and GST activity were markedly improved by NAR. Cisplatin-induced alterations in renal cortex antioxidant
defense system were greatly prevented by NAR. In cisplatin-NAR combined treatment group, antioxidant enzymes namely
superoxide dismutase (SOD), glutathione peroxidase (GSH-Px), and catalase (CAT) were significantly increased to 54.5, 30.3 and
35.6%, resp. compared to cisplatin treated group. Platinum renal content was not affected by NAR treatment. The results provide
further insight into the mechanisms of cisplatin-induced nephrotoxicity and confirm the antioxidant potential of NAR.
Answer 663:
Myricetin inhibits matrix metalloproteinase 2 protein expression and enzyme activity in colorectal carcinoma cells. Ko,
Ching-Huai; Shen, Shing-Chuan; Lee, Tony J. F.; Chen, Yen-Chou. Graduate Institutes of Pharmaceutical Sciences and
Pharmacognosy, School of Pharmacy and Department of Dermatology, School of Medicine, Taipei Medical University, Taipei,
Taiwan. Molecular Cancer Therapeutics (2005), 4(2), 281-290. Publisher: American Association for Cancer Research, CODEN:
MCTOCF ISSN: 1535-7163. Journal written in English. CAN 142:423230 AN 2005:133801 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
flavanone
Abstract
Colorectal carcinoma is a leading cause of human mortality due to its high metastatic ability. Because the activation of matrix
metalloproteinases (MMP) is a key factor in the metastatic process, agents with the ability to inhibit MMP activity have potential in the
treatment of colorectal carcinoma. In the present study, among 36 flavonoids examd., myricetin was found to be the most potent
inhibitor of MMP-2 enzyme activity in COLO 205 cells (IC50 = 7.82 μmol/L). Myricetin inhibition of MMP-2 enzyme activity was also
found in the human colorectal carcinoma cell lines COLO 320HSR, COLO 320DM, HT 29, and COLO 205-X (IC50 = 11.18, 11.56,
13.25, and 23.51 μmol/L, resp.). In contrast, no inhibitory effect of MMP-2 protein expression or enzyme activity was obsd. in
myricitrin (myricetin-3-rhamnoside)-treated cells. In 12-O-tetradecanoylphorbol-13-acetate (TPA)-stimulated COLO 205 cells, an
increase in MMP-2 protein expression and enzyme activity, as well as of protein kinase C (PKC) α protein translocation, extracellular
signal-regulated kinase (ERK) 1/2 protein phosphorylation, and c-Jun protein expression was obsd. ERK inhibitor (PD98059) and PKC
inhibitors (GF-109203X and H-7), but not p38 inhibitor (SB203580) or c-jun-NH2-kinase inhibitor (SP600125), significantly inhibited
TPA-induced MMP-2 protein expression, with reduced ERK phosphorylation and c-Jun protein expression. Addn. of myricetin but not
myricitrin suppressed TPA-induced MMP-2 protein expression in COLO 205 cells by blocking the TPA-induced events, including
translocation of PKCα from cytosol to membrane, phosphorylation of ERK1/2 protein, and induction of c-Jun protein expression.
Addn. of PD98059 or GF-109203X significantly enhanced the inhibitory effect of myricetin on MMP-2 enzyme activity induced by TPA.
Furthermore, myricetin, but not myricitrin, suppressed TPA-induced invasion of COLO 205 cells in an in vitro invasion assay using
Engelbreth-Holm-Swarm sarcoma tumor ext. Matrigel-coated Transwells.
Results of the present study indicate that myricetin significantly blocked both endogenous and TPA-induced MMP-2
enzyme activity by inhibiting its protein expression and enzyme activity. The blockade involved suppression of PKC
translocation, ERK phosphorylation, and c-Jun protein expression.
Answer 664:
Cytotoxic flavanones of Schizolaena hystrix from the Madagascar rainforest. Murphy, Brian T.; Cao, Shugeng; Norris, Andrew;
Miller, James S.; Ratovoson, Fidisoa; Andriantsiferana, Rabodo; Rasamison, Vincent E.; Kingston, David G. I. Department of
Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, VA, USA. Journal of Natural Products (2005), 68(3),
417-419. Publisher: American Chemical Society, CODEN: JNPRDF ISSN: 0163-3864. Journal written in English. CAN 142:370747
Abstract
Bioassay-guided fractionation of an ethanol ext. of a Madagascar collection of Schizolaena hystrix afforded three new flavanones,
schizolaenone A (1), schizolaenone B (2), and 4'-O-methylbonannione A (3), as well as three known flavanones, nymphaeol A,
bonannione A, and macarangaflavanone B, and the flavanol bonanniol A. The structures of compds. 1-3 were detd. by various one-
and two-dimensional NMR techniques. All of the isolates were tested for cytotoxicity against the A2780 human ovarian cancer cell
line. Nymphaeol A (IC50 = 5.5 μg/mL) exhibited the greatest cytotoxicity, while the other flavanones were found to be only weakly
active.
Answer 665:
Cloning and heterologous expression of cDNAs encoding flavonoid glucosyltransferases from Dianthus caryophyllus.
Ogata, Jun; Itoh, Yoshio; Ishida, Madoka; Yoshida, Hiroyuki; Ozeki, Yoshihiro. Department of Biotechnology, Faculty of
Technology, Tokyo University of Agriculture and Technology, Tokyo, Japan. Plant Biotechnology (Tokyo, Japan) (2004), 21(5),
367-375. Publisher: Japanese Society for Plant Cell and Molecular Biology, CODEN: PLBIF6 ISSN: 1342-4580. Journal written in
flavanone
Abstract
Yellow petals of carnations contain chalcone 2'-O-glucoside. The glucosylation occurs after the p-coumaroyl CoA and malonyl-CoA
condensation reaction by chalcone synthase (CHS), but the enzyme(s) transferring glucose from UDP-glucose to the 2'-OH position of
chalcone has not been identified. The full-length cDNA clones for 18 glucosyltransferase (GT) genes were isolated from petal tissue of
carnation (Dianthus caryophyllus) bearing various flower colors. The 18 GTs encoded in the cDNAs were enzymically characterized in
an E. coli expression system using chalcone, flavanone, flavone, flavonol and anthocyanidin as substrates. Three of the 18 were
characterized as 3-GT possessing different substrate specificities for flavonoids and anthocyanidin and another two GTs catalyzed the
transfer of glucose to the 2'-hydroxyl group of chalcone. In addn., these two enzymes glucosylated flavonol (3-OH and 7-OH),
flavanone (7-OH), flavone (7-OH) and anthocyanidin (3-OH and 7-OH).
Answer 666:
Metabolism of administered (2RS)-naringenin in flavonoid-producing cultured cells of Sophora flavescens. Yamamoto,

Hirobumi; Kuribayashi, Hiroki; Seshima, Yasuharu; Zhao, Ping; Kouno, Isao; Taguchi, Goro; Shimomura, Koichiro. Plant Regulation
Research Center, Faculty of Life Sciences, Toyo University, Gunma, Japan. Plant Biotechnology (Tokyo, Japan) (2004), 21(5),
355-359. Publisher: Japanese Society for Plant Cell and Molecular Biology, CODEN: PLBIF6 ISSN: 1342-4580. Journal written in
Abstract
Cultured cells of Sophora flavescens produce (2S)-naringenin-derived prenylated flavanone sophoraflavanone G and
liquiritigenin-derived trifolirhizin 6'-O-malonate. The regulation of flavonoid biosynthesis was examd. by analyzing the metabolites
produced in the cultured cells fed (2RS)-naringenin. The amt. of sophoraflavanone G in cells fed 0.1 or 0.3 mM (2RS)-naringenin was
two-fold that in control cells, although the conversion ratio was only 5 to 10% of the administered (2S)-naringenin. On the other hand,
(2R)-naringenin, which does not occur naturally, was efficiently converted into its 4',7-di-O-β-D-glucoside. (2S)-Naringenin prenylation
activity was higher at the logarithmic growth stage. The cells fed (2RS)-naringenin at a lower concn. (below 0.1 mM), accumulated
sophoraflavanone G as the main prenylated flavanone. In contrast, cells fed 0.3 mM (2RS)-naringenin accumulated 8-prenylnaringenin
and leachianone G, intermediates of sophoraflavanone G in large amts. Accumulation of trifolirhizin 6'-O-malonate was suppressed by
the addn. of naringenin.
Answer 667:
Threshold dissociation and molecular modeling of transition metal complexes of flavonoids. Zhang, Junmei; Brodbelt,
Jennifer S.; Wang, Junmei. Department of Chemistry and Biochemistry, University of Texas, Austin, TX, USA. Journal of the
American Society for Mass Spectrometry (2005), 16(2), 139-151. Publisher: Elsevier Inc., CODEN: JAMSEF ISSN: 1044-0305.
Abstract
The relative threshold dissocn. energies of flavonoid/transition metal/auxiliary ligand complexes [MII (flavonoid - H) auxiliary ligand]+
formed by electrospray ionization (ESI) were measured by energy-variable collisionally activated dissocn. (CAD) in a quadrupole ion
trap (QIT). For each of the isomeric flavonoid diglycoside pairs, the rutinoside (with a 1-6 inter-saccharide linkage) requires a greater
CAD energy and thus has a higher dissocn. threshold than its neohesperidoside (with a 1-2 inter-saccharide linkage) isomer. Likewise,
the threshold energies of complexes contg. flavones are higher than those contg. flavanones. The monoglycoside isomers have
characteristic threshold energies. The flavonoids that are glycosylated at the 3-O- position tend to have lower threshold energies than
flavanone
those glycosylated at the 7-O- or 4'-O- position, and those that are C- bonded have lower threshold energies than the O- bonded
isomers. The structural features that substantially influence the threshold energies include the aglycon type (flavanone vs. flavone),
the type of disaccharide (rutinose vs. neohesperidose), and the linkage type (O- bonded vs. C- bonded). Various computational means
were applied to probe the structures and conformations of the complexes and to rationalize the differences in threshold energies of
isomeric flavonoids. The most favorable coordination geometry of the complexes has a plane-angle of .apprx.62°, which means that
the deprotonated flavonoid and 2,2'-bipyridine within a complex do not reside on the same plane. Stable conformations of 5 Co
complexes and 5 deprotonated flavonoids were identified. The conformations were combined with the point charges and He accessible
surface areas to explain qual. the differences in threshold energies for isomeric flavonoids.
Answer 668:
Screening for tyrosinase inhibitors among extracts of seashore plants and identification of potent inhibitors from Garcinia
subelliptica. Masuda, Toshiya; Yamashita, Daiki; Takeda, Yoshio; Yonemori, Shigetomo. Faculty of Integrated Arts and
Sciences, University of Tokushima, Tokushima, Japan. Bioscience, Biotechnology, and Biochemistry (2005), 69(1), 197-201.
Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry, CODEN: BBBIEJ ISSN: 0916-8451. Journal written in
Abstract
The tyrosinase inhibitory activity of methanol exts. of the leaves of 39 plant species growing on the seashore of Iriomote island
(Okinawa, Japan) was investigated. The exts. of Hibiscus tiliaceus, Carex pumila, and Garcinia subelliptica showed potent activity
among them. The inhibitors in the ext. of Garcinia subelliptica were purified by assay-guided fractionation to give two biflavonoids.
These were known compds. (2R,3S-5,7,4',5'',7'',3''',4'''-heptahydroxy flavanone[3-8''] flavone and
5,7,4',5'',7'',3''',4'''-heptahydroxy[3-8''] biflavanone), although their strong inhibitory activity toward tyrosinase is revealed for the first
time in this work. One of these biflavonoids (2R,3S-5,7,4',5'',7'',3''',4'''-heptahydroxy flavanone[3-8''] flavone) showed much stronger
activity (IC50 2.5 μM) than that of kojic acid (IC50 9.1 μM) when L-tyrosine was used as the substrate.
Answer 669:
Parkintin: a new flavanone with epoxy-isopentyl moiety from Parkinsonia aculeata Linn. (Caesalpiniaceae). Ali, Muhammad
Shaiq; Ahmed, Farman; Pervez, Muhammad Kashif; Azhar, Iqbal; Ibrahim, Syed Amir. H.E.J. Research Institute of Chemistry,
University of Karachi, Karachi, Pak. Natural Product Research (2005), 19(1), 53-56. Publisher: Taylor & Francis Ltd., CODEN:
NPRAAT ISSN: 1478-6419. Journal written in English. CAN 142:407613 AN 2005:121909 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
A new flavanone with epoxy-isopentyl moiety named parkintin (I) has been isolated from the methanol sol. part of Parkinsonia aculeata
Linn. belonging to the family Caesalpiniaceae. The structure of parkintin has been established with the aid of spectroscopic techniques
including COSY and HMBC expts.
flavanone
Me OH
H
Me CH 2 O
O
O I
Answer 670:
Analysis of mutations induced by carbon ions in Arabidopsis thaliana. Shikazono, Naoya; Suzuki, Chihiro; Kitamura, Satoshi;
Watanabe, Hiroshi; Tano, Shigemitsu; Tanaka, Atsushi. Department of Ion Beam Applied Biology, Japan Atomic Energy Research
Institute (JAERI), Takasaki, Gunma, Japan. Journal of Experimental Botany (2005), 56(412), 587-596. Publisher: Oxford
University Press, CODEN: JEBOA6 ISSN: 0022-0957. Journal written in English. CAN 143:20638 AN 2005:109886 CAPLUS
Abstract
To investigate the nature of mutations induced by accelerated ions in higher plants, the effects of carbon-ion-irradn. were compared
with those of electron-irradn. in Arabidopsis thaliana. Point-like mutations and rearrangements were induced at a similar frequency after
carbon-ion-irradn., whereas point-like mutations were more frequently induced after electron-irradn. Sequence anal. revealed that
carbon-ion-induced point-like mutations were mostly short deletions. In the case of rearrangements, deletions, inversions, insertions,
and translocations were found. The estd. frequency of deletion induction was comparable to that of fast neutrons. Anal. of
chromosome breakpoints revealed that carbon ions frequently deleted small regions around the breakpoints, whereas electron-irradn.
often duplicated these regions. Moreover, for both types of radiation, broken ends with microhomologies were frequently rejoined.
Results of the breakpoint and broken end analyses suggest that non-homologous end-joining (NHEJ) leads to the rejoining of double
strand breaks (dsbs) after cells are exposed to both types of radiation, but the type of NHEJ that occurs as a result of damage is
different. The results indicated that carbon-ion-induced mutations are most likely nulls and that the induced rearrangements may arise
through a unique mechanism. These findings indicate that accelerated ions are a useful mutagen for both forward and reverse
genetics for plants.
Answer 671:
Inhibition of hydrogen peroxide-induced endothelial apoptosis by 2',4',7-trihydroxyflavanone, a flavonoid form. Choi,

Yean-Jung; Lee, Myung-Kyu; Lee, Yong-Jin; Jeong, Yu-Jin; Park, Jung Han Yoon; Lim, Soon Sung; Kang, Young-Hee. Division of
Life Sciences, Hallym University, Chuncheon, S. Korea. Journal of Medicinal Food (2004), 7(4), 408-416. Publisher: Mary Ann
Liebert, Inc., CODEN: JMFOFJ ISSN: 1096-620X. Journal written in English. CAN 142:367560 AN 2005:107489 CAPLUS
Abstract
Oxidative stress contributes to cellular injury following clin. and exptl. ischemia/reperfusion episodes. Oxidative injury can induce
cellular and subcellular damage that results in apoptotic cell death. We tested whether 2',4',7-trihydroxyflavanone, a synthetic
flavanone
flavonoid deriv., inhibits hydrogen peroxide (H2O2)-induced toxicity in human umbilical endothelial cells (HUVECs). Cultured HUVECs
were incubated for 30 min with 0.2 mM H2O2 in the absence and presence of 2',4',7-trihydroxyflavanone at a non-toxic concn. of 50
μM. The effect of 2',4',7-trihydroxyflavanone on apoptosis parameters was compared with that of naringenin and two flavonol derivs.,
2',4',7-trihydroxyflavonol and 2',4',6-trihydroxyflavonol. H2O2 induced cell death within 24 h over the range of 0.05-1.0 mM, and
decreased cell viability by .apprx.30% at 0.2 mM. This cytotoxicity was assocd. with nuclear condensation and DNA fragmentation,
indicating induction of apoptosis. 2',4',7-Trihydroxyflavanone, as well as naringenin, was effective as an inhibitor of oxidative stress,
protecting cell viability with ≥85% viable cells compared with the control, and no apparent nuclear condensation or DNA fragmentation.
In contrast, the flavonol derivs. had no such effect. In addn., immunocytochem. data and Western blot anal. revealed that, unlike
flavonol derivs., the expression of Bcl-2 was markedly up-regulated, and that the expression of Bax and activation of caspase-3 were
strongly inhibited by this flavanone deriv., thereby implicating antioxidant activity-related anti-apoptotic mechanisms of
2',4',7-trihydroxyflavanone. These results indicate that the synthetic flavonoid deriv. 2',4',7-trihydroxyflavanone is an effective
antioxidant, preventing endothelial apoptosis induced by H2O2.
Answer 672:
Flavonoids as chemotaxonomic markers for Erythroxylum australe. Johnson, Emanuel L.; Schmidt, Walter F. USDA ARS
Weed Science Laboratory, Beltsville, MD, USA. Zeitschrift fuer Naturforschung, C: Journal of Biosciences (2004), 59(11/12),
769-776. Publisher: Verlag der Zeitschrift fuer Naturforschung, CODEN: ZNCBDA ISSN: 0939-5075. Journal written in English.
Abstract
Methanolic leaf exts. of Erythroxylum australe produced eight O-conjugated flavonoids. Six of the flavonoid aglycons were
dihydroisoflavones (all dihydroorobol derivs.), one a flavanone, eriodictyol, and one a flavonol, quercetin. The major glycosides of the
flavonoids included mono-glucosyl-rhamnosyls and dirhamnosyl-glucosides with either 3,5,7 or 3',4' linkage or a combination thereof.
The array of flavonoids present in E. australe suggests kinship to E. ulei and linkage to the four cultivated alkaloid-bearing
Erythroxylum, esp. the ancestral E. coca var. coca. Because of the uniqueness of the flavonoids present in leaf tissue of E. australe
they are unambiguously useful as chemotaxonomic markers for the taxon.
Answer 673:
Silver complexation and tandem mass spectrometry for differentiation of isomeric flavonoid diglycosides. Zhang, Junmei;
Brodbelt, Jennifer S. Department of Chemistry and Biochemistry, University of Texas, Austin, TX, USA. Analytical Chemistry
(2005), 77(6), 1761-1770. Publisher: American Chemical Society, CODEN: ANCHAM ISSN: 0003-2700. Journal written in English.
Abstract
For detection and differentiation of isomeric flavonoids, electrospray ionization mass spectrometry is used to generate silver
complexes of the type (Ag + flavonoid)+. Collisionally activated dissocn. (CAD) of the resulting 1:1 silver/flavonoid complexes allows
isomer differentiation of flavonoids. Eighteen flavonoid diglycosides constituting seven isomeric series are distinguishable from each
other based on the CAD patterns of their silver complexes. Characteristic dissocn. pathways allow identification of the site of
glycosylation, the type of disaccharide (rutinose vs. neohesperidose), and the type of aglycon (flavonol vs. flavone vs. flavanone).
This silver complexation method is more universal than previous metal complexation methods, as intense silver complexes are obsd.
even for flavonoids that lack the typical metal chelation sites. To demonstrate the feasibility of using silver complexation and tandem
mass spectrometry to characterize flavonoids in complex mixts., flavonoids extd. from grapefruit juice are sepd. by high-performance
liq. chromatog. and analyzed via a postcolumn complexation ESI-MS/MS strategy. Diagnostic fragmentation pathways of the silver
flavanone
complexes of the individual eluting flavonoids allow successful identification of the six flavonoids in the ext.
Answer 674:
Synthesis of maximaflavanone-A and its derivative. Alam, Sayed; Islam, Azizul; Das, Naresh Chandra. Department of
Chemistry, Bangladesh Institute of Technology, Rajshahi, Bangladesh. Journal of Bangladesh Academy of Sciences (2004),
28(2), 117-120. Publisher: Bangladesh Academy of Sciences, CODEN: JBACDF ISSN: 0378-8121. Journal written in English.
Abstract
Maximaflavanone-A, {4,6-γ,γ-dimethylallyl-2",2"-dimethylpyrano(6",5":7,8)flavanone} along with its flavone deriv. were synthesized.

The synthesized compds. were characterized using UV, IR and 1H NMR spectral data.
Answer 675:
Quantitative structure-antioxidant activity relationships of flavonoid compounds. Farkas, Orsolya; Jakus, Judit; Heberger,
Karoly. Bio-oxidation Group, Chemical Research Center, Hungarian Academy of Sciences, Budapest, Hung. Molecules (2004),
9(12), 1079-1088. Publisher: Molecular Diversity Preservation International, CODEN: MOLEFW ISSN: 1420-3049.
http://www.mdpi.org/molecules/papers/91201079.pdf Journal; Online Computer File written in English. CAN 142:348110 AN
Abstract
A quant. structure-antioxidant activity relationship (QSAR) study of 36 flavonoids was performed using the partial least squares
projection of latent structures (PLS) method. The chem. structures of the flavonoids have been characterized by constitutional
descriptors, two-dimensional topol. and connectivity indexes. Our PLS model gave a proper description and a suitable prediction of the
antioxidant activities of a diverse set of flavonoids having clustering tendency.
Answer 676:
In silico prediction of receptor-mediated environmental toxic phenomena - Application to endocrine disruption. Lill, M. A.;
Dobler, M.; Vedani, A. Biographics Laboratory 3R, Basel, Switz. SAR and QSAR in Environmental Research (2005), 16(1-2),
149-169. Publisher: Taylor & Francis Ltd., CODEN: SQERED ISSN: 1062-936X. Journal written in English. CAN 143:21052 AN
Abstract
It is an objective of our institution to establish a virtual lab. allowing for a reliable in silico estn. of the harmful effects triggered by
drugs, chems. and their metabolites. In the recent past, we have developed the underlying technol. (Multi-dimensional QSAR: Quasar
and Raptor) and compiled a pilot system including the 3D models of three receptors known to mediate endocrine-disrupting effects (the
aryl hydrocarbon receptor, the estrogen receptor and the androgen receptor, resp.) and validated them against 310 compds. (drugs,
chems., toxins). Within this set up we could demonstrate that our concepts are able to both recognize toxic compds. substantially
flavanone
different from those used in the training set as well as to classify harmless compds. clearly as being non-toxic. This suggests that our
approach can be used for the prediction of adverse effects of drug mols. and chems.
Answer 677:
Synthesis of flavanones using nanocrystalline MgO. Choudary, B. M.; Ranganath, K. V. S.; Yadav, Jagajit; Kantam, M.
Lakshmi. Inorganic Chemistry Division, Indian Institute of Chemical Technology, Hyderabad, India. Tetrahedron Letters (2005),
46(8), 1369-1371. Publisher: Elsevier B.V., CODEN: TELEAY ISSN: 0040-4039. Journal written in English. CAN 142:336154
Abstract
The design and development of a truly nano heterogeneous catalyst for the Claisen-Schmidt condensation (CSC) of benzaldehydes
with 2-hydroxyacetophenone to yield substituted chalcones followed by isomerization to afford flavanones with excellent yields and
selectivity is described.
Answer 678:
Anti-inflammatory effect of heme oxygenase 1: Glycosylation and nitric oxide inhibition in macrophages. Lin, Hui-Yi; Shen,
Shing-Chuan; Chen, Yen-Chou. Graduate Institute of Pharmaceutical Sciences, School of Pharmacy, Taipei Medical University,
Taipei, Taiwan. Journal of Cellular Physiology (2004), Volume Date 2005, 202(2), 579-590. Publisher: Wiley-Liss, Inc., CODEN:
JCLLAX ISSN: 0021-9541. Journal written in English. CAN 142:309475 AN 2005:82225 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
Flavonoids including the aglycons, hesperetin (HT; 5,7,3'-trihydroxy-4'-methoxy-flavanone), and naringenin (NE; 5,7,4'-trihydroxy
flavanone) and glycones, hesperidin (HD; 5,7,3'-trihydroxy-4'-methoxy-flavanone 7-rhamnoglucoside) and naringin (NI;
5,7,4'-trihydroxy flavanone 7-rhamnoglucoside), were used to examine the importance of rutinose at C7 on the inhibitory effects of
flavonoids on lipopolysaccharide (LPS)-induced nitric oxide prodn. in macrophages. Both HT and NE, but not their resp. glycosides HD
and NI, induced heme oxygenase 1 (HO-1) protein expression in the presence or absence of LPS and showed time and dose-dependent
inhibition of LPS-induced nitric oxide (NO) prodn. and inducible nitric oxide synthase (iNOS) expression in RAW264.7, J774A.1, and
thioglycolate-elicited peritoneal macrophages. Additive inhibitory effect of an HO-1 inducer hemin and NE or NI on LPS-induced NO
prodn. and iNOS expression was identified, and HO enzyme inhibitor tin protoporphyrin (SnPP) attenuated the inhibitory effects of HT,
NE, and hemin on LPS-induced NO prodn. Both NE and HT showed no effect on iNOS mRNA and protein stability in RAW264.7 cells.
Removal of rutinose at C7 of HD and NI by enzymic digestion using hesperidinase (HDase) and naringinase (NIase) produce inhibitory
activity on LPS-induced NO prodn., according to the prodn. of the aglycons, HT and NE, by high-performance liq. chromatog. (HPLC)
anal. Furthermore, the amt. of NO produced by LPS or lipoteichoic acid (LTA) was significantly reduced in HO-1-overexpressing cells
(HO-1/RAW264.7) compared to that in parental cells (RAW264.7). Results of the present study provide scientific evidence to suggest
that rutinose at C7 is a neg. moiety in flavonoid inhibition of LPS-induced NO prodn., and that HO-1 is involved in the inhibitory
mechanism of flavonoids on LPS-induced iNOS and NO prodn.
Answer 679:
flavanone
Utilization of the genetic resources of wild species to create a nontransgenic high flavonoid tomato. Willits, Michael G.;
Kramer, Catherine M.; Prata, Rogerio T. N.; De Luca, Vincenzo; Potter, Brian G.; Steffens, John C.; Graser, Gerson. Syngenta
Biotechnology, Inc., Research Triangle Park, NC, USA. Journal of Agricultural and Food Chemistry (2005), 53(4), 1231-1236.
Abstract
The authors describe for the first time a nontransgenic metabolic engineering approach to developing a high flavonoid tomato using a
wild tomato species (Lycopersicon pennellii v. puberulum) and demonstrate the opportunities for restoring functional pathways using
the genetic resources of wild species, resulting in prodn. of healthier foods.
Answer 680:
Antimicrobial and radical scavenging flavonoids from the stem wood of Erythrina latissima. Chacha, Musa; Bojase-Moleta,
Gomotsang; Majinda, Runner R. T. Department of Chemistry, University of Botswana, Gaborone, Botswana. Phytochemistry
(Elsevier) (2005), 66(1), 99-104. Publisher: Elsevier B.V., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN
Abstract
From the stem wood of Erythrina latissima, two isoflavones and a flavanone were isolated and characterized as
7,3'-dihydroxy-4'-methoxy-5'-(γ,γ-dimethylallyl)isoflavone (erylatissin A, I), 7,3'-dihydroxy-6'',6''-dimethyl-4'',5''-dehydropyrano[2'',3'':
4',5']isoflavone (erylatissin B, II), (-)-7,3'-dihydroxy-4'-methoxy-5'-(γ,γ-dimethylallyl)flavanone (erylatissin C, III), resp., in addn. to 10
known flavonoids. Structures of these compds. were detd. on the basis of their spectroscopic data. These compds. showed
antimicrobial activity against Escherichia coli, Staphylococcus aureus, Bacillus subtilis and Candida mycoderma. The isolated
compds. also exhibited weak radical scavenging properties towards DPPH radical.
flavanone
HO O
OH
O
OMe
Me Me I
HO O
OH
O
O
Me
Me II
OH
OMe
HO O
Me
O Me III
Answer 681:
Synthesis of 5,7-dihydroxy-6,8-di-C-prenyl-4'-O-prenyl-flavanone. Hossain, M. Amzad; Saravanand; Ismail, Zhari. School of

Pharmaceutical Sciences, University Sains Malaysia, Pulau Pinang, Malay. Pakistan Journal of Scientific and Industrial Research
(2004), 47(5), 332-335. Publisher: Pakistan Council of Scientific and Industrial Research, CODEN: PSIRAA ISSN: 0030-9885.
Abstract
The prenylated flavanone was synthesized from phloroacetophenone. All the new products were characterized by the spectral data and
microanal.
flavanone
Answer 682:
Heterogeneous catalytic synthesis of flavanones: an investigation of the functional group substitution effects, kinetics, and
reaction mechanism. Hargrove, Sirena Colletta. Univ. of South Carolina, Columbia, SC, USA. Avail. UMI, Order No.
DA3115113. (2003), 120 pp. From: Diss. Abstr. Int., B 2004, 64(12), 6201. Dissertation written in English. CAN 143:172427
Answer 683:
Compositions for manipulating the lifespan and stress response of cells and organisms. Sinclair, David A.; Howitz, Konrad
T.; Zipkin, Robert E. (President and Fellows of Harvard College, USA; Biomol International L.P.). PCT Int. Appl. (2005), 224 pp.
KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU,
SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE,
CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG.
Patent written in English. Application: WO 2004-US21465 20040701. Priority: US 2003-483949 20030701; US 2003-532158

WO 2005002672 A2 20050113 WO 2004-US21465 20040701
WO 2005002672 A3 20051110
ZW
AU 2004253579 A1 20050113 AU 2004-253579 20040701
CA 2529510 A1 20050113 CA 2004-2529510 20040701
US 20060084135 A1 20060420 US 2004-884062 20040701
EP 1648437 A2 20060426 EP 2004-777536 20040701
JP 2007530417 T 20071101 JP 2006-518817 20040701
JP 2007326872 A 20071220 JP 2007-203287 20070803
US 2003-483949P P 20030701
US 2003-532158P P 20031223
flavanone
WO 2004-US21465 W 20040701
JP 2006-518817 A3 20040701
Abstract
apoptosis; lifespan and sensitivity to stress of cells and organisms. Exemplary methods comprise contacting a cell with an activating
as a sphingolipid, e.g., sphingosine.
Answer 684:
Compositions for manipulating the lifespan and stress response of cells and organisms. Sinclair, David A. (President and
Fellows of Harvard College, USA). PCT Int. Appl. (2005), 223 pp. CODEN: PIXXD2 WO 2005002555 A2 20050113
EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD,
MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ,
UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC,
NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2004-US21479
20040701. Priority: US 2003-483949 20030701; US 2003-532158 20031223. CAN 142:127622 AN 2005:29182 CAPLUS

WO 2005002555 A2 20050113 WO 2004-US21479 20040701
WO 2005002555 A3 20051103
ZW
US 20060084135 A1 20060420 US 2004-884062 20040701
JP 2007326872 A 20071220 JP 2007-203287 20070803
US 2003-483949P P 20030701
US 2003-532158P P 20031223
JP 2006-518817 A3 20040701
Abstract
flavanone
apoptosis, lifespan and sensitivity to stress of cells and organisms. Exemplary methods comprise contacting a cell with an activating
as a sphingolipid, e.g., sphingosine. It is shown that sirtuin activators mimic calorie restriction and delay aging in metazoans.
Answer 685:
Some flavonoids and DHEA-S prevent the cis-effect of expanded CTG repeats in a stable PC12 cell transformant. Furuya,
Hirokazu; Shinnoh, Nobue; Ohyagi, Yasumasa; Ikezoe, Koji; Kikuchi, Hitoshi; Osoegawa, Manabu; Fukumaki, Yasuyuki; Nakabeppu,
Yusaku; Hayashi, Toshimitsu; Kira, Jun-ichi. Department of Neurology, Neurological Institute, Graduate School of Medical Sciences,
Kyushu University, Fukuoka, Japan. Biochemical Pharmacology (2005), 69(3), 503-516. Publisher: Elsevier B.V., CODEN:
BCPCA6 ISSN: 0006-2952. Journal written in English. CAN 142:273870 AN 2005:28043 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
Expanded CUG triplet repeats carrying mRNA seem to be responsible for myotonic dystrophy type 1 (DM1). To study the
pathogenesis of DM1, we constructed a DM1 cell culture model using a PC12 neuronal cell line and screened flavonoids that ameliorate
this mRNA gain of function. The expanded 250 CTG repeat was subcloned into the 3'-untranslated region of the luciferase gene
yielding a stable transformant of PC12 (CTG-250). The cytotoxicity of CTG-250 was evaluated by intracellular LDH activity, and the
cis-effect by luciferase activity. To find agents that alter CTG-250 toxic effects, 235 bioflavonoids were screened. An increased
cis-effect and cytotoxicity were found when CTG-250 was treated with nerve growth factor to induce differentiation. Western blotting
with anti-caspase-3 antibody suggested that cell death was caused by apoptosis. Screening anal. confirmed that a flavone (toringin),
an isoflavones (genistein and formononetin), a flavanone (isosakuranetin), and DHEA-S prevent both the cytotoxicity and cis-effect of
CTG-250 and that a flavanone (naringenin), isoflavone (ononin), and xanthylatin strongly inhibit the cis-effect of CTG repeats. In
conclusion, we found that this neuronal cell line, which expresses the CUG repeat-bearing mRNA, showed cis-effects through the
reporter gene and neuronal death after cell differentiation in vitro. However, some flavonoids and DHEA-S inhibit both the cis-effect
and cytotoxicity, indicating that their chem. structures work to ameliorate both these toxic effects. This system makes it easy to
evaluate the toxic effects of expanded CTG repeats and therefore should be useful for screening other DM1 treatments for their
efficacies.
Answer 686:
A novel nonradioactive method for measuring aromatase activity using a human ovarian granulosa-like tumor cell line and
an estrone ELISA. [Erratum to document cited in CA142:033083]. Ohno, Ken; Araki, Naohiro; Yanase, Toshihiko; Nawata,
Hajime; Iida, Mitsuru. EcoScreen R & D Section, Endocrine Disrupting Chemical Analysis Center, Otsuka Life Science Initiative,
Otsuka Pharmaceutical Co., Ltd., Kawauchi-cho, Tokushima, Japan. Toxicological Sciences (2005), 83(2), 406. Publisher: Oxford
University Press, CODEN: TOSCF2 ISSN: 1096-6080. Journal written in English. CAN 143:399952 AN 2005:24206 CAPLUS
Abstract
On page 448, Results section, "Reproducibility of this Aromatase Assay" subheading, sentence 1 should read: "The intra-assay
reproducibility of the system was evaluated by calculation of coefficients of variation (CV), where CV = 100% × SD/mean.". Sentence
3 should read: "Inter-assay reproducibility in the aromatase assay was determined by comparing the IC50's calculated for each of the
triplicate dose-response curves for 4-OHA and imazalil, which were chosen because their inhibitory effects covered a wide
concentration range.".
flavanone
Answer 687:
Flavonoids and Cardiovascular Disease. Gross, Myron. Molecular Epidemiology and Biomarker Research Laboratory,
Department of Laboratory Medicine and Pathology, School of Medicine, Division of Epidemiology, School of Public Health, University
of Minnesota, Minneapolis, MN, USA. Pharmaceutical Biology (Lisse, Netherlands) (2004), 42(Suppl.), 21-35. Publisher: Taylor &
Francis The Netherlands, CODEN: PHBIFC ISSN: 1388-0209. Journal; General Review written in English. CAN 142:384781 AN
Abstract
A review. Diets high in flavonoids have long been assocd. with nutritional recommendations, a healthy lifestyle, and the prevention of
chronic diseases. However, identification of specific beneficial effects from specific flavonoids and flavonoid-rich foods has been a
challenging area, probably due to a nonessential or conditional role for flavonoids in human nutrition. Nonetheless, recent efforts in the
area of high flavonoid-contg. foods and cardiovascular disease have begun providing the first demonstrations of specific effects and
mechanisms of action in well-controlled studies. The early studies have shown that flavonoids have several anti-atherosclerotic
activities including anti-inflammatory, antioxidant, antiproliferative, antiplatelet, and provessel function activities. Cholesterol-lowering
and antihypertensive effects of flavonoids have been studied and appear minimal in humans. The studies also demonstrate several
possible mechanisms and pleiotropic effects of flavonoids that may be active in redn. in the risk of cardiovascular disease. Several
subclasses of flavonoids may contribute toward the apparent beneficial effects and include flavones, flavonols, flavanones,
catechins isoflavones, proanthocyanidins, and anthocyanidins. Further studies are necessary for confirmation of the beneficial
effects, identification of dose-response relationships, and identification the most bioactive flavonoids.
Answer 688:
Preparation of rutin esters of flavonoids with ω-substituted C6-C22 fatty acids and used in cosmetics as skin protectors
against damages due to UV-radiation. Moussou, Philippe; Falcimaigne, Aude; Ghoul, Mohamed; Danous, Louis; Pauly, Gilles.
(Cognis France S.A., Fr.). PCT Int. Appl. (2005), 32 pp. CODEN: PIXXD2 WO 2005000831 A1 20050106 Designated States
W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES,
FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW,
MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ,
VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR,
BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2004-EP6281 20040611.
Priority: EP 2003-13899 20030620. CAN 142:94063 AN 2005:14387 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))

WO 2005000831 A1 20050106 WO 2004-EP6281 20040611
ZW
flavanone
EP 1636204 A1 20060322 EP 2004-739782 20040611

R: DE, ES, FR, GB, IT
JP 2007516937 T 20070628 JP 2006-515885 20040611
US 20070184098 A1 20070809 US 2006-561551 20061221
EP 2003-13899 A 20030620
WO 2004-EP6281 W 20040611
Abstract
The invention refers to esters of flavonoids such as flavones, flavonols, flavanones, flavanols, flavanolols, isoflavones,
anthocyanins, proanthocyanidins, chalcones, aurones and hydroxycoumarins conjugated by an ester bond to an ω substituted C6-C22
fatty acid. These flavonoid derivs. exhibit excellent skin protecting properties esp. against damages due to UV-radiation. They show
very good chem. stability and are easily incorporated into cosmetic and pharmaceutical formulations.
Answer 689:
Separating agent for optical isomers, method of production thereof, and separation column for optical isomers. Okamoto,
Yoshio; Yamamoto, Chiyo; Bezhan, Chankvetadze. (Japan). U.S. Pat. Appl. Publ. (2004), 19 pp. CODEN: USXXCO US
2004262229 A1 20041230 Patent written in English. Application: US 2004-854244 20040527. Priority: JP 2003-155414
20030530; JP 2004-16952 20040126. CAN 142:93183 AN 2005:784 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))

US 20040262229 A1 20041230 US 2004-854244 20040527
JP 2005017268 A 20050120 JP 2004-16952 20040126
EP 1500430 A2 20050126 EP 2004-12766 20040528
EP 1500430 A3 20060524
JP 2003-155414 A 20030530
JP 2004-16952 A 20040126
Abstract
The present invention provides a sepg. agent for optical isomers having a porous monolithic inorg. type carrier and polysaccharide or a
deriv. thereof supported on the monolithic inorg. type carrier, and a sepn. column for optical isomers in which the sepg. agent for
optical isomers is held in a column tube. According to the invention, the sepg. agent for optical isomers and the sepn. column for
flavanone
optical isomers which have high asymmetry recognition ability and can be used particularly at a high flow rate when used for the sepn.
of optical isomers is provided. Thus, cellulose tris(3,5-dimethylphenylcarbamate) or amylose tris(3,5-dimethylphenylcarbamate) was
supported on a monolithic inorg. type porous body and used to sep. a variety of substances into their individual enantiomers by HPLC.
The inorg. porous body allows higher pressure to be applied during the loading of the stationary phase, resulting in higher doping and
increased sepn. of optical isomers.
Answer 690:
Flavanone compound and uses thereof. Kumazawa, Shigenori; Nakayama, Tsutomu; Shimoi, Kayoko; Goto, Takaki; Fukumoto,
Syuichi; Arakaki, Tsutomu. (Pokka Corporation, Japan). PCT Int. Appl. (2004), 46 pp. CODEN: PIXXD2 WO 2004113318 A1
20041229 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE,
DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV,
MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR,
TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT,
LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in Japanese. Application: WO
2004-JP8964 20040618. Priority: JP 2003-177333 20030620; JP 2003-177332 20030620; JP 2004-123480 20040419; JP

WO 2004113318 A1 20041229 WO 2004-JP8964 20040618
DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, KE, KG, KP, KR, KZ, LC,
LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO,
RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW
JP 2005029560 A 20050203 JP 2004-123479 20040419
JP 2005029778 A 20050203 JP 2004-123480 20040419
AU 2004249614 A1 20041229 AU 2004-249614 20040618
AU 2004249614 B2 20080403
EP 1640371 A1 20060329 EP 2004-746433 20040618
HU, PL, SK
CN 1809551 A 20060726 CN 2004-80017013 20040618
CN 101130536 A 20080227 CN 2007-10152920 20040618
US 20060292204 A1 20061228 US 2005-562019 20051219
US 7256214 B2 20070814
US 20070161579 A1 20070712 US 2007-686038 20070314
JP 2003-177332 A 20030620
JP 2003-177333 A 20030620
JP 2004-123479 A 20040419
flavanone
JP 2004-123480 A 20040419
WO 2004-JP8964 W 20040618
CN 2004-80017013 A3 20040618
US 2005-562019 A3 20051219
Abstract
An antioxidant, antibacterial, antitumor agent, food or beverage, cosmetic, quasi-drug prepn., and medical product which each contains
the novel flavanone compd. represented by the following structural formula. Alternatively, the antioxidant, antibacterial, antitumor
agent, food or beverage, cosmetic, quasi-drug prepn., and medical product each contains at least one flavanone compd. selected
among nymphaeol-A, nymphaeol-B, and nymphaeol-C. Structural formula (I).
OH
OH
Me
HO O
CH 2 CH C ( CH 2 ) 2 CH C Me
Me
OH O I
Answer 691:
Novel methods to extract flavanones and xanthones from the root bark of Maclura pomifera. Teixeira, D. Martins; Teixeira da
Costa, C. CLAV Rua Romao Ramalho n° 59, Departamento de Quimica, Universidade de Evora, Evora, Port. Journal of
Chromatography, A (2005), 1062(2), 175-181. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in
Abstract
A comparison between the extn. yields of xanthones and flavanones from the root bark of the Maclura pomifera by solid-liq. extn.
(SLE), matrix solid phase dispersion (MSPD), and an alternative method using sea sand as a sample disruptor, is presented here. Two
extn. solvents were used for all extn. techniques, dichloromethane and methanol:water, (9:1, vol./vol.). The extn. procedures were
reproducible as the R.S.D. values were less than 5% for almost all compds. A recovery above 80% was obtained for macluraxanthone
using the sea sand extn. procedure. Statistical treatment, ANOVA-single factor, was used to evaluate the different extn. procedures,
and homogenization of plant material with sand followed by elution with dichloromethane provided the most efficient and rapid extn.
method.
Answer 692:
Oral Silibinin Inhibits Lung Tumor Growth in Athymic Nude Mice and Forms a Novel Chemocombination with Doxorubicin
flavanone
Targeting Nuclear Factor κB-Mediated Inducible Chemoresistance. Singh, Rana P.; Mallikarjuna, G. U.; Sharma, Girish;
Dhanalakshmi, Sivanandhan; Tyagi, Anil K.; Chan, Daniel C. F.; Agarwal, Chapla; Agarwal, Rajesh. Department of Pharmaceutical
Sciences, School of Pharmacy, University of Colorado Health Sciences Center, Denver, CO, USA. Clinical Cancer Research
(2004), 10(24), 8641-8647. Publisher: American Association for Cancer Research, CODEN: CCREF4 ISSN: 1078-0432. Journal
Abstract
The acute and cumulative dose-related toxicity and drug resistance, mediated via nuclear factor κB (NFκB), of anthracycline
anticancer drugs pose a major problem in cancer chemotherapy. Here, we report that oral silibinin (a flavanone) suppresses human
non-small-cell lung carcinoma A549 xenograft growth (P = 0.003) and enhances the therapeutic response (P < 0.05) of doxorubicin in
athymic BALB/c nu/nu mice together with a strong prevention of doxorubicin-caused adverse health effects. Immunohistochem.
analyses of tumors showed that silibinin and doxorubicin decrease (P < 0.001) proliferation index and vasculature and increase (P <
0.001) apoptosis; these effects were further enhanced (P < 0.001) in combination treatment. Pharmacol. dose of silibinin (60 μmol/L)
achieved in animal study was biol. effective (P < 0.01 to 0.001, growth inhibition and apoptosis) in vitro in A549 cell culture together
with an increased efficacy (P < 0.05 to 0.001) in doxorubicin (25 nmol/L) combination. Furthermore, doxorubicin increased NFκB DNA
binding activity as one of the possible mechanisms for chemoresistance in A549 cells, which was inhibited by silibinin in combination
treatment. Consistent with this, silibinin inhibited doxorubicin-caused increased translocation of p65 and p50 from cytosol to nucleus.
Silibinin also inhibited cyclooxygenase-2, an NFκB target, in doxorubicin combination. These findings suggest that silibinin inhibits in
vivo lung tumor growth and reduces systemic toxicity of doxorubicin with an enhanced therapeutic efficacy most likely via an
inhibition of doxorubicin-induced chemoresistance involving NFκB signaling.
Answer 693:
The interaction of flavonoids with membranes: potential determinant of flavonoid antioxidant effects. Erlejman, A. G.;
Verstraeten, S. V.; Fraga, C. G.; Oteiza, P. I. Department of Biological Chemistry-IQUIFIB (UBA-CONICET); School of Pharmacy
and Biochemistry, University of Buenos Aires, Argent. Free Radical Research (2004), 38(12), 1311-1320. Publisher: Taylor &
Francis Ltd., CODEN: FRARER ISSN: 1071-5762. Journal written in English. CAN 142:348946 AN 2004:1149813 CAPLUS
Abstract
Twenty six phenolic substances including representatives of the families, flavanones, flavanols and procyanidins, flavonols,
isoflavones, phenolic acids and phenylpropanones were investigated for their effects on lipid oxidn., membrane fluidity and membrane
integrity. The incubation of synthetic phosphatidylcholine (PC) liposomes in the presence of these phenolics caused the following
effects: (a) flavanols, their related procyanidins and flavonols were the most active preventing 2,2'-azo-bis (2,4-dimethylvaleronitrile)
(AMVN)-induced 2-thiobarituric acid-reactive substances (TBARS) formation, inducing lipid ordering at the water-lipid interface, and
preventing Triton X-100-induced membrane disruption; (b) all the studied compds. inhibited lipid oxidn. induced by the water-sol. oxidant
2,2'-azo-bis (2-amidinopropane) (AAPH), and no family-related effects were obsd. The protective effects of the studied phenolics on
membranes were mainly assocd. to the hydrophilicity of the compds., the degree of flavanol oligomerization, and the no. of hydroxyl
groups in the mol. The present results support the hypothesis that the chem. structure of phenolics conditions their interactions with
membranes. The interactions of flavonoids with the polar head groups of phospholipids, at the lipid-water interface of membranes,
should be considered among the factors that contribute to their antioxidant effects.
Answer 694:
The Differential Tissue Distribution of the Citrus Flavanone Naringenin Following Gastric Instillation. El Mohsen, Manal
flavanone
Abd; Marks, Joanne; Kuhnle, Gunter; Rice-Evans, Catherine; Moore, Kevin; Gibson, Glenn; Debnam, Edward; Srai, S. Kaila.
Antioxidant Research Group, Wolfson Centre for Age-Related Diseases, GKT School of Biomedical Sciences, Kings College London,
London, UK. Free Radical Research (2004), 38(12), 1329-1340. Publisher: Taylor & Francis Ltd., CODEN: FRARER ISSN:
Abstract
Citrus flavonoids have been investigated for their biol. activity, with both anti-inflammatory and -carcinogenic effects being reported.
However, little information is known on the bioavailability of these compds. in vivo. The objectives of this study were to det. the
tissue distribution of naringenin after gastric gavage of [3H]-naringenin to rats. Unlabeled naringenin was also used to quantify the
levels of naringenin and its major metabolites in tissues and eliminated in the urine and feces. Significant radioactivity was detected in
the plasma as well as all tissues examd. 2 h post-gavage. After 18 h, higher levels of radioactivity were retained in plasma and
tissues (55% of the administered radioactivity). Investigation of the nature of metabolites, using unlabeled naringenin, revealed that
the glucuronides were the major components in plasma, tissues and urine, in addn. to the colonic metabolite 3-(4-hydroxyphenyl)
propionic acid, detected in the urine. The aglycon was the form extensively retained in tissues after 18 h post-gavage. Total identified
metabolites detected after 18 h in most tissues were only 1-5% of the levels detected after 2 h. However, the brain, lungs and heart
retained 27, 20 and 11%, resp., relative to the total metabolites detected at 2 h. While radioactive detection suggests increased levels
of breakdown products of naringenin after 18 h vs. 2 h, the products identified using unlabeled naringenin are not consistent with this,
suggesting that a predominant proportion of the naringenin breakdown products at 18 h are retained as smaller decompn. mols. which
cannot yet be identified.
Answer 695:
Expression of anthocyanin biosynthesis genes in the skin of peach and nectarine fruit. Tsuda, Tomomi; Yamaguchi,
Masami; Honda, Chikako; Moriguchi, Takaya. Japan Society for the Promotion of Science, Japan. Journal of the American
Society for Horticultural Science (2004), 129(6), 857-862. Publisher: American Society for Horticultural Science, CODEN: JOSHB5
SciFinder (R))
Abstract
We used RNA blot anal. to examine the expression of six genes of the anthocyanin biosynthesis pathway in the flowers and fruit skins
at three developmental stages of white and red peaches and a deep-red nectarine [Prunus persica (L.) Batch]. In the red peach
'Akatsuki' and the deep-red nectarine 'Flavortop', expression levels of anthocyanin biosynthesis genes were related to anthocyanin
accumulation in the fruit skin; expression of all six genes dramatically increased at Stage III of fruit development, and anthocyanin
concn. also increased at this stage. In the white peach 'Mochizuki', however, expression of the chalcone synthase gene (CHS) and the
dihydroflavonol 4-reductase gene (DFR) was undetectable in Stage III, although the chalcone isomerase gene (CHI), the flavanone
3-hydroxylase gene (F3H), the anthocyanidin synthase gene (ANS), and the UDP-glucose-flavonoid 3-O-glucosyltransferase gene
(UFGT) were expressed. We occasionally found red pigment in the skin of 'Mochizuki' peach. In these red skin areas, both CHS and
DFR were clearly expressed in Stage III. These results suggest that CHS and DFR are the key regulatory genes in the process of
anthocyanin biosynthesis in mature red peach and nectarine.
Answer 696:
Phytoestrogens in cancer prevention: Characterization and beneficial effects of kurarinone, a new flavanone and a major
phytoestrogen constituent of Sophora flavescens Ait. De Naeyer, A.; Vanden Berghe, W.; De Keukeleire, D.; Haegeman, G.
Ghent University, Ghent, Belg. Editor(s): Bagchi, Debasis; Preuss, Harry G. Phytopharmaceuticals in Cancer Chemoprevention
flavanone
(2005), 427-448. Publisher: CRC Press LLC, Boca Raton, Fla CODEN: 69GGT2 Conference written in English. CAN 143:25797
Abstract
The biol. effects and potential health benefits of phytoestrogens are outlined. The focus is on the isolation and characterization of
kurarinone from Sophora flavescens legume plant. Kurarinone was extd. from dried ground plant material, tested in vitro for
estrogenic, cell proliferation, and anticancer effects, and was chem. characterized by 1H-NMR, 13C-NMR, and other techniques.
Kurarinone holds promise as a prophylactic compd. that may have beneficial effects in the treatment of various postmenopausal
disturbances and neoplastic disorders.
Answer 697:
cDNA microarray analysis of developing grape (Vitis vinifera cv. Shiraz) berry skin. Waters, Daniel L. E.; Holton, Timothy A.;
Ablett, Effie M.; Lee, L. Slade; Henry, Robert J. Centre for Plant Conservation Genetics, Southern Cross University, Lismore,
Australia. Functional & Integrative Genomics (2005), 5(1), 40-58. Publisher: Springer GmbH, CODEN: FIGUBY ISSN: 1438-793X.
Abstract
Microarray anal. of Vitis vinifera cv. Shiraz developing berries has revealed the expression patterns of several categories of genes.
Microarray slides were constructed from 4608 PCR-amplified cDNA clones derived from a ripening grape berry cDNA library. The
mRNA expression levels of the genes represented by these cDNAs were measured in flowers, week 2 post-flowering whole berries,
week 5, week 8, week 10 (veraison, green berries), week 12 and week 13 berry skin. In addn., a comparison of RNA expression in
pigmented and unpigmented berry skin at veraison (week 10) was undertaken. Image and statistical anal. revealed four sets of genes
with distinctive and similar expression profiles over the course of berry development. The first set was composed of genes which had
max. RNA expression in flowers, followed by a steady decrease in expression. The most prominent group within this set were genes
which have a role in photosynthesis. The second set of cDNAs was dominated by genes involved in flavonoid biosynthesis and had a
peak of expression week 2 post-flowering. The data indicate coordinate regulation of flavonoid biosynthetic genes which code for the
enzymes 4-coumarate-CoA ligase, chalcone synthase, chalcone isomerase, flavanone hydroxylase, anthocyanidin reductase and
cytochrome b5. The third set of cDNAs exhibited max. expression week 5 post-flowering, midway between flowering and veraison, a
period of rapid berry growth. This set of cDNAs is dominated by genes which code for structural cell wall proteins. The fourth set of
genes was dramatically up-regulated at veraison and remained up-regulated until 13 wk post-flowering. This set of genes was
composed of a diverse range of genes, a reflection of the complexity of ripening, most with no known function.
Answer 698:
New flavanone and chalcone glucosides from Bidens bipinnata Linn. Li, Shuai; Kuang, Hai-Xue; Okada, Yoshihito; Okuyama,
Toru. Institute of Materia Medica, Peking Union Medical College, Chinese Academy of Medical Sciences, Beijing, Peop. Rep.
China. Journal of Asian Natural Products Research (2005), 7(1), 67-70. Publisher: Taylor & Francis Ltd., CODEN: JANRFI ISSN:
Abstract
A new flavanone glucoside, bidenoside F (I), and a new chalcone glucoside, bidenoside G (II), along with the known compd. iso-okanin
7-O-(4'',6''-diacetyl)-β-D-glucopyranoside have been isolated from the aerial parts of Bidens bipinnata L. The structures were detd. on
flavanone
the basis of spectroscopic methods.
OH
OH
AcO CH 2 OH
O O O
OAc
OH
OH
O I
OH
OH
AcO CH 2
O O OH
OH
OH
OH
O II
Answer 699:
an estrone ELISA. [Erratum to document cited in CA142:033083]. Ohno, Ken; Araki, Naohiro; Yanase, Toshihiko; Nawata,
Hajime; Iida, Mitsuru. EcoScreen R & D Section, Endocrine Disrupting Chemical Analysis Center, Otsuka Life Science Initiative,
Otsuka Pharmaceutical Co., Ltd., Kawauchi-cho, Tokushima, Japan. Toxicological Sciences (2005), 83(1), 204. Publisher: Oxford
University Press, CODEN: TOSCF2 ISSN: 1096-6080. Journal written in English. CAN 143:319235 AN 2004:1070107
Abstract
In Discussion, paragraph 4, the following sentence should have read, "In TBT, the reduction of aromatase activity was also observed,
however the cell viability was declined in parallel.". There are no Supplementary Data for this article.
Answer 700:
Silica gel-supported InBr3 and InCl3: new catalysts for the facile and rapid oxidation of 2'-hydroxychalcones and flavanones
to their corresponding flavones under solvent free conditions. Ahmed, Naseem; Ali, Hasrat; van Lier, Johan E. Department
of Nuclear Medicine and Radiobiology, Faculty of Medicine, Universite de Sherbrooke, Sherbrooke, QC, Can. Tetrahedron Letters
(2005), 46(2), 253-256. Publisher: Elsevier B.V., CODEN: TELEAY ISSN: 0040-4039. Journal written in English. CAN
flavanone
Abstract
Silica gel supported InBr3 or InCl3 were explored as a solid-support catalysts for the facile and efficient oxidn., under solvent free
conditions, of 2'-hydroxychalcones and flavanones to yield flavones, e.g., I, in good yield. The catalysts were easily prepd., stable,
and efficient under mild reaction conditions.
MeO OMe
O I
Answer 701:
Non-empirical assignment of the absolute configuration of (-)-naringenin, by coupling the exciton analysis of the circular
dichroism spectrum and the ab initio calculation of the optical rotatory power. Giorgio, Egidio; Parrinello, Nunziatina;
Caccamese, Salvatore; Rosini, Carlo. Dipartimento di Chimica, Universita della Basilicata, Potenza, Italy. Organic &
Biomolecular Chemistry (2004), 2(24), 3602-3607. Publisher: Royal Society of Chemistry, CODEN: OBCRAK ISSN: 1477-0520.
Abstract
The non-empirical assignment of the abs. configuration of (-)-naringenin, the aglycon of (-)-naringin, a flavanone glycoside abundant in
the albedo of immature grapefruits and showing several interesting biol. properties, has been approached by two different methods: (a)
the exciton anal. of the CD spectrum and (b) the ab initio calcn. of the optical rotatory power. Both the methods indicate the
configurational correlation (-)/(S), as empirically suggested by Gaffield. A comparison of advantages and limitations of the two
methods of anal. is also presented.
Answer 702:
Preparation of ordered large pore SBA-15 silica functionalized with aminopropyl groups through one-pot synthesis.
Wang, Xueguang; Lin, Kyle S. K.; Chan, Jerry C. C.; Cheng, Soofin. Department of Chemistry, National Taiwan University, Taipei,
Taiwan. Chemical Communications (Cambridge, United Kingdom) (2004), (23), 2762-2763. Publisher: Royal Society of
Chemistry, CODEN: CHCOFS ISSN: 1359-7345. Journal written in English. CAN 142:134424 AN 2004:1037520 CAPLUS
Abstract
Highly ordered large pore SBA-15 silica functionalized with up to 16% aminopropyl groups was synthesized for the first time via
flavanone
co-condensation of tetra-Et orthosilicate (TEOS) and 3-aminopropyltriethoxysilane (APTES) using an amphiphilic block copolymer
(Pluronic 123) as the structure-directing agent. This silica gave high catalytic activity and selectivity toward flavanone synthesis
through aldol condensation and subsequent intramol. Michael addn. of benzaldehyde and 2-hydroxyacetophenone. The aldol
condensation of benzaldehyde with (1-(2-hydroxyphenyl)ethanone gave 1-(2-hydroxyphenyl)-3-phenyl-2-propen-1-one. The Michael
reaction of the latter then gave 2,3-dihydro-2-phenyl-4H-1-benzopyran-4-one (flavanone). The Knoevenagel reaction of (cyano)acetic
acid Et ester with benzaldehyde gave 2-cyano-3-phenyl-2-propenoic acid Et ester.
Answer 703:
Cytotoxicity and antiproliferative activities of several phenolic compounds against three melanocytes cell lines: relationship
between structure and activity. Yanez, Josefa; Vicente, Vicente; Alcaraz, Miguel; Castillo, Julian; Benavente-Garcia, Obdulio;
Canteras, Manuel; Lozano Teruel, Jose A. Department of Pathology, Faculty of Medicine, University of Murcia, Murcia, Spain.
Nutrition and Cancer (2004), 49(2), 191-199. Publisher: Lawrence Erlbaum Associates, Inc., CODEN: NUCADQ ISSN: 0163-5581.
Abstract
Polyphenolic compds. are widely distributed in the vegetable kingdom and are therefore consumed regularly in the human diet.
Epidemiol. studies suggest that foods rich in polyphenolic compds. contribute to reducing the risk of cancer. The purpose of our work
is to: 1) study the possible cytotoxicity and antiproliferative effects of 13 polyphenolic compds. on 3 cell lines of melanocytes, 2 of
melanoma (B16F10 and SK-MEL-1), and 1 of nontransformed melanocytes (Melan-a); and 2) identify the possible relationship between
the chem. structure of the tested compds. and their effect on cellular viability. The said polyphenolic compds. corresponded to 8
flavonoids with varying hydroxyl and methoxyl substituents, related structurally through the oxidn. state of their flavonoid skeleton, a
catechin polymer and 4 phenolic acids. The cytotoxic activity of all the studied compds. was modest or not apparent. The flavonoids
luteolin, tangeretin, baicalein, quercetin, and myricetin, and gallic acid showed antiproliferative effects on the tested lines. Our results
suggest that a correlation exists between the structural oxidn. state and the position, no., and nature of substituents of the
polyphenolic compds. studied and their antiproliferative effects.
Answer 704:
Oxidation and rearrangements of flavanones by mammalian cytochrome P450. Kagawa, H.; Takahashi, T.; Ohta, S.; Harigaya,
Y. Dep. Organic Synthesis, Sch. Pharm. Sci., Kitasato Univ., Minato-ku, Tokyo, Japan. Xenobiotica (2004), 34(9), 797-810.
Publisher: Taylor & Francis Ltd., CODEN: XENOBH ISSN: 0049-8254. Journal written in English. CAN 142:232287 AN
Abstract
To clarify the metabolic pathways of flavanones in mammals, the metab. of (±)-flavanone and (±)-4'-methoxyflavanone by rat liver
microsomes and recombinant human P450s in which structural changes are readily identifiable were examd. The β-NADP
(NADPH)-dependent formation of flavone plus (±)-2,3-trans-flavanonol and 4'-methoxyflavone plus
(±)-2,3-trans-4'-methoxyflavanoonol, resp., by rat liver microsomes was obsd. The same metabolites were generated by recombinant
human P450s in addn. to the formation of isoflavone from (±)-flavanone. The kinetic isotope effects in these reactions were examd.
using deuterated (±)-flavanone and (±)-4'-methoxyflavanone. There was a strong isotope effect in the prodn. of flavonols, but the
isotope effect in the prodn. of flavones was small. The results indicated that the P 450-mediated conversion of (±)-flavanone and of
(±)-4'-methoxyflavanone to the corresponding metabolites proceeded via abstraction of a hydrogen radical from the C-2- or
C-3-position of the flavanone skeleton. The antioxidant properties of flavanone and its metabolites were examd. by measuring
superoxide-scavenging activity in a xanthine-xanthine oxidase-cytochrome c system. (±)-2,3-Trans-Flavanonol had higher activity
flavanone
than that of other flavonoids. Flavanones are metabolized by mammalian P450s, providing important information relevant to the
metab. and pharmacol. action of dietary flavanones.
Answer 705:
Progress on antioxidant activation and extracting technology of flavonoids. Wang, Qiuan; Zhou, Bing; Shan, Yang.
Chemistry and Chemical Engineering University College, Hunan University, Changsha, Hunan, Peop. Rep. China. Huagong
Shengchan Yu Jishu (2004), 11(5), 29-32. Publisher: Huagong Shengchan Yu Jishu Bianjibu, CODEN: HSYJAC ISSN: 1006-6829.
Journal; General Review written in Chinese. CAN 143:149876 AN 2004:1026426 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
A review. The paper reviews the antioxidant effect of flavonoids. The research development of extg. methods of flavonoids is
discussed.
Answer 706:
Flavonoids from black chokeberries, Aronia melanocarpa. Slimestad, Rune; Torskangerpoll, Kjell; Nateland, Haavard S.;
Johannessen, Tina; Giske, Nils H. PlantChem, Sandnes, Norway. Journal of Food Composition and Analysis (2004), Volume
Date 2005, 18(1), 61-68. Publisher: Elsevier Ltd., CODEN: JFCAEE ISSN: 0889-1575. Journal written in English. CAN
Abstract
Black chokeberry, Aronia melanocarpa (Michx.) Elliott (Rosaceae), was investigated for its flavonoid content. The flavanone
eriodictyol 7-O-β-glucuronide, together with the quercetin derivs. 3-O-(6''-O-β-arabinosyl-β-glucoside),
3-O-(6''-α-rhamnosyl-β-galactoside), 3-O-(6''-α-rhamnosyl-β-glucoside), 3-O-β-galactoside and 3-O-β-glucoside, were detected in the
fruits and flower umbels. The rare compds. 1-3 were isolated and structurally elucidated by use of 1D- and 2D-NMR expts. together
with electrospray mass spectrometry. Compds. 4-6 were characterized by co-chromatog. and by liq. chromatog.-mass spectrometry.
The black chokeberries contained >71 mg flavonols per 100 g fresh wt.
Answer 707:
an estrone ELISA. Ohno, Ken; Araki, Naohiro; Yanase, Toshihiko; Nawata, Hajime; Iida, Mitsuru. EcoScreen R & D Section,
Endocrine Disrupting Chemical Analysis Center, Otsuka Life Science Initiative, Otsuka Pharmaceutical Co., Ltd., Kawauchi-cho,
Tokushima, Japan. Toxicological Sciences (2004), 82(2), 443-450. Publisher: Oxford University Press, CODEN: TOSCF2 ISSN:
Abstract
Aromatase is a key enzyme in steroidogenesis and plays an important role in sexual differentiation, fertility, and carcinogenesis.
flavanone
Importantly, a variety of chems. in the environment may influence its activity and thereby disrupt endocrine function. In the current
studies, we developed a novel nonradioactive method for measuring aromatase activity that uses a specific ELISA for estrone along
with KGN human ovary granulosa-like carcinoma cells. This cell line has relatively high aromatase activity, and because it lacks
17α-hydroxylase, it secretes little or no androstenedione, 17β-estradiol, or estrone. Therefore, aromatase activity can be assayed
simply by measuring the prodn. of estrone in the culture medium after addn. of the substrate, androstenedione. Furthermore, by
making a slight change in the com. ELISA kit and optimizing the exptl. conditions, we developed a sensitive aromatase assay that
could measure a wide range of estrone concns. with very low interference by androgens. We used this assay to investigate the
effects of 23 chems. that have been previously reported to affect aromatase activity in vitro. We confirmed that 17 of 23 test
chems. had inhibitory or inducible effects, although the specific effects of some were different than previously reported. In
conclusion, we have developed a simple, sensitive, and nonradioactive assay that can be used for large-scale screening of compds.
that can disrupt endocrine function by influencing aromatase activity.
Answer 708:
Enantioseparation on mono(6A-N-allylamino-6A-deoxy)permethylated β-cyclodextrin covalently bonded silica gel. Lai,

Xiang-Hua; Ng, Siu-Choon. Department of Chemistry, National University of Singapore, Singapore, Singapore. Journal of
Abstract
A chiral selector, mono(6A-N-allylamino-6A-deoxy)permethylated β-cyclodextrin, was synthesized through a facile synthetic route and
chem. immobilized onto porous silica gel via hydrosilylation to afford a cyclodextrin based chiral stationary phase MeCD-CSP. This
chiral stationary phase exhibited good enantioselectivity under std. HPLC conditions. The optimal resoln. of 1-(p-bromophenyl)ethanol
and bromopheniramine was achieved under normal-phase conditions using a mobile phase comprising n-hexane and 2-propanol (IPA).
The enantiosepn. of warfarin, suprofen and flavanones under reversed-phase conditions were optimized and efficient enantiosepns. for
these analytes were obtained.
Answer 709:
Flavonoid glycosides with enzymic modification for prevention and treatment of type-II diabetes. Tamura, Wataru;
Matsuyama, Kayo; Kagami, Yoshiaki. (Ezaki Glico Co., Japan). Jpn. Kokai Tokkyo Koho (2004), 6 pp. CODEN: JKXXAF JP

JP 2004323469 A 20041118 JP 2003-123434 20030428
JP 2003-123434 20030428
Abstract
flavanone
Flavonoid glycosides, including flavane, flavanone, flavanol, flavone, isoflavone, and chalcone, with enzymic modification on their
sugar chain are claimed as drugs and health foods for prevention and treatment of type-II diabetes.
Answer 710:
Molecular genetics of ascochyta blight resistance in chickpea (cicer arietinum l.): genomic and biochemical dissection of
quantitative resistance. Cho, Seungho. Washington State Univ., Pullman, WA, USA. Avail. UMI, Order No. DA3110850.
(2003), 103 pp. From: Diss. Abstr. Int., B 2004, 64(11), 5330. Dissertation written in English. CAN 142:352188 AN
Answer 711:
Inhibitory effects of several flavonoids on prostaglandin production and E-selectin expression in cultured animal cells.
Takano-Ishikawa, Y.; Goto, M.; Yamaki, K. National Food Research Institute, Tsukuba, Ibaraki, Japan. Editor(s): Yagasaki,
Kazumi. Animal Cell Technology: Basic & Applied Aspects, Proceedings of the Annual Meeting of the Japanese Association for
Animal Cell Technology, 15th, Fuchu, Japan, Nov. 11-15, 2002 (2003), Meeting Date 2002, 417-421. Publisher: Kluwer Academic
Publishers, Dordrecht, Neth CODEN: 69GBKC Conference written in English. CAN 142:133721 AN 2004:962523 CAPLUS
Abstract
Recent studies on food function show that foods and their components exhibit anti-inflammatory and anti-allergic activities. We have
investigated the suppressive effect of flavonoids on lipopolysaccharide (LPS)-induced prostaglandin (PG) prodn. on rat peritoneal
macrophage and tumor necrosis factor (TNF)-α-stimulated E-selectin expression on human umbilical vein endothelial cells (HUVECs)
carrying out a comparative examn. of the flavonoids. A comparison of the subclasses showed that flavone and flavanone on
prostaglandin prodn., flavone and flavonol on E-selectin expression were relatively more effective than other subclasses. From the
viewpoint of the structure, the C2-C3 double bond of C ring and the 4-oxo functional group are essential for their inhibition activities.
The glycosylated derivs. of the various flavonoids exhibit less inhibitory activities than their corresponding aglycons.
Answer 712:
In Vitro Antibacterial and Antifungal Activities of Extracts and Compounds from Uvaria scheffleri. Moshi, Mainen; Joseph,
Cosam; Innocent, Esther; Nkunya, Mayunga. Department of Pharmacology and Toxicology, Institute of Traditional Medicine, Dar
Es Salaam, Tanzania. Pharmaceutical Biology (Lisse, Netherlands) (2004), 42(4-5), 269-273. Publisher: Taylor & Francis The
Netherlands, CODEN: PHBIFC ISSN: 1388-0209. Journal written in English. CAN 143:74652 AN 2004:962011 CAPLUS
Abstract
Petroleum ether, dichloromethane, and ethanolic exts. of the stem bark and leaves of Uvaria scheffleri (Annonaceae) exhibited
antifungal activity against Aspergillus niger (wild strain), Aspergillus fumigatus (wild strain), and a Penicillium species (wild strain). The
ethanol ext. of the stem bark was also active against Candida albicans (Strain H6392). The dichloromethane ext. of the leaves showed
the highest antifungal activity and in addn. it showed antibacterial activity against Staphylococcus aureus (NCTC 6571). Fractionation
of the dichloromethane ext. of the leaves yielded nine known compds. They included a 1 : 1 mixt. of stigmasterol (1) and β-sitosterol
flavanone
(2), which showed antifungal activity against Candida albicans. Others were 3-farnesylindole (3),
2',6'-dihydroxy-3',4'-dimethoxy-chalcone (4), 2'-hydroxy-3',4',6'-trimethoxychalcone (5), 5-hydroxy-7,8-dimethoxyflavanone (6),
5,7,8-trimethoxyflavanone (7), and a 3 : 2 mixt. of 2',6'-dihydroxy-4'-methoxychalcone (8) and 5,7-dihydroxyflavone (9). Compd. 7
and the mixt. of compds. 8 and 9 showed antibacterial activity against Escherichia coli (NCTC 10418, MIC 125 μg/mL) and
Staphylococcus aureus (MIC 125 μg/mL), resp. The mixt. of compds. 8 and 9 was also active against Candida albicans (MIC 31.25
μg/mL), Aspergillus niger, Aspergillus fumigatus, and the Penicillium species (MIC 1000 μg/mL). We conclude that Uvaria scheffleri
exts. contain compds. with antifungal and antibacterial activity. The activities obsd. in this study are weak. Based on previous
studies, it is being speculated that, possibly, the most active compds. were lost during fractionation. Further work to isolate more
antifungal and antibacterial compds. is suggested.
Answer 713:
Fractionation of orange peel phenols in ultrafiltered molasses and mass balance studies of their antioxidant levels.
Manthey, John A. Citrus and Subtropical Products Laboratory, Southern Atlantic Area, Agricultural Research Service, U.S.
Department of Agriculture, Winter Haven, FL, USA. Journal of Agricultural and Food Chemistry (2004), 52(25), 7586-7592.
Abstract
Orange peel molasses, a byproduct of juice prodn., contains high concns. of phenols, including numerous flavanone and flavone
glycosides, polymethoxylated flavones, hydroxycinnamates, and other misc. phenolic glycosides and amines. Extensive
fractionation of these phenols was achieved by adsorption, ion exchange, and size exclusion chromatog. Size exclusion chromatog.
effectively sepd. the different classes of flavonoids in ultrafiltered molasses, including the polymethoxylated flavones,
flavanone-O-trisaccharides, flavanone- and flavone-O-disaccharides, and, finally, flavone-C-glycosides. Mass spectral anal. of the
early-eluting flavonoid fractions off the size exclusion column revealed a broad collection of minor-occurring flavone glycosides, which
included, in part, glycosides of limocitrin, limocitrol, and chrysoeriol. Most hydroxycinnamates in the molasses were recovered by ion
exchange chromatog., which also facilitated the recovery of fractions contg. many other misc. phenols. Total antioxidant levels and
total phenolic contents were measured for the sep. categories of phenols in the molasses. Inhibition of the superoxide anion redn. of
nitroblue tetrazolium showed that a significant amt. of the total antioxidant activity in orange peel molasses was attributable to
minor-occurring flavones. The misc. phenolic-contg. fractions, in which a large portion of the total phenolic content in molasses
occurred, also constituted a major portion of the total antioxidants in ultrafiltered molasses.
Answer 714:
Inactivation of DFR (Dihydroflavonol 4-reductase) gene transcription results in blockage of anthocyanin production in
yellow onions (Allium cepa). Kim, Sunggil; Binzel, Marla L.; Park, Sunghun; Yoo, Kil-Sun; Pike, Leonard M. Vegetable and Fruit
Improvement Center, Department of Horticultural Sciences, Texas A & M University, TX, USA. Molecular Breeding (2004), 14(3),
253-263. Publisher: Kluwer Academic Publishers, CODEN: MOBRFL ISSN: 1380-3743. Journal written in English. CAN
Abstract
Anthocyanin, one of the flavonoids, is a primary determinant of red color in onions. Inheritance studies indicate that a single gene
dets. the color difference between yellow and red onions. In order to establish which gene might be responsible for this color
difference, full-length cDNAs of five structural genes: chalcone synthase (CHS), flavanone 3-hydroxylase (F3H), dihydroflavonol
4-reductase (DFR), anthocyanidin synthase (ANS), and flavonol synthase (FLS) were cloned using degenerate PCR and RACE (Rapid
flavanone
Amplification of cDNA Ends). RT-PCR was carried out for these five genes to examine differential expression between yellow and red
colored bulbs. Accumulation of the DFR gene transcript only occurred in red onions. In F3 populations which originated from the cross
between yellow and red parents, DFR transcript was detected only in red F3 lines. To design mol. markers for selection of yellow and
red DFR alleles, the DFR gene was sequenced from genomic DNA isolated from both types of onions. The genomic DNA sequence
revealed the DFR gene consists of six exons and five introns. A PCR-RFLP marker was designed based on 2% polymorphic
nucleotide sequence of the DFR gene between yellow and red onions. The co-segregation of markers and red color were obsd. in F2
segregating populations, supporting the conclusion that color difference in red and yellow onions is likely to be due to the lack of an
active DFR gene.
Answer 715:
Regulation of gene expression involved in flavonol and anthocyanin biosynthesis during petal development in lisianthus
(Eustoma grandiflorum). Noda, Naonobu; Kanno, Yoshiaki; Kato, Naoki; Kazuma, Kohei; Suzuki, Masahiko. Aomori Green
BioCenter, Aomori, Japan. Physiologia Plantarum (2004), 122(3), 305-313. Publisher: Blackwell Publishing Ltd., CODEN: PHPLAI
SciFinder (R))
Abstract
To elucidate gene regulation of flower color formation, the gene expressions of the enzymes involved in flavonoid biosynthesis were
investigated in correlation with their product during floral development in lisianthus. Full-length cDNA clones of major responsible
genes in the central flavonoid biosynthetic pathway, including chalcone synthase (CHS), chalcone isomerase (CHI), flavanone
3-hydroxylase (F3H), flavonoid 3',5'-hydroxylase (F3'5'H), dihydroflavonol 4-reductase (DFR), anthocyanidin synthase (ANS), and
flavonol synthase (FLS), were isolated and characterized. In lisianthus, the stage of the accumulation of flavonols and anthocyanins
was shown to be divided clearly. The flavonol content increased prior to anthocyanin accumulation during floral development and
declined when anthocyanin began to accumulate. CHS, CHI, and F3H were necessary for both flavonol and anthocyanin biosynthesis
and were coordinately expressed throughout all stages of floral development; their expressions were activated independently at the
stages corresponding to flavonol accumulation and anthocyanin accumulation, resp. Consistent with flavonol and anthocyanin
accumulation patterns, FLS, a key enzyme in flavonol biosynthesis, was expressed prior to the expression of the genes involved in
anthocyanin biosynthesis. The genes encoding F3'5'H, DFR, and ANS were expressed at later stages, just before pigmentation. The
genes responsible for the flavonoid pathways branching to anthocyanins and flavonols were strictly regulated and were coordinated
temporally to correspond to the biosynthetic order of their resp. enzymes in the pathways, as well as in specific organs. In lisianthus,
FLS and DFR, at the position of branching to flavonols and anthocyanins, were supposed to play a crit. role in regulation of each
biosynthesis.
Answer 716:
Temporal and spatial expression of flavonoid biosynthetic genes in flowers of Anthurium andraeanum. Collette, Vern E.;
Jameson, Paula E.; Schwinn, Kathy E.; Umaharan, Pathmanathan; Davies, Kevin M. New Zealand Institute for Crop and Food
Research Limited, Palmerston North, N. Z. Physiologia Plantarum (2004), 122(3), 297-304. Publisher: Blackwell Publishing Ltd.,
CODEN: PHPLAI ISSN: 0031-9317. Journal written in English. CAN 142:257822 AN 2004:954432 CAPLUS (Copyright (C)
Abstract
The expression of anthocyanin biosynthesis genes during flower color development in Anthurium andraeanum (anthurium) was studied.
A cDNA library was constructed from mRNA from the anthurium spathe, and full-length cDNA clones were identified for the flavonoid
flavanone
biosynthetic enzymes chalcone synthase (CHS), flavanone 3-hydroxylase (F3H), dihydroflavonol 4-reductase (DFR) and
anthocyanidin synthase (ANS). These were used to measure transcript levels in the spathe during flower development, in cultivars
with different flower colors, over the diurnal cycle, and in the spadix. CHS, F3H and ANS were expressed at all stages of spathe and
spadix development. However, DFR transcript levels varied significantly between stages, and DFR may represent a key point of
regulation. A diurnal rhythm of DFR transcript abundance in the spathe was also obsd., with transcript levels high at dawn and dusk
and low at noon. Control of anthocyanin biosynthesis in anthurium spathe differs from that described for flowers of other species,
with DFR a key regulatory point and a complex mix of developmental and environmental control signals.
Answer 717:
Mechanisms of Naringenin-induced Apoptotic Cascade in Cancer Cells: Involvement of Estrogen Receptor α and β
Signalling. Totta, Pierangela; Acconcia, Filippo; Leone, Stefano; Cardillo, Irene; Marino, Maria. Dept. Biol., University Roma Tre,
Rome, Italy. IUBMB Life (2004), 56(8), 491-499. Publisher: Taylor & Francis Ltd., CODEN: IULIF8 ISSN: 1521-6543. Journal
Abstract
The flavanone naringenin (Nar), esp. abundant in the Mediterranean diet, is reported to have antiproliferative effects in many cancer
cell lines. Antioxidant activities, kinase and glucose uptake inhibition have been proposed as mol. mechanisms for these effects. In
addn., an antiestrogenic activity has been obsd. but, at the present, it is poorly understood whether this latter activity could play a role
in the Nar antitumoral effects. Here, the authors tested the ability of Nar to activate a specific, rapid signal transduction pathway
committed to the generation of an apoptotic cascade in the presence of one of the two estrogen receptor (ER) isoforms (i.e., ERα or
ERβ). Cancer cells contg. transfected (human cervix epitheloid carcinoma HeLa cells) or endogenous ERα (human hepatoma HepG2
cells) or ERβ (human colon adenocarcinoma DLD-1 cells) were used. Our results show that Nar exerts an antiproliferative effect only
in the presence of ERα or ERβ. Moreover, Nar stimulation induces the activation of p38/MAPK leading to the pro-apoptotic caspase-3
activation and to the poly(ADP-ribose) polymerase cleavage in all cancer cell lines considered. Notably, Nar shows an antiestrogenic
effect only in ERα contg. cells; whereas in ERβ contg. cells, Nar mimics the 17β-estradiol effects. These findings indicate new steps
in the mechanism underlying ER-dependent antiproliferative effects of Nar suggesting new potential chemopreventive actions of
flavonoids on cancer growth.
Answer 718:
Effects of several agents on mucin release from cultured airway epithelial cells of rodents. Lee, Choong-Jae; Seok,
Jeong-Ho; Lee, Jae-Heun; Hur, Gang-Min; Park, Ji-Sun; Bae, So-Hyun; Row, Sam-Gil; Park, Sang-Cheol. Department of
Pharmacology, College of Medicine, Chungnam National University, S. Korea. Chungnam Uidae Chapchi (2003), 30(2), 45-53.
Publisher: Chungnam National University, College of Medicine, CODEN: CUCHDS ISSN: 0253-6307. Journal written in Korean.
Abstract
In the present study, we tried to investigate whether phorbol myristate acetate (PMA), trihydroxymethoxyflavanone rutinoside (TFR)
and cationic polypeptides significantly affect mucin release (secretion) from cultured hamster tracheal surface epithelial cells.
Confluent primary hamster tracheal surface epithelial (HTSE) cells were metabolically radiolabeled with 3H-glucosamine for 24 h and
chased for 30 min in the presence of each agent to assess the effect on 3H-mucin release. The results were as follows: (1) Both PMA
and TFR significantly increased mucin release from cultured HTSE cells: (2) Cationic polypeptides including poly-L-lysine (PLL, mw
7,500) and poly-L-arginine (PLA, mw 10,800) significantly inhibited mucin release from cultured HTSE cells, in a dose-dependent
manner. This finding suggests us that PMA and TFR be further studied for the possible use as mild expectorants and cationic
flavanone
polypeptides, might function as a regulator for hypersecretion of mucus, both by direct acting on airway mucin-secreting cells, during
the treatment of chronic airway diseases.
Answer 719:
Citrus fruit bitter flavors: isolation and functional characterization of the gene Cm1,2RhaT encoding a 1,2
rhamnosyltransferase, a key enzyme in the biosynthesis of the bitter flavonoids of citrus. Frydman, Ahuva; Weisshaus,
Oori; Bar-Peled, Maor; Huhman, David V.; Sumner, Lloyd W.; Marin, Francisco R.; Lewinsohn, Efraim; Fluhr, Robert; Gressel,
Jonathan; Eyal, Yoram. Institute of Horticulture, The Volcani Center, ARO, Bet-Dagan, Israel. Plant Journal (2004), 40(1),
88-100. Publisher: Blackwell Publishing Ltd., CODEN: PLJUED ISSN: 0960-7412. Journal written in English. CAN 143:91696 AN
Abstract
Species of the genus Citrus accumulate large quantities of flavanones that affect fruit flavor and have been documented to benefit
human health. Bitter species, such as grapefruit and pummelo, accumulate bitter flavanone-7-O-neohesperidosides responsible, in
part, for their characteristic taste. Non-bitter species, such as mandarin and orange, accumulate only tasteless
flavanone-7-O-rutinosides. The key flavor-detg. step of citrus flavanone-glycoside biosynthesis is catalyzed by
rhamnosyltransferases; 1,2 rhamnosyltransferases (1,2RhaT) catalyze biosynthesis of the bitter neohesperidosides, while 1,6
rhamnosyltransferases (1,6RhaT) catalyze biosynthesis of the tasteless rutinosides. The authors report on the isolation and functional
characterization of the gene Cm1,2RhaT from pummelo which encodes a citrus 1,2RhaT. Functional anal. of Cm1,2RhaT recombinant
enzyme was conducted by biotransformation of the substrates using transgenic plant cell culture. Flavanones and flavones, but not
flavonols, were biotransformed into 7-O-neohesperidosides by the transgenic BY2 tobacco cells expressing recombinant Cm1,2RhaT.
Immunoblot anal. established that 1,2RhaT protein was expressed only in the bitter citrus species and that 1,6RhaT enzyme, whose
activity was previously documented in non-bitter species, was not cross-reactive. Expression of Cm1,2RhaT at the RNA level was
prominent in young fruit and leaves, but low in the corresponding mature tissue, thus correlating well with the developmental pattern of
accumulation of flavanone-neohesperidosides previously established. Phylogenetic anal. of the flavonoid glycosyltransferase gene
family places Cm1,2RhaT on a sep. gene cluster together with the only other functionally characterized flavonoid-glucoside
rhamnosyltransferase gene, suggesting a common evolutionary origin for rhamnosyltransferases specializing in glycosylation of the
sugar moieties of flavonoid glucosides.
Answer 720:
Novel flavanone glucoside with free radical scavenging properties from Galium fissurense. Orhan, D. Deliorman.
Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, Ankara, Turk. Pharmaceutical Biology (Lisse, Netherlands)
(2003), 41(7), 475-478. Publisher: Swets & Zeitlinger B.V., CODEN: PHBIFC ISSN: 1388-0209. Journal written in English. CAN
Abstract
From the herb of Galium fissurense, a new flavanone glucoside was isolated and characterized as
5,7,3'-trihydroxyflavanone-4'-O-β-D-glucopyranoside (1) from spectroscopic evidence. In addn., three known compds. (luteolin,
apigenin-7-O-β-D-glucopyranoside, naringenin-7-O-β-D-glucopyranoside) were isolated for the first time from this plant. The free radical
scavenging properties of the four compds. were studied by use of in vitro ESR spectrometry. The new compd. showed potent
antioxidant activity.
Answer 721:
flavanone
Preparation of flavanone derivatives and composition for preventing or treating blood lipid level-related diseases. Bok,
Seong Hae; Choi, Myeong Suk; Choi, Yang Gyu; Hyun, Byeong Hwa; Jung, Tae Suk; Kim, Ju Ryeong; Lee, Cheol Ho; Lee, Sang Gu;
Mun, Seok Sik. (Korea Research Institute of Bioscience and Biotechnology, S. Korea). Repub. Korean Kongkae Taeho Kongbo
(2002), No pp. given. CODEN: KRXXA7 KR 2002059027 A 20020712 Patent written in Korean. Application: KR 2000-87185

KR 2002059027 A 20020712 KR 2000-87185 20001230
KR 2000-87185 20001230
Abstract
Provided are flavanone derivs. which decrease blood lipid level, inhibits cholesterol metab. related enzyme, treat and prevent
arteriosclerosis, and protect liver function. Also, provided are a compn. for preventing or treating blood lipid level-related diseases
comprising same. The flavanone deriv. having excellent improving effects on lipid metab. is represented by the formula(1), wherein
R1 is R5 or R6CO-; R2 is H or R6CO-; R3 is H, CH3, R5 or R6CO-; R4 is H, OH, OR5 or R6COO-; R5 is unsubstituted or substituted
C2-C5 alkyl with Ph which is substituted with at least one of C1-C3 alkyl, OH, Cl or NO2, unsubstituted or substituted C1-C5 alkyl with
substituted naphthyl which is substituted with at least one of C1-C3 alkyl, OH, Cl or NO2, or C10-18 alkyl or alkenyl; and R6 is C10-18
alkenyl or unsubstituted or substituted aryl with at least one of C1-3 alkyl, OH or NO2.
Answer 722:
Enantioselective acylation of (±)-cis-flavan-4-ols catalyzed by lipase from Candida cylindracea (CCL) and the synthesis of
enantiopure flavan-4-ones. Ramadas, Sathunuru; Krupadanam, G. L. David. Department of Chemistry, Osmania University,
Hyderabad, India. Tetrahedron: Asymmetry (2004), 15(21), 3381-3391. Publisher: Elsevier B.V., CODEN: TASYE3 ISSN:
Abstract
Lipase Candida cylindracea (CCL) catalyzed acylation of (±)-cis-flavan-4-ols using vinyl acetate as the acyldonor in DME-toluene (1:2)
gave (-)-(2R,4R)-4-acetoxyflavans and (+)-(2S,4S)-flavan-4-ols in high enantiomeric excess. (+)-(2S,4S)-Flavan-4-ols were converted
to (-)-(2S)-flavan-4-ones.
Answer 723:
Conversion from Arenes Having a Benzene Ring to Those Having a Picolinic Acid by Simple Growing Cell Reactions Using
flavanone
Escherichia coli that Expressed the Six Bacterial Genes Involved in Biphenyl Catabolism. Shindo, Kazutoshi; Osawa, Ayako;
Nakamura, Ryoko; Kagiyama, Yukiko; Sakuda, Shohei; Shizuri, Yoshikazu; Furukawa, Kensuke; Misawa, Norihiko. Department of
Food and Nutrition, Japan Women's University, Tokyo, Japan. Journal of the American Chemical Society (2004), 126(46),
15042-15043. Publisher: American Chemical Society, CODEN: JACSAT ISSN: 0002-7863. Journal written in English. CAN
Abstract
The comprehensive bioconversion of arom. compds. with a benzene ring to a picolinic acid was achieved with a recombinant
Escherichia coli strain that expressed the six genes involved in biphenyl catabolism, these being the bphA1(2072)A2A3A4 genes
encoding the evolved biphenyl dioxygenase, the bphB gene encoding dihydrodiol dehydrogenase, and the bphC gene encoding
catechol 2,3-dioxygenase.
Answer 724:
Anti-plasmodial flavonoids from the stem bark of Erythrina abyssinica. Yenesew, Abiy; Induli, Martha; Derese, Solomon;
Midiwo, Jacob O.; Heydenreich, Matthias; Peter, Martin G.; Akala, Hoseah; Wangui, Julia; Liyala, Pamela; Waters, Norman C.
Department of Chemistry, University of Nairobi, Nairobi, Kenya. Phytochemistry (Elsevier) (2004), 65(22), 3029-3032.
Publisher: Elsevier B.V., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 142:71494 AN 2004:886419
Abstract
The Et acetate ext. of the stem bark of Erythrina abyssinica showed anti-plasmodial activity against the chloroquine-sensitive (D6) and
chloroquine-resistant (W2) strains of Plasmodium falciparum with IC50 values of 7.9±1.1 and 5.3±0.7 μg/mL, resp. From this ext., a
new chalcone, 2',3,4,4'-tetrahydroxy-5-prenylchalcone (trivial name 5-prenylbutein) and a new flavanone,
4',7-dihydroxy-3'-methoxy-5'-prenylflavanone (trivial name, 5-deoxyabyssinin II) along with known flavonoids have been isolated as
the anti-plasmodial principles. The structures were detd. on the basis of spectroscopic evidence.
Answer 725:
Protein and cDNA sequences of novel chalcone synthase (CHS), dihydroflavonol 4-reductase (BAN) and leucoanthocyanidin
reductase (LAR) from Trifolium repens flavanone and use for stress-resistance plant. Spangenberg, German; Emmerling,
Michael; Simmonds, Jason; Winkworth, Amanda; Panter, Stephen. (Agriculture Victoria Services Pty Ltd, Australia; Agresearch
Limited). PCT Int. Appl. (2004), 117 pp. CODEN: PIXXD2 WO 2004090136 A1 20041021 Designated States W: AE, AG, AL,
AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE,
GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI,
NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA,
ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG,
CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2004-AU494 20040414. Priority: AU
2003-901797 20030414; AU 2003-904369 20030814. CAN 141:344617 AN 2004:872846 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))

flavanone
WO 2004090136 A1 20041021 WO 2004-AU494 20040414

ZW
RW: BW, GH, GM, KE, LS, MW, MZ, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM,
AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IT, LU, MC, NL, PL, PT, RO, SE,
SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG
AU 2004228984 A1 20041021 AU 2004-228984 20040414
CA 2522056 A1 20041021 CA 2004-2522056 20040414
EP 1618198 A1 20060125 EP 2004-727184 20040414
NZ 542732 A 20080131 NZ 2004-542732 20040414
US 20060195920 A1 20060831 US 2005-552857 20051014
AU 2003-901797 A 20030414
AU 2003-904369 A 20030814
WO 2004-AU494 W 20040414
Abstract
The present invention relates to nucleic acid fragments encoding amino acid sequences for flavonoid biosynthetic enzymes in plants,
and the use thereof for the modification of, for example, flavonoid biosynthesis in plants, and more specifically the modification of
the content of condensed tannins. In particularly preferred embodiments, the invention relates to the combinatorial expression of
chalcone synthase (CHS) and/or dihydroflavonol 4-reductase (BAN) and/or leucoanthocyanidin reductase (LAR) in plants to modify,
for example, flavonoid biosynthesis or more specifically the content of condensed tannins.
Answer 726:
Estrogenic and Anticarcinogenic Properties of Kurarinone, a Lavandulyl Flavanone from the Roots of Sophora flavescens.
De Naeyer, An; Vanden Berghe, Wim; Pocock, Victoria; Milligan, Stuart; Haegeman, Guy; De Keukeleire, Denis. Laboratory of
Pharmacognosy and Phytochemistry, Faculty of Pharmaceutical Sciences, Ghent University, Ghent, Belg. Journal of Natural
Products (2004), 67(11), 1829-1832. Publisher: American Chemical Society, CODEN: JNPRDF ISSN: 0163-3864. Journal written
Abstract
Kurarinone, a lavandulyl flavanone, was isolated from a polyphenolic ext. of the roots of Sophora flavescens using fractionation
guided by estrogenic activity, which was detd. by recombinant yeast and Ishikawa Var-I bioassays. Kurarinone showed weak
estrogenic activity both in the yeast screen and in the Ishikawa Var-I assay with EC50 values of 4.6 and 1.66 μM, resp. Furthermore,
kurarinone was found to have potent cytotoxic activity (IC50 value = 22.2 μM) against human MCF-7/6 breast cancer cells in the
sulforhodamine-B assay.
flavanone
Answer 727:
Hesperidin, a citrus flavanone, improves bone acquisition and prevents skeletal impairment in rats. Horcajada,
Marie-Noelle; Coxam, Veronique. Unite des Maladies Metaboliques et Micronutriments, Groupe Osteoporose, INRA de Theix, Fr.
Editor(s): Burckhardt, Peter; Dawson-Hughes, Bess; Heaney Robert P. Nutritional Aspects of Osteoporosis, [International Symposia
on Nutritional Aspects of Osteoporosis], 5th, Lausanne, Switzerland, May 14-17, 2003 (2004), Meeting Date 2003, 109-126.
Publisher: Elsevier, San Diego, Calif CODEN: 69FZF6 Conference written in English. CAN 142:92943 AN 2004:860105
Abstract
Flavonoids are a large family of compds. assocd. with many biol. activities (e.g., antioxidant, estrogenic, antiinflammatory properties).
Until now, the most examd. (iso)flavonoids with respect to bone health are the soy isoflavones, which have been shown to prevent
bone loss in the ovariectomized rat and attenuate spinal bone loss in postmenopausal women. Citrus fruits are rich in flavanones.
Hesperidin (Hp), is one of the main flavanones in oranges. The authors investigated its effect on bone metab. in intact and
ovariectomized rats. The study was carried out on 40 3-mo-old Wistar female rats; 20 were sham operated (SH), while the others were
ovariectomized (OVX). Among each group, 10 sham-operated (TSH) and 10 ovariectomized (TOVX) rats were fed a std. diet for 90
days following surgery, and the 20 remaining animals received the same regimen but with 0.5% hesperidin added (10 HpSH, 10
HpOVX). At necropsy, the ovariectomy-induced uterine wt. decrease did not differ between TOVX and HpOVX rats. Hesperidin
consumption totally prevented the ovariectomy-induced demineralization (bone mineral d. TOVX: -6.2% vs. TSH; HpOVX vs. TSH: NS;
HpOVX: +10.7% vs. TOVX), and significantly improved femoral metaphyseal d. (HpSH: +11.5% vs. TSH) in intact rats as well. The
femoral diaphyseal d. was also significantly enhanced by hesperidin in both SH and OVX rats, while an improvement of bone strength
was only obsd. in ovariectomized animals. Plasma osteocalcin concns. were higher in HpOVX (P < 0.05 vs. HpSH). Urinary
deoxypyridinolin excretion was reduced (P < 0.01) in both HpSH and HpOVX rats compared to their controls. Finally, the plasma
concn. of hesperetin (the aglycon form) was 12.53 ± 2.48 μM in hesperidin fed rats, bile the mol. stayed undetectable in control rats.
These results indicate that, under our exptl. conditions, hesperidin consumption was able to improve bone mass acquisition in intact
rats and exhibited a significant protection against ovariectomy-induced bone impairment.
Answer 728:
Synthesis of new 2,3-dihydro-2-phenyl-4-quinolone derivatives; Aza analogs of flavanone. Park, Myung-Sook; Lee, Jae-In.
College of Pharmacy, Duksung Women's University, Seoul, S. Korea. Bulletin of the Korean Chemical Society (2004), 25(8),
1269-1272. Publisher: Korean Chemical Society, CODEN: BKCSDE ISSN: 0253-2964. Journal written in English. CAN 142:261383
Abstract
A procedure for the synthesis of 2,3-dihydro-2-phenyl-4-quinolinones, e.g., I, is reported. Anilines underwent condensation with Et
benzoylacetate followed by heterocyclization to give the corresponding 2,3-dihydro-2-phenyl-4-quinolinones in good yields.
flavanone
MeO
H
I
Answer 729:
Study of the molluscicidal activity of some phenolic compounds: structure-activity relationship. Lahlou, Mouhssen.
Laboratoire de Biochimie, Biologie Cellulaire et Moleculaire, Departement de Biologie, Unite de Formation et de Recherche: Biologie et
Sante, Faculte des Sciences Ain Chock, Casablanca, Morocco. Pharmaceutical Biology (Lisse, Netherlands) (2004), 42(3),
258-261. Publisher: Taylor & Francis The Netherlands, CODEN: PHBIFC ISSN: 1388-0209. Journal written in English. CAN
Abstract
The relationship between the structure of 14 phenolic compds. and their molluscicidal activity against the molluscan intermediate host
of urinary schistosomiasis, Bulinus truncatus, is discussed. It was found that among flavonoids tested, unhydroxylated flavone
compd. and flavanone hesperidin were the most active (LC50 = 5.47 and 8.91 ppm, resp.), whereas gallic acid compd. with
para-methoxy group was the most effective among phenolic acids tested (LC50 = 3.60 ppm). These results are encouraging and prove
other biol. application of these compds.
Answer 730:
A cancer chemopreventive agent silibinin, targets mitogenic and survival signaling in prostate cancer. Singh, Rana P.;
Agarwal, Rajesh. Department of Pharmaceutical Sciences, School of Pharmacy, University of Colorado Health Sciences Center,
Denver, CO, USA. Mutat. Res. (2004), 555(1-2), 21-32. Publisher: Elsevier B.V., CODEN: MUREAV ISSN: 0027-5107.
(R))
Abstract
A review. There are many epigenetic variables that affect the biol. responses of autocrine, paracrine and endocrine regulatory mols.,
which det. the growth and development of different cancers including prostate cancer (PCA). One of the focuses of the current cancer
chemoprevention studies is the search for non-toxic chemopreventive agents that inhibit mitogenic and cell survival signaling in cancer
cells. In general, advanced stage cancer cells harbor many constitutively active mitogenic signaling and anti-apoptotic mechanisms,
which make them less dependent on external growth factors as well as resistant to chemotherapeutic agents. In this regard, silibinin (a
naturally occurring flavanone) has shown the pleiotropic anticancer effects in different cancer cells. Our extensive studies with PCA
have shown that inhibition of mitogenic and cell survival signaling, such as epidermal growth factor receptor, insulin-like growth factor
receptor type I and nuclear factor kappa B signaling are the most likely mol. targets of silibinin's efficacy in PCA. We have obsd. that
silibinin inhibits prostate tumor growth in animal models without any apparent signs of toxicity. At the same time, silibinin is also
flavanone
physiol. available in different organs of the body including plasma and prostate, which is generally required for the pharmacol. dosing
and translational mechanistic studies of the compd. There are substantial amt. of data to support the inhibitory effect of silibinin on
mitogenic and cell survival signaling in PCA, which are reviewed in the present communication.
Answer 731:
Compositions and methods for therapy for diseases characterized by defective chloride transport. Fischer, Horst; Illek,
Beate. (Children's Hospital Oakland, USA). U.S. Pat. Appl. Publ. (2004), 69 pp., Cont.-in-part of U.S. Ser. No. 982,315.
CODEN: USXXCO US 2004197272 A1 20041007 Patent written in English. Application: US 2004-769619 20040130. Priority: US
97-951912 19971016; US 98-174077 19981016; US 2001-982315 20011017. CAN 141:320085 AN 2004:824855 CAPLUS

US 20040197272 A1 20041007 US 2004-769619 20040130
US 5972995 A 19991026 US 1997-951912 19971016
US 6329422 B1 20011211 US 1998-174077 19981016
EP 1669067 A2 20060614 EP 2005-17863 19981016
EP 1669067 A3 20061122
R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT, IE, FI, CY
US 20030096762 A1 20030522 US 2001-982315 20011017
US 7335683 B2 20080226
US 1997-951912 A2 19971016
US 1998-174077 A3 19981016
US 2001-982315 A2 20011017
EP 1998-953609 A3 19981016
Abstract
Compns. and methods for therapy of cystic fibrosis, asthma, and other conditions characterized by defective chloride transport a re
provided. The compns. comprise one or more compds. such as flavones and/or isoflavones, ascorbate and/or derivs. thereof capable
of stimulating chloride transport in epithelial tissues. Therapeutic methods involve the administration (e.g., orally or via inhalation) of
such compns. to a patient afflicted with cystic fibrosis, asthma, and/or another condition responsive to stimulation of chloride
transport. For example, L-ascorbic acid was found to be able to stimulate the CFTR activity through a cAMP mediated pathway.
Answer 732:
Flavonoid biosynthesis in the tea plant Camellia sinensis: properties of enzymes of the prominent epicatechin and catechin
pathways. Punyasiri, P. A. N.; Abeysinghe, I. S. B.; Kumar, V.; Treutter, D.; Duy, D.; Gosch, C.; Martens, S.; Forkmann, G.;
flavanone
Fischer, T. C. Biochemistry Division, Tea Research Institute of Sri Lanka, Talawakelle, Sri Lanka. Archives of Biochemistry and
Biophysics (2004), 431(1), 22-30. Publisher: Elsevier, CODEN: ABBIA4 ISSN: 0003-9861. Journal written in English. CAN
Abstract
Leaves of tea (Camellia sinensis L.) contain extraordinary large amts. of (-)-epigallocatechin, (-)-epicatechin, (+)-gallocatechin, and
(+)-catechin and derivs. of these compds. that show pos. effects on human health. The health-promoting effects of flavan-3-ols, esp.
those of green tea, are of scientific and public interest. Furthermore, they play a crucial role in defense against pathogens of tea.
Therefore, biosynthesis of these flavonoid compds. was investigated. The anthocyanidin reductase (ANR) enzyme recently described
from Arabidopsis and Medicago was shown to be present in tea with very high activity. The nonradioactive ANR assay developed
included HPLC anal. of reaction products; the enzyme produced epicatechin as well as epigallocatechin from the resp. anthocyanidins,
thus explaining the very high contents of these compds. A strong combined dihydroflavonol 4-reductase/leucoanthocyanidin
4-reductase activity was demonstrated and catalyzed the key steps in catechin and gallocatechin formation. Together with the enzyme
activities and substrate specificities of the preceding enzymic reactions, the biosynthesis of the most prominent flavonoids of tea is
elucidated.
Answer 733:
Cloning and heterologous expression of flavonoid genes of Osteosopermum hybrids. Seitz, C.; Hauser, A.; Forkmann, G.;
Martens, S. Department for Plant Sciences, Chair for Floriculture Crops and Horticultural Plant Breeding, Tu Muenchen, Freising,
Germany. Acta Horticulturae (2004), 651(Proceedings of the 21st International Symposium on Classical Versus Molecular Breeding
of Ornamentals, Part II, 2003), 107-114. Publisher: International Society for Horticultural Science, CODEN: AHORA2 ISSN:
Abstract
Petals of Osteospermum exhibit white, yellow and rose to lilac colors. Chem. and biochem. investigations elucidated the basis of
flower color in Osteospermum. Besides carotenoids, which were shown to be responsible for the yellow color, flavonoids were
identified to be the main color-giving compds. Different amts. of derivs. of the anthocyanidin delphinidin cause the rose to lilac color
range. In addn. to delphinidin, derivs. of flavonols were found to be present in the petals. Enzyme assays elucidated the biosynthetic
path leading to the formation of the 3'-, 4'-, and 5'-hydroxylated delphinidin. Because of distinct substrate specifities of the early
enzymes of the flavonoid pathway, chalcone synthase, chalcone isomerase, and flavanone 3-hydroxylase, dihydrokaempferol is
supposed to be the main branch point. This compd. was shown to be hydroxylated in 3'- and 5'- position by flavonoid 3',
5'-hydroxylase to dihydromyricetin which is subsequently reduced by dihydroflavonol 4-reductase to leucodelphinidin, the precursor of
delphinidin. Mol. biol. investigations of two key steps allowed a confirmation of the enzymol. findings. The protein of a heterologously
expressed full length chalcone synthase cDNA-clone was shown to preferentially use 4-coumaroyl-CoA as a substrate leading to the
formation of naringenin after isomerisation by chalcone isomerase. In contrast to this, caffeoyl-CoA as a substrate resulted in the
formation of only low amts. of eriodictyol. 3', 5'-Hydroxylation, which is indispensable for the formation of delphinidin, was
demonstrated with the protein of a heterologously expressed F3'5'H full-length cDNA-clone. Fragments of the other main structural
flavonoid genes of Osteospermum are now available and further mol. biol. investigation will be performed.
Answer 734:
Enzymic manufacture of aromatic diols from phenyl-containing aromatic compounds. Misawa, Norihiko; Shindo, Kazutoshi.
(Marine Biotechnology Institute Co. Ltd., Japan). PCT Int. Appl. (2004), 90 pp. CODEN: PIXXD2 WO 2004078988 A1
20040916 Designated States W: AE. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT,
flavanone
SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent
written in Japanese. Application: WO 2004-JP2654 20040303. Priority: JP 2003-57867 20030304. CAN 141:259473 AN

WO 2004078988 A1 20040916 WO 2004-JP2654 20040303
LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI
RW: BW, GH, GM, KE, LS, MW, MZ, SD, SL, SZ, TZ, UG, ZM, ZW, AT, BE, BG, CH, CY, CZ, DE, DK, EE,
ES, FI, FR, GB, GR, HU, IE, IT, LU, MC, NL, PL, PT, RO, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA,
GN, GQ, GW, ML, MR, NE, SN, TD, TG
JP 2003-57867 A 20030304
Abstract
The arom. diols which are useful antioxidants are manufd. from Ph group-contg. arom. compds. with arom. ring dioxygenase and arom.
ring dihydrodiol desaturase, or (recombinant) microorganism producing the enzymes. Manuf. of arom. diol.
2-(2,3-dihydroxyphenyl)chromen-4-one from flavone with recombinant Escherichia coli harboring plasmid pBS2072B was shown.
Answer 735:
Anthocyanins and other flavonoids. Williams, Christine A.; Grayer, Renee J. Plant Science Laboratories, The University of
Reading, Reading, UK. Natural Product Reports (2004), 21(4), 539-573. Publisher: Royal Society of Chemistry, CODEN:
NPRRDF ISSN: 0265-0568. Journal; General Review written in English. CAN 142:332850 AN 2004:746645 CAPLUS
Abstract
A review on more than 450 newly reported compds. belonging to eight different classes of flavonoids recorded in the literature from
Jan. 2001 to Dec. 2003. Brief mention is made of relevant data on the biol. activity of these flavonoids as cited in the original papers.
Answer 736:
Phenolic profile and antioxidant activity of the Algerian ripe date palm fruit (Phoenix dactylifera). Mansouri, Abdelhak;
Embarek, Guendez; Kokkalou, Eugene; Kefalas, Panagiotis. Laboratory of Chemistry of Natural Products, Department of Food
Quality Management, Mediterranean Agronomic Institute of Chania (MAICh), Crete, Chania, Greece. Food Chemistry (2004),
Volume Date 2005, 89(3), 411-420. Publisher: Elsevier B.V., CODEN: FOCHDJ ISSN: 0308-8146. Journal written in English.
flavanone
Abstract
The aim of this study was to det. the phenolic profile of seven different varieties of ripe date palm fruit (Phoenix dactylifera) from
Algeria by LC-DAD-MS (ESI+), to investigate their resp. antioxidant activities by the DPPH⋅ method and to est. their phenolic content
using the Folin-Ciocalteu method. The total phenolic content was in the range of 2.49±0.01 to 8.36±0.60 mg gallic acid equiv. (GAE)
per 100 g fresh fruit. This fruit was shown to possess an antioxidant activity, giving values of antiradical efficient (AE) from
0.08±0.00 to 0.22±0.00. The phenolic contents and the antiradical efficiencies of the different varieties were highly correlated (R2 =
0.975). All the varieties were found to contain mainly p-coumaric, ferulic and sinapic acids and some cinnamic acid derivs. Three
different isomers of 5-o-caffeoylshikimic acid were detected. Different types of flavonoids were identified, mainly flavones,
flavanones and flavonol glycosides.
Answer 737:
Natural inhibitors of carcinogenesis. Kinghorn, A. Douglas; Su, Bao-Ning; Jang, Dae Sik; Chang, Leng Chee; Lee, Dongho; Gu,
Jian-Qiao; Carcache-Blanco, Esperanza J.; Pawlus, Alison D.; Lee, Sang Kook; Park, Eun Jung; Cuendet, Muriel; Gills, Joell J.; Bhat,
Krishna; Park, Hye-Sung; Mata-Greenwood, Eugenia; Song, Lynda L.; Jang, Meishiang; Pezzuto, John M. Program for Collaborative
Research in the Pharmaceutical Sciences, Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University
of Illinois at Chicago, Chicago, IL, USA. Planta Medica (2004), 70(8), 691-705. Publisher: Georg Thieme Verlag, CODEN:
PLMEAA ISSN: 0032-0943. Journal; General Review written in English. CAN 141:235488 AN 2004:742602 CAPLUS
Abstract
A review. Previous collaborative work by our group has led to the discovery of several plant isolates and derivs. with activities in in
vivo models of cancer chemoprevention, including deguelin, resveratrol, bruceantin, brassinin, 4'-bromoflavone, and oxomate. Using a
panel of in vitro bioassays to monitor chromatog. fractionation, a diverse group of plant secondary metabolites has been identified as
potential cancer chemopreventive agents from mainly edible plants. Nearly 50 new compds. have been isolated as bioactive
principles in one or more in vitro bioassays in work performed over the last five years. Included among these new active compds. are
alkaloids, flavonoids, stilbenoids, and withanolides, as well as a novel stilbenolignan and the first representatives of the
norwithanolides, which have a 27-carbon atom skeleton. In addn., over 100 active compds. of previously known structure have been
obtained. Based on this large pool of potential cancer chemopreventive compds., structure-activity relationships are discussed in
terms of the quinone reductase induction ability of flavonoids and withanolides and the cyclooxygenase-1 and -2 inhibitory activities of
flavanones, flavones and stilbenoids. Several of the bioactive compds. were active when evaluated in a mouse mammary organ
culture assay, when used as a secondary discriminator in our work. The compds. (2S)-abyssinone II,
(2S)-2',4'-dihydroxy-2''-(1-hydroxy-1-methylethyl)dihydrofuro[2,3-h]-flavanone,
3'-[γ-hydroxymethyl-(E)-γ-methylallyl]-2,4,2',4'-tetrahydroxychalcone 11'-O-coumarate, isolicoflavonol, isoliquiritigenin, and
ixocarpalactone A are regarded as promising leads as potential cancer chemopreventive agents.
Answer 738:
A validated solid-phase extraction HPLC method for the simultaneous determination of the citrus flavanone aglycones
hesperetin and naringenin in urine. Kanaze, Feras Imad; Kokkalou, Eugene; Georgarakis, Manolis; Niopas, Ioannis.
Department of Pharmacy, School of Health Sciences, Aristotle University of Thessaloniki, Thessaloniki, Greece. Journal of
Pharmaceutical and Biomedical Analysis (2004), 36(1), 175-181. Publisher: Elsevier B.V., CODEN: JPBADA ISSN: 0731-7085.
Abstract
flavanone
A simple, specific, precise, accurate, and robust HPLC assay for the simultaneous anal. of hesperetin and naringenin in human urine
was developed and validated. Urine samples were incubated with β-glucuronidase/sulfatase and the analytes were isolated by
solid-phase extn. using C18 cartridges and sepd. on a C8 reversed phase column using a mixt. of methanol/water/acetic acid (40:58:2,
vol./vol./v) at 45°. The method was found to be linear in the 50-1200 ng/mL concn. range for both hesperetin and naringenin (r >
0.999). The accuracy of the method was greater than 94.8%, while the intra- and inter-day precision for hesperetin was better than 4.9
and 8.2%, resp. and for naringenin was better than 5.3 and 7.8%, resp. Recovery for hesperetin, naringenin and internal std.
7-ethoxycoumarin was greater than 70.9%. The method has been applied for the detn. of hesperetin and naringenin in urine samples
obtained from a male volunteer following a single 300 mg oral dose of each of the corresponding flavanone glycosides hesperidin and
naringin. The intra- and inter-day reproducibility through enzyme hydrolysis was less than 3.9% for both total (free + conjugated)
hesperetin and naringenin. Stability studies showed urine quality control samples to be stable for both hesperetin and naringenin
through three freeze-thaw cycles and at room temp. for 24 h (error ≤ 3.6%).
Answer 739:
A new dihydroflavone glycoside from Glycyrrhiza uralensis. Liu, Hong Xia; Lin, Wen Han; Yang, Jun Shan. Institute of
Medicinal Plant Development, Chinese Academy of Medical Science and Peking Union Medical College, Beijing, Peop. Rep. China.
Chinese Chemical Letters (2004), 15(8), 925-926. Publisher: Chinese Chemical Society, CODEN: CCLEE7 ISSN: 1001-8417.
Abstract
A new dihydroflavone glycoside was isolated from the underground parts of Glycyrrhiza uralensis. Its structure was elucidated as
7-hydroxyl-4'-O-β-D-(6''-O-α-hydroxylpropionyl) glucopyranosyl dihydroflavone by spectral methods.
Answer 740:
Isolation and structure elucidation of a flavanone, a flavanone glycoside and vomifoliol from Echiochilon fruticosum
growing in Tunisia. Hammami, S.; Ben Jannet, H.; Bergaoui, A.; Ciavatta, L.; Cimino, G.; Mighri, Z. Faculte des Sciences de
Monastir, Laboratoire de Chimie des Substances Naturelles et de Synthese Organique, Monastir, Tunisia. Molecules (2004), 9(7),
602-608. Publisher: Molecular Diversity Preservation International, CODEN: MOLEFW ISSN: 1420-3049.
http://www.mdpi.net/molecules/papers/90700602.pdf Journal; Online Computer File written in English. CAN 142:332890 AN
Abstract
A flavanone and a flavanone glycoside, together with vomifoliol, have been isolated for the first time from the aerial parts of the plant
Echiochilon fruticosum and identified. Their structures were established on the basis of spectroscopic measurements, mainly 2D NMR
using COSY, HMQC and HMBC expts.
Answer 741:
Comprehensive Study on Vitamin C Equivalent Antioxidant Capacity (VCEAC) of Various Polyphenolics in Scavenging a Free
Radical and its Structural Relationship. Kim, Dae-Ok; Lee, Chang. Department of Food Science and Technology, Cornell
University, Geneva, NY, USA. Critical Reviews in Food Science and Nutrition (2004), 44(4), 253-273. Publisher: Taylor &
flavanone
Francis, Inc., CODEN: CRFND6 ISSN: 1040-8398. Journal written in English. CAN 142:446241 AN 2004:690711 CAPLUS
Abstract
Antioxidant capacity for a wide range of natural or synthetic polyphenolics was comprehensively evaluated by vitamin C equiv.
antioxidant capacity (VCEAC) assay using free blue/green ABTS radicals. The polyphenolics tested are grouped into the following
categories: vitamins (β-carotene, α-tocopherol, vitamin A, and vitamin C), phenolic acids (benzoic acid, phenylacetic acid, cinnamic
acid, and their derivs.), flavonoids (anthocyanidin, flavanol, chalcone, flavanone, flavone, flavonol, isoflavone, and their derivs.),
synthetic food additives (BHA, BHT, TBHQ, and PG), and other misc. polyphenolics (ellagic acid, sesamol, eugenol, thymol, etc.). A
pos. linear relationship between VCEAC and the no. of free OH groups around the flavonoid framework was found, whereas, for
phenolic acids, the linear relationship was not as good as with the flavonoid aglycons. Groups of chems. having comparable structures
generally showed similar trends. Polyphenolics commonly showed a higher VCEAC compared to monophenolics. Compds. like gallic
acid with 3 vicinal hydroxy substitutions on the arom. ring in phenolic acids or like epigallocatechin with 3 vicinal hydroxy substitutions
on the B ring in flavonoids showed the highest antioxidant capacity among the groups. In the flavonoids, 2 characteristic chem.
structures were very important, the catechol moiety in the B ring and the 3-OH functional group in a chroman ring. Glycosylated
flavonoids showed less potent antioxidant capacity than their aglycon alone. Synthetic antioxidant food additives (BHA, TBHQ, and
BHT) conventionally used in the food industry were less effective antioxidants than ascorbic acid. Other naturally occurring
polyphenolics tested followed the expected general trends of phenolic acids and flavonoids.
Answer 742:
Synthesis of deuterium-labeled flavanones. Kagawa, Hitoshi; Takahashi, Tetsuya; Uno, Mariko; Ohta, Shigeru; Harigaya,
Yoshihiro. Department of Organic Synthesis, School of Pharmaceutical Sciences, Kitasato University, Tokyo, Japan. Chemical
& Pharmaceutical Bulletin (2004), 52(8), 953-956. Publisher: Pharmaceutical Society of Japan, CODEN: CPBTAL ISSN: 0009-2363.
Abstract
Deuterium incorporation at the C-3 position of flavanones was achieved by treatment of flavanones and 2'-hydroxychalcones with
D3PO4 and AcOD. The deuteration reaction mechanism for 2'-hydroxychalcones substrates is as follows. In the first step,
2'-hydroxychalcones cyclize to the corresponding flavanones by an intramol. Michael-type reaction. Then deuteriums are incorporated
into the flavanones via enolization.
Answer 743:
Effects of Dihydrogenation of Flavones and Number of Hydroxy Groups in the Molecules on Ocular Blood Flow in Rabbits
and Retinal Function Recovery in Rats. Xu, Xin-Rong; Park, Young-Hyun; Chiou, George C. Y. Institute of Ocular
Pharmacology and Department of Medical Pharmacology and Toxicology, Health Science Center College of Medicine, Texas A&M
University System, College Station, TX, USA. Journal of Ocular Pharmacology and Therapeutics (2004), 20(4), 311-320.
Publisher: Mary Ann Liebert, Inc., CODEN: JOPTFU ISSN: 1080-7683. Journal written in English. CAN 141:253664 AN
Abstract
Purpose: It has been found that the no. of hydroxy groups in the mol. of flavones and flavanones affect the ocular blood flow
flavanone
significantly. However, the effects of dihydrogenation of flavones into flavanones on ocular blood flow and retinal function recovery
have not been studied and required investigation. Methods: The colored microsphere technique and electroretinog. method were used
for the study of ocular blood flow and retinal function, resp. Results: Maximum effects on ocular blood flow were obtained when there
were 3 hydroxy groups in the mol. of flavones and flavanones. Dihydrogenation of flavones to flavanones increased the ocular blood
flow further. The same is true for retinal function recovery after ischemic insult. Conclusion: These results indicate that
hydrogenation is an excellent way to convert natural flavones into more potent compds. of flavanones.
Answer 744:
Flavonoids promote cell migration in nontumorigenic colon epithelial cells differing in Apc genotype: Implications of matrix
metalloproteinase activity. Fenton, Jenifer I.; Hord, Norman G. Department of Food Science and Human Nutrition, Michigan
State University, East Lansing, MI, USA. Nutrition and Cancer (2004), 48(2), 182-188. Publisher: Lawrence Erlbaum Associates,
Inc., CODEN: NUCADQ ISSN: 0163-5581. Journal written in English. CAN 142:211519 AN 2004:675950 CAPLUS (Copyright
Abstract
Colonic epithelial cell migration is required for movement up to the apex of the crypt and, hence, normal differentiated cell function.
This migratory phenotype is dependent upon wild-type adenomatous polyposis coli (Apc) expression. The purpose of this study is to
det. whether specific flavonoids induce cell migration in colon epithelial cells either wild type or heterozygous for Apc genotype.
Nontumorigenic murine colon epithelial cell lines with distinct Apc genotypes, young adult mouse colon (YAMC; Apc+/+) cells, and
Immortomouse/Min colon epithelial (IMCE; ApcMin/+) cells were used to assess the ability of specific flavonoids to induce cell
migration relative to migration induced by hepatocyte growth factor (HGF). The citrus flavanones naringenin and hesperetin did not
induce cell migration comparable with HGF in either cell type. However, the glycosylated forms of these flavanones, naringin and
hesperidin, induced migration differentially in YAMC and IMCE cells. Specifically, naringin and hesperidin induced the greatest
migratory response in IMCE cells at 1 μM (P < 0.01) and induced migration greater than untreated control cells (P < 0.05) but equal to
HGF-treated cells. In YAMC cells, hesperidin did not induce migration except at the 100-μM concn. Apigenin induced migration in
IMCE cells at 1 (P < 0.05) and 50 μM (P < 0.01) and did not induce migration in the YAMC cells. Catechin induced migration at the
highest concn. (300 μM) only in the IMCE cells, whereas epicatechin induced migration at the lowest concn. only (1 μM) in IMCE cells.
Overall, the glycosylated citrus flavanones induced the greatest migratory response at the lowest concn. in IMCE cells. Co-treatment
of IMCE cells with the global matrix metalloproteinase (MMP) inhibitor Ilomastat in the presence of naringin, hesperidin, or apigenin
demonstrated that flavonoid-induced migration was dependent on MMP activity.
Induction of the migratory phenotype by flavonoids in these models of preneoplastic epithelial cells suggests a novel
mechanism for colon cancer prevention.
Answer 745:
Biotransformations of citrus flavanone glycosides. Ellenrieder, Guillermo. National University of Salta - National Research
Council (CONICET), Argent. Editor(s): Pandey, Ashok. Concise Encyclopedia of Bioresource Technology (2004), 189-199.
Publisher: Haworth Press, Binghamton, N. Y CODEN: 69FTU3 Conference; General Review written in English. CAN 142:296810
Abstract
A review discussing the biotransformation of citrus flavanone glycoside contg. bioresources. Such transformations include enzymic
hydrolysis of flavanone glycosides to improve citrus product quality; hydrolysis to produce rhamnose, flavanone glucosides, and
flavanones; hydrogenation in basic medium to produce dihydrochalcone sweeteners; and enzymic glycosylation and esterification to
flavanone
synthesize new derivs.
Answer 746:
2,4,5-Triphenylspiro[pyrazolidine-3,3'-(4'-flavanone)]. Krishna, R.; Raj, S. Shanmuga Sundara; Velmurugan, D.; Fun, Hoong-Kun;
Manikandan, S.; Raghunathan, R. Department of Crystallography and Biophysics, University of Madras, Chennai, India. Acta
Crystallographica, Section C: Crystal Structure Communications (1999), C55(10), iii, IUC9900120. Publisher: Munksgaard
International Publishers Ltd., CODEN: ACSCEE ISSN: 0108-2701. http://journals.iucr.org/c/issues/1999/10/00/issconts.html Journal
Abstract
Crystals of the title compd. are orthorhombic, space group Pbca, with a 11.5244(2), b 19.1647(3), c 24.83550(10) .ANG.; Z = 8, dc =
1.23; R = 0.055, Rw(F2) = 0.128 for 4838 reflections. The compd. consists of a pyrazolidine ring, three arom. rings and a flavanone
moiety. The pyrazolidine ring is in an envelope conformation and the six membered ring in the flavanone moiety adopts sofa
conformation. The structure has a C-H⋅⋅⋅O-type intermol. interaction.
Answer 747:
Validated methods for the quantification of biologically active constituents of poplar-type propolis. Popova, Milena;
Bankova, Vassya; Butovska, Daniela; Petkov, Valentin; Nikolova-Damyanova, Boryana; Sabatini, Anna Gloria; Marcazzan, Gian Luigi;
Bogdanov, Stefan. Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulg.
Phytochemical Analysis (2004), 15(4), 235-240. Publisher: John Wiley & Sons Ltd., CODEN: PHANEL ISSN: 0958-0344. Journal
Abstract
The validation of rapid, low-cost spectrophotometric procedures for the quantification of the 3 main groups of bioactive substances
(flavones and flavonols, flavanones and dihydroflavonols, and total phenolics) in poplar-type propolis was performed. A
spectrophotometric assay based on the formation of an aluminum chloride complex was applied for the quantification of total flavones
and flavonols using galangin as std. Because of the high amt. of flavanones and dihydroflavonols in "poplar type" propolis, the
introduction of a distinct procedure for their quantification was considered of special significance and the DAB9 colorimetric method
was applied for the purpose. Total phenolic content was measured by the Folin-Ciocalteu procedure using a mixt. of pinocembrin and
galangin as a ref. The procedures were validated using a model mixt. of compds. representing the poplar-type propolis compn. as
found in previous studies. The accuracy (recovery) varied in the range 84-109%, and the relative std. deviation was 0.5-6.2%. The
developed spectrophotometric procedures were applied to six poplar type propolis samples. The results were verified independently by
a HPLC procedure. The 2 sets of results agreed satisfactory, as proven by Student's t-test.
Answer 748:
High-performance liquid chromatography methods for the analysis of adrenergic amines and flavanones in Citrus
aurantium L. var. amara. Pellati, Federica; Benvenuti, Stefania; Melegari, Michele. Department of Pharmaceutical Sciences,
University of Modena and Reggio Emilia, Modena, Italy. Phytochemical Analysis (2004), 15(4), 220-225. Publisher: John Wiley &
Sons Ltd., CODEN: PHANEL ISSN: 0958-0344. Journal written in English. CAN 141:195020 AN 2004:665481 CAPLUS
flavanone
Abstract
Reverse-phase HPLC coupled with photodiode array detection was used for the simultaneous sepn. and detn. of naturally occurring
adrenergic amines (octopamine, synephrine and tyramine) in fruits and dry exts. of Citrus aurantium L. var. amara and in herbal
medicines derived therefrom. Synephrine was the main component in fruits (0.10-0.35%) and in dry exts. (3.00-3.08%) and was
present in the range 0.25-0.99% in herbal medicines. Flavanones were analyzed in the same samples using a reverse-phase HPLC
technique which allowed the identification and quantification of neoeriocitrin, narirutin, naringin, hesperidin, neohesperidin, naringenin and
hesperetin. C. aurantium fruits and derivs. contained mainly glycosylated flavanones: in particular, naringin and neohesperidin were
found to be the major flavonoids and their concns. ranged from 1.80 to 26.30 and from 3.90 to 14.71 mg/g, resp. The levels of
aglycons were very low in all samples tested.
Answer 749:
Silacyclobutane oxidations in organic synthesis. Lam, Hubert T. C.; Dudley, Gregory B. Department of Chemistry and
Biochemistry, Florida State University, Tallahassee, FL, USA. Abstracts of Papers, 228th ACS National Meeting, Philadelphia,
PA, United States, August 22-26, 2004 (2004), ORGN-294. Publisher: American Chemical Society, Washington, D. C CODEN:
69FTZ8 Conference; Meeting Abstract written in English. AN 2004:658559 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
Due to their strain-release Lewis acidity, silacyclobutanes (siletanes) show enhanced reactivity in reactions such as the Mukaiyama
aldol and aldehyde allylation. In efforts to identify novel applications of these substrates in org. synthesis, we discovered that the
C-Si bond of a wide range (aryl, alkenyl, alkyl) of these silacycles can be mildly oxidized under the Tamao reaction protocol in high to
excellent yields. Preliminary results and progress in the synthesis of a natural flavanone 2 using this methodol. will be discussed.
Also, the design of a novel para-siletanylbenzyl (PSB) 3 protecting group will be mentioned.
Answer 750:
Absolute configuration and biological activity of biflavonoids from Rheedia acuminata. Li, Xing-Cong; Khan, Shabana I.;
Jacob, Melissa; Walker, Larry A.; Ferreira, Daneel. National Center for Natural Products Research, University of Mississippi,
University, MS, USA. Abstracts of Papers, 228th ACS National Meeting, Philadelphia, PA, United States, August 22-26, 2004
(2004), CELL-107. Publisher: American Chemical Society, Washington, D. C CODEN: 69FTZ8 Conference; Meeting Abstract
Abstract
Fatty acid synthase (FAS) which is a potential antifungal target was employed for bioactivity-guided fractionation of the ethanol ext. of
the twigs and leaves of Rheedia acuminata. Three flavanone-(3 8'')-flavone type biflavanoids, morelloflavone,
morelloflavone-7-sulfate and volkensiflavone-7-sulfate, one flavanone-(3 8'')-flavanone type biflavanoid, GB-2a-7-sulfate, and the
biflavone amentoflavone were isolated. They exhibited IC50 against FAS in a range of 3.5-22 μg/mL, but did not show activity in the
cell-based antifungal assays. However, the isolation of these compds. has permitted us to revisit the stereochem. of this
biosynthetically important group of natural products. Using spectroscopic methods and computational calcns., the abs. configurations
and conformations of the three flavanone-(3 8'')-flavone type biflavanoids were clearly defined. The abs. configuration of the more
complex biflavanoid, (+)-GB-2a-7-sulfate, was also deduced by interpretation of its CD data. In addn., the exchangeability of the C-3
flavanone
proton of the flavanone moiety of morelloflavone by deuterium in acetone-d6/D2O at ambient temp. with retention of configuration
indicates considerable chiral stability of this class of biflavonoids.
Answer 751:
Conformational analysis of the biflavanoid GB2 and a polyhydroxylated flavanone-chromone of Cratoxylum neriifolium.
Kumar, Vineet; Brecht, Volker; Frahm, August Wilhelm. Department of Pharmaceutical Chemistry, Freiburg, Germany. Planta
Medica (2004), 70(7), 646-651. Publisher: Georg Thieme Verlag, CODEN: PLMEAA ISSN: 0032-0943. Journal written in English.
Abstract
Three compds., namely the interesting biflavanonol GB-2 (naringenin I-3, II-8-dihydroquercetin (I)),
I-4',I-5,II-5,I-7,II-7-pentahydroxyflavanone(I-3,II-8)chromone [naringenin-(3→8) 5,7-dihydroxychromone (II)] and stigmasterol, were
isolated from the leaves of Cratoxylum neriifolium Kurz. I and II show rotameric behavior due to the presence of a single bond
between the highly substituted flavanone and flavanonol part and the flavanone and chromone part, resp. Complete NMR spectral
assignments of I and II were done at 27 °C and 90 °C for the first time followed by a study of conformational behavior at room temp.
by ROESY.
flavanone
OH
HO O
OH
OH O
HO O
OH
OH
OH O I
OH
HO O
OH O
HO O
OH O II
Answer 752:
Biochemical basis for processing of plants for medicinal products. Ezhov, V. N.; Polonskaya, A. K. Nikitskii Bot. Sad Nats.
Nauchnyi Tsentr, Ukr. Akad. Agrar. Nauk., Ukraine. Byulleten Glavnogo Botanicheskogo Sada (2003), 186 214-226. Publisher:
Nauka, CODEN: BYGBAA ISSN: 0366-502X. Journal written in Russian. CAN 142:225381 AN 2004:619701 CAPLUS
Abstract
Biochem. basis for processing of various pectin-contg. fruits was discussed. The chem. compn. of fruit of cherry plum, nectarine,
medlar and prickly pear was analyzed. The data on application of different substances for aromatization of wines and drinks are given.
Antioxidant activity of a no. of species of the Crimean flora was investigated. Method of bioelectrog. proved to be useful for estn. of
biol. and energy value in plant stuff and products.
Answer 753:
flavanone
High-performance liquid chromatographic enantioseparations on capillary columns containing monolithic silica modified
with cellulose tris(3,5-dimethylphenylcarbamate). Chankvetadze, Bezhan; Yamamoto, Chiyo; Tanaka, Nobuo; Nakanishi,
Kazuki; Okamoto, Yoshio. Molecular Recognition and Separation Science Laboratory, School of Chemistry, Tbilisi State University,
Tbilisi, Georgia. Journal of Separation Science (2004), 27(10-11), 905-911. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA,
Abstract
Monolithic capillary columns contg. native silica gel were modified with cellulose tris(3,5-dimethylphenylcarbamate) (CDMPC) and used
for enantiosepns. in capillary liq. chromatog. The method adopted for in situ enantioselective modification of monolithic fused silica
capillary columns by coating with CDMPC appears to be fairly simple and fast. High efficiency enantiosepns. of test racemic
compds. and several chiral drugs were achieved in a short time. It was possible to increase the amt. of chiral selector present by
multiple coating of monoliths with CDMPC. The baseline enantiosepn. of 2,2,2-trifluoro-1-(9-anthryl)ethanol was achieved in an anal.
time <30 s with this capillary column. Reproducible enantiosepns. were obtained when the chiral selector was removed from the
monolithic column by flushing it with appropriate solvent and the column recoated.
Answer 754:
Metabolic modifications of birch leaf phenolics by an herbivorous insect: Detoxification of flavonoid aglycons via
glycosylation. Salminen, Juha-Pekka; Lahtinen, Maria; Lempa, Kyoesti; Kapari, Lauri; Haukioja, Erkki; Pihlaja, Kalevi. Laboratory
of Environmental Chemistry, Department of Chemistry, University of Turku, Turku, Finland. Zeitschrift fuer Naturforschung, C:
Journal of Biosciences (2004), 59(5/6), 437-444. Publisher: Verlag der Zeitschrift fuer Naturforschung, CODEN: ZNCBDA ISSN:
Abstract
The metabolic modifications of birch (Betula pubescens) leaf phenolics in the digestive tract of its major defoliator, larvae of the
autumnal moth Epirrita autumnata, were studied. The main phenolic acids of birch, i.e., chlorogenic and p-coumaroylquinic acids, were
isomerized in the alk. digestive tract. Moreover, only 16 to 92% of the ingested amts. of chlorogenic acid were found in the feces of
individual larvae; the missing portion is possibly being used in the formation of reactive o-quinones. Water-sol. flavonoid glycosides
were mostly excreted unaltered. In contrast, lipophilic flavonoid aglycons were not excreted as such, but as glycosides after being
detoxified by E. autumnata via glycosylation. When the larvae were fed with leaf-painted acacetin and kaempferide, i.e., two naturally
occurring birch leaf flavonoid aglycons, acacetin-7-O-glucoside and kaempferide-3-O-glucoside appeared in larval feces as major
metabolites. However, the efficiency of aglycon glycosylation varied, ranging from 17 to 33%, depending on the aglycon and its
dietary level. There was also large variation in the efficiency of glycosylation, from 2 to 57%, among individual larvae. These results
demonstrate a compd.-specific metab. of phenolic compds., leading to different phenolic profiles in the insect gut compared to its leaf
diet.
Answer 755:
Optimization of chromatographic conditions in thin layer chromatography of flavonoids and phenolic acids. Medic-Saric,
Marica; Jasprica, Ivona; Smolcic-Bubalo, Asja; Mornar, Ana. Faculty of Pharmacy and Biochemistry, University of Zagreb, Zagreb,
flavanone
Croatia. Croatica Chemica Acta (2004), 77(1-2), 361-366. Publisher: Croatian Chemical Society, CODEN: CCACAA ISSN:
Abstract
Flavonoids are one of the largest groups of natural compds. known. They are supposed to have numerous physiol. activities. There
are many foods that contain flavonoids, but one of the most important sources of flavonoids is propolis. Besides flavonoids, phenolic
acids are the main active substances of propolis. The list of uses and prepns. of propolis is almost endless and demands an accurate
anal. method to define the substances in this natural product. It can be easily analyzed by chromatog. methods, but before testing a
new type of propolis it is opportune to optimize chromatog. conditions. The aim of this study is to optimize the chromatog. conditions
in TLC of flavonoids and phenolic acids, as std. compds. that may be present in Croatian propolis. The authors compared 9 different
mobile phases, using information theory and numerical taxonomy methods and applying the computer search program KT1, to find the
most appropriate mobile phase, the optimal combination of 2 and 3 mobile phases for sepn. of stds.
Answer 756:
Separation of Flavanone-7-O-glycoside Diastereomers and Analysis in Citrus Juices by Multidimensional Liquid

Chromatography Coupled with Mass Spectrometry. Aturki, Zeineb; Brandi, Valentina; Sinibaldi, Massimo. Istituto di
Metodologie Chimiche, CNR-Area della Ricerca di Roma, Rome, Italy. Journal of Agricultural and Food Chemistry (2004), 52(17),
Abstract
The major flavanone-7-O-glycoside constituents in citrus fruit juices (naringin, hesperidin, neohesperidin, narirutin, and eriocitrin) were
sepd. as diastereomers by multidimensional LC. The method consisted of coupling 2 HPLC columns: a reversed-phase (RP18) column
was used for the sepn. of flavanone glycosides, which were, then, individually switched into a carboxymethylated β-cyclodextrin
(β-CD)-based column and resolved as the corresponding stereoisomers. The method was used for the full anal. of flavanone
glycosides in fresh hand-squeezed and com. fruit juices by combining the quant. estn. with the diastereomeric anal. Quant. data were
in general consistent with previously reported data in this field. CC-LC isomer anal. was carried out by coupling the β-CD column with
a mass spectrometer operated with neg. ion electrospray ionization (ESI-MS). The results showed that hesperidin was present in orange
juices almost exclusively as the 2S isomer, whereas narirutin had mainly the 2R configuration. In grapefruit juices, (2S)-naringin
prevailed with the respect to the 2R isomer, whereas the opposite was true for narirutin. Lemon juices contained eriocitrin
stereoisomers in equal amt. (50% each), but hesperidin was almost exclusively found as the 2S isomer. Significant differences of the
diastereomeric ratios were obsd. between freshly squeezed juices and juices from com. sources.
Answer 757:
The inhibition of superoxide anion generation by neutrophils from Viscum articulactum. Leu, Yann-Lii; Kuo, Shih-Ming;
Hwang, Tsong-Long; Chiu, Shau-Ting. Graduate Institute of Natural Products, College of Medicine, Chang Gung University,
Tao-Yuan, Taiwan. Chemical & Pharmaceutical Bulletin (2004), 52(7), 858-860. Publisher: Pharmaceutical Society of Japan,
Abstract
flavanone
Two new flavanones, (2S)-pinocembrin 7-O-[β-D-apiosyl(1→2)]-β-D-glucoside (1), and (2S)-pinocembrin

7-O-[cinnamoyl(1→5)-β-D-apiosyl(1→2)]-β-D-glucoside (2) together with eighteen known compds., which include five known flavanones,
nine benzenoids, one inositol and three triterpenoids, were isolated and characterized from fresh Viscum articulactum. Structures of
new compds. were detd. by spectral anal. Among them, oleanolic acid (18) showed a significant inhibition effect on superoxide anion
generation by human neutrophils in response to formyl-L-methionyl L-leucyl-L-phenylalanine (fMLP).
Answer 758:
Chemical compositions of Syzygium Jambos (Linn)⋅Alston. Hoang, Van Luu; Nguyen, Quang Tue. Dept. Chem., Vinh
University, Vietnam. Tap Chi Phan Tich Hoa, Ly Va Sinh Hoc (2004), 9(1), 20-23, 19. Publisher: Vietnam Analytical Sciences
Society, CODEN: TCPTAH Journal written in Vietnamese. CAN 141:415578 AN 2004:595171 CAPLUS (Copyright (C) 2008
Abstract
The leaf essential oil of Syzygium Jambos (Linn)⋅Alston (Myrtaceae) was isolated by steam distn. and sepd. by GC. The sepd.
components were identified by GC/MS, the main components were α-caryophyllene, β-pinene, linalool, β-ocimene, α-terpineol,
γ-terpinen, trans-nerolidol. The pulp essential oil of Syzygium Jambos (Linn)⋅Alston contained nerolidol with high percentage (16.4 %).
The chem. compns. of petroleum ether and methanol exts. of the flower of Syzygium Jambos (Linn)⋅Alston were identified by GC/MS.
The main components were found to be flavonoids 8-hydroxy-6-methoxy flavanone, 5,7-dihydroxyflavanone,
6,8-dihydroxy-5-methylflavanone, 5-hydroxy, 7-methoxy, 6,8-di-Me flavanone, and 5,7-dimethoxy flavanone. The main components
of the petroleum ether ext. of the bark of Syzygium Jambos (Linn)⋅Alston were 9,12-octadecadienoic acid (23.5 %), 9-octadecenoic
acid (15.4 %) and n-hexadecanoic acid (13.7 %).
Answer 759:
Flavonoids from Spatholobus suberectus. Yoon, Jeong Seon; Sung, Sang Hyun; Park, Jong Hee; Kim, Young Choong.
College of Pharmacy and Research Institute of Pharmaceutical Science, Seoul National University, Seoul, S. Korea. Archives of
Pharmacal Research (2004), 27(6), 589-592. Publisher: Pharmaceutical Society of Korea, CODEN: APHRDQ ISSN: 0253-6269.
Abstract
Two pterocarpans [(6aR,11aR)-maackiain, (6aR,11aR)-medicarpin], one flavanone [(2S)-7-hydroxy-6-methoxy-flavanone], one

isoflavan (sativan) and two isoflavones (pseudobaptigenin, genistein) were isolated from the Spatholobus suberectus (Leguminosae).
Their chem. structures were detd. by comparison of their spectroscopic parameters of CD, EIMS, 1D-NMR and 2D-NMR with those
reported in the literatures. All of these compds. are reported for the first time from this plant.
Answer 760:
Cloning and sequence analysis of flower tissue-specific expression gene promoter PchsA from Petunia hybrida. Hong,
Yahui; Jiang, Hong; Xiao, Langtao; Huang, Huang; Zhang, Wen. Department of Biotechnology, HNAU, Changsha, Hunan Province,
Peop. Rep. China. Hunan Nongye Daxue Xuebao (2003), 29(6), 474-477. Publisher: Hunan Nongye Daxue Xuebao Bianjibu,
CODEN: HNDXFL ISSN: 1007-1032. Journal written in Chinese. CAN 141:289896 AN 2004:567363 CAPLUS (Copyright (C)
flavanone
Abstract
According to the sequence of flower tissue-specific expression gene CHSA promoter in Petunia hybrida reported by Ingrid M., we
designed and synthesized a pair of primers. With total DNA of Petunia hybrida used as template, we got a DNA fragment about 370
bp amplified by PCR procedure, reclaimed the product and cloned it into plasmid vector pUCm-T. We confirmed the recombinant after
transformation and filtration. Then the recombinant T-vectors were identified by restriction enzymes and subjected to sequence anal.
The result shows that this fragment's length is 370 bp. We use DSgene analyze software to analyze the sequence and find that it has
all the basic conservative sequences of a promoter, TATA box, CCAAT box, anther box, G-box, TACPyAT box, box1, box2, Capsite
etc. These sequences are totally the same as what is reported, and the fragment is proved to share 96% homol. with the reported
sequence by Internet BLAST program and DSgene analyze software.
Answer 761:
Flavonoid Distribution during the Development of Leaves, Flowers, Stems, and Roots of Rosmarinus officinalis. Postulation
of a Biosynthetic Pathway. Del Bano, Maria Jose; Lorente, Juan; Castillo, Julian; Benavente-Garcia, Obdulio; Marin, Maria Piedad;
Del Rio, Jose Antonio; Ortuno, Ana; Ibarra, Isidro. Research and Development Department, Nutrafur-Furfural Espanol S.A.,
Alcantarilla, Murcia, Spain. Journal of Agricultural and Food Chemistry (2004), 52(16), 4987-4992. Publisher: American Chemical
Abstract
The distribution of seven flavonoids, eriocitrin, luteolin 3'-O-β-D-glucuronide, hesperidin, diosmin, isoscutellarein 7-O-glucoside,
hispidulin 7-O-glucoside, and genkwanin, has been studied in Rosmarinus officinalis leaves, flowers, stems, and roots during plant
growth. The max. level reached by luteolin 3'-O-β-D-glucuronide in leaves during June-August suggests the existence of a delay
between the activation of the enzymes involved in the flavanone and flavone biosynthesis. The presence of hesperidin and diosmin in
the vascular system is significant, and hesperidin shows even higher levels than the phenolic diterpenes and rosmarinic acid. The
distribution of flavonoids obsd. in R. Officinalis suggests a functional and structural relationship between phytoregulators and
flavonoids, where flavonoids would be "protectors" of the activity of phytoregulators. A hypothesis for the general pathway of
biosynthesis of these compds. in plants of the family Labiatae is proposed.
Answer 762:
A new flavanone glycoside from leaves of Impatiens balsamina. Hasan, A.; Tahir, M. N.; Malik, A.; Sharif, C. A.; Khan, M. A.
Department of Chemistry, Quaid-i-Azam University, Islamabad, Pak. Journal of the Chemical Society of Pakistan (2004), 26(2),
167-170. Publisher: Chemical Society of Pakistan, CODEN: JCSPDF ISSN: 0253-5106. Journal written in English. CAN
Abstract
A new flavanone glycoside, naringenin-4'-O-β-D-glucuronopyranoside was isolated from leaves of Impatiens balsamina together with a
known but rare flavanone monoglycoside: naringenin 4'-O-β-D-glucopyranoside, four rare flavonol diglycosides: quercetin
3-O-α-L-rhamnopyranosyl(1→6)-β-D-galactopyranoside, kaempferol-3-O-α-L-rhamnopyranosyl-7-O-α-L-arabinopyranoside,
quercetin-3-O-β-D-xylopyranosyl(1→6)-β-D-glucopyranoside, quercetin-3-O-α-L-arabinopyranosyl(1→2)-β-D-glucopyranoside and three
flavanone
flavonol monoglycosides: kaempferol-7-O-α-L-rhamnopyranoside, kaempferol-7-O-β-D-allopyranoside and

quercetin-3-O-β-D-glucopyranoside. Their structures were detd. by means of co-chromatog., UV, EI-MS, FAB-MS and 1HNMR
spectroscopy.
Answer 763:
Structural requirements of flavonoids for increment of ocular blood flow in the rabbit and retinal function recovery in rat
eyes. Park, Young-Hyun; Xu, Xin-Rong; Chiou, George C. Y. Institute of Ocular Pharmacology and Department of Medical
Pharmacology and Toxicology, Texas A and M University College of Medicine, College Station, TX, USA. Journal of Ocular
Pharmacology and Therapeutics (2004), 20(3), 189-200. Publisher: Mary Ann Liebert, Inc., CODEN: JOPTFU ISSN: 1080-7683.
Abstract
We have recently reported that the effect of a flavonoid on ocular blood flow depends upon the no. of hydroxy (OH) groups in its
backbone structure. To elucidate the structural features on the no. and type of functional groups present in the flavonoid mol. plus the
no. of OH groups, flavonoids with four to five OH groups, with or without methoxy groups, were studied on their effects to affect the
ocular blood flow and the retinal function recovery. A colored microsphere technique was used to det. the ocular blood flow in albino
rabbit eyes and electroretinog. was used to measure the retinal function recovery. Flavonols with four free OH groups produced no
effects on the ocular blood flow (fisetin, kaempferol), whereas flavanone and flavones with four free OH groups and without the C2-C3
double bond produced the rapid increment on ocular blood flow (dihydrofisetin and luteolin, resp.). Similarly, flavonols with five free
OH groups produced no effects on the ocular blood flow (morin, quercetin). Yet, flavanone with five free OH groups and without the
C2-C3 double bond produced the rapid increment on ocular blood flow (dihydroquercetin). Flavanols with five free OH groups and
without the C2-C3 double bond and the carbonyl group produced no effects on the ocular blood flow (catechin). Flavonols with four
free OH groups and a methoxy group on the 7 position produced no effects on the ocular blood flow (Rhamnetin). Flavonols with four
free OH groups and a methoxy group at the 5 (5-methylquercetin) or 3' position (isorhamnetin) produced pos. effects on the ocular
blood flow also. Flavonol with five methoxy groups but no OH group produced pos. effects on the ocular blood flow
(pentamethylquercetin). Flavonols with an excessive no. of OH groups, having both a catechol-like structure in the C ring and a
catechol at the B ring, produced no effect on the ocular blood flow (rhamnetin, quercetin). Parallel results were obtained on retinal
function recovery after ischemic insult.
The presence of OH groups at certain positions and the double bond at C2-C3 in the flavonoid mols., which produces
lipophilic action, can affect the increment on ocular blood flow and retinal function recovery. O-methylation can increase
ocular blood flow and retinal function recovery as well.
Answer 764:
An intragenic tandem duplication in a transcriptional regulatory gene for anthocyanin biosynthesis confers pale-colored
flowers and seeds with fine spots in Ipomoea tricolor. Park, Kyeung-Il; Choi, Jeong-Dao; Hoshino, Atsushi; Morita, Yasumasa;
Iida, Shigeru. National Institute for Basic Biology, Okazaki, Japan. Plant Journal (2004), 38(5), 840-849. Publisher: Blackwell
Publishing Ltd., CODEN: PLJUED ISSN: 0960-7412. Journal written in English. CAN 141:289738 AN 2004:534817 CAPLUS
Abstract
While the wild-type morning glory (Ipomoea tricolor) displays bright-blue flowers and dark-brown seeds, its spontaneous mutant, Blue
Star, carrying the mutable ivory seed-variegated (ivs-v) allele, exhibits pale-blue flowers with a few fine blue spots and ivory seeds
with tiny dark-brown spots. The mutable allele is caused by an intragenic tandem duplication of 3.3 kbp within a gene for transcriptional
flavanone
activator contg. a basic helix-loop-helix (bHLH) DNA-binding motif. Each of the tandem repeats is flanked by a 3-bp sequence AAT,
indicating that the 3-bp microhomol. is used to generate the tandem duplication. The transcripts in the pale-blue flower buds of the
mutant contain an internal 583-bp tandem duplication that results in the prodn. of a truncated polypeptide lacking the bHLH domain.
The mRNA accumulation of most of the structural genes encoding enzymes for anthocyanin biosynthesis in the flower buds of the
mutant was significantly reduced. The transcripts identical to the wild-type mRNAs for the transcriptional activator were present
abundantly in blue spots of the variegated flowers, whereas the transcripts contg. the 583-bp tandem duplication were predominant in
the pale-blue background of the same flowers. The flower and seed variegations studied here are likely to be caused by somatic
homologous recombination between an intragenic tandem duplication in the gene encoding a bHLH transcriptional activator for
anthocyanin biosynthesis, whereas various flower variegations are reported to be caused by excision of DNA transposons inserted into
pigmentation genes.
Answer 765:
Total Synthesis of Flavocommelin, a Component of the Blue Supramolecular Pigment from Commelina communis, on the
Basis of Direct 6-C-Glycosylation of Flavan. Oyama, Kinichi; Kondo, Tadao. Chemical Instrument Center and Graduate School
of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya, Japan. Journal of Organic Chemistry (2004), 69(16),
5240-5246. Publisher: American Chemical Society, CODEN: JOCEAH ISSN: 0022-3263. Journal written in English. CAN
Abstract
We succeeded in a first total synthesis of flavocommelin (I), a component of the blue supramol. pigment, commelinin, from
Commelina communis, by direct 6-C-glycosylation of the flavan (II) using perbenzylglucosyl fluoride in the presence of MS 5 .ANG. in
CH2Cl2 and a catalytic amt. of BF3⋅Et2O. After 6-C-glycosylation of II, oxidn. with CAN to flavanone and subsequent
4'-O-glycosylation, promoted with a combination of BF3⋅Et2O and DTBMP, afforded diglucosylflavanone. DDQ oxidn. of
diglucosylflavanone. and deprotection successively gave I.
Answer 766:
Synthesis and Aromatase Inhibitory Activity of Novel Pyridine-Containing Isoflavones. Kim, Young-Woo; Hackett, John C.;
Brueggemeier, Robert W. Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University,
Columbus, OH, USA. Journal of Medicinal Chemistry (2004), 47(16), 4032-4040. Publisher: American Chemical Society,
CODEN: JMCMAR ISSN: 0022-2623. Journal written in English. CAN 141:225176 AN 2004:528519 CAPLUS (Copyright (C)
Abstract
Aromatase, a cytochrome P 450 hemoprotein that is responsible for estrogen biosynthesis by conversion of androgens into estrogens,
is an attractive target in the treatment of hormone-dependent breast cancer. As a result, a no. of synthetic steroidal or nonsteroidal
aromatase inhibitors have been successfully developed. In addn., there are several classes of natural products that exert potent
activities in aromatase inhibition, with the flavonoids being most prominent. Previous studies have exploited flavone and flavanone
scaffolds for the development of new aromatase inhibitors. In this paper, the design, synthesis, and biol. evaluation of a novel series
of 2-(4'-pyridylmethyl)thioisoflavones as the first example of synthetic isoflavone-based aromatase inhibitors is described.
Answer 767:
flavanone
High-performance liquid chromatographic enantioseparations on monolithic silica columns containing a covalently

attached 3,5-dimethylphenylcarbamate derivative of cellulose. Chankvetadze, Bezhan; Ikai, Tomoyuki; Yamamoto, Chiyo;
Okamoto, Yoshio. Molecular Recognition and Separation Science Laboratory, School of Chemistry, Tbilisi State University, Tbilisi,
Georgia. Journal of Chromatography, A (2004), 1042(1-2), 55-60. Publisher: Elsevier Science B.V., CODEN: JCRAEY ISSN:
Abstract
Covalent immobilization of 3,5-dimethylphenylcarbamate deriv. of cellulose was performed in situ onto native silica monoliths cladded
in a 50 mm × 4.6 mm polyether ether ketone HPLC column. The covalent attachment of cellulose deriv. at 16-19% (wt./wt.) was
performed via an epoxide moiety. The column obtained by this technique combines the high enantiomer-resolving ability of the
polysaccharide deriv. with favorable dynamic properties of monolithic HPLC columns. The covalent attachment of the cellulose deriv.
enables this column to be used in combination with the mobile phases which are incompatible with coated-type polysaccharide columns
due to soly. of chiral selector in some org. solvents.
Answer 768:
Herbivore-induced plant vaccination. Part II. Array-studies reveal the transience of herbivore-specific transcriptional
imprints and a distinct imprint from stress combinations. Voelckel, Claudia; Baldwin, Ian T. Max Planck Institute for
Chemical Ecology, Jena, Germany. Plant Journal (2004), 38(4), 650-663. Publisher: Blackwell Publishing Ltd., CODEN: PLJUED
SciFinder (R))
Abstract
Microarray technol. has given plant biologists the ability to simultaneously monitor changes in the expression of hundreds of genes,
and yet, to date, this technol. has not been applied to ecol. phenomena. In native tobacco (Nicotiana attenuata), prior attack of
sap-feeding mirids (Tupiocoris notatus) results in vaccination of the plant against subsequent attacks by chewing hornworms (Manduca
sexta). This vaccination is mediated by a combination of direct and indirect defenses and tolerance responses, which act in concert
with the attack preferences of a generalist predator. Here, we use microarrays enriched in herbivore-elicited genes with a principal
components anal. (PCA) to characterize transcriptional 'imprints' of single, sequential, or simultaneous attacks by these two main
herbivores of N. attenuata. The PCA identified distinctly different imprints left by individual attack from the two species after 24 h,
but not after 5 days. Moreover, imprints of sequential or simultaneous attacks differed significantly from those of single attack,
suggesting the existence of a distinct gene expression program responsive to the combination of biol. stressors. A dissection of the
transcriptional imprints revealed responses in direct and indirect defense genes that were well correlated with obsd. increases in
defense metabolites. Attack from both herbivores elicits a switch from growth- to defense-related transcriptional processes, and
herbivore-specific changes occur largely in primary metab. and signaling cascades. PCA of these polygenic transcriptional imprints
characterizes the ephemeral changes in the transcriptome that occur during the maturation of ecol. relevant phenotypic responses.
Answer 769:
New prenylated flavones from the roots of Ficus beecheyana. Lee, Ching-kuo; Lu, Chung-kuang; Kuo, Yuen-Hsiung; Chen,
Jian-Zhi; Sun, Guang-Zhong. Graduate Institute of Pharmacognosy Science, Taipei Medical University, Taipei, Taiwan. Journal of
the Chinese Chemical Society (Taipei, Taiwan) (2004), 51(2), 437-441. Publisher: Chinese Chemical Society, CODEN: JCCTAC
flavanone
SciFinder (R))
Abstract
Two new prenylated flavanones, ficubee A (I) and ficubee B (II), resp., as 7,8-(2,2-dimethylpyrano)-6-prenyl-5,3',4'-trihydroxyflavone
and 6,7-(2,2-dimethylpyrano)-8-prenyl-5,3',4'-trihydroxyflavone were isolated from the roots of Ficus beecheyana together with twelve
known compds.: β-sitosterol, 5-stigmasten-3β,7α-diol, 5-stigmasten-3β,7β-diol, 3β-hydroxystigmast-5-en-7-one,
4-hydroxybenzaldehyde, 4-hydroxy-3-methoxybenzaldehyde, 1-(4-hydroxyphenyl)-ethanone, 4-hydroxy-3-methoxybenzoic acid,
4-hydroxycinnamic acid, seseline, xanthyletin, and psoralene. The structures of these secondary metabolites were detd. by
spectroscopic means and in comparison with published data.
Me
Me OH
O O
OH
Me OH O
Me I
Me Me
OH
Me
Me O O
OH
OH O II
Answer 770:
Chemical components of Anaphalis sinica Hance. Hua, Yan; Wang, Han-Qing. State Key Laboratory of OSSO, Lanzhou
Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, Peop. Rep. China. Journal of the Chinese Chemical
Society (Taipei, Taiwan) (2004), 51(2), 409-415. Publisher: Chinese Chemical Society, CODEN: JCCTAC ISSN: 0009-4536.
Abstract
flavanone
Twenty components (including a new flavanone) were isolated and identified from the whole plant of Anaphalis sinica Hance. Their
structures were detd. on the basis of spectral anal. and chem. transformation. These components are
6-[(5-methyl-6-ethyl-4-hydroxy-pyrone-3-yl)-methylene]glabranine (I), kaempferol, tiliroside, quercetin, quercetin-3-O-β-D-glucoside,
scutellarin , 5,7-dihydroxy-8-methoxyflavone, 5,7-dihydroxy-4'-methoxy-flavone-7-O-α-L-rhamnopyranosyl(1→6)-β-D-glucopyranoside,
helipyrone , 4'-hydroxydehydrokawain, panamin (II), ursolic acid, pomolic acid, 3-acetyloleanolic acid, a mixt. of
N-(2-hydroxy-acyl)-4-hydroxy-8(E)-ene-sphingenine, O-methyl-D-inositol, a mixt. of β-sitosterol and stigmasterol and a mixt. of
daucosterol and stigmasterol-β-D-glucoside. Among them, I is a new compd., and 13CNMR data of II is reported for the first time.
Me Me
HO O
Me OH
Et CH 2
O OH O
O I
Answer 771:
RNase P as a tool for disruption of gene expression in maize cells. Rangarajan, Sunita; Raj, M. L. Stephen; Hernandez, J.
Marcela; Grotewold, Erich; Gopalan, Venkat. Department of Biochemistry, The Ohio State University, Columbus, OH, USA.
Biochemical Journal (2004), 380(3), 611-616. Publisher: Portland Press Ltd., CODEN: BIJOAK ISSN: 0264-6021. Journal written in
Abstract
RNase P, a ribonucleoprotein responsible for the 5' maturation of precursor tRNAs (ptRNAs) in all organisms, can be enticed to cleave
any target mRNA that forms a ptRNA-like structure and sequence-specific complex when bound to an RNA, termed the EGS (external
guide sequence). In the present study, F3H (flavanone 3-hydroxylase), a key enzyme in the flavonoid biosynthetic pathway that
participates in the formation of red-colored anthocyanins, was used as a target for RNase P-mediated gene disruption in maize cells.
Transient expression of an EGS complementary to the F3H mRNA resulted in suppression of F3H to 29% of the control, as indicated
by a reduced no. of anthocyanin-accumulating cells. This decrease was not obsd. in expts. where a disabled mutant EGS was
expressed. Our results demonstrate the potential of employing plant RNase P, in the presence of an appropriate gene-specific EGS,
as a tool for targeted degrdn. of mRNAs.
Answer 772:
Enzymic acylation of flavonoids. Moussou, Philippe; Falcimaigne, Aude; Pauly, Gilles; Ghoul, Mohamed; Engasser, Jean-Marc;
Ardhaoui, Melika. (Cognis France S.A., Fr.). Eur. Pat. Appl. (2004), 11 pp. CODEN: EPXXDW EP 1426445 A1 20040609
Designated States R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT, IE, SI, LT, LV, FI, RO, MK, CY, AL, TR,
BG, CZ, EE, SK. Patent written in German. Application: EP 2002-292969 20021203. Priority: . CAN 141:5893 AN 2004:470353
flavanone

EP 1426445 A1 20040609 EP 2002-292969 20021203
TR, BG, CZ, EE, SK
WO 2004050889 A2 20040617 WO 2003-EP13143 20031122
WO 2004050889 A3 20040812
W: JP, KR, US
RW: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IT, LU, MC, NL, PT, RO, SE, SI,
SK, TR
EP 1567655 A2 20050831 EP 2003-812154 20031122
HU, SK
JP 2006508654 T 20060316 JP 2004-556169 20031122
US 20060115880 A1 20060601 US 2005-537627 20050603
EP 2002-292969 A 20021203
WO 2003-EP13143 W 20031122
Abstract
A process is provided for the enzymic acylation of glycosylated flavonoids. Thus, rutin was acylated with palmitic acid by the
immobilized lipase Novozyme 435 in a tert-amyl alc. solvent system. The reaction was conducted at 60 °C under vacuum (150 mbar).
Water was removed from the gas phase by a mol. sieve. After 48 h reaction time, 90% of the substrates were consumed. The
enzyme was removed by filtration, and unreacted substrates were removed by solvent extn.
Answer 773:
Liquid phase reaction of 2'-hydroxyacetophenone and benzaldehyde over ZSM-5 catalysts. Saravanamurugan, S.;
Palanichamy, M.; Arabindoo, Banumathi; Murugesan, V. Department of Chemistry, Anna University, Chennai, India. Journal of
Molecular Catalysis A: Chemical (2004), 218(1), 101-106. Publisher: Elsevier Science B.V., CODEN: JMCCF2 ISSN: 1381-1169.
Abstract
The reaction of 2'-hydroxyacetophenone with benzaldehyde was studied over H-ZSM-5, Mg-ZSM-5 and Ba-ZSM-5 catalysts at 140°.
The products were 2'-hydroxychalcone and flavanone. The conversion of 2'-hydroxyacetophenone increased with time and attained a
max. of 40-50% conversion over all the catalysts. Though the yield of chalcone and flavanone increased with increase in time, the
yield of flavanone was less than 2'-hydroxychalcone over all the catalysts. The order of activity of the catalysts was Mg-ZSM-5 >
Ba-ZSM-5 > H-ZSM-5. The influence of temp. in the range of 100-160° on conversion and products yield was studied over Mg-ZSM-5.
flavanone
The increase in conversion was small between 100 and 120°, but above 120 °C there was a marked increase in conversion. The
optimal catalyst loading was found to be 0.75 g for 10 mmol reactants. Study of influence of time on Mg-ZSM-5 at 160° revealed a
rapid increase in conversion and products yield up to 3 h and a steady state afterwards. The role of solvent in this reaction was
studied with DMSO, nitrobenzene and a mixt. of DMSO and nitrobenzene. High conversion was obsd. with DMSO.
Answer 774:
First bacterial chalcone isomerase isolated from Eubacterium ramulus. Herles, Claudia; Braune, Annett; Blaut, Michael.
Abteilung Gastrointestinale Mikrobiologie, Deutsches Institut fuer Ernaehrungsforschung Potsdam-Rehbruecke, Nuthetal, Germany.
Archives of Microbiology (2004), 181(6), 428-434. Publisher: : Springer-Verlag, CODEN: AMICCW ISSN: 0302-8933. Journal
Abstract
The human fecal anaerobe, E. ramulus, is capable of degrading various flavonoids, including the flavone, naringenin. The 1st step in
the proposed degrdn. pathway is the isomerization of naringenin to the corresponding chalcone. Here, cell-free exts. of E. ramulus
were found to exhibit chalcone isomerase (I) activity. I from E. ramulus was purified to homogeneity. Its apparent mol. wt. was estd.
to be 136 and 129 kDa according to gel filtration and native PAGE, resp. I was composed of a single type of subunit of 30 kDa mol.
wt. Purified I catalyzed the isomerization of naringenin chalcone, isoliquiritigenin, and butein, 3 chalcones that differ in their
hydroxylation pattern. N-bromosuccinimide, but also naringenin and phloretin, inhibited purified I considerably. This is the 1st report of
a bacterial I. The physiol. function of the purified enzyme was unclear, but an involvement in the conversion of the flavanone,
naringenin, to the chalcone was proposed. The N-terminal amino acid sequence (15 residues) of I was detd. and showed no identity
with known protein sequences in databases.
Answer 775:
The effect of naringin, a bioflavonoid on ischemia-reperfusion induced renal injury in rats. Singh, Devinder; Chopra,
Kanwaljit. University Institute of Pharmaceutical Sciences, Pharmacology Division, Panjab University, Chandigarh, India.
Pharmacological Research (2004), 50(2), 187-193. Publisher: Elsevier, CODEN: PHMREP ISSN: 1043-6618. Journal written in
Abstract
There is increasing evidence to suggest that toxic oxygen radicals play a role in the pathogenesis of ischemia/reperfusion (I/R) injury
in the kidney. This study was designed to investigate the effects of naringin (Ng), a bioflavonoid in I/R induced renal failure in rats.
The protective effect of naringin against the damage inflicted by reactive oxygen species (ROS) during renal I/R was investigated in
Sprague-Dawley rats using histopathol. and biochem. parameters. In one set of expts. animals were unilaterally nephrectomized, and
subjected to 45 min of left renal pedicle occlusion and in another set both the renal pedicles were occluded for 45 min followed by 24 h
of reperfusion. Naringin (400 mg kg-1, p.o.) was administered 60 min prior to ischemia. At the end of the reperfusion period, rats were
sacrificed. Thiobarbituric acid reactive substances (TBARS), reduced glutathione (GSH) levels, catalase (CAT), and superoxide
dismutase (SOD) activities were detd. in renal tissue. Serum creatinine and blood urea nitrogen (BUN) concns. were measured for the
evaluation of renal function. Ischemic control animals demonstrated severe deterioration of renal function, renal morphol. and a
significant renal oxidative stress. Pretreatment of animals with naringin markedly attenuated renal dysfunction, morphol. alterations,
reduced elevated TBARS levels and restored the depleted renal antioxidant enzymes. The findings imply that ROS play a causal role
in I/R induced renal injury and naringin exert renoprotective effects probably by the radical scavenging and antioxidant activities.
Answer 776:
flavanone
Synthesis of paramagnetic and diamagnetic flavones and flavanones. Kalai, Tamas; Kulcsar, Gyozo; Osz, Erzsebet; Jeko,
Jozsef; Suemegi, Balazs; Hideg, Kalman. Institute of Organic and Medicinal Chemistry, University of Pecs, Pecs, Hung.
ARKIVOC (Gainesville, FL, United States) (2004), (7), 266-276. Publisher: Arkat USA Inc., CODEN: AGFUAR
http://www.arkat-usa.org/ark/journal/2004/Antus/SA-1108B/1108B.pdf Journal; Online Computer File written in English. CAN
Abstract
Paramagnetic and diamagnetic flavone and flavanone derivs. modified on the C or B rings were synthesized by condensation,
Sonogashira reaction, lithiation, and the Baker-Venkataraman procedure. Thus, reacting aldehyde I with Ag2O/NaOH/THF gave the
acid, which was condensed with 2,6-dihydroxyacetophenone to give (pyrrolidinylphenyl)chromene II and the biradical III.
OH O
Me Me
Me N O
Me
O⋅ H
N Me
Me
O I O⋅ II
O
OH O Me
N Me
Me
O⋅
O
Me
N Me
Me
O⋅ III
Answer 777:
Microwave-induced, solvent-free transformations of benzoheteracyclanones by HTIB (Koser's reagent). Patonay, Tamas;

Levai, Albert; Riman, Eva; Varma, Rajender S. Department of Organic Chemistry, University of Debrecen, Debrecen, Hung.
ARKIVOC (Gainesville, FL, United States) (2004), (7), 183-195. Publisher: Arkat USA Inc., CODEN: AGFUAR
http://www.arkat-usa.org/ark/journal/2004/Antus/SA-1044B/1044B.pdf Journal; Online Computer File written in English. CAN
flavanone
Abstract
The microwave-activated reactions of [hydroxy(tosyloxy)iodo]benzene (HTIB) with various chromanones, thiochromanones and
dihydroquinolones under solvent-free conditions have been studied. In addn. to the common dehydrogenation reaction, 2,3-migration
also has been obsd. in the case of flavanone and 2,2-disubstituted chromanones. 3-Tosyloxychromanones were isolated from the
reaction of chromanone and 2-methylchromanone for the first time. Substrates with nucleophilic heteroatoms such as
thiochromanones and 2-phenyl-2,3-dihydro-4-quinolone reacted by electrophilic attack of the heteroatom.
Answer 778:
Antimalarial activity of lavandulyl flavanones isolated from the roots of Sophora flavescens. Kim, Youn Chul; Kim,
Hye-Sook; Wataya, Yusuke; Sohn, Dong Hwan; Kang, Tai Hyun; Kim, Myung Soo; Kim, Yong Man; Lee, Geon-Mok; Chang, Jong-Duk;
Park, Hyun. College of Pharmacy, Wonkwang University, Iksan, S. Korea. Biological & Pharmaceutical Bulletin (2004), 27(5),
748-750. Publisher: Pharmaceutical Society of Japan, CODEN: BPBLEO ISSN: 0918-6158. Journal written in English. CAN
Abstract
Four lavandulyl flavanones, (2S)-2'-methoxykurarinone (1), sophoraflavanone G (2), leachianone A (3), and (-)-kurarinone (4), which are
isolated from the roots of Sophora flavescens were tested for in vitro antimalarial activity against Plasmodium falciparum. Compds.
1-3 showed moderate antimalarial activities with EC50 values of 2.4×10-6, 2.6×10-6, and 2.1×10-6M, resp. These compds. did not
show selective toxicity against P. falciparum in the toxicity test on mouse mammalian tumor cells, however, it is suggested that the
position of methoxyl groups in flavanone skeleton plays an important role on antimalarial activity.
Answer 779:
Structurally related antitumor effects of flavanones in vitro and in vivo: involvement of caspase 3 activation, p21 gene
expression, and reactive oxygen species production. Shen, Shing-Chuan; Ko, Ching Huai; Tseng, Shi-Wen; Tsai, Shu-Huei;
Chen, Yen-Chou. School of Medicine, Department of Dermatology, Taipei Medical University, Taipei, Taiwan. Toxicology and
Applied Pharmacology (2004), 197(2), 84-95. Publisher: Elsevier Science, CODEN: TXAPA9 ISSN: 0041-008X. Journal written in
Abstract
Flavonoids exist extensively in plants and Chinese herbs, and several biol. effects of flavonoids have been demonstrated. The
antitumor effects in colorectal carcinoma cells (HT29, COLO205, and COLO320HSR) of eight flavanones including flavanone, 2'-OH
flavanone, 4'-OH flavanone, 6-OH flavanone, 7-OH flavanone, naringenin, naringin, and taxifolin were investigated. Results of the
MTT assay indicate that 2'-OH flavanone showed the most potent cytotoxic effect on these three cells, and cell death induced by
2'-OH flavanone was via the occurrence of DNA ladders, apoptotic bodies, and hypodiploid cells, all characteristics of apoptosis.
Induction of caspase 3 protein processing and enzyme activity assocd. with cleavage of poly(ADP-ribose) polymerase (PARP) was
identified in 2'-OH flavanone-treated cells, and a peptidyl inhibitor (Ac-DEVD-FMK) of caspase 3 attenuated the cytotoxicity of 2'-OH
flavanone in COLO205 and HT-29 cells. Elevation of p21 (but not p53) and a decrease in Mcl-1 protein were found in 2'-OH
flavanone-treated COLO205 and HT-29 cells. Elevation of intracellular reactive oxygen species (ROS) was detected in 2'-OH
flavanone-treated cells by the 2',7'-dichlorodihydrofluorescein diacetate (DCHF-DA) assay, and ROS scavengers including
4,5-dihydro-1,3-benzene disulfonic acid (tiron), catalase, superoxide dismutase (SOD), and pyrrolidine dithiocarbamate (PDTC)
suppressed the 2'-OH flavanone-induced cytotoxic effect. S.c. injection of COLO205 induced tumor formation in nude mice, and
flavanone
2'-OH flavanone showed a significant inhibitory effect on tumor formation. The appearance of apoptotic cells with H&E staining, and
an increase in p21, but not p53, protein by immunohistochem. were obsd. in tumor tissues under 2'-OH flavanone treatment.
Primary tumor cells (COLO205-X) derived from a tumor specimen elicited by COLO205 were established, and 2'-OH
flavanone showed an significant apoptotic effect in COLO205-X cells in accordance with the appearance of DNA ladders,
caspase 3 protein processing, PARP protein cleavage, and increasing p21 protein. These results revealed in vitro, ex
vivo, and in vivo antitumor activities of 2'-OH flavanone via apoptosis induction, and indicates that 2'-OH flavanone is
an active compd. worthy of development for cancer chemotherapy.
Answer 780:
The A-ring specific hydroxylation of flavonols in position 6 in Tagetes sp. is catalyzed by a cytochrome P450 dependent
monooxygenase. Halbwirth, Heidrun; Forkmann, Gert; Stich, Karl. Institute for Technical BioScience, Technical University of
Vienna, Vienna, Austria. Plant Science (Amsterdam, Netherlands) (2004), 167(1), 129-135. Publisher: Elsevier, CODEN:
PLSCE4 ISSN: 0168-9452. Journal written in English. CAN 141:203321 AN 2004:404607 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Yellow flavonols represent important plant pigments in Asteraceae. In contrast to common flavonols, they show addnl. hydroxyl
groups in position 6 and/or 8 of the arom. A-ring in addn. to the basic 5,7-hydroxylation pattern. A novel flavonol 6-hydroxylase (F6H)
introducing a hydroxyl group in position 6 of quercetin was demonstrated in enzyme prepns. from petals of Tagetes patula and Tagetes
erecta. The enzyme was classified as cytochrome P 450 dependent monooxygenase by photoreversible carbon monoxide inhibition,
inhibition by NADPH-cytochrome P 450 reductase specific antibodies and cytochrome P 450 specific inhibitors. The flavone luteolin
was barely accepted as a substrate. Methylated flavonols, quercetin 7-O-glucoside, flavanones, and dihydroflavonols were not
accepted as substrates. The presence of the enzyme was demonstrated in various varieties showing different coloration.
Answer 781:
Facile, high-yield, regioselective synthesis of ortho-nitrophenols using cerium (IV) ammonium nitrate. Sathunuru,
Ramadas; Rao, U. Narasimha; Biehl, Ed. Chem. Dep., Southern Methodist Univ., Dallas, TX, USA. ARKIVOC (Gainesville, FL,
United States) (2003), (15), 124-133. Publisher: Arkat USA Inc., CODEN: AGFUAR
http://arkat-usa.org/ark/journal/2003/General_Part(xv)/03-918D/918D.pdf Journal; Online Computer File written in English. CAN
Abstract
Certain phenols possessing at least one unsubstituted ortho position have been found to undergo rapid, regioselective ortho nitration
with CAN (cerium (IV) ammonium nitrate) in the presence of NaHCO3 at room temp. to yield o-nitrophenols in high yields.
Substituents tolerating these nitration conditions ranged from the activating methoxy and Me groups to the moderately deactivating Cl,
Br, CHO and CO2Me groups. In contrast, phenols that contained a strongly deactivating group such as nitro or cyano or
2,6-disubstituted phenols were not nitrated by the CAN/NaHCO3 reagent. More complex nitrophenols such as
6-hydroxy-5-nitro-1,3-benzoxathiol-2-one, 7-hydroxy-6-nitro-3,4,8-trimethylcoumarin, 6-hydroxy-5-flavanone,
1-(4-hydroxy-3-nitrophenyl)-1H-tetrazole-5-thiol, 2-(2-hydroxy-3-nitrophenyl)benzoxazole were also prepd. in good yields by the
CAN/NaHCO3 reagent.
Answer 782:
flavanone
Synthesis of Racemic and Enantiomerically Enriched α-Oxyfunctionalized Benzocyclanones and Chromanones by

Dimethyldioxirane and Dimethyldioxirane/Mn(III) salen System. Patonay, Tamas; Jekoe, Jozsef; Kiss-Szikszai, Attila; Levai,
Albert. Department of Organic Chemistry, University of Debrecen, Debrecen, Hung. Monatshefte fuer Chemie (2004), 135(6),
743-756. Publisher: Springer-Verlag Wien, CODEN: MOCMB7 ISSN: 0026-9247. Journal written in English. CAN 141:332012 AN
Abstract
Enolacetates of benzocyclanones and chromanones were synthesized and treated with dimethyldioxirane and the asym. oxidizing
system dimethyldioxirane/chiral, non-racemic Mn(III) salen complex/axial ligand. The latter reagent resulted in the corresponding
enantiomerically enriched cyclic α-hydroxy ketones and their acetates in moderate-to-good yields and modest enantioselectivity under
mild and neutral conditions from tetralone and chromanone. On the contrary, flavanone provided poor yields due to the competitive
C-H insertion at position 2. The use of (R,R)-Mn(III) salen catalyst induced an S abs. configuration at the position α in the whole
series.
Answer 783:
Nutritional Flavonoids Modulate Estrogen Receptor α Signaling. Virgili, Fabio; Acconcia, Filippo; Ambra, Roberto; Rinna,
Alessandra; Totta, Pierangela; Marino, Maria. Department of Biology, University 'Roma Tree', Rome, Italy. IUBMB Life (2004),
56(3), 145-151. Publisher: Taylor & Francis Ltd., CODEN: IULIF8 ISSN: 1521-6543. Journal written in English. CAN 140:399573
Abstract
Estrogen receptor α (ERα) mediates 17β-estradiol (E2) actions through the transcription of E2-sensitive target genes. In addn., rapid
non-genomic signaling (e.g., MAPK/ERK) occurs. It is now well accepted that these rapid membrane-initiated responses account for
E2-related cancer. Beside many beneficial effects on human health, nutritional flavonoids exert protective and anticarcinogenic
effects on E2-related cancer. The mechanism underlying these effects seems to be related to flavonoids antioxidant properties and/or
to their ability to alter signal transduction protein kinases. In addn., an antiestrogenic activity has been proposed but not yet defined.
However, the identification and characterization of the responsible mechanisms for flavonoid antitumoral effects is poorly understood.
Here, we investigated the possibility that the antimitogenic effects of flavonoids are transduced by modulating ERα-mediated rapid
signaling. The ability of two flavonoids, the flavanone naringenin and the flavanol quercetin, with respect of E2, to induce ERα
activities has been studied in the human cervix epitheloid carcinoma cell line (HeLa) devoid of any estrogen receptors and rendered
E2-sensitive by transient transfection with a human ERα expression vector. Our results indicate that flavonoids act as E2 mimetic on
ERα transcriptional activity, whereas they impair the activation of rapid signaling pathways committed to E2-induced proliferation. The
resulting decoupling of ERα signal transduction could be proposed as a new mechanism in the protective effects of flavonoids against
E2-related cancer.
Answer 784:
Quantitative determination of astilbin in rabbit plasma by liquid chromatography. Guo, Jianming; Xu, Qiang; Chen, Ting.
School of Life Sciences, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, Peop. Rep. China.
flavanone
Abstract
A simple method for detg. the concn. of astilbin, a flavanone, in rabbit plasma was developed. After liq.-liq. extn., the flavanone was
detected by HPLC on a 4.6-μm octadecyl-silica column (Nova-Pak C-18) at 291 nm. Linear calibration graphs for astilbin were
constructed from 0.44 to 22.17 μM. The limit of quantitation was 0.44 μM in plasma. The method was applied to pharmacokinetic
studies after a single i.v. and an oral administration of the compd. to rabbits.
Answer 785:
Cloning and over-expression of a cDNA encoding a polyketide synthase from Cannabis sativa. Raharjo, Tri J.; Chang,
Wen-Te; Verberne, Marianne C.; Peltenburg-Looman, Anja M. G.; Linthorst, Huub J. M.; Verpoorte, Robert. Department of Chemistry,
Gadjah Mada University, Yogyakarta, Indonesia. Plant Physiology and Biochemistry (Amsterdam, Netherlands) (2004), 42(4),
291-297. Publisher: Elsevier, CODEN: PPBIEX ISSN: 0981-9428. Journal written in English. CAN 141:49452 AN 2004:363040
Abstract
A polyketide synthase has been suggested to play an important role in cannabinoid biosynthesis in Cannabis sativa L. This enzyme
catalyzes the biosynthesis of olivetolic acid, one of the precursors for cannabinoid biosynthesis. Using a reverse
transcriptase-polymerase chain reaction (RT-PCR) based on the DNA homol. of chalcone synthase (EC 2.3.1.156) and valerophenone
synthase (EC 2.3.1.156) of hop (Humulus lupulus), a cDNA encoding a polyketide synthase in C. sativa was identified. The coding
region of the gene is 1170 bp long encoding a 389 amino acid protein of a predicted 42.7 kDa mol. mass and with a pI of 6.04. The
gene shares a high homol. with a chalcone synthase gene of H. lupulus, 85% and 94% homol. on the level of DNA and protein, resp.
Over-expression of the construct in Escherichia coli M15 resulted in a 45 kDa protein. The protein has chalcone synthase activity as
well as valerophenone synthase activity, a chalcone synthase-like activity. Using n-hexanoyl-CoA and malonyl-CoA as substrates did
not give olivetol or olivetolic acid as a product.
Answer 786:
Supported choline hydroxide (ionic liquid) as heterogeneous catalyst for aldol condensation reactions. Abello, Sonia;
Medina, Francisco; Rodriguez, Xavier; Cesteros, Yolanda; Salagre, Pilar; Sueiras, Jesus E.; Tichit, Didier; Coq, Bernard. Dept. de
Quimica i Enginyeria Quimica, Universitat Rovira i Virgili, Tarragona, Spain. Chemical Communications (Cambridge, United
Kingdom) (2004), (9), 1096-1097. Publisher: Royal Society of Chemistry, CODEN: CHCOFS ISSN: 1359-7345. Journal written in
Abstract
Choline hydroxide was used as a basic catalyst for aldol condensation reactions to produce new C-C bonds between several ketones
and aldehydes. Choline supported on MgO exhibited higher TOF values than other well known basic catalysts in these reactions.
Answer 787:
flavanone
Antifungal chalcones and new caffeic acid esters from Zuccagnia punctata acting against soybean infecting fungi. Svetaz,
Laura; Tapia, Alejandro; Lopez, Silvia N.; Furlan, Ricardo L. E.; Petenatti, Elisa; Pioli, Rosanna; Schmeda-Hirschmann, Guillermo;
Zacchino, Susana A. Pharmacognosy School of Biochemical and Pharmaceutical Sciences, National University of Rosario,
Rosario, Argent. Journal of Agricultural and Food Chemistry (2004), 52(11), 3297-3300. Publisher: American Chemical Society,
Abstract
The crude methanolic ext. of Zuccagnia punctata was active toward the fungal pathogens of soybean Phomopsis longicolla and
Colletotrichum truncatum. Assay-guided fractionation led to the isolation of two chalcones, one flavanone, and a new caffeoyl ester
deriv. (I) as the compds. responsible for the antifungal activity. Another new caffeoyl ester deriv. was isolated from the antifungal
chloroform ext. but proved to be inactive against the soybean-infecting fungi up to 50 μg/mL.
HO OH
O
OH
Me O I
Answer 788:
Naringenin Inhibits Glucose Uptake in MCF-7 Breast Cancer Cells: A Mechanism for Impaired Cellular Proliferation.
Harmon, Anne W.; Patel, Yashomati M. Department of Nutrition, University of North Carolina School of Public Health, Chapel Hill,
NC, USA. Breast Cancer Research and Treatment (2004), 85(2), 103-110. Publisher: Kluwer Academic Publishers, CODEN:
BCTRD6 ISSN: 0167-6806. Journal written in English. CAN 141:405701 AN 2004:343882 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Certain flavonoids inhibit glucose uptake in cultured cells. In this report, we show that the grapefruit flavanone naringenin inhibited
insulin-stimulated glucose uptake in proliferating and growth-arrested MCF-7 breast cancer cells. Our findings indicate that naringenin
inhibits the activity of phosphoinositide 3-kinase (PI3K), a key regulator of insulin-induced GLUT4 translocation, as shown by impaired
phosphorylation of the downstream signaling mol. Akt. Naringenin also inhibited the phosphorylation of p44/p42 mitogen-activated
protein kinase (MAPK). Inhibition of the MAPK pathway with PD98059, a MAPK kinase inhibitor, reduced insulin-stimulated glucose
uptake by approx. 60%. The MAPK pathway therefore appears to contribute significantly to insulin-stimulated glucose uptake in breast
cancer cells. Importantly, decreasing the availability of glucose by lowering the glucose concn. of the culture medium inhibited
proliferation, as did treatment with naringenin. Collectively, our findings suggest that naringenin inhibits the proliferation of MCF-7 cells
via impaired glucose uptake. Because a physiol. attainable dose of 10 μM naringenin reduced insulin-stimulated glucose uptake by
nearly 25% and also reduced cell proliferation, naringenin may possess therapeutic potential as an anti-proliferative agent.
Answer 789:
flavanone
Flavonoid methylation: a novel 4'-O-methyltransferase from Catharanthus roseus, and evidence that partially methylated
flavanones are substrates of four different flavonoid dioxygenases. Schroeder, Gudrun; Wehinger, Elke; Lukacin, Richard;
Wellmann, Frank; Seefelder, Wallburga; Schwab, Wilfried; Schroeder, Joachim. Institut fuer Biologie II, Universitaet Freiburg,
Freiburg, Germany. Phytochemistry (Elsevier) (2004), 65(8), 1085-1094. Publisher: Elsevier Science B.V., CODEN: PYTCAS
SciFinder (R))
Abstract
Catharanthus roseus (Madagascar periwinkle) flavonoids have a simple methylation pattern. Characteristic are B-ring 5' and 3'
methylations and a methylation in the position 7 of the A-ring. The first two can be explained by a previously identified unusual
O-methyltransferase (CrOMT2) that performs two sequential methylations. We used a homol. based RT-PCR strategy to search for
cDNAs encoding the enzyme for the A-ring 7 position. Full-length cDNAs for three proteins were characterized (CrOMT5, CrOMT6,
CrOMT7). The deduced polypeptides shared 59-66% identity among each other, with CrOMT2, and with CrOMT4 (a previously
characterized protein of unknown function). The five proteins formed a cluster sep. from all other OMTs in a relationship tree. Anal. of
the genes showed that all C. roseus OMTs had a single intron in a conserved position, and a survey of OMT genes in other plants
revealed that this intron was highly conserved in evolution. The three cDNAs were cloned for expression of His-tagged recombinant
proteins. CrOMT5 was insol., but CrOMT6 and CrOMT7 could be purified by affinity chromatog. CrOMT7 was inactive with all compds.
tested. The only substrates found for CrOMT6 were 3'-O-methyl-eriodictyol (homoeriodictyol) and the corresponding flavones and
flavonols. The mass spectrometric anal. showed that the enzyme was not the expected 7OMT, but a B-ring 4'OMT. OMTs with this
specificity had not been described before, and 3',4'-dimethylated flavonoids had not been found so far in C. roseus, but they are
well-known from other plants. The identification of this enzyme activity raised the question whether methylation could be a part of the
mechanisms channeling flavonoid biosynthesis. We investigated four purified recombinant 2-oxoglutarate-dependent flavonoid
dioxygenases: flavanone 3β-hydroxylase, flavone synthase, flavonol synthase, and anthocyanidin synthase. 3'-O-Methyl-eriodictyol
was a substrate for all four enzymes. The activities were only slightly lower than with the std.
substrate naringenin, and in some cases much higher than with eriodictyol. Methylation in the A-ring, however, strongly
reduced or abolished the activities with all four enzymes. The results suggested that B-ring 3' methylation is no hindrance
for flavonoid dioxygenases. These results characterized a new type of flavonoid O-methyltransferase, and also provided
new insights into the catalytic capacities of key dioxygenases in flavonoid biosynthesis.
Answer 790:
Exploring recombinant flavonoid biosynthesis in metabolically engineered Escherichia coli. Watts, Kevin T.; Lee, Pyung
Cheon; Schmidt-Dannert, Claudia. Department of Biochemistry, Molecular Biology and Biophysics, University of Minnesota, St.
Paul, MN, USA. ChemBioChem (2004), 5(4), 500-507. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: CBCHFX
(R))
Abstract
Flavonoids are important plant-specific secondary metabolites synthesized from 4-coumaroyl CoA, derived from the general
phenylpropanoid pathway, and three malonyl-CoAs. The synthesis involves a plant type III polyketide synthase, chalcone synthase.
We report the cloning and coexpression in Escherichia coli of phenylalanine ammonia lyase, cinnamate-4-hydroxylase,
4-coumarate:CoA ligase, and chalcone synthase from the model plant Arabidopsis thaliana. Simultaneous expression of all four genes
resulted in a blockage after the first enzymic step caused by the presence of nonfunctional cinnamate-4-hydroxylase. To overcome
this problem we fed exogenous 4-coumaric acid to induced cultures. We obsd. high-level prodn. of the flavanone naringenin as a
result. We were also able to produce phloretin by feeding cultures with 3-(4-hydroxyphenyl)propionic acid. Feeding with ferulic or
flavanone
caffeic acid did not yield the corresponding flavanones. We have also cloned and partially characterized a new tyrosine ammonia
lyase from Rhodobacter sphaeroides. Tyrosine ammonia lyase was substituted for phenylalanine ammonia lyase and
cinnamate-4-hydroxylase in our E. coli clones and three different growth media were tested. After 48 h induction, high-level prodn.
(20.8 mg L-1) of naringenin in metabolically engineered E. coli was obsd. for the first time.
Answer 791:
Hypolipidemic effects and absorption of citrus polymethoxylated flavones in hamsters with diet-induced
hypercholesterolemia. Kurowska, Elzbieta M.; Manthey, John A. KGK Synergize Inc., London, ON, Can. Journal of
Abstract
Formulations contg. citrus polymethoxylated flavones (PMF), mainly tangeretin, or citrus flavanone glucosides hesperidin and naringin
were evaluated for blood cholesterol-lowering potential in hamsters with diet-induced hypercholesterolemia. PMF metabolites were also
investigated. Diets contg. 1% PMF decreased blood serum total and very-low-d. lipoprotein (VLDL) + LDL cholesterol by 19-27 and
32-40%, resp., and decreased serum triacylglycerol levels. Comparable decreases were achieved by feeding 3% mixt. of hesperidin
and naringin (1:1), implying lower hypolipidemic potency of the hesperidin/naringin mixt. vs. PMF. HPLC-MS anal. identified high blood
serum, liver, and urine concns. of tangeretin metabolites, including dihydroxytrimethoxyflavone and
monohydroxytetramethoxyflavone glucuronides and aglycons. The total liver concns. of tangeretin derivs. corresponded to
hypolipidemic concns. of intact tangeretin in earlier expts. in vitro. PMF may be novel flavonoids with cholesterol- and
triacylglycerol-lowering potential. Elevated liver levels of PMF metabolites may be directly responsible for their hypolipidemic effects
in vivo.
Answer 792:
Quantitative analysis of the flavonoids in raw propolis from northern Croatia. Kosalec, Ivan; Bakmaz, Marina; Pepeljnjak,
Stjepan; Vladimir-Knezevic, Sanda. Institute of Microbiology Faculty of Pharmacy and Biochemistry, University of Zagreb, Zagreb,
Croatia. Acta Pharmaceutica (Zagreb, Croatia) (2004), 54(1), 65-72. Publisher: Croatian Pharmaceutical Society, CODEN:
ACPHEE ISSN: 1330-0075. Journal written in English. CAN 141:137026 AN 2004:302581 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Spectrometric analyses of flavonoids in twenty propolis samples, collected from ten different geog. localities in northern Croatia using
two complementary methods, are reported. Flavones and flavonols were detd. using aluminum chloride and expressed as quercetin
equiv. while flavanones were detd. using 2,4-dinitrophenylhydrazine and expressed as naringenin. Contents of flavones and flavonols
were similar for most samples and ranged from 2 to 2.3%, except for one sample with a concn. of 1.3% and one sample in which it was
not possible to detect flavones and flavonols. The content of flavanones in propolis samples is very variable. 55% Of samples
contained flavanones between 15 and 24% and 45% of samples between 4 and 14%. Total levels of flavonoids in raw propolis
samples ranged between 5 and 26%; for the majority of samples (75%), the total level of flavonoids ranged between 15 and 25.9%.
The high variability of flavanone concn. will affect the biol. activity of propolis prepns.
Answer 793:
flavanone
Trypanocidal flavonoids from Sophora flavescens. Matsuo, Kenji; Ito, Michiho; Honda, Gisho; Qui, Tran Kim; Kiuchi, Fumiyuki.
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto, Japan. Natural Medicines (Tokyo, Japan)
(2003), 57(6), 253-255. Publisher: Japanese Society of Pharmacognosy, CODEN: NMEDEO ISSN: 1340-3443. Journal written in
Abstract
The acetone ext. of Sophora flavescens (Leguminosae) exhibited lethal activity against Trypanosoma cruzi. Column chromatog. sepn.
of the ext. guided by trypanocidal activity afforded a new prenylated flavanone (4), together with nine known flavonoids:
sophoraflavanone G (1), (-)-kurarinone (2), kushenol L (3), 2'-methoxykurarinone (5),
7,4'-dihydroxy-5-methoxy-8-(γ,γ-dimethylallyl)-flavanone (6), leachianone A (7), 8-prenylnaringenin (8), noranhydroicaritin (9) and
alopecurone G (10). The structure of the new flavanone 4 was detd. on the basis of spectroscopic analyses. The min. lethal concns.
of these compds. against epimastigotes of T. cruzi were 3.7 μM (1), 14 μM (2), 7.1 μM (3), 7.2 μM (4), 6.9 μM (5), 71 μM (6), 5.5 μM
(7), 18 μM (8), 4.4 μM (9) and 3.6 μM (10).
Answer 794:
Multilocus analysis of variation and speciation in the closely related species Arabidopsis halleri and A. lyrata.
Ramos-Onsins, Sebastian E.; Stranger, Barbara E.; Mitchell-Olds, Thomas; Aguade, Montserrat. Departament de Genetica, Facultat
de Biologia, Universitat de Barcelona, Barcelona, Spain. Genetics (2004), 166(1), 373-388. Publisher: Genetics Society of
America, CODEN: GENTAE ISSN: 0016-6731. Journal written in English. CAN 141:20487 AN 2004:296073 CAPLUS
Abstract
Nucleotide variation in eight effectively unlinked genes was surveyed in species-wide samples of the closely related outbreeding
species Arabidopsis halleri and A. lyrata ssp. petraea and in three of these genes in A. lyrata ssp. lyrata and A. thaliana. Significant
genetic differentiation was obsd. more frequently in A. l. petraea than in A. halleri. Av. ests. of nucleotide variation were highest in A.
l. petraea and lowest in A. l. lyrata, reflecting differences among species in effective population size. The low level of variation in A. l.
lyrata is concordant with a bottleneck effect assocd. with its origin. The A. halleri/A. l. petraea speciation process was studied,
considering the orthologous sequences of an outgroup species (A. thaliana). The high no. of ancestral mutations relative to exclusive
polymorphisms detected in A. halleri and A. l. petraea, the significant results of the multilocus Fay and Wu H tests, and haplotype
sharing between the species indicate introgression subsequent to speciation. Av. among-population variation in A. halleri and A. l.
petraea was .apprx.1.5- and 3-fold higher than that in the inbreeder A. thaliana. The detected redn. of variation in A. thaliana is less
than that expected from differences in mating system alone, and therefore from selective processes related to differences in the
effective recombination rate, but could be explained by differences in population structure.
Answer 795:
Proteomic analysis on symbiotic differentiation of mitochondria in soybean nodules. Hoa, Le Thi-Phuong; Nomura, Mika;
Kajiwara, Hideyuki; Day, David Alexander; Tajima, Shigeyuki. Department of Life Science, Faculty of Agriculture, Kagawa
University, Kagawa, Japan. Plant and Cell Physiology (2004), 45(3), 300-308. Publisher: Japanese Society of Plant
Physiologists, CODEN: PCPHA5 ISSN: 0032-0781. Journal written in English. CAN 141:85768 AN 2004:284264 CAPLUS
flavanone
Abstract
Symbiotic interactions between legume plants and rhizobia induce specific metabs. and intracellular organelles in nodules. For
surveying symbiotic differentiation of a key organelle, mitochondria, protein constituents of soybean nodule and root mitochondria
were compared after two-dimensional electrophoresis, and the proteins were characterized in combination with matrix-assisted
desorption/ionization time-of-flight mass spectrometry, electrospray ionization mass spectrometry and N-terminal amino acid
sequencing. Of the proteins that were detected only in nodule mitochondria, phosphoserine aminotransferase, flavanone
3-hydroxylase, coproporphyrinogen III oxidase, one ribonucleoprotein and three unknown proteins were identified. Seven up-regulated,
eight down-regulated and two strongly suppressed protein spots in nodule mitochondria were also assigned protein identities. The
physiol. roles of these differential expressions were discussed in relation to nodule-specific metabs. in soybean nodules.
Answer 796:
Study of the extraction procedure by experimental design and validation of a LC method for determination of flavonoids in
Citrus bergamia juice. Calabro, M. L.; Galtieri, V.; Cutroneo, P.; Tommasini, S.; Ficarra, P.; Ficarra, R. Facolta di Farmacia,
Dipartimento Farmaco-Chimico, Universita di Messina, Messina, Italy. Journal of Pharmaceutical and Biomedical Analysis (2004),
35(2), 349-363. Publisher: Elsevier Science B.V., CODEN: JPBADA ISSN: 0731-7085. Journal written in English. CAN 141:70418
Abstract
A reversed-phase high-performance liq. chromatog. (HPLC) sepn. with photo-diode array detection was developed for the simultaneous
detn. of flavonoids extd. from Citrus bergamia juice. It employs a C18 reversed-phase column and a linear gradient elution system
with methanol/water with 5% acetic acid (vol./vol.), as mobile phase. The method was validated in terms of detection limits (LOD),
quantitation limits (LOQ), linearity, precision and accuracy. Limits of detection ranged from a low of 0.007 mg mL-1 (narirutin) to a high
of 0.018 mg mL-1 (didymin). The limits of quantitation were between a low of 0.011 mg mL-1 (7-OH flavanone) and a high of 0.024 mg
mL-1 (didymin). An excellent linear response was obsd. over the range specified for all analytes, as confirmed by the correlation
coeff. with ranged from 0.9982 and 0.9999. The intra-day R.S.D.% ranged from 0.11 to 3.64%. The intermediate precision R.S.D.%
were not higher than 7.62%. The accuracy of the method was confirmed with an av. recovery ranging, except for neoeriocitrin,
between 88.07% and 102.45%. Since the extn. conditions can affect analyte recovery, a suitable optimization strategy of the
procedure was needed. The exptl. parameters optimized were extn. time, temp., and solvents. A multivariate approach was used to
provide direct evaluation of the selected variables and related interactions. The D-optimal design was constructed by applying the
exchange algorithm. All exptl. results were computed by NEMROD-W software. This methodol. led us to obtain the best recovery for
all the flavonoids in the least no. of expts.
Answer 797:
Structural aspects of flavonoids as trypsin inhibitors. Maliar, Tibor; Jedinak, Andrej; Kadrabova, Jana; Sturdik, Ernest. VULM,
Modra, Slovakia. European Journal of Medicinal Chemistry (2004), 39(3), 241-248. Publisher: Elsevier Science Ltd., CODEN:
EJMCA5 ISSN: 0223-5234. Journal written in English. CAN 140:417263 AN 2004:271052 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
In the search for new proteinase inhibitors we have focused on the screening and Computer Assisted Drug Design (CADD) studies of
polyphenolic compds. In this paper we report CADD of flavonoles and flavones as trypsin inhibitors concomitant by the screening
flavanone
results. 5,7-Dihydroxy flavonoid have been found to be a perspective trypsin/trypsin-like-enzyme inhibitor. Flavanones and
isoflavones are less effective trypsin inhibitors due to a lost of the optimal geometry leading to hydrogen bond interactions. Four
different interaction modes were obsd., flavonoids are stabilized in S1 region of β-trypsin by formation of two (apigenin) or at least one
hydrogen bond and other significant electrostatic interactions. Quercetin, myricetin and morin have shown to be the best trypsin
inhibitors tested. In general, flavonoids with suitably located hydroxy groups and planar conformation are the building blocks able to
replace guanidinobenzoyl part of successful inhibitors. Physiol. nature of flavonoids reveals biotechnol. source of new trypsin
inhibitors as antipancreatitis, anticancer and anti-inflammation drugs.
Answer 798:
Toxicity and Cell Cycle Effects of Synthetic 8-Prenylnaringenin and Derivatives in Human Cells. Tokalov, Sergey V.;
Henker, Yvonne; Schwab, Pia; Metz, Peter; Gutzeit, Herwig O. Institut fuer Zoologie, TU Dresden, Dresden, Germany.
Pharmacology (2004), 71(1), 46-56. Publisher: S. Karger AG, CODEN: PHMGBN ISSN: 0031-7012. Journal written in English.
Abstract
The estrogenic flavanone rac-8-prenylnaringenin (8-PN) and 3 derivs. (rac-7-(O-prenyl)naringenin-4'-acetate (7-O-PN),

rac-5-(O-prenyl)naringenin-4',7-diacetate (5-O-PN), and rac-6-(1,1-dimethylallyl)naringenin (6-DMAN) were prepd. by chem. synthesis
and analyzed with respect to their toxicity and possible cell cycle effects in human acute myeloid leukemia (HL-60) cells. With the
exception of 5-O-PN, all the other naringenins showed only weak toxic effects at concns. below 50 μmol/l. A cell cycle anal. over
several cell generations up to 4 days was carried out using the fluorescent dye carboxyfluorescein diacetate N-succinimidyl ester
(CFSE) followed by propidium iodide (PI) staining at the end of the expt. The well-studied flavonol quercetin was included in the anal.
as a ref. substance. All flavonoids affected cell proliferation, but the extent and the resulting changes in the proliferation pattern were
specific for each substance. In contrast to the radical scavenging activity of quercetin, the tested flavanones showed no
anti-oxidative properties using several different test systems. Similarly, the mitochondrial membrane potential (ΔΨm) was hardly
effected by these compds., while both menadione and quercetin strongly reduced the potential after 1 h of treatment. The reported
chem. modification of interesting lead substances (like the strongly estrogenic 8-PN) presents a promising approach to modulate the
properties of a relevant substance in a pharmacol. desirable way. The low toxicity and weak cytostatic properties of the tested
naringenin derivs. is encouraging for further studies on known naringenin target mols.
Answer 799:
Synthesis of new halogenated flavonoids by reaction with hydrogen halides in the presence of dimethyldioxirane. Arnone,
Alberto; Nasini, Gianluca; Panzeri, Walter; Vajna de Pava, Orso; Zucca, Cristina. Politecnico di Milano, Dipartimento di Chimica,
Materiali ed Ingegneria Chimica "Giulio Natta", C.N.R. Istituto di Chimica del Riconoscimento Molecolare Sezione A. Quilico, Milan,
Italy. Journal of Chemical Research, Synopses (2003), (11), 683-684, M1141-M1150. Publisher: Science Reviews, CODEN:
JRPSDC ISSN: 0308-2342. Journal written in English. CAN 141:173989 AN 2004:265780 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
This paper presents the synthesis and characterization of new halogenated ether derivs. of flavans, flavanols and flavanones,
obtained by reaction of the corresponding Me ethers with hydrogen halides in the presence of dimethyldioxirane as an oxidative agent.
Answer 800:
flavanone
New metabolic pathways for flavanones catalyzed by rat liver microsomes. Nikolic, Dejan; Van Breemen, Richard B.
Department of Medicinal Chemistry and Pharmacognosy, UIC/National Institutes of Health Center for Botanical Dietary Supplements
Research, College of Pharmacy, University of Illinois at Chicago, Chicago, IL, USA. Drug Metabolism and Disposition (2004),
32(4), 387-397. Publisher: American Society for Pharmacology and Experimental Therapeutics, CODEN: DMDSAI ISSN: 0090-9556.
Abstract
Flavonoids represent a diverse group of natural pigments widely distributed in the plant kingdom and are an important component of
human diet due to their high content in fruits and vegetables. Since many flavonoids have been shown to be potent inhibitors,
substrates, and even inducers of various cytochrome P 450 isoforms, there is considerable interest in studying interactions of this
class of mols. with the cytochrome P 450 enzyme system. In this study, the metab. of several simple flavanones by rat liver
microsomes was investigated and compared. In addn. to the expected arom. hydroxylation products, several novel metabolic
pathways were obsd. including C-ring desatn. to form the corresponding flavones, oxidn. of the B-ring to generate an unusual quinol
oxidn. product, B-ring cleavage with the formation of chromone derivs., and redn. of carbonyl group to form flavan-4-ol derivs. The
metabolites were characterized and identified primarily by using liq. chromatog.-tandem mass spectrometry with comparison to
authentic stds. Formation of flavones from dietary flavanones might have biol. significance since flavones often exhibit pharmacol.
activities that are different from those of flavanones. However, little is known about the pharmacol. activities of the other types of
flavanone metabolites.
Answer 801:
Growth inhibition of cancer by flavonoid. Yoshida, Tatsushi; Sakai, Toshiyuki. Department of Molecular-Targeting Cancer
Prevention, Graduate School of Medical Science, Kyoto Prefectural University of Medicine, Kyoto, Japan. Ketsueki, Shuyoka
(2003), 47(6), 571-574. Publisher: Kagaku Hyoronsha, CODEN: KETSBI ISSN: 0915-8529. Journal; General Review written in
Japanese. CAN 141:16670 AN 2004:256603 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
A review. Antitumor effects of flavonoid by the inhibition of cancer cell proliferation is reviewed including the classification of
flavonoid such as flavan, flavone, flavonol, flavanol, isoflavone, flavanone, chalkone, and anthocyanidin, as well as its antitumor
mechanism through genetic regulation and p53-RB pathway with examples.
Answer 802:
Biosynthetic production of flavonoid and isoflavonoid nutraceuticals by genetic manipulation of enzymes in plants.
Dixon, Richard A.; Liu, Chang-jun; Deavours, Bettina. (The Samuel Roberts Noble Foundation, Inc., USA). PCT Int. Appl. (2004),
80 pp. CODEN: PIXXD2 WO 2004024079 A2 20040325 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY,
KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC,
SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH,
CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent
flavanone

WO 2004024079 A2 20040325 WO 2003-US28454 20030910
WO 2004024079 A3 20050519
W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM,
DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC,
LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU,
SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW
RW: GH, GM, KE, LS, MW, MZ, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM, AT, BE,
BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IT, LU, MC, NL, PT, RO, SE, SI, SK, TR,
BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG
AU 2003270537 A1 20040430 AU 2003-270537 20030910
AU 2003270537 B2 20080320
US 20040128711 A1 20040701 US 2003-659755 20030910
EP 1555870 A2 20050727 EP 2003-752235 20030910
NZ 538259 A 20080328 NZ 2003-538259 20030910
US 2002-409447P P 20020910
WO 2003-US28454 W 20030910
Abstract
The invention provides method and compns. for the modulation of flavanone and/or isoflavone prodn. in plants. Transgenic plants
having novel phenotypes are generated by down-regulating flavanone 3-hydroxylase by loss-of-function mutations or antisense
oligonucleotides, and up-regulation of isoflavone synthase, chalcone isomerase, and/or chalcone synthase by cloning their genes into
the recipient plants. Introduction of isoflavone synthase into plants in which the flavanone 3-hydroxylase is down-regulated results in
significant improvement to the levels of accumulation of the isoflavone genistein; this can be coupled with increasing flux into the
prodn. of naringenin to result in even further enhancement of isoflavone prodn. Increased expression of isoflavones in particular in
plants may be used to increase the nutritional value of food plants for both human and animal consumption. The invention overcomes
limitations of the prior art which prevented accumulation of high levels of isoflavones in plants.
Answer 803:
Anti-inflammatory activities of two flavanones, sigmoidin A and sigmoidin B, from Erythrina sigmoidea. Njamen,
Dieudonne; Mbafor, Joseph Tanyi; Fomum, Zacharias Tanee; Kamanyi, Albert; Mbanya, Jean-Claude; Recio, M. Carmen; Giner, Rosa
M.; Manez, Salvador; Rios, Jose Luis. Laboratory of Animal Physiology, Department of Animal Biology and Physiology, Faculty of
Science, University of Yaounde 1, Yaounde, Cameroon. Planta Medica (2004), 70(2), 104-107. Publisher: Georg Thieme Verlag,
flavanone
Abstract
Two prenylated flavanones isolated from Erythrina sigmoidea Hua (sigmoidin A and sigmoidin B) were studied for their ability to inhibit
the stable 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical and arachidonic acid metab. In addn., the compds. were studied in two
exptl. models of inflammation induced in mouse ears by 12-O-tetradecanoylphorbol 13-acetate (TPA) and the phospholipase A2-induced
mouse paw edema. Both sigmoidins A and B proved to be potent scavengers of the DPPH radical, while the study of the inhibition of
arachidonic acid metab. demonstrated that these same compds. were selective inhibitors of 5-lipoxygenase, with no effect on
cyclooxygenase-1 activity. Dose-response inhibitor potency was established for sigmoidin A (IC50 = 31 μM). In the assay of
phospholipase A2-induced mouse paw edema, only the sigmoidin B deriv. inhibited edema formation at 60 min, showing a percentage
of inhibition below that obtained with cyproheptadine (59% vs. 74%). In the TPA test, sigmoidins A and B decreased the induced
edema by 89% and 83%, resp. This is the first time that the anti-inflammatory activity and antioxidant properties of these
prenylflavanones have been reported. The results indicate that the compds. have different mechanisms of action depending on
whether one or two prenyl groups are present in ring B.
Answer 804:
Selective Cytotoxicity of a Red Grape Wine Flavonoid Fraction Against MCF-7 Cells. Hakimuddin, Fatima; Paliyath,
Gopinadhan; Meckling, Kelly. Department of Food Science, University of Guelph, Guelph, ON, Can. Breast Cancer Research
and Treatment (2004), 85(1), 65-79. Publisher: Kluwer Academic Publishers, CODEN: BCTRD6 ISSN: 0167-6806. Journal written
Abstract
Red wine is a rich source of polyphenolic components such as anthocyanins and flavonoids. The inhibitory effects of red wine
polyphenolics on human breast cancer cells have been demonstrated earlier, but their effects on normal cells have not been fully
established. Red wine (Merlot) was fractionated by hydrophobic interaction chromatog. and different flavonoid fractions with increasing
hydrophobicity were obtained. These fractions were tested for their inhibitory effect on human breast cancer cells (MCF-7), normal
human mammary epithelial cells (HMEC), and a non-tumorigenic MCF-10A cell line. By contrast to the authentic flavonoids such as
quercetin, naringenin and catechin which inhibited the growth of HMEC much more than that of MCF-7 cancer cells, a red wine fraction,
that was comprised mainly of the flavonoid aglycons, showed maximal inhibition of the growth of breast cancer cells, with relatively
low cytotoxicity towards HMEC and MCF-10A cells. In the presence of this flavonoid fraction, the normal cells grew normally, whereas
the breast cancer cells underwent a change in morphol. into spherical forms. Cytotoxicity analyses suggested that these cells had
become apoptotic. The efficiency of inhibition of cell proliferation by various flavonoid fractions appeared to be related to their
inhibition of calcium and calmodulin-promoted phosphodiesterase activity, suggesting that flavonoids may interfere with calcium
second messenger function. The results suggest that certain grape wine ingredients have anticancer properties and these ingredients
may be helpful for developing designer functional foods with cancer-preventive properties.
Answer 805:
Naringenin from Citrus junos Has an Inhibitory Effect on Acetylcholinesterase and a Mitigating Effect on Amnesia. Heo, Ho
Jin; Kim, Mi-Jeong; Lee, Jung-Min; Choi, Soo Jung; Cho, Hong-Yon; Hong, Bumshik; Kim, Hye-Kyung; Kim, Eunki; Shin, Dong-Hoon.
Graduate School of Biotechnology, Korea University, Seoul, S. Korea. Dementia and Geriatric Cognitive Disorders (2004), 17(3),
151-157. Publisher: S. Karger AG, CODEN: DGCDFX ISSN: 1420-8008. Journal written in English. CAN 141:236293 AN
Abstract
flavanone
This study was performed to identify safe and more effective acetylcholinesterase (AChE) inhibitors in the treatment of Alzheimer's
disease. The total methanol ext. of Citrus junos had a significant inhibitory effect on AChE in vitro. By sequential fractionation of C.
junos, the active component was finally identified as naringenin. Naringenin inhibited AChE activity in a dose-dependent manner. In
this study, we also evaluated the anti-amnesic activity of naringenin, a major flavanone constituent isolated from C. junos, in vivo
using ICR mice with amnesia induced by scopolamine (1 mg/kg body wt.). Naringenin, when administered to mice at 4.5 mg/kg body
wt., significantly ameliorated scopolamine-induced amnesia as measured in both the passive avoidance and the Y-maze test. These
results suggest that naringenin may be a useful chemopreventive agent against Alzheimer's disease.
Answer 806:
Transition state stabilization by general acid catalysis, water expulsion, and enzyme reorganization in Medicago savita
chalcone isomerase. Hur, Sun; Newby, Zachary E. R.; Bruice, Thomas C. Department of Chemistry and Biochemistry,
University of California, Santa Barbara, CA, USA. Proceedings of the National Academy of Sciences of the United States of
America (2004), 101(9), 2730-2735. Publisher: National Academy of Sciences, CODEN: PNASA6 ISSN: 0027-8424. Journal
Abstract
In aq. soln., Medicago sativa chalcone isomerase (CHI) enhances the reaction rate for the unimol. rearrangement of chalcone (CHN)
into flavanone by seven orders of magnitude. Conformations of CHN and their relative free energies in water and CHI were
investigated by the thermodn. perturbation method. In water, CHN adopts two conformations (I and II) with conformation I being higher
in energy than conformation II by 3 kcal/mol. Only I can give rise to a near attack conformer (NAC) where the nucleophile O2' and the
electrophile C9 are placed in proximity. In CHI, I binds less tightly than II by ≈ 2 kcal/mol, resulting in the free energy for NAC
formation being ≈ 2 kcal/mol higher in the enzyme than in water. This unfavorable feature in the ground state of the CHI reaction
requires the predominant catalytic advantage to be taken in the step of NAC → transition state (TS). From the mol. dynamics
simulations of apo-CHI, CHI complexed with CHN (CHI⋅CHN) and CHI⋅TS, the authors found: (i) Lys-97-general-acid catalysis of the
O2'- nucleophilic addn.; (ii) expulsion of three water mols. in the process of TS formation; (iii) release of enzyme structural distortion on
TS formation. In the conclusion, CHI's remarkable efficiency of stabilizing the TS and its relatively poor ability in organizing the ground
state is compared with chorismate mutase whose catalytic prowess, when compared with water, originates predominantly from the
enhanced NAC population at the active site.
Answer 807:
Hydroxylation at C4' or C6 is essential for apoptosis-inducing activity of flavanone through activation of the caspase-3
cascade and production of reactive oxygen species. Ko, Ching Huai; Shen, Shing-Chuan; Chen, Yen Chou. School of
Pharmacy, Graduate Institute of Pharmaceutical Sciences, Taipei Medical University, Taipei, Taiwan. Free Radical Biology &
Medicine (2004), 36(7), 897-910. Publisher: Elsevier, CODEN: FRBMEH ISSN: 0891-5849. Journal written in English. CAN
Abstract
Previous studies demonstrated that hydroxyl groups play important roles in the antioxidative activities of flavonoids; however, the
importance of structurally related hydroxylation in their apoptosis-inducing activities is still undefined. In the present study, flavanone
with hydroxylation at C4' and C6 had a significant cytotoxic effect in human leukemia HL-60 cells accompanied by the occurrence of
DNA ladders, apoptotic bodies, and hypodiploid cells, characteristics of apoptosis. The replacement of a hydroxyl group (OH) by a
methoxyl (OCH3) group at C4' or C6 attenuated the apoptotic effect in cells, and there was no significant cytotoxicity of flavanone or
flavanone with OH or OCH3 in C7-treated HL-60 cells. Induction of enzyme activity of caspase-3 and -9, but not caspase-1 and -8,
flavanone
accompanied by release of cytochrome C from mitochondria to cytosol and the appearance of cleaved of PARP (85 kDa), D4-GDI (23
kDa), and caspase-3 (p17/p15) fragments, was identified in 4'-OH- or 6-OH- flavanone-treated HL-60 cells. Caspase-3 and -9 inhibitors
Ac-DEVD-FMK and Ac-LEHD-FMK, but not caspase-1 and -8 inhibitors Ac-YVAD-FMK and Ac-LETD-FMK, attenuated 4'-OH- or
6-OH-flavanone-induced cell death. And, inhibition of caspase-9 activity by Ac-LEHD-FMK suppresses caspase-3 protein procession
induced by 4'-OH- and 6-OH-flavanone, indicative of caspase-9 activation locating upstream of caspase-3. A decrease in the
antiapoptotic protein Mcl-1 and increases in the pro-apoptotic proteins Bax and Bad were found in 4'-OH- or 6-OH-flavanone-treated
HL-60 cells. Induction of endogenous ROS prodn. was detected in 4'-OH- or 6-OH-flavanone-treated HL-60 cells by the DCHF-DA
assay. Antioxidants such as N-acetylcysteine (NAC), catalase (CAT), superoxide dismutase (SOD), and allopurinol (ALL), but not
pyrrolidine dithiocarbamate (PDTC) or diphenylene iodonium (DPI), significantly inhibited 4'-OH- or 6-OH-flavanone-induced ROS
prodn., with blocking of the apoptosis induced by 4'-OH- or 6-OH-flavanone.
The apoptosis-inducing activity of 4'-OH- or 6-OH-flavanone was also obsd. in another leukemia cell line (Jurkat), but was
not found in mature monocytic cells (THP-1) and normal human polymorphonuclear neutrophils (PMNs). This suggests
that hydroxylation at C4' or C6 is important to the apoptosis-inducing activities of flavanone through ROS prodn., and
that activation of the caspase-3 cascade, downstream of caspase-9 activation, is involved.
Answer 808:
Type-2 helper T cell-derived cytokine inhibitors containing defined natural components. Kishida, Kotaro; Uno, Katsuko;
Tanaka, Hiroshi; Kitatani, Noritake. (Narisu Cosmetic Co., Ltd., Japan). Jpn. Kokai Tokkyo Koho (2004), 12 pp. CODEN:
JKXXAF JP 2004075619 A 20040311 Patent written in Japanese. Application: JP 2002-239293 20020820. Priority: . CAN

JP 2004075619 A 20040311 JP 2002-239293 20020820
JP 2002-239293 20020820
Abstract
The invention relates to an inhibitor of type-2 helper T cell (Th2)-derived cytokine, suitable for use in a cosmetic or food to prevent
hyperactive Th2-related symptoms, e.g. allergic inflammation and atopic symptoms, etc., wherein the inhibitor contains catechin
deriv., flavonol deriv., flavanone deriv. coumarin deriv. Vitis seed ext., Fuscoporia ext., and/or Malus peel ext. The effect of
Fuscoporia obliqua ext. on IL-4, INF-γ, and Th1/Th2 in peripheral blood mononuclear cells (PBMC) cells was examd. A cosmetic cream
contg. Fuscoporia obliqua ext. 3 % was formulated, and applied to patients with atopic dermatitis.
Answer 809:
Significance of C-terminal sequence elements for Petunia flavanone 3β-hydroxylase activity. Wellmann, Frank; Matern,
Ulrich; Lukacin, Richard. Institut fur Pharmazeutische Biologie, Philipps-Universitat Marburg, Marburg, Germany. FEBS Letters
(2004), 561(1-3), 149-154. Publisher: Elsevier Science B.V., CODEN: FEBLAL ISSN: 0014-5793. Journal written in English. CAN
flavanone
Abstract
Flavanone 3β-hydroxylase (FHT), a 2-oxoglutarate-dependent dioxygenase (2-ODD), catalyzes the hydroxylation of (2S)-flavanones to
(2R/3R)-dihydroflavonols in plants as a key step towards the biosynthesis of flavonols, anthocyanins and catechins. Crystallog.
studies of 2-ODDs typically revealed a jelly roll in the enzyme core, and the C-terminus of the enzyme polypeptides was proposed to
form a lid covering the active site cavity, thereby reducing the chances for oxidative or proteolytic damage and unfolding. Moreover,
it has been proposed that in some cases the C-terminus is involved in substrate selectivity of 2-ODDs. In a systematic approach with
highly active Petunia FHT, four C-terminally truncated enzyme forms were generated by deletion of five, 11, 24 or 29 amino acids.
The recombinant FHTs preserved their substrate selectivity, but the specific activity decreased gradually with the extent of truncation.
An enzyme chimera was subsequently constructed by a domain swapping approach, thereby replacing the C-terminal 52 amino acids
of Petunia FHT with the equiv. region of flavonol synthase (FLS) from Citrus unshiu, an enzyme that shows ambiguous FLS and FHT
activity. The chimeric dioxygenase still revealed exclusively FHT activity, albeit at a moderate level. The data predict that the
selectivity of FHT is not governed by the C-terminal sequence that accounts for about 13% of the enzyme polypeptide chain.
Answer 810:
Advances in study on chemical constituents in Hypericum Linn. Lu, Hongfei; Chu, Qinggang; Hu, Zhenghai. College of Life
and Environment Science, Zhejiang Normal University, Jinhua, Peop. Rep. China. Zhongcaoyao (2002), 33(12), 1135-1138.
Publisher: Zhongcaoyao Zazhi Bianjibu, CODEN: CTYAD8 ISSN: 0253-2670. Journal; General Review written in Chinese. CAN
Abstract
A review with 44 refs. on advances in study on chem. constituents in Hypericum Linn. with subdivision headings: (1) dianthranone
derivs.; (2) flavanone alcs.; (3) flavones and flavone alcs.; (4) xanthones; (5) coumarins; (6) phenolic acids; phloroglucinols; (8)
volatile oils; and (9) others.
Answer 811:
A flavanone and two phenolic acids from Chrysanthemum morifolium with phytotoxic and insect growth regulating activity.
Beninger, Clifford W.; Abou-Zaid, Mamdouh M.; Kistner, Adrienne L. E.; Hallett, Rebecca H.; Iqbal, Muhammad J.; Grodzinski, Bernard;
Hall, J. Christopher. Department of Environmental Biology, University of Guelph, Guelph, ON, Can. Journal of Chemical
Ecology (2004), 30(3), 589-606. Publisher: Kluwer Academic/Plenum Publishers, CODEN: JCECD8 ISSN: 0098-0331. Journal
Abstract
Leaves of Chrysanthemum morifolium cv. Ramat were extd. sequentially with hexane, Et acetate, and methanol. The methanol
fraction, when incorporated into artificial diet, was found to reduce the growth of cabbage looper (Trichoplusia ni Hubner) larvae at
concns. between 500 and 5000 ppm of diet. Fractionation of the methanol ext. on a Sephadex column yielded five fractions, three of
which reduced the wt. of larvae relative to the control. One fraction was analyzed using HPLC and found to contain three main
constituents. These compds. were purified using a combination of gel permeation chromatog. on Sephadex LH20 and HPLC, and
analyzed by 1H and 13C NMR as well as undergoing chem. and phys. analyses. The compds. were identified as chlorogenic acid,
3,5-O-dicaffeoylquinic acid. and 3',4',5-trihydroxyflavanone 7-O-glucuronide. At concns. between 100 to 1000 ppm, these compds.
reduced both growth and photosynthesis of Lemna gibba L. with the order of efficacy being flavanone > chlorogenic acid >
3,5-O-dicaffeoylquinic acid. Furthermore, when incorporated sep. into an artificial diet, these compds., at 10 to 1000 ppm, enhanced or
flavanone
reduced growth of the cabbage looper (Trichoplusia ni) and gypsy moth (Lymantria dispar L.).
Answer 812:
Changes in the Levels of Polymethoxyflavones and Flavanones as Part of the Defense Mechanism of Citrus sinensis (Cv.
Valencia Late) Fruits against Phytophthora citrophthora. Del Rio, J. A.; Gomez, P.; Baidez, A. G.; Arcas, M. C.; Botia, J. M.;
Ortuno, A. Plant Biology Department Faculty of Biology, University of Murcia, Espinardo, Spain. Journal of Agricultural and
Food Chemistry (2004), 52(7), 1913-1917. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal
Abstract
Phytophthora citrophthora causes serious losses in Citrus fruits through brown rot lesion. The effect of infection with P. citrophthora
on Citrus sinensis (cv. Valencia Late) fruits was studied, with particular ref. to the levels of the flavanones hesperidin and isonaringin
and the polymethoxyflavones sinensetin, nobiletin, tangeretin, and heptamethoxyflavone, because flavonoids are most probably
involved as natural defense or resistance mechanisms in this genus. Changes in the levels of these flavonoids were detected after
infection. The hesperidin and isonaringin contents fell by 13 and 67%, resp., whereas the contents of their corresponding aglycons,
hesperetin and naringenin, increased, suggesting the hydrolyzing effect of this fungus on the glycosylated flavanones. The
heptamethoxyflavone, nobiletin, sinensetin, and tangeretin levels increased by 48, 28, 26, and 24%, resp. The in vitro study revealed
that these compds. acted as antifungal agents, the most active being the aglycons (naringenin and hesperetin), followed by the
polymethoxyflavones and flavanone glycosides. The participation of these flavonoids in the defense mechanism of this Citrus
species is discussed.
Answer 813:
Studies on flavonoids from Sophora flavescens ait using ESI-MS. Bai, Yu; Guo, Ming-Quan; Song, Feng-Rui; Liu, Zhi-Qiang;
Liu, Shu-Ying. Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, Peop. Rep. China.
Gaodeng Xuexiao Huaxue Xuebao (2004), 25(2), 284-288. Publisher: Gaodeng Jiaoyu Chubanshe, CODEN: KTHPDM ISSN:
Abstract
Two kinds of flavonoids from Sophora flavescens Aits, dihydroflavonoids and dihydroflavonols, were studied by using electrospray
ionization tandem mass spectrometry(ESI-MSn). [M-H]- of these two kinds of flavonoids were obsd. in the neg. ion mode under ESI
conditions, which provided us the mol. wts. of them. Cross-ring reactions, arisen from MS2 spectra of both dihydroflavonoids and
dihydroflavonols, gave the fragment ions by the loss of neutral species. The differences of their cleavage positions were then
proposed, dihydroflavonoids cleave at C2-O bond and C4-C10 bond, but dihydroflavonols cleave at C2-O bond and C3-C4 bond. The
loss of neutral species from dihydroflavonoids and dihydroflavonols were also discussed, the former were several relative big neutral
species, while the latter were some small species, such as CO, CO2, H2O and B-ring. The differences between dihydroflavonoids and
dihydroflavonols were mainly arisen by hydroxy group at C-3 of the C-ring, which were the characteristic for dihydroflavonoids and
dihydroflavonols under the ESI-MSn conditions.
Answer 814:
flavanone
Activation of flavonoid biosynthesis by solar radiation in bilberry (Vaccinium myrtillus L.) leaves. Jaakola, Laura;
Maeaettae-Riihinen, Kaisu; Kaerenlampi, Sirpa; Hohtola, Anja. Department of Biology/Botany, University of Oulu, Oulu, Finland.
Planta (2004), 218(5), 721-728. Publisher: Springer-Verlag, CODEN: PLANAB ISSN: 0032-0935. Journal written in English. CAN
Abstract
The effect of solar radiation on flavonoid biosynthesis was studied in bilberry (Vaccinium myrtillus L.) leaves. Expression of flavonoid
pathway genes of bilberry was studied in the upper leaves of bilberry, exposed to direct sunlight, in the shaded leaves growing lower in
the same plants and in fruits. Bilberry-specific digoxigenin-dUTP-labeled cDNA fragments of five genes from the general
phenylpropanoid pathway coding phenylalanine ammonia-lyase and from the flavonoid pathway coding chalcone synthase, flavanone
3-hydroxylase, dihydroflavonol 4-reductase, and anthocyanidin synthase were used as probes in gene expression anal. Anthocyanins,
catechins, proanthocyanidins, flavonols and hydroxycinnamic acids from the leaves and fruits were identified and quantified using
high-performance liq. chromatog. combined with a diode array detector. An increase in the expression of the studied flavonoid
pathway genes was obsd. in leaves growing under direct sun exposure. Also, the concns. of anthocyanins, catechins, flavonols and
hydroxycinnamic acids were higher in the leaves exposed to direct sunlight. However, the concn. of polymeric procyanidins was lower
in sun-exposed leaves, whereas that of prodelphinidins was slightly increased. The results give further support for the protective role
of flavonoids and hydroxy cinnamic acids against high solar radiation in plants. Also, the roles of different flavonoid compds. as a
defense against stress caused by sun exposure is discussed.
Answer 815:
Determination of flavonoids by high-performance liquid chromatography and capillary electrophoresis. Wang, Shu-Ping;
Huang, Kuo-Jun. Department of Applied Chemistry, Providence University, Hsien, Taiwan. Journal of Chromatography, A
(2004), 1032(1-2), 273-279. Publisher: Elsevier Science B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English.
Abstract
The compds. of flavonoid, an important group in nature, can prevent coronary heart disease and anticancer by virtue of the
characteristics of antioxidn. Nine flavonoids most often seen in grape wine, namely apigenin, baicalein, naringenin, luteolin,
hesperetin, galangin, kaempferol, quercetin, and myricetin, were detd. HPLC and CZE. A successful resoln. was obtained from an
unusual additive of THF in mobile phase by HPLC. One notable thing is that the mixt. of luteolin and quercetin could be sepd. for the
first time by HPLC. In addn., the better detection limit was still attainable even with the use of THF. The detection limits of CZE
performed in borate buffer were hundreds-fold better than in previous reports. Furthermore, the retention and migration behavior of the
analytes studied were discussed. As the result of this study, the elution order of flavone and flavanone was reversed to the
contention proposed by Wulf et al. It was predictable from the interaction with THF. Consequently, the exts. from grape wine with
solid-phase extn. were analyzed by developing methods of HPLC and CZE. The obtained recoveries ranged from 90 to 107% and the
relative std. deviations were under 6.3%.
Answer 816:
Xanthohumol metabolites in feces of rats. Nookandeh, Aslieh; Frank, Norbert; Steiner, Frank; Ellinger, Renate; Schneider, Bernd;
Gerhauser, Clarissa; Becker, Hans. Institute for Pharmacognosy and Analytical Phytochemistry, University of the Saarland,
Saarbrucken, Germany. Phytochemistry (Elsevier) (2004), 65(5), 561-570. Publisher: Elsevier Science B.V., CODEN: PYTCAS
SciFinder (R))
flavanone
Abstract
Xanthohumol (1), isolated from hop, was fed to rats in a dose of 1000 mg kg-1 body wt. The feces of the animals were collected after
24 and 48 h and analyzed for metabolites of 1. Approx. 89% of the recovered flavonoid-compds. consisted of unchanged 1. Sixteen
metabolites and six previously known metabolites were isolated and characterized by coupling techniques (HPLC-NMR, HPLC-MS and
HPLC-DAD). Their structures were elucidated by spectroscopic methods, esp. using NMR spectroscopy. Twenty metabolites had a
modified chalcone structure and two metabolites were flavanone derivs.
Answer 817:
EST analysis of genes involved in secondary metabolism in Camellia sinensis (tea), using suppression subtractive
hybridization. Park, Jong-Sug; Kim, Jung-Bong; Hahn, Bum-Soo; Kim, Kyung-Hwan; Ha, Sun-Hwa; Kim, Jong-Bum; Kim,
Yong-Hwan. RDA, Metabolic Engineering Division, National Institute of Agricultural Biotechnology, Suwon, S. Korea. Plant
Science (Amsterdam, Netherlands) (2004), 166(4), 953-961. Publisher: Elsevier, CODEN: PLSCE4 ISSN: 0168-9452. Journal
Abstract
Camellia sinensis (tea) is a com. important crop that is valued for its secondary metabolites. Higher levels of catechins are
accumulated in young leaves than in mature leaves. To understand the mol. regulation of secondary metab. in tea leaves,
differentially expressed genes of interest should be identified, cloned, and studied in detail. A total of 588 cDNA clones from a
subtractive cDNA library were randomly picked, sequenced, and analyzed. High-quality sequences were isolated for 508 of these
clones. BlastX comparisons indicated that about 8.7% of the clones encoded enzymes involved in secondary metab., with a
particularly high abundance of flavonoid-metab. proteins (5.1%). These ESTs facilitated the isolation and characterization of genes
involved in the flavonoid pathway in tea: chalcone synthase (CHS), flavanone 3-hydroxylase (F3H), flavonoid 3',5'-hydroxylase
(F3'5'H), flavonol synthase (FLS), dihydroflavonol 4-reductase (DFR), and leucoanthocyanidin reductase (LCR). The three genes
encoding F3H, DFR, and LCR were more highly expressed in young leaves than in mature leaves. These results indicate that
flavonoid biosynthesis genes from tea are differentially regulated in the developmental stages. The subtractive cDNA library and EST
database described in this study represent a valuable resource for future research aimed at improving economically important
secondary metabolic characteristics in crops.
Answer 818:
Flavonoid biosynthesis in bilberry (Vaccinium myrtillus L.). Jaakola, L.; Hohtola, A.; Maatta, K.; Torronen, R.; Karenlampi, S.
Department of Biology/Botany, University of Oulu, Oulu, Finland. Acta Horticulturae (2003), 618 415-419. Publisher:
International Society for Horticultural Science, CODEN: AHORA2 ISSN: 0567-7572. Journal written in English. CAN 141:36206
Abstract
Bilberry (Vaccinium myrtillus L.) is the characteristic understory species in boreal forests. In Northern Europe it is among the most
important wild berries. Bilberry is preferably a shade plant and when growing under direct sunlight, the upper leaves of the plants turn
red. This phenomenon is regarded to provide protection against UV-B irradn. via the prodn. of anthocyanins and other protective
flavonoids. The aim of the present study was to clarify the role of flavonoid biosynthesis of the bilberry plants growing in the direct
sunlight. Expression of flavonoid pathway genes of bilberries was studied in the upper leaves of bilberry, exposed to direct sunlight, in
the shade leaves growing lower in the same plants and in berries. Bilberry-specific digoxigenin-dUTP labeled cDNA fragments of five
flavanone
genes from the flavonoid pathway, phenylalanine ammonia-lyase (PAL), chalcone synthase (CHS), flavanone 3-hydroxylase (F3H),
dihydroflavonol 4-reductase (DFR), and anthocyanidin synthase (ANS), were used as probes for detg. the expression of the flavonoid
pathway genes in bilberries. The results indicate the activation of the expression of flavonoid pathway genes in bilberry leaves
exposed to the direct sunlight.
Answer 819:
Ionizing radiation and storage effects on postharvest quality of Rio Red grapefruit. Vanamala, J. K. P.; Cobb, B. G.; Pike, L.
M.; Patil, B. S. Department of Horticultural Sciences, Texas A+M University, College Station, TX, USA. Acta Horticulturae
(2003), 628(Vol. 2, Issues and Advances in Postharvest Horticulture, Volume 2), 635-641. Publisher: International Society for
Horticultural Science, CODEN: AHORA2 ISSN: 0567-7572. Journal written in English. CAN 140:405856 AN 2004:165381
Abstract
Irradn. is rapidly becoming the preferred method of quarantine treatment against fruit flies for citrus fruit and improving shelf life of
the fruit during storage. Citrus fruit contain several biol. active functional components that are known to prevent chronic diseases
such as cancer and cardiovascular diseases. The preventative activity has been assocd. with polyphenol content in citrus fruit.
RioRed grapefruit (Citrus paradisi) were harvested in the middle of Mar., 2001 and exposed to gamma irradn. from a Cs137 source at
levels recommended to control fruit flies (0, 150, 300 Gy) and then stored at 10 °C and 90-95% relative humidity (RH) for 36 days,
followed by an addnl. 20 days at 20 °C to simulate marketing conditions. Stored fruit treated with 300 Gy had less water loss
compared to other treatments. Irradn. treatments had no consistent effect on total sol. solids (TSS) and titratable acidity. Stem end
breakdown and peel pitting were slightly higher in fruits treated with 300 Gy at the end of the storage period. Irradiated fruits had higher
total phenolic content than controls during storage. Fruits irradiated with 300 Gy had higher flavanone content (naringin, narirutin and
total flavanones) compared with control, immediately after irradn. and at the end of the storage. Organoleptic characters were more
affected by storage than by irradn. treatments. Sensory panel preferred fruits exposed to 300 Gy irradn. after the storage compared
to other treatments. Irradn. may be useful in retaining the beneficial flavanones that have been shown to have preventative effect on
degenerative diseases in addn. to insect control.
Answer 820:
Protein and cDNA sequences modified dominant-negative Mazus chalcone synthase and uses therefor. Hanummappa,
Mamatha; Choi, Goh; Choi, Giltsu. (Korea Kumho Petrochemical Co., Ltd, S. Korea). U.S. Pat. Appl. Publ. (2004), 18 pp.
CODEN: USXXCO US 2004038407 A1 20040226 Patent written in English. Application: US 2002-224493 20020821. Priority: .

US 20040038407 A1 20040226 US 2002-224493 20020821
US 7049427 B2 20060523
JP 2004065209 A 20040304 JP 2002-233324 20020809
JP 3734463 B2 20060111
EP 1394248 A1 20040303 EP 2002-255669 20020814
flavanone
TR, BG, CZ, EE, SK

CN 1478894 A 20040303 CN 2002-141485 20020830
KR 2002087927 A 20021123 KR 2002-69616 20021111
US 2002-224493 A 20020821
JP 2002-233324 A 20020809
Abstract
The invention includes modified Mazus chalcone synthase (CHS) nucleic acids, which encode a modified chalcone synthase that has
alanine instead of cysteine at the 165 th amino acid of Mazus CHS and either glycine or lysine instead of methionine at the 138 th
amino acid of Mazus CHS. The property of the encoded modified Mazus CHS is characterized by its dominant-neg. inhibition of CHS.
The invention also includes plants having at least one cell expressing the modified Mazus CHS. Such plants are characterized by the
decreased content of anthocyanins. The invention also includes vectors comprising at least a portion of the modified Mazus CHS
nucleic acids. The invention also includes methods using such vectors for producing plants having the decreased content of
anthocyanins.
Answer 821:
Effect of Antioxidant Flavanone, Naringenin, from Citrus junos on Neuroprotection. Heo, Ho Jin; Kim, Dae-Ok; Shin, Soo
Cheol; Kim, Mi Jeong; Kim, Byung Gee; Shin, Dong-Hoon. Department of Food Science and Technology, Cornell University,
Geneva, NY, USA. Journal of Agricultural and Food Chemistry (2004), 52(6), 1520-1525. Publisher: American Chemical Society,
Abstract
Amyloid β protein (Aβ)-induced free radical-mediated neurotoxicity is known as a leading hypothesis for a cause of Alzheimer's
disease. Aβ increased free radical prodn. and lipid peroxidn. in PC12 nerve cells, resulting in apoptosis and cell death. The protective
effect of naringenin, a major flavanone constituent isolated from Citrus junos, against Aβ-induced neurotoxicity was investigated using
PC12 cells. Pretreatment with isolated naringenin and vitamin C prevented the generation of the Aβ-induced reactive oxygen species.
Naringenin resulted in the decrease of Aβ toxicity in a manner of concn. dependence, which was assessed by the
3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. However, treatment with these antioxidants inhibited the Aβ-induced
neurotoxic effect. The antiamnestic activity of naringenin in vivo was also evaluated using ICR mice with amnesia induced by
scopolamine (1 mg/kg body wt.). Naringenin, when administered to ICR mice at 4.5 mg/kg body wt., significantly ameliorated
scopolamine-induced amnesia as measured in the passive avoidance test. Therefore, these results indicate that micromol. Aβ-induced
in vitro oxidative cell stress is reduced by naringenin and naringenin may be a useful chemopreventive agent against a
neurodegenerative disease such as Alzheimer's disease.
Answer 822:
Suppression of infection-induced endotoxin shock in mice by a Citrus flavanone naringin. Kawaguchi, Kiichiro; Kikuchi,
Sei-ichi; Hasunuma, Ryoichi; Maruyama, Hiroko; Ryll, Roland; Kumazawa, Yoshio. Medicinal Plant Garden, School of
flavanone
Pharmaceutical Sciences, Kitasato University, Japan. Planta Medica (2004), 70(1), 17-22. Publisher: Georg Thieme Verlag,
Abstract
The protective effect of the Citrus flavanone naringin was demonstrated in an endotoxin shock model based on Salmonella infection.
I.p. infection with 108 CFU Salmonella typhimurium aroA caused lethal shock in lipopolysaccharide (LPS) -responder but not
LPS-non-responder mice. Administration of 1 mg naringin 3 h before infection resulted in protection from lethal shock, similar to
LPS-non-responder mice. The protective effect of naringin was time- and dose-dependent. Treatment with naringin resulted not only in
a significant decrease in bacterial nos. in spleens and livers, but also in a decrease in plasma LPS levels. In addn., naringin markedly
suppressed TNF-α and normalized the activated states of blood coagulation factors such as prothrombin time, fibrinogen concn. and
platelet nos. caused by infection. Interestingly, treatment with naringin suppressed high levels of sol. CD14 and high mobility group-1
mol. caused by infection.
Answer 823:
Metabolism of 8-prenylnaringenin, a potent phytoestrogen from hops (Humulus lupulus), by human liver microsomes.
Nikolic, Dejan; Li, Yongmei; Chadwick, Lucas R.; Grubjesic, Simonida; Schwab, Pia; Metz, Peter; van Breemen, Richard B.
Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, Chicago, IL, USA. Drug Metabolism
and Disposition (2004), 32(2), 272-279. Publisher: American Society for Pharmacology and Experimental Therapeutics, CODEN:
DMDSAI ISSN: 0090-9556. Journal written in English. CAN 141:16823 AN 2004:141147 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
The female flowers of hops are used throughout the world as a flavoring agent for beer. Recently, there has been increasing interest
in the potential estrogenic properties of hop exts. Among the possible estrogenic compds. in hops, 8-prenylnaringenin is perhaps most
significant due to its high in vitro potency exceeding that of other known phytoestrogens. Since data regarding the pharmacokinetic
properties of this compd. are lacking, we investigated the in vitro metab. of 8-prenylnaringenin by human liver microsomes. A total of
12 metabolites were identified, and biotransformation occurred on the prenyl group and the flavanone skeleton. The major site of
oxidn. was on the terminal Me groups, and of the two possible isomers, the trans isomer was more abundant. The double bond on the
prenyl group was also oxidized to an epoxide that was opened by intramol. reaction with the neighboring hydroxyl group. On the
flavanone skeleton, the major site of oxidn. was at 3' position on the B ring. Other metabolites included oxidn. at carbon-3 as well as
desatn. of the C ring to produce 8-prenylapigenin. An unusual hydroxy quinone product formed by ipso hydroxylation of the B ring of
8-prenylnaringenin was also detected. This product was probably an intermediate for the B ring cleavage product, 8-prenylchromone.
Answer 824:
Synthesis, fungicidal activity and quantitative structure-activity relationships of novel flavanone derivatives. Yang,
Guang-Fu; Ding, Yu; Yang, Hua-Zheng; Wu, Xiao-Jun. College of Chemistry, Central China Normal University, Wuhan, Peop.
Rep. China. Gaodeng Xuexiao Huaxue Xuebao (2004), 25(1), 71-75. Publisher: Gaodeng Jiaoyu Chubanshe, CODEN: KTHPDM
SciFinder (R))
Abstract
flavanone
Fourteen novel flavanone derivs. I (R = Me, Cl; R' = Cl, NO2, Me, OMe, OCH2Ph, OCH2Ph-4-Cl) were designed and synthesized, and
structures were confirmed by 1H NMR, MS and elemental anal. Title compds. fungicidal IC50 in vitro against rice blast disease were
tested and the quant. relationship between their structures and fungicidal activities was analyzed by using comparative mol. field anal.
(CoMFA) and Hansch-Fujita approach. The results show that the hydrophobicity, polarity effect and the energy of the highest
unoccupied orbital are very important to fungicidal activity. If the mol. was easy to polarize and had a lower LUMO energy, it would
show a high fungicidal activity. Correlation results show that lgK is the most suitable parameter to describe the hydrophobicity of the
title compds. compared to two other hydrophobic parameters, .sum.π and clgP. The results of 3D-QSAR anal. suggests that the
introduction of steric bulk group onto the 2,3,4-position and small steric bulk onto the 6-position of B ring will be favorable to the
activity of the compd. The CoMFA analyses on the electronic property requirement are consistent with those derived from the
Hansch-Fujita approach.
R'
O
R
O I
Answer 825:
Candidate gene analysis of anthocyanin pigmentation loci in the Solanaceae. De Jong, W. S.; Eannetta, N. T.; De Jong, D.
M.; Bodis, M. Department of Plant Breeding, Cornell University, Ithaca, NY, USA. Theoretical and Applied Genetics (2004),
108(3), 423-432. Publisher: Springer-Verlag, CODEN: THAGA6 ISSN: 0040-5752. Journal written in English. CAN 141:2031 AN
Abstract
Crop species in the Solanaceae, which includes tomato (Lycopersicon esculentum), potato (Solanum tuberosum), pepper (Capsicum
spp.), and eggplant (S. melongena), exhibit natural variation in the types, levels, and tissue-specific expression patterns of
anthocyanin pigments. While the identities of the genes underpinning natural variation in anthocyanin traits in these crops are largely
unknown, many structural genes and regulators of anthocyanin biosynthesis have been isolated from the solanaceous ornamental
species Petunia. To identify candidate genes that may correspond to loci controlling natural variation in the four crops, 13
anthocyanin-related genes were localized on a tomato F2 genetic map. Gene map positions were then compared to mapped mutants in
tomato and through comparative genetic maps to natural variants in potato, eggplant, and pepper. Similar map positions suggest that
the tomato mutants anthocyaninless, entirely anthocyaninless, and anthocyanin gainer correspond to flavonoid 3'5'-hydroxylase
(f3'5'h), anthocyanidin synthase, and the Petunia Myb domain transcriptional regulatory gene an2, resp. Similarly potato R, required
for the prodn. of red pelargonidin-based pigments, P, required for prodn. of purple delphinidin-based pigments, and I, required for
tissue-specific expression in tuber skin, appear to correspond to dihydroflavonol 4-reductase, f3'5'h and an2, resp. The map location
of an2 also overlaps pepper A and eggplant fap10.1, lla10.1, lra10.1, sa10.1, pa10.1 and ca10.1, suggesting that a homologous
regulatory locus has been subjected to parallel selection in the domestication of many solanaceous crops. To test the hypothesis that
tomato anthocyaninless corresponds to f3'5'h, a portion of the gene was sequenced. A premature stop codon was obsd. in an
anthocyaninless mutant, but not in wild-type.
Answer 826:
flavanone
The chemistry and pharmacology of the genus Dorstenia (Moraceae). Ngadjui, Bonaventure T.; Abegaz, Berhanu M.
Department of Organic Chemistry, Faculty of Science, University of Yaounde 1, Yaounde, Cameroon. Studies in Natural
Products Chemistry (2003), 29(Bioactive Natural Products (Part J)), 761-805. Publisher: Elsevier Science B.V., CODEN: SNPCE2
(R))
Abstract
A review. The genus Dorstenia contains many plants that are used as anti-infection, anti-snakebite and anti-rheumatic remedies in the
medicinal plant therapy of several countries in Africa, Central and South America. The genus is now recognized as a rich source of
prenyl and geranyl-substituted coumarins, chalcones, flavanones, flavones and flavonols. Three naturally occurring styrenes were
reported from D. barnimiana. The geranyl substituted furocoumarin, O-[3-(2,2-dimethyl-3-oxo-2H-furan-5-yl)butyl]bergaptol, has been
found in many species. D. poinsettifolia furnished the unusual substituted 4-phenyldihydrofurocoumarin. Prenylated and geranylated
flavonoids have so far been reported only from African Dorstenia species. 5, 3'-Digeranyl-3,4,2',4'-tetrahydroxychalcone isolated
from D. proropens, is the only example of a bis-geranylated chalcone in the literature. A part from 7,8-
(2,2-dimethylpyrano-4'-methoxyflavanone ( dorspoinsettifolin) from D. poinsettifolia and 3',4'-
(2,2-dimethylpyrano-6-prenyl-7-hydroxyflavanone (dinklagin A) from D. dinklagei, all flavanone derivs. named dorsmanins A - J
described here are from D. mannii. These dorsmanins appear to be derived from 6,8-diprenyl-5,7,3',4'-tetrahydroxyflavanone and a
possible biosynthetic scheme for them is presented. D. Zenkeri yield a bichalcone deriv. which is believed to arise from dorstenone
another prenylated bichalcone isolated from D. barteri. The latter is probably formed via an enzymic Diels-Alder reaction of
3'-prenyl-4,2',4'-trihydroxychalcone (isobavachalcone) and its dehydroderivative. D. psilurus provided all the triprenylated flavonoids
found so far in Dorstenia and, of these, dorsilurin E is unique having ring B of the flavonoid structure modified to a dienone. The
pharmacol. data on this genus are scanty. Exts. of D. multiradiata show antileishmanial activity. Exts. and /or compds. from other
species show anti-inflammatory, analgesic, anti-oxidant and citotoxic activities.
Answer 827:
Sedative and sleep-enhancing properties of linarin, a flavonoid-isolated from Valeriana officinalis. Fernandez, Sebastian;
Wasowski, Cristina; Paladini, Alejandro C.; Marder, Mariel. Facultad de Farmacia y Bioquimica, Instituto de Quimica y Fisicoquimica
Biologicas, Buenos Aires, Argent. Pharmacology, Biochemistry and Behavior (2004), 77(2), 399-404. Publisher: Elsevier Science
Inc., CODEN: PBBHAU ISSN: 0091-3057. Journal written in English. CAN 140:264360 AN 2004:78728 CAPLUS (Copyright
Abstract
We have recently reported the presence of the anxiolytic flavone 6-methylapigenin (MA) and of the sedative and sleep-enhancing
flavanone glycoside 2S (-) hesperidin (HN) in Valeriana officinalis and Valeriana wallichii. MA, in turn, was able to potentiate the
sleep-inducing properties of HN. The present paper reports the identification in V. officinalis of the flavone glycoside linarin (LN) and
the discovery that it has, like HN, sedative and sleep-enhancing properties that are potentiated by simultaneous administration of
valerenic acid (VA). These effects should be taken into account when considering the pharmacol. actions of valeriana exts.
Answer 828:
Colonic metabolism of dietary polyphenols: influence of structure on microbial fermentation products. Rechner, Andreas
R.; Smith, Martin A.; Kuhnle, Gunter; Gibson, Glenn R.; Debnam, Edward S.; Srai, S. Kaila S.; Moore, Kevin P.; Rice-Evans, Catherine
A. School of Biomedical Sciences, Wolfson Centre for Age-Related Diseases, Antioxidant Research Group, King's College London,
London, UK. Free Radical Biology & Medicine (2004), 36(2), 212-225. Publisher: Elsevier, CODEN: FRBMEH ISSN: 0891-5849.
flavanone
Abstract
The metab. of chlorogenic acid, naringin, and rutin, representative members of three common families of dietary polyphenols, the
hydroxycinnamates, the flavanones, and the flavonols, resp., was studied in an in vitro mixed culture model of the human colonic
microflora. Time- and concn.-dependent degrdn. of all three compds. was obsd., which was assocd. with the following metabolic
events after cleavage of the ester or glycosidic bond: redn. of the aliph. double bond of the resulting hydroxycinnamate caffeic acid
residue; dehydroxylation and ring fission of the heterocyclic C-ring of the resulting deglycosylated flavanone, naringenin, and of the
deglycosylated flavonol, quercetin (which differed depending on the substitution). The metabolic events, their sequences, and major
phenolic end products, as identified by GC-MS or LC-MS/MS, were elucidated from the structural characteristics of the investigated
compds. The major phenolic end products identified were 3-(3-hydroxyphenyl)-propionic acid for chlorogenic acid,
3-(4-hydroxyphenyl)-propionic acid and 3-phenylpropionic acid for naringin, and 3-hydroxyphenylacetic acid and
3-(3-hydroxyphenyl)-propionic acid for rutin. The degree of degrdn. of the compds. studied was significantly influenced by the
substrate concn. as well as individual variations in the compn. of the fecal flora. The results support extensive metab. of dietary
polyphenols in the colon, depending on substrate concn. and residence time, with resultant formation of simple phenolics, which can be
considered biomarkers of colonic metab. if subsequently absorbed. It is also apparent that a relatively small no. of phenolic degrdn.
products are formed in the colon from the diverse group of natural polyphenols.
Answer 829:
Preparation of optically-active flavanones or chromanones from dithiane or dithiolane derivatives. Noda, Yoshihiro. (Nihon
University, Japan). Jpn. Kokai Tokkyo Koho (2004), 10 pp. CODEN: JKXXAF JP 2004026726 A 20040129 Patent written in
Japanese. Application: JP 2002-185820 20020626. Priority: . CAN 140:128274 AN 2004:76471 CAPLUS (Copyright (C) 2008

JP 2004026726 A 20040129 JP 2002-185820 20020626
JP 2002-185820 20020626
Abstract
The optically-active flavanones or chromanones I (R1, R2 = H, OH, alkoxy, alkyl, hydroxyalkyl; R3 = Me, Ph which may be
substituted with OH and/or alkoxy) are prepd. by (1) treating dithiane or dithiolane derivs. II (R = H; R1, R2 = same as above; X = F,
Cl; n = 2, 3) (III) with bases and reacting with optically-active epoxides IV (R3 = same as above), (2) cyclizing the resulting
optically-active alc. II (R = CH2CHR3OH; R1, R2, R3, X, n = same as above) (V) upon treatment with bases, and (3) hydrolyzing the
resulting optically-active spiro compd. VI (R1, R2, R3, n = same as above). BuLi was added dropwise to a THF soln. of III (R1 = R2 =
H, X = F, n = 3), prepd. by reacting 2-FC6H4CHO with HS(CH2)3SH, at -18° and the reaction mixt. was stirred for 3 h. The reaction
mixt. was treated with (S)-(-)-propylene oxide for a day to give 71.0% (-)-V (R1 = R2 = H, R3 = Me, X = F, n = 3). This was treated with
Me3COK at 80° for 30 min and further treated with addnl. Me3COK under reflux for 1 h to give 90.7% (-)-VI (R1 = R2 = H, R3 = Me, n =
3). A mixt. of HgCl2, CaCO3, and MeCN/H2O was stirred at room temp. for 1 h and treated with an acetone soln. of the spiro compd.
for 3 h to give 74.0% (-)-I (R1 = R2 = H, R3 = Me).
flavanone
S CH 2 S
n
O
R1 R1
R
*
O R3 X
R2 I R2 II
S CH 2 S
n
R1
O *
*
O R3
R3 IV R2 VI
Answer 830:
Functional components in citrus beverages. Patil, Bhimanagouda S. Kingsville Citrus Center, Texas A and M University,
Weslaco, TX, USA. ACS Symposium Series (2004), 871(Nutraceutical Beverages), 103-122. Publisher: American Chemical
Society, CODEN: ACSMC8 ISSN: 0097-6156. Journal written in English. CAN 140:286508 AN 2004:73018 CAPLUS
Abstract
Citrus beverages are often part of our daily diet. Recent animal, case and cohort control as well as epidemiol. studies have shown
that certain functional components [carotenoids (lycopene and β-carotene), limonoids, flavones (naringin and naringin rutinoside),
folate, and vitamin C] of citrus prevent chronic diseases such as cancer and cardiovascular diseases. Functional components from 3
single strength com. "Rio Red" grapefruit (Citrus paradisi Macf.) juice products namely cartons (100% pure fresh juice and not from
conc.), cans (100% juice from conc.), and cocktails (35% juice from conc.), were analyzed by reverse phase liq. chromatog. The
levels of vitamin C significantly decreased when half-gal grapefruit juice cartons were stored at 4°C for six weeks, but the levels of
limonin 17-β-D glucopyranoside (LG) were not affected during the same period. Total flavanone and lycopene levels were significantly
higher at 6 wk compared to initial levels. Although a significant loss of vitamin C levels was found when cans were stored at room
temp. (24°C) for 12 mo, LG levels were markedly increased during the same period. Furthermore, total flavanone and carotenoid
levels were changed during storage, but no specific trend was obsd. When cocktail in polyethylene toluene (PET) containers was
stored at room temp., the levels of vitamin C were significantly decreased; however, LG and lycopene levels were increased. Our
expts. suggest that the functional components in grapefruit juice change during storage, depending on the container used. To remain
competitive in international and national markets, optimization of these components may be important for the processing industry.
Answer 831:
Validated high-performance liquid chromatographic method utilizing solid-phase extraction for the simultaneous
flavanone
determination of naringenin and hesperetin in human plasma. Kanaze, Feras Imad; Kokkalou, Eugene; Georgarakis, Manolis;
Niopas, Ioannis. School of Health Sciences, Department of Pharmacy, Aristotle University of Thessaloniki, Thessaloniki, Greece.
Abstract
Naringenin and hesperetin, the aglycons of the flavanone glucosides naringin and hesperidin occur naturally in citrus fruits. They exert
a variety of pharmacol. effects such as antioxidant, blood lipid-lowering, anticarcinogenic and inhibit selected cytochrome P 450
enzymes resulting in drug interactions. A specific, sensitive, precise, and accurate solid-phase extn. HPLC assay for the
simultaneous detn. of naringenin and hesperetin in human plasma was developed and validated. After addn. of 7-ethoxycoumarin as
internal std., plasma samples were incubated with β-glucuronidase/sulfatase, and the analytes were isolated from plasma by
solid-phase extn. using C18 cartridges and sepd. on a C8 reversed phase column with MeOH/H2O/HOAc (40:58:2, vol./vol./v) as the
eluent at 45°. The method was linear in the 10-300 ng/mL concn. range for both naringenin and hesperetin (r > 0.999). Recovery for
naringenin, hesperetin and internal std. was >76.7%. Intra- and inter-day precision for naringenin ranged from 1.4 to 4.2% and from 1.9
to 5.2%, resp., and for hesperetin ranged from 1.3 to 4.1% and from 1.7 to 5.1%, resp. Accuracy was better than 91.5 and 91.3% for
naringenin and hesperetin, resp.
Answer 832:
Inhibitory Effect of Some Flavonoids on Tumor Necrosis Factor-α Production in Lipopolysaccharide-Stimulated Mouse
Macrophage Cell Line J774.1. Mudiyanselage Theja Herath, Herath; Takano-Ishikawa, Yuko; Yamaki, Kohji. Industrial
Technology Institute, Colombo, Sri Lanka. Journal of Medicinal Food (2003), 6(4), 365-370. Publisher: Mary Ann Liebert, Inc.,
CODEN: JMFOFJ ISSN: 1096-620X. Journal written in English. CAN 141:167193 AN 2004:68470 CAPLUS (Copyright (C)
Abstract
Certain naturally occurring flavonoids affect immunoregulatory activities in vitro and in vivo against cytokine prodn. Since tumor
necrosis factor (TNF)-α is one of the major inflammatory cytokines, the effects of various dietary flavonoids on TNF- α prodn. in
lipopolysaccharide (LPS)-stimulated J774.1 cells were evaluated in vitro. Flavones, flavonols, and chalcone are the most potent
inhibitors of prodn. of TNF-α. Flavanone, naringenin, anthocyanidin, pelargodinin, and cyanidin exhibit moderate inhibitory activity. In
contrast, genistein isoflavone displays weak inhibition, while eriodictyol flavanone is inactive. It is clear that the double bond between
carbons 2 and 3 and the ketone group at position 4 of flavonoids are necessary for potent inhibitory effect. The difference in
inhibitory action appears to depend on the categorized subclass of flavonoids.
Answer 833:
Effect of flavonoids on feeding preference and development of the crucifer pest Mamestra configurata Walker. Onyilagha,
Joseph C.; Lazorko, Jennifer; Gruber, Margaret Y.; Soroka, Juliana J.; Erlandson, Martin A. Saskatoon Research Centre, Agriculture
and Agri-Food Canada, Saskatoon, SK, Can. Journal of Chemical Ecology (2004), 30(1), 109-124. Publisher: Kluwer
Academic/Plenum Publishers, CODEN: JCECD8 ISSN: 0098-0331. Journal written in English. CAN 140:401732 AN 2004:66446
Abstract
flavanone
Thirty-seven flavonoid compds. (9 flavones, 18 flavonols, 8 flavanones, and 2 flavanonols) were investigated for their effect on
feeding choice with bertha armyworm (Mamestra configurata Walker; BAW). Feeding choice was dependent upon subtle differences in
biochem. structure. Unsubstituted flavone and flavanone were the strongest feeding deterrents in the choice bioassay, while
7,4'-dihydroxyflavone and dihydroquercetin stimulated BAW to feed. The constitutive flavonoids of Brassica napus,
isorhamnetin-3-sophoroside-7-glucoside and kaempferol-3,7-diglucoside, were effective deterrents when supplemented at concns.
higher than endogenous levels. In a no-choice bioassay, flavone reduced both larval wt. as well as larval and pupal development time.
Answer 834:
Induction of antimicrobial 3-deoxyflavonoids in pome fruit trees controls fire blight. Halbwirth, Heidrun; Fischer, Thilo C.;
Roemmelt, Susanne; Spinelli, Francesco; Schlangen, Karin; Peterek, Silke; Sabatini, Emidio; Messina, Christian; Speakman,
John-Bryan; Andreotti, Carlo; Rademacher, Wilhelm; Bazzi, Carlo; Costa, Guglielmo; Treutter, Dieter; Forkmann, Gert; Stich, Karl.
Institute of Technical BioScience, Technical University of Vienna, Vienna, Austria. Zeitschrift fuer Naturforschung, C: Journal of
Biosciences (2003), 58(11/12), 765-770. Publisher: Verlag der Zeitschrift fuer Naturforschung, CODEN: ZNCBDA ISSN:
Abstract
Fire blight, caused by Erwinia amylovora, is a in pome fruit disease. Hitherto, an effective control could only be achieved by using
antibiotics, but this implies potential risks for human health, livestock and environment. A new approach allows transient inhibition of a
step in the flavonoid pathway, thereby inducing the formation of a novel antimicrobial 3-deoxyflavonoid controlling fire blight in apple
and pear leaves. This compd. is closely related to natural phytoalexins in sorghum. The approach does not only provide a safe
method to control fire blight: Resistance against different pathogens is also induced in other crop plants. Treatment with
prohexadione-Ca led to luteoliflavan accumulation in apple leaves. Synthetic luteoforol controlled E. amylovora, in vitro. An overview
is given of the flavanone 4-reductase activity of various crops.
Answer 835:
Synthesis and biological activity of some new 3,5-diaryl-1-phenyl/isonicotinoyl-2-pyrazolines and 3,5-diaryl-6-carbethoxy

cyclohexenone derivatives. Vijayvergiya, Deepika; Kothari, Seema; Verma, B. L. Department of Chemistry, Faculty of
Science, M.L. Sukhadia University, Udaipur, India. Indian Journal of Heterocyclic Chemistry (2003), 13(2), 105-110. Publisher:
Prof. R. S. Varma, CODEN: IJCHEI ISSN: 0971-1627. Journal written in English. CAN 141:225382 AN 2004:38752 CAPLUS
Abstract
Chalcone dibromide on treatment with Ph hydrazine hydrochloride or isonicotinic acid hydrazide afforded the corresponding
3,5-diaryl-1-phenyl/isonicotinoyl-2-pyrazolines, e.g., I, which have also been obtained from chalcones under similar conditions. Further,
some of the chalcones on treatment with acetoacetic ester have been converted to the corresponding
3,5-diaryl-6-carbethoxycyclohex-2-en-1-ones, e.g., I. Structure elucidation has been done on the basis of elemental anal. and spectral
studies. The synthesized compds. have been screened for their antibacterial and the pyrazolines for both antibacterial and herbicidal
activities.
flavanone
HO Br
Br
N
N
O OMe
N
I
OH OMe
CO 2 Et
O II
Answer 836:
An improved procedure for the isomerisation of 2'-hydroxy-substituted chalcones to flavanones using silica
supported-BiCl3 under dry conditions. Ahmed, Naseem; Ansari, W. H. Dep. Chem., Aligarh Muslim Univ., Aligarh, India.
Journal of Chemical Research, Synopses (2003), (9), 572-573. Publisher: Science Reviews, CODEN: JRPSDC ISSN: 0308-2342.
Abstract
The isomerization of 2'-hydroxychalcones to their corresponding flavanones, in good to excellent yield using silica supported-Bi(III)
chloride as a catalyst under dry conditions at 70-80°C is reported.
Answer 837:
Synthesis and fungicidal activity of flavanone derivatives containing isopentenyl group. Hu, Li-Hong; Qin, Zhang-Lan; Li,
Chao; Huang, Qin; Wang, Fen-Hua. Department of Chemistry, Central China Normal University, Wuhan, Peop. Rep. China.
flavanone
Yingyong Huaxue (2003), 20(12), 1161-1165. Publisher: Kexue Chubanshe, CODEN: YIHUED ISSN: 1000-0518. Journal written
in Chinese. CAN 140:321205 AN 2004:11346 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
Twelve isopentenyl flavanone derivs. were synthesized by the Friedel-Crafts reaction of isopentenyl cinnamic acid with substituted
phenols, giving the products with yield 69% to 30%. The structures of title compds. were confirmed by elemental anal., IR, 1H NMR
and MS. The phys., chem. and spectroscopic properties of these compds. were characterized. Biol. test showed that some of
compds. had good fungicidal activity towards Anthracnosis cucumaria, Rhizotonia Solani Kuhn, Piricularia oryzae Cav, Fusarium
graminearum Schwabe. It indicated that isopentenyl substituents might eventually enhance fungicidal activity of this kind of compds.
Answer 838:
Mechanistic Studies on Three 2-Oxoglutarate-dependent Oxygenases of Flavonoid Biosynthesis: anthocyanidin synthase,

flavonol synthase, and flavanone 3β-hydroxylase. Turnbull, Jonathan J.; Nakajima, Jun-ichiro; Welford, Richard W. D.;
Yamazaki, Mami; Saito, Kazuki; Schofield, Christopher J. The Dyson Perrins Laboratory, The Oxford Centre for Molecular Sciences,
Oxford, UK. Journal of Biological Chemistry (2004), 279(2), 1206-1216. Publisher: American Society for Biochemistry and
Molecular Biology, CODEN: JBCHA3 ISSN: 0021-9258. Journal written in English. CAN 140:249135 AN 2004:10881 CAPLUS
Abstract
Anthocyanidin synthase (ANS), flavonol synthase (FLS), and flavanone 3β-hydroxylase (FHT) are involved in the biosynthesis of
flavonoids in plants and are all members of the family of 2-oxoglutarate- and ferrous iron-dependent oxygenases. ANS, FLS, and FHT
are closely related by sequence and catalyze oxidn. of the flavonoid "C ring"; they have been shown to have overlapping substrate
and product selectivities. In the initial steps of catalysis, 2-oxoglutarate and dioxygen are thought to react at the ferrous iron center
producing succinate, carbon dioxide, and a reactive ferryl intermediate, the latter of which can then affect oxidn. of the flavonoid
substrate. Here the authors describe work on ANS, FLS, and FHT utilizing several different substrates carried out in 18O2/16OH2,
16O2/18OH2, and 18O2/18OH2 atmospheres. In the 18O2/16OH2 atmosphere close to complete incorporation of a single 18O label
was obsd. in the dihydroflavonol products (e.g. (2R,3R)-trans-dihydrokaempferol) from incubations of flavanones (e.g. (2S)naringenin)
with FHT, ANS, and FLS. This and other evidence supports the intermediacy of a reactive oxidizing species, the oxygen of which
does not exchange with that of water. In the case of products formed by oxidn. of flavonoid substrates with a C-3 hydroxyl group
(e.g. (2R,3R)-trans-dihydroquercetin), the results imply that oxygen exchange can occur at a stage subsequent to initial oxidn. of the
C-ring, probably via an enzyme-bound C-3 ketone/3,3-gem-diol intermediate.
Answer 839:
Method to increase isoflavonoid levels through genetic engineering to modulate to gene expression in phenylpropanoid
biosynthetic pathway in transgenic plants. McGonigle, Brian; Odell, Joan T. (E. I. Du Pont de Nemours & Co., USA). PCT Int.
Appl. (2003), 55 pp. CODEN: PIXXD2 WO 2003106633 A2 20031224 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA,
BB, BG, BR, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN,
IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NI, NO, NZ, OM, PH, PL, PT, RO, RU,
SC, SD, SE, SG, SK, SL, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH,
CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent
flavanone

WO 2003106633 A2 20031224 WO 2003-US18663 20030612
WO 2003106633 A3 20041007
DZ, EC, EE, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR,
LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NI, NO, NZ, OM, PH, PL, PT, RO, RU, SC, SD, SE,
SG, SK, SL, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW
US 20040006795 A1 20040108 US 2003-459159 20030611
US 7189895 B2 20070313
AU 2003236501 A1 20031231 AU 2003-236501 20030612
US 2002-388280P P 20020613
WO 2003-US18663 W 20030612
Abstract
This invention pertains to methods of increasing isoflavonoid prodn. in isoflavonoid-producing plants by transforming plants with at
least one construct expressing at least a portion of a flavanone 3-hydroxylase, a C1 myb transcription factor, and an R-type myc
transcription factor that regulate expression of genes in the phenylpropanoid pathway. Specifically, isoflavone levels in Glycine max
(soybean) are increased via metabolic engineering of the complex phenylpropanoid biosynthetic pathway through suppression of
flavanone 3-hydroxylase (F3H) to block the anthocyanin branch of the pathway, in combination with expressing C1/R fusion protein
CRC to activate other related gene expression. The F3H suppression vector AC21 contains a portion of FSH gene (antisense
presumably, not specified, under the control of a seed-specific promoter) that can promote formation of a stem loop structure and thus
inhibit F3H gene expression. The CRC vector (pOY135) encodes a fusion protein (under the control of phaseolin promoter) which
contain corn C1 myb domain to amino acid 125, the entire coding region of the Lc allele of R, and C1 transcription activation domain
(from amino acid 126 to the C-terminus of C1). Higher levels of isoflavones (4-times than wild-type), and decreased genistein and
increased the daidzein levels are detected in transgenic soybean seed.
Answer 840:
Constituents of the stem bark of Pongamia pinnata with the potential to induce quinone reductase. [Erratum to document
cited in CA139:320060]. Carcache-Blanco, Esperanza J.; Kang, Young-Hwa; Park, Eun Jung; Su, Bao-Ning; Kardono, Leonardus B.
S.; Riswan, Soedarsono; Fong, Harry H. S.; Pezzuto, John M.; Kinghorn, A. Douglas. Program for Collaborative Research in the
Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois,
Chicago, IL, USA. Journal of Natural Products (2004), 67(1), 126. Publisher: American Chemical Society, CODEN: JNPRDF
SciFinder (R))
Abstract
flavanone
On page 1197, the relative stereochem. of compd. 5 was incorrect; the correct structure is given. On pages 1200-1201, the correct
trivial name for compd. 6 [7,2',6'-trimethoxy-6",6"-dimethylpyrano-(3',4':2",3")-chalcone] is 7-O-methylpraecansone B, and not
7-methoxypraecansone B as given.
Answer 841:
Variation in chalcononaringenin 2'-O-glucoside content in the petals of carnations (Dianthus caryophyllus) bearing yellow
flowers. Yoshida, Hiroyuki; Itoh, Yoshio; Ozeki, Yoshihiro; Iwashina, Tsukasa; Yamaguchi, Masa-atsu. Applied Plant Research
Center, Japan Tobacco, Inc., Oyama, Tochigi, Japan. Scientia Horticulturae (Amsterdam, Netherlands) (2004), 99(2), 175-186.
Publisher: Elsevier Science B.V., CODEN: SHRTAH ISSN: 0304-4238. Journal written in English. CAN 140:403403 AN
Abstract
Chalcononaringenin 2'-O-glucoside (Ch2'G) was found to be the major pigment mol. in the petals of carnations bearing yellow flowers.
The concn. of this pigment varied from 5.5 to 100.0% (relative value with amts. in the line '7154-03' assumed to be 100%) in 31
carnation genotypes investigated. The transcription of both phenylalanine ammonia-lyase (PAL) and chalcone synthase (CHS) genes
was active in the petals of both yellow carnation flowers and a cyanic control cultivar. The transcripts derived from the
chalcone-flavanone isomerase (CHI) gene in the petals of yellow carnation flowers were below the level detectable by Northern blot
anal., but could be detected by RT-PCR. This is possible to produce subtle amts. of CHI protein translated from suspicious amts. of
the mRNA to catalyze chalcone, resulting in the variation of the concn. of Ch2'G. Other probable factors caused to the variation
include the amt. of substrates supplying the flavonoid biosynthetic pathway, spontaneous isomerization flowing over the CHI step
producing flavonol derivs., and chalcone 2'-glucosyltransferase (CHGT) activity.
Answer 842:
Separation of flavanone enantiomers by simulated moving bed (SMB) process. Katsuyama, Hirokazu; Uemura, Yoshimitsu;
Yoshida, Masahiro; Hatate, Yasuo. Grad. Sch. Appl. Chem. Eng., Kagoshima Univ., Japan. Kagoshima Daigaku Kogakubu
Kenkyu Hokoku (2003), 45 79-85. Publisher: Kagoshima Daigaku Kogakubu, CODEN: KDKKBA ISSN: 0451-212X. Journal written
in Japanese. CAN 140:43699 AN 2003:986115 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
Chromatog. sepns. are an expanding technol. for the sepn. of high value products, particularly in the area of pharmaceutics, food, and
fine chems. The simulated moving bed (SMB) process as a continuous chromatog. sepn. process is an interesting alternative to
conventional batch chromatog., and gained more and more impact recently. In this paper, flavanone enantiomers were sepd. by
simulated moving bed process. The best purities of the products obtained were 100% for the raffinate and 82% for the ext.
Answer 843:
An Arabidopsis thaliana T-DNA mutagenized population (GABI-Kat) for flanking sequence tag-based reverse genetics.
Rosso, Mario G.; Li, Yong; Strizhov, Nicolai; Reiss, Bernd; Dekker, Koen; Weisshaar, Bernd. GABI-Kat, Max Planck Institute for
Plant Breeding Research, Cologne, Germany. Plant Molecular Biology (2003), 53(1-2), 247-259. Publisher: Kluwer Academic
Publishers, CODEN: PMBIDB ISSN: 0167-4412. Journal written in English. CAN 140:247814 AN 2003:985380 CAPLUS
flavanone
Abstract
The GABI-Kat population of T-DNA mutagenized Arabidopsis thaliana lines with sequence-characterized insertion sites is used
extensively for efficient progress in plant functional genomics. Here we provide details about the establishment of the material,
demonstrate the population's functionality and discuss results from quality control studies. T-DNA insertion mutants of the accession
Columbia (Col-0) were created by Agrobacterium tumefaciens-mediated transformation. To allow selection of transformed plants under
greenhouse conditions, a sulfadiazine resistance marker was employed. DNA from leaves of T1 plants was extd. and used as a
template for PCR-based amplification of DNA fragments spanning insertion site borders. After sequencing, the data were placed in a
flanking sequence tag (FST) database describing which mutant allele was present in which line. Anal. of the distribution of T-DNA
insertions revealed a clear bias towards intergenic regions. Insertion sites appeared more frequent in regions in front of the ATG and
after STOP codons of predicted genes. Segregation anal. for sulfadiazine resistance showed that 62% of the transformants contain an
insertion at only one genetic locus. In quality control studies with gene-specific primers in combination with T-DNA primers, 76% of
insertions could be confirmed. Finally, the functionality of the GABI-Kat population was demonstrated by exemplary confirmation of
several new transparent testa alleles, as well as a no. of other mutants, which were identified on the basis of the FST data.
Answer 844:
Antiproliferative activity of various flavonoids and related compounds: additive effect of interferon-αg2b. Blank, Viviana C.;
Poli, Cecilia; Marder, Mariel; Roguin, Leonor P. Facultad de Farmacia y Bioquimica, Instituto de Quimica y Fisicoquimica Biologicas,
Buenos Aires, Argent. Bioorganic & Medicinal Chemistry Letters (2004), 14(1), 133-136. Publisher: Elsevier Science B.V.,
CODEN: BMCLE8 ISSN: 0960-894X. Journal written in English. CAN 140:246359 AN 2003:981464 CAPLUS (Copyright (C)
Abstract
The antiproliferative activity of several natural and synthetic flavonoids and some related compds. was evaluated in vitro against a
cell line derived from a human cervical carcinoma (WISH cells). According to their activities, the most potent derivs. were
2'-nitroflavone (14), 2',6-dinitroflavone (15) and the Bu ester of caffeic acid (29). When these compds. were tested in the presence of
recombinant human interferon-α2b (rhIFN-α2b), a cytokine exhibiting an antimitogenic action on WISH cells, an additive effect on cell
growth inhibition was obsd. Time course studies of the antiproliferative action exerted by the active derivs. or the rhIFN-α2b
suggested that these compds. induced cell death.
Answer 845:
Mass spectrometric methods for characterization and differentiation of isomeric O-diglycosyl flavonoids. Cuyckens, F.;
Ma, Y. L.; Van den Heuvel, H.; Claeys, M. Department of Pharmaceutical Sciences, University of Antwerp (UIA), Antwerp, Belg.
Advances in Mass Spectrometry (2001), 15 891-892. Publisher: John Wiley & Sons Ltd., CODEN: AMSPAH ISSN: 0568-000X.
Abstract
Tandem mass spectrometric methods were evaluated for the characterization of the interglycosidic linkage type and differentiation of
four pairs of isomeric flavonoid O-diglycosides. Metastable ion spectra of the protonated rhoifolin and its isomer, isorhoifolin differ by
the interglycosidic linkage type between the two monosaccharides. Different relative abundances of the Y0 (protonated aglycon) and
flavanone
Y1 (loss of 146 units) ions was also obsd. in the spectra of kaempferol-7-O-neohesperidoside and nicotiflorin. Another significant
difference is that a weak ion (Y*) can only be seen in the spectra of nicotiflorin. The Y*/Y1 ratio is much smaller for rutin, a flavonoid
3-O-rutinoside, than for hesperidin, a flavonoid 7-O-rutinoside. The isomeric flavonoids, naringin and narirutin, contain flavanone but
differ in the interglycosidic linkage type between rhamnose and glucose.
Answer 846:
Optically active high-molecular compounds. Nakano, Tamaki. (Japan Science and Technology Corporation, Japan). PCT Int.
Appl. (2003), 20 pp. CODEN: PIXXD2 WO 2003102039 A1 20031211 Designated States W: CA, JP, US. Designated States
RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR. Patent written in Japanese. Application: WO
2003-JP5726 20030507. Priority: JP 2002-132599 20020508. CAN 140:17462 AN 2003:972114 CAPLUS (Copyright (C) 2008

WO 2003102039 A1 20031211 WO 2003-JP5726 20030507
W: CA, JP, US
RW: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IT, LU, MC, NL, PT, RO, SE, SI,
SK, TR
CA 2485305 A1 20031211 CA 2003-2485305 20030507
EP 1528070 A1 20050504 EP 2003-728039 20030507
EP 1528070 B1 20071128
HU, SK
US 20050234267 A1 20051020 US 2004-513658 20041108
JP 2002-132599 A 20020508
WO 2003-JP5726 W 20030507
Abstract
The invention relates to optically active high-mol. compds. I and stationary-phase materials contg. the same, wherein Ar = arom. ring;
R1, R2 = H or org. group; R3, R4 = substituent; n = ≥2 integer; X = (CH2)m, arom. group, vinyl group, heteroatom, or
heteroatom-contg. group; and m = ≥0 integer, the compd. may have 2-4 R3s and/or 2-4 R4s which may be each the same or different
from each other. The high-mol. compds. exhibit optical activity by virtue of their stacking helical structures wherein the arom. groups
are distorted, thus being useful as optically active stationary phases for HPLC or polarized-light absorbers. Thus, 312.5 mg (-)-menthol
was treated with 0.3 g potassium hydride to give menthoxy potassium, 2.02 mmol dibenzofulvene were polymd. in the presence of 2.0
mL 0.2M of the resulting menthoxy potassium at -78° for 24 h to give a polymer with Mn 1070 and polydispersity 1.47, which was used
as a stationary phase for the sepn. of racemic compds., showing good efficiency.
flavanone
R1 R2
n
R3 R4
Ar Ar
X I
Answer 847:
Silibinin down-regulates survivin protein and mRNA expression and causes caspases activation and apoptosis in human
bladder transitional-cell papilloma RT4 cells. Tyagi, Anil K.; Agarwal, Chapla; Singh, Rana P.; Shroyer, Kenneth R.; Glode, L.
Michael; Agarwal, Rajesh. School of Pharmacy, Department of Pharmaceutical Sciences, University of Colorado Health Sciences
Center, Denver, CO, USA. Biochemical and Biophysical Research Communications (2003), 312(4), 1178-1184. Publisher:
Elsevier Science, CODEN: BBRCA9 ISSN: 0006-291X. Journal written in English. CAN 140:156969 AN 2003:940059 CAPLUS
Abstract
Bladder cancer is the fourth and eighth most common cancer in men and women in the United States, resp. Survivin, a member of
inhibitor of apoptosis protein (IAP) gene family, is deregulated in a wide range of malignancies, including carcinoma of the bladder
urothelium. Recent advances have identified survivin as a novel intervention target to induce apoptosis in cancer cells by
phytochems. or synthetic agents. Silibinin is a naturally occurring flavanone, isolated from milk thistle ext., and has been shown to
possess cancer prevention/intervention potential against various cancers. In several animal and human studies, it is found to be safe
and non-toxic. Human bladder transitional-cell papilloma RT4 cells were treated with silibinin and analyzed for survivin protein and
mRNA levels by Western blotting and real-time RT-PCR, resp. Silibinin treatment of cells for 24 h at 100 μM dose resulted in
.apprx.50% decrease in survivin protein level; however, treatment at 200 μM dose for 24 and 48 h showed a complete loss in survivin
protein without any change in actin used as loading control. Employing RT-PCR anal. we also obsd. that silibinin causes a strong to
complete decrease in survivin mRNA levels. In other studies, down-regulation of survivin by silibinin was assocd. with a very strong
and prominent caspases-9 and -3 activation as well as PARP cleavage. Quant. apoptotic assay showed that silibinin decreased
survivin levels and caspases-PARP cleavages, in accord with a strong apoptotic death and growth inhibition of RT4 cells. Together,
these findings suggest that more studies are needed to investigate in vivo effect of silibinin on survivin expression and assocd. biol.
effects in bladder cancer that could provide useful information for silibinin efficacy in the prevention/intervention of human bladder
cancer.
Answer 848:
Foliar flavonoids of the most primitive group, sect. Distegocarpus within the genus Carpinus. Chang, Chin-Sung; Jeon,
Jeong Ill. Department of Forest Resources and the Arboretum, Seoul National University, Suwon, S. Korea. Biochemical
Systematics and Ecology (2004), 32(1), 35-44. Publisher: Elsevier Science B.V., CODEN: BSECBU ISSN: 0305-1978. Journal
Abstract
flavanone
Foliar flavonoids in five taxa of the section Distegocarpus of Carpinus from China, Korea, and Japan were examd. Eleven compds.,
including monoglycosides of the flavonols myricetin, kaempferol and quercetin and the flavone luteolin along with hesperidin, were
isolated and identified. The flavonoid profiles were relatively simple, but showed distinct differentiation among taxa. Flavonoid chem.,
morphol. characteristics, and geog. distribution patterns were in accord with the idea that section Distegocarpus appeared to have
differentiated into two groups from the ancestor; one group (fangiana-type) consisting of C. fangiana and C. rankanensis, and the
other (japonica-type) consisting of C. cordata and C. japonica. C. japonica was considered as the most primitive extant species of the
section with respect to flavonoid compds. as well as morphol. characteristics. Within the fangiana-type, however, C. fangiana
represented a more advanced species than C. rankanensis only with respect to morphol. The fact that the presence of a flavanone,
which was a direct precursor to flavones and flavonols, was found in C. fangiana did not show correlation with the result of morphol.
advancement within the fangiana group.
Answer 849:
A rapid screening assay for inhibitors of 11β-hydroxysteroid dehydrogenases (11β-HSD): flavanone selectively inhibits
11β-HSD1 reductase activity. Schweizer, Roberto A. S.; Atanasov, Atanas G.; Frey, Brigitte M.; Odermatt, Alex. Division of
Nephrology and Hypertension, Department of Clinical Research, University of Berne, Bern, Switz. Molecular and Cellular
Endocrinology (2003), 212(1-2), 41-49. Publisher: Elsevier Science Ltd., CODEN: MCEND6 ISSN: 0303-7207. Journal written in
Abstract
A rapid screening assay for chems. inhibiting 11β-hydroxysteroid dehydrogenase (11β-HSD) type 1 or type 2 using lysates from
stably transfected cells was developed. Here, we tested a series of environmental chems. for anti-11β-HSD activities. Inhibition of
11β-HSD2, which may cause cortisol-dependent activation of the mineralocorticoid receptor with sodium retention and hypertension,
was obsd. for several compds., with diethylcarbamate being the most potent inhibitor (IC50 6.3 μM). Abietic acid inhibited both
11β-HSD1 (IC50 27 μM for redn. and 2.8 μM for oxidn.) and 11β-HSD2 (IC50 12 μM). Our results demonstrate for the first time that
flavanone selectively inhibits 11β-HSD1 reductase activity: this enzyme being considered as essential for the local activation of
glucocorticoids and representing a potential target for the therapeutic treatment of diabetes type 2. Flavanone and
2'-hydroxyflavanone efficiently inhibited reductive (IC50 18 and 10 μM) but not oxidative activity. We obsd. a reduced inhibitory
effect of hydroxylated flavanone derivs. and of flavones contg. a double-bond between atom C2 and C3. Flavanone was specific for
11β-HSD1 and did not inhibit 11β-HSD2. Our results reveal that a variety of environmental compds. exert distinct inhibitory effects on
11β-HSD1 and 11β-HSD2, opening the possibility for selectively modulating local cortisone/cortisol availability in vivo.
Answer 850:
Genotyping of strawberry by PCR. Matsumoto, Akira; Kuniji, Miyuki; Fukino, Nobuko. (Nogyo Gijutsu Kenkyu Kiko, Japan).
Jpn. Kokai Tokkyo Koho (2003), 14 pp. CODEN: JKXXAF JP 2003339399 A 20031202 Patent written in Japanese.
Application: JP 2002-155547 20020529. Priority: . CAN 139:393524 AN 2003:936311 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))

JP 2003339399 A 20031202 JP 2002-155547 20020529
flavanone
JP 2002-155547 20020529
Abstract
The DNA is extd. from calyx-contg. fruit and/or leaf of strawberry and analyzed by PCR for genotyping. The introns of the APX
(ascorbic acid peroxidase), chalcone synthase (CHI), and flavanone-3-hydroxylase (F3H) genes were amplified by PCR for
genotyping. Also used were strain-specific DNA markers such as APX insertion sequence.
Answer 851:
Characteristic Raman bands for Artocarpus heterophyllus heartwood. Yamauchi, Shigeru; Shibutani, Sakae; Doi, Shuichi.
Institute of Wood Technology, Akita Prefectural University, Noshiro, Japan. Journal of Wood Science (2003), 49(5), 466-468.
Publisher: Springer-Verlag Tokyo, CODEN: JWSCFG ISSN: 1435-0211. Journal written in English. CAN 141:107787 AN
Abstract
The Raman spectrum of Artocarpus heterophyllus heartwood, which proved to be a rich source of flavonoids, exhibited two
characteristic bands, at 1247cm-1 and 745cm-1. The bands also appeared in the Raman spectrum of the yellow-brown needles extd.
from the heartwood with methanol. Based on the Raman measurements of flavones and related compds., it was predicted that the
Raman band at 1247cm-1 may be attributed to flavonoid-type compds. No vibrational band corresponding to the characteristic Raman
bands was obsd. by diffuse reflectance IR spectroscopy. Thus, it was suggested that observation of the characteristic bands is an
advantage of Fourier transform-Raman spectroscopy for nondestructive anal. of wood.
Answer 852:
An easy access to spiroisoxazoline[5,31]flavan-41-one through 1,3-dipolar cycloaddition reaction of nitrile oxide to unusual
dipolarophiles. Manikandan, Santhanaraman; Jayashankaran, Jayadevan; Raghunathan, Raghavachary. Department of
Chemistry, University of North Carolina at Chapel Hill, NC, USA. Synthetic Communications (2003), 33(23), 4063-4069.
Publisher: Marcel Dekker, Inc., CODEN: SYNCAV ISSN: 0039-7911. Journal written in English. CAN 140:146042 AN
Abstract
Synthesis of a series of novel spiro[3,4-diaryl-4,5-dihydroisoxazole-5,31-flavan-41-one] I (R = H, Me, MeO, Cl, NO2; R1 = H, Cl) was
accomplished in good yields by the regioselective 1,3-dipolar cycloaddn. reaction of nitrile oxide to 3-arylmethylideneflavan-4-ones.
flavanone
R
O Ph
O
O N
R1 I
Answer 853:
Identification and biological activity of microbial metabolites of xanthohumol. Herath, Wimal; Ferreira, Daneel; Khan,
Shabana Iqrar; Khan, Ikhlas Ahmad. National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences,
The University of Mississippi, University, MS, USA. Chemical & Pharmaceutical Bulletin (2003), 51(11), 1237-1240. Publisher:
Pharmaceutical Society of Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN 140:196011 AN
Abstract
Microbial transformation of xanthohumol using the culture broth of Cunninghamella echinulata NRRL 3655 afforded
(2S)-8-[4''-hydroxy-3''-methyl-(2''-Z)-butenyl]-4',7-dihydroxy-5-methoxyflavanone (5) and
(2S)-8-[5''-hydroxy-3''-methyl-(2''-E)-butenyl]-4',7-dihydroxy-5-methoxyflavanone (6). Xanthohumol (1) and flavanone 6 as well as
(E)-2''-(2'''-hydroxyisopropyl)-dihydrofurano[2'',3'':4',3']-2',4-dihydroxy-6'-methoxychalcone (2),
(2S)-2''-(2'''-hydroxyisopropyl)-dihydrofurano[2'',3'':7,8]-4'-hydroxy-5-methoxyflavanone (3) obtained with Pichia membranifaciens
showed antimalarial activity against Plasmodium falciparum.
Answer 854:
Characterization of leachianone G 2''-dimethylallyltransferase, a novel prenyl side-chain elongation enzyme for the
formation of the lavandulyl group of sophoraflavanone G in Sophora flavescens Ait. cell suspension cultures. Zhao, Ping;
Inoue, Kenichiro; Kouno, Isao; Yamamoto, Hirobumi. Medicinal Plant Garden, Course of Pharmaceutical Sciences, Graduate School
of Biomedical Sciences, Nagasaki University, Nagasaki, Japan. Plant Physiology (2003), 133(3), 1306-1313. Publisher:
American Society of Plant Biologists, CODEN: PLPHAY ISSN: 0032-0889. Journal written in English. CAN 140:107355 AN
Abstract
Leachianone G (LG) 2''-dimethylallyltransferase, a novel prenyl side-chain elongation enzyme, was identified in Sophora flavescens
Ait. cultured cells. The enzyme transfers a dimethylallyl group to the 2'' position of another dimethylallyl group attached at position 8
of LG to form sophoraflavanone G, a branched monoterpenoid-conjugated flavanone characteristic to this plant. This membrane-bound
dimethylallyltransferase required Mg2+ (optimum concn. was 10 mM) for the reaction and had an optimum pH of 8.8. It utilized
dimethylallyl diphosphate as the sole prenyl donor, and the 2'-hydroxy function in LG was indispensable to the activity. The apparent
Km values for dimethylallyl diphosphate and LG were 59 and 2.3 μM, resp. Subcellular localization of three enzymes that participated
flavanone
in the formation of the lavandulyl group was also investigated by sucrose d. gradient centrifugation. Two prenyltransferases,
naringenin 8-dimethylallyltransferase and LG 2''-dimethylallyltransferase, were localized in the plastids, whereas
8-dimethylallylnaringenin 2'-hydroxylase, which catalyzes the crucial step in the lavandulyl-group formation, was assocd. with the
endoplasmic reticulum. These results suggest the close cooperation between the plastids and the endoplasmic reticulum in the
formation of lavandulyl groups.
Answer 855:
Comparative molecular field analysis (CoMFA) model using a large diverse set of natural, synthetic and environmental
chemicals for binding to the androgen receptor. Hong, H.; Fang, H.; Xie, Q.; Perkins, R.; Sheehan, D. M.; Tong, W. Northrop
Grumman Information Technol., Jefferson, AR, USA. SAR and QSAR in Environmental Research (2003), 14(5-6), 373-388.
Publisher: Taylor & Francis Ltd., CODEN: SQERED ISSN: 1062-936X. Journal written in English. CAN 140:265890 AN
Abstract
A large no. of natural, synthetic and environmental chems. are capable of disrupting the endocrine systems of exptl. animals, wildlife
and humans. These so-called endocrine disrupting chems. (EDCs), some mimic the functions of the endogenous androgens, have
become a concern to the public health. Androgens play an important role in many physiol. processes, including the development and
maintenance of male sexual characteristics. A common mechanism for androgen to produce both normal and adverse effects is
binding to the androgen receptor (AR). In this study, the authors used Comparative Mol. field Anal. (CoMFA), a 3D quant.
structure-activity relationship (3D-QSAR) technique, to examine AR-ligand binding affinities. A CoMFA model with r2=0.902 and
q2=0.571 was developed using a large training data set contg. 146 structurally diverse natural, synthetic, and environmental chems.
with a 106-fold range of relative binding affinity (RBA). By comparing the binding characteristics derived from the CoMFA contour
map with these obsd. in a human AR crystal structure, the authors found that the steric and electrostatic properties encoded in this
training data set are necessary and sufficient to describe the RBA of AR ligands. Finally, the CoMFA model was challenged with an
external test data set; the predicted results were close to the actual values with av. difference of 0.637 logRBA. This study
demonstrates the utility of this CoMFA model for real-world use in predicting the AR binding affinities of structurally diverse chems.
over a wide RBA range.
Answer 856:
Effect of prohexadione-Ca on various fruit crops: flavonoid composition and substrate specificity of their dihydroflavonol
4-reductases. Gosch, C.; Puhl, I.; Halbwirth, H.; Schlangen, K.; Roemmelt, S.; Andreotti, C.; Costa, G.; Fischer, T. C.; Treutter,
D.; Stich, K.; Forkmann, G. Chair of Floriculture Crops and Horticultural Plant Breeding, Department of Plant Sciences, Technical
University of Munich, Freising, Germany. European Journal of Horticultural Science (2003), 68(3), 144-151. Publisher: Verlag
Eugen Ulmer GmbH & Co., CODEN: EJHSAS ISSN: 1611-4426. Journal written in English. CAN 140:176691 AN 2003:904275
Abstract
In pome fruit trees, the growth retardant prohexadione-Ca induces the formation of 3-deoxycatechins, which correlates with an
increased resistance against fire blight and also against some fungal diseases. The formation of 3-deoxycatechins is due to the
channeling of intermediates unusual for pome fruits, which requires the presence of a flavanone 4-reductase (FNR) activity. Here, it
is investigated, whether the crop plants strawberry, grapevine, cranberry, cherry, peach, plum, elder, and kiwi fruit react in the same
way to prohexadione-Ca application. The presence of FNR activity is shown by enzymic investigations and the formation of a
3-deoxycatechin after prohexadione-Ca application in planta. Furthermore, by cloning of the corresponding cDNAs and studies with the
flavanone
heterologously expressed enzymes it is shown that the DFR enzymes of grapevine, cranberry and strawberry possess also FNR
activity. Conclusively, all the crop plants studied have the potential to form 3-deoxyflavonoids. However, the changes in the
flavonoid compn. obsd. after prohexadione-Ca treatment were not exactly the same in all species studied here. In kiwi fruit leaves, a
strong accumulation of flavanones rather than the formation of large amts. of 3-deoxycatechins is obsd.
Answer 857:
Can prohexadione-Ca induce antimicrobial flavonoids in rose? Schlangen, K.; Gosch, C.; Roemmelt, S.; Knott, J.; Fischer, T.
C.; Treutter, D.; Forkmann, G.; Stich, K.; Halbwirth, H. Institute of Technical BioScience, Technical University of Vienna, Vienna,
Austria. European Journal of Horticultural Science (2003), 68(3), 137-143. Publisher: Verlag Eugen Ulmer GmbH & Co., CODEN:
EJHSAS ISSN: 1611-4426. Journal written in English. CAN 140:178386 AN 2003:904273 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Rose (Rosa x bybrida), a popular and widely spread garden plant, is infected by numerous plant diseases, which are mainly caused by
fungal and even by bacterial pathogens such as Erwinia amylovora, the causal agent of fire blight. Recently, prohexadione-Ca, a
2-oxoglutarate specific inhibitor originally developed as a growth retardant, was reported to influence the flavonoid compn. of apple and
pear leaves and, thus, to increase resistance against fire blight and other diseases. It was supposed that this approach could also
mediate resistance in roses. As the first step, the induction of the antimicrobial 3-deoxyflavonoid in rose leaves after
prohexadione-Ca application was investigated in a time course expt. Due to the presence of disturbing phenolic compds. impeding the
prepn. and testing of enzymes, enzyme prepn. procedures and assays had to be adapted and optimized for rose leaves. Std. enzyme
assays are described for phenylalanine ammonia lyase (PAL), chalcone synthase/chalcone isomerase (CHS/CHI), flavanone
3-hydroxylase (FHT), dihydroflavonol 4-reductase (DFR) and flavanone 4-reductase (FNR). Cloning and heterologous expression
showed that the DFR of rose exhibits FNR activity as well. Treatment of rose leaves with prohexadione-Ca led to the inhibition of FHT
and to the formation of the 3-deoxyflavonoid luteoliflavan. Likewise, induction effects on PAL, CHS and DFR/FNR activity were also
obsd. In general, it could be shown that rose leaves produce 3-deoxyflavonoids after prohexadione-Ca treatment and, therefore, this
method can be considered as a potential protection strategy for roses that will be studied phytopathol. in a next step.
Answer 858:
Furoquinoline alkaloids from Teclea nobilis. Al-Rehaily, Adnan J.; Ahmad, Mohammad S.; Muhammad, Ilias; Al-Thukair, Assad
A.; Perzanowski, Herman P. College of Pharmacy, Department of Pharmacognosy, King Saud University, Riyadh, Saudi Arabia.
Phytochemistry (Elsevier) (2003), 64(8), 1405-1411. Publisher: Elsevier Science B.V., CODEN: PYTCAS ISSN: 0031-9422.
Abstract
Five new furoquinoline alkaloids, namely tecleabine (1), tecleoxine (2), isotecleoxine (3), methylnkolbisine (4) and chlorodesnkolbisine
(5) were isolated from the aerial parts of Teclea nobilis, together with seven known furoquinoline derivs.; one acridone alkaloid, and one
known flavanone. The structures of the alkaloids 1-5 were established by 1D and 2D NMR spectral data, including COSY, HMQC and
HMBC expts., as well as HRMS.
Answer 859:
flavanone
Prenylated flavonoids from Moghania philippinensis. Ahn, Eun-Mi; Nakamura, Norio; Akao, Teruaki; Komatsu, Katsuko; Qui,
Ming-Hua; Hattori, Massao. Institute of Natural Medicine, Toyama Medical and Pharmaceutical University, Toyama, Japan.
Phytochemistry (Elsevier) (2003), 64(8), 1389-1394. Publisher: Elsevier Science B.V., CODEN: PYTCAS ISSN: 0031-9422.
Abstract
Five prenylated flavonoids, 8-(1,1-dimethylallyl)genistein (1), 5,7,3',4'-tetrahydroxy-2',5'-di(3-methylbut-2-enyl)isoflavone (2),

5,7,3'-trihydroxy-2'-(3-methylbut-2-enyl)-4',5'-(3,3-dimethylpyrano)isoflavone (3),
(2R)-5,2',4'-trihydroxy-8,5'-di(3-methylbut-2-enyl)-6,7-(3,3-dimethylpyrano)flavanone (4a) and (2S)-5, 2',
4'-trihydroxy-8,5'-di(3-methylbut-2-enyl)-6,7-(3,3-dimethylpyrano)flavanone (4b), were isolated from the roots of Moghania
philippinensis. The structures of these compds. were detd. on the basis of spectroscopic and chem. means.
Answer 860:
Secondary metabolites from the liverwort Tylimanthus renifolius. Feld, Hildegard; Zapp, Josef; Becker, Hans.
Pharmakognosie und Analytische Phytochemie, FR 8.7, Universitat des Saarlandes, Saarbrucken, Germany. Phytochemistry
(Elsevier) (2003), 64(8), 1335-1340. Publisher: Elsevier Science B.V., CODEN: PYTCAS ISSN: 0031-9422. Journal written in
Abstract
Two new herbertane sesquiterpenoids, (-)-herbertene-1,12-diol and (-)-γ-herbertenol, a new aromadendrane,

9-acetoxy-10-hydroxyaromadendrane, a new rosane diterpenoid, 5,15-rosadiene-3,11-dione and a new phytane,
2Z-phytene-1,15,20-triol, along with the known (-)-α-herbertenol have been isolated from the liverwort Tylimanthus renifolius. Several
flavones and flavanones with an unsubstituted ring B were also identified. This is the first report of this class of flavonoids from the
Hepaticae. All structures were elucidated by NMR spectroscopy.
Answer 861:
Use of 8-prenylflavanones for anti-angiogenesis therapy and for fibrinolytic therapy. Schleuning, Wolf-Dieter; Pepper,
Michael. (Schering Aktiengesellschaft, Germany). Eur. Pat. Appl. (2003), 21 pp. CODEN: EPXXDW EP 1360959 A1 20031112
Designated States R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT, IE, SI, LT, LV, FI, RO, MK, CY, AL, TR.
Patent written in English. Application: EP 2002-90170 20020510. Priority: . CAN 139:364765 AN 2003:891962 CAPLUS

EP 1360959 A1 20031112 EP 2002-90170 20020510
TR
AU 2003218721 A1 20031111 AU 2003-218721 20030310
WO 2003094910 A1 20031120 WO 2003-EP2445 20030310
flavanone
BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IT, LU, MC, NL, PT, SE, SI, SK, TR, BF,
BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG
EP 1503752 A1 20050209 EP 2003-711961 20030310
JP 2005526122 T 20050902 JP 2004-502996 20030310
EP 2002-90170 A 20020510
WO 2003-EP2445 W 20030310
Abstract
The present invention provides the use of 8-prenylflavanones such as I: wherein R1 = H, a OH group in position 2', 3' or 4'; a OMe
group in position 2', 3' or 4' or a OEt group in position 3' or 4'; R2 = H, a OH group in position 3', 4', 5' or 6'; a OMe group in position 3'
or 4' or a OEt group in position 5'; R3 = H, a OH group in position 4', 5' or 6' or a OMe group in position 4', 5' or 6'; R4 = H, OH; for the
prepn. of a pharmaceutical compn. for the treatment or prevention of angiogenesis-related diseases and for the treatment or
prevention of thrombotic disorders. Thus, (±)-8-prenylnaringenin (II) inhibits in vitro angiogenesis induced by bFGF, VEGF or a
combination of bFGF and VEGF, in a dose-dependent manner. A quant. anal. revealed that II inhibited BME cell invasion with an IC50
of between 3-10μM, irresp. of the angiogenic stimulus.
Me Me Me Me
R1 R2
OH
R3
HO O HO O
R4
OH O I OH O II
Answer 862:
Polymer-bound cellulose phenylcarbamate derivatives as chiral stationary phases for enantioselective HPLC. Ling, Frank;
Brahmachary, Enugurthi; Xu, Mingcheng; Svec, Frantisek; Frechet, Jean M. J. Department of Chemistry, University of California,
Berkeley, CA, USA. Journal of Separation Science (2003), 26(15-16), 1337-1346. Publisher: Wiley-VCH Verlag GmbH & Co.
KGaA, CODEN: JSSCCJ ISSN: 1615-9306. Journal written in English. CAN 140:174062 AN 2003:882197 CAPLUS
flavanone
Abstract
Novel chiral stationary phases (CSP) were prepd. by coating the internal surface of monodisperse macroporous poly(2-aminoethyl
methacrylate-co-ethylene dimethacrylate) beads with dimethylphenylcarbamate derivs. of regenerated cellulose. The coating was
achieved either by simple adsorption or by chem. bonding using a diisocyanate linker. Sepn. of enantiomers in normal-phase HPLC
mode was used to evaluate the enantioselectivity of all CSPs. The influence of the properties of the polymer support such as pore
size, pore vol., and content of the amine functionalities, reaction and sepn. conditions such as wt. ratio of modified cellulose selector
to polymer beads, amt. of diisocyanate crosslinker, and the compn. of the mobile phase on chiral discrimination and chromatog.
resoln. were also systematically studied. The CSPs prepd. by chem. anchoring were more stable and a wider range of solvents
including dichloromethane could be used for the sepns. Compared to the coated-type CSPs, the chem. bonded stationary phases
enabled the enantiosepns. of a larger no. of racemates and exhibited enantioselectivity fully comparable to their counterparts prepd.
using porous silica as a support. However, the benefits of tailored macroporous polymer supports demonstrated earlier with brush-type
CSPs did not enhance the performance of the chiral stationary phases prepd. from cellulose-based selectors.
Answer 863:
Cloning and characterization of a glucosyltransferase that reacts on 7-hydroxyl group of flavonol and 3-hydroxyl group of
coumarin from tobacco cells. Taguchi, Goro; Ubukata, Takahisa; Hayashida, Nobuaki; Yamamoto, Hirobumi; Okazaki, Mitsuo.
Research Center for Human and Environmental Sciences, Division of Gene Research, Shinshu University, 3-15-1 Tokida, Ueda,
Japan. Archives of Biochemistry and Biophysics (2003), 420(1), 95-102. Publisher: Elsevier Science, CODEN: ABBIA4 ISSN:
Abstract
In higher plants, secondary metabolites are often converted to their glycoconjugates by glycosyltransferases (GTases). We cloned a
cDNA encoding GTase (NtGT2) from tobacco (Nicotiana tabacum L.). The recombinant enzyme expressed in Escherichia coli (rNTGT2)
showed glucosylation activity against several kinds of phenolic compds., particularly the 7-hydroxyl group of flavonoids and
3-hydroxycoumarin. The Km values of kaempferol and 3-hydroxycoumarin with rNTGT2 are 6.5 μM and 23.6 μM, resp. The deduced
amino acid sequence of NTGT2 shows 60-70% identity to that of anthocyanin 5-O-glucosyltransferase (A5GT); rNTGT2 did not show
activity against the anthocyanins tested. NtGT2 gene expression was induced by treating tobacco cells with plant hormones such as
salicylic acid. We consider that NtGT2 gene might have evolved from the same ancestral gene as the A5GT genes to the
stress-inducible GTases that react on several phenolic compds.
Answer 864:
Citrus limon: a source of flavonoids of pharmaceutical interest. Del Rio, J. A.; Fuster, M. D.; Gomez, P.; Porras, I.;
Garcia-Lidon, A.; Ortuno, A. Facultad de Biologia, Departamento de Biologia Vegetal, Universidad de Murcia, Murcia, Spain. Food
Chemistry (2003), Volume Date 2004, 84(3), 457-461. Publisher: Elsevier Science, CODEN: FOCHDJ ISSN: 0308-8146. Journal
Abstract
Some of the medicinal properties of lemons are due to the flavonoids they contain since they are involved in many biol. activities and
have many health-related functions. The levels of the principal flavanones and flavone found in different cultivars of Citrus limon,
are analyzed in an attempt to identify the most interesting as regards the content of such secondary compds. The results show that
the immature fruits from cultivars Lisbon and Fino-49 are ideal for obtaining the flavanone hesperidin, while the mature fruits of
flavanone
cultivar Fino-49 and the leaves of cultivar Eureka are the most interesting for obtaining the flavone diosmin and the flavanone
eriocitrin.
Answer 865:
High-performance liquid chromatographic enantioseparation using chitin carbamate derivatives as chiral stationary phases.
Yamamoto, Chiyo; Hayashi, Tomoko; Okamoto, Yoshio. Graduate School of Engineering, Department of Applied Chemistry,
Nagoya University, Chikusa-ku, Nagoya, Japan. Journal of Chromatography, A (2003), 1021(1-2), 83-91. Publisher: Elsevier
Science B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. CAN 140:191761 AN 2003:869869 CAPLUS
Abstract
Chitin carbamate derivs. including 4-substituted and 3,5-disubstituted phenylcarbamates, 1-phenylethylcarbamates, and
cycloalkylcarbamates were synthesized and coated on macroporous silica gel to evaluate their chiral recognition abilities as chiral
stationary phases (CSPs) for HPLC. Among the derivs., the 3,5-dimethylphenyl, 4-chlorophenyl, and
4-trifluoromethylphenylcarbamates showed relatively high-chiral recognition abilities when a hexane-2-propanol mixt. was used as the
eluent. The CSPs based on the chitin 3,5-dimethylphenyl and 3,5-dichlorophenylcarbamates could be stably used in the presence of
chloroform and Et acetate as a component of the eluents, and a few racemates were more sufficiently resolved by the addn. of a
small amt. of chloroform in the mobile phase. Some racemates were more efficiently resolved under the reversed phase condition.
Answer 866:
Chalcones, coumarins, and flavanones from the exudate of Angelica keiskei and their chemopreventive effects. Akihisa,
Toshihiro; Tokuda, Harukuni; Ukiya, Motohiko; Iizuka, Masao; Schneider, Stefan; Ogasawara, Kazuya; Mukainaka, Teruo; Iwatsuki,
Kenji; Suzuki, Takashi; Nishino, Hoyoku. College of Science and Technology, Nihon University, 1-8 Kanda Surugadai, Chiyoda-ku,
Tokyo, Japan. Cancer Letters (Oxford, United Kingdom) (2003), 201(2), 133-137. Publisher: Elsevier, CODEN: CALEDQ ISSN:
Abstract
From an Et acetate-sol. fraction of the exudate obtained from the stems of Angelica keiskei (Umbelliferae), 17 compds., viz. five
chalcones (1-5), seven coumarins (6-12), three flavanones (13-15), one diacetylene (16), and one 5-alkylresorcinol (17), were isolated.
These compds. were evaluated with respect to their inhibitory effects on the induction of Epstein-Barr virus early antigen (EBV-EA) by
12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, which is known to be a primary screening test for antitumor-promoters. With
the exception of three compds. (10, 16, and 17), all other compds. tested showed potent inhibitory effects on EBV-EA induction
(92-100% inhibition at 1×103 mol ratio/TPA). In addn., upon evaluation of these compds. for the inhibitory effects against activation of
(±)-(E)-methyl-2-[(E)-hydroxy-imino]-5-nitro-6-methoxy-3-hexemide (NOR 1), a nitric oxide (NO) donor, as a primary screening test for
antitumor-initiators, two chalcones (2 and 3) and six coumarins (6-11) exhibited potent inhibitory effects.
Answer 867:
Being acyanic: An unavoidable fate for many white flowers? Seitz, C.; Oswald, N.; Boerstling, D.; Forkmann, G.; Martens, S.
Department fuer Pflanzenwissenschaften, Lehrstuhl fuer Zierpflanzenbau, TU Muenchen, Freising, Germany. Acta Horticulturae
flavanone
(2003), 612 83-88. Publisher: International Society for Horticultural Science, CODEN: AHORA2 ISSN: 0567-7572. Journal written
Abstract
For a range of white flowering ornamental species possessing favorable phenotypical and economical properties, there is an ardent
desire of breeders to get them colored. Unfortunately, classical approaches often fail in this respect which has led to an increased
interest in understanding the underlying reasons for this failure. Here, attention is focused on flavonoids as the main group of
color-giving compds. in flowers. Flavonoid biosynthesis is a well-examd. pathway. In particular, it has been possible to demonstrate
and characterize the activity of flavonoid enzymes resulting in the formation of anthocyanins, which are responsible for colors ranging
from orange and red to lilac and blue. The lack of activity of one or more enzymes of this pathway leads to acyanic flowers. In white
spatha of Zantedeschia aethiopica cv. 'Nili' and white petals of Osteospermum-Hybrid cv. 'Zimba' early enzymes of flavonoid
biosynthesis chalcone synthase (CHS), chalcone isomerase (CHI) and flavanone 3-hydroxylase (FHT) were proven to be active,
resulting in the formation of dihydrokaempferol (DHK). This compd. was shown to be 3'-hydroxylated to dihydroquercetin (DHQ) by
flavonoid 3'-hydroxylase (F3'H) in Zantedeschia and to be 3'- and 5'-hydroxylated to DHQ and dihydromyrecetin (DHM) by flavonoid
3'5'-hydroxylase (F3'5'H) in Osteospermum. Whereas redn. of dihydroflavonols by DFR to leucoanthocyanidins did not occur in
'Zimba', it was clearly detected in 'Nili'. This suggests a lack of anthocyanidin synthase (ANS) activity in 'Nili'. ANS converts
leucoanthocyanidins to resp. anthocyanidins. Particle gun bombardment of 'Nili' spatha with plasmids contg. Ans from M. incana led to
red spots, thus supporting this hypothesis. On the other hand, 'Zimba' petals did not show any spotting under bombardment both with
plasmids contg. Ans and plasmids contg. Dfr from Gerbera-Hydrids suggesting the regulatory blocking of a complete set of late
enzymes.
Answer 868:
Preparation of novel flavanoids as chemotherapeutic, chemopreventive, and antiangiogenic agents. Zaveri, Nurulain; Chao,
Wan-Ru. (SRI International, USA; Stanford Research Institute International). PCT Int. Appl. (2003), 72 pp. CODEN: PIXXD2
WO 2003089423 A2 20031030 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN, CO,
CR, CU, CZ, DE, DK, DM, DZ, EC, EE, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR,
LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NI, NO, NZ, OM, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, TJ, TM, TN,
TR, TT, TZ, UA, UG, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT,
LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO
2003-US12658 20030418. Priority: US 2002-126407 20020418. CAN 139:350577 AN 2003:855920 CAPLUS (Copyright (C)

WO 2003089423 A2 20031030 WO 2003-US12658 20030418
WO 2003089423 A3 20040219
SG, SK, SL, TJ, TM, TN, TR, TT, TZ, UA, UG, UZ, VC, VN, YU, ZA, ZM, ZW
US 20030229136 A1 20031211 US 2002-126407 20020418
CA 2484080 A1 20031030 CA 2003-2484080 20030418
flavanone
AU 2003231069 A1 20031103 AU 2003-231069 20030418

EP 1495014 A2 20050112 EP 2003-724194 20030418
JP 2005533760 T 20051110 JP 2003-586144 20030418
US 2002-126407 A 20020418
WO 2003-US12658 W 20030418
Abstract
Novel compds. useful as chemotherapeutic, chemopreventive, and antiangiogenic agents are provided. The compds. are flavanoids,
including flavanones, flavanols, and chalcones. The compds. I [R1 - R3 = OH, halo, SH, alkoxy, aryloxy, aralkoxy; R1R2 = cycle;
R2R3 = cycle; α, β and γ = optional bonds, (providing that when α is absent, β is present, and when β is absent, α is present; when α
is present, preferred R4 moieties are selected from O, S, NH and CH2, and when γ is absent, preferred R4 groups are selected from
OH, SH, NH2 and CH3; when γ is present, the preferred R5 substituent is O, while when γ is absent, the preferred R5 substituent is
OH);R6 - R9 = H, alkyl, alkenyl, aryl, aralkyl, alkoxy, aryloxy, aralkoxy (providing that R6 and R7, R7 and R8 or R8 and R9 = maybe
linked to form a 5- or 6-membered ring and fused 5- and/or 6-membered rings, the rings being arom., alicyclic, heteroarom.,
heteroalicyclic with 0 - 4 non-hydrogen atoms and 0 - 3 heteroatoms); R10, R11 = H, OH, alkyl, alkoxy, halo]. Thus, SR 13179 (II)
was prepd. from 2-acetyl-α-naphthol and 3,4,5-trimethoxybenzaldehyde in EtOH contg. piperidine and pyridine, followed by redn. with
NaBH4 in THF/EtOH.. Pharmaceutical compns. are provided as well as are methods of synthesis and use. The antiangiogenic
activity of SR 13179 (II) was tested vs. human vascular endothelial cells [IC50 = 1.41 mM vs. MCF-7 cells and IC50 = 3.01 mM vs.
MDA-MB-231 cells].
flavanone
R1
R 10 R2
R9
R8 R4 α
R3
β
R 11
R7 γ
R6 R5
I
OMe
OMe
O
OMe
OH
II
Answer 869:
Synthesis and characterization of 4-aroyl substituted pyrazolines and pyrazoles. Bodkhe, Pravin S.; Patil, K. N.; Doshi, A. G.
Department of Chemistry, Vidyabharti Mahavidyalaya, Amravati, India. Asian Journal of Chemistry (2003), 15(3 & 4),
1853-1855. Publisher: Asian Journal of Chemistry, CODEN: AJCHEW ISSN: 0970-7077. Journal written in English. CAN
Abstract
Some new 4-aroyl substituted pyrazolines and pyrazoles were synthesized by condensation of Ph hydrazine hydrochloride with 3-aroyl
flavanones in DMF contg. small amt. of piperidine. Also, 4-aroyl-substituted pyrazoles were synthesized by reaction with
4-aroyl-substituted pyrazolines with DMSO-I2-H2SO4 system or DMSO-I2 system. Structures of the compds. were characterized by
IR spectra, PMR spectra and chem. properties.
Answer 870:
Synthesis and antimicrobial study of some new chloro-substituted 4-aroyl isoxazolines. Parhate, Vandana V.; Maurya, M.
R.; Rajput, P. R.; Wagh, P. P.; Rai, M. K. Department of Chemistry, Vidya Bharti Mahavidyalaya, Amravati, India. Asian
Journal of Chemistry (2003), 15(3 & 4), 1825-1827. Publisher: Asian Journal of Chemistry, CODEN: AJCHEW ISSN: 0970-7077.
flavanone
Abstract
Some new chloro-substituted 4-aroyl isoxalines were synthesized by the interaction of chloro-substituted 3-aroyl flavanones with
NH2OH⋅HCl in DMSO contg. a few drops of piperidine. The structural assignments of these compds. are based on their elemental
anal., chem. properties and spectral data. The newly synthesized chloro-substituted 4-aroyl isoxazolines were evaluated for their
antimicrobial activity against E. coli, S. aureus, P. aeruginosa, P. vulgaris by disk diffusion method. The antibacterial results obtained
are very encouraging.
Answer 871:
Field survey of Glycyrrhiza plants in central Asia (2). Characterization of phenolics and their variation in the leaves of
Glycyrrhiza plants collected in Kazakhstan. Hayashi, Hiroaki; Zhang, Shui-Li; Nakaizumi, Tomoko; Shimura, Kumiko;
Yamaguchi, Misako; Inoue, Kenichiro; Sarsenbaev, Kanat; Ito, Michiho; Honda, Gisho. Gifu Pharmaceutical University, Gifu,
on SciFinder (R))
Abstract
A new prenylated flavanone, licoleafol, and a new prenylated dihydrostilbene, uralstilbene, together with four known compds.,
8-dimethylallyleriodictyol, sophoraflavanone B, gancaonin R, and 6-dimethylallyleriodictyol, were isolated from the leaves of
Glycyrrhiza uralensis collected in Kazakhstan. HPLC anal. of the leaves of Glycyrrhiza plants collected in Kazakhstan showed that
both G. uralensis-specific and Glycyrrhiza glabra-specific compds. were detected in the leaves of the morphol. intermediate-type
plants, suggesting that the intermediate-type plant is a hybrid of G. glabra and G. uralensis. In addn., HPLC profiles of leaf exts. from
offspring of intermediate-type plants were divided into the three types:the G. uralensis type, G. glabra type, and the intermediate type.
From these results, it appears likely that the intermediate-type plant back-crosses with G. glabra and G. uralensis to generate a G.
glabra-type plant and a G. uralensis-type plant, resp.
Answer 872:
Three diterpenoids (excoecarins V1-V3) and a flavanone glycoside from the fresh stem of Excoecaria agallocha. Konishi,
Tenji; Yamazoe, Kiyonori; Kanzato, Masahiro; Konoshima, Takao; Fujiwara, Yasuhiro. Kyoto Pharmaceutical University, Kyoto,
on SciFinder (R))
Abstract
Three new diterpenoids, excoecarins V1-V3 and a new flavanone glycoside were isolated from the fresh stem of Excoecaria agallocha
L. Their structures were elucidated as: 2α,3α,18-trihydroxy-3β,20-epoxybeyer-15-ene, ent-2,3-secokaur-16-en-2,3-dioic acid,
ent-3,4-seco-16α-hydroxyatis-4(19)-en-3-oic acid, and 3,5,7,3',5'-pentahydroxy-2R,3R-flavanonol 3-O-α-L-rhamnopyranoside on the
basis of spectroscopic data, chem. evidence, and/or X-ray anal.
Answer 873:
flavanone
Inhibitory effects of plant-derived flavonoids and phenolic acids on malonaldehyde formation from ethyl arachidonate.
Lee, Kwang-Geun; Shibamoto, Takayuki; Takeoka, Gary R.; Lee, Sung-Eun; Kim, Jeong-Han; Park, Byeoung-Soo. Department of
Food Science and Technology, Dongguk University, Seoul, S. Korea. Journal of Agricultural and Food Chemistry (2003), 51(24),
Abstract
The antioxidant activities of naturally occurring plant compds. were measured in a lipid peroxidn. system consisting of Et arachidonate
and Fenton's reagent. Inhibitory effects of 24 plant-derived flavonoids and 5 phenolic acids on malonaldehyde (MA) formation from Et
arachidonate were examd. using gas chromatog. (GC) with a nitrogen-phosphorus detector (NPD). Luteolin, which showed the strongest
antioxidant activity, inhibited MA formation by 94% and 97% at the levels of 0.5 and 1.0 mM, resp. The antioxidant activities of the
flavones and flavonols decreased in the following order: luteolin > rhamnetin > fisetin > kaempferol > morin > quercetin. Among the
flavanones tested, hesperitin, taxifolin, and naringenin exhibited appreciable antioxidant activities (61-84%) at the 1.0 mM level. The
inhibitory effect of epigallocatechin gallate (82.5% at the 1.0 mM level) was the strongest among the flavan-3-ols tested. Ferulic acid
had the most potent antioxidant activity (74.6% at the 1.0 mM level) of the phenolic acids tested.
Answer 874:
Changes of flavonoids, vitamin C and antioxidant capacity in minimally processed citrus segments and juices during
storage. Del Caro, Alessandra; Piga, Antonio; Vacca, Vincenzo; Agabbio, Mario. Dipartimento di Scienze Ambientali Agrarie e
Biotecnologie Agro-Alimentari, Universita degli Studi, Sassari, Italy. Food Chemistry (2003), Volume Date 2004, 84(1), 99-105.
Publisher: Elsevier Science, CODEN: FOCHDJ ISSN: 0308-8146. Journal written in English. CAN 140:127375 AN 2003:820808
Abstract
Citrus fruits of different species and cultivars, ("Red blush" grapefruit, "Palazzelli" mandarin-type fruit, "Minneola" tangelo and
"Salustiana" and "Shamouti" orange) were minimally processed as segments or juices and cold-stored for up to 12 or 15 days, resp.
The flavanone glycosides, ascorbic acid (AA) content and antioxidant capacity were detd. during storage. Minimal processing had
almost no effect on the main chem. constituents, but ascorbic acid decreased significantly in "Minneola" and "Salustiana" segments,
with values ranging from 1.63 to 5.10 mg/g of dry matter, although only in the last samples taken. One of 3 juices (Salustiana) also
showed a decrease in AA content. The segments and juices showed different behavior during storage with regard to the flavonoid
content, which ranged from 0.77 mg to 8.32 mg/g dry matter in Palazzelli mandarin and Red blush grapefruit, resp. A significant
increase in total flavonoids (mainly hesperidin) was found in the segments, while the juices showed a diminution in flavonoid content.
Antioxidant capacity increased significantly in "Red blush" grapefruit juices and "Salustiana" orange segments, decreased in
"Salustiana" juices and "Minneola" tangelo segments and remained const. in the other samples. The antioxidant capacity, moreover,
was clearly correlated (r=0.968 and r=0.889 in segments and juices, resp.) with the ascorbic acid content rather than with the presence
of flavanone glycosides.
Answer 875:
Diterpenes and sesquiterpenes from the bark of Taxus yunnanensis. Nguyen, Nhan Trung; Banskota, Arjun H.; Tezuka,
flavanone
Yasuhiro; Nobukawa, Takahiro; Kadota, Shigetoshi. Institute of Natural Medicine, Toyama Medical and Pharmaceutical University,
Toyama, Japan. Phytochemistry (Elsevier) (2003), 64(6), 1141-1147. Publisher: Elsevier Science B.V., CODEN: PYTCAS
(R))
Abstract
Two taxane-type diterpenes, 10β-acetoxy-2α,5α,7β,9α-tetrahydroxytaxa-4(20),11-dien-13-one and

2α-acetoxy-9α-benzoyloxy-5α,7β,10β,15-tetrahydroxy-11(15 1)- abeotaxa-4(20),11-dien-13-one, and two new drimane-type
sesquiterpenes, 1β-acetoxy-7-drimen-11α-ol-12,11-lactone and 1β-acetoxy-11,12-epoxy-6-drimen-8α,11α-diol, were isolated from the
bark of Taxus yunnanensis together with 35 known taxane-type diterpenes, a known drimane-type sesquiterpene and a known
flavanone.
Answer 876:
A flavanone and a dihydrodibenzoxepin from Bauhinia variegata. Reddy, Mopuru V. B.; Reddy, Muntha K.; Gunasekar,
Duvvuru; Caux, Cristelle; Bodo, Bernard. Department of Chemistry, Natural Products Division, Sri Venkateswara University,
Tirupati, India. Phytochemistry (Elsevier) (2003), 64(4), 879-882. Publisher: Elsevier Science B.V., CODEN: PYTCAS ISSN:
Abstract
Phytochem. anal. of the root bark of Bauhinia variegata Linn yielded a new flavanone,
(2S)-5,7-dimethoxy-3',4'-methylenedioxyflavanone (1) and a new dihydrodibenzoxepin,
5,6-dihydro-1,7-dihydroxy-3,4-dimethoxy-2-methyldibenz [b,f]oxepin (2) together with three known flavonoids (3-5). The structures of
the new compds. were detd. on the basis of spectral studies.
Answer 877:
Exogenous ethylene stimulates the long-term expression of genes related to anthocyanin biosynthesis in grape berries.
El-Kereamy, Ashraf; Chervin, Christian; Roustan, Jean-Paul; Cheynier, Veronique; Souquet, Jean-Marc; Moutounet, Michel; Raynal,
Jose; Ford, Christopher; Latche, Alain; Pech, Jean-Claude; Bouzayen, Mondher. UMR 990, Genomique et Biotechnologie des Fruits,
INRA-INP/ENSA Toulouse, Castanet, Fr. Physiologia Plantarum (2003), 119(2), 175-182. Publisher: Blackwell Publishing Ltd.,
CODEN: PHPLAI ISSN: 0031-9317. Journal written in English. CAN 140:108179 AN 2003:788233 CAPLUS (Copyright (C)
Abstract
The treatment of grape berries (Vitis vinifera L. cv. Cabernet Sauvignon) with the ethylene-releasing compd., 2-chloroethylphosphonic
acid (2-CEPA), at veraison is a method known to enhance grape skin color. We obsd. that it produced a 6-fold increase, up to 30 pmol
g-1 FW, of the cluster internal ethylene compared to untreated controls within the 24 h following treatment. This ethylene upsurge was
assocd. with increased levels of chalcone synthase (CHS) and flavanone 3-hydroxylase (F3H) transcripts, which persisted over the
following 20 days. Transcript levels of leucoanthocyanidin dioxygenase (LDOX) and UDP glucose-flavonoid 3-O-glucosyl transferase
(UFGT) were similarly enhanced by 2-CEPA, although to a lesser extent. The effect on UFGT was confirmed at the protein level by an
immunoblot anal. The transcript accumulation of dihydroflavonol 4-reductase (DFR) was unaffected by 2-CEPA treatment. Examn. of
the levels of CHS, F3H and UFGT mRNAs in berries during bunch exposure to ethylene, revealed elevated levels of each transcript
flavanone
within the first 6 h of treatment when compared to nonethylene-treated controls. HPLC analyses of berry skin exts. showed that
levels of each of the anthocyanins analyzed (delphinidin, cyanidin, petunidin, peonidin and malvidin) increased over the 10 days
following the ethylene burst, and decreased thereafter. However, anthocyanin levels at harvest were still higher in ethylene treated
grapes than in controls. This data is the first evidence that ethylene triggers gene expression related to anthocyanin synthesis in
grapes, and in addn., our results also confirm the existence of other regulatory modes in the anthocyanin biosynthetic pathway.
Answer 878:
Chiral HPLC separation and CD spectra of the C-2 diastereomers of naringin in grapefruit during maturation. Caccamese,
Salvatore; Manna, Luigi; Scivoli, Giovanna. Dipartimento di Scienze Chimiche, Universita di Catania, Catania, Italy. Chirality
(2003), 15(8), 661-667. Publisher: Wiley-Liss, Inc., CODEN: CHRLEP ISSN: 0899-0042. Journal written in English. CAN
Abstract
Naringin is the chief flavanone glycoside of grapefruit (Citrus paradisi). It is responsible for part of the bitter taste of the fruit and can
cause the inhibition of some cytochrome P450s. The direct sepn. of (2R)- and (2S)-naringin in the albedo of grapefruits was obtained
in normal phase HPLC mode using Chiralcel OD as chiral stationary phase and n-hexane/ethanol with 0.1% of TFA as mobile phase.
Chiralpak AD was almost ineffective in the sepn. This procedure was used to evaluate the stereochem. at C-2 during maturation of
the grapefruit. The CD curves of (2R)- and (2S)-naringin isolated by semipreparative chiral HPLC were detd. and the elution order of
the chromatog. peaks was related to the abs. C-2 configuration. Partial resoln. of the C-2 diastereomers of narirutin was obtained on
Chiralpak AD.
Answer 879:
Prenylated flavanones isolated from flowers of Azadirachta indica (the neem tree) as antimutagenic constituents against
heterocyclic amines. Nakahara, Kazuhiko; Roy, Molay Kumar; Ono, Hiroshi; Maeda, Ikuko; Ohnishi-Kameyama, Mayumi; Yoshida,
Mitsuru; Trakoontivakorn, Gassinee. Japan International Research Center for Agricultural Sciences (JIRCAS), Tsukuba, Ibaraki,
Japan. Journal of Agricultural and Food Chemistry (2003), 51(22), 6456-6460. Publisher: American Chemical Society, CODEN:
JAFCAU ISSN: 0021-8561. Journal written in English. CAN 139:377970 AN 2003:761583 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Four prenylated flavanones were isolated from the methanol ext. of the flowers of Azadirachta indica (neem tree) as potent
antimutagens against Trp-P-1 (3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole) in the Salmonella typhimurium TA98 assay by
activity-guided fractionation. Spectroscopic properties revealed that these compds. were 5,7,4'-trihydroxy-8-prenylflavanone (I),
5,4'-dihydroxy-7-methoxy-8-prenylflavanone (II), 5,7,4'-trihydroxy-3',8-diprenylflavanone (III), and
5,7,4'-trihydroxy-3',5'-diprenylflavanone (IV). All isolated compds. were found for the first time in this plant. The antimutagenic IC50
values of compds. I-IV were 2.7 ± 0.1, 3.7 ± 0.1, 11.1 ± 0.1, and 18.6 ± 0.1 μM in the preincubation mixt., resp. These compds. also
similarly inhibited the mutagenicity of Trp-P-2 (3-amino-1-methyl-5H-pyrido[4,3-b]indole) and PhIP
(2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine). Compds. I-IV strongly inhibited ethoxyresorufin O-dealkylation activity of
cytochrome P 450 1A isoforms, which catalyze N-hydroxylation of heterocyclic amines. However, compds. I-IV did not show
significant inhibition against the direct-acting mutagen NaN3. Thus, the antimutagenic effect of compds. I-IV would be mainly based
on the inhibition of the enzymic activation of heterocyclic amines.
Answer 880:
flavanone
Hesperetin glucuronide, a photoprotective agent arising from flavonoid metabolism in human skin fibroblasts.
Proteggente, Anna R.; Basu-Modak, Sharmila; Kuhnle, Gunter; Gordon, Matthew J.; Youdim, Kuresh; Tyrrell, Rex; Rice-Evans,
Catherine A. Antioxidant Research Group, Wolfson Centre for Age-Related Diseases, GKT School of Biomedical Sciences, King's
College London, London, UK. Photochemistry and Photobiology (2003), 78(3), 256-261. Publisher: American Society for
Photobiology, CODEN: PHCBAP ISSN: 0031-8655. Journal written in English. CAN 140:249272 AN 2003:749311 CAPLUS
Abstract
There is considerable interest in the biol. properties of flavonoids in terms of their antioxidant and cytoprotective actions. The
interaction of the flavanone hesperetin with human skin fibroblasts (FEK4) has revealed the potential for metab. to hesperetin
glucuronide and its subsequent extrusion. As a consequence of this observation, the effectiveness of hesperetin glucuronides, in
comparison with that of the aglycon form, in protecting against UV-A radiation has been investigated. The results indicate that
hesperetin glucuronides, but not hesperetin, protect against UV-A-induced necrotic cell death.
Answer 881:
A novel biflavonoid from roots of Glycyrrhiza uralensis cultivated in China. Bai, Hong; Li, Wei; Koike, Kazuo; Dou, Deqiang;
Pei, Yuping; Chen, Yingjie; Nikaido, Tamotsu. School of Chinese Traditional Medicine, Shenyang Pharmaceutical University,
Shenyang, Peop. Rep. China. Chemical & Pharmaceutical Bulletin (2003), 51(9), 1095-1097. Publisher: Pharmaceutical Society of
Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN 140:56448 AN 2003:745724 CAPLUS (Copyright
Abstract
A novel biflavonoid named licobichalcone (I) was isolated from the roots of Glycyrrhiza uralensis cultivated in China, along with twelve
known compds., including five chalcones, two isoflavones, two flavanones, two flavones and one pterocarpan. The structures were
elucidated on the basis of chem. and spectroscopic evidence.
flavanone
OH
CO OH
HO CO OH
OMe
OMe
OH
OH I
Answer 882:
Chemical constituents of the flowers of Azadirachta indica. Siddiqui, Bina S.; Ali, Syed Tariq; Rasheed, Munawwer; Kardar,
Muhammad Nadeem. H.E.J. Research Institute of Chemistry, International Centre for Chemical Sciences, University of Karachi,
Karachi, Pak. Helvetica Chimica Acta (2003), 86(8), 2787-2796. Publisher: Verlag Helvetica Chimica Acta, CODEN: HCACAV
(R))
Abstract
Studies on the chem. constituents of the flowers of Azadirachta indica have led to the isolation of 2 new flavanones, flowerine
(5-hydroxy-7,4'-dimethoxy-8-(3-methylbut-2-enyl)flavan-4-one), and flowerone
(5,7,8,4'-tetrahydroxy-3'-(3-methylbut-3-enyl)flavan-4-one), and 2 new triterpenoids, O-methylazadironolide
(7α-(acetoxy)-23ξ-methoxy-21,23-epoxy-24,25,26,27-tetranorapotirucalla-1,14,20(22)-trien-3,21-dione), and diepoxyazadirol
((20S,23S,24R)-7-α-(acetoxy)-25-hydroxy-21,24:23,24-diepoxyapotirucalla-1,14-dien-3-one), along with the known triterpenoid
trichilenone acetate (7α-(acetoxy)-14,15:21,23-diepoxy-24,25,26,27-tetranorapotirucalla-1,20,22-trien-3-one), 2 known flavanones,
nimbaflavone (5,7-dihydroxy-4'-methoxy-8,3'-bis(3-methylbut-2-enyl)-flavan-4-one) and 3'-prenylnaringenin
(5,7,4'-trihydroxy-3'-(3-methylbut-2-enyl) flavan-4-one), and 4-(2-hydroxyethyl)phenol. Their structures were elucidated through
spectral studies, including 2D-NMR expts., and chem. transformation. Compds. 5, 7 and 8 are heretofore unreported from any part of
tree, while 6 was isolated earlier from leaves.
Answer 883:
Study of 202 Natural, Synthetic, and Environmental Chemicals for Binding to the Androgen Receptor. Fang, Hong; Tong,
Weida; Branham, William S.; Moland, Carrie L.; Dial, Stacy L.; Hong, Huixiao; Xie, Qian; Perkins, Roger; Owens, William; Sheehan,
Daniel M. Northrop Grumman Information Technology, Jefferson, AR, USA. Chemical Research in Toxicology (2003), 16(10),
flavanone
1338-1358. Publisher: American Chemical Society, CODEN: CRTOEC ISSN: 0893-228X. Journal written in English. CAN
Abstract
A no. of environmental and industrial chems. are reported to possess androgenic or antiandrogenic activities. These androgenic
endocrine disrupting chems. may disrupt the endocrine system of humans and wildlife by mimicking or antagonizing the functions of
natural hormones. The present study developed a low cost recombinant androgen receptor (AR) competitive binding assay that uses
no animals. We validated the assay by comparing the protocols and results from other similar assays, such as the binding assay
using prostate cytosol. We tested 202 natural, synthetic, and environmental chems. that encompass a broad range of structural
classes, including steroids, diethylstilbestrol and related chems., antiestrogens, flutamide derivs., bisphenol A derivs., alkylphenols,
parabens, alkyloxyphenols, phthalates, siloxanes, phytoestrogens, DDTs, PCBs, pesticides, organophosphate insecticides, and other
chems. Some of these chems. are environmentally persistent and/or com. important, but their AR binding affinities have not been
previously reported. To the best of our knowledge, these results represent the largest and most diverse data set publicly available for
chem. binding to the AR. Through a careful structure-activity relationship (SAR) examn. of the data set in conjunction with knowledge
of the recently reported ligand-AR crystal structures, we are able to define the general structural requirements for chem. binding to AR.
Hydrophobic interactions are important for AR binding. The interaction between ligand and AR at the 3- and 17-positions of
testosterone and R1881 found in other chem. classes are discussed in depth. The SAR studies of ligand binding characteristics for AR
are compared to our previously reported results for estrogen receptor binding.
Answer 884:
Inhibition of Peroxynitrite-Mediated LDL Oxidation by Prenylated Flavonoids: The α,β-Unsaturated Keto Functionality of
2'-Hydroxychalcones as a Novel Antioxidant Pharmacophore. Stevens, Jan F.; Miranda, Cristobal L.; Frei, Balz; Buhler, Donald
R. Department of Chemistry, Oregon State University, Corvallis, OR, USA. Chemical Research in Toxicology (2003), 16(10),
1277-1286. Publisher: American Chemical Society, CODEN: CRTOEC ISSN: 0893-228X. Journal written in English. CAN
Abstract
Prenylated 2'-hydroxychalcones and flavanones from the inflorescences of the female hop plant (Humulus lupulus) were shown to
inhibit peroxynitrite-mediated oxidn. of low-d. lipoproteins (LDL) at low micromolar concns. LDL oxidn. was induced by the peroxynitrite
generator, 3-morpholinosydnonimine (SIN-1), and measured by the formation of conjugated dienes and thiobarbituric reactive
substances. Human intake of prenylated chalcones and flavanones is mainly through beer, which contains up to 4 mg/L of these
polyphenols. The two main oxidn. products obtained by SIN-1 and peroxynitrite treatment of xanthohumol (XN), the principal
prenylflavonoid of hops, were the aurone, auroxanthohumol (AUXN), and an endoperoxy deriv. of XN, named endoperoxyxanthohumol
(EPOX). In addn., the reaction produced smaller amts. of the nitro and nitroso derivs. of XN and EPOX. The formation of these
nitrated products was enhanced in the presence of sodium bicarbonate (25 mM). SIN-1-induced formation of AUXN is considered to be
a superoxide-mediated reaction, while the structure of EPOX points to a two electron oxidn. reaction involving a Michael type addn. with
peroxynitrite as the nucleophile, followed by cyclization yielding a (1,2)-dioxepin-5-one ring structure. The flavanone isomer of XN,
isoxanthohumol (IsoXN), unexpectedly showed a slight prooxidant effect instead of an inhibitory effect on LDL oxidn. Except for the
formation of minor nitrated products, IsoXN remained largely unmodified upon treatment with SIN-1/peroxynitrite. Taken together, our
results suggest that the α,β-unsatd. keto functionality of chalcones is most reactive toward superoxide and peroxynitrite anions.
Answer 885:
Cuticular waxes and flavonol aglycons of mistletoes. Haas, Klaus; Bauer, Markus; Wollenweber, Eckhard. Universitaet
flavanone
Hohenheim, Institut fuer Botanik 210, Stuttgart, Germany. Zeitschrift fuer Naturforschung, C: Journal of Biosciences (2003),
58(7/8), 464-470. Publisher: Verlag der Zeitschrift fuer Naturforschung, CODEN: ZNCBDA ISSN: 0939-5075. Journal written in
Abstract
Cuticular waxes of Viscum album subspecies and of V. cruciatum have been examd. for their micromorphol. and chem. compn. Wax
crystalloids occur preferably as irregular platelets and rodlets, while deviant structures are found in small areas. Among the
triterpenoids forming the wax layer, oleanolic acid is prevailing with some 80%. The quant. compn. of the long-chain aliphatics, which
comprise several classes, is rather variable. Flavonoid aglycons, occurring as very minor components of the cuticular waxes,
comprise the flavonols kaempferol and quercetin and a series of their Me derivs., in some taxa also the flavanone naringenin. Neither
the crystalloid structures nor the chem. compn. of the wax allow to discriminate the 2 species, or male and female plants, or plants
grown on conifers or on dicotyledoneous hosts.
Answer 886:
Studies on the photochemistry of 1,7-diphenyl-1,6-heptadiene-3,5-dione, a non-phenolic curcuminoid model. Sundaryono,

Agus; Nourmamode, Aziz; Gardrat, Christian; Grelier, Stephane; Bravic, Georges; Chasseau, Daniel; Castellan, Alain. Laboratoire de
Chimie des Substances Vegetales, UPRES EA-494, Universite Bordeaux, Fr. Photochemical & Photobiological Sciences (2003),
2(9), 914-920. Publisher: Royal Society of Chemistry, CODEN: PPSHCB ISSN: 1474-905X. Journal written in English. CAN
Abstract
The comparative photostability of curcumin, and two non-phenolic curcuminoids: 1,7-diphenyl-1,6-heptadiene-3,5-dione (unsubstituted
curcumin) (I) and dimethylcurcumin in non-degassed dil. solns. (≈3-5 × 10-5 mol l-1) has been established by UV-visible absorption
spectroscopy; disappearance quantum yields were measured. The similar behavior of the three studied curcuminoids is indicative of
only a moderate role of phenol groups in the photodegrdn. process. Structural anal. of the photodegrdn. products of compd. I in more
concd. soln. (≈3.6 × 10-3 mol l-1) shows formation of benzaldehyde, cinnamaldehyde, 2'-hydroxy-5',6'-benzochalcone (II), flavanone III
and some other unidentified photoproducts. Flavanone III is formed by irradn. of chalcone II. It represents a unique example of
photochem. conversion of a diarylheptanoid mol. into a flavonoid, another very important class of natural products.
OH O
O O
II III
Answer 887:
Inhibition of inducible isoforms of cyclooxygenase and nitric oxide synthase by flavonoid hesperidin in mouse macrophage
cell line. Sakata, Keiko; Hirose, Yoshinobu; Qiao, Zheng; Tanaka, Takuji; Mori, Hideki. Department of Tumor Pathology, School
flavanone
of Medicine, Gifu University, Gifu, Japan. Cancer Letters (Oxford, United Kingdom) (2003), 199(2), 139-145. Publisher: Elsevier
Science Ltd., CODEN: CALEDQ ISSN: 0304-3835. Journal written in English. CAN 140:156879 AN 2003:708643 CAPLUS
Abstract
Previous data have shown that a citrus flavanone, hesperidin possesses chemopreventive efficacies. The authors designed to
investigate the inhibitory effect of hesperidin on lipopolysaccharide (LPS)-induced over-expression of cyclooxygenase-2 (COX-2),
inducible nitric oxide synthase (iNOS) proteins, over-prodn. of prostaglandin E2 (PGE2) and nitric oxide (NO) using mouse macrophage
cells. Treatment with hesperidin suppressed prodn. of PGE2, nitrogen dioxide (NO2), and expression of iNOS protein. In the case of
COX-2, hesperidin did not affect the protein level. The authors' data indicate hesperidin as a COX-2 and iNOS inhibitor, which might be
related to the anti-inflammatory and anti-tumorigenic efficacies.
Answer 888:
Isomerization of 4'-methoxy-flavanone in alkaline medium. Determination of the enolate formation constant. Andujar, S. A.;
Filippa, M. A.; Ferretti, F. H.; Blanco, S. E. Facultad de Quimica, Bioquimica y Farmacia, Area de Quimica-Fisica, Universidad
Nacional de San Luis, San Luis, Argent. THEOCHEM (2003), 636 157-166. Publisher: Elsevier Science B.V., CODEN: THEODJ
(R))
Abstract
The varied biol. activity of flavanones mainly depends on their phys. and chem. properties. In order to obtain information on the
acid-base behavior of flavanones of chem. and biol. interest the isomerization of 4'-methoxy-flavanone was studied and the formation
const. of its enolate was detd. by UV spectrometry. The kinetic expts. were performed in aq. medium at 25±0.1 °C, keeping the ionic
strength (0.07, KCl) and pH (10.8) const. The obtained results were interpreted by a four-step mechanism, which considered the
existence of flavanone enolate as a key intermediate. Some stereochem. and mechanistic aspects of the reaction were explained by
means of reactivity indexes and thermodn. magnitudes calcd. by ab initio methods in ethanol and water, which support the proposed
mechanism. It is concluded that the kinetic methodol. here proposed to study the enolization properties of flavanones seems to be
quite convenient to overcome the marked intrinsic instability of these substances in alk. media.
Answer 889:
SAR: flavonoids and COX-2 inhibition. Rosenkranz, Herbert S.; Thampatty, Bhavani P. Department of Biomedical Sciences,
Florida Atlantic University, Boca Raton, FL, USA. Oncology Research (2003), Volume Date 2002, 13(12), 529-535. Publisher:
Cognizant Communication Corp., CODEN: ONREE8 ISSN: 0965-0407. Journal written in English. CAN 140:246066 AN
Abstract
An anal. based upon structure-activity relationships (SAR) of the COX-2-inhibiting properties of flavonoids, a group of potential cancer
chemopreventive agents, reveals that there is a dual structural basis for these activities. Each of these structural determinants
(pharmacophores) alone is sufficient for activity. One of the pharmacophores is a 2D 6.9 .ANG. distance descriptor that spans the A
and C rings and includes the 4-oxo and 7-hydroxyl moieties. The potency assocd. with that pharmacophore is detd. by a series of
structural modulators that can increase, decrease, or even abolish the COX-2-inhibiting potential assocd. with that pharmacophore. The
flavanone
second pharmacophore describes a para-substituted phenolic B ring that requires unsubstituted meta and ortho positions. Based upon
this, it indicates that hydroxylation at the 4'-position and a free 5'-position are sufficient for COX-2-inhibiting activity. The potency
assocd. with this pharmacophore is modulated by log P2 and by the mol. wt.
Answer 890:
Flavonoids in buds and young needles of Picea, Pinus and Abies. Slimestad, R. PlantChem, Sandnes, Norway.
Biochemical Systematics and Ecology (2003), 31(11), 1247-1255. Publisher: Elsevier Science B.V., CODEN: BSECBU ISSN:
Abstract
A no. of flavonoids have been detected in buds and young needles in seven species of the genus Picea, four within the genus Pinus
and seven species within the genus Abies. The flavonoids were characterized by means of chromatog. (HPLC), spectroscopic (UV)
and spectrometric (MS) properties. Twenty-six flavonols, two flavones, four dihydroflavonols together with one dihydrochalcone and
one flavanone are reported, together with the relative abundances of the compds. within each species. Several flavonoids are reported
for the first time from the investigated trees.Among the flavonol glycosides found both in Picea and Abies, six 3-(6''-acetyl-glucosides)
and other acetyl-glucosides were detected. The most abundant sugar-moieties connected to the flavonoids are glucose and rutinose.
Flavonol-rhamnosides are present only in the Abies species. This genus also contains two flavone C-glycosides that occur as the
main flavonoids in some of the species. The Pinus species stood out for their less diverse content of flavonoids at this stage of
development compared to Picea and Abies.
Answer 891:
Synthesis and molluscicidal activity of flavanone derivatives. Qin, Zhanglan; Hu, Lihong; Pan, Kehua; Wei, Yunjie.
Department of Chemistry, Central China Normal University, Wuhan, Peop. Rep. China. Huaxue Yanjiu Yu Yingyong (2002),
14(4), 475-476, 483. Publisher: Huaxue Yanjiu Yu Yingyong Bianjibu, CODEN: HYYIFM ISSN: 1004-1656. Journal written in
Abstract
Eight flavanone derivs. I (R = Ph, substituted Ph) were prepd. by condensation of RCHO with malonic acid followed by cyclization with
1,3,5-benzenetriol. The biol. examn. showed that some of these compds. had good molluscicidal activity.
HO O R
OH O I
Answer 892:
flavanone
Chiral separation of diastereomeric flavanone-7-O-glycosides in citrus by capillary electrophoresis. Gel-Moreto, Nuria;

Streich, Rene; Galensa, Rudolf. Institut fuer Lebensmittelwissenschaft und -chemie, Rheinische Friedrich-Wilhelms-Universitaet
Bonn, Bonn, Germany. Electrophoresis (2003), 24(15), 2716-2722. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN:
ELCTDN ISSN: 0173-0835. Journal written in English. CAN 139:322532 AN 2003:684036 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
The 2S- and 2R-diastereomers of major flavanone-7-O-glycosides found in sweet orange (Citrus sinensis), mandarine (Citrus deliciosa),
grapefruit (Citrus paradisi), lemon (Citrus limon), and sour or bitter orange juice (Citrus aurantium) were sepd. for the first time by chiral
capillary electrophoresis (CE) employing various buffers with combined chiral selectors. Native cyclodextrins (CDs), neutral and
charged CD derivs. were examd. as chiral additives to the background electrolyte (BGE). Sepn. efficiency has not proved
satisfactory with one single CD as chiral selector in the buffer, a full and simultaneous sepn. could often be achieved only by using
combined buffer with two different CDs. Chiral sepn. of major flavanones in sweet orange, mandarine and grapefruit juices raised
more difficulties than in lemon and sour orange juices as narirutin will not readily build complexes with most CDs. Diastereomeric
flavanones of mature and immature grapefruits were compared and some differences were found: naringin showed different
diastereomeric ratio and 2S-prunin appeared only in immature grapefruit. Marmalade was also examd. by chiral CE. Its major
flavanones corresponded to flavanone pattern of mixed sour and sweet oranges.
Answer 893:
Separation of some chiral flavanones by micellar electrokinetic chromatography. Asztemborska, Monika; Miskiewicz,
Magdalena; Sybilska, Danuta. Institute of Physical Chemistry, Polish Academy of Sciences, Warsaw, Pol. Electrophoresis
(2003), 24(15), 2527-2531. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: ELCTDN ISSN: 0173-0835. Journal written
Abstract
Micellar electrokinetic chromatog. (MEKC) was applied for enantiosepn. of selected flavanones, including naringin, hesperidin,
neohesperidin, naringenin, hesperetin, pinostrobin, isosakuranetin, eriodictyol, and homoeriodictyol. γ-Cyclodextrin (γ-CD) and sodium
cholate (SCh) were used as chiral modifiers inducing enantio-selectivity to the background electrolyte. From among many studied
selectors only these two appeared to possess the best enantioselective properties in respect to studied flavanones. The mechanisms
of their action are a little different; SCh used above crit. micelle point concn. forms chiral micelles itself while γ-CD is deprived of this
property and requires addn. of surfactants as, e.g., sodium dodecyl sulfate. SCh enables sepn. of flavanone glycosides
diastereomers while sepn. of enantiomers of flavanone aglycons may be achieved with γ-CD. Consideration of structural relation led
to the suggestion that interaction of sugar moiety of glycosides with SCh micelles give rise to chiral recognition. MEKC appeared to be
a suitable and efficient anal. tool to follow enantiomeric compn. of flavanones.
Answer 894:
Constituents of the Stem Bark of Pongamia pinnata with the Potential to Induce Quinone Reductase. Carcache-Blanco,
Esperanza J.; Kang, Young-Hwa; Park, Eun Jung; Su, Bao-Ning; Kardono, Leonardus B. S.; Riswan, Soedarsono; Fong, Harry H. S.;
Pezzuto, John M.; Kinghorn, A. Douglas. Program for Collaborative Research in the Pharmaceutical Sciences and Department of
Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois, Chicago, IL, USA. Journal of Natural
Products (2003), 66(9), 1197-1202. Publisher: American Chemical Society, CODEN: JNPRDF ISSN: 0163-3864. Journal written in
flavanone
Abstract
Activity-guided fractionation of the petroleum ether and Et acetate exts. of the stem bark of Pongamia pinnata, using cultured Hepa
1c1c7 mouse hepatoma cells to evaluate quinone reductase (QR) inducing activity, led to the isolation of four new flavanone derivs.
(1-4), one new flavone (5), one new chalcone (6), and 13 known compds. of the flavonoid, terpenoid, and fatty acid types. The
structures of 1-6 were characterized on the basis of the interpretation of their spectroscopic data. The abs. stereochem. of compds.
1-4 was detd. from their CD data and by Mosher ester detn. All isolates obtained were evaluated in the quinone reductase induction
assay.
Answer 895:
Abscisic acid and 2,4-dichlorophenoxyacetic acid affect the expression of anthocyanin biosynthetic pathway genes in
'Kyoho' grape berries. Ban, T.; Ishimaru, M.; Kobayashi, S.; Shiozaki, S.; Goto-Yamamoto, N.; Horiuchi, S. Faculty of Life and
Environmental Science, Shimane University, Kamihonjo, Matsue, Shimane, Japan. Journal of Horticultural Science &
Biotechnology (2003), 78(4), 586-589. Publisher: Headley Brothers Ltd., CODEN: JHSBFA ISSN: 1462-0316. Journal written in
Abstract
The effects of abscisic acid (ABA) and 2,4-D on the expression of seven anthocyanin biosynthetic pathway genes in 'Kyoho' grape
berries were investigated. In untreated berries, the expression of the UDP-glucose-flavonoid: 3-O-glucosyltransferase (UFGT) gene
was detected only at 42 d after full bloom (DAB), whereas the phenylalanine ammonia-lyase (PAL), chalcone synthase (CHS),
chalcone isomerase (CHI), flavanone-3-hydroxylase (F3H), dihydroflavonol 4-reductase (DFR) and leucoanthocyanidin dioxygenase
(LDOX) genes were expressed throughout the growing period. ABA increased anthocyanin content in the skin and the expression of
PAL, CHS, CHI, DFR and UFGT genes at 7 d after treatment. In contrast, 2,4-D inhibited the accumulation of anthocyanin and the
expression of all the genes examd. Thus, the anthocyanin levels resulting from the application of ABA and 2,4-D were correlated with
the expression of anthocyanin biosynthetic pathway genes.
Answer 896:
Flavonoid compounds of Larix sibirica and Larix gmelinii bark. Ivanova, S. Z.; Fedorova, T. E.; Ivanova, N. V.; Fedorov, S.
V.; Ostroukhova, L. A.; Malkov, Yu. A.; Babkin, V. A. Irk. Inst. Khim. im. A. E. Favorskogo, SO RAN, Irkutsk, Russia. Khimiya
Rastitel'nogo Syr'ya (2003), Volume Date 2002, (4), 5-13. Publisher: IzdatelÏstvo Altaiskogo Gosudarstvennogo Universiteta,
CODEN: KRSHC4 ISSN: 1029-5151. Journal written in Russian. CAN 140:300406 AN 2003:669598 CAPLUS (Copyright (C)
Abstract
The flavonoid compds. of Larix sibirica Ledeb. and Larix gmelinii (Rupr.) Rupr. bark were investigated. Their classification was carried
out according to modern views on their biochem. interrelations. It was shown that in the bark there were representatives of practically
all flavonoid classes, from flavanone naringenin up to biflavonoids, proanthocyanidins and condensed tannins. Notably, the flavonoid
compds. can be classified into two basic groups, judging from B ring hydroxylation type, p-hydroxyphenyl (monosubstituted) and
catechol (disubstituted), with the prevalence of the first type. Obviously, biflavonoids of a spiro-type are present in oligo- and
polymeric flavonoids compds. as structural parts.
Answer 897:
flavanone
Antifungal flavanones and prenylated hydroquinones from Piper crassinervium Kunth. Danelutte, Ana Paula; Lago, Joao
Henrique G.; Young, Maria Claudia M.; Kato, Massuo J. Instituto de Quimica, Universidade de Sao Paulo, Sao Paulo, Brazil.
Phytochemistry (Elsevier) (2003), 64(2), 555-559. Publisher: Elsevier Science B.V., CODEN: PYTCAS ISSN: 0031-9422. Journal
Abstract
Bioactivity-guided fractionation of the EtOAc ext. from leaves of Piper crassinervium yielded three prenylated hydroquinones - the E
and Z isomers of 1,4-dihydroxy-2-(3',7'-dimethyl-1'-oxo-2',6'-octadienyl)benzene and I - together with the known flavanones naringenin
and sakuranetin. The structures were detd. by means of spectroscopic anal. (NMR, IR, UV and MS), including two-dimensional NMR
spectroscopy expts. (1H-1H COSY, HMQC, HMBC and NOESY). The antifungal activity was detd. by direct bioautog. against
Cladosporium cladosporioides and C. sphaerospermum.
OH O CH 2
O
O Me
OH Me I
Answer 898:
Flavanone 3-hydroxylase expression in Citrus paradisi and Petunia hybrida seedlings. Pelt, Jennifer L.; Downes, W.
Andrew; Schoborg, Robert V.; McIntosh, Cecilia A. Department of Biological Sciences, East Tennessee State University, Johnson
City, TN, USA. Phytochemistry (Elsevier) (2003), 64(2), 435-444. Publisher: Elsevier Science B.V., CODEN: PYTCAS ISSN:
Abstract
Petunia hybrida and Citrus paradisi have significantly different flavonoid accumulation patterns. Petunia sp. tend to accumulate
flavonol glycosides and anthocyanins while Citrus paradisi is known for its accumulation of flavanone diglycosides. One possible
point of regulation of flavanone metab. is flavanone 3-hydroxylase (F3H) expression. To test whether this is a key factor in the
different flavanone usage by Petunia hybrida and Citrus paradisi, F3H mRNA expression in seedlings of different developmental
stages was measured using semiquant. RT-PCR. Primers were designed to conserved regions of F3H and used to amplify an approx.
350 bp segment for quantitation by PhosphorImaging. Primary leaves of 32-day-old grapefruit seedlings and a grapefruit flower bud
had the highest levels of F3H mRNA expression. Petunia seedlings had much lower levels of F3H mRNA expression relative to
grapefruit. The highest expression in petunia was in primary leaves and roots of 65-day-old seedlings. These results indicate that
preferential use of naringenin for prodn. of high levels of flavanone glycosides in young grapefruit leaves cannot be attributed to
decreased F3H mRNA expression.
Answer 899:
flavanone
Synthesis, antiinflammatory and antibacterial activity of some new flavonoidal derivatives. Khan, M. S. Y.; Hasan, S. M.
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, New Delhi, India. Indian Journal of Chemistry, Section B:
Organic Chemistry Including Medicinal Chemistry (2003), 42B(8), 1970-1974. Publisher: National Institute of Science
Communication, CODEN: IJSBDB ISSN: 0376-4699. Journal written in English. CAN 140:128244 AN 2003:661356 CAPLUS
Abstract
Several flavones I (R1 = MeO; R2 = H; R1R2 = OCH2O), flavanones II (R3 = H, MeO), and 5'-substituted-2'-hydroxy chalcones, e.g.,
III, have been synthesized through Claisen Schmidt condensation. Condensation of 5-Chloromethyl-2-hydroxyacetophenone with
various arom. aldehydes yielded chalcones, which were cyclized, in the presence of SeO2, to the corresponding flavones I.
Condensation of 5-(2-methylphenylamino)methyl-2-hydroxyacetophenone with arom. aldehydes gave the corresponding chalcones and
flavones. The synthesized flavonoid derivs. were evaluated for their antiinflammatory activity on carrageenan induced paw edema in
rats and in vitro antibacterial activity. The results have been encouraging.
R1
O
R2
Et O
O I
R3
O
Me H
O
II
OH
Me H O
O III
flavanone
Answer 900:
Potential Cancer Chemopreventive Flavonoids from the Stems of Tephrosia toxicaria. Jang, Dae Sik; Park, Eun Jung; Kang,
Young-Hwa; Hawthorne, Michael E.; Vigo, Jose Schunke; Graham, James G.; Cabieses, Fernando; Fong, Harry H. S.; Mehta,
Rajendra G.; Pezzuto, John M.; Kinghorn, A. Douglas. Program for Collaborative Research in the Pharmaceutical Sciences and
Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, and Department of Surgical Oncology, College of
Medicine, University of Illinois at Chicago, Chicago, IL, USA. Journal of Natural Products (2003), 66(9), 1166-1170. Publisher:
American Chemical Society, CODEN: JNPRDF ISSN: 0163-3864. Journal written in English. CAN 139:304575 AN 2003:657115
Abstract
A new butenylflavanone, (2S)-5-hydroxy-7-methoxy-8-[(E)-3-oxo-1-butenyl]flavanone (1), and a new rotenoid,

4',5'-dihydro-11,5'-dihydroxy-4'-methoxytephrosin (2), as well as three active flavonoids of previously known structure, isoliquiritigenin
(3), genistein (4), and chrysoeriol (5), along with nine known inactive compds., α-toxicarol (6), sumatrol, 6a,12a-dehydro-α-toxicarol,
11-hydroxytephrosin, obovatin, marmesin, lupenone, benzyl benzoate, and benzyl trans-cinnamate, were isolated from an Et
acetate-sol. ext. of the stems of Tephrosia toxicaria, using a bioassay based on the induction of quinone reductase (QR) in cultured
Hepa 1c1c7 mouse hepatoma cells to monitor chromatog. fractionation. The structures of compds. 1 and 2 were elucidated by
spectroscopic data interpretation. All isolates were evaluated for their potential cancer chemopreventive properties utilizing an in vitro
assay to det. quinone reductase induction. Selected compds. were tested in a mouse mammary organ culture assay to evaluate the
inhibition of 7,12-dimethylbenz[a]anthracene (DMBA)-induced preneoplastic lesions.
Answer 901:
Synthesis of 1-(di- and trihydroxyphenyl)-3-pyridinepropenones: Precursors for pyridine 3-chromones. Rafiq, Somaira;
Wachter, Nanette M. Department of Chemistry, Hofstra University, Hempstead, NY, USA. Abstracts of Papers, 226th ACS
National Meeting, New York, NY, United States, September 7-11, 2003 (2003), CHED-189. Publisher: American Chemical Society,
Washington, D. C CODEN: 69EKY9 Conference; Meeting Abstract written in English. AN 2003:630530 CAPLUS (Copyright (C)
Abstract
Pyridinyl derivs. of chalcones and flavones have been synthesized in order to investigate their antioxidant properties. Flavones are
synthesized by oxidative cyclization of the chalcones in the presence of alk. solns. of hydrogen peroxide. However, under the alk.
conditions used to synthesize the chalcones, cycloisomerization of ortho-hydroxy chalcones to isomeric flavanones complicates the
transformation of these compds. to the desired flavones. To prevent this, the hydroxy groups of di-and trihydroxyacetophenones are
replaced with methoxy groups. Protection of the phenolic oxygens with Me groups facilitates condensation and impedes
cycloisomerization of resulting chalcone to the flavanone. Demethylation results on treatment of the dimethoxychalcones with
trimethylsilyliodide (TMSI). The deprotected polyhydroxychalcones can then be oxidatively cyclized to the desired flavones. All the
products synthesized were analyzed by either GC-MS or HPLC, and proton NMR spectroscopy.
Answer 902:
Comparative performances of selected chiral HPLC, SFC, and CE systems with a chemically diverse sample set. Borman,
flavanone
Phil; Boughtelower, Bob; Cattanach, Kaye; Crane, Kathy; Freebairn, Keith; Jonas, Greg; Mutton, Ian; Patel, Asha; Sanders, Matt;
Thompson, Duncan. Strategic Technologies, GlaxoSmithKline, Stevenage, UK. Chirality (2003), 15(Suppl.), S1-S12. Publisher:
Wiley-Liss, Inc., CODEN: CHRLEP ISSN: 0899-0042. Journal written in English. CAN 139:373796 AN 2003:625324 CAPLUS
Abstract
Pharmaceutical companies have a continuous need to resolve new racemates. Anal. may be required in aq. and nonaq. media, or in
the presence of several different sets of potentially interfering compds. There is often a preparative requirement. For these reasons
analysts may require a no. of different sepn. systems capable of resolving a given pair of enantiomers. The authors wished to
improve upon existing approaches that address this situation and undertook a program of work to screen over 100 racemates, selected
for their chem. diversity, on over 100 different chiral HPLC, SFC, and CE systems. Here the authors report results of this
comparison and illustrate the use of rapid gradient screening as a valuable tool for chiral method development.
Answer 903:
New potent antioxidative hydroxyflavanones produced with Aspergillus saitoi from flavanone glycoside in citrus fruit.
Miyake, Yoshiaki; Minato, Kenichiro; Fukumoto, Syuichi; Yamamoto, Kanefumi; Oya-Ito, Tomoko; Kawakishi, Syunro; Osawa,
Toshihiko. Fundamental Technical Research Department of Pokka Corporation Ltd., Aichi, Japan. Bioscience, Biotechnology, and
Biochemistry (2003), 67(7), 1443-1450. Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry, CODEN:
BBBIEJ ISSN: 0916-8451. Journal written in English. CAN 139:306597 AN 2003:613685 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
Potent antioxidative hydroxyflavanones were produced with Aspergillus saitoi from hesperidin or naringin, which are flavanone
glycosides in citrus fruit with weak antioxidative activity. The hydroxyflavanone produced from hesperidin was identified as
8-hydroxyhesperetin (8-HHE), a novel substance, and those from naringin were identified as carthamidin (6-hydroxynaringenin) and
isocarthamidin (8-hydroxynaringenin) by FAB-MS, 1H-NMR and 13C-NMR analyses. The antioxidative activity of these
hydroxyflavanones was examd. by using the free radical-scavenging system of 1,1-diphenyl-2-picrylhydrazyl (DPPH) and the Me
linoleate oxidn. system. The hydroxyflavanones (8-HHE, carthamidin, and isocarthamidin) exhibited stronger activity than the
flavanone glycosides (hesperidin or naringin) and their aglycons (hesperetin or naringenin). The activity of 8-HHE and isocarthamidin
was comparable to that of α-tocopherol, and that of carthamidin was weaker than that of isocarthamidin. The hydroxyflavanones,
which were hydroxylated on A ring of flavanone by Aspergillus saitoi, were obtained as potent antioxidants.
Answer 904:
Synthesis of Luteolin and Orobol. Ge, Xia; Li, Jianqi. Shanghai Institute of Pharmaceutical Industry, Shanghai, Peop. Rep.
China. Zhongguo Yiyao Gongye Zazhi (2003), 34(4), 159-161. Publisher: Zhongguo Yiyao Gongye Zazhi Bianjibu, CODEN:
ZYGZEA ISSN: 1001-8255. Journal written in Chinese. CAN 140:111145 AN 2003:597202 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
Luteolin and Orobol were synthesized in three steps via chloromethyl Me ether protected ketone phenol and aldehyde phenol, forming
chalcone deriv., further oxidative intramol. cyclization, giving polyhydroxy flavanone and isoflavanone. The overall yield of Luteolin
flavanone
and Orobol was 22% and 15%, resp.
Answer 905:
Benzophenone synthase and chalcone synthase from Hypericum androsaemum cell cultures: cDNA cloning, functional
expression, and site-directed mutagenesis of two polyketide synthases. Liu, Benye; Falkenstein-Paul, Hildegard; Schmidt,
Werner; Beerhues, Ludger. Institut fuer Pharmazeutische Biologie, Braunschweig, Germany. Plant Journal (2003), 34(6),
847-855. Publisher: Blackwell Publishing Ltd., CODEN: PLJUED ISSN: 0960-7412. Journal written in English. CAN 140:195315
Abstract
Benzophenone derivs., such as polyprenylated benzoylphloroglucinols and xanthones, are biol. active secondary metabolites. The
formation of their C13 skeleton is catalyzed by benzophenone synthase (BPS; EC 2.3.1.151) that has been cloned from cell cultures
of Hypericum androsaemum. BPS is a novel member of the superfamily of plant polyketide synthases (PKSs), also termed type III
PKSs, with 53-63% amino acid sequence identity. Heterologously expressed BPS was a homodimer with a subunit mol. mass of 42.8
kDa. Its preferred starter substrate was benzoyl-CoA that was stepwise condensed with three malonyl-CoAs to give
2,4,6-trihydroxybenzophenone. BPS did not accept activated cinnamic acids as starter mols. In contrast, recombinant chalcone
synthase (CHS; EC 2.3.1.74) from the same cell cultures preferentially used 4-coumaroyl-CoA and also converted CoA esters of
benzoic acids. The enzyme shared 60.1% amino acid sequence identity with BPS. In a phylogenetic tree, the two PKSs occurred in
different clusters. One cluster was formed by CHSs including the one from H. androsaemum. BPS grouped together with the PKSs
that functionally differ from CHS. Site-directed mutagenesis of amino acids shaping the initiation/elongation cavity of CHS yielded a
triple mutant (L263M/F265Y/S338G) that preferred benzoyl CoA over 4-coumaroyl-CoA.
Answer 906:
Separation of diastereomers of flavanone-7-O-glycosides by capillary electrophoresis using sulfobutyl ether-β-cyclodextrin

as the selector. Aturki, Zeineb; Sinibaldi, Massimo. Istituto di Metodologie Chimiche, CNR - Area della Ricerca di Roma, Rome,
Italy. Journal of Separation Science (2003), 26(9/10), 844-850. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN:
JSSCCJ ISSN: 1615-9306. Journal written in English. CAN 139:316176 AN 2003:589969 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
A method was developed for the sepn. of diastereomers of flavanone-7-O-glycosides by capillary electrophoresis using sulfobutyl
ether-β-cyclodextrin (SBE-β-CD) in the background electrolyte. The effect of the concn. of the CD additive, buffer pH, and org.
modifier on the migration times and resoln. for five flavanone glycosides (naringin, hesperidin, neohesperidin, narirutin, and eriocitrin)
was studied. Baseline sepns. of these compds. as pairs of diastereoisomers were achieved with 20 mM tetraborate buffer at pH 7
contg. 5 mg/mL of SBE-β-CD and 10% (vol./vol.) of methanol. The developed method was used for the qual. anal. of the
diastereomeric compn. of the major flavanone glycosides in different citrus juices. The ability of SBE-β-CD to discriminate flavanone
enantiomers was also studied.
Answer 907:
flavanone
Influence of solvents and temperature on the photophysical characteristics of flavanones. Giri, Rajesh; Tiwari, Yatendra.
Department of Physics, Rajdhani College (Delhi University), New Delhi, India. Indian Journal of Pure and Applied Physics (2003),
41(7), 530-537. Publisher: National Institute of Science Communication, CODEN: IJOPAU ISSN: 0019-5596. Journal written in
Abstract
The absorption and fluorescence emission spectra of substituted flavanones viz., flavanone, 6-Me flavanone, and
6-methyl-4'-methoxy flavanone, have been reported in various polar and nonpolar org. solvents. The values of excited state dipole
moments of these flavanones have been calcd., using solvatochromic data. The values of excited state dipole moments for all these
mols. studied, are higher than their corresponding values in the ground state. Also the excited state dipole moment of
6-methyl-4'-methoxy flavanone > 6-Me flavanone > flavanone. Further, the values of percentage polarization of these mols. in
various solvents of different polarity have been obtained and interpreted in terms of Perrin's theory as well as dipole-dipole interaction.
Also, the effect of temp. on fluorescence intensity in H2O and a nonpolar solvent have been obsd. The variations in the fluorescence
intensity have been discussed in terms of the positions of 1(π π*) and 3(n π*) energy levels of the mols. studied.
Answer 908:
Antioxidant Chalcone Glycosides and Flavanones from Maclura (Chlorophora) tinctoria. Cioffi, Giuseppina; Escobar, Luis
Morales; Braca, Alessandra; De Tommasi, Nunziatina. Dipartimento di Scienze Farmaceutiche, Universita di Salerno, Fisciano,
Italy. Journal of Natural Products (2003), 66(8), 1061-1064. Publisher: American Chemical Society, CODEN: JNPRDF ISSN:
Abstract
Four chalcone glycosides, including three new natural products, and three flavanones were isolated from the methanol ext. of stem
bark of Maclura tinctoria. The new compds. have been characterized as
4'-O-β-D-(2''-p-coumaroyl)glucopyranosyl-4,2',3'-trihydroxychalcone,
4'-O-β-D-(2''-p-coumaroyl-6''-acetyl)glucopyranosyl-4,2',3'-trihydroxychalcone, and
3'-(3-methyl-2-butenyl)-4'-O-β-D-glucopyranosyl-4,2'-dihydroxychalcone (I); the known derivs. were elucidated as
4'-O-β-D-(2''-acetyl-6''-cinnamoyl)glucopyranosyl-4,2',3'-trihydroxychalcone, eriodictyol 7-O-β-D-glucopyranoside, naringenin, and
naringenin 4'-O-β-D-glucopyranoside. Their structures were detd. by 1D and 2D NMR and ESIMS. The antioxidant activity of all
isolated compds. was detd. by measuring free-radical-scavenging effects using two different assays, namely, the Trolox Equiv.
Antioxidant Capacity (TEAC) assay and the coupled oxidn. of β-carotene and linoleic acid (autoxidn. assay). The results showed that I
was the most active in both antioxidant assays.
Answer 909:
Chemical constituents of Vitex negundo leaves. Singh, Virendra; Dayal, Rameshwar; Bartley, John P. Chemistry Division,
Forest Research Institute, Dehra dun, India. Journal of Medicinal and Aromatic Plant Sciences (2003), 25(1), 94-98. Publisher:
Central Institute of Medicinal and Aromatic Plants, CODEN: JMASF6 Journal written in English. CAN 140:108101 AN
Abstract
Twelve pure compds., namely viridiflorol; squalene; β-sitosterol; 5-hydroxy-3,6,7,3',4'-pentamethoxy flavone;

flavanone
5-hydroxy-3,7,3',4'-tetramethoxy flavone; 5,3'-dihydroxy-7,8,4'-trimethoxy flavanone; p-hydroxybenzoic acid; 3,4-dihydroxy benzoic

acid; luteolin 7-glucoside; isoorientin; agnuside and 2'-p-hydroxybenzoyl mussaenosidic acid were isolated and characterized by spectral
data (UV, IR, NMR & MS) from the different extractives of the leaves. Squalene is reported for the first time from the V. negundo
leaves. Agnuside was found to possess significant hepatoprotective activity while viridiflorol exhibited dose dependant antifeedant
against Sitophilus oryzae and ovipositional activity against Callosobruchus chinensis.
Answer 910:
Metabolic engineering to increase isoflavone biosynthesis in soybean seed. Yu, Oliver; Shi, June; Hession, Aideen O.;
Maxwell, Carl A.; McGonigle, Brian; Odell, Joan T. Experimental Station, Crop Genetics, E.I. du Pont de Nemours & Company, Inc.,
Wilmington, DE, USA. Phytochemistry (Elsevier) (2003), 63(7), 753-763. Publisher: Elsevier Science B.V., CODEN: PYTCAS
SciFinder (R))
Abstract
Isoflavone levels in Glycine max (soybean) were increased via metabolic engineering of the complex phenylpropanoid biosynthetic
pathway. Phenylpropanoid pathway genes were activated by expression of the maize C1 and R transcription factors in soybean seed,
which decreased genistein and increased the daidzein levels with a small overall increase in total isoflavone levels. Cosuppression of
flavanone 3-hydroxylase to block the anthocyanin branch of the pathway, in conjunction with C1/R expression, resulted in higher
levels of isoflavones. The combination of transcription factor-driven gene activation and suppression of a competing pathway
provided a successful means of enhancing accumulation of isoflavones in soybean seed.
Answer 911:
Expression of anthocyanins and proanthocyanidins after transformation of alfalfa with maize Lc. Ray, Heather; Yu, Min;
Auser, Patricia; Blahut-Beatty, Laureen; McKersie, Brian; Bowley, Steve; Westcott, Neil; Coulman, Bruce; Lloyd, Alan; Gruber,
Margaret Y. Saskatoon Research Centre, Agriculture and Agri-Food Canada, Saskatoon, SK, Can. Plant Physiology (2003),
132(3), 1448-1463. Publisher: American Society of Plant Biologists, CODEN: PLPHAY ISSN: 0032-0889. Journal written in English.
Abstract
Three anthocyanin regulatory genes of maize (Zea mays; Lc, B-Peru, and C1) were introduced into alfalfa (Medicago sativa) in a
strategy designed to stimulate the flavonoid pathway and alter the compn. of flavonoids produced in forage. Lc constructs included a
full-length gene and a gene with a shortened 5'-untranslated region. Lc RNA was strongly expressed in Lc transgenic alfalfa foliage,
but accumulation of red-purple anthocyanin was obsd. only under conditions of high light intensity or low temp. These stress
conditions induced chalcone synthase and flavanone 3-hydroxylase expression in Lc transgenic alfalfa foliage compared with
non-transformed plants. Genotypes contg. the Lc transgene construct with a full-length 5'-untranslated region responded more quickly
to stress conditions and with a more extreme phenotype. High-performance liq. chromatog. anal. of field-grown tissue indicated that
flavone content was reduced in forage of the Lc transgenic plants. Leucocyanidin reductase, the enzyme that controls entry of
metabolites into the proanthocyanidin pathway, was activated both in foliage and in developing seeds of the Lc transgenic alfalfa
genotypes. Proanthocyanidin polymer was accumulated in the forage, but (+)-catechin monomers were not detected. B-Peru
transgenic and C1 transgenic populations displayed no visible phenotypic changes, although these transgenes were expressed at
detectable levels. These results support the emerging picture of Lc transgene-specific patterns of expression in different recipient
species. These results demonstrate that proanthocyanidin biosynthesis can be stimulated in alfalfa forage using an myc-like
transgene, and they pave the way for the development of high quality, bloat-safe cultivars with ruminal protein bypass.
flavanone
Answer 912:
Flavonoids: Mechanism of action and application possibilities (part 2). Bergmann, Ralf; Wuest, Frank; Pietzsch, Jens.
Institut fuer Bioanorganische und Radiopharmazeutische Chemie, Forschungszentrum Rossendorf, Dresden, Germany. Bioforum
(2003), 26(6), 384-385. Publisher: GIT Verlag GmbH & Co. KG, CODEN: BFRME3 ISSN: 0940-0079. Journal; General Review
written in German. CAN 139:113689 AN 2003:553014 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))
Abstract
A review is given on the radiochem. marking of flavonoids with 11C for radiopharmaceutical examns. with positron emission tomog.
11C synthesis methods are outlined and examples of resulting flavonoids are given such as hesperitin, glycetein, xanthotumol-like
flavonoids and flavanones, and resveratrol.
Answer 913:
First Synthesis of (±)-C-3-Prenylated Flavanones. Xu, Jin; Wang, Haishan; Mui Sim, Mui. Medicinal and Combinatorial
Chemistry Laboratory, Institute of Molecular and Cell Biology, Singapore, Singapore. Synthetic Communications (2003), 33(15),
2737-2750. Publisher: Marcel Dekker, Inc., CODEN: SYNCAV ISSN: 0039-7911. Journal written in English. CAN 139:395780
Abstract
2,4,6-Tris(methoxymethoxy)acetophenone was first mono-alkylated with 3-methylbut-2-enyl bromide to yield

5-methyl-1-[2,4,6-tris(methoxymethoxy)phenyl]hex-4-en-1-one (I). The base-catalyzed aldol condensation of I with substituted
benzaldehydes gave chalcones in good yields. One-pot cyclization and deprotection of the chalcones afforded (±)-C-3-prenylated
flavanones II (R1 = R3 = OH; R2 = R4 = H; R1 = R4 = H; R2 = R3 = OH; R1 = R2 = R4 = H; R3 = OMe, OH; R1 = R3 = R4 = OMe;
R2 = H).
flavanone
MOM O OMOM
Me
OMOM O Me I
R4
R3
HO O
R2
R1
OH O Me
Me II
Answer 914:
Antitumor agents containing artocarpin or its analogs. Kondo, Ryuichiro; Shimizu, Kuniyoshi; Yoshikawa, Keisuke. (Kansai
Koso Co., Ltd., Japan). Jpn. Kokai Tokkyo Koho (2003), 4 pp. CODEN: JKXXAF JP 2003192590 A 20030709 Patent written
in Japanese. Application: JP 2001-394637 20011226. Priority: . CAN 139:63323 AN 2003:527529 CAPLUS (Copyright (C)

JP 2003192590 A 20030709 JP 2001-394637 20011226
JP 2001-394637 20011226
Abstract
Antitumor agents, esp. useful for treatment of skin cancers, contain artocarpins I (R = H, C1-10 alkyl, acyl) as active ingredients.
IC50 of artocarpin (II) against B16 melanoma cells was 5.4 μM, vs. 50 μM of vinblastine sulfate. II also inhibited proliferation of
human melanoma cells, human breast cancer MCF-7 cells, human leukemia HL 60 cells, and HeLa cells. In vivo antitumor effect of II
in mice bearing B16 melanoma cells was excellent.
flavanone
RO OR
RO O
OR O
Answer 915:
Cosmetic composition packaged with material having Al-deposition layer for refilling. Nishida, Yuichi; Kon, Akira; Tobe,
Hidetake. (Lion Corp., Japan). Jpn. Kokai Tokkyo Koho (2003), 16 pp. CODEN: JKXXAF JP 2003192560 A 20030709 Patent
written in Japanese. Application: JP 2001-403023 20011227. Priority: . CAN 139:73723 AN 2003:525350 CAPLUS (Copyright

JP 2003192560 A 20030709 JP 2001-403023 20011227
JP 2001-403023 20011227
Abstract
The invention relates to a cometic compn. for refilling, e.g. shampoo, body soap, cleansing gel, etc., wherein the compn. contains
ketone fragrances having a steam pressure at 25° of 0.001-7 mmHg and a HLB of 2-13, and wherein the compn. is sealed in a
container having aluminum deposition layer. The cosmetic compn. of the present invention has improved stability, esp. the aroma
stability.
Answer 916:
Study on the chemical constituents of Populus davidiana Dode. Zhou, Shan; Lin, Mao; Wang, Yinghong; Liu, Xin. Institute of
Materia Medica, Chinese Academy of Medical Sciences, Beijing, Peop. Rep. China. Tianran Chanwu Yanjiu Yu Kaifa (2002), 14(5),
43-45. Publisher: Tianran Chanwu Yanjiu Yu Kaifa Bianjibu, CODEN: TCYKE5 ISSN: 1001-6880. Journal written in Chinese. CAN
flavanone
Abstract
From the bark of Populus davidiana Dode., seven flavonoids were isolated and identified as galangin, chrysin, tectochrysin,
genkwanin, ombuin, pinocembrin and trans-3-acetoxy-5,7-dihydroxyflavanone, resp. Ombuin and
trans-3-acetoxy-5,7-dihydroxy-flavanone were isolated from the genus for the first time. Galangin, tectochrysin and ombuin had
strong anti-inflammatory activity.
Answer 917:
Studies on the chemical constituents of Spatholobus suberectus Dunn. Cui, Yanjun; Liu, Ping; Chen, Ruoyun. Institute of
Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peop. Rep. China. Yaoxue
Xuebao (2002), 37(10), 784-787. Publisher: Yaoxue Xuebao Bianjibu, CODEN: YHHPAL ISSN: 0513-4870. Journal written in
Abstract
The chem. constituents of Spatholobus suberectus (jixueteng) Dunn were studied. The constituents of Spatholobus suberectus were
sepd. with various chromatog. techniques. The structures were elucidated by physico-chem. properties and spectral data. Eight
compds. were isolated from Spatholobus suberectus Dunn and identified as suberectin (1), formononetin (2), daidzein, calycosin (4),
pyromucic acid (5), 1,3,5-benzenetriol (6), succinic acid (7), and β-sitosterol (8). Suberectin was a new compd. and characterized as
7,3',4'-trihydroxy-6-methoxyflavanone based on chem. and spectral evidence. Compds. 4, 5, 6, and 7 were obtained from
Spatholobus genus for the first time.
Answer 918:
Conserved structural modules and bonding networks in isopenicillin N synthase related non-haem iron-dependent
oxygenases and oxidases. Sim, Janet; Wong, Esther; Chin, Hong Soon; Sim, Tiow Suan. Faculty of Medicine, Department of
Microbiology, National University of Singapore, Singapore, Singapore. Journal of Molecular Catalysis B: Enzymatic (2003), 23(1),
17-27. Publisher: Elsevier Science B.V., CODEN: JMCEF8 ISSN: 1381-1177. Journal written in English. CAN 140:141603 AN
Abstract
Analyses of attainable primary amino acid sequences, assigned secondary structures and superimposed tertiary structures of 142
isopenicillin N synthase (IPNS) related non-heme iron-dependent oxygenases and oxidases (designated as NHIDOX) were examd. in
this study. Despite having low sequence homologies (.apprx.20%), these enzymes were found to possess conserved structural
domains (delineated as modules I and II) that fold into jelly-roll motifs, juxtaposed by adjacent stabilizing elements. The seven highly
conserved residues, corresponding to His214, Asp216 and His270 in Aspergillus nidulans IPNS (IPNS_AN) for iron binding, Arg279 and
Ser281 for substrate/co-substrate binding, as well as Gly40 and Gly254 with yet undetd. functions, are arrayed closely within these
conserved modules. Complex hydrogen bonding interactions of these conserved residues with residues found in specific α-helixes
and β-strands of the conserved core motif are apparently involved in stabilizing these structures. Although the NHIDOX enzymes
appear to share conserved active center architecture, differences in their hydrogen bonding networks were obsd., particularly those
involving the substrate/co-substrate binding ligands and the two conserved glycines. These may modulate functional versatilities,
relative sizes of the jelly-roll motifs, and the specific amino acid residues involved in stabilization and folding of the active center.
Answer 919:
flavanone
Enzymatic synthesis of novel antioxidant flavonoids by Escherichia coli cells expressing modified metabolic genes involved
in biphenyl catabolism. Shindo, Kazutoshi; Kagiyama, Yukiko; Nakamura, Ryoko; Hara, Akihiro; Ikenaga, Hiroshi; Furukawa,
Kensuke; Misawa, Norihiko. Department of Food and Nutrition, Japan Women's University, Bunkyo-ku, Tokyo, Japan. Journal
of Molecular Catalysis B: Enzymatic (2003), 23(1), 9-16. Publisher: Elsevier Science B.V., CODEN: JMCEF8 ISSN: 1381-1177.
Abstract
The bpha1(2072)A2A3A4 gene cluster codes for a modified biphenyl dioxygenase holoenzyme with broad substrate specificity. In the
previous report, we have shown the biotransformation of flavone, flavanone, 6-hydroxyflavone and 6-hydroxyflavanone by
Streptomyces lividans cells carrying bphA1(2072)A2A3A4. In the present study, we successfully biotransformed chalcone and
7-hydroxyisoflavone, which are categorized with other groups of flavonoids, by using recombinant Escherichia coli cells expressing the
same genes. We also biotransformed various flavonoids by E. coli cells expressing the bphB (dihydrodiol dehydrogenase) gene in
addn. to the bphA1(2072)A2A3A4 genes. Flavone, flavanone, 6-hydroxyflavone, 6-hydroxyflavanone, chalcone, and
7-hydroxyisoflavone, which were used as substrates, were converted with high efficiency to their corresponding diols, whose
structures were detd. by HREI-MS, 1H NMR and 13C NMR data. The antioxidative activity of these generated diol compds. was
markedly higher than that of the substrates used.
Answer 920:
Chiral stationary phases made from esters or carbamates of polysaccharides or oligosaccharides. Duval, Raphael;
Leveque, Hubert. (Chiralsep, Fr.). Fr. Demande (2003), 23 pp. CODEN: FRXXBL FR 2834227 A1 20030704 Patent written in
French. Application: FR 2001-16933 20011227. Priority: . CAN 139:78012 AN 2003:516845 CAPLUS (Copyright (C) 2008

FR 2834227 A1 20030704 FR 2001-16933 20011227
WO 2003055594 A2 20030710 WO 2002-FR4391 20021217
WO 2003055594 A3 20031224
LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NO, NZ, OM, PH, PL, PT, RO, RU, SC, SD, SE,
BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, SI, SK, TR, BF, BJ, CF,
CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG
AU 2002364659 A1 20030715 AU 2002-364659 20021217
AU 2002364659 B2 20080228
EP 1458475 A2 20040922 EP 2002-805798 20021217
TR, BG, CZ, EE, SK
JP 2005513492 T 20050512 JP 2003-556165 20021217
flavanone
CN 1617762 A 20050518 CN 2002-827629 20021217

IN 2004CN01422 A 20060210 IN 2004-CN1422 20040624
US 20050209100 A1 20050922 US 2004-876777 20040628
NO 2004003125 A 20040927 NO 2004-3125 20040721
FR 2001-16933 A 20011227
WO 2002-FR4391 W 20021217
Abstract
Chiral stationary phases for the chromatog. sepn. or concn. of org., mineral or organo-mineral enantiomers consist of an ester or
carbamate or a mixt. of esters and carbamates of polysaccharides or oligosaccharides and a solid org. or mineral support. The support
can be an org. polymer, such as polyamides, polystyrene, polyvinylalcs., polyacrylamides, polyolefins, polyvinylethers,
polyalkylvinylketones, polyalkynes, polyisocyanates, polyisonitriles, polyoxiranes, polythiiranes, polyazirdines, polyesters,
polythioesters, polyurethanes, polyureas, polysulfonamides, or phenol-formaldehyde resins. The support can be an inorg. material,
such as titania, alumina, magnesium silicate, zeolites, diatomaceous earth, clays, silicates, or phosphates. The support material has a
particle size of 1 μm to 10 mm and a pore size of 1-4000 .ANG.. The optically active material has the general formula PS-(OZ)n with
PS representing a polysaccharide or an oligosaccharide with at least 6 glycosidic units, n is 12-30000, and OZ represents OH,
-O-C(O)-NH-R, or -O-C(O)-R with R being a C1-40-alkyl, aryl, or alkylaryl group which can be substituted by hetero atoms, such as N,
S, O, P, Cl, F, Br, I, or Si. Preferably R can be Ph, tolyl, 3,5-dimethylphenyl, 4-chlorophenyl, 3,5-dichlorophenyl, or
4-tert-butylphenyl. The polysaccharides or oligosaccharides can be cellulose, amylose, starch, chitosan, α, β, or γ-cyclodextrins. The
stationary phase is prepd. by dissolving the ester or carbamate of the polysaccharide or oligosaccharide in a polar org. solvent, adding
a soln. or suspension of the support, followed by evapg. the solvent at about 100°C, and drying.
Answer 921:
Cholinesterase inhibitory constituents from Onosma hispida. Ahmad, Ijaz; Anis, Itrat; Malik, Abdul; Nawaz, Sarfraz Ahmad;
Choudhary, Muhammad Iqbal. International Centre of Chemical Sciences, HEJ Research Institute of Chemistry, University of
Karachi, Karachi, Pak. Chemical & Pharmaceutical Bulletin (2003), 51(4), 412-414. Publisher: Pharmaceutical Society of Japan,
Abstract
Hispidone, a new flavanone, has been isolated from Onosma hispida and assigned the structure
(2S)-5,2'-dihydroxy-7,4',5'-trimethoxyflavanone (1) by spectroscopic methods. In addn., (2S)-5,2'-dihydroxy-7,5'-dimethoxyflavanone
(2), benzoic acid (3), and 4-hydroxy benzoic acid (4) are also reported for the first time from this species.
Answer 922:
Molecular cloning and analysis of anthocyanin biosynthesis genes preferentially expressed in apple skin. Kim,
Sung-Hyun; Lee, Jae-Rin; Hong, Sung-Tae; Yoo, Yung-Keun; An, Gynheung; Kim, Seong-Ryong. Department of Life Science,
Sogang University, Mapo-gu, Seoul, S. Korea. Plant Science (Shannon, Ireland) (2003), 165(2), 403-413. Publisher: Elsevier
flavanone
Science Ltd., CODEN: PLSCE4 ISSN: 0168-9452. Journal written in English. CAN 139:241076 AN 2003:499086 CAPLUS
Abstract
Anthocyanin is the major color pigment in plants. In order to understand anthocyanin biosynthesis mechanism in apple, the cDNAs
encoding flavanone 3-hydroxylase (F3H), dihydroflavonol reductase (DFR), anthocyanidin synthase (ANS), and
UDP-glucose:flavonoid 3-O-glucosyltransferase (UFGT) were isolated from cDNA libraries prepd. from the skin tissues of apple (Malus
domestica Borkh. cv. Fuji). Deduced amino acid sequences of the cDNAs showed high homol. to the sequences from other plants.
Each gene is a member of a multigene family. The mRNAs of anthocyanin biosynthetic genes were detected preferentially in the skin
tissue and expression of the genes was coordinately induced by light. The transcripts were detected abundantly in the skins of
cultivars with red skin, but rarely in that of a cultivar carrying non-red fruit, suggesting that these genes have major roles in detn. of
apple skin color.
Answer 923:
Mechanistic approach to the cyclization reaction of a 2'-hydroxychalcone analogue with light and solvent. Kaneda, Kaoru;
Arai, Tatsuo. Department of Chemistry, University of Tsukuba, Ibaraki, Japan. Organic & Biomolecular Chemistry (2003),
1(12), 2041-2043. Publisher: Royal Society of Chemistry, CODEN: OBCRAK ISSN: 1477-0520. Journal written in English. CAN
Abstract
A photochem. cyclization reaction of 1-(2'-hydroxy-1'-naphthyl)-3-(1-naphthyl)-2-propen-1-one (1,1-NHC) to give a flavanone deriv.

took place in benzene, but did not take place in methanol and the controlling factor of the reaction was discussed based on laser
transient spectroscopy and product anal.
Answer 924:
Astilbin suppresses delayed-type hypersensitivity by inhibiting lymphocyte migration. Cai, Yu; Chen, Ting; Xu, Qiang.
State Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Nanjing University, Nanjing, Peop. Rep. China.
Journal of Pharmacy and Pharmacology (2003), 55(5), 691-696. Publisher: Pharmaceutical Press, CODEN: JPPMAB ISSN:
Abstract
This study examd. the effects of astilbin, a flavanone, on delayed-type hypersensitivity reactions and its mechanisms of action on
cell migration. Astilbin significantly inhibited the sheep red blood cell-induced footpad reaction and picryl-chloride-induced ear dermatitis
without affecting the organ wts., when administered during the effector phase but not the induction phase. The flavanone also
significantly inhibited the migration to gelation of spleen cells isolated from mice with ear dermatitis in a transwell system.
Furthermore, the isolated spleen cells from normal mice were incubated with astilbin in the presence of Con A, or those from mice with
ear dermatitis were cultured with astilbin. In the supernatants collected, the activity of matrix metalloproteinases (MMPs) MMP-2 and
MMP-9 was remarkably inhibited by astilbin. These results suggest that astilbin may inhibit delayed-type hypersensitivity reactions
through selectively suppressing the lymphocyte functions, including cell migration, via down-regulating MMP activity.
Answer 925:
flavanone
Molecular Quantum Similarity Analysis of Estrogenic Activity. Saliner, Ana Gallegos; Amat, Lluis; Carbo-Dorca, Ramon; Schultz,
T. Wayne; Cronin, Mark T. D. Institute of Computational Chemistry, University of Girona, Girona, Spain. Journal of Chemical
Information and Computer Sciences (2003), 43(4), 1166-1176. Publisher: American Chemical Society, CODEN: JCISD8 ISSN:
Abstract
The main objective of this study was to evaluate the capability of 120 arom. chems. to bind to the human alpha estrogen receptor
(hERα) by the use of quantum similarity methods. The exptl. data were segregated into two categories, i.e., those compds. with and
without estrogenicity activity (active and inactive). To identify potential ligands, semiquant. structure-activity relationships were
developed for the complete set correlating the presence or lack of binding affinity to the estrogen receptor with structural features of
the mols. The structure-activity relationships were based upon mol. similarity indexes, which implicitly contain information related to
changes in the electron distributions of the mols., along with indicator variables, accounting for several structural features. In addn.,
the whole set was split into several chem. classes for modeling purposes. Models were validated by dividing the complete set into
several training and test sets to allow for external predictions to be made.
Answer 926:
Comparative analysis of leaf trichome structure and composition of epicuticular flavonoids in Finnish birch species.
Valkama, Elena; Salminen, Juha-Pekka; Koricheva, Julia; Pihlaja, Kalevi. Section of Ecology, Department of Biology, University of
Turku, Turku, Finland. Annals of Botany (Oxford, United Kingdom) (2003), 91(6), 643-655. Publisher: Oxford University Press,
CODEN: ANBOA4 ISSN: 0305-7364. Journal written in English. CAN 140:73945 AN 2003:457594 CAPLUS (Copyright (C)
Abstract
The morphol., ultrastructure, d. and distribution of trichomes on leaves of Betula pendula, B. pubescens ssp. pubescens, B. pubescens
ssp. czerepanovii and B. nana were examd. by means of light, scanning and transmission electron microscopy. The compn. of
flavonoids in ethanolic leaf surface exts. was analyzed by HPLC. All taxa examd. contained both glandular and non-glandular
trichomes (short and/or long hairs) but differed from each other in trichome ultrastructure, d. and location on the leaf. Leaves of B.
pubescens were more hairy than those of B. pendula, but the latter species had a higher d. of glandular trichomes. Of the two
subspecies of B. pubescens, leaves of ssp. pubescens had more short hairs on the leaf surface and four times the d. of glandular
trichomes of leaves of ssp. czerepanovii, whereas, in the latter subspecies, short hairs occurred largely on leaf veins, as in B. nana.
The glandular trichomes were peltate glands, consisting of medullar and cortical cells, which differed structurally. Cortical cells
possessed numerous small, poorly developed plastids and small vacuoles, whereas medullar cells had several large plastids with
well-developed thylakoid systems and fewer vacuoles. In B. pubescens subspecies, vacuoles of the glandular cells contained
osmiophilic deposits, which were probably phenolic, whereas in B. pendula, vacuoles of glandular trichomes were characterized by the
presence of numerous myelin-like membranes. The compn. of epicuticular flavonoids also differed among species. The two
subspecies of B. pubescens and B. nana shared the same 12 compds., but five of these occurred only in trace amts. in B. nana.
Leaf surface exts. of B. pendula contained just six flavonoids, three of which occurred only in this species. In summary, the
structure, d. and distribution of leaf trichomes and the compn. of epicuticular flavonoids represent good taxonomic markers for Finnish
birch species.
Answer 927:
flavanone
Effects of salicylic acid on the production of procyanidin and anthocyanin in culture grape cells. Obinata, Noe; Yamakawa,
Takashi; Takamiya, Mikiko; Tanaka, Norie; Ishimaru, Kanji; Kodama, Tohru. Dep. Biotechnol., The Univ. Tokyo, Tokyo, Japan.
Plant Biotechnology (Tokyo, Japan) (2003), 20(2), 105-111. Publisher: Japanese Society for Plant Cell and Molecular Biology,
CODEN: PLBIF6 ISSN: 1342-4580. Journal written in English. CAN 139:81999 AN 2003:450918 CAPLUS (Copyright (C) 2008
Abstract
The formation of procyanidin and anthocyanin in grape cells is markedly increased by treatment with salicylic acid. The activity of
phenylalanine ammonia-lyase and chalcone-flavanone isomerase increased in close relation to the formation of these phenolics.
Salicylic acid-induced elevation of these enzyme activities occurred more rapidly than elevation induced by light irradn. In the cells,
the phenolics were degraded in a different manner by salicylic acid treatment than that by light irradn. Salicylic acid might be used as
a simple and effective stimulant for the formation of procyanidin as well as anthocyanin in large scale cultures of plant cells.
Answer 928:
Analysis and purification of flavanones, chalcones and dihydrochalcones. Tomas-Barberan, Francisco A.; Gil-Izquierdo,
Angel; Ferreres, Federico; Gil, Maria I. Departamento de Ciencia y Tecnologia de Alimentos, CEBAS (CSIC), Murcia, Spain.
Editor(s): Santos-Buelga, Celestino; Williamson, Gary. Methods in Polyphenol Analysis (2003), 359-371. Publisher: Royal
Society of Chemistry, Cambridge, UK CODEN: 69DZBQ Conference; General Review written in English. CAN 140:144804 AN
Abstract
A review discussing the detn. of flavanones, chalcones, and dihydrochalcones in plant and food anal.
Answer 929:
Acaricidal activity of Uvaria versicolor and Uvaria klaineana (Annonaceae). Akendengue, B.; Ngou-Milama, E.;
Bourobou-Bourobou, H.; Essouma, J.; Roblot, F.; Gleye, C.; Laurens, A.; Hocquemiller, R.; Loiseau, P.; Bories, C. Departement de
Chimie-Biochimie, Faculte de Medecine et des Sciences de la Sante, Libreville, Gabon. Phytotherapy Research (2003), 17(4),
364-367. Publisher: John Wiley & Sons Ltd., CODEN: PHYREH ISSN: 0951-418X. Journal written in English. CAN 139:360378
Abstract
Three Uvaria species, namely U. klaineana, U. mocoli and U. versicolor were tested in vitro against Dermatophagoides pteronyssinus,
the European house dust mite. The most active exts. were the Uvaria versicolor stems crude methanol and hexane exts. with EC50
values of 0.095 g/m2 and 0.12 g/m2, resp. The bioassay-guided fractionation of the hexane ext. led to the isolation of benzyl
benzoate which exhibited an EC50 value of 0.045 g/m2. A new flavanone, versuvanone, and the known oxoaporphine liriodenine were
also isolated from this species and showed EC50 values > 1.5 g/m2. A weak acaricidal activity (0.85 g/m2) was obsd. for the
dichloromethane ext. of Uvaria klaineana, due to the presence of benzyl benzoate. Uvaria mocoli was inactive. The structures of
compds. were elucidated using 2D-NMR techniques.
Answer 930:
flavanone
Two prenylated flavonoids from the stem bark of Erythrina burttii. Yenesew, Abiy; Irungu, Beatrice; Derese, Solomon; Midiwo,
Jacob O.; Heydenreich, Matthias; Peter, Martin G. Department of Chemistry, University of Nairobi, Nairobi, Kenya.
Phytochemistry (Elsevier) (2003), 63(4), 445-448. Publisher: Elsevier Science Ltd., CODEN: PYTCAS ISSN: 0031-9422. Journal
Abstract
From the stem bark of Erythrina burttii, a new isoflavone, 5,2',4'-trihydroxy-7-methoxy-6-(3-methylbut-2-enyl)isoflavone (trivial name,
7-O-methylluteone) and a new flavanone, 5,7-dihydroxy-4'-methoxy-3'-(3-methylbutadienyl)-5'-(3-methylbut-2-enyl)flavanone (trivial
name, burttinonedehydrate) along with three known isoflavonoids (8-prenylluteone, 3-O-methylcalopocarpin and genistein) were isolated.
The structures were detd. on the basis of spectroscopic evidence.
Answer 931:
Divergent evolution of flavonoid 2-oxoglutarate-dependent dioxygenases in parsley. Martens, Stefan; Forkmann, Gert;
Britsch, Lothar; Wellmann, Frank; Matern, Ulrich; Lukacin, Richard. Institut fuer Pharmazeutische Biologie, Philipps-Universitaet
Marburg, Marburg, Germany. FEBS Letters (2003), 544(1-3), 93-98. Publisher: Elsevier Science B.V., CODEN: FEBLAL ISSN:
Abstract
Flavone synthases (FNSs) catalyze the oxidn. of flavanones to flavones, i.e., the formation of apigenin from (2S)-naringenin. While
many plants express a microsomal-type FNS II, the sol. FNS I appears to be confined to a few species of the Apiaceae and was
cloned recently from parsley plants. FNS I belongs to the FeII/2-oxoglutarate-dependent dioxygenases characterized by short
conserved sequence elements for cofactor binding, and its evolutionary context and mode of action are under investigation. Using a
homol.-based reverse transcription polymerase chain reaction approach, two addnl. flavonoid-specific dioxygenases were cloned from
immature parsley leaflets, which were identified as flavanone 3β-hydroxylase (FHT) and flavonol synthase (FLS) after expression in
yeast cells. Sequence alignments revealed marginal differences among the parsley FNS I and FHT polypeptides of only 6%, while
much less identity (about 29%) was obsd. with the parsley FLS. Analogous to FNS I, FLS oxidizes the flavonoid γ-pyrone by
introducing a C2,C3 double bond, and (2R,3S)-dihydrokaempferol (cis-dihydrokaempferol) was proposed recently as the most likely
intermediate in both FNS I and FLS catalysis. Incubation of either FNS I or FLS with cis-dihydrokaempferol exclusively produced
kaempferol and confirmed the assumption that flavonol formation occurs via hydroxylation at C3 followed by dehydration. However,
the lack of apigenin in these incubations ruled out cis-dihydrokaempferol as a free intermediate in FNS I catalysis. Furthermore,
neither (+)-trans-dihydrokaempferol nor unnatural (-)-trans-dihydrokaempferol and 2-hydroxynaringenin served as a substrate for FNS
I. Overall, the data suggest that FNS I has evolved uniquely in some Apiaceae as a paraphyletic gene from FHT, irresp. of the fact
that FNS I and FLS catalyze equiv. desatn. reactions.
Answer 932:
Photochemical synthesis of 2,2'-biflavanones from flavone. Chen, Arh-Hwang; Kuo, Wei-Bao; Chen, Chia-Wen. Department
of Chemistry, National Kaohsiung Normal University, Kaohsiung, Taiwan. Journal of the Chinese Chemical Society (Taipei,
Taiwan) (2003), 50(1), 123-127. Publisher: Chinese Chemical Society, CODEN: JCCTAC ISSN: 0009-4536. Journal written in
flavanone
Abstract
Photolysis of flavone (4) with the electron-donating amines including triethylamine or 2-(N,N-dimethylamino)ethanol in acetonitrile,
benzene or methylene dichloride can easily afford two hydrodimers of 2,2'-biflavanone(racemate) (5a) and 2,2'-biflavanone(meso) (5b)
and one reductive product of flavanone (6). Their yields were dependent on the molar ratios of substrate to amine, the kinds of
amines, the solvents used and the irradn. sources. Higher yields were afforded 2,2'-biflavanone(racemate) (5a),
2,2'-biflavanone(meso) (5b) and flavanone (6) (30.0%, 20.9% and 15.8%, resp.) in the reaction condition of 1/2 molar ratio of flavone
(4) to triethylamine in acetontrile with fourteen hours of irradn.
Answer 933:
GC-MS analysis of chemical component of Oxytropis falcata extracted by petroleum ether. Zheng, Shang-zhen; Que, Sheng;
Xu, Xian-fang; Shen, Xu-wei. College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu,
Peop. Rep. China. Xibei Shifan Daxue Xuebao, Ziran Kexueban (2003), 39(2), 51-53. Publisher: Xibei Shifan Daxue, CODEN:
XDXKEH ISSN: 1001-988X. Journal written in Chinese. CAN 140:117508 AN 2003:400848 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
The chem. components of Oxytropis falcata from petroleum ether have been studied by the GC-MS-DC, and 57 constituents have
been identified. The major components are (z,z,z)-9, 12, 15-octadeca-trien-1-ol(14.73%),
(E)-1-(2,6-dihydroxy-4-methoxyl)-3-phenyl-2-propen-1-one (7.68%), hexadecanoic acid ethylester(6.49%), linolenic acid ethylester
(4.35%), 23,24-dihydro stigmasterol (4.30%), 2-phenyl-5,7-dihydroxy flavanone(1.93%) etc. The major components come up to
86.70%.
Answer 934:
Production of plant-specific flavanones by Escherichia coli containing an artificial gene cluster. Hwang, Eui Il; Kaneko,
Masafumi; Ohnishi, Yasuo; Horinouchi, Sueharu. Department of Biotechnology, Graduate School of Agriculture and Life Sciences,
The University of Tokyo, Tokyo, Japan. Applied and Environmental Microbiology (2003), 69(5), 2699-2706. Publisher: American
Society for Microbiology, CODEN: AEMIDF ISSN: 0099-2240. Journal written in English. CAN 139:178740 AN 2003:377628
Abstract
In plants, chalcones are precursors for a large no. of flavonoid-derived plant natural products and are converted to flavanones by
chalcone isomerase or nonenzymically. Chalcones are synthesized from tyrosine and phenylalanine via the phenylpropanoid pathway
involving phenylalanine ammonia lyase (PAL), cinnamate-4-hydroxylase (C4H), 4-coumarate:CoA ligase (4CL), and chalcone synthase
(CHS). For the purpose of prodn. of flavanones in Escherichia coli, three sets of an artificial gene cluster which contained three genes
of heterologous origins-PAL from the yeast Rhodotorula rubra, 4CL from the actinomycete Streptomyces coelicolor A3(2), and CHS
from the licorice plant Glycyrrhiza echinata-were constructed. The constructions of the three sets were done as follows: (i) PAL, 4CL,
and CHS were placed in that order under the control of the T7 promoter (PT7) and the ribosome-binding sequence (RBS) in the pET
vector, where the initiation codons of 4CL and CHS were overlapped with the termination codons of the preceding genes; (ii) the three
genes were transcribed by a single PT7 in front of PAL, and each of the three contained the RBS at appropriate positions; and (iii) all
three genes contained both PT7 and the RBS. These pathways bypassed C4H, a cytochrome P 450 hydroxylase, because the
bacterial 4CL enzyme ligated CoA to both cinnamic acid and 4-coumaric acid. E. coli cells contg. the gene clusters produced two
flavanone
flavanones, pinocembrin from phenylalanine and naringenin from tyrosine, in addn. to their precursors, cinnamic acid and 4-coumaric
acid. Of the three sets, the third gene cluster conferred on the host the highest ability to produce the flavanones. This is a new
metabolic engineering technique for the prodn. in bacteria of a variety of compds. of plant and animal origin.
Answer 935:
The compositional characterisation and antioxidant activity of fresh juices from Sicilian sweet orange (Citrus sinensis L.
Osbeck) varieties. Proteggente, Anna R.; Saija, Antonella; De Pasquale, Anna; Rice-Evans, Catherine A. Antioxidant Research
Group, Wolfson Centre for Age-Related Diseases, GKT School of Biomedical Sciences, King's College London, London, UK. Free
Radical Research (2003), 37(6), 681-687. Publisher: Taylor & Francis Ltd., CODEN: FRARER ISSN: 1071-5762. Journal written in
Abstract
Epidemiol. evidence has suggested that consumption of fruit and vegetables reduces the risk of both cancer and cardiovascular
diseases, potentially through the biol. actions of components such as vitamin C, vitamin E, flavonoids, and carotenoids. Citrus
species are extremely rich sources in vitamin C and flavanones, a class of compds. which belongs to the flavonoids family. A
comparison of the phenolic compns., the ascorbic acid contents and the antioxidant activities of fresh Sicilian orange juices from
pigmented (Moro, Tarocco and Sanguinello) and non-pigmented (Ovale, Valencia and Navel) varieties of orange (Citrus sinensis L.
Osbeck), was undertaken. The simultaneous characterization and quantification of the major flavanone, anthocyanin and
hydroxycinnamate components were attained by HPLC with diode array detection. Differences between varieties in terms of the
flavanone glycoside content, particularly hesperidin, were obsd., with the Tarocco juices reporting the highest content. Furthermore,
cyanidin-3-glucoside and cyanidin-3-(6''-malonyl)-glucoside were predominant in all the pigmented varieties, but their concn. was higher
in the juices of the Moro variety. Quant., the major antioxidant component of all juices was ascorbic acid and its concn. was
significantly correlated (r = 0.74, P < 0.001) with the total antioxidant activity of the juices, detd. in vitro using the ABTS radical cation
decolorization assay. Similarly, hydroxycinnamates (r = 0.73, P < 0.01) and anthocyanins (r = 0.98, P < 0.001) content showed a good
correlation with the detd. antioxidant capacity. Therefore orange juices, particularly those rich in anthocyanins, may represent a
significant dietary source of flavonoids.
Answer 936:
Sequence homologs of genes for enzymes of structural macromolecule biosynthesis of forage grasses and their uses in
altering forage composition. Demmer, Jeroen; Forster, Richard L.; Gibson, John Bryan; Shenk, Michael Andrew; Norriss, Michael
Geoffrey; Glenn, Matthew; Saulsbury, Keith Martin; Hall, Claire. (Genesis Research and Development Corporation Limited, N. Z.;
Wrightson Seeds Limited). PCT Int. Appl. (2003), 240 pp. CODEN: PIXXD2 WO 2003040306 A2 20030515 Designated States
W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, ES, FI, GB,
GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ,
NO, NZ, OM, PH, PL, PT, RO, RU, SC, SD, SE, SG, SI, SK, SL, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM,
ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI,
CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2002-NZ239 20021107. Priority: US 2001-337703

WO 2003040306 A2 20030515 WO 2002-NZ239 20021107
WO 2003040306 A3 20040219
flavanone
LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NO, NZ, OM, PH, PL, PT, RO, RU, SC, SD, SE,
SG, SI, SK, SL, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW
BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, SK, TR, BF, BJ, CF,
CA 2465917 A1 20030515 CA 2002-2465917 20021107
AU 2002360228 A1 20030519 AU 2002-360228 20021107
AU 2002360228 B2 20080410
EP 1451327 A2 20040901 EP 2002-795456 20021107
TR, BG, CZ, EE, SK
NZ 532712 A 20061222 NZ 2002-532712 20021107
US 2001-337703P P 20011107
WO 2002-NZ239 W 20021107
Abstract
Sequence homologs of genes for enzymes of lignin, fructan and tannin biosynthesis are identified in the forage grasses Lolium
perenne and Festuca arundinacea. The genes may be used as targets in the modulation of patterns of macromol. biosynthesis and
the nutritional compn. and value of forage grasses (no data). Candidate genes were identified in leaf and stem expression libraries by
BLAST searching against public sequence databases. Candidate genes for sucrose phosphatase, sucrose synthase, acid invertase
and peroxidase were shown to encode the enzymes by assay of gene products in Escherichia coli or Pchia pastoris. Candidate
fructosyltransferase genes were tested for their effects on fructan compn. of Nicotiana benthamiana.
Answer 937:
Naringenin inhibits phosphoinositide 3-kinase activity and glucose uptake in 3T3-L1 adipocytes. Harmon, Anne W.; Patel,
Yashomati M. Department of Nutrition, University of North Carolina School of Public Health, Chapel Hill, NC, USA.
Biochemical and Biophysical Research Communications (2003), 305(2), 229-234. Publisher: Elsevier Science, CODEN: BBRCA9
(R))
Abstract
Previous studies have shown that flavonoids inhibit glucose uptake in cultured cells. In this report, we show that the grapefruit
flavanone naringenin inhibited insulin-stimulated glucose uptake in 3T3-L1 adipocytes in a dose-dependent manner. Naringenin acts by
inhibiting the activity of phosphoinositide 3-kinase (PI3K), a key regulator of insulin-induced GLUT4 translocation. Although naringenin
did not alter the phosphotyrosine status of the insulin receptor, insulin receptor substrate proteins, or PI3K, it did inhibit the
phosphorylation of the downstream signaling mol. Akt. In an in vitro kinase assay, naringenin inhibited PI3K activity. A physiol.
attainable dose of 6 μM naringenin reduced insulin-stimulated glucose uptake by approx. 20%. This inhibitory effect remained 24 h
after the removal of naringenin from the culture medium. Collectively, our findings suggest that the regular consumption of naringenin
in grapefruit may exacerbate insulin resistance in susceptible individuals via impaired glucose uptake in adipose tissue.
flavanone
Answer 938:
Anti-sindbis activity of flavanones hesperetin and naringenin. Paredes, Adriana; Alzuru, Mariaelena; Mendez, Jeannette;
Rodriguez-Ortega, Morella. Biomedical Institute, Venezuelan Central University, Caracas, Venez. Biological & Pharmaceutical
Bulletin (2003), 26(1), 108-109. Publisher: Pharmaceutical Society of Japan, CODEN: BPBLEO ISSN: 0918-6158. Journal written
Abstract
The effect of hesperetin, naringenin and its glycoside form on the Sindbis neurovirulent strain (NSV) replication in vitro was studied.
All flavanones tested were not cytotoxic on Baby Hamster cells 21 clone 15 (BHK-21). Antiviral effect was evaluated by a
colorimetric assay using MTT (3-(4,5 dimethylthiazol-2-yl)-2,5-dipheyl-tetrazolium bromide) and by plaque redn. assay. Hesperetin and
naringenin had inhibitory activity on NSV infection. The 50% inhibitory doses (ID50%) of both compds. were 20.5 and 14.9 μg/mL
resp., as established by plaque assay. However their glycosides, hesperidin and naringin did not have inhibitory activity. Implying
that the presence of rutinose moiety of flavanones blocks the antiviral effect. Oxygenation on the 3' positions at the B rings on the
hesperetin skeleton decrease the anti viral activity at 25 μg/mL.
Answer 939:
O-demethylation and sulfation of 7-methoxylated flavanones by Cunninghamella elegans. Abdel-Rahim, Sayed Ibrahim;
Galal, Ahmed Mohamed; Ahmed, Mohammed Shamim; Mossa, Gabir Salem. Pharmacognosy Department, College of Pharmacy,
Tanta University, Tanta, Egypt. Chemical & Pharmaceutical Bulletin (2003), 51(2), 203-206. Publisher: Pharmaceutical Society of
Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN 140:4098 AN 2003:355011 CAPLUS (Copyright
Abstract
Metab. of 7-O-methylnaringenin (sakuranetin, I) by Cunninghamella elegans NRRL 1392 yielded naringenin and naringenin-4'-sulfate.
C. elegans also converted 5,3',4'-trihydroxy-7-methoxyflavanone (7-methyleriodictyol, II) into eriodictyol-4'-sulfate. Furthermore,
incubation of 5,4'-dihydroxy-7,3'-dimethoxyflavanone (III) with the same fungus gave homoeriodictyol
(5,7,4'-trihydroxy-3'-methoxyflavanone) and homoeriodicytol-7-sulfate. The structures of the new metabolites were established by
spectral anal. including 2D-NMR, HR-ESI-FT-MS beside hydrolysis by acid.
flavanone
OH
Me O O
OH O I
OH
OH
Me O O
OH O II
OMe
OH
Me O O
OH O III
Answer 940:
Activity-guided isolation of the chemical constituents of Muntingia calabura using a quinone reductase induction assay.
Su, Bao-Ning; Park, Eun Jung; Vigo, Jose Schunke; Graham, James G.; Cabieses, Fernando; Fong, Harry H. S.; Pezzuto, John M.;
Kinghorn, A. Douglas. College of Pharmacy, Program for Collaborative Research in the Pharmaceutical Sciences and Department of
Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, Chicago, IL, USA. Phytochemistry (Elsevier) (2003),
63(3), 335-341. Publisher: Elsevier Science Ltd., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN
Abstract
Activity-guided fractionation of an EtOAc-sol. ext. of the leaves of Muntingia calabura collected in Peru, using an in vitro quinone
reductase induction assay with cultured Hepa 1c1c7 (mouse hepatoma) cells, resulted in the isolation of a flavanone with an
unsubstituted B-ring, (2R,3R)-7-methoxy-3,5,8-trihydroxyflavanone, as well as 14 known compds., which were mainly flavanones and
flavanone
flavones. The structure including abs. stereochem. of compd. 5 was detd. by spectroscopic (HRMS, 1D and 2D NMR, and CD
spectra) methods. Of the isolates obtained, in addn. to 5, (2S)-5-hydroxy-7-methoxyflavanone, 2',4'-dihydroxychalcone,
4,2',4'-trihydroxychalcone, 7-hydroxyisoflavone and 7,3',4'-trimethoxyisoflavone were found to induce quinone reductase activity.
Answer 941:
Flavones and flavanones from South American Cunila species. de Loreto Bordignon, S. A.; Montanha, J. A.; Schenkel, E. P.
Curso de Biologia, Universidade Luterana do Brasil, Canoas, Brazil. Biochemical Systematics and Ecology (2003), 31(7),
785-788. Publisher: Elsevier Science Ltd., CODEN: BSECBU ISSN: 0305-1978. Journal written in English. CAN 140:38766 AN
Abstract
Several flavones and flavanones were isolated from chloroform extd. air-dried South American Cunila species. The flavonoid
aglycons accumulation was obsd. mainly in C. incana, C. angustifolia and C. incisa.
Answer 942:
New spectral data of some flavonoids from Deguelia hatschbachii A.M.G. Azevedo. Magalhaes, Aderbal F.; Tozzi, Ana M. G.
A.; Magalhaes, Eva G.; Moraes, Valeria R. de S. Instituto de Quimica, Universidade Estadual de Campinas, CP 6154, Campinas -
SP, Brazil. Journal of the Brazilian Chemical Society (2003), 14(1), 133-137. Publisher: Sociedade Brasileira de Quimica, CODEN:
JOCSET ISSN: 0103-5053. Journal written in English. CAN 139:130617 AN 2003:325780 CAPLUS (Copyright (C) 2008 ACS
on SciFinder (R))
Abstract
From the roots of Deguelia hatschbachii, the known flavonoids scandenin (I), Me robustate (II) and
4',5-dihydroxy-6-(3,3-dimethylalyll)-7-methoxy flavanone (III) were isolated and characterized by comparison of their spectroscopic
data with those found in the literature. Now the inclusion of 1D- and 2D-NMR and MS/MS data has allowed the complete assignment of
all hydrogen and carbon chem. shifts in their NMR spectra, as well as the elucidation of the fragmentation pathways of I-III in the
mass spectrometer.
Answer 943:
Dihydrochalcones: Evaluation as Novel Radical Scavenging Antioxidants. Nakamura, Yoshimasa; Watanabe, Shigeo; Miyake,
Nobuyuki; Kohno, Hiroyuki; Osawa, Toshihiko. Laboratory of Food and Biodynamics Graduate School of Bioagricultural Sciences,
Nagoya University, Nagoya, Japan. Journal of Agricultural and Food Chemistry (2003), 51(11), 3309-3312. Publisher: American
Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 139:30718 AN 2003:322574 CAPLUS
Abstract
Dihydrochalcones are a family of bicyclic flavonoids, defined by the presence of two benzene rings joined by a satd. three carbon
flavanone
bridge. In the present study, the authors systematically examd. the antioxidant activities of dihydrochalcones against the stable free
radical (1,1-diphenyl-2-picrylhydrazyl) and lipid peroxidn. in the erythrocyte membrane. All dihydrochalcones exhibited higher
antioxidant activities than the corresponding flavanones. The 1H NMR anal. indicated that the active dihydrochalcone has a
time-averaged conformation in which the arom. A ring is orthogonal to the carbonyl group, while the inactive dihydrochalcone such as
2'-O-methyl-phloretin has a strongly hydrogen-bonded phenolic hydroxyl group, suggestive of a coplanar conformation. A hydroxyl
group at the 2'-position of the dihydrochalcone A ring, newly formed by redn. of the flavanone C ring, is an essential pharmacophore
for its radical scavenging potential. The results are discussed in relation to the use of dihydrochalcones as pharmaceuticals and food
additives.
Answer 944:
The effect of solvents on the heterogeneous synthesis of flavanone over MgO. Drexler, Michele T.; Amiridis, Michael D.
Department of Chemical Engineering, University of South Carolina, Columbia, SC, USA. Journal of Catalysis (2003), 214(1),
136-145. Publisher: Elsevier Science, CODEN: JCTLA5 ISSN: 0021-9517. Journal written in English. CAN 139:68822 AN
Abstract
The effect of several solvents on the heterogeneous synthesis of flavanone from benzaldehyde and 2-hydroxyacetophenone over a
solid MgO catalyst was examd. exptl. through kinetic and FTIR spectroscopic studies. High-boiling-point solvents considered were
DMSO, tetralin, mesitylene, benzonitrile, and nitrobenzene. Kinetic results indicate that the presence of different solvents in this
reaction system affects the rate, kinetic dependencies, and selectivities toward flavanone and 2'-hydroxychalcone. DMSO in
particular, significantly promotes the rates of both steps used in this synthesis (i.e., the Claisen-Schmidt condensation reaction of
benzaldehyde with 2-hydroxyacetophenone and the subsequent isomerization of the 2'-hydroxychalcone intermediate to flavanone).
The effect is more pronounced for the second reaction. Even the presence of small amts. of DMSO in other solvents, such as
benzonitrile and nitrobenzene, results in strong promotion of the flavanone synthesis scheme. Results of FTIR spectroscopic studies
indicate that the interaction of MgO with DMSO gave stable surface sulfate species. The presence of these species on the catalyst
surface affects the adsorption behavior of benzaldehyde and 2-hydroxyacetophenone.
Answer 945:
Synthesis of 3,5 diaryl-4-aroyl-1-benzoyl-Δ2-pyrazolines. Jaware, Miss K. N.; Ganorkar, Rajesh P.; Jamode, V. S. Department
of Chemistry, Amravati University, Amravati, India. Asian Journal of Chemistry (2003), 15(2), 833-836. Publisher: Asian
Journal of Chemistry, CODEN: AJCHEW ISSN: 0970-7077. Journal written in English. CAN 139:214382 AN 2003:310744
Abstract
Some new 3,5-diaryl-4-aroyl-1-benzoyl-Δ2-pyrazolines were synthesized by the action of benzhydrazide on 3-aroyl flavanones in
pyridine medium. Structure of these compds. was established on the basis of spectral anal. and elemental anal.
Answer 946:
Genes encoding flavonoid biosynthesis enzymes in white clover and perennial ryegrass and their use in genetic
flavanone
manipulation of flavonoid biosynthesis in plants. Spangenberg, German; Sawbridge, Timothy Ivor; Ong, Eng Kok; Emmerling,
Michael. (Agriculture Victoria Services Pty. Ltd., Australia; Agresearch Limited). PCT Int. Appl. (2003), 732 pp. CODEN: PIXXD2
WO 2003031622 A1 20030417 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN, CO,
CR, CU, CZ, DE, DK, DM, DZ, EC, EE, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR,
LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NO, NZ, OM, PH, PL, PT, RO, RU, SD, SE, SG, SI, SK, SL, TJ, TM, TN, TR, TT,
TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU,
MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO
2002-AU1345 20021004. Priority: AU 2001-8113 20011005. CAN 138:298914 AN 2003:301224 CAPLUS (Copyright (C) 2008

WO 2003031622 A1 20030417 WO 2002-AU1345 20021004
LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NO, NZ, OM, PH, PL, PT, RO, RU, SD, SE, SG, SI,
SK, SL, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW
BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, SK, TR, BF, BJ, CF,
CA 2461058 A1 20030417 CA 2002-2461058 20021004
AU 2002333038 A1 20030422 AU 2002-333038 20021004
AU 2002333038 B2 20080207
EP 1442122 A1 20040804 EP 2002-800506 20021004
TR, BG, CZ, EE, SK
NZ 531985 A 20060127 NZ 2002-531985 20021004
US 20050069884 A1 20050331 US 2004-491823 20041025
AU 2001-8113 A 20011005
WO 2002-AU1345 W 20021004
Abstract
The present invention relates to nucleic acids and nucleic acid fragments encoding amino acid sequences for flavonoid biosynthetic
enzymes in plants, and the use thereof for the modification of flavonoid biosynthesis in plants. More particularly, the flavonoid
biosynthetic enzyme is selected from the group consisting of chalcone isomerase, chalcone synthase, chalcone reductase,
dihydroflavonol 4-reductase, leucoanthocyanidin reductase, flavonoid 3',5'-hydrolase, flavanone 3-hydroxylase, flavonoid
3'-hydroxylase, phenylalanine ammonia-lyase, and vestitone reductase, found in white clover (Trifolium repens) and perennial ryegrass
(Lolium perenne).
Answer 947:
flavanone
Study of the thermal stability and biological activity of phenacyl N,N-dialkyl dithiocarbamates and the corresponding
flavanones. Finaru, Adriana; Grosu, Mirela; Prisecaru, Maria; Segal, Eugen. Universite De Bacau, Laboratoire de Synthese
Organique et Analyse Structurale, Bacau, Rom. Studii si Cercetari Stiintifice: Chimie si Inginerie Chimica, Biotehnologii, Industrie
Alimentara (Universitatea Bacau) (2002), 3(1-2), 65-70. Publisher: University of Bacau, Dep. of Chemistry and Food Science &
Technology, CODEN: SCSCC6 ISSN: 1582-540X. Journal written in French. CAN 140:37366 AN 2003:265355 CAPLUS
Abstract
Thermal stability and biol. activity of some N,N-dialkyl dithiocarbamates (I) and corresponding flavanones (II) were evaluated. The
biol. activity tests were conducted on wheat (Triticum aestivum) and a medicinal plant Stachys sieboldii, as well as on several species
of bacteria. Several compds. showed germination and plant growth inhibiting and/or stimulating activities at different concns., as well
as antibacterial properties.
Bu S
Br CO CH S C NR 1 R 2
HO OH
Br I
O
Bu
Br R1
HO O Ph
Br II
Answer 948:
Flavonoids, phenolic acids and abscisic acid in Australian and New Zealand Leptospermum honeys. Yao, Lihu; Datta,
Nivedita; Tomas-Barberan, Francisco A.; Ferreres, Federico; Martos, Isabel; Singanusong, Riantong. School of Land and Food
Sciences, Food Science and Technology, The University of Queensland, Gatton, Australia. Food Chemistry (2003), 81(2),
159-168. Publisher: Elsevier Science Ltd., CODEN: FOCHDJ ISSN: 0308-8146. Journal written in English. CAN 138:320239 AN
Abstract
Flavonoids, phenolic acids and abscisic acid of Australian and New Zealand Leptospermum honeys were analyzed by HPLC. Fifteen
flavonoids were isolated in Australian jelly bush honey (Leptospermum polygalifolium), with an av. content of 2.22 mg/100 g honey.
Myricetin (3,5,7,3',4',5'-hexahydroxyflavone), luteolin (5,7,3',4'-tetrahydroxyflavone) and tricetin (5,7,3',4',5'-pentahydroxyflavone)
were the main flavonoids identified. The mean content of total phenolic acids in jelly bush honey was 5.14 mg/100 g honey, with gallic
and coumaric acids as the potential phenolic acids. Abscisic acid was quantified as twice the amt. (11.6 mg/100 g honey) of the
phenolic acids in this honey. The flavonoid profile mainly consisted of quercetin (3,5,7,3',4'-pentahydroxyflavone), isorhamnetin
flavanone
(3,5,7,4'-tetrahydroxyflavone 3'-Me ethyl), chrysin (5,7-dihydroxyflavone), luteolin and an unknown flavanone in New Zealand manuka
(Leptospermum scoparium) honey with an av. content of total flavonoids of 3.06 mg/100 g honey. The content of total phenolic acids
was up to 14.0 mg/100 g honey, with gallic acid as the main component. A substantial quantity (32.8 mg/100 g honey) of abscisic acid
was present in manuka honey. These results showed that flavonoids and phenolic acids could be used for authenticating honey floral
origins, and abscisic acid may aid in this authentication.
Answer 949:
Influence of Industrial Processing on Orange Juice Flavanone Solubility and Transformation to Chalcones under
Gastrointestinal Conditions. Gil-Izquierdo, Angel; Gil, Maria Isabel; Tomas-Barberan, Francisco Abraham; Ferreres, Federico.
Research Group on Quality, Safety and Bioactivity of Plant Foods, Departamento Ciencia y Tecnologia de Alimentos, CEBAS-CSIC,
Murcia, Spain. Journal of Agricultural and Food Chemistry (2003), 51(10), 3024-3028. Publisher: American Chemical Society,
CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 139:6032 AN 2003:263862 CAPLUS (Copyright (C) 2008
Abstract
Orange juice manufd. on an industrial scale was subjected to digestion under in vitro gastrointestinal conditions (pH, temp., and
enzyme and chem. conditions) to evaluate the influence of individual industrial processing treatments on flavanone soly., stability, and
ability to permeate through a membrane under simulated physiol. conditions. Four industrial processes including squeezing, std.
pasteurization, concn., and freezing were evaluated. Hand squeezing was compared with industrial squeezing. After in vitro
gastrointestinal digestion of the orange juices, the flavanones able to permeate through a dialysis membrane, and those remaining in
the retentate were evaluated by HPLC as were those present in the insol. fraction. In all of the assayed orange juices, a high content
of pptd. chalcones (≈70% of the total flavanones) was formed under the physiol. conditions of the gastrointestinal tract. Hand
squeezing provided a higher concn. of flavanones in the permeated fraction and lower transformation to chalcones than industrial
squeezing. Std. pasteurization did not influence the soly. and permeability of the orange juice flavanones and chalcones. Industrial
concn. did not affect the amt. of flavanones able to permeate but decreased the chalcones produced. Juices produced from frozen
orange juice contained considerably smaller amts. of both sol. flavanones and insol. chalcones.
Answer 950:
Induction of pathogen resistance in pear by transiently altering the flavonoid metabolism with specific enzyme inhibitors.
Stich, K.; Halbwirth, H.; Kampan, W.; Treutter, D.; Rommelt, S.; Peterek, S.; Forkmann, G.; Fisher, T. C.; Martens, S.; Meisel, B.;
Costa, G.; Andreotti, C.; Sabatini, E.; Bazzi, C.; Rademacher, W. Institute of Applied Botany, Technical University of Vienna,
Austria. Acta Horticulturae (2002), 596(Vol. 1, Proceedings of the VIIIth International Symposium on Pear, 2000, Volume 1),
513-521. Publisher: International Society for Horticultural Science, CODEN: AHORA2 ISSN: 0567-7572. Journal written in English.
Abstract
The main objective of this EU project is the study of natural defense mechanisms of pome fruit against fire blight, a disease of
relevant importance in several rosaceous species all over the world and quite recently in Italy. The recent outbreaks of the disease in
Italy as well as the situation in other European countries justify the attention given by several research institutions to face this
disease. A multidisciplinary approach was chosen to achieve the objective of the project including horticultural, bacteriol., biochem.,
and mol. biol. methods. The goals partially achieved by the project partners concern the availability of dioxygenase inhibitors, of plant
material susceptible and tolerant to Erwinia amylovora to test, of preliminary results of practical applications on pome fruit species and
varieties and the involvement of some flavonoids involved in defense reactions vs. Erwinia amylovora. The most significant results
flavanone
obtained up to now are presented here.
Answer 951:
Structural Requirements of Flavonoids for Nitric Oxide Production Inhibitory Activity and Mechanism of Action. Matsuda,
Hisashi; Morikawa, Toshio; Ando, Shin; Toguchida, Iwao; Yoshikawa, Masayuki. Kyoto Pharmaceutical University, Yamashina-ku,
Kyoto, Japan. Bioorganic & Medicinal Chemistry (2003), 11(9), 1995-2000. Publisher: Elsevier Science Ltd., CODEN: BMECEP
SciFinder (R))
Abstract
To clarify the structure-activity relationships of flavonoids for nitric oxide (NO) prodn. inhibitory activity, we examd. the inhibitory
effects of 73 flavonoids on NO prodn. in lipopolysaccharide-activated mouse peritoneal macrophages. Among those flavonoids,
apigenin (IC50=7.7 μM), diosmetin (8.9 μM), and tetra-O-methylluteolin (2.4 μM), and hexa-O-methylmyricetin (7.4 μM) were found to
show potent inhibitory activity, and the results suggested the following structural requirements of flavonoids: (1) the activities of
flavones were stronger than those of corresponding flavonols; (2) the glycoside moiety reduced the activity; (3) the activities of
flavones were stronger than those of corresponding flavanones; (4) the flavones and flavonols having the 4'-hydroxyl group showed
stronger activities than those lacking the hydroxyl group at the B ring and having the 3',4'-dihydroxyl group; (5) the flavonols having
the 3',4'-dihydroxyl group (catechol type) showed stronger activities than those having the 3',4',5'-trihydroxyl group (pyrogallol type);
(6) the 5-hydroxyl group tended to enhance the activity; (7) methylation of the 3-, 5-, or 4'-hydroxyl group enhanced the activity; (8)
the activities of isoflavones were weaker than those of corresponding flavones; (9) methylation of the 3-hydroxyl group reduced the
cytotoxicity. In addn., potent NO prodn. inhibitors were found to inhibit induction of inducible nitric oxide synthase (iNOS) without iNOS
enzymic inhibitory activity.
Answer 952:
Biochemical formation of anthocyanins in silk tissue of Zea mays. Halbwirth, Heidrun; Martens, Stefan; Wienand, Udo;
Forkmann, Gert; Stich, Karl. Institute for Technical BioScience, Technical University of Vienna, Vienna, Austria. Plant Science
(Shannon, Ireland) (2003), 164(4), 489-495. Publisher: Elsevier Science Ireland Ltd., CODEN: PLSCE4 ISSN: 0168-9452. Journal
Abstract
Two types of anthocyanins are formed in tissues of Zea mays (maize), the common 3-hydroxyanthocyanins and the rare
3-deoxyanthocyanins. Their formation is generally controlled by independent regulatory genes. Whereas the formation of
3-hydroxyanthocyanins is well established, the enzymes involved in the biosynthesis of the 3-deoxyanthocyanins remained unclear
for a long time. In order to elucidate the key reaction involved, the redn. of flavanones to flavan 4-ols, dihydroflavonol 4-reductase
(DFR) and flavanone 4-reductase (FNR) activities were investigated using enzyme prepns. from silks of different maize lines as well
as from transgenic petunia and yeast, resp., expressing the A1 gene of maize. This gene is known to encode DFR. DFR and FNR
activities could not be sepd. by biochem. investigations and the use of different enzyme inhibitors. In maize genotypes with recessive
alleles (a1a1) of the A1 gene, neither DFR nor FNR activity was present. Moreover, heterologous expression of A1 in petunia and
yeast has shown that the gene encodes for a reductase, which is able to convert both dihydroflavonols (DFR activity) and flavanones
(FNR activity) to flavan 3,4-diols and flavan 4-ols, resp. Thus, DFR and FNR activities are provided by one and the same enzyme
with a broad substrate acceptance, which even includes the 5-deoxydihydroflavonols. Further studies suggested that the anthocyanin
type formed in the silks essentially depends on the strength of flavanone 3-hydroxylase activity.
Answer 953:
flavanone
Novel detection of formylated phloroglucinol compounds (FPCs) in the wound wood of Eucalyptus globulus and E. nitens.
Eyles, Alieta; Davies, Noel W.; Mohammed, Caroline. Co-Operative Research Centre for Sustainable Production Forestry,
Tasmania, Australia. Journal of Chemical Ecology (2003), 29(4), 881-898. Publisher: Kluwer Academic/Plenum Publishers,
CODEN: JCECD8 ISSN: 0098-0331. Journal written in English. CAN 139:130728 AN 2003:239081 CAPLUS (Copyright (C)
Abstract
This study characterized the chem. responses of Eucalyptus globulus and Eucalyptus nitens to artificial inoculation with a
basidiomycete decay fungus. Nine-year-old trees responded to mech. wounding or inoculation with the decay fungus by producing
new wound wood characterized by the presence of dark extractives 17 mo after wounding. Anal. of crude wound wood exts. by HPLC
coupled to neg. ion electrospray mass spectrometry revealed the presence of a complex mixt. of many unidentified formylated
phloroglucinol compds. (FPCs), in addn. to a diverse range of other polyphenolic compds. (hydrolyzable tannins, proanthocyanidins,
flavanone glycoside, stilbene glycosides). Prior to this study, FPCs have only been reported from leaves and buds of Eucalyptus
spp. Unequivocal evidence for the presence of macrocarpal A and B, and sideroxylonal A and B in the crude exts. was obtained, as
well as evidence for a wide range of as yet unreported FPCs. Subsequent preliminary in vitro fungal and bacterial bioassays did not
support an antimicrobial role for FPCs in host-pathogen interactions in eucalypts.
Answer 954:
Molecular cloning, substrate specificity of the functionally expressed dihydroflavonol 4-reductases from Malus domestica
and Pyrus communis cultivars and the consequences for flavonoid metabolism. Fischer, Thilo C.; Halbwirth, Heidrun; Meisel,
Barbara; Stich, Karl; Forkmann, Gert. TUM Weihenstephan, Freising, Germany. Archives of Biochemistry and Biophysics
(2003), 412(2), 223-230. Publisher: Elsevier Science, CODEN: ABBIA4 ISSN: 0003-9861. Journal written in English. CAN
Abstract
Treatment with the dioxygenase inhibitor prohexadione-Ca leads to major changes in the flavonoid metab. of apple (Malus domestica)
and pear (Pyrus communis) leaves. Accumulation of unusual 3-deoxyflavonoids is obsd., which have been linked to an enhanced
resistance toward fire blight. The committed step in this pathway is the redn. of flavanones. Crude exts. from leaves are able to
perform this reaction. There was previous evidence that DFR enzymes of certain plants possess addnl. flavanone 4-reductase (FNR)
activity. Such an FNR activity of DFR enzymes is proved here by heterologous expression of the enzymes. The heterologously
expressed DFR/FNR enzymes of Malus and Pyrus possess distinct differences in substrate specificities despite only minor
differences of the amino acid sequences. Kinetic studies showed that dihydroflavonols generally are the preferred substrates.
However, with the obsd. substrate specificities the occurrence of 3-deoxyflavonoids in vivo after application of prohexadione-Ca can
be explained.
Answer 955:
Anastatins A and B, new skeletal flavonoids with hepatoprotective activities from the desert plant Anastatica hierochuntica.
Yoshikawa, Masayuki; Xu, Fengming; Morikawa, Toshio; Ninomiya, Kiyofumi; Matsuda, Hisashi. Kyoto Pharmaceutical University,
Yamashina-ku, Kyoto, Japan. Bioorganic & Medicinal Chemistry Letters (2003), 13(6), 1045-1049. Publisher: Elsevier Science
flavanone
B.V., CODEN: BMCLE8 ISSN: 0960-894X. Journal written in English. CAN 139:154654 AN 2003:215763 CAPLUS (Copyright
Abstract
New skeletal flavonoids, anastatins A and B, were isolated from the methanolic ext. of an Egyptian medicinal herb, the whole plants of
Anastatica hierochuntica. Their flavanone structures having a benzofuran moiety were detd. on the basis of chem. and physicochem.
evidence. Anastatins A and B were found to show hepatoprotective effects on D-galactosamine-induced cytotoxicity in primary
cultured mouse hepatocytes and their activities were stronger than those of related flavonoids and com. silybin.
Answer 956:
Muscanone: a 3-O-(1'',8'',14''-trimethylhexadecanyl)naringenin from Commiphora wightii. Fatope, Majekodunmi O.;

Al-Burtomani, Suad Khamis S.; Ochei, John O.; Abdulnour, Abdulrahman O.; Al-Kindy, Salma M. Z.; Takeda, Yoshio. College of
Science, Department of Chemistry, Sultan Qaboos University, Muscat, Oman. Phytochemistry (Elsevier) (2003), 62(8),
1251-1255. Publisher: Elsevier Science Ltd., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 139:82015
Abstract
A new antifungal flavanone, muscanone (1), was isolated along with known naringenin (2) from Commiphora wightii (Arn.) Bhandari
(Burseraceae) by directing the fractionation of an EtOH ext. of the air-dried trunk of C. wightii with microbial sensitivity assay. The
structures of 1 and 2 were detd. from EIMS, HREIMS, DEPT, 1H-1H COSY, HSQC and HMBC spectral data. Muscanone (1) was
identified as 3-O-(1'',8'',14''-trimethylhexadecanyl)naringenin and was found to be active against Candida albicans. The isolation,
structure elucidation, NMR spectral assignments, and bioactivities of 1 and 2 are reported.
Answer 957:
Synthesis of 5,7-dihydroxy-6,8-diprenyl-4'-O-prenylflavanone. Hossain, M. Amzad. Chemistry Division, Atomic Energy

Centre, Dhaka, Bangladesh. Bangladesh Journal of Scientific and Industrial Research (1999), 34(3-4), 466-470. Publisher:
Bangladesh Council of Scientific and Industrial Research, CODEN: BJSIBL ISSN: 0304-9809. Journal written in English. CAN
Abstract
The title flavanone deriv. was prepd. from phloroacetophenone in a multistep synthesis. All the products were characterized using
spectral data and microanal.
Answer 958:
Reversed-phase HPLC determination of mangiferin, isomangiferin and hesperidin in Cyclopia and the effect of harvesting
date on the phenolic composition of C. genistoides. Joubert, Elizabeth; Otto, Frank; Gruener, Sabine; Weinreich, Bernd. ARC
Infruitec-Nietvoorbij, The Fruit Vine and Wine Institute of the Agricultural Research Council, Stellenbosch, S. Afr. European Food
flavanone
Research and Technology (2003), 216(3), 270-273. Publisher: Springer-Verlag, CODEN: EFRTFO ISSN: 1438-2377. Journal
Abstract
A reversed-phase HPLC method for sepn. of polyphenols in honeybush tea (Cyclopia spp.) is presented. Sepn. of eriodictyol, luteolin,
medicagol, formononetin, mangiferin, isomangiferin, hesperetin and hesperidin was investigated. A C12 stationary phase was required
to sep. mangiferin and isomangiferin. The method was used to quantify the 3 major polyphenols (mangiferin, isomangiferin and
hesperidin) in C. genistoides, C. intermedia, C. maculata and C. sessiliflora and to study the effect of harvesting date on these
compds. in 2 types of C. genistoides. The highest levels of the xanthones, mangiferin (3.61 g/100 g) and isomangiferin (0.54 g/100 g),
and the flavanone, hesperidin (1.74 g/100 g), were found for C. genistoides (both xanthones) and C. intermedia, resp. Cyclopia
sessiliflora contained the lowest levels of mangiferin (1.04 g/100 g) and hesperidin (0.29 g/100 g). The mangiferin content of both the
Overberg and West Coast types decreased with harvesting date. The Overberg type contained more mangiferin, but hesperidin was
more prominent in the West Coast type.
Answer 959:
Inhibition of [3H]-LSD Binding to 5-HT7 Receptors by Flavonoids from Scutellaria lateriflora. Gafner, Stefan; Bergeron,
Chantal; Batcha, Laura L.; Reich, Jesse; Arnason, John T.; Burdette, Joanna E.; Pezzuto, John M.; Angerhofer, Cindy K. Tom's of
Maine, Kennebunk, ME, USA. Journal of Natural Products (2003), 66(4), 535-537. Publisher: American Chemical Society,
CODEN: JNPRDF ISSN: 0163-3864. Journal written in English. CAN 138:348628 AN 2003:199720 CAPLUS (Copyright (C)
Abstract
The hot water and 70% ethanol exts. of dried mad-dog skullcap (Scutellaria lateriflora) both bound to the 5-HT7 receptor, with 87.2±6.2%
and 56.7±1.3% inhibition of [3H]-LSD binding to the receptor at 100 μg/mL, resp. The online anal. of a 70% ethanol ext. by
HPLC-UV/MS resulted in the identification of five flavones. Fractionation of the ethanol ext. resulted in the isolation of three
flavone-glucuronides and a flavanone-glucuronide (9), including one new compd., lateriflorin
(5,6,-dihydroxy-7-glucuronyloxy-2'-methoxyflavone) (8). The structure of 8 was detd. by NMR (1H NMR, 13C NMR, and NOESY
expts.) and MS anal. From the results obtained in the testing of the pure compds., it is evident that the activity on the 5-HT7 receptor
is at least partly due to the presence of flavonoids. Scutellarin and ikonnikoside I showed the highest inhibition of [3H]-LSD binding
with IC50 values of 63.4 and 135.1 μM, resp.
Answer 960:
Utilization of citrus by-products to improve human health. Raman, Girija; Ananthkrishnan, S.; Poulose, Shibu; Patil,
Bhimanagouda S. Citrus Center, Texas A&M University-Kingsville, Weslaco, TX, USA. Abstracts of Papers, 225th ACS National
Meeting, New Orleans, LA, United States, March 23-27, 2003 (2003), AGFD-108. Publisher: American Chemical Society,
Washington, D. C CODEN: 69DSA4 Conference; Meeting Abstract written in English. AN 2003:178621 CAPLUS (Copyright (C)
Abstract
Citrus limonoid and flavonone glucosides demonstrated potential benefits to reduce risks of cancer and cardiovascular diseases.
Citrus molasses obtained from waste residue has been used for animal feed. Since large concn. of glucosides of limonoid and
flavanone
flavonone are present in citrus byproducts, our goal was to isolate functional components from byproducts of citrus for potential health
promoting properties. Due to the structural similarity of the glucosides of flavonone and limonoids, isolation of the pure glucosides
from the mixt. was tedious. A rapid sepn. technique using a combination of adsorption chromatog. and flash chromatog. was designed
to isolate these compds. from the mixt. of glucosides. The citrus molasses was de-pectinised and passed through ion-exchange resins
to obtain an ext. rich in glucosides. This enriched ext. was agitated under cold conditions to sep. the glucosides, which are present in
max. concn. The freeze-dried ext. was further sepd. using flash chromatog. technique. A small four-step gradient method using
acetonitrile and water as mobile phase was developed. Structurally similar glucosides may be sepd. to the extent of 85%. This
system can be used as a rapid technique for sepn. of closely related limonoid and flavanone glucosides. This isolation technique
would be useful to isolate and purify the minor fractions of functional components in a larger quantity. Furthermore, larger quantity of
minor fraction would be useful to establish structural relation with biol. activity.
Answer 961:
Structure-activity relationship study of a diverse set of estrogen receptor ligands (I) using MultiCASE expert system.
Klopman, Gilles; Chakravarti, Suman K. Department of Chemistry, Case Western Reserve University, Cleveland, OH, USA.
Chemosphere (2003), 51(6), 445-459. Publisher: Elsevier Science Ltd., CODEN: CMSHAF ISSN: 0045-6535. Journal written in
Abstract
The MultiCASE expert system was used to construct a quant. structure-activity relationship model to screen chems. with estrogen
receptor (ER) binding potential. Structures and ER binding data of 313 chems. were used as inputs to train the expert system. The
training data set covers inactive, weak as well as very powerful ER binders and represents a variety of chem. compds. Substructural
features assocd. with ER binding activity (biophores) and features that prevent receptor binding (biophobes) were identified. Although
a single phenolic hydroxyl group was found to be the most important biophore responsible for the estrogenic activity of most of the
chems., MultiCASE also identified other biophores and structural features that modulate the activity of the chems. Furthermore, the
findings supported the authors' previous hypothesis that a 6 A distant descriptor may describe a ligand-binding site on an ER. Quant.
structure-activity relationship models for the chems. assocd. with each biophore were constructed as part of the expert system and
can be used to predict the activity of new chems. The model was cross validated via 10×10%-off tests, giving an av. concordance of
84.04%.
Answer 962:
Effect of t-flavanone on hair growth. Hotta, Mitsuyuki; Imokawa, Genji. Biological Science Laboratories, Kao Corporation,
Tochigi, Japan. Fragrance Journal (2003), 31(2), 33-40. Publisher: Fureguransu Janaru Sha, CODEN: FUJAD7 ISSN: 0288-9803.
Journal; General Review written in Japanese. CAN 138:390502 AN 2003:163783 CAPLUS (Copyright (C) 2008 ACS on
SciFinder (R))
Abstract
A review on identification of hair growth-promoting astilbin from Hypericum perforatum, structure-activity relationship of astilbin,
synthesis and hair growth promoting effect of astilbin analog trans-3,4-dimethyl-3-hydroxyflavanone (t-flavanone), and application of
t-flavanone-contg. hair prepns. to androgenetic alopecia.
Answer 963:

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19 May 2008 SciFinder Scholar Page: 1

Research Topic task started on Mon May 19, 2008 at 12:07 PM

2 Research Topic candidates were identified in CAPLUS and MEDLINE.

using the phrase "flavanone"

Selected 1 of 2 candidate topics.

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