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Volume 7. Issue 7. Pages 815-970.

2012
ISSN 1934-578X (printed); ISSN 1555-9475 (online)
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NPC Natural Product Communications
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2012
NPC Natural Product Communications Vol. 7
No. 7
Quantitative and Physical Evaluation of Patchouli Essential Oils 927 – 930
Obtained from Different Sources of Pogostemon cablin
Norma Hussina,e*, Luigi Mondellob,f, Rosaria Costab, Paola Dugob, Nik Idris Nik Yusoffd,
Mohd Ambar Yarmoc, Ahmad Ab.Wahabe and Mamot Saidc
a
Twinning University Programme (between dUniversity Kebangsaan of Malaysia and bUniversity of Messina,
Italy)
b
Dipartimento Farmaco-Chimico, University of Messina, Viale Annunziata, 98168 Messina, Italy
c
School of Food Science and Technology, University of Kebangsaan Malaysia, Bangi, Selangor Darul Ehsan,
Malaysia
d
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, International Islamic University of Malaysia,
25200 Kuantan, Pahang, Malaysia
e
Malaysian Agricultural Research and Development Institute, 43400 Serdang Selangor, Malaysia
f
Università Campus Bio-medico, Via Álvaro del Portillo 21, 00128 Roma, Italy
normahus@mardi.gov.my

Received: March 28th, 2012; Accepted: May 23rd, 2012

Patchouli essential oil can be obtained from fresh, dried and fermented plant material. It is a highly valuable product in the fragrance industry and its quality
changes depending upon raw material age and oil storage. In this work, patchouli essential oils derived from different treatments have been subjected to GC-
FID quantitative analysis using an internal standard (ISTD) method with response factors (RF). Samples were obtained from i) fresh plants; ii) hydrodistillation
of one year mature and fermented plants; iii) hydrodistillation of one year mature plants; iv) commercial products from Indonesia and Malaysia. Linear
Retention Indices (LRI) for both polar and non-polar GC-MS analyses were also measured as a tool for qualitative analysis towards a homologous series of C7-
C30 n-alkanes. The results obtained confirmed that, in all samples, patchouli alcohol was the main volatile constituent, with higher amount in lab-scale
produced oils, compared with commercial samples. Other major compounds, in lab oils and commercial samples respectively, were: δ-guaiene, α-guaiene,
pogostol, seychellene and α-patchoulene. Another 36 compounds were also found.

Keywords: Quantitative analysis, Linear retention index (LRI), GC-FID response factor, GC-MS, Patchouli, Pogostemon cablin.

Quantification of constituents in essential oil research is a very Recently, some analytical procedures have been applied to
important tool in order to define a correct chemical amount in the Pogostemon sp. analysis by means of GC-MS coupled with
samples. The general procedure adopted when analysing an integrated chemometric methods [3]; application of PA external
essential oil by GC techniques is to report the raw area percentage standard calibration [4]; a comparison between supercritical fluid
(FID % or MS %). Another common practice is to apply a “ semi- extraction and steam distillation [5]; a fast analysis with a short
quantitation”, which means that peak areas are divided by an capillary column [6]; a simple wavelength detection of patchoulol
internal standard peak area. Basically, both procedures assume that by means of UV-spectrophotometer [7]; a GC-MS analysis with
the detector response is equal to unity. This assumption is different ionization techniques [8]; HPLC with UV detection at
approximately correct when target analytes are hydrocarbons, due 220nm for mono and sesquiterpenes [9], and a 2D fingerprinting
to a linear response of the FID detector to the carbon number. On analysis [10]. P. cablin essential oil was recently reported to contain
the other hand, when different moieties are present in the molecules 65.8% of sesquiterpene hydrocarbons, followed by oxygenated
to be quantified, such as keto-groups or carboxylic functions, FID sesquiterpenes (27.0%), dominated by patchouli alcohol, -
response undergoes a shift that needs to be “corrected” through the bulnesene (also known as -guaiene), -guaiene, -patchoulene and
measurement of response factors, for single compounds [1a-1c]. -patchoulene [11a]. Other Pogostemon species have been recently
Quantitative GC analytical methods based on response factors (RF) investigated i.e. P. heyneanus, whose predominant constituent was
and internal standard (ISTD) are still lacking for patchouli essential acetophenone (51.0%) followed by patchouli alcohol (14.0%)
oil as compared with several reports present in the literature based [11b]; and P. benghalensis, which showed a completely different
on the sole GC-MS qualitative fingerprinting. Patchouli essential oil composition compared with P. cablin (-caryophyllene, 12.5-
(PEO) is dominated by a large amount of oxygenated sesquiterpenes 15.2%; -bisabolene, 8-18%; elemol, 4-20%) [11c]. The woody
(such as pogostol and patchoulol). The presence of a hydroxyl group balsamic notes and the strong fixative properties of patchouli oil
in the structure of patchouli alcohol (PA) affects the FID response, made it a basic ingredient for certain high value perfumes, due to
for the reasons briefly explained here. The exact mechanism of the presence of patchouli alcohol (PA) and norpatchoulenol (NP)
flame ionization is still not completely understood. It seems likely [12a, 12b]. These two compounds have been considered in a study
that upon burning all carbon atoms are converted into methane [2]. on contact dermatitis as potential allergens [13]. In addition, PEO is
Therefore, hydrocarbons respond always in the same manner. When not only a fixative material in perfumery, but also an insecticide,
heteroatoms, like oxygen, are present in the organic solute, it flavouring agent and clothing odorant. The traditional uses
becomes necessary to calibrate this fluctuation by using response of P. cablin are based on some analgesic, anti-inflammatory and
factors, as previously reported by Costa et al. for other plants [1c].
928 Natural Product Communications Vol. 7 (7) 2012 Hussin et al.

Table 1: Sample description and physical evaluation of patchouli oil samples analyzed. factors. The latter have been measured for chemical groups,
No. of I.D. Source Moisture Recovery Color Solubility following the analytical procedure previously published [1c]:
Samples content % selected standard compounds, representative of a chemical class
(%) (e.g. limonene for monoterpene hydrocarbons), have been injected
2 A Fresh plants 1 73-75 0.38 Weakly n-Hexane
light green at 5 different concentrations with an internal standard (n-nonane).
and very When available, more than one compound for each chemical class
clear
2 B Hydrodistillation 10-12 0.64 Light n-Hexane
was injected. Each PEO sample has been run in triplicate and
of the pre-treated yellowish, repeatability tested by measuring the %RSD, which was <5% on
material (heating clear average, except for some small peaks, such as linalool, where it was
and fermenting in
water for 7 days) raised up to 12%. Linear Retention Indices (LRIs) have also been
of 1 year mature measured on both polar and nonpolar columns and reported in Table
and dried plants 2. With regard to the LRIs from the polar stationary phase, it must
2 C Hydrodistillation 10-12 1.12 Light n-Hexane
(Control) of 1 year mature yellowish, be highlighted that they are characterized by a lower level of
and dried plants clear repeatability and by a lack of literature data. Lab produced PEO
1 D Commercial unknown No data Brownish Dichloromethane. samples and the other two commercial samples showed the same
2, 3
PEO , received and Not soluble in n-
Indonesia from slightly hexane, turning pattern for six major chemical compounds, namely patchouli
supplier cloudy cloudy alcohol, δ-guaiene, α-guaiene, seychellene, pogostol and α-
1 E Commercial unknown No data Golden Dichloromethane.
PEO4,5, Malacca, received yellowish Not soluble in n-
patchoulene. PA content ranges were 51.9-68.0% and 46.3-45.9%,
Peninsular from and clear hexane, turning in lab PEOs and commercial samples, respectively. These results
Malaysia supplier cloudy demonstrated that Pogostemon cablin produces higher amounts of
1
Fresh P. cablin leaves and stems (maturity during harvesting was 5 months); patchoulol compared with previous research that reported 26-40%
2
Unknown distillation type; 3oil ageing time: 4 years; 4Steam distillation; 5oil ageing
time: 3 years and 30-40% [19a,19b]. This range far exceeded the one prescribed
by the Essential Oil Associations for authentic oil, that is 26-40%,
antibacterial effects [4,14]. As reported by Sundaresan et al. [15] also reported by Burfield [20,21]. Minor compounds (Table 2), such
and Xu et al. [3] PA content ranges from 14.6% to 23.3%. as norpatchoulenol, although present in lower amount, are
However, in some cases it was determined as 60.3% [16a]; 43.60- considered very important to the olfactory character of PEO, as
66.25% [16b]; and 44.35-56.30% [16c]. A standardized grade PEO, mentioned by Sunderkotter et al. in a study on (-)-patchoulol and
besides satisfying specific olfactory needs, must have a PA content (+)-norpatchoulenol [22]. These two compounds are estimated as
between 26-40%, as required by Essential Oil Associations, to enter the most important woody markers in mature P. cablin material and
the global markets. Table 1 reports the list and description of essential oils and suggest a further chiral investigation on the PEOs
samples analyzed, along with some physico-chemical data. Samples here investigated.
A, B and C were oils produced in the laboratory, whereas D and E
were two commercial PEOs produced in Indonesia and Malaysia, A samples presented trace amounts (≥0.01%) of other compounds,
respectively. such as benzaldehyde, 1-octen-3-ol, 3-octanone, 2-ethyl hexanol,
linalool, methyl salicylate and eugenol. Limonene and δ-elemene
From morphological observation, sample D was thicker and more were found in slightly higher amounts than in the other PEOs.
brownish than sample E; D oil was older than E oil. Both oils were Phytol, a diterpenoid compound, was also observed in the A oil,
not fully soluble in n-hexane and provided cloudy solution. The although in small amount (0.02%) compared with other samples. A
solubility of compounds in a non-polar solvent was probably contained a higher amount of cis-3-hexen-1-ol, already mentioned
reduced by terpene oxidation, which makes the oil more soluble in a by Oyen and Dung, which is a leaf alcohol with green and fresh
polar solvent (dichloromethane). PEOs from the laboratory (A, B notes that gives floral notes in trace amount [23]. Commercial
and C) were younger and showed a high solubility in non-polar PEOs, B and C samples had very low amounts of these compounds.
organic solvents (n-hexane). PEO obtained from fresh leaves and
stems (A) yielded a very low amount of oil (0.38%). This was due Two interesting unknown compounds (I and II) were found at
to the higher water content in fresh plant material (73-75%), as can consistent level: 3.4-9.8% and 4.7%, <0.01% and 0.8-0.9% and 0.6-
be seen in table 1. However, this result was similar to that reported 0.4%, respectively, for both the 6 lab samples and the 2 commercial
by Swamy et al. although the PA content was much lower (30.31%) PEOs. From a literature survey, it seems likely that the mass
[17]. Essential oil yields for B and C samples were 0.64% and spectrum (MS) of unknown II corresponds to that reported by Lu et
1.12%, respectively. B oil recovery was lower, probably due to al. [14], while no data can be found about unknown I. Further
volatiles loss during one week of wet fermentation and soaking investigation by isolation, purification steps and NMR, will be
conditions, after a pre-heating process. Sample C, being one year carried out in order to elucidate their structure.
dried, had a more concentrated essential oil (1.12%). According to
Hussin et al. [18], PEO recovery from premature and 4 months From the overall observations, it came out that PEOs produced on
dried P. cablin plants was 0.96%, an amount that increased after the lab-scale were richer in patchoulol compared with commercial
1 year of plant growth. In a research study by Kongkathip et al. on samples. This finding could be explained by the raw material used,
3-9 months dried P. cablin, a reduction of the PEO yield from 3.01 which was 12 months dried. No data are available for commercial
to 1.78% was observed [4]. It is a matter of fact, though, that the oil samples which relate to the same material age. Also, it must be
content and its composition are greatly affected by variables such as taken in consideration that hydrodistillation was conducted with a
site of harvest, material and condition of distillation. Evaluation of much lower amount of water and plant material (100 g vs 20 Kg on
the PEOs’ color was also carried out (Table 1). The main finding industrial scale). In this study, a new quantitative analytical method
was a darker color for commercial samples compared with lab scale was developed for the chemical investigation of P. cablin essential
produced oils. In total, 44 components have been determined in the oil. The results gathered from this research can be of support to
GC fingerprint of the PEOs analyzed. Table 2 reports the patchouli traders and producers worldwide. Quantification of
quantitative data expressed as g/100g, obtained through the volatiles was accomplished by accurate calibration based on the
application of the internal standard method with FID response internal standard method and FID response factors.
Pogostemon cablin essential oil Natural Product Communications Vol. 7 (7) 2012 929

Table 2: Chemical composition of the 8 patchouli essential oil (PEO) samples analyzed. Quantitative values are expressed as g/100g.
SAMPLE ID
Compounds R.F. LRI P LRI NP A1 A2 B1 B2 C1 C2 D E
(Exp.P) (ExpNP)
-Pinene 1.0 1021 932 0.04 0.04 0.02 0.04 0.05 0.07 0.07 0.04
Camphene 1.0 - 949 <0.01 <0.01 0.01 0.02 <0.01 <0.01 0.04 <0.01
Sabinene 1.0 - 972 <0.01 <0.01 <0.01 <0.01 <0.01 <0.01 <0.01 <0.01
-Pinene 1.0 1107 978 0.1 0.1 0.06 0.08 0.14 0.17 0.16 0.14
Limonene 1.0 - 1029 0.03 0.03 0.01 0.01 0.01 0.01 0.02 0.01
4,8-Dimethylnona-1,3,7-triene 1.0 - 1113 <0.01 <0.01 <0.01 <0.01 <0.01 <0.01 <0.01 <0.01
TOTAL MONOTERPENES 0.20 0.20 0.10 0.25 0.20 0.25 0.29 0.29
Linalool 1.3 1544 1099 0.06 0.06 <0.01 0.01 <0.01 0.01 <0.01 <0.01
-Terpineol 1.3 - 1196 <0.01 <0.01 0.01 0.02 0.01 0.01 <0.01 <0.01
Geranial 1.3 - 1268 <0.01 <0.01 <0.01 <0.01 <0.01 <0.01 <0.01 <0.01
TOTAL OXYGENATED MONOTERPENES 0.07 0.07 0.03 0.03 0.02 0.02 0.02 0.02
-Elemene 1.0 1466 1331 0.04 0.03 0.01 0.02 0.02 0.03 0.08 0.03
-Patchoulene 1.0 1475 1388 0.8 1.0 1.5 1.5 1.2 1.7 0.8 1.5
-Elemene 1.0 1752 1392 0.7 0.6 0.4 0.6 0.4 0.6 1.3 0.7
Cycloseychellene 1.0 1553 1418 0.2 0.1 0.3 0.4 0.3 0.3 0.6 0.5
(E)-Caryophyllene 1.0 1589 1424 1.2 1.1 1.0 1.3 1.1 1.5 1.1 2.0
-Guaiene 1.0 1584 1443 3.8 3.4 4.3 5.5 4.6 6.3 5.8 9.4
Seychellene 1.0 1628 1456 2.7 2.3 3.7 4.9 3.7 4.6 7.3 6.2
-Humulene 1.0 1660 1460 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.4
-Patchoulene 1.0 1624 1468 1.4 1.2 1.8 2.8 1.9 2.5 4.2 4.0
-Gurjunene 1.0 - 1473 0.4 0.4 0.7 0.7 0.6 0.9 0.5 1.1
Alloaromadendrene 1.0 - 1478 0.1 0.1 0.1 0.2 0.2 0.2 0.2 0.3
-Selinene 1.0 1698 1492 0.1 0.1 0.2 0.3 0.2 0.2 0.3 0.3
Aciphyllene 1.0 1693 1500 0.8 0.7 1.0 1.1 1.0 1.4 1.4 2.2
-Guaiene (-bulnesene) 1.0 1706 1511 5.8 5.2 6.8 7.4 7.0 9.5 9.2 14.4
Eremophila-1(10),8,11-triene 1.0 - 1514 0.06 0.05 0.03 0.04 0.04 0.04 0.07 0.1
7-epi--selinene 1.0 - 1524 0.1 0.1 0.1 0.2 0.1 0.2 0.3 0.2
TOTAL SESQUITERPENES 18.6 16.8 22.3 27.2 22.7 30.2 33.5 43.5
Elemol 1.3 - 1551 0.1 0.1 0.07 0.05 0.07 0.06 0.1 0.09
Norpatchoulenol 1.3 2093 1562 1.5 1.2 1.5 1.9 1.9 1.6 4.0 2.2
Caryophyllene oxide 1.5 1960 1586 0.9 0.8 1.7 2.0 1.8 1.6 4.6 1.8
cis-eudesma-4(15),11-dien-5-ol 1.3 - 1655 0.4 0.4 0.4 0.5 0.4 0.4 <0.01 0.3
Pogostol 1.3 2194 1649 5.7 6.0 5.5 4.6 5.2 4.7 3.5 3.7
Intermedeol 1.3 2236 1651 0.3 0.3 0.2 0.2 0.2 0.2 0.3 0.2
Patchouli alcohol 1.3 2162 1677 64.4 68.0 61.4 50.9 58.1 51.9 46.3 45.9
unknown #1 (oxygenated sesquiterpene) 1.5 - 1711 4.8 3.4 4.3 9.8 7.0 6.6 4.7 <0.01
(E,E)-Farnesal 1.3 - 1740 0.6 0.6 0.6 0.6 0.5 0.5 0.5 0.3
-Costol 1.3 - 1777 0.5 0.5 0.5 0.4 0.4 0.5 0. 0.2
TOTAL OXYGENATED SESQUITERPENES 79.3 81.4 76.2 71.0 75.7 68.0 64.5 54.7
unknown #2 1.3 - 1774 0.8 0.9 0.80 0.88 0.78 0.80 0.56 0.38
Benzaldehyde 1.3 - 961 0.03 <0.01 <0.01 <0.01 0.01 <0.01 <0.01 <0.01
1-Octen-3-ol 1.3 1446 979 0.3 0.2 <0.01 <0.01 <0.01 <0.01 <0.01 <0.01
2-Ethyl hexanol 1.3 1390 996 0.08 0.07 <0.01 <0.01 <0.01 <0.01 0.01 <0.01
Methyl salicylate 1.6 - 1193 0.01 <0.01 <0.01 <0.01 <0.01 <0.01 <0.01 <0.01
Eugenol 1.3 - 1353 0.01 0.01 <0.01 <0.01 <0.01 <0.01 <0.01 <0.01
Phytol 1.3 - 2110 0.02 <0.01 <0.01 <0.01 <0.01 <0.01 <0.01 <0.01
3-Octanone 1.3 - 984 0.01 0.03 <0.01 <0.01 <0.01 <0.01 <0.01 <0.01
TOTAL OTHER COMPOUNDS 1.3 1.2 0.9 0.9 0.8 0.8 0.6 0.4
R.F.: response factor; LRI P : linear retention index from the polar column; LRI NP : linear retention index from the non polar column.

Experimental PEO recovery: One hundred g of wet or dried plant material was
Plant material and treatments: Patchouli leaves and stems were weighed, added to 1.2 L distilled water and transferred into a 2 L
collected from Aromatic Plant Nursery, Essential Oil Incubator, round bottom flask in a Clevenger system. A cooling system was set
MARDI, Kuala Linggi Station, Malacca, Malaysia. The material up prior to heating the flask. Every hour the PEO was collected and
was dried and aged (fermented) for 12 months. The plant maturity pooled in a closed 10 mL bottle until distillation was completed.
of fresh material during harvesting was 5 months. The plants were The entire process lasted 7. The moist PEO was dried using
growing in acid soil type (containing bisulfite), where the condition Na2SO4, then carefully pipetted into a 1 mL GC vial and weighed.
was suitable for Pogostemon sp. and other aromatic crops in
Peninsular Malaysia. The plants collected were pre-dried with a Sample preparation for GC analysis: The PEOs (0.10 g), were
commercial solar dryer until less than 10% moisture, then dried mixed with ISTD (100 L of a 100,000 ppm stock solution) and 0.8
plants were kept in polyethylene (PE) bags, and drying continued at mL n-hexane. For retention indices, a mixture of n-alkanes
ambient temperature prior to essential oil processing. Each bag was {(C7:C30; Supelco (PA, USA)} was used.
able to hold up to 2.5 Kg dried materials. Fresh material collected
was kept in a refrigerator at 4oC for 2 days before distillation. A 100 GC-FID analysis: GC-FID analyses were carried out by means of a
g portion was added to 1.2 L distilled water and subjected to GC-2010 system (Shimadzu, Japan) equipped with an SLB-5MS
distillation for up to 7 h using a Clevenger apparatus (2 L capacity). column (30 m × 0.25 mm i.d. × 0.25 m df), supplied by Supelco.
A full description of the samples is described in Table 1. Oven temperature program was: from 50°C at 3°C/min to 300°C,
then held for 5 mins. Injection temperature was 280°C; injection
Moisture analysis: The moisture content of the fresh and dried took place in split mode with a split ratio of 1:100. Carrier gas was
samples (1 g) was determined using an automatic IR-Moisture helium, with a linear velocity of 30 cm/s, pressure was 99.8 KPa.
balance at 105oC until the moisture was completely removed. The Detector temperature was 300°C, detection gases were H2
time taken to complete the analysis ranged from 6 to 12 mins. (40 mL/min), N2 (40 mL/min) and air (400 mL/min).
930 Natural Product Communications Vol. 7 (7) 2012 Hussin et al.

GC-MS analysis: GC-MS analyses were carried out with 2 different Non-polar system: Injector temperature was 280°C, and injection
GCMS-QP2010 systems (Shimadzu) equipped with SLB-5MS (30 took place in split mode with a split ratio of 1:200. Oven
m × 0.25 mm i.d. × 0.25 m df) and Supelcowax-10 (30 m × 0.25 temperature program was: from 50°C at 3°C/min to 300°C, held 5
mm i.d. × 0.25 m df) columns (Supelco), respectively. min. Carrier gas was helium, with a linear velocity of 30.0 cm/s,
pressure was 26.7 KPa. Ion source temperature was 220°C, while
Polar column system: Injector temperature was 250°C, and interface temperature was 250°C. Scan range was 40-400 m/z. For
injection took place in split mode with a split ratio of 1:100. Oven mass spectral library matching, FFNSC 1.3, Adams and other
temperature program was: from 50°C at 3°C/min to 280°C, held 5 homemade databases provided with LRIs were used [24a,24b].
min. Carrier gas was helium, with a linear velocity of 30 cm/s,
pressure was 28.4 KPa. Ion source temperature was 220°C, while Acknowledgements - This work was supported by the University
interface temperature was 250°C. Scan range was 40-350 m/z. of Messina, Italy, and the University of Kebangsaan, Malaysia.

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Natural Product Communications Vol. 7 (7) 2012
Published online (www.naturalproduct.us)

Antihyperglycemic agents from Ammannia multiflora


Harish C. Upadhyay, Natasha Jaiswal, Akhilesh K. Tamrakar, Arvind K. Srivastava, Namita Gupta and Santosh K. Srivastava 899
Free Radical Scavenging Activities of Naturally Occurring and Synthetic Analogues of Sea Urchin Naphthazarin Pigments
Natalia K. Utkina and Natalia D. Pokhilo 901
Drynariae Rhizoma Increases Immune Response in Mice
Hyo-Jin An, Gil-Goo Lee and Kyung-Tae Lee 905
Antioxidant, Antimicrobial and Wound Healing Activities of Boesenbergia rotunda
Rungrat Jitvaropas, Suphaket Saenthaweesuk, Nuntiya Somparn, Amornnat Thuppia, Seewaboon Sireeratawong and
Waranyoo Phoolcharoen 909
Revisit to (Z)-Civetone Synthesis
Hisahiro Hagiwara, Teppei Adachi, Tomomi Nakamura, Takashi Hoshi and Toshio Suzuki 913
Search for Bioactive Compounds from Cantharellus cibarius
Włodzimierz Maria Daniewski, Witold Danikiewicz, W. Marek Gołębiewski, Mirosław Gucma, Agnieszka Łysik, Jacek Grodner and
Elżbieta Przybysz 917
Fatty Acid Composition of Juniperus Species (Juniperus Section) Native to Turkey
Ayşegül Güvenç, Nurgün Küçükboyacı and Ahmet Ceyhan Gören 919
c-AMP Dependent Protein Kinase A Inhibitory Activity of Six Algal Extracts from South Eastern Australia and Their
Fatty Acid Composition
Ana Zivanovic and Danielle Skropeta 923
Quantitative and Physical Evaluation of Patchouli Essential Oils Obtained from Different Sources of Pogostemon cablin
Norma Hussin, Luigi Mondello, Rosaria Costa, Paola Dugo, Nik Idris Nik Yusoff, Mohd Ambar Yarmo, Ahmad Ab.Wahab and
Mamot Said 927
Essential Oil Composition of Prasium majus from Croatia
Igor Jerković, Marko Šuste, Željan Maleš and Kroata Hazler Pilepić 931
Composition and Antipathogenic Activities of the Twig Essential Oil of Chamaecyparis formosensis from Taiwan
Chen-Lung Ho, Kuo-Feng Hua, Kuan-Ping Hsu, Eugene I-Chen Wang and Yu-Chang Su 933
In vitro Antimicrobial Properties and Chemical Composition of Santolina chamaecyparissus Essential Oil from Algeria
Samah Djeddi, Khadidja Djebile, Ghania Hadjbourega, Zoubida Achour, Catherine Argyropoulou and Helen Skaltsa 937
Chemical Composition and in vitro Antimicrobial Activity of the Essential Oil of the Flowers of Tridax procumbens
Rajesh K. Joshi and Vijaylaxmi Badakar 941
Chemical Composition and Antimicrobial Activity of Essential Oil of Heracleum rigens
Nataraj Jagannath, Hanumanthaiah Ramakrishnaiah, Venkatarangaiah Krishna and Prameela Javarayi Gowda 943
Chemical Composition and in vitro Evaluation of Antimicrobial and Anti-acetylcholinesterase Properties of the Flower Oil of
Ferula lutea
Mansour Znati, Aymen Jabrane, Hafedh Hajlaoui, Fethia Harzallah-Skhiri Jalloul Bouajila, Joseph Casanova and Hichem Ben Jannet 947
Determination of Antioxidant Properties of 26 Chilean Honeys and a Mathematical Association Study with their Volatile
Profile
Elizabeth Sánchez, Marisa Piovano, Erika Valdés, Manuel E. Young, Cristian A. Acevedo and Mauricio Osorio 951
Chemical Constituents and Antioxidant and Biological Activities of the Essential Oil from Leaves of Solanum spirale
Sukanya Keawsa-ard, Boonsom Liawruangrath, Saisunee Liawruangrath, Aphiwat Teerawutgulrag and Stephen G. Pyne 955

Review/Account
Acetylcholinesterase Inhibition within the Lycorine Series of Amaryllidaceae Alkaloids
Jerald J. Nair and Johannes van Staden 959
Alkaloids Produced by Endophytic Fungi: A Review
Yanyan Zhang, Ting Han, Qianliang Ming, Lingshang Wu, Khalid Rahman and Luping Qin 963
Natural Product Communications
2012
Volume 7, Number 7
Contents
Original Paper Page

Chemical Constituents of Blumea balsamifera of Indonesia and Their Protein Tyrosine Phosphatase 1B Inhibitory Activity
Azis Saifudin, Ken Tanaka, Shigetoshi Kadota and Yasuhiro Tezuka 815
A New Sesquiterpene from an Endophytic Aspergillus versicolor Strain
Xiang-Hong Liu, Feng-Ping Miao, Xiao-Dong Li, Xiu-Li Yin and Nai-Yun Ji 819
Skin Permeation of Cacalol, Cacalone and 6-epi-Cacalone Sesquiterpenes from a Nanoemulsion
María Luisa Garduño-Ramírez, Beatriz Clares, Valeri Domínguez-Villegas, Concepción Peraire, María Adolfina Ruiz,
María Luisa García and Ana C. Calpena 821
Compounds with Antiproliferative Activity on Five Human Cancer Cell Lines from South Korean Carpesium triste
Hyung-In Moon 825
Biogenetic-type Synthesis of 2-Hydroxy-4,4,7-trimethyl-1(4H)-naphthalenone, a Modified Apocarotenoid from
Ipomoea pes-caprae
Kamalesh P. Pai Fondekar, Shashikumar K. Paknikar, Savia Torres and Shrivallabh P. Kamat 827
Ixoroid: A New Triterpenoid from the Flowers of Ixora coccinea
Muhammad Ali Versiani, Ambreen Ikram, Salman Khalid, Shaheen Faizi, and Iftikhar Ahmed Tahiri 831
Distinguishing Between R- and S-Antcin C and Their Cytotoxicity
Ting-Yu Lin, Shih-Chang Chien, Yueh-Hsiung Kuo and Sheng-Yang Wang 835
Chemical Investigation of Saponins from Twelve Annual Medicago Species and their Bioassay with the Brine Shrimp
Artemia salina
Aldo Tava and Luciano Pecetti 837
Inhibition of cPLA2 and sPLA2 Activities in Primary Cultures of Rat Cortical Neurons by Centella asiatica Water Extract
Patrícia P. Defillipo, André H. Raposo, Alessandra G. Fedoce, Aline S. Ferreira, Hudson C. Polonini, Wagner F. Gattaz and
Nádia R. B. Raposo 841
Triterpene Glycosides from the Sea Cucumber Eupentacta fraudatrix. Structure and Cytotoxic Action of
Cucumariosides A2, A7, A9, A10, A11, A13 and A14, Seven New Minor Non-Sulfated Tetraosides and an Aglycone with an
Uncommon 18-Hydroxy Group
Alexandra S. Silchenko, Anatoly I. Kalinovsky, Sergey A. Avilov, Pelageya V. Andryjaschenko, Pavel S. Dmitrenok,
Ekaterina A. Martyyas and Vladimir I. Kalinin 845
Two New Asterosaponins from the Far Eastern Starfish Lethasterias fusca
Natalia V. Ivanchina, Anatoly I. Kalinovsky, Alla A. Kicha, Timofey V. Malyarenko, Pavel S. Dmitrenok, Svetlana P. Ermakova and
Valentin A. Stonik 853
Corylucinine, a new Alkaloid from Corydalis cava (Fumariaceae), and its Cholinesterase Activity
Zdeněk Novák, Jakub Chlebek, Lubomír Opletal, Pavel Jiroš, Kateřina Macáková, Jiří Kuneš and Lucie Cahlíková 859
Improved Method for Isolation of Lycopsamine from Roots of Comfrey (Symphytum officinale)
Damjan Janeš, Boštjan Kalamar and Samo Kreft 861
Trigonelline and other Betaines in Species of Laminariales
Gerald Blunden, Michael D. Guiry, Louis D. Druehl, Kazuhiro Kogame and Hiroshi Kawai 863
Anticomplement and Antimicrobial Activities of Flavonoids from Entada phaseoloides
Ke Li, Shihua Xing, Mengyue Wang, Ying Peng, Yuqiong Dong and Xiaobo Li 867
Antioxidant Compounds from Algerian Convolvulus tricolor (Convolvulaceae) Seed Husks
Nassira Kacem, Anne-Emmanuelle Hay, Andrew Marston, Amar Zellagui, Salah Rhouati and Kurt Hostettmann 873
Quality Control and Analytical Test Method for Taxus baccata Tincture Preparation
Pamela Vignolini, Beatrice Gehrmann, Matthias Friedrich Melzig, Leonardo Borsacchi, Arianna Scardigli and Annalisa Romani 875
Chalcones in Bioactive Argentine Propolis Collected in Arid Environments
Eliana Solórzano, Nancy Vera, Soledad Cuello, Roxana Ordoñez, Catiana Zampini, Luis Maldonado, Enrique Bedascarrasbure and
María I. Isla 879
Inhibitory Effect of Hexahydrocurcumin on Human Platelet Aggregation
Huei-Ping Dong, Rei-Cheng Yang, I-Chun Chunag, Li-Ju Huang, Hsing-Tan Li, Hsin-Liang Chen and Chung-Yi Chen 883
Biotransformation of Salvianolic acid B by Fusarium oxysporum f. sp. Cucumerinum and Its Two Degradation Routes
Shidong Kan, Huimin Lin, Ji’an Li, Lei Shao and Daijie Chen 885
Phytopathogenic Fungal Inhibitors from Celery Seeds
Tao Liu, Fu-Guang Liu, Hui-Qin Xie and Qing Mu 889
Synthesis and Antimicrobial Activities of Some Sulphur Containing Chromene Derivatives
Tuba Şerbetçi, Seher Birteksöz, Soizic Prado, Sylvie Michel and François Tillequin 891
Effect of Polyamines on Shoot Multiplication and Furanocoumarin Production in Ruta graveolens Cultures
Renuka Diwan and Nutan Malpathak 895

Continued inside backcover