Você está na página 1de 12

lSSN 1020-5586





∧ :nternationa:
Program in the
Chemical ScienOes

findexedand Abstractedby ChemicalAbstracts]

ACGC ChemicalResearchCommunications

Cover page: The cover page includesthe structureof the alkaloid actinodaphninewhich was
subject of the first paper published in ACGC Chemical Research Communications. This
kaloid was isolated from the root bark of Zirsea diversifolia from the district of Subang,West

ACGC CRC Editorial Board Executive Editor

Prof. StephenG. Pyne
Department of Chemistry
University of Wollongong
(e-mail) Stephen_Pyne@uow.edu.

Dr. M. Akerblom (IPICS)
Dr. J. R. Cannon (Australia)
Prof. B. H. Han (Korea)
Prof. S. Hill (UNESCO)
Dr. Nordin Bin Haji Lajis ({INESCO-SE Asian
Regional Network)
Dr. Rune Liminga (IFS)
Assoc. Prof. B. Noller (Secretary, Australia)
Dr. Mohinder Singh (IKM)
Prof. J. Webb (Australia)

Scientific Advisory Board

Prof. Hajime Akimoto (Japan)
Dr. Dayar Arbain (lndonesia)
Prof. David St. C. Black (Australia)
Prof. Lourdes J. Cruz (Philippines)
Prof V. G. Kumar Das (Malaysia)
Dr. R. Liminga (Sweden)
Dr. Neville Marchant (Australia)
Dr. Hermann Niemeyer (LANBIO)
Prof. Min Bo Chen (China)
Dr. SurachaiNimgirawath (Thailand)
Dr. Mohan Perera(UNESCO, New Delhi)
Dr. T. Ramasami(CLzu Madras, India)
Prof. Vichai Reutrakul (Thailand)
Prof. Sang Chul Shim (Korea)
Dr. T. H. Spurling (Australia)
Prof. W. C. Taylor (Australia)
Prof. Prapin Wilairat (Thailand)
Prof. Won Sik Woo (Korea)
ACGC ChemicalResearchCommunications

Sediment Accretion and Trace Metal Concentrations in the Surface Sediments of

Kuantan Mangrove ForestoMalaysia
Kamaruzzaman,B. Y., Jamil, B. T. and Hasrizal, S.

Sesquiterpenesand Triterpenes from Sonchus Oleraceus(Asteraceae) 14

Hesham R. El-Seedi

23-Hydroxy-24-methylenecycloartanoloa new cycloartane triterpenoid from the

aerial parts of Sarcococca coriaceaof Nepaleseorigin 19

Arjun Paudel, Narayan P. Rai, IulangalaD. Manandhar, M. Iqbal Choudhary,Kazu

Masuda, and Atta-ur-Rahman

Chemical Compon ents of M elastoma malabath ri cum 28

Sri Nurestri Hj Abdul Malek, Baek S.H. and Asnuzilawati Asari

Unusual Oxygenated Cations in Electrospray Ionisation Mass Spectroscopyof

Polyprenols from Jatropha curcas L. 34

John A Rideout, Consolacion Ragasa,and Hiu Tian Ngo

Secondary Metabolites from Jasminum Sambac and.Cananga Odorata 40

ConsolacionY. Ragasa,Benjie G. Tamboong,and John A. Rideout

The Chemical Constituents of Macaranga triloba 48

F. Ahmad,L. L. Chengand R. Mat Ali

Geochemistry of Some Heavy Metals in Sediment Cores from Setiu Mangrove

Forest, Terengganu, Malaysia 53

KamaruzzamanBin Yunus

Structure and Characterization of SomeNew Coordination Compounds of

Organotin(IV) with Schiff Bases 62

NavneetKaur, H. L. Singh, S. Varshneyand A. K. Varshney

Hydroxy Betulinic Acid from the Leaves of Ortltosiphon Stamineus 69

M. AmzadHossain, and Zhari Ismail

Rapid Synthesis of a model chrymutin like compound and its derivatization in weak
alkaline or in neutral medium.
H. N. Roy, A. M. Paul and M. S. Sarkar 74
ACGC ChemicalResearchCommunicationsVol. 16, 2003 - Page19

23-Hydroxy-24-methylenecycloartanol,a new cycloartane

triterpenoid from the aerial parts of Sarcococca coriaceaof
A{un Paudel,fNarayan P. Rai,t MangalaD. Manandh-,*'t M. Iqbal Choudh*y,iKazu Masuda,$

and Atta-ur-Ratrmant

Central Department of Chemistry, Tribhuvan University, Kathmandu, Nepal,i H.E.J Research

Institute of Chemistry, International Center for Chemical Sciences, Universify of Karachi,
Karachi, 75270, Pakistan,t and Showa Pharmaceutical University, Machida, Tokyo 194-8543,


A new triterpenoid, 23-hydroxy-24-methylenecycloartanol, and the known compounds, lupeol,
and sitosterol-3-O-B-glucopyranoside
oleanolic acid, stigmasterol-3-O-B-glucopyranoside
betulin, were isolated from the aerialparts of Sarcococcacoriacea (Hook. F.) Sweet(Buxaceae).
Their structures were assigned on the basis of spectral data. The dichloromethane extract was
found cytotoxic while the methanol extract showed enzpe inhibition of polygalacturonase.
Keylvords: Sarcococcacoriacea(Hook. F.) Sweet;Aerial parts; Triterpenoid

Sarcococca coriacea (Hook. F.) Sweet, Buxaceaeris an evergreen shrub widely distributed in the
Mahabharat range of Himalayan Kingdom of Nepal. The plant has exhibited antibacterial,
anticholinesterase,antitumor, antiulcer and ganglion blocking' properties. Different parts of the
plant are harnessedin the treatment of fever and rheumatism in traditional medicine.' A number

To whom correspondenceshould be addressedTel: 977-01-332034, 977-01-260384Email:
i Central Department of Chemistry, Tribhuvan University, Kathmandu, Nepal,
t H.E.J ResearchLrstitute of Chemistry, lnternational Center for Chemical Sciences,University
of Karachi, Karachi-7 5270, Pakistan
$ Sho*a PharmaceuticalUniversity, Machida, Tokyo 194-8543, Japan
ИC G C C t t θ t t C″″露
α′R ♂θαr ε
″J σ ο ηJ σ
αι 4 s レb l ′こ 2 θθg _ P a g e 2 0

3.The present study has resulted in

辟om S cο /Jα
of steroidal alkaloids has also bcen reported」 εθα

the isolation of a new triterpene l along with known compounds, lupeo1 2, oleanolic acid 3,

stittasterol-3-0-β ‐
glucOpyranoside 4,β ―
glucOpyronosice 5 and betulin4 6
smctures Ofthe isolated compounds are assigned rnainly on the basis oftheir spectral data.

Results and Discussion

A methanol extract of the al

ac五 αεθα was evaporated to yield a_y
parts of the S ガcο

residue.The residue was partitioned between distilled water and hexane,then dichloromethane.
The dichloromethane extract was suttected tO Colllmn chromatography to afford compounds l-6.

Compolmd l(C31H5202,EIMS“ /_7456)was iS01ated as a white crystallinc solid,m.p.

C,blg+85.7° ons江 3400(OH),
(60.9,veoH)・ The R spectmm displayed absorp■
1.EIMS ga■ /e a molecular ion pcak at“ /_-456
2900(CH),1600(olCin),1020(C― O)Cm‐

(C31H5202)and the peak at“ /z441 ducto M+― CH3・ The base peak at″ ル 438 was due to the loss
- 4 2 3 , 4 2 0 , 4 0 5 a n d 3 9 5 w e r e a s s i g n e d H 2f 0o r C[ HM 3―1 ' , [ M
o f w a t e r i o m M + . T h e p e a k s a/t_〃

2H20]+,[M-2H20 CH3]+and[M― C3H7 H20]+reSpect市 ely.(Fig.4)

The lH―NMR(CDC13)SpeCtrum Of compound l displayed four tertiary methyl singlet(δ ―

Value in

ppm)at O.807(H-30),0.895(H-31),0.948(H-29)and O.965(H-18).Three methyl doublet

signals at O.950(H-21),1.097(H-27)and l.081(H-26),and tWO exocyclic methylene proton

signals(H2 28)at 4.918 and 5.018 were also assigned.A pair of doublets at O.329 and O.547,with

coupling constant of 4 Hz indicated that l has a cyclopropane五 ng.The heptet at 2.319(J=6.4

HZ)WaS assigned to a methine proton at H-25.Two doublet of doublets at 3.282(J=5.7

and 4.210(J=6.4,6.4 Hz)were assigned for the protons at H-3 and H-23 respectively.

NMR spectrum showed the presence of thirty― one carbons in the molecule. The DEPT 135

spec― showed twenty flve carbon signals with fourteen positive and eleven negative signals.

Analysis of the l)EPT-90 specmm revealed seven CH and seven CI13 CarbOns in the l■ olcculc,

w h i c h w a s i r t h c r s u p p o r t e d Nb My R .l SH i‐x p e a k s f o r c a r b o n m i s s i)nmg 魚
the DEPT-135 were

assigned as quatemary.

The partial structures for五ngs A,B and C were S01Ved by detailed analysis of I‐ IMBC

specmm(Fig.2).Thc C=C bOnd collllectivitiesラ ル.C-1-C-2-C-3,C-5-C「 6-C-7,C-11-C12 and

C-22-C-23 were detel.1.ined ttЮm analysis of HMBC and COSY spectra.Thc chernical shi■ s of

carbons in五 ngs A,B,C and lD are vcry close to CyC10artanc denvatives.Also,analysis of the

mass specm of cOmpound l indicated that it Was a de五 Vative of the 4,4‐diinethyl tン
pe of
chain carbon,as depictOd in Fig.4. On the basis of
cycloartane triterpenOid Ⅵ/ith an extra side―
ИC C C C 力θ“J c α αr c 力σο″“z ηi C α
′R “ θ ″0 “s レb i f a 2 θ
θ3 - P a g e 2 1

spectral data, compound l was elucidated as 23-hydFOXy_24‐ cycloartanol. The


stereochcmistry at C-23 was not dete..1.ined.

Compound 2(C30H500,EIMS,″ 426,M+)waS iS01ated as a whitc crystalline solid,m.p.

216°C,L]『 +52.1(ε O.H,MCOH).On me bttis ofIR― spectrum,2D■ ゞヽ個R―spectroscopy,mtts

spectroscopy,dircct companson with an authentic sample(mmp and co― tlc)and the reported

spcctral data5,thc compound 2 was identifled as lupeol.

Compound 3 was isolated as O white crystalline solid,In,p.285° C.From IR― spectroscopy,2D―

NNIIR spectroscopy, companson with spcctral data6, and direct companson with an authentic

sample(mmp and cO― tic),the compound was assigned as olcanolic acid.

Compolmd 4(C35H5806),FAB― M[S(+):“ /Z597[MttNa]+waS iS01ated as a white

NNIIR―spectra, and companson with reportOd

crystallinc solid,m.p.295°C. From IR― and 2E)―

spectral data7,8 and an authentic sample(mmp and CO― tlc),the cOmpound was assigned as


Compound 5(C35H6006)WaS iSOlated as a white crystalline solid,m.p.253°

co m p o l l n d was assigned as sitostcrol-3-0-β
glucOpyranoside by dircct compa r i s o n w i t h
authentic salnplc(mp andCO―
Compound 6 is idcntifled as betulin by companson、 m value of
/ith the reported lH―

betulin 8.


Gι″eraJ IhηθrliHθ
″″′Practtts=l■lelting points werc uncorrected,and were recorded on an

electnc Sun―Vic U.K.IR‐ spectra were recordcd in KBr discs.lH― NMR(400 Ⅳ EIz)speCtra Of

compounds l,2 and 3、 rere recorded on JEOL―ЛゞⅣl―

LA 400WB spectromcter. 13c_NNER spectra

and DEPT spectra of compollnds l and 2 were recorded on a Bruker AC-300 operating at 75

NEHz.lH― NNIR(500 MHz)ofcompounds 4,5 and 6 were rccordcd on JEOLα -500 speOtrometer.

The chemical shift(δ)values are cxpressed in ppm units,and coupling constants(の are」 ven in

Hz.The mass spectra were recorded on a JEOL― 」NIS―D300 14ass spectrolneter.Pre―coated TLC

plates(G254)Were uSCd to check the polanty ofthe compounds,and silica gel(60-200 mesh,E
MerCD Was used for collllllm chromatography.

r s M a ″r l i a JTsh「e p l a n t m a t ea 五
PJa“ ls were collected iom Hattiban,Kathnandu in September

1999.The plant was identifled by Pro■ Dr.R.P.Chaudhary,Taxononlist,Ccntral Deparment Of

Botany,T五 bhuvan Universittt Kirtipllr,Kathnandu,Nepal.A voucher specimen(V.No.SK

2057)was deposited in the Central Department ofBotany,Tribhuvan University.

∠CCC CJle″ご
cα α′
′Rω θ JO“ .fα 2θθ3-Page 22

Errac″ο“ α“J ttοこ

面 o″=Air‐dried,pOwdered plant―
m atenals(l kg)Were perc01ated in
m e t h a n o l ( 31×0 L 。
)at r00m temperature for 48 hours for each extract.The methanol ex
concentrated under reduced pressllre to Obtain a viscous dark red―
residuc(340g).Distilled water
200 mL)f0110Wed by
(200 mtt Was added,and the residuc extracted with hexane(5×
??m⊃ tO yield ll g and 36 g extracts respect市
he diCh10romethane
extract(20.36g)was ChrOmatographed on a silica column eluted with hexane/cthyl acetate
m破 tures with increasing polarity.ColШ ttactiOns were rechroiatographed and recrystallized

to afford compolmds(1‐ 5).Eluting the colum with pllre cthyl acetate gave a fcW iactions

contalmng two components. The Ⅱ lixture was dissolved in ethyl acetate and a few drops of
hexane added until turbid. On standing, a crystallinc compound separated.The compound was

irther pu五 fled by triturating、ア

ith ethyl acetate in hexane. The recrystallized compound was

follnd to be a mixture of compollnd l and betulin(6)in the ratio of(2:3).Rechromatography of

the m破 ture(SO市ent??)ゝieldcd pure 6.

23,ワ ″りた2イー c″θ9`Jaα r`α

″θ̀りこ ″οJ`砂「

C ; [ α] 『 + 8 5 . 7 °
恥h i t e c r y s t d u n e s o mh .とp . 1 9 9 ° C(cO.9,MCO菫 ゝR vtt cm・ :33oO,2900,

1600,1460,1020,1000;lH― NMR(CDC13,400 MHz)δ O.948(3H,s,CH3 29),0.807(3H,s,CH3

30),0。329(d,lH,J=4.O Hz,H-19),0.547(d,lH,J=4.O Hz,H‐ 19),0・895(3H,s,H-31),0.965

(3H,s,H-18),0.950(d,3H,J=6.8 Hz,CH3 21),4.918,5.018(2H,H-28),1.097(d,3H,J=6.4

Hz,H-27),1.081(d,3H,」 =6.4 Hz,H-26),1.25,1.56(2H,H-1),1.59,1.76(2H,H-2),3.282(dd,

lH,J=5.71・Iz,H-3),1.30但 -5),1.59,1.78(2H,H-6),1.13,1.33(2H,耳 -7),1.50(H-8),1.10,1.99

1.38∈ I‐ =6。2,6.4 Hz,H-23),2.319(lH,dq,J=6.4 Hz,H-25);13c_NMR
(CDC13),SCe Table l;EIMS″ /z[ゝ凋


m.p.216° C;[α ]『 +52.1(`0.H,MeOHtt vtt Cm・

Z″ ″ Jの :Ⅵ唖 te crystalline soliと :3500,

2900,1640,1450,1380,1040,lH― NMR(CDC13 400 MHz)δ O.966(3H,s,H-23),0.759(3H,s,


(td,lH,J=1.0,1.0,1.OI‐Iz,H-29),4.682(d,lH,J=2.2 Hz,H-29)1.678(3H,s,H-30),3.184,(d,
lH,J=10.5 Hz,H-3),1.653,0.906(2H,H-1),1.529,1.598(2H,H-2),0.680(d,lH,」 =9.0耳 z,H―

5),1.405,1.521(2H,H-6),1.388,1.385(2H,H-7),1.286(H‐ 9),1.235,1421(2H,H-11),1.078,

1.653(2H,H-12),1.643∈ I‐13),0.993,1.708(2H,H-15),1.374,1.472(2H,H-16),1.358(H‐ 18),

2.360(td,lH,」 =11.0,11.0,5.9 Hz,H-19),1.330,1.903(m,2H,H‐ 21);13c_NMR(CDC13),Sec

ИCGC Cttθ 閣たα′R“ θαrctt Cο α′J04s K,た ノこ 2θθ3-Page 23

Table l;EIMS″ 々 [M+],426(100),411(25),408(21),393(12),365(23),218(50),207(75),


θ物 ″οJ l i c″ J Ⅱn e s o Ⅱ
∠ の 「W h i C C r y 償 C , L ] 『 + 9 7 . 0 ( σ α1 4 M c O H ) V t t C m ・ :

2900, 1685, 1460, 1385, 1360, lH― blMR (CDC13)δ O・

95,1.58(2H, H-1),1.54,1.54(2H,

H-2),3.20(lH,dd,J=11.4,4Hz,H‐ 3),0,70(H-5),1.35,1.35(2H,H-6)1.26,1.42(2H,H-7),1.52

(H-9),1.84,1.88(2H,H-11),5.26(dd,1耳 ,J=3.7,3.7 Hz,H-12),1.04,1.69(2H,H-15),1.58,

1.95(2H,H-15),1.58,1.95(2H,H-16),2.80(dd,lH,J=13.7,4.3 Hz,β H-18),1.44,1.60(2H,H―


3H,H-25),0.73(s,3H,H-26),1.H(S,3H,H-27),0.88(s,3H,H-29),0.91(S,3H,H‐ 30);13c_

NMR(CDC13),See Table l.

θ の =White crystallinc compolmd;mop.(295°

0-β gレ CaFy″ ″οsJ″
StigttαsたrθJ-3‐ C),lH―NMR

(500 ⅣIIz)δ O.954(s,3H,H-19),0.688(s,3H,H-18),1.091(d,3H,J=6.4 Hz,H-21),0.928,

0.878(d,J=6.4 Hz,3H,H-26,3H,H-27),0.899(t,3H,J=7.3 Hz,3H,H‐ 29),4.317(m,lH,H3-

α),5.36(H-6),5.233(dd,lH,J=8.7,15。 l Hz,H-22),5.078(dd,lH,J=8.9,15。 l Hz,H-23),1.882

(2H,H-7),1.882(H-8),1.371(2H,H-11),1.940,1.964(2H,H-12),1.0012,1.727(2草 ,H-1),

1.753,(d,2H,H-2),1.325,1.281(2H,H-16),1.727,1.001(d,2H,J=6.O Hz,H‐ 1),2.506(d,2H,

J=10.5 Hz,H… 2),2.753(d,」 =13.O Hz,H-2),1.964,1.940(2H,H-12),5.363(td,lH,5.0,2.0,2.0

Hz,H-6).13c NMR(C5D5N,75 MHz),SCe Tablc l;FABMS[M+Nal+497,154(100),

s `′
sirο θ「
″ル3‐ ″′θ
ルノ“COpッ sJ″ C,Rf O.63(1:5,
θ「シ White cwstalline compollnd m.p.253°
lH― O.985(s,3H,H-23),0,773(s,3H,H-24),0.913(s,
Bα″Jli4`の『 NMR(CDC13,400 MHz)δ

3H,H-25),0.750(s,3H,H-26),1.132(s,3H,H… 27),0.904(s,3H,H-29),0.927(s,3H,H-30),

3.217(dd,lH,J=10.4,4.9 Hz,H-3α ),4.681(lH,m,H29α ),4.579(lH,m,H29β ),5.277(dd,lH,

J=3.3,3.3 Hz,H-12),2.1818(dd,lH,J=4.0,13,7 Hz,H-18β ).The COmpollnd was idcntiied by

qⅣR values with reported spectra8.
direct companson oflII〕
=IИethanol,dicthyl ethctt dichibromcthane,and hexane extracts of plant
Bri″ιs力rtmp bliaα
sbh五r i m p b i o a s s a y . T h e b i o a s s a y s h o w e d t h a t t h e d i c h l o r o m e t h a n e
w e r e s u t t e c t e d tnOc ―
has an LC50 Value 122.743 shoWing some cytotoxic activity.Diethyl ether, hexane,
dichloromethane and aqueous extracts of the plant were examined for inhibition on

polyglacturonasc(Dinglds cup―plate method)produced by β ο′ “α・The result showed

7′お εttθ
L showed 33.33%and
that thc methanol and aqucous extracts,at concentrations of l m3/100 μ
‐ely(disulled wtter and anol
ne aCtiVity respecti、
32.14%inhibition of ellz「 meⅢ Were used as
control)whercas the dicthyl ether extract showcd only 10.28%inhibition ollro dieth
ACGC ChemicalResearchCommunicationsVol- 16, 2003 -Page}4

used as control). Dichloromethane extract showed the least inhibition of 7.14o/oonly (pure
dichloromethanewas used as control).

Fig. I Structuresof isolatedcompounds


,ゝ q ζ


T へ
11 ) fIH2
Lく CH3

Fig. 2 Partial structure of compound 1 solved by HMBC data. Two and three bond C-H
correlationsfrom methyl protonsare shownin bold lines and thosefrom methyleneprotons(H2-
19,H2-28)andmethineprotons(H-8) depictedasalrolv\rs.
ACGC ChemicalResearchCommunicationsVol. 16, 2003 -Page25

lH Chemicalshift mm COSY


4 210 dd

6/脚 ま
13c chemicalshift from 2D‐NMR analyses

Fig. 3 lH 1fromCOSY)and of compoundI by 2D-NMR.

ぽ CH3 ヽ
ぼ H20 _

ぽ ‐ 2い CH3 _
r H20 H20ヽ
卜H20 ぽ ‐ 20 H2∝ L
-卜 e 励を40520)
耐 C3H7 H20ヽ
z/z 395(35)

z/_7123(93) 4/_7255(28) 7_‐297(55) ″ν2316(96)


Fig. 4 MS fragmentation pattern of compound 1. Relative intensities are shown in parenthesis.

ACGC ChemicalResearchCommtuications Vol. 16' 2003 -Page26

Table I - Chemical Shift Data (ppm) of compounds 1, 2, 3 and 4

Carbon No. 1 3 4

1 31.95 38.72 38.36 37.53

2 30.36 27.43 27.14 30.32

3 78.82 79.00 78.98 78.69

4 40.47 38.87 38.71

5 47.09 55.32 55.17 140.97

6 21 18.33 18.25 121.96

7 25.98 34.30 32.57 32.22

8 47.94 40.84 39.22

9 19.96 50.44 47.49

10 26.07 37.18 37.04 36.99

26.43 20.94 23.35 21.35

12 32.93 25.15 122.59 39.88

13 45.36 38.07 143.55 42.40

14 48,79 42.84 41.56

15 35.53 27.46 27.&

16 28.31 35.59 22.88 29.37

17 53.04 43.01 46.48

18 17.93 48.32 40.95 12.19

19 29.88 47.99 45.83 19.47

20 34.34 150.93 30.62

21 19。
23 29.86 33.75 21.52

22 42.91 40.01 32.39 138.23

23 74.50 28.00 28.05 129.52

24 159.21 15.37 15.50

25 29.83 16.13 15.28

26 23.15 15.99 17.09 21.35

27 25.57 14.56 25.89 19.23

28 108.11 18.01 182.94

29 25.42 109.35 33.02 12.58

30 13.99 19.32 23.53

31 19.31

Gl 102.63

G2 75.41


G4 71.77

G5 78.55

G6 62.91
ACGC ChemicalResearchCommunicationsVol. 16,2003 -Page27

We gratefully acknowledge the assistanceof ProfessorDr. R.P. Chaudhary, Cenkal Department
of Botany for the identification of the plant, and Dr. Arjun Hari Banskota, Department of Natural
Product Chemistry, Tomaya Medical and PharmaceuticalUniversity, Japan for providing spectra.
Part of this work was supported by a TWAS research grant (TW NSO joint research project
19197)to Mangala D. Manandhar and M. Iqbal Choudhary; for which the authors are thankful to
TWAS. Thanks are also due to Dean's Office, Tribhuvan University for research grant to
Mangala D. Manandhar.

1. of thefloweringplantsof Nepal;A
HaraH., ChaterA.O., WilliamsL.H.J.,An enumeration
Joint project of the British Museum(NaturalHistory) London and University of Tokyo,
Trusteeof the British Museum(NaturalHistory)MansellBook BinderaLimited; London
1982;vol 3, p200.
2. Anjum S., FarooqA., Khan M.R., PraveenJ., ChoudharyM.I.,J..Nat.
3. Atta-ur-Rahman,ChaudharyM.I., Khan M.R., ZafaiqbalM, Natural product letter, 1998;
4. Gewali
Kalouni S.K., ChoudharyM.I., ShaheenF., ManandharM.D., Atta-ur-Rahman,
M.B. andKhalid A, J. Nat.Product,2001;64,842-841.

ChatterjeeA., MukherjeeK.S., andDattaC.P.,l Ind. Chem.Soc., L966;43 (4),285-286.

Ahmed V.Q., Application of spectroscopicmethods in the structure elucidation for some

natural products, Publish in: Rahman A.R. (Editor), "Recent advance in natural product
chemistry" H.E.J Researchlnstitute of chemistry,University of Karachi, Pakistan,1987.

Lin C.N., Chung M.I., and ChiangJ.R.,Phytochemistry',1987;26(8),2381-2384.

Chang J.K., Yu C.B., Chang D.L., Katalinic J.P. and Block. T.; Indian Journal of
Chemistry,2000; 39(B), 638-642.
9. Banskota A.H.; Cytotoxic and Hepatoprotective Consituent.fro* the Leaves of Combretum
quadrangulare Kurz, 2000; 72.