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ASiAN C00RDINATING GROUP FOR CHEMiSttRY(ACGC)

CHEMICAL

RESEARCH

COMMUNICATIONS

UNESCO

VOL.16,2003

:nternationa:

Program in the Chemical ScienOes

(IPiCS)

findexed andAbstractedbyChemicalAbstracts]

ACGC ChemicalResearchCommunications

Cover page:The coverpageincludesthe structureof thealkaloid 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 Java,Indonesia.

ACGC CRC Editorial Board

Executive Editor Prof. StephenG. Pyne Departmentof Chemistry University of Wollongong

Wollongong,NSW,2522

Australia

(ph)+61-2-422r3sII

(fax)+61-2-42214287

(e-mail) Stephen_Pyne@uow.edu.au

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

Scientific Advisory Board Prof. HajimeAkimoto (Japan) Dr. DayarArbain (lndonesia) Prof. David St.C. Black (Australia) Prof. LourdesJ. Cruz (Philippines) Prof V. G. Kumar Das(Malaysia) Dr. R. Liminga (Sweden) Dr. Neville Marchant (Australia) Dr. HermannNiemeyer (LANBIO) Prof. Min Bo Chen(China) Dr. SurachaiNimgirawath (Thailand) Dr. Mohan Perera(UNESCO,New Delhi)

Dr.

Prof. Vichai Reutrakul (Thailand)

Prof. SangChul Shim (Korea) Dr. T. H. Spurling(Australia) Prof. W. C. Taylor (Australia) Prof. Prapin Wilairat (Thailand) Prof. Won Sik Woo (Korea)

T. Ramasami(CLzu Madras, India)

ACGC

ChemicalResearchCommunications

Volume16,2003

CONTENTS

Sediment Accretion

Kuantan Mangrove ForestoMalaysia

and Trace Metal Concentrations in the Surface Sedimentsof

Kamaruzzaman,B. Y.,Jamil, B. T. and Hasrizal, S.

Sesquiterpenesand Triterpenes from SonchusOleraceus(Asteraceae)

HeshamR. El-Seedi

14

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,andAtta-ur-Rahman

Chemical Components of M elastoma malabathricum

28

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

Unusual Oxygenated Cations in Electrospray Ionisation Mass Spectroscopyof Polyprenols from Jatropha curcasL.

34

John A Rideout, ConsolacionRagasa,and Hiu Tian Ngo

Secondary Metabolites from Jasminum Sambac and.CanangaOdorata

40

ConsolacionY.Ragasa,Benjie G. Tamboong,andJohnA. Rideout

The Chemical Constituents of Macaranga triloba

48

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

Geochemistry of SomeHeavy Metals in Sediment Cores from Setiu Mangrove Forest, Terengganu, Malaysia

53

KamaruzzamanBin Yunus

Structure and Characterizationof SomeNew Coordination Compoundsof Organotin(IV) with Schiff Bases

62

NavneetKaur, H. L. Singh,S. VarshneyandA. K. Varshney

Hydroxy Betulinic Acid from the Leavesof OrtltosiphonStamineus

M. AmzadHossain,andZhari Ismail

Rapid

alkaline or in neutral medium.

H. N. Roy, A. M. Paul and M. S. Sarkar

Synthesis of a model chrymutin

like

compound and its derivatization

69

in weak

74

ACGC ChemicalResearchCommunicationsVol. 16,2003 - Page19

23-Hydroxy-24-methylenecycloartanol,a new cycloartane triterpenoid from the aerial parts of Sarcococca coriaceaof Nepaleseorigin

A{un Paudel,fNarayanP. 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 PharmaceuticalUniversity, Machida, Tokyo 194-8543,

Japan.s

Received25'hNovember.2002

Abstract

A new triterpenoid, 23-hydroxy-24-methylenecycloartanol,and the known compounds,lupeol,

oleanolic acid, stigmasterol-3-O-B-glucopyranosideand sitosterol-3-O-B-glucopyranosideand

betulin, were isolatedfrom the aerialpartsof Sarcococcacoriacea (Hook. F.) Sweet(Buxaceae).

Their structures were assignedon the basis of spectral data. The dichloromethane extract was

found cytotoxic while the methanolextract showed enzpe inhibition of polygalacturonase.

Keylvords:Sarcococcacoriacea(Hook. F.) Sweet;Aerial parts;Triterpenoid

Introduction

Sarcococcacoriacea (Hook. F.) Sweet,Buxaceaeris an evergreenshrub widely distributedin the

of Nepal. The plant has exhibited antibacterial,

Mahabharat range of Himalayan Kingdom

anticholinesterase,antitumor, antiulcer and ganglion blocking' properties. Different parts of the

plant are harnessedin the treatmentof fever and rheumatism in traditional medicine.' A number

*

To whom correspondenceshould be addressedTel: 977-01-332034,977-01-260384Email:

nara@nar_ni.wlink.com.np

i

t

$

Central Departmentof Chemistry,Tribhuvan University, Kathmandu, Nepal,

H.E.J ResearchLrstitute of Chemistry,lnternational Centerfor Chemical Sciences,University of Karachi, Karachi-75270, Pakistan

Sho*a PharmaceuticalUniversity, Machida, Tokyo 194-8543,Japan

ИCGC CttθJσαRθαrεtt Cο″″露ηJσαιJο4sレbl′こ 2θθg_Page 20

of steroidal alkaloids has also bcen reported」辟om S cο /Jαεθα 3.The present study has resulted in the isolation of a new triterpene l along with known compounds, lupeo1 2, oleanolic acid 3,

stittasterol-3-0-β

glucOpyranoside 4,β

sitOSterol-3-0-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 alac五parts of the Sガcοαεθαwas evaporated to yield a_y 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.

198-200°C,blg+85.7°

(60.9,veoH) The R spectmm displayed absorp■ons江 3400(OH),

2900(CH),1600(olCin),1020(C―

O)Cm‐ 1.EIMS ga /e a molecular ion pcak at

/_-456

(C31H5202)and the peak at /z441 ducto M+― CH3 The base peak at″ ル 438 was due to the loss

ofwater iom M+.The peaks at〃/_-423,420,405 and 395 were assignedH20~CH31',[M~for[M―

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,

which was irthcr supported NMR.Sixby lH‐

assigned as quatemary.

peaks for carbon missing魚 )m the DEPT-135 were

The partial structures forngs 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

cycloartane triterpenOid /ith an extra sidechain carbon,as depictOd in Fig.4. On the basis of

ИCCC C力θ“Jcα′R“θαrc力σο″“zηiCα″0“sレbi fa 2θθ3-Page 21

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

■lethylene―cycloartanol. The

stereochcmistry at C-23 was not dete

1.ined.

Compound 2(C30H500,EIMS,

/4426,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

crystallinc solid,m.p.295°C. From IR― and 2E)―NNIIR―spectra, and companson with reportOd

spectral data7,8 and an authentic sample(mmp and CO―

stigmasterol-3-0-β D‐ glucopyranoside.

tlc),the cOmpound was assigned as

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

compollnd was assigned as sitostcrol-3-0-β ― glucOpyranoside by dircct comparison with authentic salnplc(mp andCO―tlc).

Compound 6 is idcntifled as betulin by companson、

betulin 8.

Experilnental

/ith the reported lH―m value of

GιeraJ IhηθrliHθPracttts=llelting points werc uncorrected,and were recorded on an

electnc SunVic U.K.IR spectra were recordcd in KBr discs.lH― NMR(400 Ⅳ

compounds l,2 and 3 rere recorded on JEOL― ЛlLA 400WB spectromcter. 13c_NNER spectra

EIz)speCtra Of

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

Hz.The mass spectra were recorded on a JEOL―

are ven in

」NIS―D300 14ass spectrolneter.Pre―coated TLC

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

PJars Ma″rliaJs「The plant mate五als 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′RωθαrcたCο″″ツ4Jσα′JO“Sレο′.fα 2θ θ3-Page 22

Erracο α“J ttοこ面 o″=Air‐dried,pOwdered plant― matenals(l kg)Were perc01ated in

methanol(3×10L )at r00m temperature for 48 hours for each extract.The methanol ex

concentrated under reduced pressllre to Obtain a viscous residuc(340g).Distilled dark red― water

(200 mtt Was added,and the residuc extracted with hexane(5×200 mL)f0110Wed by

dichloromethanc(??×??m⊃ tO yield ll g and 36 g extracts respect市 ely,he diCh10romethane

extract(20.36g)was ChrOmatographed on a silica column eluted with hexane/cthyl acetat

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

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 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 ″ た 2イ ー ″θ`りこc″θ 9`Jaα r`α″οJ`砂「

恥hite crystdune sohとm.p.199°C;[α ] +85.7°C(cO.9,MCO菫 R vtt cm・ :33oO,2900,

1600,1460,1020,1000;lH

NMR(CDC13,400 MHz)δ

30),0。329(d,lH,J=4.O Hz,H-19),0.547(d,lH,J=4.O Hz,H‐

O.948(3H,s,CH3~29),0.807(3H,s,CH3~

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=5.71Iz,H-3),1.30 -5),1.59,1.78(2H,H-6),1.13,1.33(2H,耳

-7),1.50(H-8),1.10,1.99

(2H,H-11),1.63,1.63(2H,H-12),1.28,1.28(2H,H-15),1.10,1.98(2H,H-16),1.66(H-17),

1.38 I20):4.210(dd,lH,

=6 2,6.4 Hz,H-23),2.319(lH,dq,J=6.4 Hz,H-25);13c_NMR /z[ 凋 +456(29),438(100),423(69),420(16),405(20),395(35),

(CDC13),SCe Table l;EIMS″

309(32),316(96),297(55),255(28),123(93).

Z″ Jの :Ⅵ唖 te crystalline soliとm.p.216° C;[α ] +52.1(`0.H,MeOHtt vtt Cm・

2900,1640,1450,1380,1040,lH

NMR(CDC13 400 MHz)δ

O.966(3H,s,H-23),0.759(3H,s,

:3500,

H-24),0.828(3H,s,H-25),1.029(3H,s,H-26),0.943(3H,s,H-27),0.787(3H,s,H-28),4.562

(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 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‐

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

18),

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

Table l;EIMS″

189(72)

[M+],426(100),411(25),408(21),393(12),365(23),218(50),207(75),

θ οJlic WhiC CryJne soⅡd,m.p.258°C,L]『 +97.0(σα14 McOH)Vtt Cm・ :

2900, 1685, 1460, 1385, 1360, lH

H-2),3.20(lH,dd,J=11.4,4Hz,H

blMR (CDC13)δ

O・95,1.58(2H, H-1),1.54,1.54(2H,

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

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

,J=3.7,3.7 Hz,H-12),1.04,1.69(2H,H-15),1.58,

H-18),1.44,1.60(2H,H―

19),1.20,1.33(2H,H-21),1.56,1.74(2H,H-22),0.96(3H,H-23),0.75(s,3H,H-24),0.89(s,

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.

StigttαsrθJ-30-β g CaFy οsJθ =White crystallinc compolmd;mop.(295°

C),lH―NMR

(500 IIz)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‐

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

(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

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

29),4.317(m,lH,H3-

l Hz,H-23),1.882

,H-1),

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),

sirοs`3θ COpθsJθ White cwstalline compollnd m.p.253°C,Rf O.63(1:5,

MeOH:CHC13)

BαJli4` lH NMR(CDC13,400 MHz)δ

3H,H-25),0.750(s,3H,H-26),1.132(s,3H,H…

O.985(s,3H,H-23),0,773(s,3H,H-24),0.913(s,

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

direct companson oflIIqR values with reported spectra8.

Briιsrtmp bliaαss =IИethanol,dicthyl ethctt dichibromcthane,and hexane extracts of plant

were suttected tOncshrimpb bioassay.The bioassay showed that the dichloromethane

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 7′ εttθαThe result showed that thc methanol and aqucous extracts,at concentrations of l m3/100 μ L showed 33.33%and

32.14%inhibition of ellz「ne aCtiVity respecti、 ely(disulled wtter and anolmeⅢ 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 dichloromethanewas usedascontrol).

Fig. I Structuresof isolatedcompounds

T

HOM~:

11 )

A

fIH2Lく CH3

H3

ζ

C

CH2

of 7.14o/oonly (pure

Fig. 2 Partial structureof compound1 solved by HMBC data. Two and three bond C-H correlationsfrom methyl protonsareshownin bold linesandthosefrom methyleneprotons(H2-

19,H2-28)andmethineprotons(H-8)depictedasalrolv\rs.

ACGC ChemicalResearchCommunicationsVol. 16,2003 -Page25

lH Chemicalshift mm COSY

‐3

6/

4 210 dd

4.64)

ま尉:)

13c chemicalshift from 2D‐ NMR analyses

Fig.3 lH 1from COSY)and r3C assignmentsof compoundI by 2D-NMR.

z/_7123(93)

4/_7255(28)

:a―

H20

-卜

e

~CH3

~H20

_

2 CH3 _

r~H20~H20ヽ

ぽ ‐ 20~H2∝ L

~C3H7~H20ヽ

″ノz441(17)

H/z438(100)

″ノン423(69)

4/_7420(16)

励を40520)

z/z 395(35)

7_‐297(55)

″ν2316(96)

C22H360

Fig. 4 MS fragmentationpattern of compound 1. Relative intensities areshown in parenthesis.

ACGC ChemicalResearchCommtuications Vol. 16' 2003 -Page26

Table I - 13C-NIr4R, Chemical Shift Data (ppm) of compounds1, 2, 3 and 4

CarbonNo.

1

1

31.95

2

30.36

3

78.82

4

40.47

5

47.09

6

21

7

25.98

8

47.94

9

19.96

10

26.07

26.43

12

32.93

13

45.36

14

48,79

15

35.53

16

28.31

17

53.04

18

17.93

19

29.88

20

34.34

21

19。23

22

42.91

23

74.50

24

159.21

25

29.83

26

23.15

27

25.57

28

108.11

29

25.42

30

13.99

31

19.31

Gl

G2

G3

G4

G5

G6

´

3

4

38.72

38.36

37.53

27.43

27.14

30.32

79.00

78.98

78.69

38.87

38.71

55.32

55.17

140.97

18.33

18.25

121.96

34.30

32.57

32.22

40.84

39.22

50.44

47.49

37.18

37.04

36.99

20.94

23.35

21.35

25.15

122.59

39.88

38.07

143.55

42.40

42.84

41.56

27.46

27.&

35.59

22.88

29.37

43.01

46.48

48.32

40.95

12.19

47.99

45.83

19.47

150.93

30.62

29.86

33.75

21.52

40.01

32.39

138.23

28.00

28.05

129.52

15.37

15.50

16.13

15.28

15.99

17.09

21.35

14.56

25.89

19.23

18.01

182.94

109.35

33.02

12.58

19.32

23.53

 

102.63

75.41

71.77

78.55

62.91

ACGC ChemicalResearchCommunicationsVol.16,2003 -Page27

'; .1

Acknowledgement

We gratefully acknowledge the assistanceof ProfessorDr. R.P. Chaudhary, Cenkal Department

of Botany for the identification of the plant, andDr. Arjun Hari Banskota, Department of Natural

Product Chemistry, Tomaya Medical andPharmaceuticalUniversity, Japanfor providing spectra.

Part of this work was supported by a TWAS researchgrant (TW NSO joint

researchproject

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.

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