Master Degree Paper1

lSSN 1020-5586

ASiAN C00RDINATING GROUP FOR CHEMiSttRY(ACGC)

CHEMICAL RESEARCH COMMUNICATIONS

VOL.16,2003

∧ UNESCO

:nternationa: Program in the Chemical ScienOes (IPiCS)

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 Java,Indonesia. ACGC CRC Editorial Board

Executive Editor Prof. StephenG. Pyne Department of Chemistry University of Wollongong Wollongong,NSW,2522 Australia

(ph)+61-2-422r3sII (fax)+61-2-42214287 (e-mail) [email protected]. 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-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 Volume16,2003 CONTENTS

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

ACGC ChemicalResearchCommunicationsVol. 16, 2003 - Page19

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

Received25'hNovember.2002

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

Introduction 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: nara@nar_ni.wlink.com.np

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

Jο 4 s レb l ′こ 2 θθg _ P a g e 2 0 t t C″″露 ο ηJ σ αι ИC G C C t t θ ″J σ α′R ♂θαr ε 3.The present study has resulted in εθ α 辟om S cο /Jα of steroidal alkaloids has also bcen reported」 the isolation of a new triterpene l along with known compounds, lupeo1 2, oleanolic acid 3,

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

Results and Discussion parts of the S ガcο αεθα was evaporated to yield a_y A methanol extract of the al ac五 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“ 198-200° C,blg+85.7°

/_7456)was iS01ated as a white crystallinc solid,m.p.

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

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 - 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― spec―

one carbons in the molecule. The DEPT 135

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,

the DEPT-135 were 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 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―

″0 “s レb i f a 2 θ θ3 - P a g e 2 1 ИC C C C 力θ“J c α ′R “ θ αr c 力σο″“z ηi C α

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

cycloartanol. The ■lethylene―

stereochcmistry at C-23 was not dete..1.ined. Compound 2(C30H500,EIMS,″ 216°C,L]『

426,M+)waS iS01ated as a whitc crystalline solid,m.p. /4‐

+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

stigmasterol-3-0-β―D‐glucopyranoside.

C.The 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 tlc). authentic salnplc(mp andCO― Compound 6 is idcntifled as betulin by companson、

m value of /ith the reported lH―

betulin 8.

Experilnental ″″′Practtts=l■lelting points werc uncorrected,and were recorded on an Gι″eraJ IhηθrliHθ electnc Sun―Vic U.K.IR‐ spectra were recordcd in KBr discs.lH― NMR(400 Ⅳ compounds l,2 and 3、

EIz)speCtra Of

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 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,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 ls were collected iom Hattiban,Kathnandu in September PJa“ 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.

.fα 2θθ3-Page 22 Sレο′ JO“ ∠CCC CJle″ご α′ cα ′Rω θ αrcたCο″″ツ4Jσ 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× dichloromethanc(??× ??m⊃ tO yield ll g and 36 g extracts respect市 he diCh10romethane ely,「

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 ith ethyl acetate in hexane. The recrystallized compound was irther pu五 fled by triturating、ア 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

″οJ`砂「 ″りた2イー ″θ `りこ c″θ9`Jaα r`α

恥h i t e c r y s t d u n e s o mh .とp . 1 9 9 ° C ; [ α] 『 + 8 5 . 7 ° C(cO.9,MCO菫 ゝR vtt cm・ :33oO,2900, NMR(CDC13,400 MHz)δ

1600,1460,1020,1000;lH―

O.948(3H,s,CH3 29),0.807(3H,s,CH3 19),0・895(3H,s,H-31),0.965

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

(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, -5),1.59,1.78(2H,H-6),1.13,1.33(2H,耳

lH,J=5.71・Iz,H-3),1.30但

-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), 20):4.210(dd,lH,」 1.38∈ I‐ (CDC13),SCe Table l;EIMS″

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

309(32),316(96),297(55),255(28),123(93). m.p.216° C;[α ]『 +52.1(`0.H,MeOHtt vtt Cm・ Z″ ″ Jの :Ⅵ唖 te crystalline soliと 2900,1640,1450,1380,1040,lH―

NMR(CDC13 400 MHz)δ

:3500,

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

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,」 5),1.405,1.521(2H,H-6),1.388,1.385(2H,H-7),1.286(H‐ 1.653(2H,H-12),1.643∈

=9.0耳 z,H―

9),1.235,1421(2H,H-11),1.078,

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),

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

Table l;EIMS″

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

189(72) d,m.p.258° C , L ] 『 + 9 7 . 0 ( σ α1 4 M c O H ) V t t C m ・ : J Ⅱn e s o Ⅱ ∠ の 「W h i C C r y 償 θ物 ″οJ l i c″ blMR (CDC13)δ

2900, 1685, 1460, 1385, 1360, lH― H-2),3.20(lH,dd,J=11.4,4Hz,H‐

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

(H-9),1.84,1.88(2H,H-11),5.26(dd,1耳

H-18),1.44,1.60(2H,H―

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

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, 30);13c_

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‐ NMR(CDC13),See Table l.

C),lH―NMR

θ の =White crystallinc compolmd;mop.(295° 0-β gレ CaFy″ ″οsJ″ StigttαsたrθJ-3‐ (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,

29),4.317(m,lH,H3-

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。

l Hz,H-23),1.882 ,H-1),

(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‐

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),

C,Rf O.63(1:5, ″′θ sJ″ θ「シ White cwstalline compollnd m.p.253° θ「 s `′ ″ル3‐ sirο ルノ“COpッ MeOH:CHC13) lH― 『 NMR(CDC13,400 MHz)δ Bα″Jli4`の 3H,H-25),0.750(s,3H,H-26),1.132(s,3H,H… 3.217(dd,lH,J=10.4,4.9 Hz,H-3α

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),

),4.681(lH,m,H29α

J=3.3,3.3 Hz,H-12),2.1818(dd,lH,J=4.0,13,7 Hz,H-18β

),4.579(lH,m,H29β

),5.277(dd,lH,

).The COmpollnd was idcntiied by

qⅣR values with reported spectra8. direct companson oflII〕 =IИethanol,dicthyl ethctt dichibromcthane,and hexane extracts of plant ss鋼ソ 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 “α・The result showed 7′お εttθ polyglacturonasc(Dinglds cup―plate method)produced by β ο′ L showed 33.33%and that thc methanol and aqucous extracts,at concentrations of l m3/100 μ

‐ ely(disulled wtter and anol meⅢ Were used as ne aCtiVity respecti、 32.14%inhibition of ellz「

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

Ｈ Ｃ

ヽ

Ｈ

Ｃ Ｙ Ｈ

鉾

，ゝ ｑ ζ

H3 ♀

CH2 C

T

へ 11 )

fIH2 Lく CH3

HOM :

A

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(H219,H2-28)andmethineprotons(H-8) depictedasalrolv\rs.

ACGC ChemicalResearchCommunicationsVol. 16, 2003 -Page25 へ ３ ３ ︲ ］ ０ 〓 〓 一 三

︲／

lH Chemicalshift mm COSY

4 210 dd 4.64)

ま 尉:)

6/脚

13c chemicalshift from 2D‐NMR analyses

Fig. 3 lH 1fromCOSY)and

r3Cassignments of compoundI by 2D-NMR.

ぽ CH3 ぼ H20

ヽ _

ぽ ‐ 2い CH3 _ :a―

卜H20

-卜

z/_7123(93)

4/_7255(28)

r H20 H20ヽ e

7_‐297(55)

ぽ ‐ 20 H2∝ L 耐 C3H7 H20ヽ

″ノz441(17) H/z438(100) ″ノン423(69) 4/_7420(16)

励を40520) z/z 395(35)

″ν2316(96) C22H360

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

ACGC ChemicalResearchCommtuications Vol. 16' 2003 -Page26 13C-NIr4R, Table I Chemical Shift Data (ppm) of compounds 1, 2, 3 and 4 り´

3

4

Carbon No.

1

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

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

30

13.99

19.32

23.53

31

19.31

29.37

12.58

Gl

102.63

G2

75.41

G3

G4

71.77

G5

78.55

G6

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, 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.

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