A New Lignan fromElaeagnus lanceolata (Elaeagnaceae)

2010·0.78 MB·

by  Song Wei-Wu-

云 南 植 物 研 究 , ():
暋2010 325 455~462
ActaBotanicaYunnanica : /
暋暋暋暋暋暋暋暋暋暋暋暋暋暋暋暋暋暋DOI10灡3724SP灡J灡1143灡2010灡10112
披针叶胡颓子中的一个新木脂素
*
宋卫武 ,,李 波**,刘吉开
12 1 1
暋
中国科学院昆明植物研究所 植物化学与西部植物资源持续利用国家重点实验室 云南 昆明
(1 , 暋650204;
中国科学院研究生院 北京
2 , 暋100049)
摘要:从披针叶胡颓子 的干燥枝叶中分离得到 个化合物 其中
(Elaeagnuslanceolata) 19 , isoamericanol
为一新化合物 经波谱学方法鉴定其结构为
B(1) , rel灢(7曚Z)灢(7毬,8毩)灢3灢methoxy灢4,9曚灢dihydroxy灢3曚,7灢ep灢
oxy灢8,4曚灢oxyneolign灢7曚灢ene。
关键词:披针叶胡颓子 木脂素
; ;isoamericanolB
中图分类号: 文献标识码: 文章编号:
Q946暋暋暋暋 暋暋 A暋暋暋暋 暋暋暋 0253灢2700(2010)05灢455灢08
ANewLignanfromElaeagnuslanceolata Elaeagnaceae
( )
1,2 1** 1
SONGWei灢Wu ,LIBo ,LIUJi灢Kai
(1StateKeyLaboratoryofPhytochemistryandPlantResourcesinWestChina,KunmingInstitute
ofBotany,ChineseAcademyofSciences,Kunming650204,China;2GraduateUniversity
ofChineseAcademyofSciences,Beijing100049,China)
Abstract
:Anewcompound,namelyisoamericanolB(1),togetherwith18knowncompoundswereisolated
fromthedryleavesandtwigsofElaeagnuslanceolata.Thestructureof1wasdeterminedtoberel灢(7曚Z)灢
(7毬,8毩)灢3灢methoxy灢4,9曚灢dihydroxy灢3曚,7灢epoxy灢8,4曚灢oxyneolign灢7曚灢eneonthebasisofdetailedspectroscop灢
icanalysis.
Keywords
:Elaeagnuslanceolata;Lignan;isoamericanolB
暋 Elaeagnuslanceolata Warb.exDielsbe灢 leavesofthisplantbefore(Caoetal灡,2001).
longstothegenusElaeagnus (Elaeagnaceae), Aspartofourongoingprogramondiscovering
whichcomprisesabout80speciesand wide灢 naturalskincareproductsfromTraditionalChi灢
spreadinsubtropicalandtemperateareasofEast neseMedicine,athoroughchemicalworkwas
andSoutheastAsia,amongthem55speciesare carriedoutonthisplant.Anewlignan,isoame灢
foundinChina(EditorialBoardofFloraofChi灢 ricanolB (1),togetherwith18knowncom灢
naofChinese AcademyofSciences,1979). poundswereisolatedfromthedryleavesand
Leaves,fruits,androotsofE灡lanceolatahave twigsofE灡lanceolata.These known com灢
beenusedtotreatcough,asthma,dysenteryand poundswereidentifiedtobe6灢hydroxy灢3,4灢di灢
congestion(EditorialBoardofNationalHerbal hydro灢1灢oxo灢毬灢carboline(2),2毩灢hydroxy灢ursolic
Compendium,1975).Fourflavonolglycosides acid (3),2毩,23灢dihydroxy灢ursolicacid (4),
andaphenylpropanoidwerereportedfromthe maslinicacid (5),vomifoliol (6),roseoside
* Foundationitems:FoundofStateKeyLaboratoryofPhytochemistryandPlantResourcesinWestChina(P2008灢ZZ14),andthe
NaturalScienceFoundationofYunnanProvince(2007C091M)
** Authorforcorrespondence;E灢mail:libo@mail灡kib灡ac灡cn;Tel:+86灢871灢5223321
Receiveddate:2010灢05灢27,Accepteddate:2010灢06灢28
作者简介 宋卫武 男 在读硕士研究生 主要从事天然药物化学研究
: (1983-) , , 。
云 南 植 物 研 究 第 卷
4暋56暋暋暋暋暋暋暋暋暋暋暋 暋暋暋暋暋暋暋 暋 暋 暋 暋 暋 暋暋暋暋暋暋暋暋暋暋暋暋暋暋暋暋 32
(7),syringaresinol(8),clemaphenolA(9),ja灢
ponicaacid(10),lutein(11),trilobatin(12),
3灢phenyl灢1灢(2曚,6曚灢dihydroxy灢phenyl灢4曚灢O灢毬灢
D灢glucopyranosyl)灢1灢propanone (13),narin灢
genin灢7灢O灢毬灢D灢glucopyranoside (14),vitexin
(8灢C灢毬灢D灢glucopyranosylapigenin)(15),7灢
O灢毬灢D灢glucopyranosylchrysin(16),isorham灢
netin3灢O灢毩灢L灢rhamnopyranosyl灢7灢O灢毬灢D灢gluc灢
opyranoside(17),kaempferol灢3灢O灢毬灢D灢gluco灢
pyranoside(18)andkaempferol灢3灢O灢毬灢D灢(6曞灢
O灢trans灢p灢coumaroyl)glucopyranoside (19)
(Fig灡1,2).Compounds2灢17wereisolatedfrom
thisplantforthefirsttime.Here,wereported
theisolationandstructureelucidationofthenew
compound.
ResultsandDiscussion
IsoamericanolB(1),wasobtainedascolor灢
lessamorphoussolid,whichwasshowntopos灢
sessamolecularformulaasC19H20O5bypositive
+
HR灢ESI灢MSat m/z351灡1205 [M + Na]
+
(calcd.forC19H20O5Na ,351灡1208),indica灢
tingtendegreesofunsaturation.TheIRspec灢
trumshowedabsorptionsat3432,1580,1505
cm灢1,suggestingthepresenceofhydroxylgroup,
Fig灡1暋Structuresofcompounds2-11
doublebondandaromaticmoiety.
Fig灡2暋Structuresofcompounds12-19
期
5 暋暋暋暋暋暋SONGWei灢Wuetal灡:ANewLignanfromElaeagnuslanceolata(Elaeagnaceae)暋暋暋暋暋暋45暋7
13
暋暋Inthe C灢NMRspectrumof1(Table1), transdouble bond and one hydroxymethylin
19carbonsignalswereobserved,includingone isoamericanolA(Fig灡4).
methyl(毮C13灡6),onemethoxy(毮C56灡4),one Therelativestereochemistryof1wasdeter灢
oxygen灢bearingmethylene(毮C60灡0),twooxy灢 minedbythecorrelationbetweenH灢9andH灢7,
gen灢bearingmethines(毮C74灡3,78灡5),aswell observedintheROESYspectrumof1,which
aseightaromaticmethinesandsixquaternary establishedthetrans灢relationshipbetweenH灢7
aromaticcarbons,whichbelongtotwophenyls andH灢8.Thus,thestructureof1waselucida灢
andonedisubstituteddoublebond(Table1). tedasrel灢(7曚Z)灢(7毬,8毩)灢3灢methoxy灢4,9曚灢di灢
1
The H灢NMRsignalsat毮H4灡33(dd,J=6灡3, hydroxy灢3曚,7灢epoxy灢8,4曚灢oxyneolign灢7曚灢ene.
1灡6),5灡72(dt,J=11灡9,6灡3),and6灡42(d,
J=11灡7),13CNMRsignalsat毮C60灡0 (t), Experimental
131灡4(d),and130灡8(d)indicatedthepresence Generalexperimentalprocedures
暋Opticalrotation
ofone(Z)allylalcoholunit,whichwasalso wasmeasuredonaJASCOP灢1020digitalpolarimeter.IR
confirmedbyCOSYspectrum.IntheHMBC spectrawereobtainedfromBrukerTensor27FT灢IRspec灢
spectrum,correlationsbetweenH灢9andC灢8,C灢 trometerwithKBrpellets.UVspectraweredetermined
7,H灢8andC灢4曚,H灢7andC灢3曚,C灢1,C灢2,C灢6 onaShimadzu UV2401PCspectrometer.ESIMSand
HRESIMSspectrawererecordedonAutoSpecPremier
confirmedthestructurefragmentofbenzodiox灢
P776andAPIQSTARPulsarinstrument.NMRspectra
ane.Further 2D NMR spectra data analysis
wererecordedonBrukerAM灢400andDRX灢500spectrom灢
(HSQC,COSY,andHMBC)suggestedthatcom灢
eterswithTMSasinternalstandard.Silicagel(200-300
pound1possessaneolignanskeleton,whichwas
mesh),SilicagelF254 (QingdaoMarineChemicalCo.,
composedoftwophenylpropanoidsunitsconnected Ltd),RP灢18silicagel(40-63毺m,Merck,Germany),
1 13
bya1,4灢dixoanering(Fig灡3).The Hand C MCIgelCHP灢20P(75-150毺m,MitsubishiChemical
NMRspectradataof1wereverysimilartothoseof Corporation,Tokyo)andSephadexLH灢20(Pharmacia)
isoamericanolA(Waibeletal灡,2003),exceptfor wereusedforcolumnchromatography.Fractionswere
thepresenceofoneadditionalmethoxy,onecis monitoredbyTLCandspotswerevisualizedbyheating
doublebond,andonemethylin1,insteadofone silicagelplatesimmersedwith10% H2SO4inethanol.
Table1暋1Hand13CNMRdateof1andisoamericanolAinCD3OD(毮inppm,JinHz)
1 IsoamericanolA
NO. 毮Ca) 毮Hb) 毮Cc) 毮Hd)
1 129灡7(s) 129灡6(s)
2 111灡1(d) 6灡96(d,1灡6) 115灡6(d) 6灡85(d,2灡5)
3 149灡0(s) 146灡6(s)
4 147灡5(s) 147灡1(s)
5 118灡1(d) 6灡83(overlap) 116灡4(d) 6灡80(d,8灡5)
6 120灡3(d) 6灡84(overlap) 120灡4(d) 6灡76(dd,8灡5,2灡5)
7 78灡5(d) 5灡08(d,2灡5) 77灡6(d) 4灡80(d,8)
8 74灡3(d) 4灡50(dq,6灡7,2灡5) 80灡0(d) 3灡98(ddd,8,5灡5,3)
9 13灡6(q) 1灡03(d,6灡7) 62灡1(t) 3灡47(dd,12灡5,5灡5);3灡66(dd,12灡5,3)
1曚 131灡6(s) 132灡0(s)
2曚 118灡4(d) 6灡84(overlap) 115灡6(d) 6灡95(d,2灡5)
3曚 144灡2(s) 144灡6(s)
4曚 142灡9(s) 145灡3(s)
5曚 116灡1(d) 6灡82(overlap) 117灡9(d) 6灡88(d,8灡5)
6曚 123灡6(d) 6灡74(dd,8灡2,2灡0) 120灡8(d) 6灡92(dd,8灡5,2灡5)
7曚 130灡8(d) 6灡42(d,11灡7) 131灡4(d) 6灡48(br灡d16)
8曚 131灡4(d) 5灡72(dt,11灡9,6灡3) 128灡1(d) 6灡20(dt,16,6)
9曚 60灡0(t) 4灡33(dd,6灡3,1灡6) 63灡8(t) 4灡18(dd,6,1灡5)
OMe 56灡4(q) 3灡79(s)
a)125Hz;b)500Hz;c)90Hz;d)360Hz.
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4暋58暋暋暋暋暋暋暋暋暋暋暋 暋暋暋暋暋暋暋 暋 暋 暋 暋 暋 暋暋暋暋暋暋暋暋暋暋暋暋暋暋暋暋 32
Plantmaterial
暋暋 暋TheleavesandtwigsofElaeagnus obtainedascolorlessamorphoussolid,C19H20O5;UV
lanceolata werecollectedin YimencountyofYunnan 毸mMaexOH (log毰):286灡4 (3灡76),259灡4 (4灡05),216
Province,China,inSeptember,2008,andidentifiedby (4灡44),204 (4灡59)nm;[毩]2D4=+98灡1 (c=0灡4,
Prof.ChenYu,KunmingInstituteofBotany,Chinese MeOH);IR毻KmBaxr (cm灢1):3432,2925,2852,1612,
AcademyofSciences.Avoucherspecimenwasdeposited 1580,1505,1463,1429,1380,1267;1Hand13C灢NMR:
intheStateKeyLaboratoryofPhytochemistryandPlant seeTable1;ESI灢MS(positive)m/z:351[M+Na]+,
ResourcesinWestChina,KunmingInstituteofBotany, HR灢ESI灢MS(positive)m/z:351灡1205 [M+Na]+
ChineseAcademyofSciences. (calcd.forC19H20O5Na+,351灡1208).
Extractionandisolation
暋Theair灢driedleavesand 6灢hydroxy灢3,4灢dihydro灢1灢oxo灢毬灢carboline (2)was
twigs(7kg)ofElaeagnuslanceolatawereextractedwith obtainedasyellowpowder,C11H10N2O2;1H灢NMR(CD3
methanolatroomtemperature(4暳40L).Theextracts OD,500MHz):毮H7灡27(1H,d,J=8灡8,H灢8),6灡90
werecombinedandconcentrated,andtheresiduewasdis灢 (1H,d,J=2灡3,H灢5),6灡84(1H,dd,J=2灡3,8灡8,
solvedinMeOH/H2O(9暶1),andthensuccessivelypar灢 H灢7),3灡61(2H,t,J=7灡0,H灢3),2灡93(2H,t,J=
titionedwithpetroleumether,chloroformandn灢BuOH. 7灡0,H灢4);13C灢NMR (CD3OD,100MHz):毮C165灡0
Thepetroleumetherextract(149g)wassubjectedtocol灢 (s,C灢1),42灡8(t,C灢3),21灡5(t,C灢4),104灡2(d,C灢
umnchromatographyoversilicagel(CHCl3/MeOH100 5),152灡2(s,C灢6),116灡8(d,C灢7),114灡0(d,C灢8),
暶0曻90暶10)toafford3fractions.Columnchromatog灢 134灡2(s,C灢9a),127灡9(s,C灢8a),127灡0(s,C灢4b),
raphyofFraction2oversilicagel(CHCl3/acetone30暶1 120灡2(s,C灢4a).(Salmounetal灡,2002)
曻7暶3)afforded11(30mg).Thechloroformextract 2毩灢hydroxy灢ursolicacid(3)wasobtainedaswhite
(198g)wassubjectedtocolumnchromatographyover powder,C30H48O4;ESI灢MSm/z:495[M+Na]+;1H灢
silicagel(CHCl3/MeOH100暶0曻70暶30)toafford6 NMR(Pyridine灢d5,500MHz):毮H5灡46(1H,br灡s,H灢
fractions A灢F.Fraction B wasrepeatedlychromato灢 12),4灡10(1H,ddd,J=9灡2,9灡2,4灡1,H灢2),3灡40
graphedoversilicagel(CHCl3/acetone30暶1曻7暶3or (1H,d,J=9灡2,H灢3),1灡27(3H,s,H灢23),1灡20
petroleumether/Acetone9暶1曻7暶3orpetroleumether/ (3H,s,H灢27),1灡07(3H,s,H灢24),1灡04(3H,s,H灢
EtOAc9暶1曻7暶3),MCIgel(MeOH/H2O5暶5曻10暶 25),0灡98(3H,d,J=5灡9,H灢29),0灡97(3H,s,H灢
0),SephadexLH灢20(MeOH)andRP灢18(MeOH/H2O 26),0灡95(3H,d,J=5灡9,H灢30);13C灢NMR(Pyri灢
30暶70曻100暶0)toafford8(20mg),10(5mg)and9 dine灢d5,100MHz):毮C48灡0(t,C灢1),68灡6(d,C灢2),
(20mg).Inthesameway,2(10mg),3(60mg),4(10 83灡8(d,C灢3),39灡9(s,C灢4),55灡9(d,C灢5),18灡8(t,
mg),5(65mg)and6(18mg)wereisolatedfromFrac灢 C灢6),33灡5(t,C灢7),40灡0(s,C灢8),48灡1(d,C灢9),
tionC;1(12mg),13(10mg),14(20mg),16(50 38灡4(s,C灢10),23灡7 (t,C灢11),125灡5 (d,C灢12),
mg),18(45mg)and19wereobtainedfromFractionD; 139灡3(s,C灢13),42灡5(s,C灢14),28灡6(t,C灢15),24灡9
12(369)wasfromFractionE;7(10mg),17(6mg) (t,C灢16),48灡0(s,C灢17),53灡5(d,C灢18),39灡4(d,C灢
and15(50mg)werefromthen灢BuOHextract(296g). 19),39灡5(d,C灢20),31灡1(t,C灢21),37灡4(t,C灢22),
isoamericanolB(1,rel灢(7曚Z)灢(7毬,8毩)灢3灢methoxy灢 29灡4(q,C灢23),17灡5(q,C灢24),17灡0(q,C灢25),17灡7
4,9曚灢dihydroxy灢3曚,7灢epoxy灢8,4曚灢oxyneolign灢7曚灢ene)was (q,C灢26),23灡9(q,C灢27),179灡9(s,C灢28),17灡5(q,
期
5 暋暋暋暋暋暋SONGWei灢Wuetal灡:ANewLignanfromElaeagnuslanceolata(Elaeagnaceae)暋暋暋暋暋暋45暋9
C灢29),21灡4(q,C灢30).(Kimetal灡,2005) O8;ESI灢MSm/z:385[M灢H]+;1H灢NMR(CD3OD,
2毩,23灢dihydroxy灢ursolicacid(4)wasobtainedas 500MHz):毮H1灡03(3H,s,Me毩灢C5),1灡04(3H,s,
whiteamorphouspowder,C30H48O5;ESI灢MSm/z:511 Me毬灢C5),1灡29(3H,d,J=6灡3,H灢4曚),1灡92(3H,d,
[M+Na]+;1H灢NMR (Pyridine灢d5,500 MHz):毮H J=1灡2,Me灢C3),2灡14(1H,d,J=16灡8,H灢6毬),2灡52
5灡45(1H,t,J=4灡0,H灢12),3灡91(1H,d,J=11灡0, (1H,d,J=16灡8,H灢6毩),3灡14灢3灡86(5H,m,H灢2曞,
H灢23毩),3灡74(1H,d,J=11灡0,H灢23毬),2灡59(1H, 6曞),4灡34(1H,d,J=7灡8,H灢1曞),4灡42(1H,m,H灢
d,J=11灡6,H灢18),1灡12(3H,s,H灢27),1灡04(3H, 3曚),5灡85(1H,s,H灢2曚),5灡86(1H,br灡s,H灢1曚),5灡87
s,H灢25),0灡98(3H,s,H灢26),0灡94(3H,d,J=6灡4, (1H,m,H灢2);13C灢NMR (CD3OD,125 MHz):毮C
H灢30),0灡91(3H,d,J=6灡4,H灢29),0灡85(3H,s,H灢 201灡2(C灢1),127灡1(d,C灢2),167灡3(C灢3),80灡0(C灢
24);13C灢NMR(Pyridine灢d5,125MHz):毮C43灡8(t,C灢 4),42灡4(t,C灢5),50灡6(C灢6),131灡5(d,C灢1曚),135灡2
1),66灡5(d,C灢2),79灡1(d,C灢3),42灡8(s,C灢4),43灡0 (d,C灢2曚),77灡2(d,C灢3曚),21灡1(C灢4曚),102灡7(d,C灢
(d,C灢5),18灡5(t,C灢6),33灡4(t,C灢7),39灡7(s,C灢8), 1曞),75灡2(d,C灢2曞),78灡0(C灢3曞),71灡6(d,C灢4曞),78灡0
48灡3(d,C灢9),38灡6(s,C灢10),24灡0(t,C灢11),125灡8 (d,C灢5曞),62灡7(t,C灢6曞),24灡6(q,Me毩灢C5),23灡4(q,
(d,C灢12),139灡6(s,C灢13),42灡2(s,C灢14),28灡9(t, Me毬灢C5),19灡5(q,Me灢C3).(AnderssonandLundgren,
C灢15),25灡1(t,C灢16),48灡3(s,C灢17),53灡8(d,C灢 1988)
18),39灡7(d,C灢19),40灡3(d,C灢20),31灡3(t,C灢21), syringaresinol(8)wasobtainedaswhiteamorphous
37灡7(t,C灢22),71灡5(t,C灢23),18灡0(q,C灢24),17灡8 powder,C22H26O8;ESI灢MSm/z:419[M+H]+;1H灢
(q,C灢25),17灡8(q,C灢26),24灡1(q,C灢27),180灡2(s, NMR(CDCl3,500MHz):毮H6灡57(4H,s,H灢2曚,6曚,
C灢28),17灡4(q,C灢29),21灡7(q,C灢30).(Fangetal灡, 2曞,6曞),4灡72(2H,d,J=3灡8,H灢2,6),4灡28灢3灡89
2008) (4H,m,H灢4,8),3灡88(12H,s,4暳OMe),3灡11灢3灡05
maslinicacid(5)wasobtainedaswhiteamorphous (2H,m,H灢1,5);13C灢NMR(CDCl3,125MHz):毮C
powder,C30H48O4;1H灢NMR(Pyridine灢d5,500MHz): 147灡1(s,C灢3曚,5曚,3曞,5曞),134灡3(s,C灢4曚,4曞),132灡0
毮H5灡48(1H,br灡s,H灢12),4灡12(1H,ddd,J=11灡2, (s,C灢1曚,1曞),102灡7(d,C灢2曚,2曞),86灡0(d,C灢2,6),
9灡4,4灡1,H灢2),3灡41(1H,d,J=9灡4,H灢3),1灡29, 71灡7(t,C灢4,8),56灡3(q,2暳OMe),54灡3(d,C灢1,
1灡27,1灡09,1灡03,1灡01,0灡99,0灡95(each3H,s,H灢23 5).(Deyama,1983)
to30);13C灢NMR(Pyridine灢d5,125MHz):毮C48灡1(t, clemaphenolA(9)wasobtainedascolorlessoil,C20
C灢1),68灡9(d,C灢2),84灡2(d,C灢3),40灡2(s,C灢4), H22O6;1H灢NMR(CDCl3,500MHz):毮H3灡13(2H,m,
56灡3(d,C灢5),19灡2(t,C灢6),33灡6(t,C灢7),38灡9(s, H灢1,5),4灡76(2H,d,J=3灡9,H灢2,6),3灡89灢4灡27
C灢8),48灡5(d,C灢9),40灡2(s,C灢10),24灡3(t,C灢11), (4H,dd,H灢4,8),3灡92(6H,s,2暳OMe),5灡69(2H,
122灡8(d,C灢12),145灡2(s,C灢13),42灡6(s,C灢14), br灡s,2暳OH),6灡92(2H,br灡s,H灢2曚,2曞),6灡91(2H,
28灡6(t,C灢15),24灡1(t,C灢16),46灡8(s,C灢17),42灡4 d,H灢5曚,5曞),6灡85 (2H,dd,H灢6曚,6曞);13C灢NMR
(d,C灢18),47灡0(t,C灢19),31灡3(s,C灢20),34灡6(t,C灢 (CDCl3,125MHz):毮C146灡6(s,C灢4曚,4曞),145灡2(s,
21),33灡6(t,C灢22),30灡4(q,C灢23),17灡2(q,C灢24), C灢3曚,3曞),132灡8(s,C灢1曚,1曞),118灡9(d,C灢6曚,6曞),
17灡8(q,C灢25),18灡1(q,C灢26),26灡5(q,C灢27),180灡6 114灡2(d,5曚,5曞),108灡5(d,2曚,2曞),85灡8(d,C灢2,6),
(s,C灢28),33灡6(q,C灢29),24灡1(q,C灢30).(Taniguchi 71灡6(t,C灢4,8),55灡9(q,OMe),54灡1(d,C灢1,5).
etal灡,2002) (Heetal灡,2001)
vomifoliol(6)wasobtainedaswhitecrystals,C13 japonicaacid(10)wasobtainedaswhiteamorphous
H20O3;ESI灢MS m/z:225 [M + H]+;1H灢NMR powder,C18H26O4;1H灢NMR(Pyridine灢d5,500MHz):
(CDCl3,500MHz):毮H5灡86(1H,s,H灢2),1灡25(3H, 毮H7灡46灢7灡34(2H,m,H灢11,14),6灡77,6灡75(each
d,J=6灡2,H灢4曚),1灡85(3H,d,J=1灡0,Me灢C3), 1H,br灡d,J=3灡1,H灢12,13),6灡40,6灡50(each1H,
1灡04(3H,s,Me毬灢C5),1灡09(3H,s,Me毩灢C5),4灡36 d,J=15灡5,H灢10,15),2灡56(2H,q,H灢17),2灡52
(1H,m,H灢3曚);13C灢NMR (CDCl3,100 MHz);毮C (2H,t,J=7灡2,H灢8),2灡50(2H,t,J=7灡2,H灢2),
198灡6(s,C灢1),126灡9(d,C灢2),163灡7(s,C灢3),79灡1 1灡80灢1灡61(4H,m,H灢3,7),1灡36灢1灡24(6H,m,H灢4,
(s,C灢4),41灡3(s,C灢5),49灡8(t,C灢6),135灡8 (d,C灢 5,6),1灡08(3H,t,J=7灡2,H灢18);13C灢NMR(Pyri灢
1曚),129灡1(d,C灢2曚),68灡1(d,C灢3曚),24灡2(q,C灢4曚), dine灢d5,125MHz):毮C176灡0(s,C灢1),34灡8(t,C灢2),
19灡2(q,Me灢C (3)),23灡8 (q,Me毩灢C5),23灡0 (q, 25灡5(t,C灢3),29灡5(t,C灢4),29灡4(t,C灢5),29灡3(t,
Me毬灢C5).(Siddiquietal灡,2003) C灢6),24灡4(t,C灢7),40灡9(t,C灢8),200灡0(s,C灢9),
roseoside(7)wasobtainedascolorlessoil,C19H30 138灡7(C灢10),140灡6 (d,C灢11),132灡8 (d,C灢12),
云 南 植 物 研 究 第 卷
4暋60暋暋暋暋暋暋暋暋暋暋暋 暋暋暋暋暋暋暋 暋 暋 暋 暋 暋 暋暋暋暋暋暋暋暋暋暋暋暋暋暋暋暋 32
132灡5(d,C灢13),140灡5 (d,C灢14),138灡7 (C灢15), 7灡24(4H,m,H灢2曚,3曚,5曚,6曚),7灡13(1H,m,H灢4曚),
200灡2(s,C灢16),34灡0(t,C灢17),8灡2(q,C灢18).(Wu 6灡18(1H,d,J=2灡2,H灢6),6灡95(1H,d,J=2灡2,
etal灡,1998) H灢8),5灡03(1H,d,J=7灡1,H灢1曞),3灡90(1H,dd,J
lutein(11)wasobtainedasredamorphouspowder, =12灡1,2灡2,H灢6曞),3灡70(1H,dd,J=12灡1,5灡5,
C40H56O2;ESI灢MSm/z:569[M灢H]+;1H灢NMR(Pyr灢 H灢6曞),3灡30(2H,overlapped,H灢3),3灡52灢3灡35(3H,
idine灢d5,500 MHz):毮H 6灡92灢6灡84 (2H,m,H灢11, m,H灢3曚,4曚,5曚),2灡97(2H,t,H灢2);13C灢NMR(CD3
11曚),6灡65(2H,d,J=15灡2,H灢15,15曚),6灡51灢6灡32 OD,125 MHz):毮C31灡7 (t,C灢2),46灡6 (t,C灢3),
(6H,m,H灢8,8曚,10,10曚,12,12曚),5灡96(1H,s,H灢 206灡4(s,C灢4),162灡5(s,C灢5),98灡5(d,C灢6),167灡7
4曚),5灡64(1H,ddd灢like,J=15灡2,10灡3,9灡8,H灢7曚), (s,C灢7),95灡7(d,C灢8),166灡1(s,C灢9),107灡0(s,C灢
4灡62(1H,br灡s,H灢3曚),4灡36灢4灡30 (1H,m,H灢3), 10),143灡2(s,C灢1曚),129灡6(d,C灢2曚,6曚),129灡5(d,
2灡65(1H,dd,J=17灡2,5灡4,H灢4a),2灡53(1H,d,J C灢3曚,5曚),126灡9(d,C灢5曚),102灡3(d,C灢1曞),74灡9(d,
=10灡3,H灢6曚),2灡43(1H,dd,J=17灡2,9灡8,H灢4b), C灢2曚),78灡6(d,C灢3曚),71灡3(d,C灢4曚),78灡6(d,C灢5曚),
2灡06(3H,s,H灢18曚),2灡03(6H,d,J=4灡9,H灢19曚, 62灡6(t,C灢6曞).(Hegdeetal灡,2003)
20曚),1灡99(3H,s,H灢20),1灡84(3H,s,H灢19),1灡71 naringenin灢7灢O灢毬灢D灢glucopyranoside(14)wasob灢
(3H,s,H灢18),1灡19(3H,s,H灢16),1灡18(3H,s,H灢 tainedasyellowamorphouspowder,C21H22O10;1H灢
17),1灡13(3H,s,H灢17曚),0灡95(3H,s,H灢16曚);13C灢 NMR(Pyridine灢d5,500MHz):毮H7灡51(2H,d,J=
NMR(Pyridine灢d5,125MHz):毮C37灡6(s,C灢1),49灡9 8灡6,H灢2曚,6曚),7灡21(2H,d,J=8灡6,H灢3曚,5曚),6灡61
(t,C灢2),64灡3(d,C灢3),44灡1(t,C灢4),126灡1(s,C灢 (1H,d,J=2灡2,H灢8),6灡58(1H,d,J=2灡2,H灢6),
5),137灡3(s,C灢6),138灡5(d,C灢7),138灡3(d,C灢8), 5灡75(1H,d,J=7灡8,H灢1曚),5灡42(1H,dd,J=
136灡2(s,C灢9),131灡3(d,C灢10),124灡2(d,C灢11), 12灡6,2灡7,H灢2),4灡50灢4灡13(6H,m,H灢2曚to6曚),3灡29
137灡3(d,C灢12),136灡5(s,C灢13),132灡5(d,C灢14), (1H,dd,J=12灡6,16灡9,H灢3毬),2灡89(1H,dd,J=
130灡4(d,C灢15),29灡3(q,C灢16),30灡3(q,C灢17),22灡3 16灡9,3灡0,H灢3毩);13C灢NMR(Pyridine灢d5,125MHz):
(q,C灢18),13灡2(q,C灢19),13灡26(q,C灢20),34灡8(s, 毮C80灡0(d,C灢2),43灡5(t,C灢3),197灡5(s,C灢4),
C灢1曚),46灡2(t,C灢2曚),65灡3(d,C灢3曚),126灡0(s,C灢4曚), 166灡9(s,C灢5),97灡9(d,C灢6),164灡8(s,C灢7),96灡7
133灡7(s,C灢5曚),55灡7 (d,C灢6曚),131灡3 (d,C灢7曚), (d,C灢8),163灡9(s,C灢9),104灡6(s,C灢10),129灡8(s,
128灡0(d,C灢8曚),133灡7(s,C灢9曚),127灡8(d,C灢10曚), C灢1曚),129灡2(d,C灢2曚,6曚),116灡7(d,C灢3曚,5曚),159灡9
126灡9(d,C灢11曚),138灡4(d,C灢12曚),138灡5(s,C灢13曚), (s,C灢4曚),101灡8(d,C灢1曞),75灡0(d,C灢2曞),78灡6(d,
131灡9(d,C灢14曚),139灡1(d,C灢15曚),24灡6(q,C灢16曚), C灢3曞),71灡2(d,C灢4曞),79灡3(d,C灢5曞),62灡4(t,C灢6曞).
31灡0(q,C灢17曚),23灡4(q,C灢18曚),13灡6(q,C灢19曚), (Luetal灡,2007)
13灡3(q,C灢20曚).(Baranyaietal灡,1981) vitexin (8灢C灢毬灢D灢glucopyranosylapigenin)(15)
trilobatin(12)wasobtainedasyellowpowder,C22 wasobtainedasyellowamorphouspowder,C21H20O10;
H24O10;1H灢NMR(CD3OD,500MHz):毮H7灡06(2H, 1H灢NMR(DMSO灢d6,500MHz):毮H8灡02(2H,d,J=
d,J=8灡8,H灢2曚,6曚),6灡69(2H,d,J=8灡8,H灢3曚, 8灡8,H灢2曚,6曚),6灡89(2H,d,J=8灡8,H灢3曚,5曚),6灡78
5曚),6灡19(1H,d,J=2灡2,H灢6),5灡97(1H,d,J= (1H,s,H灢3),6灡27(1H,s,H灢6),5灡06(1H,d,J=
2灡2,H灢8),5灡05(1H,d,J=7灡1,H灢1曞),3灡92(1H, 5灡3,H灢1曞),5灡03(1H,d,J=4灡1,H灢1曞),4灡67(2H,
dd,J=12灡0,1灡6,H灢2曞),3灡73(1H,dd,J=12灡1, m,H灢2曞,5曞),3灡83 (1H,t,J=9灡4,H灢3曞),3灡76
5灡5,H灢5曞),3灡52灢3灡38(2H,m,H灢3曞,4曞),3灡35(3H, (1H,m,H灢4曞),3灡25(2H,m,H灢6曞);13C灢NMR(DM灢
s,OMe),2灡87 (2H,t,J=7灡7,H灢6曞);13C灢NMR SO灢d6,125MHz):毮C164灡1(s,C灢2),102灡5(d,C灢3),
(CD3OD,125MHz):毮C30灡8(t,C灢2),47灡0(t,C灢3), 182灡2(s,C灢4),160灡5(s,C灢5),98灡2(d,C灢6),162灡7
206灡6(s,C灢4),165灡9(s,C灢5),98灡5(d,C灢6),167灡5 (s,C灢7),104灡1(s,C灢8),156灡1(s,C灢9),104灡7(s,C灢
(s,C灢7),95灡5(d,C灢8),162灡3(s,C灢9),106灡8(s,C灢 10),121灡7(s,C灢1曚),129灡1(d,C灢2曚,6曚),115灡9(d,
10),134灡0(s,C灢1曚),130灡5(d,C灢2曚,6曚),116灡2(d, C灢3曚,5曚),161灡2(C灢4曚),73灡5(d,C灢1曞),70灡6(d,C灢
C灢3曚,5曚),156灡3(s,C灢4曚),102灡0(d,C灢1曞),74灡7(d, 2曞),78灡7(d,C灢3曞),70灡9(d,C灢4曞),81灡9(d,C灢5曞),
C灢2曞),78灡4(d,C灢3曞),71灡1(d,C灢4曞),78灡5(d,C灢5曞), 61灡4(t,C灢6曞).(Huetal灡,2006)
62灡4(t,C灢6曞).(Tanakaetal灡,1982) 7灢O灢毬灢D灢glucopyranosylchrysin(16)wasobtained
3灢phenyl灢1灢(2曚,6曚灢dihydroxy灢phenyl灢4曚灢O灢毬灢D灢glu灢 asyellowamorphouspowder,C21H20O9;1H灢NMR(Pyr灢
copyranosyl)灢1灢propanone(13)wasobtainedasyellow idine灢d5,500MHz):毮H7灡92(1H,d,J=1灡3,H灢2曚),
powder,C21H24O9;1H灢NMR(CD3OD,500MHz):毮H 7灡90(1H,d,J=1灡9,H灢6曚),7灡50(1H,d,J=2灡4,
期
5 暋暋暋暋暋暋SONGWei灢Wuetal灡:ANewLignanfromElaeagnuslanceolata(Elaeagnaceae)暋暋暋暋暋暋46暋1
H灢6),7灡45(3H,m,H灢3曚,4曚,5曚),7灡05(1H,d,J= (2H,d,J=8灡9,H灢3曚,5曚),6灡72(2H,d,J=8灡5,H灢
2灡4,H灢3),6灡96(1H,s,H灢8),5灡43(1H,d,J=7灡5, 6熓,8熓),6灡20(1H,d,J=1灡9,H灢8),6灡05(1H,d,J
H灢1曞),4灡46(1H,m,H灢2曞),4灡42灢4灡36(4H,m,H灢4曚, =2灡1,H灢6),6灡02(1H,d,J=15灡9,H灢2熓),5灡20
5曚,6曚),4灡06(1H,m,H灢3曞);13C灢NMR(Pyridine灢d5, (1H,dd,J=1灡9,5灡6,H灢1曞);13C灢NMR(CD3OD,125
125MHz):毮C165灡0(s,C灢2),109灡9(d,C灢3),178灡5 MHz):毮C159灡3(s,C灢2),135灡4(s,C灢3),179灡4(s,C灢
(s,C灢4),160灡6(s,C灢5),105灡8(d,C灢6),161灡8(s,C灢 4),162灡9(s,C灢5),100灡0(d,C灢6),165灡9(s,C灢7),
7),99灡8(d,C灢8),160灡0(s,C灢9),109灡3(s,C灢10), 95灡0(d,C灢8),158灡3(s,C灢9),105灡6(s,C灢10),122灡7
132灡0(s,C灢1曚),132灡1(d,C灢4曚),129灡6(d,C灢3曚,5曚), (s,C灢1曚),132灡3(d,C灢2曚),116灡1(d,C灢3曚),161灡6(s,
126灡8(d,C灢2曚,6曚),106灡9(d,C灢1曞),75灡7(d,C灢2曞), C灢4曚),116灡1(d,C灢5曚),132灡3(d,C灢6曚),104灡2(d,C灢
77灡9(d,C灢3曞),71灡4(d,C灢4曞),79灡7(d,C灢5曞),62灡7 1曞),78灡1(d,C灢2曞),75灡8(d,C灢3曞),71灡8(d,C灢4曞),
(t,C灢6曞).(Eletal灡,2004) 75灡8(d,C灢5曞),64灡5(t,C灢6曞),169灡0(s,C灢1熓),114灡8
isorhamnetin3灢O灢毩灢L灢rhamnopyranosyl灢7灢O灢毬灢D灢 (d,C灢2熓),146灡7(d,C灢3熓),127灡1(s,C灢4熓),131灡3
glucopyranoside(17)wasobtainedasyellowpowder,C28 (d,C灢5熓),116灡9(d,C灢6熓),161灡2(s,C灢7熓),116灡9
H32O16;1H灢NMR(CD3OD,500MHz):毮H7灡95(1H, (d,C灢8熓),131灡3(d,C灢9熓).(Tsukamotoetal灡,2004)
d,J=1灡7,H灢2曚),7灡63(1H,dd,J=8灡8,1灡7,H灢
Acknowledgement
6曚),6灡92(1H,d,J=8灡8,H灢5曚),6灡42(1H,d,J= :Theauthorsaregratefultothemem灢
2灡2,H灢8),6灡22(1H,d,J=2灡2,H灢6),5灡24(1H,d, bersoftheanalyticalgroupoftheStateKeyLaboratoryof
J=7灡1,H灢1曞),4灡53(1H,s,H灢1熓),3灡95(3H,s, PhytochemistryandPlantResourcesinWestChina,Kun灢
OMe),3灡82(1H,d,J=11灡0,H灢2熓),3灡61(1H,s, mingInstituteofBotany,ChineseAcademyofSciences
H灢2曞),3灡50灢3灡24(6H,m,H灢3曞,3熓,4曞,4熓,5曞,5熓), forallofthespectralmeasurements.
1灡10(3H,d,J=6灡6,H灢6曞);13C灢NMR(CD3OD,125
Reference
MHz):毮C159灡1(s,C灢2),135灡6(s,C灢3),179灡5(s,C灢 :
4),163灡2(s,C灢5),100灡1(d,C灢6),166灡2(s,C灢7), AnderssonR,LundgrenLN,1988.Theconstituentsofconifernee灢
95灡1(d,C灢8),158灡7(s,C灢9),105灡9(s,C灢10),123灡2 dles.13.Monoarylandcyclohexenoneglycosidesfromneedles
(s,C灢1曚),114灡7(d,C灢2曚),148灡5(s,C灢3曚),151灡0(s, ofPinussylvestris[J].Phytochemistry,27(2):559—562
C灢4曚),116灡3(d,C灢5曚),124灡2(d,C灢6曚),104灡5(d,C灢 BaranyaiM,MolnarP,SzabolcsJetal灡,1981.Determination
1曞),74灡0(d,C灢2曞),76灡1(d,C灢3曞),69灡9(d,C灢4曞), ofthegeometricconfigurationofthepolyenechainofmono灢
77灡5(C灢5曞),68灡7(t,C灢6曞),102灡7(d,C灢1熓),72灡2(d, cis灢C40carotenoids.栻.AC灢13灢NMRstudyofmono灢cis
lutenisand mono灢ciscapsanthins[J].Tetrahedron,37
C灢2熓),78灡3(d,C灢3熓),72灡4(d,C灢4熓),71灡8(d,C灢
(1):203—207
5熓),18灡0(q,C灢6熓),57灡0(q,OMe).(Wolbis,1989)
CaoSG,TanakaT,MizunoMetal灡,2001.Flavonolglycosides
kaempferol灢3灢O灢毬灢D灢glucopyranoside(18)wasob灢 fromElaeagnuslanceollata(Elaeagnaceae)[J].Natural
tainedasyellowamorphouspowder,C21H20O11;1H灢 ProductLetters,15(4):211—216
NMR(Pyridine灢d5,500MHz):毮H8灡43(2H,d,J= ChenZX(陈智新),MaXY(马晓英),JiangGH(蒋高华)etal灡,
9灡0,H灢2曚,6曚),7灡19(1H,d,J=7灡2,H灢8),6灡70 2009.StudyonthechemicalconstituentsfromCyrtomium
云南化
(2H,dd,J=7灡2,2灡0,H灢3曚,5曚),6灡32(1H,d,J= caryotideum [J].YunnanChemicalTechnology(
7灡2,H灢6),4灡40灢4灡03 (6H,m,H灢sugar);13C灢NMR 工),36(5):9—12
(Pyridine灢d5,125MHz):毮C157灡7(s,C灢2),135灡2(s, DeyamaT,1983.TheconstituentsofEucommiaulmoidesOliv.
C灢3),178灡9(s,C灢4),157灡5(s,C灢5),99灡9(s,d,C灢 1.Isolationof(+)灢medioresinoldi灢O灢毬灢D灢glucopyrano灢
6),166灡0(s,C灢7),94灡7(d,C灢8),162灡9(s,C灢9), side[J].Chemical&PharmaceuticalBulletin,31(9):
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云南植物研究 创刊于 年 是由中国科学院主管 中国科学院昆明植物研究所承办的全国性自然科学学术
《 》 1979 , 、
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(1997) (1997) , SCI
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外 美国化学文摘 美国生物学文摘 等从 年起就连续摘报 生物科学的当代进展 科学引
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、 、 5 。
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