全 文 ：披针叶胡颓子中的一个新木脂素*
宋卫武1,2,李暋波1
**,刘吉开1
(1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 昆明暋650204;
2中国科学院研究生院,北京暋100049)
摘要:从披针叶胡颓子 (Elaeagnuslanceolata)的干燥枝叶中分离得到19个化合物,其中isoamericanol
B(1)为一新化合物,经波谱学方法鉴定其结构为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:Q946暋暋暋暋 暋暋文献标识码:A暋暋暋暋 暋暋暋文章编号:0253灢2700(2010)05灢455灢08
ANewLignanfromElaeagnuslanceolata(Elaeagnaceae)
SONG Wei灢Wu1,2,LIBo1** ,LIUJi灢Kai1
(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
longstothegenusElaeagnus (Elaeagnaceae),
whichcomprisesabout80 speciesand wide灢
spreadinsubtropicalandtemperateareasofEast
andSoutheastAsia,amongthem55speciesare
foundinChina(EditorialBoardofFloraofChi灢
naofChinese AcademyofSciences,1979).
Leaves,fruits,androotsofE灡lanceolatahave
beenusedtotreatcough,asthma,dysenteryand
congestion(EditorialBoardofNationalHerbal
Compendium,1975).Fourflavonolglycosides
andaphenylpropanoidwerereportedfromthe
leavesofthisplantbefore(Caoetal灡,2001).
Aspartofourongoingprogramondiscovering
naturalskincareproductsfromTraditionalChi灢
neseMedicine,athoroughchemicalworkwas
carriedoutonthisplant.Anewlignan,isoame灢
ricanolB (1),togetherwith18knowncom灢
poundswereisolatedfromthedryleavesand
twigs of E灡lanceolata. These known com灢
poundswereidentifiedtobe6灢hydroxy灢3,4灢di灢
hydro灢1灢oxo灢毬灢carboline(2),2毩灢hydroxy灢ursolic
acid (3),2毩,23灢dihydroxy灢ursolicacid (4),
maslinicacid (5),vomifoliol (6),roseoside
云 南 植 物 研 究暋2010,32(5):455~462
ActaBotanicaYunnanica暋暋暋暋暋暋暋暋暋暋暋暋暋暋暋暋暋暋DOI:10灡3724/SP灡J灡1143灡2010灡10112
*
**
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 (1983-)男,在读硕士研究生,主要从事天然药物化学研究。
(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MS at m/z 351灡1205 [M + Na]+
(calcd.forC19H20O5Na+ ,351灡1208),indica灢
tingtendegreesofunsaturation.TheIRspec灢
trumshowedabsorptionsat3432,1580,1505
cm灢1,suggestingthepresenceofhydroxylgroup,
doublebondandaromaticmoiety. Fig灡1暋Structuresofcompounds2-11
Fig灡2暋Structuresofcompounds12-19
654暋暋暋暋暋暋暋暋暋暋暋暋 暋暋暋暋暋暋暋云暋南暋植暋物暋研暋究暋暋暋暋暋暋暋暋暋暋暋暋暋暋暋暋第32卷
暋暋Inthe13C灢NMRspectrumof1(Table1),
19carbonsignalswereobserved,includingone
methyl(毮C13灡6),onemethoxy(毮C56灡4),one
oxygen灢bearingmethylene(毮C60灡0),twooxy灢
gen灢bearingmethines(毮C74灡3,78灡5),aswel
aseightaromaticmethinesandsixquaternary
aromaticcarbons,whichbelongtotwophenyls
andonedisubstituteddoublebond (Table1).
The1H灢NMRsignalsat毮H4灡33(dd,J=6灡3,
1灡6),5灡72(dt,J=11灡9,6灡3),and6灡42(d,
J=11灡7),13C NMRsignalsat毮C 60灡0 (t),
131灡4(d),and130灡8(d)indicatedthepresence
ofone(Z)alylalcoholunit,whichwasalso
confirmedbyCOSYspectrum.Inthe HMBC
spectrum,correlationsbetweenH灢9andC灢8,C灢
7,H灢8andC灢4曚,H灢7andC灢3曚,C灢1,C灢2,C灢6
confirmedthestructurefragmentofbenzodiox灢
ane.Further 2D NMR spectra data analysis
(HSQC,COSY,andHMBC)suggestedthatcom灢
pound1possessaneolignanskeleton,whichwas
composedoftwophenylpropanoidsunitsconnected
bya1,4灢dixoanering(Fig灡3).The1Hand13C
NMRspectradataof1wereverysimilartothoseof
isoamericanolA (Waibeletal灡,2003),exceptfor
thepresenceofoneadditionalmethoxy,onecis
doublebond,andonemethylin1,insteadofone
trans double bond and one hydroxymethylin
isoamericanolA(Fig灡4).
Therelativestereochemistryof1wasdeter灢
minedbythecorrelationbetweenH灢9andH灢7,
observedintheROESYspectrumof1,which
establishedthetrans灢relationshipbetweenH灢7
andH灢8.Thus,thestructureof1waselucida灢
tedasrel灢(7曚Z)灢(7毬,8毩)灢3灢methoxy灢4,9曚灢di灢
hydroxy灢3曚,7灢epoxy灢8,4曚灢oxyneolign灢7曚灢ene.
Experimental
Generalexperimentalprocedures暋 Opticalrotation
wasmeasuredonaJASCOP灢1020digitalpolarimeter.IR
spectrawereobtainedfromBrukerTensor27FT灢IRspec灢
trometerwithKBrpelets.UVspectraweredetermined
ona Shimadzu UV2401PC spectrometer.ESIMSand
HRESIMSspectrawererecordedon AutoSpecPremier
P776andAPIQSTARPulsarinstrument.NMRspectra
wererecordedonBrukerAM灢400andDRX灢500spectrom灢
eterswithTMSasinternalstandard.Silicagel(200-300
mesh),SilicagelF254 (Qingdao MarineChemicalCo.,
Ltd),RP灢18silicagel(40-63毺m,Merck,Germany),
MCIgelCHP灢20P (75-150毺m,MitsubishiChemical
Corporation,Tokyo)andSephadexLH灢20 (Pharmacia)
wereusedforcolumnchromatography.Fractionswere
monitoredbyTLCandspotswerevisualizedbyheating
silicagelplatesimmersedwith10% H2SO4inethanol.
Table1暋1Hand13CNMRdateof1andisoamericanolAinCD3OD(毮inppm,JinHz)
NO.
1
毮Ca) 毮Hb)
IsoamericanolA
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.
7545期暋暋暋暋暋暋SONG Wei灢Wuetal灡:ANewLignanfrom Elaeagnuslanceolata(Elaeagnaceae)暋暋暋暋暋暋暋
暋暋Plantmaterial暋TheleavesandtwigsofElaeagnus
lanceolata werecolectedin Yimencountyof Yunnan
Province,China,inSeptember,2008,andidentifiedby
Prof.ChenYu, KunmingInstituteofBotany,Chinese
AcademyofSciences.Avoucherspecimenwasdeposited
intheStateKeyLaboratoryofPhytochemistryandPlant
ResourcesinWestChina,KunmingInstituteofBotany,
ChineseAcademyofSciences.
Extractionandisolation暋Theair灢driedleavesand
twigs(7kg)ofElaeagnuslanceolatawereextractedwith
methanolatroomtemperature(4暳40L).Theextracts
werecombinedandconcentrated,andtheresiduewasdis灢
solvedinMeOH/H2O(9暶1),andthensuccessivelypar灢
titionedwithpetroleumether,chloroformandn灢BuOH.
Thepetroleumetherextract(149g)wassubjectedtocol灢
umnchromatographyoversilicagel(CHCl3/MeOH100
暶0曻90暶10)toafford3fractions.Columnchromatog灢
raphyofFraction2oversilicagel(CHCl3/acetone30暶1
曻7暶3)afforded11(30 mg).Thechloroformextract
(198g)wassubjectedtocolumnchromatographyover
silicagel(CHCl3/MeOH100暶0曻70暶30)toafford6
fractions A灢F.Fraction B was repeatedly chromato灢
graphedoversilicagel(CHCl3/acetone30暶1曻7暶3or
petroleumether/Acetone9暶1曻7暶3orpetroleumether/
EtOAc9暶1曻7暶3),MCIgel(MeOH/H2O5暶5曻10暶
0),SephadexLH灢20(MeOH)andRP灢18(MeOH/H2O
30暶70曻100暶0)toafford8(20mg),10(5mg)and9
(20mg).Inthesameway,2(10mg),3(60mg),4(10
mg),5(65mg)and6(18mg)wereisolatedfromFrac灢
tionC;1(12mg),13(10mg),14(20mg),16(50
mg),18(45mg)and19wereobtainedfromFractionD;
12(369)wasfrom FractionE;7(10mg),17(6mg)
and15(50mg)werefromthen灢BuOHextract(296g).
isoamericanolB(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epoxy灢8,4曚灢oxyneolign灢7曚灢ene)was
obtainedascolorlessamorphoussolid,C19H20O5;UV
毸MeOHmax (log毰):286灡4 (3灡76),259灡4 (4灡05),216
(4灡44),204 (4灡59)nm;[毩]24D = +98灡1 (c =0灡4,
MeOH);IR毻KBrmax (cm灢1):3432,2925,2852,1612,
1580,1505,1463,1429,1380,1267;1Hand13C灢NMR:
seeTable1;ESI灢MS(positive)m/z:351[M+Na]+ ,
HR灢ESI灢MS (positive) m/z:351灡1205 [M + Na]+
(calcd.forC19H20O5Na+ ,351灡1208).
6灢hydroxy灢3,4灢dihydro灢1灢oxo灢毬灢carboline (2) was
obtainedasyelowpowder,C11H10N2O2;1H灢NMR(CD3
OD,500MHz):毮H7灡27(1H,d,J=8灡8,H灢8),6灡90
(1H,d,J=2灡3,H灢5),6灡84(1H,dd,J=2灡3,8灡8,
H灢7),3灡61(2H,t,J=7灡0,H灢3),2灡93(2H,t,J=
7灡0,H灢4);13C灢NMR (CD3OD,100 MHz):毮C 165灡0
(s,C灢1),42灡8(t,C灢3),21灡5(t,C灢4),104灡2(d,C灢
5),152灡2(s,C灢6),116灡8(d,C灢7),114灡0(d,C灢8),
134灡2(s,C灢9a),127灡9 (s,C灢8a),127灡0 (s,C灢4b),
120灡2(s,C灢4a).(Salmounetal灡,2002)
2毩灢hydroxy灢ursolicacid (3)wasobtainedaswhite
powder,C30H48O4;ESI灢MSm/z:495[M+Na]+ ;1H灢
NMR(Pyridine灢d5,500MHz):毮H5灡46(1H,br灡s,H灢
12),4灡10 (1H,ddd,J=9灡2,9灡2,4灡1,H灢2),3灡40
(1H,d,J =9灡2,H灢3),1灡27 (3H,s,H灢23),1灡20
(3H,s,H灢27),1灡07(3H,s,H灢24),1灡04(3H,s,H灢
25),0灡98(3H,d,J=5灡9,H灢29),0灡97(3H,s,H灢
26),0灡95(3H,d,J=5灡9,H灢30);13C灢NMR (Pyri灢
dine灢d5,100MHz):毮C48灡0(t,C灢1),68灡6(d,C灢2),
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,
C灢6),33灡5 (t,C灢7),40灡0 (s,C灢8),48灡1 (d,C灢9),
38灡4(s,C灢10),23灡7 (t,C灢11),125灡5 (d,C灢12),
139灡3(s,C灢13),42灡5(s,C灢14),28灡6(t,C灢15),24灡9
(t,C灢16),48灡0(s,C灢17),53灡5(d,C灢18),39灡4(d,C灢
19),39灡5(d,C灢20),31灡1(t,C灢21),37灡4(t,C灢22),
29灡4(q,C灢23),17灡5(q,C灢24),17灡0(q,C灢25),17灡7
(q,C灢26),23灡9(q,C灢27),179灡9(s,C灢28),17灡5(q,
854暋暋暋暋暋暋暋暋暋暋暋暋 暋暋暋暋暋暋暋云暋南暋植暋物暋研暋究暋暋暋暋暋暋暋暋暋暋暋暋暋暋暋暋第32卷
C灢29),21灡4(q,C灢30).(Kimetal灡,2005)
2毩,23灢dihydroxy灢ursolicacid (4)wasobtainedas
whiteamorphouspowder,C30H48O5;ESI灢MSm/z:511
[M+Na]+ ;1H灢NMR (Pyridine灢d5,500 MHz):毮H
5灡45(1H,t,J=4灡0,H灢12),3灡91(1H,d,J=11灡0,
H灢23毩),3灡74(1H,d,J=11灡0,H灢23毬),2灡59 (1H,
d,J=11灡6,H灢18),1灡12(3H,s,H灢27),1灡04(3H,
s,H灢25),0灡98(3H,s,H灢26),0灡94(3H,d,J=6灡4,
H灢30),0灡91(3H,d,J=6灡4,H灢29),0灡85(3H,s,H灢
24);13C灢NMR(Pyridine灢d5,125MHz):毮C43灡8(t,C灢
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5),18灡5(t,C灢6),33灡4(t,C灢7),39灡7(s,C灢8),
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12),139灡6(s,C灢13),42灡2(s,C灢14),28灡9(t,
C灢15),25灡1(t,C灢16),48灡3 (s,C灢17),53灡8 (d,C灢
18),39灡7(d,C灢19),40灡3(d,C灢20),31灡3(t,C灢21),
37灡7(t,C灢22),71灡5(t,C灢23),18灡0(q,C灢24),17灡8
(q,C灢25),17灡8(q,C灢26),24灡1(q,C灢27),180灡2(s,
C灢28),17灡4(q,C灢29),21灡7(q,C灢30).(Fangetal灡,
2008)
maslinicacid(5)wasobtainedaswhiteamorphous
powder,C30H48O4;1H灢NMR(Pyridine灢d5,500MHz):
毮H5灡48(1H,br灡s,H灢12),4灡12(1H,ddd,J=11灡2,
9灡4,4灡1,H灢2),3灡41(1H,d,J=9灡4,H灢3),1灡29,
1灡27,1灡09,1灡03,1灡01,0灡99,0灡95(each3H,s,H灢23
to30);13C灢NMR(Pyridine灢d5,125MHz):毮C48灡1(t,
C灢1),68灡9 (d,C灢2),84灡2 (d,C灢3),40灡2 (s,C灢4),
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,
C灢8),48灡5(d,C灢9),40灡2(s,C灢10),24灡3(t,C灢11),
122灡8(d,C灢12),145灡2 (s,C灢13),42灡6 (s,C灢14),
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,C灢18),47灡0(t,C灢19),31灡3(s,C灢20),34灡6(t,C灢
21),33灡6(t,C灢22),30灡4(q,C灢23),17灡2(q,C灢24),
17灡8(q,C灢25),18灡1(q,C灢26),26灡5(q,C灢27),180灡6
(s,C灢28),33灡6(q,C灢29),24灡1(q,C灢30).(Taniguchi
etal灡,2002)
vomifoliol(6)wasobtainedaswhitecrystals,C13
H20O3;ESI灢MS m/z:225 [M + H]+ ;1H灢NMR
(CDCl3,500MHz):毮H5灡86(1H,s,H灢2),1灡25(3H,
d,J=6灡2,H灢4曚),1灡85 (3H,d,J=1灡0,Me灢C3),
1灡04(3H,s,Me毬灢C5),1灡09 (3H,s,Me毩灢C5),4灡36
(1H,m,H灢3曚);13C灢NMR (CDCl3,100 MHz);毮C
198灡6(s,C灢1),126灡9(d,C灢2),163灡7(s,C灢3),79灡1
(s,C灢4),41灡3(s,C灢5),49灡8(t,C灢6),135灡8 (d,C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),
19灡2 (q,Me灢C (3)),23灡8 (q,Me毩灢C5),23灡0 (q,
Me毬灢C5).(Siddiquietal灡,2003)
roseoside(7)wasobtainedascolorlessoil,C19H30
O8;ESI灢MS m/z:385 [M灢H]+ ;1H灢NMR (CD3OD,
500MHz):毮H 1灡03 (3H,s,Me毩灢C5),1灡04 (3H,s,
Me毬灢C5),1灡29(3H,d,J=6灡3,H灢4曚),1灡92(3H,d,
J=1灡2,Me灢C3),2灡14(1H,d,J=16灡8,H灢6毬),2灡52
(1H,d,J=16灡8,H灢6毩),3灡14灢3灡86 (5H,m,H灢2曞,
6曞),4灡34(1H,d,J=7灡8,H灢1曞),4灡42(1H,m,H灢
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
(1H,m,H灢2);13C灢NMR (CD3OD,125 MHz):毮C
201灡2(C灢1),127灡1 (d,C灢2),167灡3 (C灢3),80灡0 (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
(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
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
(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,
Me毬灢C5),19灡5(q,Me灢C3).(AnderssonandLundgren,
1988)
syringaresinol(8)wasobtainedaswhiteamorphous
powder,C22H26O8;ESI灢MSm/z:419[M+H]+ ;1H灢
NMR(CDCl3,500MHz):毮H 6灡57(4H,s,H灢2曚,6曚,
2曞,6曞),4灡72 (2H,d,J =3灡8,H灢2,6),4灡28灢3灡89
(4H,m,H灢4,8),3灡88(12H,s,4暳OMe),3灡11灢3灡05
(2H,m,H灢1,5);13C灢NMR (CDCl3,125 MHz):毮C
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
(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),
71灡7(t,C灢4,8),56灡3 (q,2暳OMe),54灡3 (d,C灢1,
5).(Deyama,1983)
clemaphenolA(9)wasobtainedascolorlessoil,C20
H22O6;1H灢NMR(CDCl3,500MHz):毮H3灡13(2H,m,
H灢1,5),4灡76 (2H,d,J=3灡9,H灢2,6),3灡89灢4灡27
(4H,dd,H灢4,8),3灡92(6H,s,2暳OMe),5灡69(2H,
br灡s,2暳OH),6灡92(2H,br灡s,H灢2曚,2曞),6灡91(2H,
d,H灢5曚,5曞),6灡85 (2H,dd,H灢6曚,6曞);13C灢NMR
(CDCl3,125MHz):毮C146灡6(s,C灢4曚,4曞),145灡2(s,
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),
114灡2(d,5曚,5曞),108灡5(d,2曚,2曞),85灡8(d,C灢2,6),
71灡6(t,C灢4,8),55灡9(q,OMe),54灡1(d,C灢1,5).
(Heetal灡,2001)
japonicaacid(10)wasobtainedaswhiteamorphous
powder,C18H26O4;1H灢NMR(Pyridine灢d5,500MHz):
毮H7灡46灢7灡34 (2H,m,H灢11,14),6灡77,6灡75 (each
1H,br灡d,J=3灡1,H灢12,13),6灡40,6灡50(each1H,
d,J=15灡5,H灢10,15),2灡56 (2H,q,H灢17),2灡52
(2H,t,J=7灡2,H灢8),2灡50(2H,t,J=7灡2,H灢2),
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,
5,6),1灡08(3H,t,J=7灡2,H灢18);13C灢NMR (Pyri灢
dine灢d5,125MHz):毮C176灡0(s,C灢1),34灡8(t,C灢2),
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,
C灢6),24灡4 (t,C灢7),40灡9 (t,C灢8),200灡0 (s,C灢9),
138灡7(C灢10),140灡6 (d,C灢11),132灡8 (d,C灢12),
9545期暋暋暋暋暋暋SONG Wei灢Wuetal灡:ANewLignanfrom Elaeagnuslanceolata(Elaeagnaceae)暋暋暋暋暋暋暋
132灡5(d,C灢13),140灡5 (d,C灢14),138灡7 (C灢15),
200灡2(s,C灢16),34灡0(t,C灢17),8灡2(q,C灢18).(Wu
etal灡,1998)
lutein(11)wasobtainedasredamorphouspowder,
C40H56O2;ESI灢MSm/z:569[M灢H]+ ;1H灢NMR(Pyr灢
idine灢d5,500 MHz):毮H 6灡92灢6灡84 (2H,m,H灢11,
11曚),6灡65(2H,d,J=15灡2,H灢15,15曚),6灡51灢6灡32
(6H,m,H灢8,8曚,10,10曚,12,12曚),5灡96(1H,s,H灢
4曚),5灡64(1H,ddd灢like,J=15灡2,10灡3,9灡8,H灢7曚),
4灡62 (1H,br灡s,H灢3曚),4灡36灢4灡30 (1H,m,H灢3),
2灡65(1H,dd,J=17灡2,5灡4,H灢4a),2灡53(1H,d,J
=10灡3,H灢6曚),2灡43(1H,dd,J=17灡2,9灡8,H灢4b),
2灡06(3H,s,H灢18曚),2灡03 (6H,d,J=4灡9,H灢19曚,
20曚),1灡99(3H,s,H灢20),1灡84(3H,s,H灢19),1灡71
(3H,s,H灢18),1灡19(3H,s,H灢16),1灡18(3H,s,H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d5,125MHz):毮C37灡6(s,C灢1),49灡9
(t,C灢2),64灡3(d,C灢3),44灡1(t,C灢4),126灡1(s,C灢
5),137灡3(s,C灢6),138灡5(d,C灢7),138灡3(d,C灢8),
136灡2(s,C灢9),131灡3 (d,C灢10),124灡2 (d,C灢11),
137灡3(d,C灢12),136灡5 (s,C灢13),132灡5 (d,C灢14),
130灡4(d,C灢15),29灡3(q,C灢16),30灡3(q,C灢17),22灡3
(q,C灢18),13灡2(q,C灢19),13灡26(q,C灢20),34灡8(s,
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),
133灡7 (s,C灢5曚),55灡7 (d,C灢6曚),131灡3 (d,C灢7曚),
128灡0(d,C灢8曚),133灡7 (s,C灢9曚),127灡8 (d,C灢10曚),
126灡9(d,C灢11曚),138灡4(d,C灢12曚),138灡5(s,C灢13曚),
131灡9(d,C灢14曚),139灡1(d,C灢15曚),24灡6(q,C灢16曚),
31灡0(q,C灢17曚),23灡4 (q,C灢18曚),13灡6 (q,C灢19曚),
13灡3(q,C灢20曚).(Baranyaietal灡,1981)
trilobatin(12)wasobtainedasyelowpowder,C22
H24O10;1H灢NMR (CD3OD,500MHz):毮H7灡06(2H,
d,J=8灡8,H灢2曚,6曚),6灡69(2H,d,J =8灡8,H灢3曚,
5曚),6灡19(1H,d,J=2灡2,H灢6),5灡97(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,
dd,J=12灡0,1灡6,H灢2曞),3灡73 (1H,dd,J=12灡1,
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,
s,OMe),2灡87 (2H,t,J =7灡7,H灢6曞);13C灢NMR
(CD3OD,125MHz):毮C30灡8(t,C灢2),47灡0(t,C灢3),
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),95灡5(d,C灢8),162灡3(s,C灢9),106灡8(s,C灢
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),156灡3(s,C灢4曚),102灡0(d,C灢1曞),74灡7(d,
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),
62灡4(t,C灢6曞).(Tanakaetal灡,1982)
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
copyranosyl)灢1灢propanone (13)wasobtainedasyelow
powder,C21H24O9;1H灢NMR (CD3OD,500MHz):毮H
7灡24(4H,m,H灢2曚,3曚,5曚,6曚),7灡13(1H,m,H灢4曚),
6灡18(1H,d,J=2灡2,H灢6),6灡95(1H,d,J=2灡2,
H灢8),5灡03(1H,d,J=7灡1,H灢1曞),3灡90(1H,dd,J
=12灡1,2灡2,H灢6曞),3灡70(1H,dd,J = 12灡1,5灡5,
H灢6曞),3灡30 (2H,overlapped,H灢3),3灡52灢3灡35 (3H,
m,H灢3曚,4曚,5曚),2灡97(2H,t,H灢2);13C灢NMR (CD3
OD,125 MHz):毮C 31灡7 (t,C灢2),46灡6 (t,C灢3),
206灡4(s,C灢4),162灡5(s,C灢5),98灡5(d,C灢6),167灡7
(s,C灢7),95灡7(d,C灢8),166灡1(s,C灢9),107灡0(s,C灢
10),143灡2(s,C灢1曚),129灡6(d,C灢2曚,6曚),129灡5(d,
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,
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),
62灡6(t,C灢6曞).(Hegdeetal灡,2003)
naringenin灢7灢O灢毬灢D灢glucopyranoside(14)wasob灢
tainedasyelowamorphouspowder,C21 H22 O10;1H灢
NMR(Pyridine灢d5,500MHz):毮H 7灡51(2H,d,J=
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
(1H,d,J=2灡2,H灢8),6灡58(1H,d,J=2灡2,H灢6),
5灡75(1H,d,J =7灡8,H灢1曚),5灡42 (1H,dd,J =
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
(1H,dd,J=12灡6,16灡9,H灢3毬),2灡89(1H,dd,J=
16灡9,3灡0,H灢3毩);13C灢NMR (Pyridine灢d5,125MHz):
毮C80灡0 (d,C灢2),43灡5 (t,C灢3),197灡5 (s,C灢4),
166灡9(s,C灢5),97灡9(d,C灢6),164灡8(s,C灢7),96灡7
(d,C灢8),163灡9(s,C灢9),104灡6(s,C灢10),129灡8(s,
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
(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,
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).
(Luetal灡,2007)
vitexin (8灢C灢毬灢D灢glucopyranosylapigenin) (15)
wasobtainedasyelowamorphouspowder,C21H20O10;
1H灢NMR(DMSO灢d6,500MHz):毮H8灡02(2H,d,J=
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
(1H,s,H灢3),6灡27(1H,s,H灢6),5灡06(1H,d,J=
5灡3,H灢1曞),5灡03(1H,d,J=4灡1,H灢1曞),4灡67(2H,
m,H灢2曞,5曞),3灡83 (1H,t,J =9灡4,H灢3曞),3灡76
(1H,m,H灢4曞),3灡25(2H,m,H灢6曞);13C灢NMR(DM灢
SO灢d6,125MHz):毮C164灡1(s,C灢2),102灡5(d,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
(s,C灢7),104灡1(s,C灢8),156灡1(s,C灢9),104灡7(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,
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
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),
61灡4(t,C灢6曞).(Huetal灡,2006)
7灢O灢毬灢D灢glucopyranosylchrysin(16)wasobtained
asyelowamorphouspowder,C21H20O9;1H灢NMR(Pyr灢
idine灢d5,500MHz):毮H7灡92(1H,d,J=1灡3,H灢2曚),
7灡90(1H,d,J=1灡9,H灢6曚),7灡50(1H,d,J=2灡4,
064暋暋暋暋暋暋暋暋暋暋暋暋 暋暋暋暋暋暋暋云暋南暋植暋物暋研暋究暋暋暋暋暋暋暋暋暋暋暋暋暋暋暋暋第32卷
H灢6),7灡45(3H,m,H灢3曚,4曚,5曚),7灡05(1H,d,J=
2灡4,H灢3),6灡96(1H,s,H灢8),5灡43(1H,d,J=7灡5,
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,
5曚,6曚),4灡06(1H,m,H灢3曞);13C灢NMR (Pyridine灢d5,
125MHz):毮C165灡0(s,C灢2),109灡9(d,C灢3),178灡5
(s,C灢4),160灡6(s,C灢5),105灡8(d,C灢6),161灡8(s,C灢
7),99灡8(d,C灢8),160灡0(s,C灢9),109灡3(s,C灢10),
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),
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),
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
(t,C灢6曞).(Eletal灡,2004)
isorhamnetin3灢O灢毩灢L灢rhamnopyranosyl灢7灢O灢毬灢D灢
glucopyranoside(17)wasobtainedasyelowpowder,C28
H32O16;1H灢NMR (CD3OD,500MHz):毮H7灡95(1H,
d,J=1灡7,H灢2曚),7灡63 (1H,dd,J=8灡8,1灡7,H灢
6曚),6灡92(1H,d,J=8灡8,H灢5曚),6灡42(1H,d,J=
2灡2,H灢8),6灡22(1H,d,J=2灡2,H灢6),5灡24(1H,d,
J=7灡1,H灢1曞),4灡53 (1H,s,H灢1熓),3灡95 (3H,s,
OMe),3灡82(1H,d,J=11灡0,H灢2熓),3灡61(1H,s,
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),
1灡10(3H,d,J=6灡6,H灢6曞);13C灢NMR (CD3OD,125
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),
95灡1(d,C灢8),158灡7(s,C灢9),105灡9(s,C灢10),123灡2
(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,
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
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),
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,
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
5熓),18灡0(q,C灢6熓),57灡0(q,OMe).(Wolbis,1989)
kaempferol灢3灢O灢毬灢D灢glucopyranoside(18)wasob灢
tainedasyelowamorphouspowder,C21 H20 O11;1H灢
NMR(Pyridine灢d5,500MHz):毮H 8灡43(2H,d,J=
9灡0,H灢2曚,6曚),7灡19 (1H,d,J =7灡2,H灢8),6灡70
(2H,dd,J=7灡2,2灡0,H灢3曚,5曚),6灡32(1H,d,J=
7灡2,H灢6),4灡40灢4灡03 (6H,m,H灢sugar);13C灢NMR
(Pyridine灢d5,125MHz):毮C157灡7(s,C灢2),135灡2(s,
C灢3),178灡9(s,C灢4),157灡5(s,C灢5),99灡9(s,d,C灢
6),166灡0(s,C灢7),94灡7 (d,C灢8),162灡9 (s,C灢9),
105灡4(s,C灢10),122灡1(s,C灢1曚),132灡0(d,C灢2曚,6曚),
116灡2(d,C灢3曚,5曚),161灡7(s,C灢4曚),104灡0(d,C灢1曞),
79灡2(d,C灢5曞),78灡5(d,C灢3曞),76灡1(d,C灢2曞),71灡5
(d,C灢4曞),62灡6(t,C灢6曞).(Chenetal灡,2009)
kaempferol灢3灢O灢毬灢D灢(6曞灢O灢trans灢p灢coumaroyl)
glucopyranoside(19)wasobtainedasyelowamorphous
powder,C30H26O13;1H灢NMR(CD3OD,500MHz):毮H
7灡91(2H,d,J=8灡9,H灢2曚,6曚),7灡34(1H,d,J=
15灡9,H灢3熓),7灡22(2H,d,J=8灡5,H灢5熓,9熓),6灡74
(2H,d,J=8灡9,H灢3曚,5曚),6灡72(2H,d,J=8灡5,H灢
6熓,8熓),6灡20(1H,d,J=1灡9,H灢8),6灡05(1H,d,J
=2灡1,H灢6),6灡02 (1H,d,J =15灡9,H灢2熓),5灡20
(1H,dd,J=1灡9,5灡6,H灢1曞);13C灢NMR(CD3OD,125
MHz):毮C159灡3(s,C灢2),135灡4(s,C灢3),179灡4(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),
95灡0(d,C灢8),158灡3(s,C灢9),105灡6(s,C灢10),122灡7
(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,
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
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),
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
(d,C灢2熓),146灡7 (d,C灢3熓),127灡1 (s,C灢4熓),131灡3
(d,C灢5熓),116灡9 (d,C灢6熓),161灡2 (s,C灢7熓),116灡9
(d,C灢8熓),131灡3(d,C灢9熓).(Tsukamotoetal灡,2004)
Acknowledgement:Theauthorsaregratefultothemem灢
bersoftheanalyticalgroupoftheStateKeyLaboratoryof
PhytochemistryandPlantResourcesinWestChina,Kun灢
mingInstituteofBotany,ChineseAcademyofSciences
foralofthespectralmeasurements.
Reference:
AnderssonR,LundgrenLN,1988.Theconstituentsofconifernee灢
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《云南植物研究》征订启事
《云南植物研究》创刊于1979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
期刊。经过30年的努力,现已成为我国植物科学研究发表论文的主要学术性刊物之一,已被选为 “中国自然科学核
心期刊暠,“中国生物学类科技核心期刊暠。本刊荣获中科院优秀期刊二等奖 (1996)及一等奖 (2000)、第二届全国优
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一,2002年入选国家 “双效期刊暠。本刊所发表的论文在国内生物、农林、医药、轻工等二次文献刊物都有摘报;国
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有一定的影响。目前已加中国学术期刊光盘版、中国学术期刊网及万方数据库资源系统。本刊主要报道植物学各分支
学科具有创造性或较高学术水平的研究论文和简报;植物学领域的新发现及重大应用价值的新成果;有关植物学资源
开发利用和保护的创新性研究成果;植物学研究的新技术、新方法;反映本学科重要领域的国内外植物科学研究的最
新进展的评述,中英文稿件均受欢迎。本刊设有植物系统学与生物地理学、植物化学与化学生物学、生物多样性保护
与民族植物学、植物生态学与资源管理、植物生理与分子生物学5个专栏。
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