全 文 ：天然产物研究与开发 NatProdResDev2008, 20:765-769
文章编号:1001-6880(2008)05-0765-05
ReceivedJuly30, 2008;AcceptedOctober7, 2008
＊CorrespondingauthorTel:86-24-23986289;E-mail:lifamei@syphu.
edu.cn
无梗五加果化学成分的研究
安 琪 ,杨春娟 ,宋 洋 ,于 凯 ,熊志立 ,李发美＊
沈阳药科大学药学院 , 沈阳 110016
摘 要:从无梗五加 (Acanthopanaxsesiliflorus(Rupr.etMaxim.)Seem.)果 70%乙醇提取物中分离鉴定了 12
个化合物。经波谱鉴定为东莨菪内酯 (1),原儿茶酸甲酯 (2), 槲皮素 (3),无梗五加苷 B(4), 金丝桃苷 (5),
(-)-pinoresinol-4, 4′-di-O-β-D-glucopyranoside(6), chiisanoside(7), 22α-hydroxychiisanoside(8), niduloicacid
(9), 胡萝卜苷 (10), 东莨菪苷 (11)和无梗五加苷 D(12)。其中化合物 9为新天然产物 , 化合物 1, 2, 6和 11
是首次从五加科植物中分离得到 ,化合物 3是首次从五加属植物中分离得到。
关键词:五加属;无梗五加;niduloicacid;东莨菪内酯;东莨菪苷;原儿茶酸甲酯;(-)-pinoresinol-4, 4′-di-O-β-D-
glucopyranoside;槲皮素
中图分类号:R284.1;Q946.91 文献标识码:A
StudiesontheChemicalConstituentsofthe
FruitofAcanthopanaxsessiliflorus(Rupr.etMaxim.)Seem.
ANQi, YANGChun-juan, SONGYang, YUKai, XIONGZhi-li, LIFa-mei＊
SchoolofPharmacy, ShenyangPharmaceuticalUniversity, Shenyang110016 , China
Abstract:Twelvecompoundswereisolatedfromthe70% ethanolextractofthefruitofAcanthopanaxsessiliflorus(Ru-
pr.etMaxim.)Seem., whichwasfractionatedonamacroporousresincolumnby60% and30% ethanol.Theywerei-
dentifiedasscopoletin(1), protocatechuicacidmethylester(2), quercetin(3), acanthosideB(4), hyperin(5), (-)-
pinoresinol-4, 4′-di-O-β-D-glucopyranoside(6), chisanoside(7), 22α-hydroxychiisanoside(8), niduloicacid(9),
daucosterol(10), scopolin(11), andacanthosideD(12), byanalysisoftheirspectroscopicdataandbycomparison
withthosereportedontheliterature.Compound9 wasanewnaturalproduct.1, 2, 6and11wereisolatedfromAraliaceae
forthefirsttimeand3 wasobtainedfromAcanthopanaxgenusforthefirsttime.
Keywords:Acanthopanax;Acanthopanaxsessiliflorus(Rupr.etMaxim.)Seem.;niduloicacid;scopoletin;scopolin;
protocatechuicacidmethylester;(-)-pinoresinol-4, 4′-di-O-β-D-glucopyranoside;quercetin
Introduction
Acanthopanaxsessiliflorus(Rupr.etMaxim.)Seem.
mainlydistributesinChina, JapanandKorea.Itsfruit
isusedasfolkmedicineforhypertension, dizzinessand
MenopausalWomen sSyndrome[ 1] .However, upto
now, onlyafewchemicalconstituents, suchasursolic
acid[ 2] , scoparone[ 2] , hyperin[ 2, 3] , sessiline[ 4] , have
beenisolatedfromthefruitofAcanthopanaxsessiliflorus
(Rupr.etMaxim.)Seem..Tofurtherinvestigatethe
constituentsandscreenthebioactivecompoundsfrom
itsfruit, thephytochemicalstudywasperformed.Inthis
paper, twelvecompoundswereisolatedfromthe70%
ethanolextractofthefruitofA.sessiliflorus(Rupr.et
Maxim.)Seem., whichwasfractionatedonamacro-
porousresincolumnby60% and30% ethanol.They
wereidentifiedasscopoletin(1), protocatechuicacid
methylester(2), quercetin(3), acanthosideB(4),
hyperin(5), (-)-pinoresinol-4, 4′-di-O-β-D-glucopyr-
anoside(6), chisanoside(7), 22α-hydroxychisano-
side(8), niduloicacid(9), daucosterol(10), scopo-
lin(11), andacanthosideD(12)(Fig.1).Com-
pound9wasanewnaturalproduct.1, 2, 6 and11were
isolatedfromAraliaceaeforthefirsttimeand3wasob-
tainedfromAcanthopanaxgenusforthefirsttime.
MaterialsandMethods
Generalprocedures
Silicagel(200-300 mesh, QingdaoHaiyangChemical
Co.Ltd.Qingdao, China), D101 macroporousadsorp-
tionresin(Nankaiuniversitychemicalplant, Tianjin,
China), SephedaxLH-20 (PharmaciaFineChemical
Co.Ltd.Sweden)andsilicagel(GF254 , QingdaoHaiy-
angChemicalCo.Ltd.Qingdao, China)wereusedfor
columnchromatography(CC)andTLC, respectively.
PreparativeHPLCanalysiswascarriedoutonAgilent
1100seriesHPLCwithaZORBAXSB-C18 PrepHTcol-
umn(21.2 ×250 mm, 7 μm)andeluentofMeOH-
H2Oataflowrateof9.0 mL/min.AnalyticalHPLCa-
nalysiswasperformedonShimadzuSPD-10AHPLC
withaDiamonsilTM C18 column(4.6 × 200 mm, 5
μm)andeluentofMeOH-H2Oataflowrateof0.7
mL/min.MeltingpointwasmeasuredonanX-4 melt-
ingpointapparatus(BeijingTechInstruCo.Ltd.Chi-
na)andthethermometerwasnotcorected.Opticalro-
tationwasmeasuredonaPERKIN-ELMER241MCpo-
larimeter.NMRspectrawererecordedonBrukerARX-
300 MHzNMR spectrometerwithTMSasinternal
standard, thechemicalshiftvalueswerereportedin
ppm(δ)andcouplingconstants(J)giveninHz.
MassspectraweredeterminedonaMicromass Quat-
tromicroTMAPImassspectrometer.
Plantmaterials
ThefruitsofA.sesiliflorus(Rupr.etMaxim.)Seem.
werecolectedfromWujiaAgricultureSci-TechCo.
Ltd.ofDandong, LiaoningProvince, ChinainOctober,
2006andidentifiedbyAsociateProfessorJincaiLuof
SchoolofTraditionalChineseMateriaMedicaofSheny-
angPharmaceuticalUniversity, China.Avoucherspeci-
men(WGWJ061001)wasdepositedintheherbarium
oftheGroupofPharmaceuticalChromatographicAnal-
ysis, SchoolofPharmacy, ShenyangPharmaceuticalU-
niversity, Shenyang, China.
Extractionandisolation
Thedriedandpowderedfruits(12 kg)ofA.sessiliflo-
rus(Rupr.etMaxim.)Seem.wereextractedwith70%
EtOH(3 ×96 L)underreflux.Thecombinedextract
wasconcentratedundervacuumtoyieldaresidue(5.8
kg)whichwasdissolvedinwater, loadedonaD101
macroporousadsorptionresincolumnandelutedwith
H2O, 30% EtOH, 60% EtOHand95% EtOH, succes-
sively.The60% EtOHeluatewasevaporatedtodry-
nesstogivearesiduewhichwasdissolvedinMeOH
andfiltered.Thefiltratewasconcentratedtoyield40 g
ofresiduewhichwaschromatographedonasilicagel
columnwithCHCl3 -MeOH(100∶0※ 0∶100)asthe
eluent.Sixmajorfractions:Fr.A(100∶1), Fr.B(30∶1),
Fr.C(15∶1), Fr.D(8∶1), Fr.E(5∶1)andFr.F(2∶1)
werecolected.Fr.AwasloadedonaSephedaxLH-20
column(2 × 50 cm)andelutedwithCHCl3 -MeOH
(1∶1)toaford1 (10 mg).Fr.Bwasseparatedona
silicagelcolumn(2.5 ×60cm)usingagradientelu-
entofCHCl3 -MeOH.ThefractionofCHCl3-MeOH(20
∶1)wassuccessivelypurifiedonaSephedaxLH-20
column(2 ×50 cm)elutedwithMeOHafording2
(8 mg).Fr.CwassubjectedtopreparativeHPLCona
ZORBAXSB-C18 PrepHTcolumn(21.2 ×250mm, 7
μm)elutedwithMeOH-H2Otogive3 (50∶50, tR =
9.5 min, 2mg)and4(42.5∶57.5, tR=18.4 min, 15
mg).Fr.DwaspurifiedbyrecrystalizationfromMeOH
toaford5 (150 mg).Fr.Ewaschromatographedona
silicagelcolumn(2.5 ×60 cm)withagradientof
mixtureofCHCl3-MeOH(5∶1※2∶1)toyieldsubfrac-
tionwhichwasfurtherpurifiedonthepreparative
HPLCcolumnwithMeOH-H2Oastheeluenttogive6
(55∶45, tR =7.6 min, 5 mg).Fr.Fwaschromato-
graphedonthepreparativeHPLCcolumnwithMeOH-
H2Oastheeluenttogive7(53∶47, tR=16.7min, 10
mg)and8 (48∶52, tR=28.1 min, 10mg).
The30% EtOHeluatewasevaporatedtodrynessto
givearesiduewhichwasdissolvedinMeOH-H2O(60
∶40)andfiltered.Thefiltratewasconcentratedtoaf-
ford60gresiduewhichwaschromatographedonasili-
cagelcolumnwithCHCl3-MeOH(50∶1※1∶1)asthe
eluentafordingfourmajorfractions:Fr.G(20∶1), Fr.
H(10∶1), Fr.I(10∶1)andFr.J(5∶1).Fr.Gwas
purifiedbyrecrystalizationfromCHCl3 togive9 (7
mg).Frs.H-Jwerepurifiedbyrecrystalizationfrom
MeOHtogive10 (15 mg), 11 (15 mg)and12 (13
mg), respectively.
766 NatProdResDev Vol.20
Fig.1 Structuresofcompounds1-9, 11, and12
StructureIdentification
Scopoletin(1) Lightyelowneedles.ESI-MSm/z:
191 [ M-H] -.1HNMR(300 MHz, MeOH)δ:7.87
(1H, d, J=9.4 Hz, H-4), 7.11 (1H, s, H-5), 6.77
(1H, s, H-8), 6.20 (1H, d, J=9.5 Hz, H-3), 3.91
(3H, s, -OCH3);13CNMR(75MHz, MeOH)δ:164.0
(C-2), 152.9 (C-7), 151.4 (C-9), 147.0 (C-4),
146.1 (C-6), 112.6 (C-5), 110.9 (C-10), 109.9
(C-3), 103.9(C-8), 59.7(-OCH3).Thesedatawere
consistentwiththoseofscopoletin[ 5] .
Protocatechuicacidmethylester(2) Whitenee-
dles, mp.136-138 ℃.ESI-MSm/z:167 [ M-H] -.1H
NMR(300 MHz, MeOH)δ:7.27 (1H, brs, H-2),
7.25(1H, d, J=8.2Hz, H-6), 6.66 (1H, d, J=8.3
Hz, H-5), 3.67 (3H, s, -OCH3);13CNMR(75 MHz,
MeOH)δ:167.5 (-COOCH3), 150.2 (C-4), 144.8
(C-3), 122.2 (C-6), 121.2 (C-1), 116.0 (C-2),
114.4 (C-5), 50.8 (-COOCH3).Thesedatawerei-
denticalwiththoseofprotocatechuicacidmethylester
[ 6] .
Quercetin(3) Yelowcrystal, mp.312-315 ℃.ESI-
MSm/z:303 [ M+H] + , 341 [ M+K] + , 301 [ M-
H] -.1HNMR(300 MHz, DMSO-d6)δ:12.48 (1H,
s, 5-OH), 7.69 (1H, s, H-2′), 7.50 (1H, d, J=7.3
Hz, H-6′), 6.89 (1H, d, J=8.4 Hz, H-5′), 6.40
(1H, s, H-8), 6.19 (1H, s, H-6);13 CNMR(75
MHz, DMSO-d6)δ:175.8(C-4), 146.8(C-2), 135.7
(C-3), 103.0 (C-10), 164.0 (C-7), 156.2 (C-5),
160.7 (C-9), 145.1 (C-3′), 147.8 (C-4′), 122.0
(C-1′), 120.0 (C-6′), 116.1 (C-5′), 115.1 (C-
2′), 98.2(C-6), 93.4(C-8).Thesedatawereidenti-
calwiththoseofquercetin[ 7] .
AcanthosideB(4) Whitepowder, mp.192-193 ℃.
[ α] 25D-38°(c1.0, DMSO).ESI-MSm/z:579 [ M-
H] -.1HNMR(300 MHz, DMSO-d6)δ:3.81, 4.20
(4H, m, H-4, H-8), 3.76 (12H, s, 4 × -OCH3 ),
6.60, 6.73(4H, s, aromHonsyringylring);13CNMR
spectraldataaregiveninTable1.Thesedatawere
consistentwiththoseof(+)-syringaresinol-O-β-D-
glucopyranoside(acanthosideB)[ 8] .
Hyperin(5) Yelowpowder, mp.238-239 ℃.ESI-
MSm/z:465 [ M+H] + , 487 [ M+Na] +, 463 [ M-
H] -.1HNMR(300 MHz, DMSO-d6)δ:12.60 (1H,
s, 5-OH), 6.19 (1H, d, J=1.8 Hz, H-6), 6.39 (1H,
d, J=1.8 Hz, H-8), 6.81 (1H, d, J=8.4 Hz, H-
5′), 7.51 (1H, d, J=1.8 Hz, H-2′), 7.65 (1H, d, J
=8.4Hz, H-6′), 5.35(1H, d, J=7.8Hz, H-1ofga-
lactose);13CNMR(75MHz, DMSO-d6)δ:177.7 (C-
4), 164.4 (C-7), 161.4 (C-5), 156.5 (C-2), 156.4
(C-9), 148.7 (C-4′), 145.0 (C-3′), 133.7 (C-3),
122.2 (C-6′), 121.3 (C-1′), 116.1 (C-5′), 115.4
(C-2′), 104.0 (C-10 ), 98.9 (C-6), 93.7 (C-8),
102.0 (GalC-1″), 76.0 (GalC-5″), 73.4 (GalC-
3″), 71.4 (GalC-2″), 68.1 (GalC-4″), 60.3 (Gal
C-6″).Thesedatawereconsistentwiththoseofhyperin
[ 3] .
(-)-Pinoresinol-4, 4′-di-O-β-D-glucopyranoside(6)
Colorlessneedles, mp.220-221 ℃.[ α] 25D -76°(c1.0,
C5H5N).1HNMR(300 MHz, C5D5N)δ:5.69 (1H,
d, J=7.8 Hz, H-1 ofGlc), 3.75 (3H, s, -OCH3),
6.99 (1H, d, J=7.2 Hz, H-5′, 5″), 7.19 (1H, s, H-
2), 7.22(1H, s, H-6′, 6″).13CNMRspectraldataare
giveninTable1.Thesedatawereconsistentwiththose
767Vol.20 ANQi, etal:StudiesontheChemicalConstituentsoftheFruitofAcanthopanaxsessiliflorus(Rupr.etMaxim.)Seem.
of(-)-pinoresinol-4, 4′-di-O-β-D-glucopyranoside[ 9] .
Chisanoside(7) Whitepowder.ESI-MSm/z:977
[ M+Na] +.1HNMR(300 MHz, C5D5N)δ:0.99,
0.99, 1.09, 1.62 , 1.80 (each3H, s, 5 × -CH3),
1.70(3H, d, J=6.0Hz, H-6ofRha), 3.07(3H, d, J
=14.4 Hz, H-2), 4.98 (1H, d, J=7.7 Hz, H-1 of
outerGlc), 5.85(1H, s, H-1 ofRha), 6.35(1H, d, J
=8.1 Hz, H-1ofinnerGlc).13CNMRspectraldata
aregiveninTable1.Compound7wasidentifiedaschi-
isanosidebycomparisonofthespectraldatawiththe
reporteddata[ 10] .
22α-Hydroxychisanoside(8) Whitepowder.ESI-
MSm/z:993 [ M +Na] +.1H NMR(300 MHz,
C5D5N)δ:1.02, 1.13, 1.15, 1.89, 1.90 (each3H, s,
5 ×-CH3), 1.74 (3H, d, J=6.3 Hz, H-6 ofRha),
3.58(1H, brs, H-19), 3.77 (1H, brs, H-1), 4.56
(1H, brs, H-11), 4.72 (1H, brs, H-29a), 4.77
(1H, d, J=4.8Hz, H-22), 4.98 (1H, d, J=7.7 Hz,
H-1 ofouterGlc), 5.84 (1H, s, H-1 ofRha), 6.38
(1H, d, J=8.1Hz, H-1 ofinnerGlc);13CNMRspec-
traldataaregiveninTable1.Compound8 wasidenti-
fiedas22α-hydroxychisanosidebycomparisonofthe
spectraldatawiththereporteddata[ 10] .
Niduloicacid(9) Colorlessneedles, mp.151-152
℃.ESI-MSm/z:233 [ M+Na] + , 209 [ M-H] -.1H
NMR(300 MHz, DMSO-d6)δ:7.01 (2H, dd, J=
8.4, 2.8 Hz, H-2′, 6′), 6.98 (2H, dd, J=8.4, 2.8
Hz, H-3′, 5′), 2.55 (2H, t, J=7.0 Hz, H-2), 1.75
(2H, m, H-4), 3.99(2H, m, H-3), 2.67, 2.59 (2H,
m, H-5);13CNMR(75MHz, DMSO-d6)δ:175.6 (C-
1), 40.3(C-2), 68.7(C-3), 43.2 (C-4), 31.9 (C-
5), 134.0 (C-1′), 130.3 (C-2′), 116.1 (C-3′),
156.4 (C-4′), 116.1 (C-5′), 130.3 (C-6′).Com-
pound9 wasidentifiedasniduloicacid[ 3-hydroxy-5-
(p-hydroxyphenyl)pentanoicacid] bycomparisonof
thespectraldatawiththereporteddata[ 11].
Daucosterol(10) Whitepowder, mp.285-287 ℃.
TLCbehaviorwasidenticalwiththatofauthenticdau-
costerol.
Scopolin(11) Colorlesspowder, mp.217-219 ℃.
[ α] 25D -89.8°(c0.12, MeOH).ESI-MSm/z:377 [ M
+Na] +.1HNMR(300 MHz, DMSO-d6 )δ:7.97
(1H, d, J=9.5 Hz, H-4), 6.33 (1H, d, J=9.5 Hz,
H-3), 7.30 (1H, s, H-5), 7.15 (1H, s, H-8), 5.34
(1H, s, H-1ofGlc), 3.81 (3H, s, -OCH3);13CNMR
(75 MHz, DMSO-d6)δ:160.6(C-2), 113.4 (C-3),
144.3 (C-4), 109.8 (C-5), 146.1(C-6), 149.9(C-
7), 103.1 (C-8), 149.1 (C-9), 112.4 (C-10), 56.1
(-OCH3), 99.7 (GlcC-1′), 73.2 (GlcC-2′), 77.2
(GlcC-3′), 69.7(GlcC-4′), 76.8 (GlcC-5′), 60.7
(GlcC-6′).Compound11 wasidentifiedasscopolin
bycomparisonofthespectraldatawiththereportedda-
ta[ 12].
AcanthosideD (12) Whitepowder, mp.248-250
℃.[ α] 25D-28°(c1.0, DMSO).1HNMR(300 MHz,
DMSO-d6)δ:4.98(1H, d, J=7.8Hz, H-1 ofGlc), 3.75
(12H, s, 4 ×-OCH3), 6.65 (2H, s, Hofbenzenering).
13CNMRspectraldataaregiveninTable1.Thesedata
wereconsistentwiththoseofacanthosideD[ 13].
Table1 13CNMRspectraldataofcompounds4, 6-8and12
C 4 6 12 C 7 8 C 7 8
1 53.6 54.7 53.7 1 70.2 70.6 25 18.8 19.2
5 53.7 2 38.5 38.8 26 17.7 18.1
4 71.3 72.0 71.5 3 172.8 173.1 27 13.5 13.9
8 4 147.4 147.8 28 174.8 174.9
2 85.4 86.0 85.2 5 49.4 49.6 29 110.4 111.2
6 85.1 6 24.9 25.2 30 18.6 18.8
1′ 133.7 135.3 133.8 7 33.2 32.4 28-O-innerGlc-1 95.1 95.5
1″ 131.4 8 41.4 41.8 2 73.8 73.9
2′ 104.2 111.3 104.3 9 43.8 44.2 3 78.4 78.3
2″ 103.7 10 43.8 44.4 4 70.5 70.8
768 NatProdResDev Vol.20
3′ 152.7 150.2 152.7 11 75.0 75.0 5 76.2 77.2
3″ 147.9 12 31.9 33.6 6 69.0 69.5
4′ 137.2 147.4 137.2 13 35.0 35.1 outerGlc-1 104.8 105.2
4″ 134.9 14 41.9 42.2 2 75.0 75.3
5′ 152.7 116.3 152.7 15 30.4 29.1 3 76.8 76.4
5″ 147.9 16 32.0 26.8 4 78.0 78.7
6′ 104.2 119.0 104.3 17 56.5 62.9 5 77.7 78.0
6″ 103.7 18 47.3 44.2 6 60.9 61.3
-OCH3 56.5 56.0 56.5 19 49.4 47.8 terminalRha-1 102.5 102.8
-OCH3 56.0 20 150.0 150.6 2 72.4 72.6
Glc-1′, 1″ 102.7 102.2 102.8 21 29.3 41.8 3 72.3 72.7
2′, 2″ 74.2 74.9 74.3 22 36.5 75.5 4 73.8 74.1
3′, 3″ 76.6 78.9 76.5 23 113.6 113.9 5 70.2 70.4
4′, 4″ 70.0 71.3 70.0 24 23.2 23.5 6 18.2 18.5
5′, 5″ 77.2 78.6 77.3
6′, 6″ 61.0 62.4 61.0
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