全 文 :116 ChinJNatMed Mar.2008 Vol.6 No.2 2008年 3月 第 6卷 第 2期
ChemicalConstituentsofClematismontana
SONGCheng-Zhi1, 2 , WANGYue-Hu2 , HUAYan1 , WUZhang-Kang1 , DUZhi-Zhi2*
1SchoolofNatrualResources, SouthwestForestUniversity, Kunming650224;
2KunmingInstituteofBotany, ChineseAcademyofSciences, Kunming650204 , P.R.China
【ABSTRACT】 AIM:TostudythechemicalconstituentsofClematismontanaBuch.-Ham.exDC..METHODS:
AerialpartoftheplantwasextractedbyethanolfirstlyandthentheethylacetatepartoftheethanolextractwasisolatedbydiferentcolumnchromatographictechniquesincludingsilicagelandSephadexLH-20.Structuresofthesecom-poundswereidentifiedonthebasisofspectroscopicanalysis.RESULTS:Fourteencompoundswereisolatedandtheir
structuresweredeterminedtobeconiferaldehyde(1), cafeicacid(2), pluchoicacid(3), protocatechualdehyde(4),vanilin(5), hydroxytyrosol(6), 4-carbonyl-5-hydroxymethylvalerate(7), 4-hydroxydodec-2-enedioicacid(8),
(+)-dihydrodehydrodiconiferylalcohol(9), (-)-syringaresinol(10), (+)-guayarol(11), (-)-arctiin(12),(-)-lariciresinol(13), andhyperin(14).CONCLUSION:Allthecompoundswereobtainedfromthisplantforthefirsttime.
【KEYWORDS】 Clematismontana;Ranunculaceae;Lignans;Flavonoids【CLCNumber】 R284 【Documentcode】 A 【AriticleID】 1672-3651(2008)02-0116-04
doi:10.3724/SP.J.1009.2008.00116
【Receivedon】 2007-10-08
【FoundationItem】 ThisprojectwassupportedbytheXi-
BuZhiGuangProjectofChineseAcademyofSciencesandNationalNa-
tureScienceFoundationofChina(No.30400038)
【*Correspondingauther】 DUZhi-Zhi:associateprofessor, en-
gagedinstudiesofmedicalandaromaticplants, Tel:86-871-5223224,
Fax:86-871-5150227, E-mail:duzhizhi@mail.kib.ac.cn
1 Introduction
ThegenusofClematis(Ranunculaceae)contai-ningabout355 speciesiswidelydistributedintheworld.Thereare155 speciesinChina, among101areendemic.ClematismontanaBuch.-Ham.exDC., awoodyclimber, usualygrowsinmountainslopes, valeys, andgrasslands, andisdistributedinTibet, Sichuan, Guizhou, GuangxiandYunnan[ 1] .Asafolkmedicinalherb, thestemsofthisplantareusedfordropsy, cystitis, proctoptosiswithchronic
dysentery, urethritisandgalactostasis[ 2] whiletheleavesforskindiseases.Inaddition, itsseedshavepurgingproperties[ 3, 4] .Asforthechemicalconstitu-entsofC.montana, onlysometriterpenenesaponins
werereported[ 3, 4] .Inordertoinvestigatethebioac-tiveconstituentsofthisplantwehavecarriedoutadetailedchemicalstudyonthisplantandfourteenknowncompoundswereisolatedfromtheethylace-tatepartoftheethanolextractoftheplant.Thesecompoundswereidentifiedasconiferaldehyde(1),cafeicacid(2), pluchoicacid(3), protocatechual-dehyde(4), vanilin(5), hydroxytyrosol(6), 4-carbonyl-5-hydroxy methyl valerate (7 ), 4-hydroxydodec-2-enedioicacid(8), (+)-dihydrode-
hydrodiconiferylalcohol(9), (-)-syringaresinol(10), (+)-guayarol(11), (-)-arctin(12),(-)-lariciresinol(13), andhyperin(14).
2 Experimental
2.1 GeneralThinlayerchromatographywasperformedonsil-icagelGF254 plates(QingdaoMeigaoChemicalCo.,Ltd).TLCdevelopingagentis5% sulphuricacidinethanol.OpticalrotationsweredeterminedonaJAS-CODIP370digitalpolarimeter.Columnchromatogra-phywascarriedoutonsilicagel(200-300 mesh;QingdaoMakalGroupCo., Ltd), SephadexLH-20(GEHealthcareBio-SciencesAB), RP-18 gel(40-
63μm;Merck, Darmstadt, Germany), andMCIresin(75-150 μm, MitsubishiChemicalCorporation).PreparativeTLCwascariedoutonsilicagelGF254.MSdataweremeasuredonaVGAutoSpec3000massspectrometer.AltheNMRdatawereobtainedatroomtemperatureonAM-400 andDRX-500 spec-trometers(TMSasinternalreference, chemicalshiftinδ).
2.2 PlantMaterialTheaerialpartsofClematismontanawerecol-lectedinLijiangofYunnanProvince, China, inAu-gust2006, andidentifiedbyProf.PUChun-Xia.Avoucherspecimen(No.0866446)wasdepositedinHerbariumofKunmingInstituteofBotany, ChineseAcademyofSciences.
2.3 ExtractionandIsolationTheair-driedaerialpartsofC.montana(4.8kg)weregroundandextractedwith90% EtOH(10L×3).Theextractedliquidwascombinedandcon-
2008年 3月 第 6卷 第 2期 ChinJNatMed Mar.2008 Vol.6 No.2 117
centratedinvacuumonarotaryevaporator.Theresi-duewassuspendedinwaterandextractedsuccessive-lywithpetroleumether(2 L×3), EtOAc(2L×
5)andn-BuOH(2 L×4).TheEtOAcextract(60g)wassubjectedtosilicagelchromatography, elutedwithCHCl3 -Me2CO(1∶0to0∶1)toprovidefractions
1-12.Fraction1(560 mg)wassubjectedtorepeatedcolumnchromatographyonsilicagel, elutedwithpe-troleumether-Me2CO(20∶1 to2∶1)toyield1 (8mg)and5(4mg).Fraction2(790mg)wassubjec-tedtoSephadexLH-20 columnchromatographyelu-
tedwithMeOHtoyield10(7 mg), 11(15mg)and
13(6 mg).Fraction7 (2.5 g)wassubjectedtoSephadexLH-20 CCelutedwithMeOHtoyield4 (8mg), 8 (13 mg), 9 (18 mg), 6 (11 mg), 3 (22mg)and2 (67mg).Fraction8 (3.8g)wassubjec-tedtorepeatedcolumnchromatographyonsilicagel,elutedwithpetroleumether-EtOAc(5∶1 to0∶1)toyield7 (22 mg).Fraction12 (12 g)wassubjectedtoSephadexLH-20 columnchromatographyelutedwithMeOHtoyield12 (13 mg)and14 (200mg).
3 Identification
Coniferaldehyde[ 5] (1) Whitepowder(CHCl3);
1HNMR(CDCl3 , 400MHz)δ:7.08(1H, d, J=
1.6Hz, H-2), 6.97 (1H, d, J=8.2 Hz, H-5),
7.13 (1H, dd, J= 8.2, 1.7 Hz, H-6), 7.41(1H, d, J=15.8Hz, H-7), 6.61(1H, dd, J=
15.8, 7.7 Hz, H-8), 9.66(1H, d, J=7.8 Hz,H-9), 3.95(3H, s, -OMe);13CNMR(CDCl3 , 100MHz)δ:126.6 (C-1), 109.5 (C-2), 147.0 (C-
3), 149.0 (C-4), 115.0 (C-5), 124.1 (C-6),
153.2 (C-7), 126.4(C-8), 193.7 (C-9), 56.0 (-OMe).
Cafeicacid[ 6] (2) Yelowpowder(MeOH);ESI-MSm/z179[M-H] -;1HNMR(CD3OD, 400MHz)δ:7.05 (1H, d, J=2.0 Hz, H-2), 6.79(1H, d, J=8.2Hz, H-5), 6.95 (1H, dd, J=
8.2, 2.0Hz, H-6), 7.52 (1H, d, J=15.9 Hz,H-7), 6.23 (1H, d, J = 15.9 Hz, H-8);
13CNMR(CD3 OD, 100 MHz)δ:127.7 (C-1),
116.6 (C-2), 146.7 (C-3), 149.4 (C-4), 115.8(C-5), 115.2 (C-6), 146.8(C-7), 122.8 (C-8),
170.9 (C-9).
Pluchoicacid[ 7](3) Colorlesspowder(MeOH);
1HNMR(CD3OD, 400 MHz)δ:6.68 (1H, d, J=2.1 Hz, H-3), 6.19(1H, d, J=9.4 Hz, H-
5), 7.81 (1H, d, J=9.4 Hz, H-6), 3.88 (3H,s, -OMe).Protocatechualdehyde[ 8] (4) Colorlessneedles
(Me2 CO);1HNMR(Acetone-d6 , 400 MHz)δ:
7.33 (1H, d, J=1.9 Hz, H-2), 6.99(1H, d, J=7.9 Hz, H-5), 7.35 (1H, dd, J= 7.2, 1.9Hz, H-6), 9.77 (1H, s, H-7), 8.77 (2H, brs,
3, 4-OH);13CNMR(Acetone-d6 , 100 MHz).δ:
130.9 (C-1), 115.1 (C-2), 146.4 (C-3), 152.3(C-4), 116.1(C-5), 125.5 (C-6), 191.2 (C-7).
Vanilin[ 9] (5) Colorles plate crystal
(CHCl3);1HNMR(CDCl3 , 400 MHz)δ:6.37(1H, d, J=1.6 Hz, H-2), 7.06 (1H, d, J=
8.5 Hz, H-5), 7.44(1H, dd, J=8.0, 1.6 Hz,H-6), 9.84 (1H, s, H-7), 3.98 (3H, s, -
OMe);13CNMR(CDCl3 , 100 MHz)δ:130.0 (C-
1), 108.7 (C-2), 147.1 (C-3), 151.7 (C-4),
114.4 (C-5), 127.6(C-6), 191.0 (C-7), 56.1(-OMe).
Hydroxytyrosol[ 10] (6) Brownoil(MeOH);
1HNMR(CD3OD, 500 MHz)δ:6.64 (1H, d, J=1.8 Hz, H-2), 6.66(1H, d, J=8.0 Hz, H-
118 ChinJNatMed Mar.2008 Vol.6 No.2 2008年 3月 第 6卷 第 2期
5), 6.52(1H, dd, J=8.0, 2.0Hz, H-6), 2.65(2H, t, J=7.3 Hz, H-7), 3.66 (2H, t, J=
7.3Hz, H-8);13CNMR(CD3 OD, 125 MHz).δ:
131.8 (C-1), 116.3 (C-2), 146.1 (C-3), 144.6(C-4), 117.1 (C-5), 121.2 (C-6), 39.6 (C-7),
64.6(C-8).
4-Carbonyl-5-hydroxymethylvalerate[ 11] (7) Yelowoil(CHCl3);1HNMR(CDCl3 , 500 MHz)δ:2.67 (2H, t, J=6.7, H-2), 2.73(2H, t, J=6.7, H-3), 4.33 (2H, s, H-5), 3.69 (3H, s,
-OMe);13CNMR(CDCl3 , 125 MHz)δ:172.7 (C-
1), 27.4(C-2), 32.7 (C-3), 208.1 (C-4), 68.1(C-5), 51.9 (-OMe).
4-Hydroxydodec-2-enedioicacid[ 12] (8) White
amorphoussolid(MeOH);1 HNMR(CD3 OD, 400MHz)δ:5.96 (1H, dd, J=15.6, 1.6 Hz, H-
2), 6.91 (1H, dd, J= 15.6, 5.0 Hz, H-3),
4.21 (1H, m, H-4), 1.61-1.50 (4H, m, H-5,
10), 1.45-1.34(8H, m, H-6 , 7, 8, 9), 2.27(2H,
t, J= 7.4 Hz, H-11);13CNMR(CD3 OD, 100MHz)δ:170.1 (C-1), 120.9 (C-2), 152.7 (C-
3), 71.5 (C-4), 37.5 (C-5), 26.4 (C-6), 30.4(C-7), 30.3 (C-8), 30.1 (C-9), 26.0 (C-10),
34.9(C-11), 177.7(C-12).
(+)-VladinolF[13](9) Colorlessoil(MeOH);
[ α] 25D:+1.63°(c2, MeOH);ESI-MSm/z383[M+Na] + , 743 [ 2M +Na] +;1HNMR(CD3 OD,
400MHz)δ:6.94(1H, brs, H-2), 6.75(1H, d,J=8.0Hz, H-5), 6.81 (1H, brd, J=6.8Hz,H-6), 5.48 (1H, d, J= 6.3 Hz, H-7), 3.46(1H, dd, J= 12.4, 6.2 Hz, H-8), 3.81-3.72(2H, m, H-9), 6.71 (2H, brs, H-2′, 6′), 2.61(2H, t, J=7.6 Hz, H-7′), 1.80 (2H, dt, J=
15.0, 6.6 Hz, H-8′), 3.55 (2H, t, J=6.4 Hz,H-9′), 3.83 (6H, s, -OMe);13CNMR(CD3 OD,
100MHz)δ:132.5 (C-1), 109.8 (C-2), 149.0(C-3), 147.5 (C-4), 115.5 (C-5), 119.4(C-6),
87.0(C-7), 55.9 (C-8), 68.2 (C-9), 128.9 (C-
1′), 114.6 (C-2′), 143.8 (C-3′), 145.1 (C-4′),
137.9 (C-5′), 114.8 (C-6′), 34.9 (C-7′), 30.9(C-8′), 68.2 (C-9′), 55.9 (-OMe), 55.9 (-OMe).
(-)-Syringaresinol[ 14] (10) Colorlessoil
(CHCl3);[ α] 25D:-8.75°(c2, CHCl3);1HNMR(CDCl3 , 400 MHz)δ:6.58 (4H, brs, H-2, 2′,
6, 6′), 5.55(2H, brs, 4, 4′-OH), 4.74(2H, d,J=3.6 Hz, H-7, 7′), 3.10(2H, m, H-8, 8′),
3.92(2H, m, H-9α, 9′α), 4.29 (2H, m, H-9β,
9′β), 3.90 (12H, s, OCH3);13CNMR(CDCl3 ,
100MHz)δ:132.0 (C-1 , 1′), 102.6 (C-2 , 2′, 6,
6′), 147.1 (C-3, 3′, 5, 5′), 134.2 (C-4, 4′), 86.1(C-7, 7′), 54.3(C-8 , 8′), 71.8 (C-9, 9′), 56.3(-OMe).
(+)-Guayarol[ 15, 16] (11) Colorlesoil(CHCl3);[ α] 25D:+15.83°(c2, CHCl3);ESI-MSm/z359
[M +H] + , 381[ M +Na] +;1HNMR(CDCl3 ,
500MHz)δ:6.59 (1H, d, J=1.6 Hz, H-2),
6.80 (1H, d, J=8.1 Hz, H-5), 6.61 (1H, dd,J=8.1, 1.6 Hz, H-6), 2.91 (2H, m, H-7),
6.41 (1H, d, J=1.6 Hz, H-2′), 6.82 (1H, d,J=8.3Hz, H-5′), 6.50(1H, dd, J=8.0, 1.6Hz, H-6′), 2.60-2.46 (4H, m, H-7′, 8′, 8),
3.89 (1H, dd, J=9.1, 7.4 Hz, H-9′α), 4.15(1H, dd, J=9.1, 7.4 Hz, H-9′β), 3.81 (6H,
s, -OMe), 5.57 (2H, brs, 3′, 4′-OH);13CNMR(CDCl3 , 125MHz)δ:129.5(C-1), 111.5(C-2),
146.7 (C-3), 146.6 (C-4), 111.0 (C-5), 121.3(C-6), 34.6 (C-7), 46.6 (C-8), 178.8 (C-9),
129.8 (C-1′), 114.4 (C-2′), 144.5 (C-3′),
144.4 (C-4′), 114.1 (C-5′), 122.1 (C-6′), 38.3(C-7′), 41.0(C-8′), 71.3(C-9′), 55.8(-OMe).(-)-Arctin[ 17] (12) Colorlessoil(Me2CO);[α] 25D:-7.13°(c2, Me2CO);1HNMR(Acetone-d6 , 400 MHz)δ:6.84 (1H, d, J=1.7 Hz, H-
2), 7.07 (1H, d, J=8.2 Hz, H-5), 6.70 (1H,dd, J=7.9, 1.6 Hz, H-6), 6.67 (1H, d, J=
1.5 Hz, H-2′), 6.73 (1H, d, J= 8.0 Hz, H-
5′), 6.56 (1H, dd, J= 8.0, 1.7 Hz, H-6′),
4.88 (1H, d, J=7.3 Hz, Glc-H-1), 3.84 (3H,s, -OMe), 3.85 (3H, s, -OMe), 3.90 (3H, s, -OMe);13CNMR(Acetone-d6 , 100 MHz)δ:130.9(C-1), 115.7(C-2), 148.3 (C-3), 146.0 (C-4),
114.6 (C-5), 122.5(C-6), 35.0 (C-7), 46.9 (C-
8), 179.0 (C-9), 133.8 (C-1′), 117.4 (C-2′),
150.4 (C-3′), 146.7 (C-4′), 113.0 (C-5′),
121.9 (C-6′), 38.4 (C-7′), 42.2 (C-8′), 71.6(C-9′), 102.6(C-1″), 74.7(C-2″), 77.7 (C-3″),
71.2 (C-4″), 77.8 (C-5″), 62.6 (C-6″), 56.3 (-OMe).
(-)-Lariciresinol[ 18] (13) Colorlessoil
(CHCl3);[ α] 25D:-10.00°(c1, CHCl3);1HNMR(CDCl3 , 400MHz)δ:6.70(1H, d, J=1.9Hz,H-2), 6.81 (1H, d, J= 8.1 Hz, H-5), 6.67(1H, dd, J=8.1, 1.9Hz, H-6), 2.55(1H, dd,J=13.7, 10.7Hz, H-7α), 2.91 (1H, dd, J=
13.7, 4.7 Hz, H-7β), 2.7(1H, m, H-8), 6.88(1H, d, J=1.9 Hz, H-2′), 6.84 (1H, d, J=
8.1Hz, H-5′), 6.79 (1H, dd, J=8.1, 1.9Hz,H-6′), 4.79 (1H, d, J= 6.6 Hz, H-7′), 2.40(1H, dd, J=13.8, 6.9 Hz, H-8′), 3.76 (1H,dd, J=10.7, 6.8Hz, H-9′a), 3.91(1H, dd, J= 10.7, 7.1 Hz, H-9′b), 3.87 (6H, brs,
OCH3);13CNMR(CDCl3 , 100MHz)δ:132.3 (C-
1), 111.2 (C-2), 146.6 (C-3), 144.0 (C-4),
114.4 (C-5), 121.2(C-6), 33.3 (C-7), 42.4 (C-
8), 72.1 (C-9), 134.8 (C-1′), 108.3 (C-2′),
146.6 (C-3′), 145.0 (C-4′), 114.2 (C-5′),
118.7 (C-6′), 82.8 (C-7′), 52.6 (C-8′), 60.9(C-9′), 55.9 (-OMe).
Hyperin[ 19] (14) Yelowneedles(MeOH);ESI-MSm/z487[ M +Na] +, 951[ 2M +Na] +;
2008年 3月 第 6卷 第 2期 ChinJNatMed Mar.2008 Vol.6 No.2 119
1HNMR(DMSO-d6 , 400MHz)δ:6.18(1H, d, J=1.8Hz, H-6), 6.39 (1H, d, J=1.8 Hz, H-
8), 7.51(1H, d, J=2.0Hz, H-2′), 6.80(1H,d, J=8.4 Hz, H-5′), 7.66 (1H, dd, J=8.4,
1.9Hz, H-6′), 12.62(1H, s, OH-5), 5.37(1H,d, J= 7.7 Hz, Gal- H-1)3.64-3.29 (6H, m,
protonsofgalactosyl);13 CNMR (DMSO-d6 , 100MHz)δ:156.2 (C-2), 133.5 (C-3), 177.5 (C-
4), 161.2(C-5), 98.7(C-6), 164.3(C-7), 93.5(C-8), 156.2 (C-9), 103.9 (C-10), 121.1 (C-
1′), 115.2 (C-2′), 144.8 (C-3′), 148.5 (C-4′),
116.0 (C-5′), 122.0 (C-6′), 101.8 (C-1″), 71.2(C-2″), 73.2 (C-3″), 67.9 (C-4″), 75.8 (C-5″),
60.1(C-6″).Acknowledgements:WearegratefultotheAna-lyticalGroup, LaboratoryofPhytochemistry, Kun-mingInstituteofBotany, ChineseAcademyofSci-encesforthespectralmeasurements.
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绣球藤的化学成分
宋成芝 1, 2 ,王跃虎 2 ,华 燕1 ,吴章康 1 ,杜芝芝2*
1西南林学院资源学院 , 昆明 650224;
2中国科学院昆明植物研究所 , 昆明 650204
【摘 要】 目的:对绣球藤的化学成分进行研究。方法:利用硅胶柱色谱 、SephadexLH-20等方法进行分离纯化。根
据理化性质和光谱分析进行结构鉴定。结果:从绣球藤乙醇提取物的乙酸乙酯部分中分离得到 14个化合物 , 分别鉴定
为:松柏醛(1),咖啡酸(2), pluchoicacid(3), 原儿茶醛(4), 香草醛(5), 3, 4-二羟基苯乙醇(6), 4-羰基-5-羟基戊酸甲酯
(7), 4-hydroxydodec-2-enedioicacid(8), (+)-川木香醇 F(9), (-)-丁香脂素(10), (+)-guayarol(11), (-)-牛蒡苷
(12), (-)-落叶松树脂醇(13), 金丝桃苷(14)。结论:这些化合物均为首次从该植物中分离得到。
【关键词】 绣球藤;铁线莲属;木脂素;黄酮
【基金项目】 中科院 “西部之光”资助项目和国家自然科学基金资助项目(No.30400038)