全 文 ：天然产物研究与开发 NatProdResDev2008, 20:816-820, 845
文章编号:1001-6880(2008)05-0816-06
　
　
　ReceivedJuly2, 2007;AcceptedSeptember11, 2007
　FoundationItem:ThisstudywassupportedbytheMinistryofScience＆
TechnologyofChina(2005DKA21006), theCentralUniversityforNa-
tionalities(985-3-3-1)andtheYoungScholarsFoundationofYunnan
AgricultureUniversity(2006Q22).
＊CorrespondingauthorTel:86-871-5223233;E-mail:long@mail.kib.
ac.cn
中华山蓼化学成分研究
李兴玉 1, 2 ,龙春林 1, 3＊ ,王跃虎 1 ,郭　蓉 1, 4
1中国科学院昆明植物研究所 ,昆明 650204;2云南农业大学基础与信息工程学院 ,昆明 650201;
3中央民族大学生命与环境科学学院 , 北京 100081;4云南农业大学农学与生物技术学院 ,昆明 650201
摘　要:从中华山蓼(OxyriasinensisHemsl.)全草中首次分离得到十四个化合物 , 通过波谱学方法分别鉴定为
(-)-表没食子儿茶素(1)、(-)-儿茶素没食子酸酯(2)、(-)-表儿茶素(3)、(-)-表儿茶素-3-没食子酸酯(4)、槲皮
素-3-O-α-L-鼠李糖苷(5)、tiliroside(6)、山萘酚-3-O-β-D-吡喃葡萄糖苷(7)、桷皮素(8)、2, 4-二羟基-6-甲氧基-乙
酰基苯-4-O-β-D-吡喃葡萄糖苷(9)、反-N-(4-羟基苯乙基)阿魏酸酰胺(10)、顺-N-(4-羟基苯乙基)阿魏酸酰胺
(11)、icariolA
2
(12)、(+)-松脂素(13)、HeloniosideB(14)。
关键词:中华山蓼;山蓼属;黄酮;木脂素
中图分类号:R284.2;Q946.91 文献标识码:A
ChemicalConstituentsofOxyriadigyna
LIXing-yu1, 2 , LONGChun-lin1, 3＊ , WANGYue-hu1 , GUORong1, 4
1KunmingInstituteofBotany, ChineseAcademyofSciences, Kunming650204 , China;
2CollegeofScienceandInformationEngineering, YunnanAgriculturalUniversity, Kunming650201 , China;
3ColegeofLifeandEnvironmentSciences, ChinaNationalityUniversity, Beijing100081 , China;
4SchoolofAgronomyandBiotechnology, YunnanAgriculturalUniversity, Kunming650201 , China
Abstract:FourteencompoundswereisolatedfromOxyriasinensisHemsl.forthefirsttime.Bythespectroscopicanaly-
sis, theywereidentifiedas(-)-epigallocatechin(1), (-)-epigallocatechin-3-galate(2), (-)-epicatechin(3), (-)-epi-
catechin-3-galate(4), quercetin-3-O-α-L-rhamnoside(5), tiliroside(6), kaempferol-3-O-β-D-glucopyranoside(7),
querctine(8), annphenone(9), cis-N-(p-hydroxyphenethyl)ferulamide(10), trans-N-(p-hydroxyphenethyl)ferulamide
(11), icariolA2(12), (+)-lyoniresinol(13), andheloniosideB(14).
Keywords:Oxyriadigyna;OxyriaHill;flavonoids;lignans
Introduction
ThegenusOxyriaHil(Polygonaneae)containingtwo
speciesisdistributedinAsia, Europe, NorthAmerica.
OxyriasinensisHemsl., aperennialherb, isanendemic
speciestoChina.Itusualygrowsinmountainslopes,
valeys, grasslands, anddistributinginGuizhou, Si-
chuan, Tibet, andYunnan[ 1] .Asafolkmedicinalherb,
thewholeplantshavebeenusedforthetreatmentof
noxiousheat, paininlegandtraumaticinjury[ 2] , diar-
rhea[ 3] .ThechemicalconstituentsofO.sinensishave
notbeenreportedsofar.Wehavecarriedoutadetailed
chemicalinvestigationonthisplantandisolated14
knowncompoundsfromitsethylacetateextracts.These
compoundswereelucidatedtobe(-)-epigalocatechin
(1), (-)-epigalocatechin-3-galate(2), (-)-epicate-
chin(3), (-)-epicatechin-3-galate(4), quercetin-3-O-
α-L-rhamnoside(5), tiliroside(6), kaempferol-3-O-β-
D-glucopyranoside(7), querctine(8), annphenone
(9), trans-N-(p-hydroxyphenethyl)ferulamide(10),
cis-N-(p-hydroxyphenethyl)ferulamide(11), icariolA2
(12), (+)-lyoniresinol(13), andheloniosideB
(14).
ExperimentalSection
General
Thinlayerchromatographywasconductedonsilicagel
DOI :10.16333/j.1001-6880.2008.05.024
F254 plates(QingdaoMeigaoChemicalCo.Ltd.).The
compoundsonTLCplateswerevisualizedwith5%sul-
phuricacidinethanolandheatingonahotplate.
HPLCseparationswereperformedonanAgilentTech-
nologies1200Seriesinstrument, andanalyticalcolumns
conductedwereSB-C18 9.4 ×250.Opticalrotations
weredeterminedonaJASCODIP370 digitalPolarime-
ter.Columchromatography(CC)wascarriedoutonsili-
cagel(200-300 mesh;QingdaoMakalGroupCo.
LTD), SephhadexLH-20(GEHealthcareBio-Sciences
AB), C-18 silicagel(40-75 μm, FujiSilysiaChemical
LTD), polyamide(100-200mesh, TaizhouLuqiaoSi-jia
BiochemicalPlasticCompany), andMCIresin(75-150
μm, MitsubishiChemicalCorporation).Preparative
TLCwascarriedoutonsilicagelF254(QingdaoMeigao
ChemicalCo.Ltd.).MSweremeasuredonaVGAuto-
Spec3000 massspectrometer.AltheNMRdatawere
obtainedatroomtemperatureonAM-400andDRX-500
spectrometer(TMSasinternalreference, chemicalshift
inδ, ppm).
Plantmaterial
ThewholeplantsofO.sinensiswerecolectedinDong-
chuanofYunnanProvinceofChinainNovember,
2006, andidentifiedbyProf.LongChun-linattheKun-
mingInstituteofBotany, theChineseAcademyofSci-
ences.Avoucherspecimen(NO.06L072)wasdeposi-
tedintheHerbarium, KunmingInstituteofBotany,
ChineseAcademyofSciences(KUN).
Extractionandisolation
Theair-driedandpowderedwholeplantsofO.sinensis
(5kg)wereextractedwith95% EtOH(30 L×3).
Afterconcentratingunderreducedpresureat60 ℃, a
residue(1.1 kg)wasobtained.Theresiduewasdis-
solvedincoldwaterandextractedwithpetroleumether
(2 L×7), EtOAc(1 L×8)andn-BuOH(1 L×
8).TheEtOAcfraction(70 g)wassubjectedtosilica
gelcolumnelutedwithCHCl3-MeOH(30∶1 to0∶1)to
givefractionsE1-E6.Thefr.E3(25g)wasdividedinto
sevenfractions(E31 toE37)byCCwithpetroleume-
ther-EtOAc(1∶1to0∶1).Thefr.E32wasfurthersepa-
ratedoverC-18 silicagelcolumnelutedwith50% to
100% H2O-MeOHtogive1(31.2 mg), 2(382.5
mg), 3(243.4 mg)and4(418.9 mg).Thefr.E34
(5.0 g)wasfurtherseparatedoverpolyamidecolumn
elutedwithH2O-MeOH(0to100%)togive5(1.3 g)
and6(10.0 mg).Compounds7(10.0 mg)and8
(13.5 mg)wereisolatedfromfr.E36(1.4g)bySeph-
adexLH-20 CC.Thefr.E2(5.3 g)wasdividedinto
nineportions(E21-E29)byMCICCelutedwithH2O-
MeOH(0% to100%).Thefr.E27(1.6 g)wasfur-
therseparatedoversilicagelelutedwithCHCl3 -MeOH
(4∶1)togivesevenportions(E271-E277).Thefr.
E274(290.6 mg)wasseparatedonSephadexLH-20
CCelutedwithMeOHtoyield9(16.7 mg).Thefr.
E272(306.5 mg)wassubjectedtoSephadexLH-20
CCelutedwithMeOHtoprovide11(6.1 mg), 12
(16.2 mg).Thefr.E273 wassubjectedtosemi-pre-
parativeHPLC(SB-C18 , 9.4 ×250mm, 30 μL, 2mL/
min, 55% MeOH)toyield10(2.1 mg, 7.5-8.3 min)
and12(2.1 mg, 8.6-9.4 min).Thefr.E275(259.3
mg)wasseparatedonsemi-preparativeHPLC(SB-C18 ,
9.4 × 250mm, 20 μL, 2 mL/min, 55% MeOH)to
yield14(6.0 mg, 13.4-14.5 min)and13(3.2 mg,
7.5-8.2 min).
ResultsandDiscussion
(-)-Epigalocatechin(1)　Whiteamorphoussolid
(MeOH);[ α] 21D -18.52°(c0.14, MeOH);1HNMR
(CD3OD, 400 MHz)δ:4.75(1H, s, H-2), 4.17(1H,
m, H-3), 2.85(2H, dd, J=18.4, 4.4 Hz, H-4), 5.96
(1H, d, J=2.4Hz, H-6), 5.87(1H, d, J=2.4Hz, H-
8), 6.52(1H, s, H-2′), 6.52(1H, s, H-6′);13CNMR
(CD3OD, 100MHz)δ:79.8(C-2), 67.5(C-3), 29.1
(C-4), 157.3(C-5), 96.3(C-6), 157.9(C-7), 95.9
(C-8), 158.0(C-9), 100.1(C-10), 131.5(C-1′),
107.0(C-2′, C-6′), 146.6(C-3′, C-5′), 133.5(C-
4′).ItsNMRspectraldatawereinconsistentwith
thosereported[ 4, 5] .
(-)-Epigalocatechin-3-galate(2)　Pinkamorphous
powder(MeOH);[ α] 21D -132.7°(c1.42, MeOH);1H
NMR(CD3OD, 400 MHz)δ:4.97(1H, brs, H-2),
5.53(1H, brd, J=1.6 Hz, H-3), 2.98(1H, dd, J=
4.5, 21.7Hz, H-4a), 2.84(1H, dd, J=21.7, 2.4Hz,
H-4b), 5.95(1H, brs, H-6), 5.95(1H, brs, H-6),
6.50(2H, s, H-2′, H-6′), 6.94(2H, s, H-2″, H-6″);
13CNMR(CD3OD, 100 MHz)δ:78.6(C-2), 69.9(C-
817Vol.20 　　　　　　LIXing-yu, etal:ChemicalConstituentsofOxyriadigyna　
3), 26.8(C-4), 157.2(C-5), 96.5(C-6), 157.9(C-
7), 95.9(C-8), 157.9(C-9), 99.4(C-10), 130.8(C-
1′), 106.9(C-2′, C-6′), 146.7(C-3′, C-5′), 133.8
(C-4′), 121.5(C-1″), 110.3(C-2″, C-6″), 146.3(C-
3″, C-5″), 139.8(C-4″), 167.7(C-7″).ItsNMRspec-
traldatawereidenticalwiththosereported[ 5] .
(-)-Epicatechin(3)　 White amorphous solid
(MeOH);[ α] 21D -55.39°(c0.31, MeOH);1HNMR
(CD3OD, 400 MHz)δ:4.81(1H, s, H-2), 4.17(1H,
brs, H-3), 2.86(1H, dd, J=4.6, 21.3 Hz, H-4a),
2.74(1H, dd, J=21.3, 2.7 Hz, H-4b), 5.92(1H, d, J
=2.1 Hz, H-6), 5.95(1H, d, J=2.1 Hz, H-8), 6.98
(1H, d, J=1.6 Hz, H-2′), 6.77(1H, d, J=8.1 Hz,
H-5′), 6.78(1H, dd, J=8.1, 1.6 Hz, H-6′);13C
NMR(CD3OD, 100 MHz)δ:79.8(C-2), 67.4(C-3),
29.2(C-4), 157.3(C-5), 96.4(C-6), 158.0(C-7),
95.9(C-8), 157.6(C-9), 100.0(C-10), 132.2(C-
1′), 115.3 (C-2′), 145.9(C-3′), 145.7 (C-4′),
115.9(C-5′), 119.4(C-6′).ItsNMRspectraldata
wereidenticaltothosereported[ 5] .
(-)-Epicatechin-3-galate(4)　 Brownamorphous
solid(MeOH);[ α] 21D-145.43°(c0.12, MeOH);1H
NMR(CD3OD, 400 MHz)δ:5.02(1H, s, H-2), 5.52
(1H, brd, J=2.4 Hz, H-3), 2.86(1H, dd, J=19.5,
2.1Hz, H-4a), 3.00(1H, dd, J=19.5, 4.6 Hz, H-
4b), 5.96(1H, d, J=2.4 Hz, H-6), 5.96(1H, d, J=
2.4Hz, H-8), 6.96(1H, d, J=5.6 Hz, H-2′), 6.70
(1H, d, J=8.0Hz, H-5′), 6.81(1H, dd, J=8.4, 2.0
Hz, H-6′), 6.94 (2H, s, H-2″, H-6″);13 C NMR
(CD3OD, 100 MHz)δ:78.6(C-2), 69.9(C-3), 26.8
(C-4), 157.8(C-5), 96.5(C-6), 157.8(C-7), 95.8
(C-8), 157.2(C-9), 99.3(C-10), 131.4(C-1′),
116.0(C-2′), 145.9(C-3′), 145.9(C-4′), 115.1(C-
5′), 119.3(C-6′), 121.4(C-1″), 110.2(C-2″, C-6″),
146.3(C-3″, C-5″), 139.7(C-4″), 167.6(C-7″).Its
NMRspectraldatawereidenticaltothosereported[ 5] .
Quercetin-3-O-α-L-rhamnoside(5)　Yelowamor-
phouspowder(MeOH);1H NMR(DMSO-d6 , 400
MHz)δ:6.20(1H, d, J=1.96 Hz, H-6), 6.38(1H, d,
J=1.96 Hz, H-8), 7.29(1H, d, J=2.0 Hz, H-2′),
6.86(1H, d, J=8.32 Hz, H-5′), 7.24(1H, dd, J=
8.32, 2.0 Hz, H-6′), 5.25(1H, s, H-1″), 3.32-3.52
(1H, m, H-2″), 3.09-3.23(1H, m, H-3″), 3.09-3.23
(1H, m, H-4″), 3.32-3.52(1H, m, H-5″), 0.81(3H,
d, J=5.9 Hz, H-6″);13CNMR(DMSO-d6 , 100 MHz)
δ:156.5(C-2), 134.3(C-3), 177.8(C-4), 161.4(C-
5), 98.8(C-6), 164.2(C-7), 93.7(C-8), 157.4(C-
9), 104.2(C-10), 121.2(C-1′), 115.5(C-2′), 145.3
(C-3′), 148.5(C-4′), 115.7(C-5′), 120.8(C-6′),
101.9(C-1″), 70.4(C-2″), 70.7(C-3″), 71.3(C-
4″), 70.1(C-5″), 17.6(C-6″).ItsNMRspectraldata
wereinaccordancewiththosereported[ 6] .
Tiliroside(6)　Yelowamorphouspowder(MeOH);
1HNMR(CD3OD, 400 MHz)δ:6.12(1H, d, J=1.8
Hz, H-6), 6.30(1H, d, J=1.8 Hz, H-8), 7.96-7.99
(2H, m, H-2′, H-6′), 6.77-6.82(2H, m, H-3′, H-
5′), 5.24(1H, d, J=7.6 Hz, H-1″), 4.19-4.28(2H,
m, H-6″), 7.96-7.99(2H, m, H-2 , H-6 ), 6.77-6.82
(2H, m, H-3 , H-5 ), 7.38(1H, d, J=15.9 Hz, H-
7 ), 6.06(1H, d, J=15.9 Hz, H-8 );13 CNMR
(CD3OD, 100 MHz)δ:159.3(C-2), 135.2(C-3),
179.4(C-4), 163.0(C-5), 100.0(C-6), 165.9(C-
7), 94.8(C-8), 158.4(C-9), 105.6(C-10), 122.7
(C-1′), 131.2(C-2′, C-6′), 116.0(C-3′, C-5′),
161.2(C-4′), 103.9(C-1″), 75.7(C-2″), 78.0(C-
3″), 71.7(C-4″), 75.8(C-5″), 64.3(C-6″), 127.1
(C-1 ), 132.3(C-2 , C-6 ), 116.8(C-3 , C-5 ),
161.5(C-4 ), 146.5(C-7 ), 114.7(C-8 ), 168.8
(C-9 ).ItsNMRspectraldatawereinagreementwith
thosereported[ 7] .
Kaempferol-3-O-β -D-glucopyranoside(7)　Color-
lessamorphoussolid(MeOH);1HNMR(CD3OD, 400
MHz)δ:6.18(1H, d, J=2.0 Hz, H-6), 6.37(1H, d, J
=2.0 Hz, H-8), 8.04(2H, d, J=8.8 Hz, H-2′, H-
6′), 6.87(2H, d, J=8.8 Hz, H-3′, H-5′), 5.24(1H,
d, J=7.2 Hz, H-1″), 3.53-3.55(1H, m, H-2″), 3.41-
3.44(1H, m, H-3″), 3.41-3.44(1H, m, H-4″), 3.53-
3.55(1H, m, H-5″), 3.67-3.70(2H, dd, H-6″);13C
NMR(CD3OD, 100 MHz)δ:158.5(C-2), 135.4(C-
3), 179.5(C-4), 163.0(C-5), 99.9(C-6), 166.0(C-
7), 94.8(C-8), 161.5(C-9), 105.7(C-10), 122.8
(C-1′), 132.3(C-2′, C-6′), 116.1(C-3′, C-5′),
159.0(C-4′), 104.1(C-1″), 75.7(C-2″), 78.0(C-
3″), 71.3(C-4″), 78.4(C-5″), 62.6(C-6″).ItsNMR
spectraldatawereconsistentwiththosereported[ 8] .
Querctine(8)　Yelowamorphouspowder(MeOH);
818 NatProdResDev　　　　　　　　　　　　　　　　　　　　 　Vol.20
1HNMR(CD3OD, 400 MHz)δ:6.16(1H, d, J=2.0
Hz, H-6), 6.36(1H, d, J=2.0 Hz, H-8), 6.87(1H,
d, J=8.4Hz, H-2′), 7.72(1H, d, J=2.0 Hz, H-5′),
7.62(1H, dd, J=2.0 , 8.4 Hz, H-6′);13 CNMR
(CD3OD, 100 MHz)δ:147.8(C-2), 137.2(C-3),
177.2(C-4), 162.4(C-5), 99.4(C-6), 166.0(C-7),
94.6(C-8), 158.2(C-9), 104.4(C-10), 124.1(C-
1′), 116.0 (C-2′), 146.2(C-3′), 148.8 (C-4′),
116.3(C-5′), 121.6(C-6′).TheNMRspectraldata
wereconsistentwiththosereported[ 9] .
Annphenone(9)　 Yelow amorphous powder
(MeOH);1HNMR(CD3OD, 400 MHz)δ:6.18(1H,
d, J=2.0 Hz, H-3), 6.30(1H, d, J=2.0 Hz, H-5),
2.6(3H, s, H-8), 3.91(3H, s, H-9), 4.98(1H, d, J=
7.2Hz, H-1′), 3.29-3.48(1H, m, H-2′), 3.44-3.48
(1H, m, H-3′), 3.44-3.48(1H, m, H-3′), 3.29-3.48
(1H, m, H-5′), 3.68-3.70(2H, dd, H-6′);13CNMR
(CD3OD, 100 MHz)δ:107.5(C-1), 165.5(C-2),
164.7(C-6), 97.8(C-3), 92.9(C-5), 167.7(C-4),
204.9(C-7), 33.3(C-8), 56.3(C-9), 101.4(C-1′),
74.7(C-2′), 77.9(C-3′), 71.3(C-4′), 78.4(C-5′),
62.5(C-6′).ItsNMRspectraldatawereinagreement
withthosereported[ 10] .
trans-N-(p-Hydroxyphenethyl)ferulamide(10)　
Colorlessamorphoussolid(MeOH);1HNMR(CD3OD,
400MHz)δ:6.38(1H, d, J=16.0 Hz, H-2), 7.43
(1H, d, J=16.0 Hz, H-3), 7.09(1H, brd, H-5),
6.77(1H, d, J=8.4 Hz, H-8), 7.03(1H, H-9), 3.85
(3H, s, H-10), 3.45(2H, t, J=7.5 Hz, H-1′), 2.74
(2H, t, J=7.5 Hz, H-2′), 7.05(2H, H-4′, H-8′),
6.70(2H, H-5′, H-7′);13CNMR(CD3OD, 100 MHz)
δ:169.2(C-1), 118.4(C-2), 142.1(C-3), 127.9(C-
4), 111.4(C-5), 149.4(C-6), 150.4(C-7), 116.6
(C-8), 123.3(C-9), 56.3(C-10), 42.5(C-1′), 35.8
(C-2′), 131.3(C-3′), 130.7(C-4′, C-8′), 116.3(C-
5′, C-7′), 156.9(C-6′).TheNNRspectraldatawere
inconsistentwiththosereported[ 11] .
cis-N-(p-Hydroxyphenethyl)ferulamide(11)　Col-
orlesamorphoussolid(MeOH);1HNMR(CD3OD,
400MHz)δ:5.80(1H, d, J=10.0 Hz, H-2), 6.59
(1H, d, J=10.0 Hz, H-3), 7.33(1H, brs, H-5),
6.99(1H, dd, J=6.8, 2.4 Hz, H-8), 6.70(1H, dd, J
=6.8, 2.4 Hz, H-9), 3.81(3H, brd, H-10), 3.38
(2H, t, J=8.0 Hz, H-1′), 2.68(2H, t, J=8.0 Hz, H-
2′), 6.79(1H, brs, H-4′, H-8′), 6.91(1H, m, H-5′,
H-7′);13CNMR(CD3OD, 100 MHz)δ:170.3(C-1),
121.6(C-2), 138.4(C-3), 128.5(C-4), 113.9(C-
5), 148.5(C-6), 148.6(C-7), 115.8(C-8), 124.8
(C-9), 56.3(C-10), 42.4(C-1′), 35.6 (C-2′),
131.2(C-3′), 130.7(C-4′, C-8′), 116.2(C-5′, C-
7′), 156.9(C-6′).TheNMRspectraldatawereinac-
cordancewiththosereported[ 10] .
IcariolA2 (12)　 Colorles amorphouspowder
(MeOH);1HNMR(CD3OD, 400 MHz)δ:6.73(4H,
s, H-2 , H-2′, H-6, H-6′), 4.95(2H, d, J=8.4 Hz, H-
7, H-7′), 2.95(2H, m, H-8, H-8′), 4.85(4H, m, H-
9, H-9′), 3.86(12H, s, OMe);13CNMR(CD3OD, 100
MHz)δ:134.2(C-1 , C-1′), 104.8(C-2 , C-2′, C-6, C-
6′), 149.3(C-3, C-3′, C-5 , C-5′), 136.2(C-4, C-4′),
84.6(C-7, C-7′), 55.2(C-8, C-8′), 61.6(C-9, C-
9′), 56.8(OMe).TheNMRspectraldatawereidenti-
caltothosereported[ 12] .
(+)-Lyoniresinol(13)　 Whiteamorphoussolid
(MeOH);[ α] 21D +12.50°(c0.024, MeOH);1HNMR
(DMSO-d6 , 400 MHz)δ:6.58(1H, s, H-2), 2.70
(1H, dd, J=4.0 , 16.0 Hz, H-7a), 2.58(1H, t, J=
9.2 Hz, H-7b), 1.63(1H, m, H-8), 1.96(1H, dd, J=
4.4, 10.8 Hz, H-8′), 6.38(2H, d, J=6.0 Hz, H-2′,
H-6′), 4.31(1H, d, J=4.4 Hz, H-7′), 3.47-3.60
(4H, m, H-9, H-9′), 3.23-3.85(12H, m, H-3′, 5′, 5,
3OMe);13CNMR(DMSO-d6 , 100 MHz)δ:130.2(C-
1), 107.8(C-2), 148.7(C-3), 138.9(C-4), 147.7
(C-5), 126.3(C-6), 3.6(C-7), 40.9(C-8), 66.8(C-
9), 139.3(C-1′), 106.9(C-2′, C-6′), 149.0(C-3′, C-
5′), 134.5(C-4′), 42.3(C-7′), 48.8(C-8′), 64.2
(C-9′), 56.8(C-3′OMe, C-5′OMe), 60.2(C-5OMe),
56.6(C-3OMe).ItsNMRspectraldatawereidentical
tothosereported[ 13] .
HeloniosideB(14)　 Colorlessamorphoussolid
(MeOH);1HNMR(CD3OD, 400 MHz)δ:5.48(1H,
d, J=4.0 Hz, H-1′), 3.41(1H, dd, J=10.0, 4.0
Hz, H-2′), 4.47(1H, m, H-3′), 3.24(1H, t, J=8.0
Hz, H-4′), 4.19(1H, m, H-5′), 4.52(2H, m, H-6′),
4.12(2H, m, H-1), 5.50(1H, t, J=7.5Hz, H-3),
3.63(1H, m, H-4), 4.16(1H, m, H-5), 3.61(2H, m,
H-6), H-2″, H-2 (6.38, 1H, d, J=16.0 Hz;6.42,
819Vol.20 　　　　　　LIXing-yu, etal:ChemicalConstituentsofOxyriadigyna　
1H, d, J=16.0 Hz), H-3″, H-3 (7.64, 1H, d, J=
16.0 Hz;7.71, 1H, d, J=16.0 Hz), H-5″, H-5
(7.18, 1H, s;7.24, 1H, s), H-8″, H-8 (6.80, 1H, d,
J=8.0 Hz;6.79, 1H, d, J=8.0 Hz), H-9″, H-9
(7.13, 1H, dd, J=8.5, 1.6 Hz;7.09, 1H, dd, J=
8.0, 1.6 Hz), 3.89(6H, s, OMe), 2.08(3H, s,
OAc);13CNMR(CD3OD, 100 MHz)δ:92.6(C-1′),
73.2(C-2′), 74.4(C-3′), 72.0(C-4′), 72.2(C-5′),
65.8(C-6′), 65.6(C-1), 105.0(C-2), 79.0(C-3),
74.9(C-4), 81.3(C-5), 65.5(C-6), C-1″, C-1
(168.2, 168.8), C-2″, C-2 (115.1, 114.7), C-3″, C-
3 (147.2, 147.9), C-4″, C-4 (127.3, 127.3), C-5″,
C-5 (111.8, 112.1), C-6″, C-6 (151.3, 151.4), C-
7″, C-7 (149.6, 149.6), C-8″, C-8 (116.7, 116.7),
C-9″, C-9 (124.4, 124.3), 56.6(OMe), OAc(21.0,
172.9).ItsNMRspectraldatawereinconsistentwith
thosereported[ 14] .
Fig.1　Thestructuresofcompounds1-14
Acknowledgements　Wearegratefultoalthestafof
theCenterofAnalyticalandTestingintheStateKey
LaboratoryofPhytochemistryandPlantResourcesin
westernChina.
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(下转第 845页)
820 NatProdResDev　　　　　　　　　　　　　　　　　　　　 　Vol.20
经是杂交后的新品种 ,另外一方面 ,可能是提取分离
方法不同。由于玉米紫色植株色素中尚有 4种成分
未确定 ,所以应继续研究。
5　结论
　　玉米紫色植株色素属花色苷类色素 ,其水溶液
在 285和 515 nm有吸收峰 ,经高效液相色谱测定 ,
有 6种成分 ,经硅胶柱分离出两种主要成分 ,通过红
外光谱和核磁共振分析 ,两种主要成分分别是矢车
菊素-3-葡萄糖苷和 3′, 4′-二羟基花色素 -3-葡萄糖
苷 ,其含量分别占总量的 45.96%和 12.99%。
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845Vol.20 　　　　　　周　波等:玉米紫色植株色素主要成分的结构鉴定