全 文 ：天然产物研究与开发 NatProdResDev2009, 21:66-69, 83
文章编号:1001-6880(2009)01-0066-05
　
　
　ReceivedAugust20, 2007;AcceptedOctober29, 2007
＊CorrespondingauthorTel:86-871-5223255;E-mail:mhchiu@mail.
kib.ac.cn
黄瓜藤的化学成分研究
唐　静 1, 2 ,邱明华 1＊ ,张宪民 1 ,周立刚 2
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 , 昆明 650204;
2中国农业大学农学与生物技术学院 ,北京 100093
摘　要:从丽江产黄瓜藤甲醇提取物的氯仿部位分离得到 9个化合物 , 经理化和波谱分析鉴定为 α-菠甾醇(1)、
α-菠甾醇-3-O-β-D-葡萄糖苷(2)、β-谷甾醇(β-sitosterol, 3)、豆甾-7-烯-3-O-β-D-葡萄糖苷(4)、 22-亚甲基-9, 19-环
羊毛甾烷-3β-醇(5)、(2S, 3S, 4R, 10E)-2-(2′, 3′-二羟基二十四烷酰氨基)-10-十八烯-1, 3, 4-三醇(6)、(2S, 3S,
4R, 10E)-2-[ (2′R)-2-羟基二十四烷酰氨基 ] -10-十八烯-1, 3, 4-三醇(7)、(2S, 3S, 4R, 10E)-1-(β-D-葡萄糖苷)-2-
[ (2′R)-2-羟基二十四烷酰氨基 ] -10-十八烯-1, 3, 4-三醇(8)、大豆脑苷(9),除化合物 3外 , 其它化合物均为首
次从该植物中分离得到。
关键词:黄瓜;藤;化学成分
中图分类号:R284.1;Q946.8;S642.2 文献标识码:A
ChemicalConstituentsfromStemsofCucumissativusL.
TANGJing1, 2 , QIUMing-hua1＊ , ZHANGXian-min1 , ZHOULi-gang2
1StateKeyLaboratoryofPhytochemistryandPlantResourcesinWestChina, Kunming
InstituteofBotany, ChineseAcademyofSciences, Kunming650204 , China;
2ColegeofAgronomyandBiotechnology, ChinaAgriculturalUniversity, Beijing100093 , China
Abstract:NinecompoundswereisolatedfromthechloroformfractionofthemethanolextractofCucumissativusL.
stems, andtheirstructureswereelucidatedbyphysicochemicalpropertiesandspectroscopicanalysisasα-spinasterol
(1), α-spinasterol3-O-β-D-glucopyranoside(2), β-sitosterol(3), stigmast-7-en-3-O-β-D-glucopyranoside(4), 22-
methylene-9, 19-cyclolanostan-3β-ol(5), (2S, 3S, 4R, 10E)-2-(2′, 3′-dihydroxytetracosanoylamino)-10-octadecene-1,
3, 4-triol(6), (2S, 3S, 4R, 10E)-2-[ (2′R)-2-hydroxytetracosanoylamino] -10-octadecene-1, 3, 4-triol(7), (2S, 3S,
4R, 10E)-1-(β-D-glucopyranosyl)-2-[ (2′R)-2-hydroxytetracosanoylamino] -10-octadecene-1, 3, 4-triol(8), soya-cere-
brosideI(9).Byliteraturestudy, exceptforcompound3, theotherswereisolatedfromthisplantforthefirsttime.
Keywords:CucumissativusL;stem;chemicalconstituent
Introduction
CucumissativusL, whichbelongstoCucurbitaceae, is
nowwidelyplantedinthetemperateandtropical
zones, includingalthedistrictsinChina[ 1] .Itisone
ofthemostimportantvegetables, andthestemshave
beenusedintraditionalChinesemedicineforitsanti-
inflammatoryactivity.AccordingtothebookBenCao
GangMueditedbyShizhenLiofMingDynastyof
ancientChina, thestemscanexpandbloodvesseland
reducebloodpressure[ 2] .However, verylitleisknown
aboutitschemicalconstituentsfromthestems, though
somereportssuggestedthepresenceofsteroidsand
phenolicsinthisplant[ 3, 4] .Thepresentstudyinvolved
isolationandidentificationofninecompoundsfromthe
chloroformfractionofthemethanolextractfromstems
ofC.sativus.
Experimental
General
MeltingpointsweredeterminedusinganXRC-1micro-
meltingpointapparatus, anduncorrected.NMRspectra
(1HNMR, 13CNMRandDEPT)wererecordedonei-
therBrukerAV-400 orBrukerDRX-500 NMRinstru-
ments.Thechemicalshiftswereexpressedinppmasδ
valuesrelativetotetramethylsilane(TMS)withTMSas
aninternalstandard.MSspectrawererecordedonVG
AutoSpec-3000 spectrometer.Columnchromatography
wasperformedoneithersilicagel(200-300 mesh)or
SephadexLH-20 (25-100 μm, PharmaciaCompany).
TLCwasperformedonpre-coatedsilicagelF254 plates
(QingdaoHaiyangChemicalCompany, China), and
detectionwasprovidedbyUVat254 nmandspraying
with10% H2SO4 -EtOHfolowedbyheatingat100℃.
Plantmaterial
StemsofCucumissativusL.werecolectedinAugust,
2005 inLijiangofYunnanProvinceinthesouthwestof
China, whichwereidentifiedbyProf.ShukunChenof
KunmingInstituteofBotany.Thestemswerelefttodry
intheshadeatroomtemperaturetoaconstantweight.
AvoucherspecimenwasdepositedintheHerbariumof
theDepartmentofTaxonomy, KunmingInstituteofBot-
any, ChineseAcademyofSciences.
Extractionandisolation
Thedrystems(4.5 kg)ofC.sativusweregroundinto
powderandthenextractedforthreetimeswithmetha-
nolunderrefluxat60 ℃, 4 hextractionforeachtime.
Thecombinedfiltratewasconcentratedinvacuoat50
℃ usingarotaryevaporatortoafordaresidueas
methanolcrudeextract(330g), whichwasfurthersus-
pendedinwaterandextractedsuccessivelywithchloro-
form, andthenwithn-butanoltogivechloroformfrac-
tion(65g)andn-butanolfraction(60g).Chloroform
fractionwasthensubjectedtocolumnchromatography
onasilicagel(1200g, 200-300mesh), elutingwitha
gradientmixtureofCHCl3 -MeOH(from50∶1 to0∶1,
v/v)toyieldfivesub-fractionsbasedonTLCanalysis.
Sub-fraction1 (4.8 g)wasfurtherchromatographied
onasilicagel(200-300 mesh)usingpetroleumether-
acetone(from10∶1 to2∶1 , v/v)asaneluanttoyield
compounds1(5 mg)and3 (202 mg).Compound5
(41mg)wasisolatedfromsub-fraction2 (4.6 g)by
silicagel(200-300mesh)columnelutedwithpetrole-
umether-acetone(5∶1, v/v).Sub-fraction3 (3.5 g)
wasrepeatedlychromatographyedoversilicagel(200-
300mesh)elutedwithCHCl3 -MeOH(from30∶1to10
∶1, v/v), andthenonSephadexLH-20 elutingwith
MeOHtoyieldcompounds6 (36 mg)and7 (146
mg).Sub-fraction4(9.3g)waschromatographyedon
silicagel(200-300 mesh)usingCHCl3 -MeOH(from
20∶1 to5∶1 , v/v)asaneluanttogivethecompounds
2(886mg)and4 (35 mg).Compounds8 (674 mg)
and9(164mg)wereobtainedfromsub-fraction5(13
g)byrepeatedsilicagelchromatographyelutingwith
CHCl3 -MeOH(from10∶1 to2∶1, v/v)solventsys-
tem.
ResultsandDiscussion
α-Spinasterol(1)　Whiteneedles(MeOH), C29H48O,
mp.158-159 ℃, ESI-MSm/z:413 [ M+H] +.1H
NMR(CDCl3 , 500 MHz)δ:5.15 (1H, dd, J=9.1,
9.2Hz, 22or23-H), 5.03(1H, dd, J=8.6, 8.7 Hz,
22 or23-H), 3.60 (1H, m, 3-H), 1.03 (3H, d, J=
6.5 Hz, 21-CH3 ), 0.86 (3H, d, J= 6.0 Hz, 29-
CH3), 0.84 (6H, d, J=6.6 Hz, 26-CH3 and27-
CH3), 0.80 (3H, s, 19-CH3 ), 0.55 (3H, s, 18-
CH3);13CNMR(CDCl3 , 100MHz)δ:31.4(t, C-1),
31.8 (t, C-2), 71.1 (d, C-3), 38.1 (t, C-4), 40.3
(d, C-5), 29.7(t, C-6), 117.5 (d, C-7), 139.6 (s,
C-8), 49.5 (d, C-9), 34.2 (s, C-10), 21.6 (t, C-
11), 39.5 (t, C-12), 43.3 (s, C-13), 55.1 (d, C-
14), 23.0 (t, C-15), 28.5 (t, C-16), 55.9 (d, C-
17), 12.0 (q, C-18), 13.0 (q, C-19), 40.8 (d, C-
20), 21.0 (q, C-21), 138.2 (d, C-22), 129.5 (d, C-
23), 51.3 (d, C-24), 31.9 (d, C-25), 21.6 (q, C-
26), 19.0 (q, C-27), 25.4 (t, C-28), 12.2 (q, C-
29).TheNMRdatawereidenticaltothoseofliterature
[ 5].
α-Spinasterol3-O-β -D-glucopyranoside(2)　 Col-
orlessneedles(MeOH), C35H58 O6 , mp.275-277 ℃,
FAB-MS(negative)m/z:573 [ M-H] -.1H NMR
(MeOD, 500MHz)δ:5.30(1H, dd, J=8.7, 8.8 Hz,
22or23-H), 5.18(1H, dd, J=8.8, 8.7Hz, 22or23-
H), 4.88 (1H, d, J=6.4 Hz, 1′-H), 4.57 (2H, d, J
=11.6Hz, 6′-H), 4.39 (1H, t, J=11.5 Hz, 4′-H),
4.01 (1H, m, 3-H), 1.00 (3H, d, J=6.3 Hz, 21-
CH3), 0.92(3H, d, J=7.6Hz, 26-CH3), 0.89(3H,
t, J=6.8Hz, 29-CH3), 0.88 (3H, d, J=8.1 Hz, 27-
CH3), 0.73 (3H, s, 19-CH3 ), 0.59 (3H, s, 18-
CH3);13CNMR(MeOD, 100MHz)δ:37.5(t, C-1),
30.1 (t, C-2), 77.5 (d, C-3), 34.9 (t, C-4), 40.4
67Vol.21 　　　　　　TANGJing, etal:ChemicalConstituentsfromStemsofCucumissativusL.　
(d, C-5), 29.8 (t, C-6), 117.9 (d, C-7), 139.8 (s,
C-8), 49.8 (d, C-9), 34.7 (s, C-10), 21.9 (t, C-
11), 39.9 (t, C-12), 43.7 (s, C-13), 55.4 (d, C-
14), 23.4 (t, C-15), 29.8 (t, C-16), 56.6 (d, C-
17), 12.3 (q, C-18), 13.1 (q, C-19), 40.4 (d, C-
20), 21.9(q, C-21), 138.6(d, C-22), 129.9(d, C-
23), 49.8 (d, C-24), 32.2 (d, C-25), 21.6 (q, C-
26), 20.0 (q, C-27), 25.4 (t, C-28), 12.1(q, C-29),
102.5(d, C-1′), 75.4(d, C-2′), 78.3(d, C-3′), 72.0
(d, C-4′), 78.7 (d, C-5′), 63.2 (t, C-6′).TheNMR
datawereconsistentwiththoseofreported[ 6].
β-Sitosterol(3)　Colorlessneedles(EtOAc), C29H50
O, mp.143-144 ℃.Itwasconfirmedbycomparingit
withthestandardsample.
Stigmast-7-en-3-O-β-D-glucopyranoside(4)　Col-
orlesneedles(MeOH), C35 H60 O6 , mp.267-270 ℃,
FAB-MS(negative)m/z:575 ([ M-H] - , 100).1H
NMR(pyridine-d5 , 500MHz)δ:5.03(1H, d, J=7.7
Hz, 1′-H), 4.59 (2H, d, J=10.5 Hz, 6′-H), 4.38
(1H, t, J=11.7Hz, 4′-H), 4.01(1H, m, 3-H), 0.99
(3H, d, J=6.3 Hz, 21-CH3), 0.90 (3H, d, J=7.5
Hz, 26-CH3), 0.88(3H, t, J=6.9Hz, 29-CH3), 0.86
(3H, d, J=6.8Hz, 27-CH3), 0.72(3H, s, 19-CH3),
0.58 (3H, s, 18-CH3);13CNMR(pyridine-d5 , 100
MHz)δ:37.4 (t, C-1), 30.1 (t, C-2), 77.2 (d, C-
3), 34.8 (t, C-4), 40.3 (d, C-5), 30.1 (t, C-6),
117.9 (d, C-7), 139.7 (s, C-8), 49.7 (d, C-9),
34.6 (s, C-10), 21.8 (t, C-11), 39.9 (t, C-12),
43.7(s, C-13), 55.3 (d, C-14), 23.5 (t, C-15),
28.3(t, C-16), 56.4 (d, C-17), 12.1 (q, C-18),
13.1 (q, C-19), 36.9 (d, C-20), 19.2 (q, C-21),
34.5(t, C-22), 28.3 (t, C-23), 46.2 (d, C-24),
29.6 (d, C-25), 19.3 (q, C-26), 20.0 (q, C-27),
23.4(t, C-28), 12.2 (q, C-29), 102.4 (d, C-1′),
75.4 (d, C-2′), 78.7 (d, C-3′), 71.9 (d, C-4′),
78.5(d, C-5′), 63.0 (t, C-6′).TheNMRdatawere
equaltothoseofliterature[ 6] .
22-Methylene-9, 19-cyclolanostan-3β-ol(5)　White
plates(MeOH), C31H52O, mp.124-125 ℃, EI-MSm/
z:440(25), 315 (15), 300(50), 175 (90).1HNMR
(CDCl3 , 500 MHz)δ:4.66 (2H, d, J=5.0 Hz, 31-
CH2), 3.26 (1H, m, 3-H), 1.25 (3H, s, 26-H), 1.25
(3H, s, 27-H), 1.03 (3H, d, J=6.8 Hz, 21-CH3),
0.96 (3H, s, 29-CH3), 0.89 (3H, s, 18-CH3), 0.88
(3H, s, 28-CH3), 0.80 (3H, s, 30-CH3), 0.54, 0.32
(each1H, d, J=5.0Hz, 19-CH2);13CNMR(CDCl3 ,
100 MHz)δ:31.7 (t, C-1), 29.6(t, C-2), 78.5(d,
C-3), 40.8 (s, C-4), 47.0 (d, C-5), 21.1 (t, C-6),
27.9 (t, C-7), 47.8 (d, C-8), 19.7 (s, C-9), 26.0
(s, C-10), 26.0(t, C-11), 35.5 (t, C-12), 45.1 (s,
C-13), 48.5 (s, C-14), 32.7 (t, C-15), 26.8 (t, C-
16), 52.1 (d, C-17), 17.9 (q, C-18), 29.6 (t, C-
19), 36.9 (d, C-20), 18.3 (q, C-21), 158.3 (s, C-
22), 33.4 (t, C-23), 35.5 (t, C-24), 31.1 (d, C-
25), 21.0 (q, C-26), 22.5 (q, C-27), 19.5 (q, C-28),
25.4 (q, C-29), 15.4 (q, C-30), 107.3 (t, C-31).The
NMRdatawereidenticaltothoseofliterature[ 7].
(2S, 3S, 4R, 10E)-2-(2′, 3′-Dihydroxytetraco-
sanoylamino)-10-octadecene-1, 3, 4-triol(6)　
Whitepowder(MeOH), C42H83 O6N, FAB-MS(nega-
tive)m/z:696 [ M-H] -.1HNMR(pyridine-d5 , 500
MHz)δ:8.68 (1H, d, J=9.3Hz, NH), 5.53 (1H,
m, H-10), 5.50 (1H, m, H-11), 5.12 (1H, m, H-2),
4.76 (1H, m, H-2′), 4.55 (1H, m, H-3′), 4.54
(1H, dd, J=8.5, 4.2 Hz, H-1), 4.43 (1H, dd, J=
8.5, 4.2 Hz, H-1), 4.33 (1H, m, H-3), 4.28 (1H,
m, H-4), 1.98-2.06 (m), 1.25-1.31 (54H, m, 27 ×
CH2), 0.86 (6H, t-like, J=6.6 Hz, Me-18 andMe-
24′);13CNMR(pyridine-d5 , 100 MHz)δ:62.0 (t, C-
1), 53.1 (d, C-2), 76.3 (d, C-3), 72.9 (d, C-4),
33.9 (t, C-5), 26.6 (t, C-6), 33.0 (t, C-7), 33.4
(t, C-8), 32.2(t, C-9), 130.8 (d, C-10), 130.7(d,
C-11), 32.6 (t, C-12), 174.0 (s, C-1′), 76.8 (d, C-
2′), 73.7 (d, C-3′), 26.6 (t, C-4′), 29.6-30.3 (t,
C-13-16 andC-5′-22′), 23.0 (t, C-17 andC-23′),
14.3 (q, C-18, 24′).TheNMRdataresembledthose
ofliterature[ 8] .
(2S, 3S, 4R, 10E)-2-[ (2′R)-2-Hydroxytetraco-
sanoylamino] -10-octadecene-1, 3, 4-triol(7)　
Whitepowder(MeOH);mp.138-139 ℃;C42H83O5N;
FAB-MS(negative)m/z:680 ([ M-H] -);1HNMR
(pyridine-d5 , 500 MHz)δ:8.57 (1H, d, J=8.8 Hz,
NH), 5.52 (1H, m, H-10), 5.50 (1H, m, H-11),
5.10 (1H, d, J=4.3 Hz, H-2), 4.61 (1H, m, H-2′),
4.51 (1H, brs, H-1), 4.42 (1H, m, H-1), 4.33 (1H,
m, H-3), 4.27 (1H, m, H-4), 1.25-1.30 (54H, m, 27
68 NatProdResDev　　　　　　　　　　　　　　　　　　　　 　Vol.21
×CH2), 0.85(6H, t-like, J=6.7 Hz, Me-18andMe-
24′);13CNMR(pyridine-d5 , 100MHz)δ:62.0(t, C-
1), 52.9 (d, C-2), 76.9 (d, C-3), 73.0 (d, C-4),
33.3 (t, C-5), 26.8 (t, C-6), 32.2 (t, C-9), 130.8
(d, C-10), 130.7 (d, C-11), 33.0 (t, C-12), 175.3
(s, C-1′), 72.5 (d, C-2′), 35.7 (t, C-3′), 25.8 (t,
C-4′), 29.6-30.3 (t, C-13-16 andC-5′-22′), 22.9
(t, C-17 andC-23′), 14.3 (q, C-18 , 24′).TheNMR
datawereidenticaltothoseofliterature[ 9] .
(2S, 3S, 4R, 10E)-1-(β-D-Glucopyranosyl)-2-
[ (2′R)-2-hydroxytetracosanoylamino] -10-octade-
cene-1, 3, 4-triol(8)　Whitepowder(MeOH);C48H93
O10N;FAB-MS(negative)m/z, 842 ([ M-H] - , 100),
680(15).1HNMR(pyridine-d5 , 500 MHz)δ:8.54
(1H, d, J=8.8 Hz, NH), 5.50 (1H, m, H-10), 5.49
(1H, m, H-11), 5.27(1H, d, J=4.3 Hz, H-2), 4.93
(1H, d, J=6.9 Hz, H-1″), 1.24-1.31 (54H, m, 27×
CH2), 0.85 (6H, t-like, J=6.7 Hz, Me-18 andMe-
24′);13CNMR(pyridine-d5 , 100MHz)δ:70.4(t, C-
1), 51.9 (d, C-2), 75.9 (d, C-3), 72.5 (d, C-4),
33.9(t, C-5), 33.0 (t, C-6), 32.9 (t, C-7), 32.8
(t, C-8), 32.2 (t, C-9), 130.9 (d, C-10), 130.7 (d,
C-11), 33.3 (t, C-12), 175.7 (s, C-1′), 72.5 (d, C-
2′), 35.6(t, C-3′), 25.9(t, C-4′), 29.6-30.0 (t, C-
13-16 andC-5′-22′), 23.0 (t, C-17andC-23′), 14.3
(q, C-18, 24′);Glc:105.5 (d, C-1″), 75.2 (d, C-
2″), 78.5 (d, C-3″), 71.6 (d, C-4″), 78.6 (d, C-
5″), 62.7 (t, C-6″).TheNMRdatawereequalto
thoseofliterature[ 10] .
Soya-cerbrosideI(9)　Whitepowder(MeOH);C40
H75 O9N;FAB-MS(negative)m/z, 712 ([ M-H] - ,
100), 550(15).1HNMR(pyridine-d5 , 400 MHz)δ:
8.38(1H, d, J=8.8 Hz, NH), 5.77 (1H, m, H-5),
5.49(3H, m, H-4, H-8 andH-9), 4.92 (1H, d, J=
7.7Hz, H-1″), 4.51 (1H, m, H-6″b), 4.38 (1H, m,
H-6″a), 4.25 (2H, m, H-1aandH-3″), 4.21 (1H,
m, H-4″), 4.05 (4H, m, H-1b, H-2, H-3 andH-2″),
3.92(2H, m, H-2′andH-5″), 2.14(4H, brs, H-6, H-
7), 1.99 (2H, m, H-10), 1.71 (1H, m, H-3′), 1.37
(1H, m, H-4′), 1.25-1.35 (38H, m, 19×CH2), 0.86
(6H, t-like, J=6.9 Hz, H-18 andH-16′);13 CNMR
(pyridine-d5 , 100MHz)δ:70.2(t, C-1), 54.6(d, C-
2), 71.5(d, C-3), 131.1(d, C-4), 132.1 (d, C-5),
32.2 (t, C-6), 32.1(t, C-7), 130.0 (d, C-8), 132.1
(d, C-9), 32.9(d, C-10), 175.7(s, C-1′), 72.3(d,
C-2′), 35.7 (t, C-3′), 25.9 (t, C-4′), 29.6-30.0 (t,
C-11-16 andC-5′-14′), 23.0 (t, C-17 andC-15′),
14.3 (q, C-18, 16′);Glc:105.7 (d, C-1″), 75.2 (d,
C-2″), 78.5 (d, C-3″), 71.5 (d, C-4″), 78.6 (d, C-
5″), 62.7 (t, C-6″).TheNMRdataresembledthoseof
literature[ 9] .Insummary, ninecompoundswereisola-
tedfromthechloroformfractionofthemethanolextract
ofC.sativusL.stems.Theywereelucidatedbyphysico-
chemicalpropertiesandspectroscopicanalysisexcept
compound3 whichwasdeterminedtobeβ-sitosterolby
comparingwithitsTLCbehaviorwithstandardsam-
ple.Byliteraturestudy, thecompoundsexceptβ-sitos-
terolwereisolatedfromthisplantforthefirsttime.
Acknowledgements　Thisworkwassupportedbythe
grantsfrom NKIP foundation, XibuzhiguangUnion
Lab.ProgramofCAS, andthe11thFive-YearTechnolo-
giesR＆DProgrameofChina(2007BAD89B01).The
authorsaregratefultoProf.ShukunChenofKunming
InstituteofBotanyforplantspecimenidentification,
andProf.MinganWangoftheColegeofScience, Chi-
naAgriculturalUniversityforacriticalreviewofthe
manuscript.
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