全 文 ：　　　　　　 天然产物研究与开发　 　　　　　
2005　Vol.17　No.3 NATURAL PRODUCT RESEARCH AND DEVELOPMENT　 　　　　　　　　
　
　
　
　
　　Received January 5 , 2005;Accepted January 31 , 2005
　＊Corresponding author　Tel:86-21-50806728;E-mail:dyzhu@mail.shc-
nc.ac.cn
Studies on the Chemical Constituents of
Pleurospermum lindleyanum
TAN Jun-jie , JIANG Shan-hao ,ZHU Da-yuan＊
(State Key Laboratory of Drug Research , Shanghai Institute of Materia Medica , Shanghai Institutes for
Biological Sciences , Chinese Academy of Sciences , Shanghai 201203 , China)
Abstract:Fifty compounds were isolated from Pleurospermum lindleyanum(Lipsky)B.Fedtsch.They were identified to be 6 , 7-
dihydroxycoumarin (1),(+)-marmesin (2),marmesinin(3), 5 , 7 , 4′-trihydroxyflavone(4), kaempferol 3-O-α-L-rhamnopyra-
noside(5), luteolin 3′-O-β-D-glucopyranoside(6),(R)-6-hydroxy-3-(2-hydroxypropan-2-yl)-6-methylcy clohex-2-enone(7),
4-hydroxybenzoic acid(8), 3-methoxy-4-hydroxybenzoic acid(9), 3-methoxy-4 , 5-methylenedioxy benzoic acid (10), methyl
syringate(11), methyl syringate 4-O-β-D-glucopyranoside (12), zingerone 4′-O-β-D-glucopyranoside (13), 2-(4-hydrox-
ypheny l)-ethanol(14)and 1-octacosanol(15).All the compounds were obtained from the title plant for the first time and 7
was firstly found as natural product.
Key words:Pleurospermum lindleyanum ;coumarin;flavone;monoterpenoid;aromatic acid
天山棱子芹化学成分的研究
谭俊杰 ,蒋山好 ,朱大元＊
(中国科学院上海生命科学研究院上海药物研究所 国家新药研究重点实验室 ,上海 201203)
摘　要:从天山棱子芹中首次分离得到 15 个已知化合物 , 通过NMR、MS 及 IR等波谱数据 ,分别鉴定为 6 , 7-二羟
基香豆素(1),(+)-marmesin (2),marmesinin(3), 5 , 7 , 4′-三羟基黄酮 (4), 莰非醇 3-O-α-L-吡喃鼠李糖甙(5), 藤
黄菌素 3′-O-β-D-吡喃葡萄糖甙(6),(R)-6-hydroxy-3-(2-hydroxypropan-2-yl)-6-methy lcyclohex-2-enone(7), 4-羟基苯
甲酸(8), 3-甲氧基-4-羟基苯甲酸(9), 3-甲氧基-4 , 5-亚甲二氧基苯甲酸(10),丁香酸甲酯(11), 丁香酸甲酯 4-
O-β-D-吡喃葡萄糖甙(12),姜油酮 4′-O-β-D-吡喃葡萄糖甙(13), 2-(4-羟基苯基)-乙醇(14)和 正二十八醇(15)。
其中化合物 7为一新的天然产物 。
关键词:天山棱子芹;香豆素;黄酮;单萜;芳香羧酸
中图分类号:R284.1
Pleurospermum lindleyanum (Lipsky)B.Fedtsch is a Chi-
nese folk medicine , used for the treatment of hyperten-
sion , coronary heart disease , high altitude sickness and
hepatitis in Xinjiang Uigur Autonomous Region.Previously
studies reported the isolation of 11 compounds from the
aerial parts of P.lindleyanum[ 1 ,2] .In the course of phy-
tochemical investigation on the whole plants , we obtained
15 known compounds , including three coumarins ,6 , 7-di-
hydroxycoumarin(1),(+)-marmesin(2)and marmesinin
(3), three flavonoids , 5 , 7 , 4′-trihydroxyflavone (4),
kaempferol 3-O-α-L-rhamnopyranoside (5)and luteolin
3′-O-β-D-glucopyranoside (6), one monoterpenoid ,(R)-
6-hydroxy-3-(2-hydroxypropan-2-yl)-6-methylcyclohex-2-
enone (7)and five aromatic acids , 4-hydroxybenzoic acid
(8),3-methoxy-4-hydroxybenzoic acid(9), 3-methoxy-4 ,
5-methylenedioxy benzoic acid (10), methyl syringate
(11) and methyl syringate 4-O-β-D-glucopyranoside
(12), as well as zingerone 4′-O-β-D-glucopyranoside
(13), 2-(4-hydroxyphenyl)-ethanol (14) and 1-octa-
cosanol(15).The above compounds were obtained from
the title plant for the first time and 7 was reported as nat-
ural product firstly.Here , we describe the isolation and
structure elucidation of these compounds.
267
Experimental
General
All melting points were determined on a BǜCHI 510 melt-
ing point apparatus and are uncorrected.Optical rotations
were measured using a Perkin-Elmer 341 polarimeter.IR
spectra were recorded on a Nicolet Magna 750 FTIR
(KBr)spectrometer.EI-MS data were obtained with a
MAT-95 mass spectrometer.NMR spectra were recorded
on a Bruker AV500 or Bruker DRX400 spectrometers , the
chemical shift values are reported in ppm(δ)and coupling
constants(J)are given in Hz.Silica gel(200 ～ 300 ,400
mesh)and precoated plates of silica gel(HSGF254)(Qing-
dao Haiyang Chemical Group Co.,Qingdao)were used for
column chromatography(CC)and TLC , respectively.
Plant material
The whole plants of P.lindleyanum were collected in
Tashikurgan ,Xinjiang Uigur Autonomous Region , China ,
in October 2000 , and identified by Prof.Guang-xing Yang
of Kashi Institute of Drug Research of Xinjiang.A voucher
specimen(No.0064)was deposited in our laboratory .
Extraction and isolation
The dried and powdered whole plants of P.Lindleyanum
(10 kg)were percolated with 95% EtOH(20 L ×3)at
room temperature.The concentrated extract was suspended
in H2O(3 L)and partitioned successively with petroleum
ether(PE , 60 ～ 90 ℃), CHCl3 , EtOAc , and n-BuOH(each 3 L×3).The CHCl3 fraction(77.4 g)was separat-
ed over silica gel column eluted with PE-Me2CO , PE-
CHCl3 , CHCl3-EtOAc , and CHCl3-Me2CO to give com-
pounds 2 , 7 ,9 , 10 , 11 and 15 , respectively.The EtOAc-
soluble fraction(33 g)was subjected repeatedly to CC on
silica gel eluted with CHCl3-MeOH , CHCl3-Me2CO , PE-
EtOAc , and CHCl3-EtOAc to yield successively com-
pounds 1 ,3 ,4 ,5 ,6 , 8 , and 14.The n-BuOH-soluble frac-
tion(145 g)was divided into H2O , 10%, 20%, 40%,
70%, and 95% EtOH subfractions through a macropore
resin D1400 (Yangzhou Pharmaceutical Factory ,
Yangzhou ,China)column( 10×65 cm).The 10%(6.6
g)and 20%EtOH(8.3 g)subfractions were further puri-
fied successively through silica gel , Sephadex LH-20 , and
ODS columns to afford compounds 12 and 13 , respective-
ly.
Identification
6 , 7-Dihydroxycoumarin(1)
Yellowish powder;1H NMR(DMSO-d6 , 500 MHz)δ:
9.83(br.s ,OH),7.86(d , J =9.5 Hz ,H-4),6.98(s ,H-
5),6.74(s ,H-8),6.16(d , J =9.5 Hz ,H-3);13C NMR
(DEPT ,DMSO-d6 ,125 MHz)δ:160.7(s , C-2), 112.3
(d ,C-3), 144.3(d ,C-4), 111.5(d ,C-5), 142.7(s , C-
6), 150.2(s , C-7), 102.6(d , C-8), 148.4(s , C-9),
110.7(s , C-10);EI-MS m/z(rel.int.):178 [ M] +
(100),150 [M-CO] +(90),121(11), 94(10),69(16),
51(12)[ 3 , 4] .
(+)-Marmesin(2)
White amorphous , [α] 20D +25.3°(c 0.59 ,CHCl3)(lit.[ 5]
[ α] 23D +21.7);1H NMR(CDCl3 ,400 MHz)δ:7.58(d ,
J =9.6 Hz , H-4),7.21(s ,H-5), 6.72(s ,H-8), 6.19
(d , J =9.6 Hz ,H-3), 4.73(dd , J =9.1 , 8.5 Hz ,H-
2′),3.21(2H ,m ,H-3′), 1.36 , 1.23(each 3H , s ,H-5′,
6′);13C NMR(DEPT)(CDCl3 ,100 MHz)δ:161.4(s ,C-
2),112.3(d , C-3), 143.6(d , C-4), 123.4(d , C-5),
268 天然产物研究与开发　　　　　　　　　　　　　 　　　2005　Vol.17　No.3
125.1(s ,C-6), 163.2(s ,C-7),97.9(d ,C-8),155.7(s ,
C-9),112.8(s , C-10), 91.1(d ,C-2′), 29.5(t ,C-3′),
71.6(s ,C-4′),26.1 ,24.3(each 1C ,q ,C-5′,6′);EI-MS
m/z(rel.int.):246 [M] +(45), 228 [ M-H2O] +(4),
213 [ 228-CH3] +(24), 188 [ M-58] +(75), 187 [ M-
59] +(100),175(13),160 [ 188-CO] +(26), 159 [ 187-
CO] +(10),131 [ 159-CO] +(16),59(22)[ 5 ,6] .
Marmesinin(3)
Colorless needles , mp.258 ～ 260 ℃, [ α] 20D-18.4°(c
0.495 ,DMSO);1H NMR(DMSO-d6 , 400 MHz)δ:7.94(d , J =9.5 Hz , H-4), 7.48(s , H-5), 6.81(s , H-8),
6.22(d , J =9.5 Hz ,H-3), 4.83(m ,H-2′), 4.41(d , J
=7.8 Hz ,Glc-1), 1.26 ,1.23(each 3H , s ,H-5′,6′);13C
NMR(DEPT , DMSO-d6 , 100 MHz)δ:160.5(s , C-2),
111.3(d , C-3),144.7(d , C-4), 123.9(d , C-5), 125.6
(s ,C-6),163.1(s ,C-7),96.8(d ,C-8),155.0(s , C-9),
112.2(s ,C-10),90.1(d ,C-2′),28.8(t ,C-3′),76.9(s ,
C-4′),23.1 , 21.8(q , C-5′, 6′), 97.3(d , Glc-1), 73.5
(d , Glc-2), 76.5(d ,Glc-3), 70.1(d ,Glc-4),76.9(d ,
Glc-5), 60.9(d , Glc-6);EI-MS m/ z(rel.int.):408
[M] +(16), 246 [M-162] +(14),229 [ 246-OH] +(58),
213(35),187(100),160(9),131(10),59(10)[ 7 ,8] .
5 ,7 ,4′-Trihydroxyflavone(4)
Yellowish powder;1H NMR(DMSO-d6 , 500 MHz)δ:
12.96(br.s ,OH-5),10.63(br.s ,OH-7),7.91(2H ,d , J
=8.6 Hz ,H-2′,H-6′),6.92(2H ,d , J =8.6 Hz ,H-3′,
H-5′),6.77(s ,H-3),6.48(s ,H-8),6.18(s ,H-6),3.42
(br.s , OH-4′);13C NMR(DEPT , DMSO-d6 , 125 MHz)δ:163.7(s ,C-2),102.8(d ,C-3),181.7(s ,C-4),161.4
(s ,C-5),98.8(d , C-6), 164.1(s ,C-7),93.9(d ,C-8),
157.3(s ,C-9),103.6(s ,C-10), 121.2(s , C-1′), 128.4
(d ,C-2′,C-6′),115.9(d ,C-3′,C-5′), 161.1(s ,C-4′);
EI-MS m/z(rel.int.):270 [M] +(100),253 [M-OH] +
(1.5),242 [M-CO] +(19), 213 [M-H-2CO] +(3),197
[ 253-2CO ] + (1), 153 [ C7H5O4 ] + (20), 124
[C6H4O3] +(10),121(13),96 [ 124-CO] +(4), 84(5),
69(6),51(2)[ 9 , 10] .
Kaempferol 3-O-α-L-rhamnopyranoside(5)
Yellowish powder;1H NMR(CD3OD , 500 MHz)δ:7.75(2H ,d , J =8.5 Hz ,H-2′, H-6′), 6.93(2H , d , J =8.5
Hz ,H-3′,H-5′),6.36(s ,H-8),6.19(s ,H-6),5.37(d ,
J =1.1 Hz , rha-1), 4.22(dd , rha-2), 3.71(dd , J =
8.4 ,3.0 Hz , rha-3),3.33(2H ,m , rha-4 , 5),0.92(3H ,
d ,J =5.2 Hz , rha-6);13C NMR(DEPT , CD3OD , 125
MHz)δ:159.5(s ,C-2),136.5(s ,C-3), 179.9(s , C-4),
163.5(s ,C-5), 100.2(d ,C-6),166.4(s ,C-7),95.1(d ,
C-8),158.9(s ,C-9),106.2(s , C-10), 123.0(s ,C-1′),
132.2(d , C-2′, C-6′), 116.8(d ,C-3′,C-5′),161.9(s ,
C-4′),103.8(d , rha-1), 72.2(d , rha-2), 72.4(d , rha-
3),73.5(d , rha-4), 72.3(d , rha-5), 17.9(3H , q , rha-
6);EI-MS m/z(rel.int.):432 [ M] +(0), 286 [M-
rha] +(100),269 [ 286-OH] +(1), 258 [ 286-CO] +(8),
241 [ 269-CO] +(1),229(7),213(4), 184(1), 153(3),
143(4),121(7),93(2),69(2),51(1)[ 11] .
Luteolin 3′-O-β-D-glucopyranoside(6)
Yellowish powder;1H NMR(DMSO-d6 , 400 MHz)δ:
12.95(br.s ,OH-5), 7.77(d , J =1.6 Hz ,H-2′), 7.63
(dd , J =8.5 , 1.6 Hz ,H-6′), 6.95(d , J =8.5 Hz ,H-
5′),6.78(s ,H-8), 6.51(s ,H-3), 6.16(s ,H-6), 4.88
(d , J =7.5Hz ,Glc-1),3.17-3.50(5H ,m)and 3.75(d ,
J =10.0 Hz)(Glc-2 ,3 ,4 ,5 ,6)[ 12] .
(R)-6-Hydroxy-3-(2-hydroxypropan-2-yl)-6-methyl-
cyclohex-2-enone(7)
White solid , [α] 20D-21°(c 0.8 ,CHCl3);1H NMR(CDCl3 ,
500MHz)δ:6.14(d , J =2.2 Hz ,H-2), 2.40 , 2.11
(each 1H ,m ,H-4),2.54 ,1.95(each 1H ,m ,H-5),1.26
(3H , s ,CH3-6),1.36 ,1.38(each 3H , s ,CH3);13C NMR(DEPT ,CDCl3 , 125 MHz)δ:203.1(s , C-1), 119.4(d ,
C-2),171.0(s ,C-3), 24.8(t ,C-4), 35.8(t ,C-5),72.8
(s , C-6), 23.9(q , CH3-6), 72.6(s), 28.8 , 28.7(q ,
CH3);EI-MS m/z(rel.int.):166 [M-H2O] +(98), 151
[ 166-CH3] +(18), 138 [ 166-2CO ] +(22), 126 [ C7H10
O2] +(46),125 [ 126-H] +(76),123 [ 138-CH3] +(44),
111 [ 126-CH3] +(100), 108 [ 126-H2O ] +(52), 95
[ 123-CO] +(36),80 [ 108-CO] +(45),59(57)[ 13] .
4-Hydroxybenzoic acid(8)
White solid;1H NMR(CD3OD ,500 MHz)δ:7.87(2H ,d ,
J =8.5 Hz ,H-2 ,H-6),6.81(2H , d , J =8.5 Hz ,H-3 ,
H-5);13C NMR(DEPT ,CD3OD ,100 MHz)δ:170.6(s ,
COOH),123.2(s ,C-1), 133.5(d , C-2 ,C-6), 116.5(d ,
C-3 , C-5), 163.8(s , C-4);EI-MS m/z(rel.int.):138
[M] +(70), 121 [M-OH] +(100), 110 [ M-CO] +(1),
93 [M-COOH] +(22),65 [ 93-CO] +(13),55(4)[ 14] .
3-Methoxy-4-hydroxybenzoic acid(9)
White powder;1H NMR(CD3OD ,300MHz)δ:7.75(2H ,
m ,H-2 ,H-6),7.03(d , J =8.7 Hz , H-5), 4.08(3H , s ,
MeO-3);13C NMR(DEPT ,CD3OD ,75.5 MHz)δ:170.6(s ,COOH),123.7(s ,C-1),114.4(d ,C-2),149.2(s ,C-
3),153.1(s ,C-4),116.3(d ,C-5),125.8(d ,C-6),56.9
(q ,MeO-3);EI-MS m/z (rel.int.):168 [ M] +(100),
153 [M-CH3] +(79), 125 [ 153-CO] +(24), 97 [ 125-
CO] +(25),79 [ 97-H2O] +(5),51 [ 79-CO] +(6)[ 15] .
3-Methoxy-4 ,5-methylenedioxy benzoic acid(10)
White powder;IR(KBr):υmax =2912.0 , 1681.6 ,
1637.3 , 1600.7 , 1511.9 , 1461.8 , 1436.7 , 1371.2 ,
1328.7 , 1276.7 , 1203.4 , 1120.5 , 1043.3 ,941.1 , 869.
8 ,763.7 ,707.8 cm-1;1H NMR(DMSO-d6 ,400MHz)δ:
2692005　Vol.17　No.3 谭俊杰等:天山棱子芹化学成分的研究 　
12.77(br.s ,COOH),7.26(s ,H-6),7.09(s ,H-2),6.10
(2H , s , O-CH2-O), 3.86(3H , s , MeO-3);13 C NMR
(DEPT ,DMSO-d6 ,100MHz)δ:166.5(s ,COOH),124.9
(s ,C-1), 103.1(d , C-2), 148.4(s , C-3), 138.9(s , C-
4),142.9(s ,C-5),109.8(d ,C-6),102.2(t ,O-CH2-O),
56.2(q , MeO-3);EI-MS m/ z(rel.int.):196 [ M] +
(100),179 [M-OH] +(11), 151 [ M-COOH] +(17),95
(4),79(5),51(4)[ 16 ,17] .
Methyl syringate(11)
Colorless needles , mp.104 ～ 105 ℃;1H NMR(CDCl3 ,
400MHz)δ:7.32(2H , s ,H-2 ,H-6), 5.95(br.s ,OH-
4),3.93(6H , s ,MeO-3 , 5),3.89(3H , s ,COOCH3);13C
NMR(DEPT ,CDCl3 ,100 MHz)δ:121.2(s , C-1), 106.8(2C , d ,C-2 ,6), 146.7(2C , s , C-3 , 5), 139.3(s ,C-4),
166.9(s , CO), 56.5(2C , q , MeO-3 , 5), 52.1(q ,
COOCH3);EI-MS m/z(rel.int.):212 [M] +(95),197
[M-CH3] +(13),183 [M-HCO] +(2), 181 [M-MeO] +
(100),165 [ 183-H2O] +(4),153 [ 181-CO] +(15),123
[ 181-2CO] +(6),108(5),97(4),79(3),53(4)[ 18] .
Methyl syringate 4-O-β-D-glucopyranoside(12)
White solid , [ α] 24D-17°(c 0.6 , MeOH);1H NMR(pyri-
dine-d5 ,500 MHz)δ:7.58(2H , s ,H-2 , 6),3.91(3H , s ,
COOCH3), 3.81(6H , s , MeO-3 , 5), 6.10(d , J =7.4
Hz ,Glc-1),4.37-4.54(4H ,m ,Glc-2 , 3 ,4 , 5),4.08(m ,
Glc-6)and 4.52(dd , J =11.9 , 2.3Hz ,Glc-6);13C NMR
(DEPT ,pyridine-d5 ,125 MHz)δ:166.7(s ,CO), 125.7(s ,C-1),108.3(2C ,d ,C-2 , 6),153.4(2C , s , C-3 ,5),
140.1(s , C-4), 56.6(2C , q , MeO-3 , 5), 52.1(q ,
COOCH3),104.1(d ,Glc-1),76.1(d ,Glc-2), 78.6(d ,
Glc-3),71.7(d , Glc-4), 79.2(d , Glc-5), 62.7(t ,Glc-
6);EI-MS m/z(rel.int.):212 [ M-Glc] +(100), 197
[ 212-CH3] +(4), 181 [ 212-MeO] +(25), 153 [ 181-
CO] +(3);ESI-MS:m/ z 397.1 [M +Na] +(positive),
373.1 [M-H]-(negative)[ 19] .
Zingerone 4′-O-β-D-glucopyranoside(13)
White solid , [ α] 22D +34(c 0.6 ,MeOH);1H NMR(pyri-
dine-d5 ,400 MHz)δ:2.12(3H , s ,H-1), 2.77(2H , t , J=7.4 Hz , H-3),2.95(2H , t , J =7.4 Hz , H-4),7.00
(d , J =1.9 Hz , H-2′), 7.60(d , J =8.3 Hz , H-5′),
6.85(dd , J =8.3 , 1.9 Hz , H-6′), 3.80(3H , s ,MeO-
3′),5.75(d , J =6.8Hz ,Glc-1),4.44(3H ,m ,Glc-2 ,3 ,
4),4.19(m ,Glc-5),4.62(dd , J =12.0 ,2.0 Hz ,Glc-6)
and 4.48(d , J =12.0Hz ,Glc-6);13C NMR(DEPT ,pyri-
dine-d5 ,100MHz)δ:29.9(q ,C-1),207.0(s ,C-2),45.
3(t ,C-3), 29.8(t ,C-4), 135.8(s , C-1′), 113.7(d , C-
2′),149.7(s ,C-3′),146.5(s ,C-4′), 116.8(d ,C-5′),
121.0(d ,C-6′),102.6(d ,Glc-1),75.1(d ,Glc-2),78.7
(d , Glc-3), 71.4(d ,Glc-4), 79.0(d , Glc-5), 62.5(t ,
Glc-6)[ 20] .
2-(4-hydroxyphenyl)-ethanol(14)
White solid;1H NMR(CD3OD , 400 MHz)δ:7.02(2H ,
dt , J =8.4 ,2.8 Hz ,H-2 ,6),6.70(2H ,dt , J =8.4 ,2.8
Hz ,H-3 ,5),3.68(2H , t , J =7.2 Hz ,H-α),2.70(2H , t ,
J =7.2 Hz ,H-β);13C NMR(DEPT ,CD3OD , 100 MHz)δ:131.5(s ,C-1),131.4(d ,C-2 , 6), 116.6(d ,C-3 ,5),
157.2(s ,C-4),65.1(t ,C-α),39.9(t ,C-β);EI-MS m/ z
(rel.int.):138 [ M] +(20), 107 [M-31] +(100), 120
[M-H2O] +(0.5),91 [C7H7] +(1),77(8),51(2)[ 21] .
1-Octacosanol(15)
White solid;1H NMR(CDCl3 ,400MHz)δ:3.64(2H , t , J=6.8 Hz ,H-1), 1.54(4H , m , H-2 , 3), 1.21 ～ 1.33
(48H ,m ,H-4 to H-27),0.87(3H , t ,6.6 Hz ,H-28);EI-
MS m/z(rel.int.):392 [ M-H2O] +(11), 378(1), 364
[ 392-C2H4] +(13),336(7),308(3), 280(3), 251(4),
237(4),209(7),195(8), 181(10), 167(11),153(15),
139(22),125(35),111(61),97(100),83(92),69(68),
57(86)[ 22 ,23] .
The physical and spectral data of compounds 1 ～ 15 were
in good agreement with those reported in the quoted litera-
tures.
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2712005　Vol.17　No.3 谭俊杰等:天山棱子芹化学成分的研究