全 文 ：Journal of Chinese Pharmaceutical Sciences214
Chemical constituents of Ixeris sonchifolia
Yan-Qin Lu, Chao-Feng Zhang and Mian Zhang*
Key Laboratory of Modern Chinese Medicines of Ministry of Education; Department of Pharmacognosy;
China Pharmaceutical University, Nanjing 210038, China
Abstract: Aim To investigate the chemical constituents of Ixeris sonchifolia Hance. Methods The chemical constituents were iso-
lated by various column chromatographic methods and the structures were elucidated and characterized by spectral evidences. Re-
sult Thirteen compounds were obtained and identified as 3β-acetoxy-20-taraxasten-22-one (1), bauerenyl acetate (2), 3β-acetoxy-
11-oxours-12-ene (3), oleanic acid (4), oleanane (5), 8-desoxyartelin (6), aesculetin (7), ferulic acid (8), vanillic acid (9),
sonchifolinin (10), hexacosanol (11), β-sitosterol (12), and daucosterol (13). Conclusion Compounds 1, 5, and 8 were isolated
from this genus for the first time; compound 7 was obtained firstly from this plant.
Keywords: Compositae; Ixeris sonchifolia; Chemical constituents
CLC number: R284.1 Document code: A Article ID: 1003–1057(2007)3–214–04
Introduction
Ixeris sonchifolia Hance (IS) (Compositae), also
named as Ku Mai Cai, Ku Die Zi or Man Tian Xing
in Chinese, is distributed widely in China, and often
grows on mountain slopes, roadsides or under forest.
It is belived to be able to clear away heat-evil, allevi-
ate pain and eliminate swelling, and has been applied
for treatment of coronary heart disease, angina pecto-
ris as well as their complicating diseases[1]. It was re-
ported to contain sesquiterpene lactones, flavonoids,
triterpenoid saponins, sterols, and lignins, but its ac-
tive constituents are still not clear[2–6]. In order to un-
derstand the medicinal function and develop a new
drug from IS, the chemical constitutes were studied
and reported in this paper.
Result and discussion
The petroleum ether and ethyl acetate extracts of IS
were subjected to column chromatography,
respectively, thirteen compounds were isolated and
identified as 3β-acetoxy-20-taraxasten-22-one (1),
bauerenyl acetate (2), 3β-acetoxy-11-oxours-12-ene
(3), oleanic acid (4), oleanane (5), 8-desoxyartelin
(6), aesculetin (7), ferulic acid (8), vanillic acid (9),
sonchifolinin (10), hexacosanol (11), â-sitosterol (12),
and daucosterol (13) (Figure 1). Compounds 1, 5, and
8 were isolated from this genus for the first time and
compound 7 firstly from this plant.
Received date: 2007-02-06.
*Corresponding author. Tel.: 86-25-85391246; fax: 86-25-85309639;
e-mail mianzhang@hotmail.com
Experimental
General
NMR data were obtained on Bruker ACF-300 (300
MHz) spectrometer with tetramethylsilane as an inter-
nal standard. ESI-MS experiments were performed on
an Agilent 1100 Series LC/MSD Trap mass analyzer.
Silica gel (100–200 mesh and 200–300 mesh,
Qingdao Ocean Chemical Factory) was used for col-
umn chromatography. Sephadex LH-20 was made by
Pharmacia Company.
Plant material
Herbs of Ixeris sonchifolia Hance were collected in
Meihekou City of Jilin Province in 2005 and was au-
thenticated by Dr. Zhang Mian (corresponding
author). A voucher specimen (No. BJKMC-050801)
was deposited in the herbarium of Department of
Pharmacognosy, China Pharmaceutical University.
Extraction and isolation
Dried and powdered herbs of I. sonchifolia (31 kg)
were extracted 3 times with 95% EtOH. The com-
bined extracts were concentrated to dry in vacuum
and the residue was suspended in water, partitioned
with petroleum ether, ethyl acetate, and n-butanol,
successively. The petroleum ether extract (1000 g)
was repeatedly chromatographed on silica gel
column, eluted gradiently with petroleum ether- ethyl
acetate, and purified by Sephadex LH-20 column
with chloroform-methanol (1:1) to yield compounds 1
Y. Q. Lu et al. / Journal of Chinese Pharmaceutical Sciences 2007 (16) 214–217 215
(5 mg), 2 (100 mg), 3 (38 mg), 4 (12 mg), 5 (1100
mg), 6 (220 mg) and 12 (1200 mg). The ethyl acetate
extract (285 g) was chromatographed on silica gel
column in gradient eluting with chloroform-methanol,
and purified by Sephadex LH-20 column with
chloroform-methanol to yield compounds 7 (6 mg),
8 (3 mg), 9 (3 mg), 10 (8 mg), 11 (20 mg) and 13
(56 mg).
Figure 1. Chemical constituents from Ixeris sonchifolia.
Structures identification
Compound 1. Colorless needles (CHCl3-MeOH).
ESI-MS m/z: 483.5[M+H]+; 1H NMR (CDCl3,
300MHz) ä: 5.71 (1H, br s, H-21), 4.48 (1H, dd, J =
10.5, 5.4 Hz, H-3), 2.04 (3H, s, C
O
CH3), 1.89
(3H, s, H-30), 1.12 (3H, d, J = 6.5 Hz, H-29), 1.07,
0.97, 0.93, 0.89, 0.86, 0.85 (each 3H, s, 6×-CH3);
data of 13C NMR listed in Table 1. The spectral data
of 1 were identical with those of 3â-acetoxy-20-
taraxasten-22-one[7].
Compound 2. White powder (CHCl3). 1H NMR
(CDCl3, 300 MHz) ä: 5.40 (1H, m, H-7), 4.52 (1H,
dd, J = 11.0, 4.5 Hz, H-3), 2.05 (3H, s, C
O
CH3 ),
1.06 (3H, s, H-29), 1.04, 1.00, 0.95, 0.93 (each 3H, s,
H-27, 26, 24, 23), 0.91 (3H, d, J = 5.9 Hz, H-30),
0.77, 0.85 (each 3H, s, H-28, 25); data of 13C NMR
listed in Table 1. The spectral data of 2 were identical
with those of bauerenyl acetate[8].
Compound 3. White powder (Petroleum ether-
EtOAc). 1H NMR (CDCl3, 300 MHz) ä: 5.54 (1H, s,
H-12), 4.52 (1H, dd, J = 11.5, 5.0 Hz, H-3), 2.05
(3H, s, C
O
CH3), 1.29, 1.19, 1.17 (each 3H, s,
3×CH3), 0.94 (3H, br s, CH3), 0.88 (6H, s, 2×CH3),
0.82 (3H, s, CH3), 0.80 (3H, br s, CH3); data of
13C NMR listed in Table 1. The spectral data of 3
were identical with those of 3â-acetoxy-11-oxours-
12-ene[6, 9].
Compound 4. White powder (CHCl3-MeOH). 1H
NMR (CDCl3, 300 MHz) ä: 5.27 (1H, m, H-12),
3.21 (1H, m, H-3), 1.14, 0.99, 0.93, 0.92, 0.90,
0.78, 0.76 (each 3H, s, 8×CH3); data of 13C NMR
listed in Table 1. The spectral data of 4 were identical
with those of oleanic acid [10].
Compound 5. Colorless needles (EtOH). 1H NMR
(CDCl3, 300 MHz) ä: 1.06, 1.01, 0.99, 0.97, 0.89,
0.87, 0.79, 0.76 (each 3H, s, 8×CH3). The spectral
data of 5 were in agreement with the reference [11],
and the Rf value and colouring behavior of TLC
were the same with oleanane (authentic substance).
Therefore, compound 5 was identified as oleanane.
Y. Q. Lu et al. / Journal of Chinese Pharmaceutical Sciences 2007 (16) 214–217216
s, 7-OH), 9.35 (1H, br s, 6-OH), 7.85 (1H, d, J =
9.3 Hz, 4-H), 6.16 (1H, d, J = 9.3 Hz, 3-H), 6.97
(1H, s, 5-H), 6.73 (1H, s, 8-H); 13C NMR (DMSO-d6,
75 MHz) δ: 160.7 (C-2), 111.4 (C-3), 144.3 (C-4),
112.3 (C-5), 150.3 (C-6), 148.4 (C-7), 102.6 (C-8),
142.8 (C-9), 110.7 (C-10). The spectral data of 7
were identical with those of aesculetin[12].
Compound 8. Yellow granular (CHCl3-MeOH). ESI-
MS m/z: 192.8[M-H]–; 1H NMR (CD3COCD3, 300
MHz) δ: 3.90 (3H, s, OCH3), 7.33 (1H, d, J = 1.8
Hz, H-2), 7.14 (1H, dd, J = 2.0, 8.2 Hz, H-6), 6.87
(1H, d, J = 8.2 Hz, H-5), 6.37 (1H, d, J = 15.9 Hz,
H-8), 7.60 (1H, d, J = 15.9 Hz, H-7). The spectral
data of 8 were identical with those of ferulic acid[13].
Compound 9. Yellow granular (CHCl3-MeOH). ESI-
MS m/z: 166.8[M-H]–; 1H NMR (CD3COCD3, 300
MHz) δ: 6.91 (1H, d, J = 8.1 Hz, H-5), 7.60 (1H,
dd, J = 2.0, 8.1 Hz, H-6), 7.56 (1H, d, J = 2.0 Hz,
H-2), 3.90 (3H, s, OCH3). The spectral data of 9
were identical with those of vanillic acid[14].
Compound 10. Yellowish-brown powder (CHCl3-
MeOH). ESI-MS m/z: 423.0[M-H]–, 363[M-H-
CH3COOH]–, 319 [M-H-CH3COOH-CO2]–; 1H NMR
(MeOD, 300 MHz) δ: 7.30 (1H, d, J = 15.9 Hz, 14-H),
6.62 (1H, d, J = 15.9 Hz, 13-H), 7.03 (1H, d, J = 2.0
Hz, 16-H), 6.95 (1H, dd, J = 2.0, 8.2 Hz, 20-H), 6.77
(1H, d, J = 8.2 Hz, 19-H), 6.75 (1H, s, 6-H), 6.52
(1H, s, 4-H), 6.26 (1H, s, 10-H), 4.18 (1H, t, J = 5.4
Hz, 7-H), 2.73 (2H, d, J = 5.2 Hz, 21-H). The spectral
data of 10 were identical with those of sonchifolinin[10].
Compound 11. White lamellar (CHCl3-MeOH). EI-
MS m/z: 364[M-H2O]+, 57 (100%); 1H NMR
(CDCl3, 300 MHz) δ: 0.88 (1H, t, J = 6.6 Hz, CH3),
1.26 (br s, CH2), 1.57(2H, m, CH2CH2OH), 3.64
(2H, t, J = 6.6 Hz, CH2OH). The spectral data of 11
were identical with those of hexacosanol[5].
Compound 12 and 13 were identified as β-sitosterol
and daucosterol, respectively, by comparison with
the authentic substances.
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C 1 2 3 4
1 38 .5 36 .7 38 .9 38 .5
2 23 .7 24 .3 23 .6 27 .3
3 80 .9 81 .2 80 .7 79 .1
4 37 .8 37 .8 38 .1 38 .7
5 55 .4 50 .7 55 .1 55 .3
6 18 .1 24 .1 18 .6 18 .4
7 34 .2 116.4 33 .9 32 .7
8 41 .2 145.6 43 .7 39 .4
9 50 .2 48 .3 61 .5 47 .6
1 0 37 .0 35 .2 36 .9 37 .1
1 1 21 .7 16 .9 193.9 23 .0
1 2 27 .7 32 .6 130.5 122.7
1 3 38 .4 37 .8 164.8 143.6
1 4 42 .0 41 .4 45 .2 41 .6
1 5 26 .3 29 .0 28 .8 27 .7
1 6 28 .5 31 .6 27 .3 23 .4
1 7 44 .8 32 .2 32 .9 46 .6
1 8 45 .3 55 .1 59 .1 41 .1
1 9 36 .8 35 .5 39 .3 46 .0
2 0 162.5 38 .0 39 .3 30 .7
2 1 123.0 29 .3 30 .9 33 .9
2 2 206.0 37 .9 39 .1 32 .5
2 3 27 .9 27 .6 28 .1 28 .1
2 4 16 .5 15 .8 16 .7 15 .5
2 5 16 .4 13 .1 16 .5 15 .3
2 6 16 .1 23 .7 17 .5 17 .1
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2 8 18 .7 32 .2 28 .1 182.7
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blue fluorescence under 365 nm ultraviolet light.
1H NMR (DMSO-d6, 300 MHz) δ: 10.15 (1H, br
C
O
CH3
C
O
CH3
Y. Q. Lu et al. / Journal of Chinese Pharmaceutical Sciences 2007 (16) 214–217 217
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抱茎苦荬菜的化学成分研究
路艳芹, 张朝凤, 张勉
(中国药科大学 现代中药教育部重点实验室, 生药学研究室, 江苏 南京 210038)
摘要: 目的 研究抱茎苦荬菜 Ixeris sonchifolia Hance的化学成分。方法 用硅胶及Sephadex LH-20凝胶柱色谱法分离纯化化
合物, 运用波谱学方法确定化合物的结构。结果 从抱茎苦荬菜中分离鉴定了 13个化合物, 分别为 3β-acetoxy-20-taraxasten-22-
one (1), 乙酸降香萜烯醇酯(2), 3β-acetoxy-11-oxours-12-ene (3), 齐墩果酸(4), 齐墩果烷(5), 8-去氧青蒿内酯(6), 七叶内酯(7), 阿魏酸
(8), 香草酸(9), 抱茎苦荬菜素(10), 正二十六醇(11), β-谷甾醇(12), 胡萝卜苷(13)。结论 化合物 1、5、8为首次从苦荬菜属
(Ixeris)中分离得到, 化合物7首次从该植物中分离得到。
关键词: 菊科; 抱茎苦荬菜; 化学成分