全 文 ： 2010 年 7 月 第 8 卷 第 4 期 Chin J Nat Med July 2010 Vol. 8 No. 4 267








Steroids and Phenols from Sonchus arvensis

XIA Zheng-Xiang, LIANG Jing-Yu*
Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China
[ABSTRACT] AIM: To investigate the chemical constituents of Sonchus arvensis L. METHODS: Compounds were
isolated and purified by various chromatographic techniques, and their structures were elucidated by physicochemical
properties and spectroscopic data. RESULTS: Eleven chemical constituents were isolated and identified as ergost-6,
22-diene-3β, 5α, 8α-triol (1), stigmast-5-ene-3β, 7α-diol (2), stigmasta-5, 22-dien-3β, 7β-diol (3), 3β,5α, 6β-trihydroxy-
stigmast-7, 22-diene (4), stigmast-6β-hydroxy-4, 22-diene-3-one (5), β-sitosterol (6), daucosterol(7), isoscopoletin(8),
aesculetin (9), emodin(10), and apigenin(11). CONCLUSION: Compounds 1-5, 8-10 were isolated from the genus
Sonchus for the first time, which could be significant from the chemotaxonomic point of view.
[KEY WORDS] Sonchus arvensis; Steroid; Phenol; Chemical constituents
[CLC Number] R284.1 [Document code] A [Article ID] 1672-3651(2010)04-0267-03
doi: 10.3724/SP. J. 1009.2010.00267
1 Introduction
The genus Sonchus is composed of 8 species in China.
They have long been used as folk medicines for the treat-
ment of fever, stasis and inflammation. They also have
effects through the detoxification and mobilization of blood
circulation[1]. The plant, Sonchus arvensis, is valued as a
delicious and nutritional herb and has been used for the
treatment of caked breasts, asthma, coughs, and other chest
complaints and for calming the nerves. It also has insecti-
cidal properties and anti-inflammatory activity[2]. Flavonols
[3], flavonol glycosides[4-5], momoacyl galactosylglyc-
erols[6] , sesquiterpene lactones[7-8], and quinic acids [8]were
previously isolated from this plant. In this paper, we re-
ported the isolation and structural elucidation of eleven
compounds from the ethanol extract of S. arvensis L. These
compounds were identified as: ergost-6, 22-diene-3β, 5α,
8α-triol (1)[9], stigmast-5-ene-3β,7α-diol (2)[10], Stigmasta-5,
22-dien-3β,7β-diol (3)[11], 3β,5α, 6β-trihydroxys- tigmast-7,
22-diene(4)[12], stigmast-6β hydroxy-4, 22-diene-
3-one(5)[13], β-sitosterol(6), daucosterol(7), isoscopoletin
(8)[14], aesculetin (9)[15], emodin(10)[16] and apigenin(11)[17].
Among them compounds 1-5, 8-10 were found from the
genus for the first time. Those steroids and phenols could
be significant from the chemotaxonomic point of view.
2 Experimental
2.1 General experimental procedures
Melting points were measured on an XT-4 mi-

[Received on] 15-Dec-2009
[*Corresponding author] LIANG Jing-Yu: Prof., E-mail: jyli-
ang08@yahoo.com.cn
cro-melting point apparatus, uncorrected. NMR spectra
were recorded on Bruker ACF-500/300 NMR instrument
(1H: 500/300 MHz, 13C: 125/75 MHz) with TMS as the
internal standard. Mass spectra were obtained on a
VGZAB-2f mass spectrometer (EI-MS) and MS Agilent
1100 Series LC/MSD Trap mass spectrometer (ESI-MS).
All solvents used were of analytical grade (Tianjin Chemi-
cal Plant). Silica gel (200-300 μm; Qingdao Marine
Chemical Co., Ltd.), Sephadex LH-20 (25-100 μm; Phar-
macia) and Rp-C18 (20-45 μm; Fuji Silysia Chemical Co.,
Ltd.) were used for column chromatography. Thin-layer
chromatography was performed on silica gel GF254 (Qing-
dao Marine Chemical Co., Ltd.).
2.2 Plant material
The whole plant of S. arvensis L. was collected in
February 2007 in Shaoyang, Hunan Province, China, and
identified by Professor QIN Min-Jian (China Pharmaceuti-
cal University). A voucher specimen (No. 20070201) was
deposited in the Department of Natural Medicinal Chemis-
try, China Pharmaceutical University, Nanjing, China.
2.3 Extraction and isolation
The whole plant of S. arvensis L. (9.4 kg) was pul-
verized and extracted with refluxing (85% ethanol three
times, 3h each time). The EtOH extract was concentrated
under reduced pressure (1 345 g) and was then suspended in
hot water and extracted with petroleum ether (PE), and
ethyl acetate successively. The PE fraction (110 g) was
subjected to repeated silica gel, Sephadex LH-20 and ODS
column chromatography, and further purified by
recrystallization and furnished. Compounds 1 (5 mg), 2 (2
mg), 3 (6 mg), 4 (3 mg), 5 (7 mg), 6 (1 g), 7 (200 mg), 8 (7
mg), 9 (11 mg), 10 (8 mg) and 11 (12mg) were obtained.
XIA Zheng-Xiang, et al. /Chinese Journal of Natural Medicines 2010, 8(4): 267−269
268 Chin J Nat Med July 2010 Vol. 8 No. 4 2010 年 7 月 第 8 卷 第 4 期

3 Results and Discussion
Compound 1 white needles (methyl alcohol), EI-MS
m/z (430)+. 1H NMR (300 MHz, CDCl3) δ: 6.51 (1H, d, J =
8.5Hz, H-7), 6.25 (1H, d, J = 8.5 Hz, H-6), 5.22 (1H, dd, J
= 15.2, 7.4 Hz, H-23), 5.14 (1H, dd, J = 15.2, 8.0 Hz, H-22),
3.97 (1H, m, H-3), 1.00 (3H, d, J = 6.6Hz, H-28), 0.89 (3H,
s, H-19), 0.83 (3H, s, H-18), 0.83 (3H, d, J = 6.6 Hz, H-26),
0.80 (3H, d, J = 6.6 Hz, H-27). 13C NMR (75 MHz, CDCl3)
δ: 135.4 (C-7), 135.2 (C-23), 132.3 (C-22), 130.7 (C-6),
82.1 (C-8), 79.4 (C-5), 66.2 (C-3), 56.1 (C-17), 51.6 (C-14),
51.0 (C-9), 44.5 (C-13), 42.7 (C-24), 39.7 (C-20), 39.3
(C-12), 36.9 (C-10), 34.7 (C-4), 33.0 (C-25), 30.0 (C-2),
28.6 (C-15), 23.3 (C-16), 20.8 (C-27), 20.6 (C-11), 19.9
(C-26), 19.6 (C-21), 18.1(C-19), 17.5 (C-28), 12.8 (C-18).
Compound 1 was characterized as ergost-6, 22-diene-3β, 5α,
8α-triol by comparison of the physical and spectral data
with the reported data[9].
Compound 2 white needles (methyl alcohol), EI-MS
m/z (430)+ .1H NMR (500 MHz, CDCl3) δ: 5.60 (1H, d, J =
5.4Hz, H-6), 3.85 (1H, m, H-7), 3.59 (1H, m, H-3), 1.04
(3H, s, H-19), 0.93 (3H, d, J = 7.2 Hz, H-21), 0.85 (3H, t, J
= 6.9 Hz,H-29), 0.84 (3H, d, J = 7.2 Hz, H-27), 0.82 (3H, d,
J = 6.9 Hz, H-26), 0.68 (3H, s, H-18). 13 C NMR (125 MHz,
CDCl3) δ: 37.0 (CH,C-1), 31.4 (C-2), 71.4 (C-3), 42.1 (C-4),
143.9 (C-5), 123.8 (C-6), 65.3 (C-7), 37.5 (C-8), 42.3 (C-9),
37.4 (C-10), 20.7 (C-11), 39.2 (C-12), 42.1 (C-13), 49.4
(C-14), 25.9 (C-15), 28.3 (C-16), 55.7 (C-17), 11.6 (C-18),
18.2 (C-19), 36.1 (C-20), 18.8 (C-21), 33.9 (C-22), 26.0
(C-23), 45.8 (C-24), 29.1 (C-25), 19.8 (C-26), 19.0 (C-27),
23.0 (C-28), 12.0 (C-29). Compound 2 was characterized as
stigmast-5-ene-3β, 7α-diol by comparison of the physical
and spectral data with the reported data[10].
Compound 3 white needles (methyl alcohol), EI-MS
m/z (428)+ .1H NMR (500 MHz, CDCl3) δ: 5.29 (1H, br s,
H-6), 3.85 (1H, m, H-7), 3.59 (1H, m, H-3), 5.16 (1H, dd, J
= 15.2, 7.4 Hz, H-23), 5.04 (1H, dd, J = 15.2, 8.0 Hz, H-22),
1.04 (3H, s, H-19), 0.93 (3H, d, J = 7.2 Hz, H-21), 0.85 (3H,
t, J = 6.9 Hz, H-29), 0.84 (3H, d, J = 7.2 Hz, H-27), 0.82
(3H, d, J = 6.9 Hz, H-26), 0.68 (3H, s, H-18). Compound 3
was characterized as stigmasta-5, 22-dien-3β, 7β-diol by
comparison of the physical and spectral data with the re-
ported data[11].
Compound 4 white needles (methyl alcohol), EI-MS
m/z (444)+. 1H NMR (500 MHz, CDCl3) δ: 5.36 (1H, d, J =
4.0 Hz, H-7), 5.24 (1H, dd, J = 14.8, 7.8Hz, H-22), 5.16
(1H, dd, J = 14.8, 7.8 Hz, H-23), 4.08 (1H, m, H-3), 3.63
(1H, br s, H-6), 1.08 (3H, s, H-19), 1.03 (3H, d, J = 7.2 Hz,
H-21), 0.91 (3H, d, J = 6.9 Hz, H-26), 0.83 (3H, t, J = 6.9
Hz, H-29), 0.84 (3H, d, J = 7.2 Hz, H-27), 0.61 (3H, s,
H-18). Compound 4 was characterized as 3β, 5α,
6β-trihydroxystig- mast-7, 22-diene by comparison of the
physical and spectral data with the reported data[12].
Compound 5 white needles (methyl alcohol), EI-MS
m/z (426)+. 1H NMR (500 MHz, CDCl3) δ: 5.81 (1H, s,
H-4), 5. 16 (1H, dd, J = 15.1, 8.4 Hz, H-22), 5.02 (1H,dd, J
= 15.1, 8.1Hz, H-23), 3.49 (1H, m, H-7), 1.18 (3H, s, H-19),
1.04 (3H, d, J = 7.2 Hz, H-21), 0.84 (3H, d, J = 6.3 Hz,
H-26), 0.80 (3H, t, J = 6.9 Hz, H-29), 0.79 (3H, d, J = 7.2
Hz, H-27), 0.71 (3H, s, H-18). 13 C NMR (125 MHz,CDCl3)
δ: 34.2 (CH,C-1),31.8 (C-2), 200.3(C-3), 138.1 (C-4), 168.3
(C-5), 31.8 (C-6), 29.8 (C-7), 35.0 (C-8), 53.7 (C-9), 39.5
(C-10), 25.4 (C-11), 34.2 (C-12), 40.4 (C-13), 51.3 (C-14),
25.4 (C-15), 28.8 (C-16), 56.0 (C-17), 19.0 (C-18), 12.2
(C-19), 39.5 (C-20), 28.3 (C-21), 129.6 (C-22), 126.4
(C-23), 56.0 (C-24), 28.3 (C-25), 21.1 (C-26), 26.1 (C-27),
12.9 (C-28), 18.2 (C-29). Compound 5 was characterized as
stigmast-6β-hydroxy-4, 22-diene-3-one by comparison of
the physical and spectral data with the reported data[13].
Compound 6 white needles, mp: 124-125 °C.The
physical data of 6 are consistent with those of β-sitosterol
and showed the same color and equal Rf value with the
standard substance of β-sitosterol while both compounds
were applied on TLC. Furthermore, the melting point of the
mixture of 6 and β-sitosterol did not decrease. Therefore,
this compound was identified as β-sitosterol.
Compound 7 white needles, mp: 275-276 °C. It
showed the same color and equal Rf value with the standard
substance of daucostero1 when applied on TLC and eluted
with different developing solvents. So the compound was
characterized as daucosterol.
Compound 8 white needles (methyl alcohol) ESI-MS
(193)+, (191)- 1H NMR (500 MHz, CDCl3) δ: 6.29 (1H, d,
J = 8.0 Hz, H-3), 7.60 (1H, d, J = 8.0 Hz, H-4), 6.83 (1H, s,
H-5), 6.97 (1H, s, H-8), 5.65 (1H, s, OH-6), 3.95 (3H, s,
OH3). Compound 8 was characterized as isoscopoletin by
comparison of the physical and spectral data with the re-
ported data [14].
Compound 9 white needles (methyl alcohol), ESI-MS
(179)+, 1H NMR (500 MHz, CD3OD), 7.75 (1H, d, J = 9.5
Hz, H-4), 6.91(1H, s, H-5), 6.73 (1H, s, H-8), 6.16 (1H, d, J
= 9.5 Hz, H-3). Compound 9 was characterized as aescu-
letin by the comparison of the physical and spectral data
with the reported data [15].
Compound 10 red needles, ESI-MS (269)-, 1H NMR
(500 MHz, DMSO-d6) δ: 12.09 (1H, s, α-OH), 12.02 (1H, s,
α-OH), 11.39 (1H, s, β-OH), 7.50 (1H, br s, 4-H), 7.17 (1H,
br s, 5-H), 7.12 (1H, d, J = 2.3 Hz, 2-H), 6.60 (1H, d, J =
2.3 Hz, 7-H), 2.43 (3H, br s, Ar-CH3). Compound 10 was
characterized as emodin by comparison of the physical and
spectral data with the reported data [16].
Compound 11 yellow powder, ESI-MS (269)-.1H
NMR (500 MHz, DMSO-d6) δ: 12.98 (1H, s, 5-OH), 10.84
(1H, s, 7-OH), 10. 38 (1H, s, 4’-OH), 6.79 (1H, s, H-3),
6.49 (1H, d, J = 1.6 Hz, H-8), 6.19 (1H, d, J = 1.6 Hz, H-6),
7.93 (2H, d, J = 8.8 Hz, H-2’,6’), 6.91 (2H, d, J = 8.8Hz,
XIA Zheng-Xiang, et al. /Chinese Journal of Natural Medicines 2010, 8(4): 267−269
2010 年 7 月 第 8 卷 第 4 期 Chin J Nat Med July 2010 Vol. 8 No. 4 269

H-3’,5’). Compound 11 was characterized as apigenin by
comparison of the physical and spectral data with the re-
ported data [17].
References
[1] Jiangsu College of New Medicine. A Dictionary of the Tra-
ditional Chinese Medicine [M]. Shanghai: Shanghai Science
and Technology press, 1977: 1286.
[2] Chinese Medicines Compile Group . The national traditional
Chinese medicines compilation [M]. Beijing: People’s Me-
dical Publishing House, 1975: 451.
[3] Bondarenko VG, Glyzin VI, Shelyuto TL. Flavonoids of
sonchus arvensis [J]. Khim Prir Soedin, 1976, 12 (4):
542-543.
[4] Bondarenko VG, Glyzin VI, Shelyuto TL. Sonchoside as a
new flavonoid glycoside from sonchus arvensis [J]. Khim
Prir Soedin, 1978, 14 (3): 403-405.
[5] Qu GR, Li XX, Liu JL. Chemical constituents of Sonchus
arvensis L [J]. China J Chin Mater Med, 1996, 21(5):
292-294.
[6] Baruah P, Baruah NC, Sharma RP, et al. A monoacyl galac-
tosylglycerol from Sonchus arvensis [J].Phytochemistry,
1983, 22(6): 1741-1744.
[7] Xu YJ, Sun SB, Sun LM, et al. Quinic acid esters and ses-
quiterpenes from Sonchus arvensis[J]. Food Chem, 2008,
111(1): 92-97.
[8] Xia ZX, Qu W, Lu HY, et al. Sesquiterpene lactones from
Sonchus arvensis L. and their antibacterial activity against
Streptococcus mutans ATCC25175 [J].Fitoterapia, 2010,
81(5), 424-428
[9] Kahols K, Kangas L, Hiltunen K. Erosterol peroside, an ac-
tive compound from Inobotus radiatus [J]. Planta Med, 1989,
55(4): 389-390.
[10] Marina DG, Pietro M, Lucio P. Stigmasterols from Typha
latifolia. [J]. J Nat Prod, 1990, 53(6):1430.
[11] Zhang J, Lu WG. Natural 5, 8-endoperoxy steroids and their
biological activities, spectroscopic properties and synthesis
[J]. Nat Prod Res Dev, 2006, 18(5): 883-887.
[12] Yasunori Y, Makiko E, Yoshino T, et al. Sterol constituens
from Seven Mushrooms. [J]. Chem Pharm Bull, 1999, 37(3):
847.
[13] Ling Y, Wan F, He BZ, et al. Chemical constituents of Pistia
st ratiotes L. [J]. China J Chin Mater Med, 1999, 24(5):
289-290.
[14] Geng D. Chemical constituents of Euphorbia helioscopia L.
and Illicium micranthum Dunn. [D]. China Pharm Univ Doc
Dissert, 2009: 41.
[15] Huang WH, Li YB, Jiang JQ. Chemical constituents from
Hedyotis diffusa [J]. China J Chin Mater Med, 2009, 34(6):
712-714.
[16] Li GL, Xiao YQ, Li L, et al. Studies on chemical constitu-
ents of roasted seeds of Cassia obtusifolia [J] China J Chin
Mater Med, 2009, 34(1): 54-56.
[17] Tian Y, Tang HF, Qiu F, et al. Antibacterial constituents of
extracts of the aerial parts of Discocleidion rufescens [J]. J
Shenyang Pharm Univ, 2009, 26(3): 191-195.

苣荬菜的甾体和酚类化学成分
夏正祥, 梁敬钰*
中国药科大学天然药物化学教研室, 南京 210009
【摘 要】 目的：研究苣荬菜的甾体和酚类化学成分, 为阐明其有效成分和植物化学分类学提供依据。方法：采用硅
胶、Sephadex-LH-20 及 Rp-18 等柱层析色谱方法进行化合物的分离纯化, 应用波谱解析和理化常数对照方法鉴定其结构.
结果：分离得到 11 个化合物, 分别鉴定为：麦角甾-6, 22-二烯-3β, 5α, 8α-三醇(1), 豆甾-5-烯-3β, 7α-二醇(2), 豆甾-5, 22-烯
-3β, 7α-二醇(3), 豆甾-7, 22-二烯-3β, 5α, 6β-三醇(4), 豆甾-6β-羟基-4, 22-二烯-3-酮(5), 谷甾醇(6), 胡萝卜苷(7), 异东莨宕
葶(8), 七叶内酯(9), 大黄素(10), 洋芹素(11)。结论：化合物 1 -5, 8-10 均为首次从该属植物中分离得到, 此类甾体和酚醇
可作为该属植物化学分类学依据。
【关键词】 苣荬菜; 甾体; 酚醇; 化学成分