全 文 ：






Chemical Constituents from the Aerial Part of
Peganum nigellastrum

YANG Fei1,2, CHEN Rong2, FENG Lin2, LI Hai-Dao2, ZHANG Hua2, LIANG Jing-Yu1*
1Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009;
2Jiangsu Simcere Pharmaceutical R&D Co., Ltd., Nanjing 210042, China
[ABSTRACT] AIM: To study the chemical constituents of Peganum nigellastrum Bge.. METHODS: The chemical
constituents were isolated by extraction, crystallization and chromatographic methods, and the chemical structures were
elucidated on the basis of spectral analysis. RESULTS: Six compounds were obtained, and their structures were identi-
fied as O-amino-N-formylbenzyamine(1), butyl 1H-imidazole-4-carboxylate (2), liriodendrin (3), trans-ferulic acid
β-D-glucopyranoside(4), (6S,7E,9R)-6,9-dihydroxymegastigma-4,7-dien-3-one-9-O-β-D-glucopyranoside (or roseoside)
(5) and (3S,5R,6R,7E,9S)-megastigman-7-ene-3,5,6,9-tetrol-3-O-β-D-glucopyranoside (6). CONCLUSION: Com-
pounds 1, 2 were isolated from natural resources, and compounds 3-6 were isolated from this genus for the first time.
[KEY WORDS] Peganum nigellastrum; Aerial part; Chemical constituents
[CLC Number] R284.1 [Document code] A [Article ID] 1672-3651(2010)03-0199-03
doi: 10.3724/SP. J. 1009.2010.00199
1 Introduction
Peganum nigellastrum Bge., family Zygophyllaceae,
is widely distributed over Asia and commonly found in
Xinjiang, Gansu, Inner Mongolia and Shanxi, China [1]. The
whole plants or seeds of P. nigellastrum have been used for
a long time in the treatment of rheumatism, irregular men-
struation, cough, asthma and so on. Since the inhibiting
activity of alkaloids from P. harmala L. on malignant tumor
of digestive tract was reported in 1975, considerable atten-
tion has been paid on the study of Peganum plants, mainly
P. harmala L. and P. multisectum Maxim [2]. The less repor-
ted plant P. nigellastrum were studied, and six compounds
were obtained, namely O-amino-N-formylbenzyamine(1),
butyl 1H-imidazole-4-carboxylate (2), liriodenrin (3),
trans-ferulic acid β-D-glucopyranoside (4), roseoside (5)
and (3S,5R,6R,7E,9S)-megastigman-7-ene-3,5,6,9-tetrol-3-
O-β-D-glucopyranoside (6). Compounds 1 and 2 were iso-
lated from natural resources, compounds 3-6 were isolated
from this genus for the first time.





[Received on] 26-Oct-2009
[*Corresponding author] LIANG Jing-Yu: Prof., Tel: 86-25-
83271415, E-mail: jyliang08@yahoo.com.cn
2 Experimental
2.1 General
Column chromatography (CC): Silica gel (200 – 300
mesh) and TLC was from Qingdao Marine Chemical Plant,
Qingdao, China; Sephadex LH-20 was purchased from GE
Healthcare Bio-Sciences AB; MCI gel was from Mitsubishi
Chemical Corporation, Tokyo, Japan. 1H-, 13C-, and
2D-NMR Spectra: Bruker-AV-500, 300 spectrometers; δ in
ppm rel. to Me4Si, J in Hz. MS: Agilent-1100-JC/MSD-
Trap (ESI-MS-MS) spectrometer; in m/z.
2.2 Plant material
P. nigellastrum aerial parts were collected from Min-
qin of Gansu province, China. A voucher specimen has
been deposited at the Herbarium of China Pharmaceutical
University, Nanjing, China.
2.3 Extraction and isolation
Dried aerial parts were extracted with 95% ethanol.
The concentrated extract (1 kg) was passed through a silica
gel column, eluted by petroleum, ethyl acetate, ethyl acetate
-methanol, and methanol in turn. The EtOAc fraction (230 g)
was subjected to repeated silica gel, Sephadex LH-20 and
MCI column chromatography, and further purified by re-
crystallization. At last, compounds 1 (12.3 mg), 2 (4.2 g), 3
(5.6 mg), 4 (10.6 mg), 5 (4.1 mg), and 6 (28.0 mg) were
isolated successfully.
3 Structural Identification
Compound 1 White amorphous powder, ESI-MS
m/z 151 [M + H]+, 185 [M + Cl]−, C8H10N2O. 1H NMR (500
MHz, CD3OD) δ：8.09 (1H, s, -CHO), 7.07 (1H, dd, J = 7.0,
2010 年 5 月 第 8 卷 第 3 期 Chin J Nat Med May 2010 Vol. 8 No. 3 199

YANG Fei, et al. /Chinese Journal of Natural Medicines 2010, 8(3): 199−201
200 Chin J Nat Med May 2010 Vol. 8 No. 3
1.0 Hz, H-6), 7.04 (1H, dt, J = 7.0, 1.0 Hz, H-4), 6.73 (1H,
dd, J = 7.0, 1.0 Hz, H-3), 6.65 (1H, dt, J = 7.0, 1.0 Hz, H-5),
4.81 (2H, s, H-7). 13C NMR(75 MHz, CD3OD) δ：163.7
(-CHO), 146.8 (C-2), 133.7 (C-1), 130.9 (C-4), 129.8 (C-6),
119.1 (C-5), 117.2 (C-3), 39.5 (C-7). Compound 1 was
characterized as O-amino-N-formylben-zyamine by com-
parison of the physical and spectral data with the reported
data [3], and it was isolated from natural resources for the
first time.
Compound 2 Pale yellow oil, C8H12N2O2. 1H NMR
(500 MHz, CDCl3) δ：7.71 (1H, dd, J = 5.0, 3.0 Hz, H-5),
7.52 (1H, dd, J = 5.0, 3.0 Hz, H-2), 4.30 (2H, t, J = 6.5 Hz,
H-7), 1.72 (2H, m, H-8), 1.44 (2H, m, H-9), 0.96 (3H, t, J =
7.0 Hz, H-10). 13C NMR (125 MHz, CDCl3) δ：167.7 (C-6),
132.3 (C-4), 130.8 (C-2), 128.8 (C-5), 65.5 (C-7), 30.5
(C-8), 19.1 (C-9), 13.6 (C-10). Compound 2 was character-
ized as butyl 1H-imidazole-4-carboxylate, and it was iso-
lated from natural resources for the first time.
Compound 3 White needle crystal, ESI-MS m/z 741
[M – H]−, 579 [M – glucose – H]−, 417 [M – 2glucose – H]−,
C34H46O18. 1H NMR (500 MHz, DMSO-d6) δ：6.66 (4H, s,
H-2, 2′, 6, 6′), 4.88 (2H, m, H-1), 4.67 (2H, d, J = 3.5 Hz,
H-7, 7′), 4.20 (2H, dd, J = 8.5, 6.5 Hz, Heq-9, Heq-9′), 3.83
(2H, d, J = 8.5, 3.0 Hz, Hax-9, Hax-9′), 3.10 (2H, m, H-8,
8′), 3.76 (6H, s, -OCH3). 13C NMR (125 MHz, DMSO-d6)
δ：152.6 (C-3, 3′, 5, 5′), 137.1 (C-4, 4′), 133.7 (C-1, 1′),
104.2(C-2, 2′, 6, 6′), 85.0 (C-7, 7′), 71.5 (C-9, 9′), 56.4
(-OCH3), 53.5 (C-8, 8′), 102.6 (C-1), 77.2 (C-5), 76.5
(C-3), 74.1 (C-2),70.1 (C-4), 60.9 (C-6). Compound 3
was characterized as liriodendrin by comparison of the
physical and spectral data with the reported data [4-5].
Compound 4 White powder, ESI-MS m/z 355 [M
–- H]−, 193 [M – glucose – H]−, C16H20O9. 1H NMR (500
MHz, CD3OD) δ：7.61 (1H, d, J = 16.0 Hz, H-7), 7.24 (1H,
d, J = 1.5 Hz, H-2), 7.16 (1H, dd, J = 7.5, 1.5 Hz, H-6),
7.13 (1H, d, J = 7.5, H-5), 6.38 (1H, d, J = 16.0 Hz, H-8),
3.90 (3H, s, -OCH3), 4.96 (1H, d, J = 7.0 Hz, H-1′), 3.86
(1H, m, H-6a′), 3.69 (1H, dd, J = 5.0, 11.5 Hz, H-6b′),
3.38-3.53 (4H, m, H-2′,3′,4′,5′). 13C NMR (125 MHz,
CD3OD) δ：170.8 (C-9), 151.0 (C-3), 149.9 (C-4), 145.8
(C-7), 130.7 (C-1), 123.3 (C-6), 118.1 (C-8), 117.5 (C-5),
112.5 (C-2), 102.3 (C-1′), 78.3 (C-5′), 77.8 (C-3′), 74.8
(C-2′), 71.3 (C-4′), 62.5 (C-6′), 56.8 (-OCH3). Compound 4
was characterized as trans-ferulic acid β-D-glucopyrano-
side by comparison of the physical and spectral data with
the reported data [6].
Compound 5 White powder, ESI-MS m/z 385 [M –
H]−, 223 [M – glucose – H]−, C19H30O8. 1H NMR (500 MHz,
CD3OD) δ：5.89 (1H, m, H-7), 5.86 (1H, m, H-8), 5.82 (1H,
br s, H-4), 4.42 (1H, m, H-9), 2.51 (1H, d, J = 17.0 Hz,
H-2a), 2.14(1H, d, J = 17.0 Hz, H-2b), 1.91 (3H, s, H-13),
1.28 (3H, d, J = 6.0 Hz, H-10), 1.03 (3H, s, H-12), 1.02 (3H,
s, H-11), 4.34 (1H, d, J = 7.8 Hz, H-1′), 3.84 (1H, dd, J =
11.5, 1.5 Hz, H -6a′), 3.62 (1H, dd, J = 11.5, 5.5 Hz, H-6b′),
3.16-3.34 (4H, H-2′, 3′, 4′, 5′). 13C NMR (125 MHz,
CD3OD) δ：201.2 (C-3), 167.5 (C-5), 135.3 (C-8), 131.5
(C-7), 127.2 (C-4), 80.5 (C-6), 77.3 (C-9), 50.7 (C-2), 42.5
(C-1), 24.7 (C-12), 23.4 (C-11), 21.2 (C-10), 19.5 (C-13),
102.7 (C-1′), 75.3 (C-2′), 78.0 (C-3′), 71.7 (C-4′), 78.1
(C-5′), 62.9 (C-6′). Compound 5 was characterized as
(6S,7E,9R)-6,9-dihydroxymegastigma-4,7-dien-3-one-9-O-
β-D-glucopyranoside (or roseoside) by comparison of the
physical and spectral data with the reported data [7].
Compound 6 White powder, ESI-MS m/z 441 [M +
Cl]−, C19H34O9. 1H NMR (500 MHz, CD3OD) δ：6.02 (1H,
dd, J = 15.5, 1.0 Hz, H-7), 5.75 (1H, dd, J = 15.5, 6.0 Hz,
H-8), 4.30 (1H, m, H-9), 4.16 (1H, m, H-3), 1.91 (1H, m,
H-4a), 1.68-1.75 (2H, m, H-2b, 4b), 1.54 (1H, m, H-2a),
1.23 (3H, d, J = 6.0 Hz, H-10), 1.17 (3H, s, H-13), 1.11 (3H,
s, H-11), 0.81 (3H, s, H-12), 4.37 (1H, d, J = 7.5 Hz, H-1′),
3.82 (1H, dd, J = 11.5, 2.0 Hz, H -6a′), 3.65 (1H, dd, J =
11.5, 5.0 Hz, H -6b′), 3.25-3.32 (3H, m, H-3′, 4′, 5′), 3.11
(1H, dd, H-2′). 13C NMR (125 MHz, CD3OD) δ：136.2
(C-8), 132.4 (C-7), 79.1 (C-6), 77.7 (C-5), 73.3 (C-3), 69.5
(C-9), 44.5 (C-2), 42.4 (C-4), 40.7 (C-1), 27.6 (C-11), 27.2
(C-13), 26.2 (C-12), 24.2 (C-10), 102.6 (C-1′), 75.1 (C-2′),
78.2 (C-3′), 71.7 (C-4′), 77.8 (C-5′), 62.8 (C-6′). Compound
6 was characterized as (3S,5R,6R,7E,9S)-megastigman-7
-ene-3,5, 6,9-tetrol-3-O-β-D-glucopyranoside by compari-
son of the physical and spectral data with the reported data [8].
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763-768

骆驼蒿的化学成分
杨 飞1,2, 陈 荣2, 冯 林2, 李海岛2, 章 华2, 梁敬钰1*
1中国药科大学天然药物化学教研室, 南京 210009;
2江苏先声药物研究有限公司, 南京 210042
【摘 要】 目的：对骆驼蒿( Peganum nigellastrum Bge.)地上部分进行化学成分的研究。方法：运用萃取、结晶及各
种层析方法进行分离纯化, 并通过理化鉴别和波谱分析鉴定化合物结构。结果：从骆驼蒿中分离鉴定了 6 个化合物, 分别
为：O-amino-N-formylbenzyamine (1), butyl 1H-imidazole-4-carboxylate (2), liriodendrin (3), trans-Ferulic acid β-D-glucopy-
ranoside (4), (6S,7E,9R)-6,9-dihydroxymegastigma-4,7-dien-3-one-9-O-β-D-glucopyranoside (or roseoside) (5), (3S,5R,6R,7E,
9S)-megastigman-7-ene-3,5,6,9-tetrol-3-O-β-D-glucopyranoside (6)。结论：化合物 1, 2 为首次从自然界分离得到, 化合物 3-6
首次从骆驼蓬属中分得。
【关键词】 骆驼蒿; 地上部分; 化学成分


·会 讯·

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2010 年 5 月 第 8 卷 第 3 期 Chin J Nat Med May 2010 Vol. 8 No. 3 201