全 文 ： 102 Chin J Nat Med Mar. 2012 Vol. 10 No. 2 2012 年 3 月 第 10 卷 第 2 期

Chinese Journal of Natural Medicines 2012, 10(2): 0102−0104
doi: 10.3724/SP.J.1009.2012.00102
Chinese
Journal of
Natural
Medicines







Chemical constituents from Monochasma savatieri
ZHENG Wei1, TAN Xing-Qi2*, GUO Liang-Jun1, KONG Fei-Fei1, LU Pin1,
NI Dong-Jie1, WANG Ping1
1No. 98 Hospital of PLA, Huzhou 313000, China；
2No. 102 Hospital of PLA, Changzhou 213002, China
Available online 20 Mar. 2012
[ABSTRACT] AIM: To study the chemical constituents of Monochasma savatierii Franch.. METHODS: The chemical constituents
were isolated and repeatedly purified by column chromatography with silica gel, Rp-C18, Sephadex LH-20 and identified by IR, MS
and NMR. RESULTS AND: Eight compounds were obtained and identified as 7, 8-dehydroboschnialactone (1), argyol (2), liquirti-
genin (3), β-sitosterol (4), p-hydroxycinnamic acid (5), 2-hydroxy-4-methoxybenzonic acid (6), p-hydroxyphenylethanol (7), proto-
catechuic acid (8). CONCLUSION: Compound 1 was obtained from natural source for the first time and the others have been isolated
from this plant for the first time.
[KEY WORDS] Monochasma savatierii; Scrophulariaceae; Chemical constituents
[CLC Number] R284.1 [Document code] A [Article ID] 1672-3651(2012)02-0102-03

1 Introduction
Monochasma savatieri Franch., known as “Longxucao ,
Baitouweng” etc. in China, is widely distributed in southern
China [1]. This plant was widely used in the treatment of
common cold, cough, bloody flux, menoxenia, toothache,
mammary abscess in Traditional Chinese Medicine. As for
the chemical constituent of this plant, only some phenols and
revertoses were reported. During our research, eight com-
pounds were isolated from this plant. These compounds were
identified as 7, 8-dehydroboschnialactone (1), argyol (2),
liquirtigenin (3), β-sitosterol (4), p-hydroxycinnamic acid (5),
2-hydroxy-4-methoxybenzonic acid (6), p-hydroxy- phenyle-
thanol (7), protocatechuic acid (8). Compound 1 was ob-
tained from natural source for the first time.
2 Experimental
2.1 Apparatus and reagents
Bruker-400 NMR (TMS as internal standard); ESI-MS
(MAT-95, Finigan); Silica gel GF254 plates (Yantai Jiangyou
Chemical Co., Ltd.). Silica gel (300−400 mesh; Yantai Jian-

[Received on] 21-Mar.-2011
[*Corresponding author] TAN Xing-Qi: associate chief pharmacist.,
E-mail: tanxq@sohu.com
These authors have no any conflict of interest to declare.
gyou Chemical Co., Ltd.); Sephadex LH-20 (GE Healthcare
Bio-Sciences AB); Rp-C18 gel (ODS-A 12 nm, s-50 μm, Ja-
pan); MCI resin (75−150 μm, Mitsubishi Chemical Corpora-
tion).
2.2 Plant material
The herb of Monochasma savatieri Franch. was col-
lected in Qiandaohu of Zhejiang Province, China, in June
2009, and botanically authenticated by author TAN Xing-Qi.
3 Extraction and Isolation
The air-dried herb of Monochasma savatieri Franch.(10
Kg) were ground and extracted with 75% EtOH (doused for
10 d), the extracted liquid was combined and concentrated in
vacuum on a rotary evaporator to afford a residue, which was
suspended in water and extracted with CHCl3. The CHCl3
fraction (64 g) was subjected to silica gel column chroma-
tography, being eluted with CHCl3−MeOH (20 : 1, 10 : 1, 8 :
1, 5 :1) to provide fractions 1−4. They were subjected respec-
tively to repeated column chromatography on silica gel,
Sephadex LH-20, Rp-C18 gel and MCI resin column chroma-
tography to give compounds 1, 2 and 4. The water layer (138
g) was subjected to macroporous resin column chromatogra-
phy, being eluted with EtOH−H2O [0% (1), 20% (2), 60% (3),
95% (4)] to provide fractions 1−4. Frs. 2 and 3 were sub-
jected to chromatography on silica gel column and then puri-
fied by Sephadex LH-20, Rp-C18 gel and MCI resin column
chromatography to give compounds 3, 5−8.
ZHENG Wei, et al. /Chinese Journal of Natural Medicines 2012, 10(2): 102−104
2012 年 3 月 第 10 卷 第 2 期 Chin J Nat Med Mar. 2012 Vol. 10 No. 2 103

4 Identification
Compound 1 White crystal; mp 40−41 °C; ESI-MS
m/z 151 [M − H]−, C9H12O2. Compound 1 was identified as 7,
8-dehydroboschnialactone by comparison of the physical and
spectral data with the literature [2], In the article, 1 was re-
ported as synthetic intermediate. So the compound 1 was
obtained from natural source for the first time. The 1H- and
13C NMR data are shown in Table 1.


1 2
Fig. 1 Structures of compounds 1 and 2

Table 1 NMR data of compound 1 (CDCl3)
NO. 13C NMR 1H NMR (J in Hz)
1

3
4
5
6

7
8
9
10
67.4

173.4
39.5
32.6
35.7

126.7
136.3
47.3
14.4
4.33 (dd, J = 11.5, 3.6 Hz, 1H)
4.26 (dd, J = 11.5, 4.2 Hz, 1H)

2.90−2.86 (m, 2H)
2.66 (dd, J = 15.1, 6.9 Hz, 1H)
2.78−2.61 (m,1H)
2.13−2.07 (m, 1H)
5.43 (s, 1H)

2.38 (dd, J = 14.7, 4.4 Hz,1H)
1.07 (s, 3H)

Compound 2 White crystal, ESI-MS m/z 193 [M +
Na]+, C9H14O3. 1H NMR (400 MHz, CDCl3) δ: 1.31 (3H, s,
H-10), 2.32 (H, m, H-9), 1.67 (H, ddd, H-7), 1.74 (H, ddd, J
= 12.5 Hz, H-7), 1.43 (H, dddd, J = 4.8, 6.8 Hz, H-6), 2.25
(H, dddd, J = 12.0, 8.5 Hz, H-6), 2.72 (H, m, H-5), 2.43 (H,
dd, J = 14.0, 7.5 Hz, H-4), 2.64 (H, dd, J = 7.0 Hz, H-4), 4.22
(H, dd, J =12.3, 7.9 Hz, H-1), 4.29 (H, dd, J = 5.8 Hz, H-1);
13C NMR (100 MHz, CDCl3) δ:173.5(C-3), 81.0 (C-8), 67.3
(C-1), 48.1 (C-9), 39.8 (C-4), 34.7 (C-7), 33.8 (C-5), 30.8
(C-6), 24.1 (C-10). Compound 2 was characterized as argyol
by comparison of the physical and spectral data with the lit-
erature [3].
Compound 3 Yellow powder (MeOH), mp 201−203
°C; crocus spots were visualized by spraying 10% H2SO4/
EtOH reagent followed by heating at 120 °C. ESI-MS m/z
255 [M − H] −, C15H12O4. 1H NMR (400 MHz, CD3OD) δ:
7.73 (1H, d, J = 8.7 Hz, H-5), 7.33 (2H, d, J = 8.4 Hz, H-2′,
6′), 6.82 (2H, d, J = 8.6 Hz, H-3, 5), 6.50 (1H, dd, J = 8.7,
2.6 Hz, H-6), 6.36 (1H, d, J= 2.6 Hz, H-8), 5.39 (1H, dd, J =
13.0, 3.0 Hz, H-2), 3.06 (1H, dd, J = 17.0, 13.0 Hz, H-3b),
2.70 (1H, dd, J = 17.0, 3.0 Hz, H-3a); 13C NMR (100 MHz,
CD3OD) δ: 193.5 (C-4), 166.8 (C-7), 165.6 (C-9), 159.0
(C-4), 131.4 ( C-1), 129.8 (C-5), 129.0 (C-2, 6), 116.3 (C-3,
5), 115.0 (C-10), 111.8 (C-6), 103.8 (C-8), 81.0 (C-2), 45.0
(C-3). Compound 3 was characterized as liquirtigenin by
comparison of the physical and spectral data with the litera-
ture [4].
Compound 4 White powder (CHCl3), mp 140−141 °C.
By comparing TLC behavior and melting point of compound
4 with those of β-sitosterol reference substance. ESI-MS m/z
413 [M − H] −, C29H50O. 1H NMR (400 MHz, CDCl3) δ: 5.35
(1H, t, H-6), 3.53(1H, m, H-3). This compound was deter-
mined to be β-sitosterol by comparison of the physical and
spectral data with the literature [5].
Compound 5 White needles (MeOH), mp 210−212
°C, ESI-MS m/z 163 [M − H]−, C9H8O3. 1H NMR (400 MHz,
DMSO) δ: 12.10 (1H, s, COOH), 9.93 (1H, s, 4-OH), 7.51
(2H, d, J = 8.4 Hz, H-2, 6), 7.47 (1H, d, J = 15.9 Hz, H-7),
6.79 (2H, d, J = 8.4 Hz, H-3, 5), 6.29 (1H, d, J = 15.9 Hz,
H-8); 13C NMR (100 MHz, DMSO) δ: 125.3 (C-1), 130.0
(C-2, 6), 115.3 (C-3, 5), 160.0 (C-4), 144.1 (C-7), 115.3 (C-8),
168 (CO). Compound 5 was characterized as p-hydroxyci-
nnamic acid by comparison of the physical and spectral data
with literature [6].
Compound 6 White needles (MeOH), mp 156−158
°C; ESI-MS m/z 169 [M + H]+, C8H8O4. 1H NMR (400 MHz,
DMSO) δ: 5.35 (OH), 7.56 (1H, d, J = 2.5 Hz, H-3), 7.58 (1H,
dd, J = 2.5, 8.8 Hz, H-5), 6.91 (1H, d, J = 8.8 Hz, H-6), 3.90
(3H, s, OCH3); 13C NMR (100 MHz, DMSO) δ: 115.1 (C-1),
164.5 (C-2), 100.6 (C-3), 166.8 (C-4), 108.3 (C-5), 135.1
(C-6), 55.6 (-OCH3). Compound 6 was characterized as
2-hydroxy-4-methoxybenzonic acid by comparison of the
physical and spectral data with the literature [7].
Compound 7 White crystal, mp 89−93 °C; ESI-MS
m/z 139 [M + H]+, C8H10O2. 1H NMR (400 MHz, DMSO) δ:
7.04 (2H, d, J = 8.3 Hz, H-2, 6), 6.74 (2H, d, J = 8.3 Hz, H-3,
5), 3.67 (H, t, J = 7.3 Hz, H-8), 2.70 (H, t, J = 7.4 Hz, H-7),
3.05 (OH), 5.35 (OH);; 13C NMR (100 MHz, DMSO) δ: 65.1
(C-1), 39.9 (C-2), 131.5 (C-3), 116.6 ( C-4, 8), 131.4 (C-5, 7),
157.2 (C-6). Compound 7 was characterized as p-hydroxy-
phenylethanol by comparison of the physical and spectral
data with the literature [8].
Compound 8 White crystal, mp 199−201 °C;
ESI-MS m/z 153 [M + H]+, C7H6O4. It was chromogenic with
spraying solution of FeCl3. 1H NMR (400 MHz, DMSO) δ:
7.33 (1H, dd, J = 8.4, 2.1 Hz, H-6), 7.32 (1H, d, J = 2.1 Hz,
H-2), 6.79 (1H, d, J = 8.5 Hz, H-5); 13C NMR (100 MHz,
DMSO) δ: 121.7 (C-1), 116.6 (C-2), 144.9 (C-3), 150.0 (C-4),
115.2 (C-8), 121.9 (C-6), 167.3 (COOH). Compound 8 was
characterized as protocatechuic acid by comparison of the
physical and spectral data with the literature [9].
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鹿茸草的化学成分
郑 巍 1, 谭兴起 2*, 郭良君 1, 孔飞飞 1，陆 萍 1, 倪东杰 1, 王 萍 1
1解放军第九八医院, 湖州 313000;
2解放军第一 0 二医院，常州 213002

【摘 要】 目的：对鹿茸草的化学成分进行研究。方法：反复采用硅胶, 反相硅胶, Sephadex LH-20 凝胶等方法分离、纯化
化合物, 通过红外光谱、质谱、核磁共振波谱法鉴定化合物结构。结果：分离得到 8 个化合物, 其结构鉴定为 7, 8-去氢草苁蓉内
酯(1), 阿基醇(2), 甘草素(3), β-谷甾醇(4), 对羟基桂皮酸(5), 2-羟基-4-甲氧基苯甲酸(6), 对羟基苯乙醇(7), 原儿茶酸(8)。结论：
化合物 1~8 都是首次从该植物中分得, 其中化合物 1 为首次从自然界中获得。
【关键词】 鹿茸草; 玄参科; 化学成分