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Chemical Constituents of Gentianella azurea

SHI Ke-Li, WANG Ye-Qing, JIANG Qian, LIAO Zhi-Xin*
Department of Pharmaceutical Engineering, School of Chemistry and Chemical Engineering, Southeast University, Nanjing 210009,
China
[ABSTRACT] AIM: To investigate the chemical constituents of Gentianella azurea. METHODS: The chemical con-
stituents were isolated and purified by silica gel, Sephadex LH-20 and Rp-18 column chromatographic methods. Their
structures were elucidated on the basis of physical characteristics and spectroscopic data. RESULTS: Nine compounds
were obtained and their structures were identified as 1-hydroxyl-3, 7, 8-trimethoxyxanthone (1), 1, 8-dihydroxyl-3,
5-dimethoxyxanthone (2), luteolin (3), β-daucosterol (4), hypolaetion (5), 1-hydroxyl-3, 5, 8-trimethoxyxanthone (6),
ursolic acid (7), swertianolin (8), and luteolin-5-O-β-D-glucoside (9). CONCLUSION: Compounds 1-3, 5-7, 9 are re-
ported in this plant for the first time.
[KEY WORDS] Gentianella; Gentianella azurea; Chemical constituent
[CLC Number] R284.1 [Document code] A [Article ID] 1672-3651(2010)06-0425-04
doi: 10.3724/SP. J. 1009.2010.00425
Gentianella azurea (Bunge) Holub, belonging to the
Gentianella, grows on hillside, in forest, meadow or billa-
bong, and is mainly distributed in such provinces as Gansu,
Qinghai, Tibet, Xinjiang and northwest of Yunnan [1]. As a
big genus of Gentianaceae, Gentianella is closely related
with Gentiana and prolonged to Gentiana. Gillet dis-
cussed the reasons for the building of Gentianella and set
up the classification of Gentianella in detail, and Pringle
and Ho approved the classification. In addition, the evi-
dences of embryology and molecular systematics had also
proved Gentianella for an obvious single family [2]. Xan-
thones and flavone C-glucosides are typical chemical con-
stituents of genus Gentianella. Xanthones are a class of
secondary metabolites with a variety of structures in oxida-
tion pattern and have been used as chemotaxonomic mark-
ers at infra and super-genus levels in the family Gentiana-
ceae [3]. On the other hand, the different oxidation patterns
of the xanthones could not distinguish the Gentiana from
Gentianella [2]. Gentianella azurea has been widely used in
Tibetan medicine as a top-grade herbal medicine to treat
fever and disorders of the gallbladder. Early investigation of
the plant resulted in the isolation of some Xanthones, fla-
vone C-glucosides and terpenoids [4]. It has been proved by
modern pharmacology that Xanthones have hypoglycemic,


Melting points (mp) were determined on an X-4 mi-
cromelting apparatus and uncorrected. NMR spectra were
measured on Bruker AV-300 and AV-500 instrument with
TMS as internal standard. IR spectra were recorded using a
Perkin-Elmer 577 spectrometer. EI-MS experiments were
carried out on a VG-ZAB-HS and JEOL JMX-HX110 mass
spectrometer, respectively. MCI gel (CHP 20P, 75-150 μm,
Mitsubishi Chemical Corporation, Japan) and Sephadex
LH-20 (Pharmacia Biotech, Sweden) were used for column
chromatography (CC). LiChroprep Rp-18(40-63 μm, Merck)
silica gel was used for column chromatography. Silica gel
was used for column chromatography, and precoated silica
GF
[Received on] 20-Aug.-2010
[Research Funding] This project is supported by the National Natural
Science Foundation of china（No.30770233）
[*Corresponding author] LIAO Zhi-Xin: Prof., Tel/Fax: 86-
25-52090620, E-mail: zxliao@seu.edu.cn
These authors have no any conflict of interest to declare.
anti-tumor, immunity and other biological activities [5]. In
order to find biologically active components from the plant,
the hall plant of Gentianella azurea collected in Qinghai
province was further investigated.
In this paper, we mainly reported the isolation and
structure elucidation of nine compounds isolated from the
plant. On the basis of spectral evidence and chemical
methods, the structures of the compounds identified were
1-hydroxyl-3, 7, 8-trimethoxyxanthone (1), 1,
8-dihydroxyl-3, 5-dimethoxyxanthone (2), luteolin (3),
β-daucosterol (4), hypolaetion (5), 1-hydroxyl-3, 5,
8-trimethoxyxanthone (6), ursolic acid (7), swertianolin (8),
luteolin-5-O-glucoside (9). Compounds 1-3, 5-7, 9 are re-
ported in this plant for the first time.
1 Apparatus and Reagents
254 plates were used for TLC (Qingdao Marine Chemical
Group Corporation, Qingdao, China). All solvents used
were of analytical grade.
2010 年 11 月 第 8 卷 第 6 期 Chin J Nat Med Nov. 2010 Vol. 8 No. 6 425

SHI Ke-Li, et al. /Chinese Journal of Natural Medicines 2010, 8(6): 425−428
426 Chin J Nat Med Nov. 2010 Vol. 8 No. 6
2 Plant Material
The dried whole plant material was collected in July,
2007 in the North Mountain National park of Qinghai
Province, China. It was identified by Prof. Chen Shi-Long
of Northwest Plateau Institute of Biology, Chinese Acad-
emy of Sciences, Xining, China. A voucher specimen (No.
20070803) was deposited in the Department of Pharmaceu-
tical Engineering, Southeast University, Nanjing.
3 Extraction and Isolation
The dried seeds of G. azurea (1.4 kg) were extracted
with 95% ethanol four times at room temperature. After the
solvents were evaporated under reduced pressure at 50 °C, a
residue (312.0 g) was obtained. The residue was suspended
in water and extracted by petroleum ether, ethyl acetate and
n-butanol, successively.
The petroleum ether fraction (12.6 g) was separated
by repeated column chromatography over normal and re-
verse silica gel, and MCI gel to yield compounds 1 (5 mg),
2 (11 mg), and 3 (4 mg).
The ethyl acetate extract (55.0 g) was subjected to
column chromatography over silica gel eluted with petrol
ether (PE)-ethyl acetate (EtOAc) (30 1 to ∶ 0 1∶ 00) to af-
ford five fractions ((A-E). Fraction A was further purified
over a Sephadex LH-20 column (30 cm × 53 cm, 200 mL)
eluted with MeOH to afford compound 4 (7 mg). The third
and fourth fractions were separated by column chromatog-
raphy on silica gel eluted with petroleum ether-acetone
(20 1), followed over LH∶ -20 to give compounds 5 (1 mg),
and 6 (3 mg). Fraction E was subjected to repeated CC (sil-
ica gel; CHCl3-MeOH) and Sephadex LH-20 column eluted
with MeOH to yield compound 7 (3 mg).
By the same means, the n-BuOH extract (170.0 g)
was subjected to a series of column chromatography over
silica gel eluted with CHCl3-MeOH (50 1 to ∶ 1∶3) and
Rp-18 column chromatography to yield compounds 8 (12
mg), and 9 (19 mg) (Fig. 1).

Fig. 1 Structures of compounds 1-9

4 Structural Identification
Compound 1 Yellow needles, mp 159-160 °C
(EtOH). IR (KBr) υmax: 3 100-2 600, 1 652, 1 603, 1 575 , 1
480, 1 160, 1 090 cm−1. EI-MS m/z 302 [M]+ . 1H NMR
(CDCl3, 300 MHz) δ: 13.24 (1H, s, C1-OH), 7.35 (1, d, J =
9.0 Hz, C6-H), 7.17 (1H, d, J = 9.0 Hz, C5-H), 6.33 (1H, d,
J = 2.4 Hz, C4-H), 6.31 (1H, d, J = 2.4 Hz, C2-H), 4.00 (3H,
s, C8-OCH3), 3.97 (3H, s, C7-OCH3), 3.88 (3H, s, C3-OCH3).
13C NMR (DMSO-d6, 125 MHz) δ: 163.8 (C-1), 96.8 (C-2),
166.6 (C-3), 92.3 (C-4), 112.9 (C-5), 120.4 (C-6),
149.3(C-7), 151.1 (C-8), 181.4 (C-9), 157.0 (C-4a), 149.7
(C-4b), 115.7 (C-8a), 104.1 (C-8b), 55.8 (C3-OCH3), 57.2
(C7-OCH3) 61.9 (C8-OCH3). Compound 1 was character-
ized as 1-hydroxyl-3, 7, 8-trimethoxyxanthone by compari-
son of its physical and spectral data with the literature[6].
Compound 2 Yellow needles, mp 186-187 °C
(acetone). IR (KBr) υmax: 3 200-2 800, 1 670, 1 640, 1 608,
1 582, 1 490 cm−1. EI-MS m/z: 288 [M]+. 1H NM R (CDCl3,
300 MHz) δ: 11.98 (1H, s, C1-OH), 11.39 (1H, s, C8-OH),
7.24 (1H, d, J = 8.5 Hz, C6-H), 6.72 (1H, d, J = 8.5 Hz,
C7-H), 6.55 (1H, d, J = 2.10 Hz, C4-H), 6.36 (1H, d, J = 2.1
Hz, C2-H), 3.96 (3H, s, OCH3), 3.90 (3H, s, OCH3). 13C
NMR (DMSO-d6, 125 MHz) δ: 162.9 (C-1), 97.3 (C-2),
167.5 (C-3), 93.1 (C-4), 139.9 (C-5), 120.4 (C- 6), 109.3
(C-7), 154.3 (C-8), 184.6 (C-9), 157.9 (C-4a), 145.5 (C-4b),
108.2 (C-8a), 102.8 (C-8b), 57.4 (C3-OCH3), 56.2
(C7-OCH3). Compound 2 was characterized as 1,
8-dihydroxyl-3, 5-dimethoxyxanthone by comparison of its
physical and spectral data with the literature [7].
Compound 3 Yellow powder, mp 328-330 °C
(MeOH). IR (KBr) υmax: 3 400, 2 966, 2 997, 1 653, 1 605,
1 561, 1 491, 1 275, 1 016, 831 cm−1. EI-MS m/z 286 [M]+.
1H NMR (DMSO-d6, 300 MHz) δ: 12.98 (1H, s, C5-OH),
10.79 (1H, s, C7-OH), 9.88 (1H, s, C3΄-OH) , 9.38 (1H, s,
C4΄-OH), 7.43(1H, dd, J = 8.2, 2.2 Hz, C6΄-H), 7.41 (1H, d,
J = 2.22 Hz, C2΄-H), 6.92 (1H, d, J = 8.16 Hz, C5΄-H), 6.67
(1H, s, C8-H), 6.46 (1H, d, J = 2.01 Hz, C3-H), 6.20 (1H, d,
J = 2.01 Hz, C6-H). 13C NMR (DMSO-d6, 75 MHz) δ:
164.3 (C-2), 103.3 (C-3), 181.8 (C-4), 157.6 (C-5), 99.2
(C-6), 164.4 (C-7), 94.2 (C-8), 161.6 (C-9), 104.0 (C-10),
119.4 (C-1΄) , 113.5 (C-2΄), 150.0 (C-3΄), 146.1 (C-4΄),
2010 年 11 月 第 8 卷 第 6 期

SHI Ke-Li, et al. /Chinese Journal of Natural Medicines 2010, 8(6): 425−428
116.4 (C-5΄), 121.6 (C-6΄). Compound 3 was characterized
as luteolin by comparison of its physical and spectral data
with the literature [8].
Compound 4 White powder, mp 295-297 °C
(MeOH). IR (KBr) υmax (cm−1): 3 410, 2 935, 2 867, 1 638,
1 380, 1 072, 1 025, 890 cm−1. EI-MS m/z: 576 [M]+. 1H
NMR (C5D5N, 500 MHz) δ: 5.35 (1H, t, C6-H), 5.03 (1H,
d, C1΄-H), 0.65-0.98 (6CH3). 13C NMR (C5D5N, 75 MHz) δ:
37.6 (C-1), 30.4 (C-2), 78.8 (C-3), 39.5(C-4), 140.6 (C-5),
122.0 (C-6), 32.3 (C-7), 32.2(C-8), 50.6 (C-9), 36.9 (C-10),
21.5 (C-11), 40.2 (C-12), 42.6 (C-13), 56.7 (C-14), 24.6
(C-15), 28.8(C-16), 56.1 (C-17), 12.4 (C-18), 19.7 (C-19),
36.2 (C-20), 19.3 (C–21), 34.3 (C-22), 26.1 (C-23), 46.1
(C-24), 29.7 (C-25), 20.2 (C-26), 19.4 (C-27), 23.3(C-28),
12.5 (C-29), 102.8 (C-1΄), 75.6 (C-2΄), 78.3(C-3΄), 71.8
(C-4΄), 78.6 (C-5΄), 62.9 (C-6΄). Compound 4 was charac-
terized as β-daucosterol by comparison of its physical and
spectral data with the literature [9].
Compound 5 Yellow needles, mp 298-301 °C
(MeOH). IR (KBr) υmax: 3 430, 1 653, 1 586, 1 482 cm−1.
EI-MS m/z 302 [M]+. 1H NMR (DMSO-d6, 300 MHz) δ：
12.39 (1H, s, C5-OH), 10.44 (1H, s, C8-OH), 9.83 (1H, s,
C6-OH), 8.67 (1H, s, C4΄-OH), 9.37 (1H, s, C3΄-OH), 6.26
(1H, s, C3-H), 7.47 (1H, d, J = 8.10, 2.10 Hz, C6΄-H), 6.88
(1H, d, J = 8.10 Hz, C5΄-H), 6.61 (1H, s, C6- H). Compound
5 was characterized as hypolaetion by comparison of its
physical and spectral data with the literature[10].
Compound 6 Yellow needles, mp 206-207 °C
(MeOH). IR (KBr) υmax: 3 100-2 600, 1 660, 1 610, 1 576, 1
485 cm−1. EI-MS m/z 302 [M] +. 1H NMR (CDCl3, 300
MHz) δ: 13.9 (1H, s, C1-OH), 7.17(1H, d, J = 9.00 Hz,
C6-H), 6.70 (1H, d, J = 9.00 Hz, C7-H), 6.49 (1H, d, J =
2.40 Hz, C4-H), 6.32 (1H, d, J = 2.40 Hz, C2-H), 3.98 (3H, s,
C8-OCH3), 3.97 (3H, s, C3-OCH3), 3.87(3H, s, C5-OCH3).
13C NMR (CDCl3, 125 MHz) δ: 163.6 (C-1), 97.6 (C-2),
166.5 (C-3), 92.3 (C-4), 142.1 (C-5), 116.9 (C-6), 104.5
(C-7), 156.9 (C-8), 181.5 (C-9), 153.7 (C-4a), 147.6 (C-4b),
111.9 (C-8a), 104.4 (C-8b), 57.0 (C8-OCH3), 56.5(C7-
OCH3), 55.9 (3-OCH3). Compound 6 was characterized as
1-hydroxyl-3, 5, 8-trimethoxyxanthone by comparison of its
physical and spectral data with the literature [11].
Compound 7 Yellow powder, mp 262-264 °C
(MeOH). IR (KBr) υmax: 2 870, 1 714, 1 385, 1 375 cm−1.
EI-MS m/z 456 [M]+, 423, 438, 410, 248, 207, 203, 189. 1H
NMR (DMSO-d6, 300 MHz) δ: 5.14 (1H, t, C12-H), 3.31
(1H, m, C3-H), 0.82 (3H, d, J = 6.4 Hz, C29-H), 0.91(3H, d,
J = 7.6 Hz, C30-H), 1.06, 0.93, 0.88, 0.78, 0.69 (each, 3H, s),
11.91 (1H, br s, COOH). 13C NMR (DMSO-d6, 75 MHz) δ:
38.4 (C-1), 26.9 (C-2), 76.8 (C- 3), 38.4 (C-4), 54.7 (C-5),
17.9 (C-6), 32.7 (C-7), 38.7 (C-8), 46.8 (C-9), 36.3 (C-10),
22.8 (C- 11), 124.5 (C-12), 138.1 (C-13), 41.6 (C-14), 28.2
(C-15), 23.8 (C-16), 47.0 (C-17), 52.3 (C- 18), 38.3 (C-19),
38.2 (C-20), 30.1 (C-21), 36.5 (C-22), 27.5 (C-23), 15.2
(C-24), 16.0 (C-25), 16.9 (C-26), 23.2 (C-27), 178.2 (C-28),
16.9(C-29), 21.0(C-30). Compound 7 was characterized as
ursolic acid by comparison of its physical and spectral data
with the literature [12].
Compound 8 Yellow powder, mp 241-242 °C
(MeOH). IR (KBr) υmax: 3 351, 1 650, 1 655, 1 615, 1 575,
1 495, 1 085 cm−1. EI-MS m/z 436 [M]+. 1H NMR (DMSO-
d6, 500 MHz) δ: 6.36 (1H, d, J = 2.00 Hz, C2-H), 6.57 (1H,
d, J = 2.00 Hz, C4-H), 7.27 (1H, d, J = 9.00 Hz, C7-H), 7.12
(H, d, J = 9.00 Hz, C6-H), 3.89 (3H, s, OCH3), 4.80 (1H, d,
J = 7.50 Hz, C1΄-H). 13C NMR (DMSO-d6, 75 MHz) δ:
162.7 (C-1), 97.1 (C-2), 166.2 (C-3), 92.1 (C-4), 140.9
(C-5), 121.1 (C-6), 112.3 (C-7), 149.4 (C-8), 181.0 (C-9),
56.1 (OCH3), 156.4 (C-4a), 145.0 (C-4b), 112.3 (C-8a),
103.5 (C-8b), 103.1 (C-1΄), 73.5 (C-2΄), 76.1 (C-3΄), 69.7
(C-4΄), 77.4 (C-5΄), 60.8 (C-6΄). Compound 8 was charac-
terized as swertianolin by comparison of its physical and
spectral data with the literature [13].
Compound 9 Yellow powder, mp 249-251 °C
(MeOH). IR (KBr) υmax: 3 348, 1 665, 1 610, 1 500, 1 453,
1 180, 843 cm−1. EI-MS m/z 448 [M]+. 1H NMR (DMSO-d6,
300 MHz) δ: 10.93 (1H, s, C7-OH), 9.81 (1H, s, C4΄-OH),
9.37 (1H, s, C3΄-OH), 6.80 (1H, d, J = 2.10 Hz, C8-H), 6.70
(1H, d, J = 2.10 Hz, C6-H), 6.54 (1H, s, C3-H), 7.36 (1H, dd,
J = 2.10Hz, C2΄-H), 7.38 (1H, dd, J = 2.10, 8.40 Hz, C6΄-H),
6.89 (1H, d, J = 8.40 Hz, C5΄-H), 4.72(1H, d, J = 7.2 Hz,
Glucose H-1). 13C NMR (DMSO-d6, 75 MHz) δ：162.5
(C-2), 105.6 (C-3), 176.8 (C-4), 158.6 (C-5), 104.3 (C-6),
161.3 (C-7), 98.1 (C-8), 158.3 (C-9), 108.8 (C-10), 121.5
(C-1΄), 113.1 (C-2΄), 145.6 (C-3΄), 149.2 (C-4΄), 115.9
(C-5΄), 118.5 (C-6΄), 104.5 (C-1΄΄), 73.6 (C-2΄΄), 77.5
(C-3΄΄), 69.7 (C-4΄΄), 75.6 (C-5΄΄), 60.8 (C-6΄΄). Compound
9 was characterized as luteolin-5-O-β-D-glucoside by
comparison of its physical and spectral data with the litera-
ture [14].
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黑边假龙胆的化学成分
史可丽, 王业清, 蒋 茜, 廖志新*
东南大学化学化工学院制药工程系, 南京 210009
【摘 要】 目的：对黑边假龙胆的化学成分进行研究。方法：应用硅胶柱色谱, Sephadex LH-20 和 Rp-18 反相柱色
谱的方法分离和纯化化合物, 通过光谱方法及理化性质鉴定化合物结构。结果：分离得到 9 个化合物, 分别鉴定为 1-羟基
-3, 7, 8-三甲氧基 酮(1)、1, 8-二羟基-3, 5-二甲氧基 酮(2)、木犀草素(3)、β-胡萝卜苷(4)、海波拉亭(5)、1-羟基-3, 5, 8-三
甲氧基 酮(6)、熊果酸(7)、雏菊叶龙胆(8)、木犀草素-5-O-β-D-葡萄糖苷(9)。结论：化合物 1~3、5~7、9 均首次从该种植
物中分离得到。
【关键词】 假龙胆属; 黑边假龙胆; 化学成分



·信 息·
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《中国天然药物》以学术质量为生命线, 国内外学术影响不断扩大, 据 2009 年《中国科技期刊引证报告(扩刊版)》
CSTJCR 统计, 本刊影响因子为 1.152, 五年影响因子 1.289, 基金论文比 74.5%, 即年指标 0.147, 被引率 58%, 各项指
标均居 65 种药学期刊第 2 位, 中国药学会期刊第 1 位, “思路与方法”栏目下载、浏览量逾 20 万篇次, 有极高的权
威性与学术影响力, 在高校、科研机构、制药企业拥有广泛的读者群。

(本刊编辑部)



2010 年 11 月 第 8 卷 第 6 期