全 文 ： 496 Journal of Chinese Pharmaceutical Sciences http://www.jcps.ac.cn
Flavonoids from Artemisia gmelinii Web. ex Stechm.
Wenzhi Zeng1, Quesheng2, Qingying Zhang1*, Hong Liang1*
1. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Sciences Center,
Beijing 100191, China
2. Department of Chemistry, Teachers College for Nationalities, Qinghai Normal University, Xining 810008, China
Abstract: Phytochemical investigation of Artemisia gmelinii Web. ex Stechm. led to the isolation of 11 known flavonoids. Their
structures were identified as genkwanin (1), hispidulin (2), 3-hydroxy-genkwanin (3), chrysoeriol (4), apigenin (5), 5,7,3,4-
tetrahydroxy-6,5-dimethoxy-flavone (6), kumatakenin (7), quercetin (8), patuletin (9), quercetagetin-3,6,7-trimethylether (10)
and 7,3,4-trihydroxy-3-methoxy-flavone (11) by spectroscopic methods. Ten compounds (2–11) were isolated from this title
plant for the first time, and five compounds (3, 6, 7, 10 and 11) were isolated from genus Artemisia for the first time.
Keywords: Flavonoids, Artemisia gmelinii Web. ex Stechm., Chemical constituents
CLC number: R284 Document code: A Article ID: 1003–1057(2014)7–496–04
Received: 2014-03-02, Revised: 2014-03-31, Accepted: 2014-04-15.
*Corresponding author. Tel.: 86-10-82801592,
E-mail: qyzhang@bjmu.edu.cn, lianghong@bjmu.edu.cn
http://dx.doi.org/10.5246/jcps.2014.07.065
1. Introduction
The genus Artemisia has been placed taxonomically
in the tribe Anthemideae of the family Asteraceae, with
186 species being distributed within mainland of China[1].
Artemisia gmelinii Web. ex Stechm., a perennial herb
belonging to the genus Artemisia, is widely distributed
in east and south Asia with several ethnopharmacological
applications. Food and medicines made from A. gmelinii
were used in Asia to treat skin disease, inflammatory
liver conditions, cold, cough, fever, boils and pimples[2].
Sesquiterpene lactones, flavonoids, coumarins and organic
acid derivatives have been reported in the plant[3,4].
Our current research on the constituents of A. gmelinii
resulted in the isolation of 11 known flavonoids (Fig. 1).
Ten compounds (2–11) were isolated from this title plant
for the first time, and five compounds (3, 6, 7, 10 and 11)
were isolated from this genus for the first time.
2. Experimental
2.1. General experimental procedures
1D and 2D NMR spectra were taken on a Bruker AV
400 spectrometer (Bruker, Fllanden, Switzerland) with


























tetramethylsilane (TMS) as the internal standard. HPLC
analysis was performed on an analytical HPLC system
(Shimadzu, Kyoto, Japan) consisting of an LC-10AVP
pump, a DGU-14A degasser, an SCL-10AVP system
controller, an SPDM10AVP diode-array detector, and
a Cosmosil ODS column (5 µm,4.6 mm×250 mm) with
1 R1 = H R2 = OCH3 R3 = H R4 = H
2 R1 = OCH3 R2 = OH R3 = H R4 = H
3 R1 = H R2 = OCH3 R3 = OH R4 = H
4 R1 = H R2 = OH R3 = OCH3 R4 = H
5 R1 = H R2 = OH R3 = H R4 = H
6 R1 = OCH3 R2 = OH R3 = OCH3 R4 = OH
7 R1 = OCH3 R2 = OH R3 = H R4 = OCH3 R5 = H
8 R1 = OH R2 = OH R3 = H R4= OH R5 = OH
9 R1 = OH R2 = OH R3 = OCH3 R4 = OH R5 = OH
10 R1 = OCH3 R2 = OH R3 = OCH3 R4 = OCH3 R5 = OH
11 R1 = OCH3 R2 = H R3 = H R4 = OH R5 = OH
Figure 1. Structures of compounds 1–11.
O
OH
R2
OH
R3
O
R1
R42
4
5
7
9
10
1
4
3
5
O
R2
R4
OH
R5
O
R3
2
4
5
7
9
10
1
4
3
R1
497 Zeng, W.Z. et al. / J. Chin. Pharm. Sci. 2014, 23 (7), 496–499
a flow rate of 1 mL/min. Thin layer chromatography
(TLC) and column chromatography (CC) were performed
on silica gel plates and silica gel (TLC: GF254 and CC:
200–300 mesh; Qingdao Marine Chemical Co., Ltd,
Qingdao, China), Sephadex LH-20 (GE Healthcare,
Uppsala, Sweden), and MDS-5-300 ODS gel (200–
300 mesh, Beijing Medicine Technology Center,
Beijing, China), separately. Solvents were of analytical
grade, which were purchased from Beijing Chemical
Corporation (Beijing, China). Fractions were monitored
by TLC, and spots were visualized on precoated silica
gel plates by spraying 1% vanillin in H2SO4 followed by
heating.
2.2. Plant materials
The whole plant of A. gemlinii was collected in
September 2010 in Yushu, Qinghai Province, China.
Species identification was confirmed by Prof. Skarmat-
sogsgnyis, Tibetan Medical College, Qinghai University,
Xining, China. A voucher specimen (FL2010101701) is
maintained in the Department of Natural Medicines,
School of Pharmaceutical Sciences, Peking University.
2.3. Extraction and isolation
The air-dried and powdered whole plants of A. gemlinii
(13 kg) were percolated exhaustively with 95% aqueous
EtOH and 50% aqueous EtOH at room temperature,
respectively. After evaporation of the solvent under
reduced pressure, the residues were mixed and suspended
in water and then successively partitioned with
petroleum ether, EtOAc and n-BuOH to afford 500 g,
500 g, and 700 g of extracts, respectively. The petroleum
ether extract (500 g) was subjected to silica gel CC and
eluted with gradient system of petroleum ether–acetone
(20:1 to 1:5, v/v) to give eight fractions (Fr. A–Fr. H).
Fr. E (27.0 g) was further separated on silica gel CC
eluted with petroleum ether–MeOH (10:1, v/v), and
then purified by Sephadex LH-20 CC eluted with
CHCl3–MeOH (1:1, v/v) to afford 1 (30 mg).
The EtOAc extract (500 g) was subjected to silica gel
CC and eluted with CHCl3–MeOH (10:0 to 0:10, v/v) to
give seven fractions (Fr. 1–Fr. 7). Fr. 3 (38 g) was
further separated on silica gel CC eluted with petroleum
ether–acetone (3:1 to 1:2, v/v) to give five fractions
(Fr. 3A–Fr. 3E). Fr. 3C (7.2 g) was subjected to ODS
CC (MeOH–H2O, 40:60–100:0, v/v), and then purified
by Sephadex LH-20 CC (MeOH–H2O, 80:20, v/v) to
afford 3 (20 mg), 4 (23 mg), 5 (15 mg) and 6 (12 mg).
Fr. 3D (4.2 g) was subjected to ODS CC (MeOH–H2O,
40:60–100:0, v/v) to get subfractions Fr. 3D1–Fr. 3D7).
Compounds 7 (8 mg) and 8 (10 mg) were obtained
by Sephadex LH-20 (MeOH–H2O, 80:20, v/v) from
subfractions Fr. 3D3 and Fr. 3D4. Compounds 9 (12 mg),
10 (7 mg) and 11 (5 mg) were obtained by Sephadex
LH-20 (MeOH–H2O, 80:20, v/v) from subfraction
Fr. 3D5. Compound 2 (10 mg) was separated from Fr. 6.
3. Identification
3.1. Genkwanin (1)
Yellow amorphous powder (MeOH); 1H NMR
(400 MHz, DMSO-d6) δ: 12.97 (1H, s, OH-5), 10.40
(1H, s, OH-4), 7.96 (2H, d, J 8.0 Hz, H-2,6), 6.94
(2H, d, J 8.0 Hz, H-3,5), 6.85 (1H, s, H-3), 6.77 (1H,
brs, H-8), 6.38 (1H, brs, H-6), 3.87 (3H, s, OCH3);
13C NMR (100 MHz, DMSO-d6) δ: 181.9 (C-4), 165.1
(C-7), 164.1 (C-2), 161.3 (C-4), 161.2 (C-9), 157.2
(C-5), 128.6 (C-2,6), 121.1 (C-1), 116.0 (C-3,5),
104.7 (C-10), 103.0 (C-3), 98.0 (C-6), 92.7 (C-8),
56.0 (OCH3). All these data were in good agreement
with those of genkwanin[5].
3.2. Hispidulin (2)
Yellow amorphous powder (MeOH); 1H NMR
(400 MHz, DMSO-d6) δ: 13.09 (1H, s, OH), 7.93 (2H,
d, J 8.8 Hz, H-2,6), 6.92 (2H, d, J 8.8 Hz, H-3,5),
6.79 (1H, s, H-8), 6.59 (1H, s, H-3), 3.75 (3H, s,
OCH3); 13C NMR (100 MHz, DMSO-d6) δ: 182.2 (C-4),
163.8 (C-2), 161.2 (C-4), 157.3 (C-7), 152.8 (C-5),
152.4 (C-9), 131.4 (C-6), 128.5 (C-2,6), 121.2 (C-1),
116.0 (C-3,5), 104.1 (C-10), 102.4 (C-3), 94.3 (C-8),
60.0 (OCH3). All these data were in good agreement
with those of hispidulin[6].
3.3. 3-Hydroxy-genkwanin (3)
Yellow amorphous powder (MeOH); 1H NMR
(400 MHz, DMSO-d6) δ: 12.99 (1H, s, OH-5), 7.45 (1H,
dd, J1 2.0 Hz, J2 8.0 Hz, H-6), 7.44 (1H, br s, H-2),
6.91 (1H, d, J 8.0 Hz, H-5), 6.73 (1H, s, H-3), 6.72
(1H, d, J 2.0 Hz, H-8), 6.36 (1H, d, J 2.0 Hz, H-6),
3.86 (3H, s, OCH3); 13C NMR (100 MHz, DMSO-d6)
498 Zeng, W.Z. et al. / J. Chin. Pharm. Sci. 2014, 23 (7), 496–499
δ: 181.8 (C-4), 165.1 (C-7), 164.2 (C-2), 161.2 (C-5),
157.2 (C-9), 149.8 (C-4), 145.7 (C-3), 121.4 (C-1),
119.1 (C-6), 115.9 (C-5), 113.5 (C-2), 104.6 (C-10),
103.0 (C-3), 97.9 (C-6), 92.5 (C-8), 56.0 (4-OCH3).
All these data were in good agreement with those of
3-hydroxy-genkwanin[7].
3.4. Chrysoeriol (4)
Yellow amorphous powder (MeOH); 1H NMR
(400 MHz, DMSO-d6) δ: 12.98 (1H, 5-OH), 7.57 (1H,
dd, J1 2.0 Hz, J2 8.8 Hz, H-6), 7.56 (1H, br s, H-2),
6.94 (1H, d, J 8.8 Hz, H-5), 6.91 (1H, s, H-3), 6.51
(1H, d, J 2.0 Hz, H-8), 6.20 (1H, d, J 2.0 Hz, H-6),
3.89 (3H, s, OCH3); 13C NMR (100 MHz, DMSO-d6)
δ: 181.8 (C-4), 164.1 (C-7), 163.7 (C-2), 161.4 (C-9),
157.3 (C-5), 150.7 (C-3), 148.0 (C-4), 121.5 (C-6),
120.3 (C-1), 115.7 (C-5), 110.2 (C-2), 103.7 (C-3),
103.2 (C-10), 98.8 (C-6), 94.0 (C-8), 55.9 (4-OCH3).
All these data were in good agreement with those of
chrysoeriol[5].
3.5. Apigenin (5)
Yellow amorphous powder (MeOH); 1H NMR
(400 MHz, DMSO-d6) δ: 12.98 (1H, s, OH-5), 7.94
(2H, d, J 8.8 Hz, H-2,6), 6.93 (2H, d, J 8.8 Hz, H-3,5),
6.80 (1H, s, H-3), 6.48 (1H, d, J 1.6 Hz, H-8), 6.19
(1H, d, J 1.6 Hz, H-6); 13C NMR (100 MHz, DMSO-d6)
δ: 181.8 (C-4), 164.1 (C-2), 163.8 (C-7), 161.5 (C-9),
161.2 (C-4), 157.3 (C-5), 128.5 (C-2,6), 121.2 (C-1),
116.0 (C-3,5), 103.7 (C-10), 102.9 (C-3), 98.9 (C-6),
94.0 (C-8). All these data were in good agreement with
those of apigenin[5].
3.6. 5,7,3,4-Tetrahydroxy-6,5-dimethoxy-flavone (6)
Yellow amorphous powder (MeOH); 1H NMR
(400 MHz, DMSO-d6) δ: 13.11 (1H, s, OH-5), 7.17 (1H,
d, J 1.6 Hz, H-6), 7.15 (1H, d, J 1.6 Hz, H-2), 6.84
(1H, s, H-3), 6.58 (1H, s, H-8), 3.89 (3H, s, OCH3),
3.76 (3H, s, OCH3); 13C NMR (100 MHz, DMSO-d6)
δ: 182.1 (C-4), 163.9 (C-2), 157.2 (C-9), 152.8 (C-5),
152.4 (C-7), 148.6 (C-5), 145.9 (C-3), 138.6 (C-4),
131.3 (C-6), 120.4 (C-1), 107.5 (C-2), 104.1 (C-10),
102.8 (C-3), 102.3 (C-6), 94.1 (C-8), 59.9 (5-OCH3),
56.2 (6-OCH3). All these data were in good agreement
with those of 5,7,3,4-tetrahydroxy-6,5-dimethoxy-
flavone[8].
3.7. Kumatakenin (7)
Yellow amorphous powder (MeOH); 1H NMR
(400 MHz, DMSO-d6) δ: 12.69 (1H, s, OH-5), 10.29
(1H, s, OH-4), 7.98 (2H, d, J 8.8 Hz, H-2,6), 6.96
(2H, d, J 8.8 Hz, H-3,5), 6.75 (1H, d, J 2.4 Hz, H-8),
6.38 (1H, d, J 2.4 Hz, H-6), 3.87 (3H, s, 3-OCH3),
3.80 (3H, s, 7-OCH3); 13C NMR (100 MHz, DMSO-d6)
δ: 178.5 (C-4), 165.1 (C-7), 160.9 (C-5), 160.3 (C-4),
156.3 (C-9), 155.8 (C-2), 137.8 (C-3), 130.2 (C-2,6),
120.4 (C-1), 115.6 (C-3,5), 105.2 (C-10), 97.7 (C-6),
92.3 (C-8), 59.3 (7-OCH3), 56.0 (3-OCH3). All these data
were in good agreement with those of kumatakenin[9].
3.8. Quercetin (8)
Yellow amorphous powder (MeOH); 1H NMR
(400 MHz, DMSO-d6) δ: 12.49 (1H, s, OH-5), 10.77,
9.58, 9.36, 9.30 (1H, s, OH), 7.68 (1H, d, J 2.0 Hz,
H-2), 7.53 (1H, dd, J1 2.0 Hz, J2 8.4 Hz, H-6), 6.87 (1H,
d, J 8.4 Hz, H-5), 6.39 (1H, d, J 2.0 Hz, H-8), 6.17 (1H, d,
J 2.0 Hz, H-6); 13C NMR (100 MHz, DMSO-d6) δ: 175.8
(C-4), 163.8 (C-7), 160.7 (C-9), 156.1 (C-5), 147.7
(C-4), 146.8 (C-2), 145.0 (C-3), 135.7 (C-3), 121.9
(C-1), 119.9 (C-6), 115.6 (C-5), 115.0 (C-2), 103.0
(C-10), 98.1 (C-6), 93.3 (C-8). All these data were in
good agreement with those of quercetin[5].
3.9 Patuletin (9)
Yellow amorphous powder (MeOH); 1H NMR
(400 MHz, DMSO-d6) δ: 12.57 (1H, s, OH-5), 7.67
(1H, J 2.0 Hz, H-2), 7.54 (1H, dd, J1 2.0 Hz, J2 8.4 Hz,
H-6), 6.88 (1H, d, J 8.4 Hz, H-5), 6.51 (1H, s, H-8),
3.75 (3H, s, OCH3); 13C NMR (100 MHz, DMSO-d6) δ:
176.0 (C-4), 157.2 (C-9), 151.7 (C-5), 151.3 (C-7), 147.7
(C-4), 146.9 (C-2), 145.0 (C-3), 135.4 (C-3), 130.8 (C-6),
121.9 (C-1), 120.0 (C-6), 115.6 (C-2), 115.0 (C-5),
103.3 (C-10), 93.6 (C-8), 60.0 (6-OCH3). All these data
were in good agreement with those of patuletin[10].
3.10. Quercetagetin-3,6,7-trimethylether (10)
Yellow amorphous powder (MeOH); 1H NMR
(400 MHz, DMSO-d6) δ: 12.66 (1H, s, OH-5), 7.60 (1H,
d, J 2.0 Hz, H-2), 7.50 (1H, dd, J1 2.0 Hz, J2 8.4 Hz,
H-6), 6.92 (1H, d, J 8.4 Hz, H-5), 6.80 (1H, s, H-8),
3.92 (3H, s, 7-OCH3), 3.80 (3H, s, 3-OCH3), 3.73 (3H,
s, 6-OCH3); 13C NMR (100 MHz, DMSO-d6) δ: 178.2
(C-4), 158.6 (C-7), 156.0 (C-2), 151.7 (C-5), 151.7 (C-9),
499 Zeng, W.Z. et al. / J. Chin. Pharm. Sci. 2014, 23 (7), 496–499
148.8 (C-4), 145.2 (C-3), 137.7 (C-3), 131.6 (C-6), 120.7
(C-1), 120.6 (C-6) 115.7 (C-2), 115.5 (C-5), 105.5
(C-10), 91.2 (C-8), 60.1 (6-OCH3), 59.7 (3-OCH3), 56.5
(7-OCH3). All these data were in good agreement with
those of quercetagetin-3,6,7-trimethylether[11].
3.11. 7,3,4-Trihydroxy-3-methoxy-flavone (11)
Yellow amorphous powder (MeOH); 1H NMR
(400 MHz, DMSO-d6) δ: 10.78, 9.68, 9.37 (each 1H,
s, OH), 7.90 (1H, d, J 8.4 Hz, H-5), 7.55 (1H, d, J 1.6 Hz,
H-2), 7.44 (1H, dd, J1 1.6 Hz, J2 8.4 Hz, H-6), 6.90
(2H, d, J 8.4 Hz, H-5,6), 6.89 (1H, br s, H-8), 3.77
(3H, s, OCH3); 13C NMR (100 MHz, DMSO-d6) δ:
154.5 (C-2), 139.3 (C-3), 173.0 (C-4), 126.6 (C-5),
115.6 (C-6), 162.4 (C-7), 102.0 (C-8), 156.3 (C-9),
116.3 (C-10), 121.3 (C-1), 115.4 (C-2), 145.1 (C-3),
148.2 (C-4), 114.7 (C-5), 120.3 (C-6), 59.3 (OCH3).
All these data were in good agreement with those of
7,3,4-trihydroxy-3-methoxy-flavone[12].
Acknowledgements
The authors are grateful to Prof. Skarmatsogsgnyis
(Tibetan Medical College, Qinghai University, Xining,
China) for identifying the plant material.
References
[1] Chinese academy of sciences, China flora editorial board.
Flora of China, Science Press, 1991, 2.
[2] Árpád, K.; Zoltán, B.; Márta, M.S.; Attila, R.; Viktor, H.;
Judit, H.; Imre, M.; Csaba, S.J.; György, M.K.; György
T.B. J. Pharm. Biol. 2012, 56, 83−89.
[3] Jia, M.; Li, X. Chin. Ethn. Med. China Medical Science
Press, 2005, 67.
[4] Wu, C.; Tu, Y. Chin. Bull. Bot. 1985, 3, 34−37.
[5] Hildebert, W.; Vedantha, M.C. Tetrahedron Lett. 1976,
21, 1799−1804.
[6] Liu, Y.L.; David, K.H.; John, M.C. J. Nat. Prod. 1992,
55, 357−363.
[7] Song, L.L.; Li, X.; Yan, P. Chin. Herb. Med. 2010, 41,
536−538.
[8] Macro, J.A.; Barbera, O.; Rodriguez, S.; Domingo, C.;
Adell, J. Phytochemistry. 1988, 27, 3155−3159.
[9] Zhang, X.Y.; Li, B.G.; Zhou, M. Chin. J. Appl. Enviro.
Biol. 2006, 12, 338−341.
[10] Masakazu, A.; Tetsuya, K.; Toshio, K. Phytochemistry.
1986, 25, 231−233.
[11] Fu, D.; Zou, L.; Yang, X. Nat. Prod. Res. Dev. 2008,
20, 265−268.
[12] Wu, J.H.; Tung, Y.T.; Shin, C.; Sheng, Y. J. Agric.
Food Chem. 2008, 56, 1567−1573.
细裂叶莲蒿黄酮类成分研究
曾文之1, 确生2, 张庆英1*, 梁鸿1*
1. 北京大学医学部 天然药物及仿生药物国家重点实验室, 药学院, 北京 100191
2. 青海师范大学 民族学院, 青海 西宁 810008 
摘要: 从细裂叶莲蒿 (Artemisia gmelinii Web. ex Stechm.) 的全草中分离得到11个已知黄酮类化合物。通过波谱技术
其结构分别鉴定为芫花黄素 (1), 高车前素 (2), 3-羟基芫花素 (3), 金圣草黄素 (4), 芹菜素 (5), 5,7,3,4-四羟基-6,5-二甲
氧基黄酮 (6), 华良姜素 (7), 槲皮素 (8), 万寿菊素 (9), 万寿菊黄素-3,6,7-三甲醚 (10)和7,3,4-三羟基-3-甲氧基黄酮 (11)。
10个化合物(2−11)为首次从细裂叶莲蒿中分离得到, 其中5个化合物 (3, 6, 7, 10和11)为首次从蒿属植物中分离得到。
关键词: 黄酮; 细裂叶莲蒿; 化学成分