Chemistry of Natural Compounds, Vol. 46, No. 5, 2010
FLAVONOIDS FROM Salix caprea
M. Moohammadnor, X. Tursun,1
1
UDC 547.972
1
1*
M. Qiong Ling, A. Sultan,
and K. A. Eshbakova2
Salix caprea L. (Salicaceae) is widely used in folk medicine for rheumatoid arthritis, malaria, various hemorrhages,
gout, neuralgia, and intestinal diseases as an antipyretic, analgesic, anti-inflammatory, antibacterial, hemostatic, sedative, and
antihelminthic agent [1, 2].
Carbohydrates [3], tanning agents [4], steroids [5], phenolglucosides [6], alkaloids, vitamins [7], phenolcarboxylic
acids and their derivatives [8], flavonoids chultenin [3], kaempferol, luteolin, apigenin, naringenin, quercetin, isorhamnetin
[
9], luteolin 7-O-ꢀ-D-glucopyranoside, baccoside, salicaprin [10-12], diosmetin, caperoside, salicaperoside [13, 14], astragalin,
quercemeritrin, and quercetin 3,7-di-O-glucoside [15] were isolated from S. caprea.
Ground air-dried flowers of S. caprea (1000 g) that were collected in Hotan district of Xinjiang Autonomous Region,
P. R. China, were extracted exhaustively with EtOH (70%) at room temperature. The combined extracts were evaporated in
vacuo. The condensed residue was diluted with water and treated successively with petroleum ether, ether, EtOAc, and
n-BuOH.
The EtOAc fraction was separated by HPLC over a Phenomenex ODS-C18 column (250 ꢁ 4.6 mm, 5 ꢂm) with a C18
pre-column. Solvents were filtered through a 0.45 ꢂm filter before use. The mobile phase was MeOH:H O (40:60, v/v) at
2
flow rate 1 mL/min. UV detection was carried out at ꢃ 210, 260, 280, and 360 nm (at various recording scales I, II, III, IV).
Four compounds (1–4) were eluted from the column with retention times of 15, 43, 64, and 70 min, respectively.
Pure compounds were identified using UV, IR, PMR, and 13C NMR spectra as astragalin (1) [15, 16], quercimeritrin
(
2) [15, 17], isorhamnetin-7-O-ꢀ-D-glucoside (3) [18], and isoquercitrin (4) [19].
Astragalin (1), C H O , mp 177–179°C. UV spectrum (MeOH, ꢃ , nm): 268, 301, 360; +AlCl : 272, 304, 398;
2
1
20 11
max
3
+
AlCl /HCl: 277, 302, 350, 398; +CH COONa: 278, 370.
3
3
Acid hydrolysis of astragalin produced kaempferol and D-glucose.
Quercimeritrin (2), C H O , mp 251–253°C. UV spectrum (MeOH, ꢃ , nm): 260, 370; +CH COONa: 260,
1
2
20 12
max
3
3
71.
Acid hydrolysis of 2 produced quercetin and D-glucose.
Isorhamnetin-7-O-ꢀ-D-glucoside (3), C H O , mp 255–257°C. UV spectrum (MeOH, ꢃmax, nm): 257, 372;
2
2 22 12
+
CH COONa: 257, 374.
3
–
1
IR spectrum (KBr, ꢄ, cm ): 3308, 2929, 1656, 1604, 1511, 1456, 1432, 1358, 1291, 1262, 1205, 1183, 1126, 1025,
9
94.
PMR spectrum (400 MHz, DMSO-d , ꢅ, ppm, J/Hz, 0 = HMDS): 3.20-3.78 (6H, Glc), 3.83 (3H, s, OMe), 5.58 (1H,
6
d, J = 7.6, Glc H-1ꢆ), 6.20 (1H, d, J = 1.6, H-6), 6.43 (1H, d, J = 1.6, H-8), 6.90 (1H, d, J = 8.4, H-5ꢇ), 7.52 (1H, dd, J = 1.6, 8.8,
H-6ꢇ), 7.95 (1H, d, J = 1.6, H-2ꢇ), 12.60 (1H, s, 5-OH).
1
3
C NMR spectrum (100 MHz, DMSO-d , ꢅ, ppm): 156.46 (C-2), 132.97 (C-3), 177.30 (C-4), 162.18 (C-5),
6
9
(
5
8.82 (C-6), 164.65 (C-7), 93.81 (C-8), 156.20 (C-9), 103.83 (C-10), 121.12 (C-1ꢇ), 113.48 (C-2ꢇ), 149.32 (C-3ꢇ), 146.87
C-4ꢇ), 115.17 (C-5ꢇ), 122.01 (C-6ꢇ), 100.80 (C-1ꢆ), 74.27 (C-2ꢆ), 76.31 (C-3ꢆ), 69.73 (C-4ꢆ), 77.43 (C-5ꢆ), 60.73 (C-6ꢆ),
5.68 (OMe).
1
) Institute of Chemistry and Chemical Engineering of Xinjiang University, Urumqi, 830046, P. R. China,
e-mail: ayrat1959@yahoo.com.cn; 2) S. Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of
the Republic of Uzbekistan, Tashkent, fax: (99871) 120 64 75, e-mail: e_komila@yahoo.com. Translated from Khimiya
Prirodnykh Soedinenii, No. 5, pp. 673–674, September–October, 2010. Original article submitted March 29, 2010.
0
009-3130/10/4605-0799 ©2010 Springer Science+Business Media, Inc.
799
Moohammadnor
