Chemistry of Natural Compounds, Vol. 41, No. 1, 2005
FLAVONOIDS FROM THE AERIAL PART OF Vicia subvillosa
M. P. Yuldashev
UDC 547.972
Plants of the Vicia L. (Fabaceae) genus are rich sources of flavonoids, anthocyans, carotinoids, and vitamins. Certain
of them are used in folk medicine for ascites, paralysis, epilepsy, and flu. The seeds are used as feed for pets and birds [1, 2].
Vicia subvillosa (Ledeb.) Trautv. is a perennial that grows on steppes and rarely on alkaline soils and in the foothills
of Central Asia [3].
Ground air-dried raw material (1.0 kg) that was collected during flowering (April 24, 1997) near the Alimtau
mountains (Chimkent district, Republic of Kazakhstan) was exhaustively extracted with ethanol. The combined extract was
evaporated in vacuo. The condensed residual was diluted with water and treated successively with CHCl , ethylacetate, and
3
n-butanol. The solvents were removed to afford CHCl (20.5 g), ethylacetate (14.0 g), and butanol (25.0 g) fractions.
3
The ethylacetate fraction was chromatographed over a silica-gel column using CHCl :CH OH (97:3-85:15) to
3
3
afford 1-4.
The compounds were identified using UV, IR, mass, and PMR spectral data in addition to chemical transformations
and comparison with authentic specimens.
+
Apigenin (1) (5,7,4′-trihydroxyflavone), C H O , 270 [M] , mp 347-348°C. UV spectrum (EtOH, λmax, nm): 270,
15 10 5
3
11.
PMR spectrum (100 MHz, δ, ppm, J/Hz, C D N): 6.61 (1H, d, J = 2.0, H-6), 6.73 (1H, d, J = 2.0, H-8), 6.81 (1H, s,
5
5
H-3), 7.08 (2H, d, J = 9.0, H-3′,5′), 7.85 (2H, d, J = 9.0, H-2′,6′), 13.67 (1H, br.s, 5-OH) [4, 5].
+
Luteolin (2) (5,7,3′,4′-tetrahydroxyflavone), C H O , 286 [M] , mp 328-330°C (dec.). UV spectrum (EtOH,
1
5 10 6
λmax, nm): 260, 270, 356.
IR spectrum: 3450-3300 cm-1 (OH), 1658 (γ-pyrone carbonyl), 1612, 1584 (aromatic C=C).
PMR spectrum (100 MHz, δ, ppm, J/Hz, C D N): 6.58 (1H, d, J = 2.0, H-6), 6.69 (1H, d, J = 2.0, H-8), 6.78 (1H, s,
5
5
H-3), 7.09 (1H, d, J = 8.0, H-5 ′), 7.53 (1H, br.s, H-2 ′), 7.60 (1H, dd, J = 2.0, J = 8.0, H-6 ′).
Acetylation of luteolin by acetic anhydride with pyridine produced the tetraacetate with mp 224-226°C, 454 [M]+
[4, 6].
+
Quercetin (3) (3,5,7,3′,4′-pentahydroxyflavone), C H O , 302 [M] , mp 313-314°C. UV spectrum (EtOH,
1
5 10 7
λmax, nm): 257, 268, 371; +CH COONa, 270, 406.
3
PMR spectrum (100 MHz, δ, ppm, J/Hz, C D N): 6.54 (1H, d, J = 2.5, H-6), 6.60 (1H, d, J = 2.5, H-8), 7.25 (1H, d,
5
5
J = 8.5, H-5 ′), 7.95 (1H, dd, J = 8.5, J = 2.5, H-6 ′), 8.45 (1H, d, J = 2.5, H-2 ′), 11.78 (1H, br.s, 3-OH), 13.75 (1H, br.s, 5-OH)
4, 6].
[
Cinaroside (4) (luteolin-7-O-β-D-glucopyranoside), C H O , mp 240-242°C (dec.). UV spectrum (EtOH,
21 20 11
λmax, nm): 256, 268, 350.
-1
IRspectrum: 3480-3300cm (OH), 1665( -pyran carbonyl), 1560, 1510(aromaticC=C), 1095, 1030(glycosideC–O).
PMR spectrum (100 MHz, , ppm, J/Hz, C D N): 3.92-4.07 (sugar protons), 5.54 (1H, d, J = 7.0, H-1′, D-glucose
5
5
anomeric proton), 6.68 (1H, d, J = 2.5, H-6), 6.79 (1H, s, H-3), 6.83 (1H, d, J = 2.5, H-8), 7.15 (1H, d, J = 8.0, H-5′), 7.40 (1H,
dd, J = 8.0, J = 2.5, H-6′), 7.72 (1H, d, J = 2.5, H-2′).
Acid hydrolysis of 4 produced luteolin and D-glucose. Acetylation of 4 with acetic anhydride and pyridine gave the
+
heptaacetyl derivative C H O , 742 [M] , mp 121-123°C [4, 6, 7].
3
5 34 18
Compounds 1-4 were isolated from V. subvillosa for the first time.
S. Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan,
Tashkent, fax (99871) 120 64 73. Translated from Khimiya Prirodnykh Soedinenii, No. 1, p. 80, January-February, 2005.
Original article submitted November 29, 2004.
©
0
009-3130/05/4101-0099 2005 Springer Science+Business Media, Inc.
99
Yuldashev
