Chemistry of Natural Compounds, Vol. 38, No. 3, 2002
B R I E F C O M M U N I C A T I O N S
FLAVONOIDS OF THE AERIAL PART OF
M. P. Yuldashev
Trigonella grandiflora
UDC 547.972
Plants of the
L. (Fabaceae) genus are rich sources of flavonoids and saponins. Certain species are used in
Trigonella
folk medicine as diuretics, analgesics, and antitumor agents for gout, ascites, and epilepsy [1, 2].
Bge is an annual that grows on dry stony and gravelly slopes, in arid lands, in cultivation, and in fields
T. grandiflora
in the lower mountainous band of Central Asia [3].
Ground and air-dried raw material (2.0 kg) collected during flowering (April 24, 1997) in the vicinity of the Alimtau
mountains (Chimkentsk region, Republic of Kazakhstan) was exhaustively extracted with ethanol at room temperature. The
combined extract was evaporated in vacuo. The condensed remainder was diluted with water and successively treated with
CHCl , ethylacetate, and -butanol. The solvents were removed to yield CHCl (46.0 g), ethylacetate (22.0 g), and butanol
n
3
3
(43.0 g) fractions.
The ethylacetate fraction was chromatographed over a silica-gel column with elution by CHCl —CH OH (97:3—85:15)
3
3
to give 1-5.
The butanol fraction was chromatographed over a silica-gel column with elution by CHCl —CH OH (90:10—85:15)
3
3
to isolate flavonoids 6 and 7.
The isolated compounds were identified using PMR, UV, and mass spectra in addition to chemical transformations
and direct comparison with authentic samples of certain compounds.
+
Biochanin A (1) (5,7-dihydroxy-4′-methoxyisoflavone), C16H12O5, [M] 284, mp 213-214°C. UV spectrum (EtOH,
λmax, nm) 263, 335. According to the UV spectrum, 1 is an isoflavone derivative. The PMR spectrum (100 MHz, C D N, δ,
5
5
ppm, J/Hz) contains signals at 3.63 (3H, s, OCH ), 6.55 (1H, d, J = 2.0, H-6), 6.63 (1H, d, J = 2.0, H-8), 6.96 (2H, d, J = 9.0,
3
H-3′,5′), 7.62 (2H, d, J = 9.0, H-2′,6′), 8.05 (1H, s, H-2) [4].
+
Luteolin (2) (5,7,3′,4′-tetrahydroxyflavone), C15H10O6, [M] 286, mp 328-330°C (dec.). UV spectrum (EtOH, λmax
,
nm) 260, 274, 356 [5, 6].
Quercetin (3) (3,5,7,3′,4′-pentahydroxyflavone), C15H10O7, [M] 302, mp 313-315°C. UV spectrum (EtOH, λmax, nm)
257, 267, 371 [6, 7].
+
Cinaroside (4) (luteolin-7-O-β-D-glucoside), C21H20O11, mp 240-242°C (dec.). UV spectrum (EtOH, λmax, nm) 256,
268, 350; +CH COONa 259, 267, 363, 403; +CH COONa/H BO 259, 373; +AlCl 274, 299, 330, 430; +AlCl /HCl 272, 293,
3
3
3
3
3
3
356, 386; +CH ONa 262, 301, 392. According to the UV spectrum, 4 is a flavone derivative.
3
The PMR spectrum (100 MHz, C D N, δ, ppm, J/Hz) contains signals at 3.90-4.05 (sugar protons), 5.66 (1H, d,
5
5
J = 7.0, H-1″), 6.67 (1H, d, J = 2.5, H-6), 6.77 (1H, s, H-3), 6.84 (1H, d, J = 2.5, H-8), 7.13 (1H, d, J = 8.0, H-5′), 7.38 (1H, dd,
J = 8.0 and J = 2.5, H-6′), 7.74 (1H, d, J = 2.5, H-2′).
Acid hydrolysis of 4 produced luteolin and D-glucose. Acetylation of 4 by acetic anhydride in pyridine gave the
+
heptaacetyl derivative of composition C35H34O18 ([M] 742), mp 121-123°C [5, 6].
Quercetin-7-O-β-D-glucopyranoside (5), C21H20O12, mp 245-247°C, UV spectrum (EtOH, λmax, nm) 257, 266, 374;
+CH COONa 256, 267, 378.
3
The PMR spectrum (100 MHz, C D N, δ, ppm, J/Hz) contains signals at 3.87-4.60 (glucose protons), 5.73 (1H, d,
5
5
J = 6.5, H-1″), 6.69 (1H, d, J = 2.5, H-6), 6.91 (1H, d, J = 2.5, H-8), 7.25 (1H, d, J = 8.5, H-5′), 7.96 (1H, dd, J = 2.5 and
J = 8.5, H-6′), 8.50 (1H, d, J = 2.5, H-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. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 243-244, May-June, 2002.
Original article submitted May 13, 2002.
0009-3130/02/3803-0291$27.00 ©2002 Plenum Publishing Corporation
291
Yuldashev
