Flavonoids from Climacoptera subcrassa
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FLAVONOIDS FROM Climacoptera subcrassa
A. K. Kipchakbaeva,1 B. K. Eskalieva,1* G. Sh. Burasheva,1 and H. A. Aisa2
UDC 547.972
Plants of the genus Climacoptera (23 species) (Chenopodiaceae) grow widely over the Republic of Kazakhstan (14 species). We studied previously four species of plants from this genus. Narcissin and hyperin were isolated from C. lanata and C. aralensis. These flavonoids were absent in plants of the species C. subcrassa. Therefore, the study of the chemical composition of Kazakhstan species of plants from the genus Climacoptera and the development of methods for isolating biologically active compounds in order to prepare new drugs and phytopreparations are timely [1–5]. We studied the aerial part of C. subcrassa collected during flowering in 2010 in Almaty Region. An analysis of the constituents detected phenolic and amino acids; flavonoids; saponins; mono-, oligo- and polysaccharides; steroids; and traces of coumarins [6]. Ground aerial part of air-dried plant (3 kg) was extracted (2u) with aqueous MeOH (70%) at room temperature for 3 d. The combined extract was concentrated and extracted successively with CHCl3, EtOAc, and n-BuOH. Column chromatography over silica gel with elution by CHCl3:EtOAc (8:2) isolated from the CHCl3 concentrate compound 1; from the EtOAc fraction (eluent CHCl3:EtOAc, 1:1, 1:2), compounds 2, 3, and 4. Based on physicochemical data and a comparison with the literature, the isolated compounds were identified as follows. Rhamnazin, 7,3c-dimethoxy-3,5,4c-trihydroxyflavone (1) [7] (10 mg), C17H14O7, mp 212–214°C, MeOH, lightyellow crystals, m/z [M]+ 329. UV spectrum (EtOH, Omax, nm): 360, 274, 254 (log H 4.7, 3.2, 4.54); (+NaOEt + H3BO3): 362, 272, 254; (+NaOEt): 402, 298, 274; (+AlCl3): 400, 302, 270; (+AlCl3 + HCl): 396, 290, 273; (+NaOAc): 362, 274, 256. IR spectrum (KBr, Q, cm1): 3400 (OH), 2960 (OCH3), 1660 (C=O), 1570, 1515 (C=C). PMR spectrum (400 MHz, CD3OD, G, ppm, J/Hz): 3.77 (3H, s, OMe), 3.89 (3H, s, OMe), 6.16 (1H, d, J = 2.4, H-6), 6.30 (1H, d, J = 2.4, H-8), 6.84 (1H, d, J = 9, H-5c), 7.56 (1H, dd, J = 2.4, 9, H-6c), 7.9 (1H, d, J = 2.4, H-2c). 5,7,4c-Trihydroxy-3c-methoxyflavone 3-O-D-L-rhamnopyranoside (2) [8] (20 mg), C22H22O12, mp 232–234°C, 20 80.0° (c 0.1, MeOH:H O), R 0.68 (BAW), 0.34 (6% CH CO H). UV spectrum MeOH, yellow crystals, m/z [M]+ 477, [D]D 2 f 3 2 (EtOH, Omax, nm): 355, 294, 255 (log H 4.22, 3.08, 4.18); (+NaOEt + H3BO3): 354, 260; (+NaOEt): 394. 272; (+AlCl3): 402, 302, 273; (+AlCl3 + HCl): 396, 300, 273; (+NaOAc): 406, 322, 274. IR spectrum (KBr, Q, cm1): 3400 (OH), 2980 (OCH3), 1640, 1620 (C=O), 1570, 1515 (C=C), 1090, 1060, 1020 (sugar pyranose form), 840 (D-form). PMR spectrum (400 MHz, CD3OD, G, ppm, J/Hz): 1.1 (3H, d, J = 7.5, CH3-rhamnose), 3.9 (3H, s, OMe), 5.2 (1H, d, H-1cc), 6.20 (1H, d, J = 2.5, H-6), 6.40 (1H, d, J = 2.5, H-8), 6.91 (1H, d, J = 10.5, H-5c), 7.62 (1H, dd, J = 10.5, 2.5, H-6c), 7.93 (1H, d, J = 2.5, H-2c). 5,4c-Dihydroxy-7,3c-dimethoxyflavone 3-O-E-D-glucopyranoside (3) [8] (10 mg), C23H24O12, mp 162–164°C,
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