Sitosterol and triterpenoids fromAncathia igniaria

SITOSTEROL AND TRITERPENOIDS FROM Ancathia igniaria S. M. Adekenov, M. A. Abdykalykov, A. Zh. Turmukhambetov, and G. M. Kadirberlina UDC 547.819:547.918 Ancathia ingiaria Pall. ex Spreng. is a perennial plant of the family Asteraceae growing widely on the territory of Kazakhstan. The chemical composition of this plant has not previously been studied. From the flowerheads and leaves of A. i ~ i ~ i a gathered in the Bakhty mountains, Karaganda province, KazSSR, by extraction with chloroform followed by chromatography of the total material so obtained on a column of type KSK silica gel (ratio of the total material to support 1:20) with petroleum ether--benzene (9:1, 4:1, and I:i), four crystalline substances (IIV) have been isolated: I) C2gH560, mp 136-138°C, [~]D --36.5°; II) C3oH5o0, 198-200°C, [a] D +90°; III) C3oHsoO, mp 212-214°C; IV) C3oH~oO, mp 217-218°C, [~]D +51°" By comparing the physicochemical constants obtained and the results of IR and PMR spectroscopy with literature information [1-4] and directly with authentic samples on a Chrom-5 chromatograph (sorbent SE-30, carrier gas nitrogen), substances (1)-(IV) were identified as B-sitosterol, B-amyrin, lupeol, and taraxasterol, respectively. The roots of A. i~iaria were extracted with hot acetone in a Soxhlet apparatus. The resin obtained after the evaporation of the solvent was chromatographed on a column of type KSK silica gel at a ratio of the total material to support of 1:20. When the column was eluted with petroleum ether and with petroleum--benzene (9:1, 4:1, and i:i), ~-sitosterol and three crystalline substances (V-VII) were isolated: V) C32H520=, mp 246-247°C, [~]D +81"0°, Vl) C3=H5202, mp 206-207 ° , [aiD +38°; VII) C32Hs202, mp 237-240°C, [aid +103°; these were identified, respectively, as the acetates of B-amyrin, of lupeol, and of taraxasterol from their physicochemical constants, the results of elementary analyses, their IR and PMR spectra, and by the acetylation of (If-IV). B-Amyrin, lupeol, and taraxasterol acetate possess growth-regulating activity in relation to cell cultures of higher plants. B-sitosterol is a growth regulator of the dwarf pea [5]. LITERATURE CITED io 2. 3. , 5. A. Ulubelen and G. M. Brieskora, Planta Med., 31, No. i, 80 (1977). K. S. Mukherjee, Curr. Sci. (India), 48, No. 3, 197 (1979). P. W. LeQuense, S. B. Levery, M. D. Menachery, T. F. Brennan, and R. Raffauf, J. Chem. Perkin Trans., No. 12, 1572 (1978). T. Ames, J. Beton, A. Bowers, T. Halsall, and E. Jones, J. Chem. Soc., 1905 (1954). J. Kopcewicz, Naturwissenschaften, 56, 287 (1969). Institute of Organic Synthesis and Coal Chemistry of the Central Kazakhstan Division of Kazakhstan SSR Academy of Sciences, Karaganda. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 766-?67, SeptemberrOctober, 1987. Original article submitted March 16, 1987. 642 0009-3130/87/2305-0642512.50 © 1988 Plenum Publishing Corporation  (...truncated)