Sesquiterpene lactones fromPyrethrum pyrethroides

SESQUITERPENE LACTONES FROM Pyrethrum pyrethroides B. Kh. Abduazimov, A. I. ¥unusov, and G. P.. Sidyakin UDC 547.314+582.998 The epigeal part of the plant Pyrethrum pyrethroide8 (Kar. et Kir.) B. Fedtsch, ex Krasch. [i], gathered in the period of full flowering on the Hisser range (TadzhSSR) in July 1980 was extracted with chloroform (1:5). The concentrated extract was treated with 40% aqueous ethanol. After filtration, the lactones were extracted from the aqueous ethanolic solution with chloroform. The chloroform extract was separated by chromatography on alumina (1:30). The substances were eluted by the solvent system petroleum ether-ethyl acetate (9:1). Fractions with a volume of 700 ml were collected, and fractions 13-22 and 35-36 crystallized on standing. On recrystallization from hexane--ethyl acetate, fractions 13-22 yielded a substance with mp 187°C, composition ClTH220s, Rf 0.38 (Silufol UV-254 plates; benzene-methanol (9:1) system). Its IR spectrum (KBr) contained absorption bands at (cm -~) 3520 (hydroxy group), 1755 and 1670 (a,8-unsaturated y-lactone), and 1740 and 1260 (ester group). All these facts, and also the color of the spot on spraying with sulfuric acid containing 1% of vanillin, recall the properties of cumambrin A [2, 3], and this was confirmed by direct comparison with an authentic sample [4]. When fractions 35 and 36 were recrystallized from hexane-~thyl acetate, colorless crystals deposited with mp 178-179°C, composition C15H=oO~, Rf 0.24. The IR spectrum had the absorption band of a hydroxy group (3500 cm-1), and also of an a,8-unsaturated y-lactone (1745 and 1670 cm-*). On acetylation with acetic anhydride in pyridine, this substance formed the first substance (the IR spectra and melting points were identical). Consequently, the second lactone was cumambrin B [2, 3]. This is the first time that these lactones have been obtained from this plant. LITERATURE CITED 1. 2, 3. 4. Flora of the USSR [in Russian], Moscow-Leningrad, Vol. XXVl (1961), p. 256. J. Romo de Vivar and F. A. Dias, Tetrahedron, 24, 5625 (1968). M. A. Irwin and T. A. Geissman, Phytochemistry, 8, 305 (1969), A. I. Yunusov, G. P. Sidyakin, and D. Kurbanov, Khim, Prir. Soedin., 655 (1978). Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 649-650, SeptemberOctober, 1983. Original article submitted May 18, 1983. 0009-3130/83/1905- 0617507.50 © 1984 Plenum Publishing Corporation 617  (...truncated)