Anacrotine, from Crotalaria incana

Journal of the Chemical Society C: Organic
1968.0

Abstract

Crotalaria incana, a shrub indigenous to North America, was reported by Adams and Van Duuren to contain integerrimine (I), an ester of retronecine (V). For this study, material from a single large C. incana shrub growing at the University of Natal (Pietermaritzburg), propagated vegetatively from cuttings originally from America, was used. Cuttings (wood, stems, leaves, and flowers) were collected between November 1964 and February 1965, warm-air dried, ground, and extracted with hot ethanol or methanol. The crude alkaloids (approximately 0.7% of the dried plant weight) yielded a new crystalline alkaloid, anacrotine (0.21–0.24% of the plant weight), instead of the expected integerrimine. Aqueous alkaline hydrolysis of anacrotine produced crotanecine (a new amino-alcohol) and senecic acid, both identical to authentic samples. Chemical analyses (including hydrogenation, elemental analysis, and derivative formation) and spectroscopic data (infrared) confirmed that anacrotine is a cyclic diester of senecic acid with crotanecine, and both anacrotine and crotanecine contain a 3-pyrroline ring. Thin-layer chromatography of the crude extract (after separating crystalline anacrotine) revealed one major and three minor alkaloids, all of which were esters of crotanecine (IV); no retronecine (V) was detected. Thus, all alkaloids from this C. incana specimen are esters of crotanecine, in contrast to the material studied by Adams and Van Duuren, which contained only integerrimine (an ester of retronecine). This significant variation in alkaloid composition among plants of the same species may result from differences in climate, nutrition, or the developmental stage at which the plants were harvested.

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