Lycoris Alkaloids. XXIV. : Isolation and Characterization of Lycoremine.

Pharmaceutical Bulletin
1953.0

Abstract

A number of alkaloids are contained in the bulb of Lycoris radiata Herb. Morishima (1897) reported the isolation of two bases, lycorine and sekisanine, and later Kondo and collaborators added seven new members. Through the kindness of Prof. H. Kondo in providing crude materials, the authors undertook further studies to isolate new alkaloids. A new minor alkaloid, lycoremine, was obtained by the partial extraction method using dilute hydrochloric acid. Its properties were characterized: m.p. 127~129°, molecular formula C₁₇H₂₁O₃N, presence of one O-methyl and one N-methyl group (revealed by Zeisel and Herzig-Meyer determination), tertiary amine (forming methiodide easily, no Liebermann's reaction for secondary amines), no carbonyl group (no carbonyl band in 5~6μ region of infrared spectrum), ultraviolet absorption maximum at 283 mμ (log ε=3.21) suggesting a methoxyl-substituted benzenoid ring, one alcoholic hydroxyl group (forming monoacetate with acetic anhydride and anhydrous sodium acetate). Hydrogenation of lycoremine in the presence of palladized charcoal gave lycoramine (main product, m.p. 120~121°, confirmed by mixed melting point with authentic specimen) and a small amount of an oily isomer. The authors found that lycoramine is represented by C₁₇H₂₃O₃N rather than the previously assigned C₁₇H₂₅O₃N, and reinvestigation of the structure of lycoramine is in progress.

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