Folimine — A new alkaloid from Haplophyllum foliosum

Chemistry of Natural Compounds
1972.0

Abstract

Continuing a study of the alkaloids of the epigeal part of H. foliosum Vved., the combined chloroformic alkaloids were separated into phenolic and nonphenolic fractions. The water-soluble nonphenolic mixture (22 g) yielded foliosidine (18 g) upon treatment with acetone. The remainder was chromatographed on alumina, and the ethereal eluates yielded skimmianine, N-methyl-2-phenyl-4-quinolone, foliosine, and a new alkaloid (mp 139-140°C, benzene-petroleum ether; hydrochloride mp 171-172°C; picrate mp 193-194°C) named folimine. Spectroscopic analysis (UV, IR, mass, NMR) suggested folimine's structure as 4,8-dimethoxy-N-methyl-2-quinolone, which was confirmed by methylating the previously isolated alkaloid folifidine to produce O-methylfolifidine, identical to folimine.

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