Alkaloids of Guatteria melosma and Cleistopholis patens

Journal of Natural Products
1982.0

Abstract

Fractionation and chromatography of an ethanol extract of the stembark of Guatteria melosma Diels (Annonaceae) afforded the new noraporphine alkaloid, 3-hydroxynornuciferine (1) and its corresponding oxoaporphine alkaloid, isomoschatoline (2). The latter alkaloid was also isolated from an ethanol extract of the stembark of Cleistopholis patens Engl. & Diels (Anonaceae). The structure of 3-hydroxynornuciferine (1,2-dimethoxy-3-hydroxynoraporphine) (1) was confirmed by a consideration of its spectral data and that obtained on its N,O-diacetyl (5) and N-methyl (6) derivatives. The latter derivative was identical (ir, 1H-nmr, ma, [α] d) to 3-hydroxynuciferine (6). A consideration of the spectral data of isomoschatoline (2), its O-methyl (8) and O-acetyl (9) derivatives indicated that the alkaloid was 1,2-dimethoxy-3-hydroxyoxoaporphine. Reduction and subsequent acetylation of the alkaloid afforded a product that was identical (ir, 1H-nmr, ms) to N,O-diacetyl-3-hydroxynornuciferine (5). In addition, the morphinandienone alkaloid, pallidine (3) was isolated from G. melosma; the oxoaporphine alkaloid, liriodenine (4) was isolated from both G. melosma and C. patens; and an uncharacterized alkaloid, CPA 1, was isolated from C. patens. © 1982, American Chemical Society. All rights reserved.

Knowledge Graph

Similar Paper