Obovamine, a New Indole Alkaloid fromStemmadenia obovata

Journal of Natural Products
1996.0

Abstract

The stem bark of the Panamanian plant Stemmadenia obovata has afforded a new ibogaine type alkaloid, obovamine (1), whose structure was determined by a combination of spectral interpretation and chemical correlations. Ten known alkaloids, coronaridine, coronaridine hydroxyindolenine, voacangine, voacangine hydroxyindolenine, (19S)-heyneanine, (19S)-heyneanine hydroxyindolenine, (19S)-voacristine, (19S)-voacristine hydroxyindolenine, ajmalicine, and ajmalicinine, were also isolated. Voacangine was the main alkaloid constituent. In a previous work, we reported the isolation of obovatine, bis[11-hydroxycoronaridin-12-yl]-11-hydroxycoronaridine, and voacristine from the leaves and N1 methyl-11-hydroxymacusine A from the stem bark of Stemmadenia obovata. Here we report the study of the organic-soluble stem bark fraction. The acidic and neutral crude alkaloidal fractions of the EtOH extract afforded the new iboga indolenine alkaloid obovamine (1) and the known alkaloids voacangine (2), voacangine hydroxyindolenine (3), coronaridine, coronaridine hydroxyindolenine (4), (19S)-heyneanine, (19S)-heyneanine hydroxyindolenine, (19S)-voacristine, (19S)-voacristine hydroxyindolenine, ajmalicine (5), and an epimeric mixture of ajmalicinine (6) and 17-epi-ajmalicinine (7). The known compounds were identified by comparison of their spectral data with those reported in the literature.

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