Microbial transformations of natural antitumor agents. VIII. Formation of 8- and 9-hydroxyellipticines

Microbial transformations of ellipticine with Aspergillus alliaceus (NRRL 315) yielded two phenolic metabolites which were isolated and characterized as 8- and 9-hydroxyellipticines. The latter is a major metabolite and its structure was determined by NMR and mass-spectometric analyses, and by comparison with authentic 9-hydroxyellipticine prepared by chemical demethylation of 9-methoxyellipticine. The structure of 8-hydroxyellipticine was determined primarily by NMR spectrometry. Whereas 8-hydroxyellipticine is a new derivative, 9-hydroxyellipticine has been described, and it is one of the major mammalian metabolites of the antitumor alkaloid ellipticine.