Microbial transformations of natural antitumor agents: O-demethylation of vindoline by Sepedonium chrysospermum

Vindoline (1a) was transformed to O-demethylvindoline (1b) by Sepedonium chrysospermum ATCC 13378 in 33% yield. Thin-layer and high-pressure liquid chromatographic methods distinguished 1b from previously reported microbial metabolites of vindoline. The structural proof of 1b was based on its mass spectral fragmentation pattern and on its chemical and nuclear magnetic resonance spectral properties.