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Vindoline (1a ) was transformed toO -demethylvindoline (1b ) bySepedonium chrysospermum ATCC 13378 in 33% yield. Thin-layer and high-pressure liquid chromatographic methods distinguished1b from previously reported microbial metabolites of vindoline. The structural proof of1b was based on its mass spectral fragmentation pattern and on its chemical and nuclear magnetic resonance spectral properties.

Microbial Transformations of Natural Antitumor Agents: O -Demethylation of Vindoline by Sepedonium chrysospermum