Biotransformations of several structurally related cinchona alkaloids were investigated, mimicking mammalian metabolism. Quinine was oxidized to the 1-N-oxide and 1′-N-oxide by Microsporum gypseum, whereas Cunninghamella echinulata yielded the known 3-hydroxy-quinine. Xylaria digitata and Mycobacterium smegmatis oxidized the 1-N of quinidine whereas Mycobacterium gypseum formed the 1-N-oxide of hydroquinidine. No microorganism was found to attack cinchonine. The 1-N-oxide of cinchonidine was obtained with Pellicularia filamentosa. The so far unknown 3-hydroxy-cinchonidine was formed by Rhizopus arrhizus ATTC 10260 and ATCC 11145. As the metabolites could be isolated in yields of up to 9%, these biotransformations offer a method for preparative use.
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Siebers-Wolff et al. (1993) studied this question.
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