Conversion of nicotine to nornicotine in harvested tobacco: Fate of the methyl group

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Abstract
The metabolic conversion of nicotine to nornicotine by a converter strain of cigar tobacco has been investigated with the aid of randomly and specifically C14-labeled nicotines. The experiments represent an attempt to trace the fate of the methyl group during the demethylation of nicotine in detached leaves of tobacco. It was found that the conversion occurs only under aerobic conditions and that the N-methyl carbon of nicotine is oxidized to CO2. The data do not permit a choice of the mechanism for the initial steps of the reaction but do show that the overall course follows an oxidative pathway. Incidental observations allowed the conclusion that the methyl group of nicotine can supply C to other metabolic pools such as serine, choline, lignin and to a few unidentified compounds.