Microbial transformation of N-methylcolchiceinamide

Seventy-seven microorganisms were examined for their ability to metabolize the antineoplastic agent N-methylcolchiceinamide, an analog of colchicine. Five streptomycetes exhibited significant metabolism, and Streptomyces griseus NRRL B-599 completely converted the substrate to three metabolites. In preparative-scale studies, N-dealkylation resulted in the production of colchiceinamide, the major metabolite (65%), which was characterized by chemical, spectroscopic, and chromatographic comparisons with the standard compound. Two phenolic metabolites resulting from )-dealkylation were also isolated and identified as 2 and 3-O-demethyl-N-methylcolchiceinamide.