Metabolism of a Fungicide Mepanipyrim by Soil Fungus Cunninghamella elegans ATCC36112

Abstract

Mepanipyrim is a fungicide against several plant pathogens. However, no metabolic details have been established in fungi, which is the most important biomass in the natural environment. Cunninghamella elegans is a well-known fungal species with its strong resemblance to the mammalian xenobiotic metabolism. In this study, the detailed metabolic pathways of mepanipyrim were investigated with C. elegans. Approximately 87% of mepanipyrim was removed within 12 h with concomitant accumulation of nine metabolites. Structures of the metabolites were fully or tentatively identified with GC-MS and (1)H NMR. To determine the possible role of representative oxidative enzymes, piperonyl butoxide and methimazole were treated, and the kinetic responses of mepanipyrim and its metabolites were measured. Dose-dependent inhibition of metabolism was observed with piperonyl butoxide, while methimazole also inhibited the metabolism less effectively. The results indicate the possible involvement of cytochrome P450 and flavin-dependent monooxygenase in mepanipyrim metabolism. Comprehensive metabolic pathways can be deduced from the detailed analysis of metabolite profiles in control and inhibitor assays.