Metabolically blocked analogs of housefly sex pheromone: II. Metabolism studies

Abstract

Analogs of (Z)-9-tricosene (Z9–23: Hy) bearing methyl substituents, cyclopropyl groups, fluorine substituents, and additional double bonds were used to probe the substrate requirements for the monooxygenase system that converts Z9–23: Hy to the corresponding epoxide and ketone. Three of the seven analogs tested, 10-fluoro-(Z)-14-tricosene, 10,10-difluoro-(Z)-14-tricosene, and 14-methyl-(Z)-9-tricosene, were metabolized to the corresponding epoxide. Compounds with two methyl groups, a cyclopropane group, a hydroxy group, or an additional double bond at the 14 position were not epoxidized at the 9,10 position. This suggests that only minimal structural change at the 14-position of Z9–23: Hy is allowed with retention of metabolic activity. None of the analogs tested were hydroxylated at the position equivalent to the 14 position of Z9–23:Hy. Of the 13 analogs tested as inhibitors of Z9–23:Hy metabolism, the two compounds that were the most effective inhibitors in both male and female houseflies were (Z)-14-tricosen-10-one and 1-nonyl-1-[(Z)-4-tetradecen-1-yl]-cyclopropane. These data show that the poly substrate monooxy genase that metabolizes Z9–23: Hy in the housefly has very strict structural requirements for the substrate.