A chain-shortening reaction in orange tortrix moth sex pheromone biosynthesis

Abstract

Various radiolabelled substances were incubated with cell-free preparations obtained from the sex pheromone gland of the orange tortrix moth, Argyrotaenia citrana. Results were consistent with a biosynthetic pathway starting with hexadecanoic acid and involving chain-shortening to tetradecanoic acid, introduction of a double bond at the 11–12 position and reduction of the carboxy group. The unusual chain-shortening reaction was demonstrated by single and dual labelling experiments, and by the use of [3- 14C]-hexadecanoic acid followed by decarboxylation of the resulting tetradecanoic acid to locate most of the radiolabel in the first carbon.