Biosynthesis and endocrine control of the production of the German cockroach sex pheromone 3,11-dimethylnonacosan-2-one.

The biosynthesis and endocrine regulation of sex pheromone production in the female German cockroach (Blattella germanica) were determined. Radio-TLC and radio-GLC were used to demonstrate the metabolism of 3,11-dimethylnonacosane, a major cuticular lipid component, to the corresponding alkan-2-ol and methyl ketone. [11,12-3H2]-3,11-Dimethylnonacosan-2-ol was efficiently metabolized to the methyl ketone, and radio-GLC showed that the methyl ketone product from both experiments was coeluted with a methyl ketone standard. A comparison of the metabolism of the labeled dimethylalkane and dimethylalkan-2-ol by age and sex showed that both males and females from day 1 through day 9 after adult emergence readily metabolized the alcohol to the corresponding methyl ketone, whereas only females of 5-9 days postemergence efficiently converted the labeled dimethylalkane to the corresponding methyl ketone. Application of the juvenile hormone analog hydroprene induced significant increases in the conversion of the labeled hydrocarbon to the methyl ketone in starved adult females as well as in females fed a protein-free diet, conditions under which endogenous juvenile hormone biosynthesis is nearly undetectable. These data show that the methyl ketone sex pheromone is formed by the hydroxylation and oxidation of the 3,11-dimethylalkane at the 2 position, show that the age- and sex-specific step in this process is the conversion of 3,11-dimethylnonacosane to 3,11-dimethylnonacosan-2-ol, and provide evidence that juvenile hormone regulates sex pheromone production in the German cockroach.