New contact sex pheromone components of the german cockroach, Blattella germanica, predicted from the proposed biosynthetic pathway

Upon contacting the cuticle of a sexually mature female, a male German cockroach exhibits a characteristic courtship behavior: he turns away from the female and raises his wings, thereby exposing tergal glands. The glandular secretion stimulates the female to mount the male and feed, thus positioning her appropriately for copulation. A multi-component contact sex pheromone produced by females is responsible for eliciting courtship behavior. The most abundant pheromone components are 3,11-dimethylnonacosan-2-one and 3,11-dimethylheptacosan-2-one, oxidation products of the abundant hydrocarbon analogs 3,11-dimethylnonacosane and 3,11-dimethylheptacosane, respectively. The C-29-dimethyl ketone is thought to be further metabolized to two less abundant pheromone components, 29-hydroxy-3,11-dimethylnonacosan-2-one and 29-oxo-3,11-dimethylnonacosan-2-one. Based on this proposed biosynthetic pathway of pheromone production, we hypothesized that 3,11-dimethylheptacosan-2-one also would be oxidized to give two candidate pheromone components, 27-hydroxy-3,11-dimethylheptacosan-2-one, and 27-oxo-3,11-dimethylheptacosan-2-one. By using bioassay-guided fractionation and chemical analyses of cuticular extracts of virgin females and synthesis of the (3S,11S)-isomer of each of the two predicted pheromone components, we showed that the epicuticle of the German cockroach does indeed contain these two compounds. The contact sex pheromone of the female German cockroach, thus may consist of at least six biosynthetically related components.