Sex pheromone biosynthesis in the pine caterpillar moth, Dendrolimus punctatus (Lepidoptera: Lasiocampidae): pathways leading to Z5-monoene and 5,7-conjugated diene components

Abstract

Biosynthesis of the sex pheromone components ( Z)-5-dodecenol and ( Z,E)-5,7-dodecadienol in Dendrolimus punctatus was studied by topical application of deuterium-labeled fatty acids to pheromone glands and subsequent analysis of fatty acyl groups and pheromone components by gas chromatography-mass spectrometry. Our studies suggest that both ( Z)-5-dodecenol and ( Z,E)-5,7-dodecadienol can be biosynthetically derived from chain elongation of palmitate to stearate in the gland, and its subsequent Δ11 desaturation to produce ( Z)-11-octadecenoate. After three cycles of 2-carbon chain-shortening, the pheromone glands produce ( Z)-5-dodecenoate, which is then converted to ( Z)-5-dodecenol by reduction. A second Δ11 desaturation of ( Z)-9-hexadecenoate produces ( Z,E)-9,11-hexadecadienoate, which is then chain shortened in two cycles of beta-oxidation and finally converted to ( Z,E)-5,7-dodecadienol by reduction.