Pink bollworm sex pheromone biosynthesis from oleic acid

Abstract Sex pheromone biosynthesis in the pink bollworm, Pectinophora gossypiella , was examined using deuterium-labelled fatty acids coupled with analysis by gas chromatography-mass spectrometry. The two pheromone components, ( Z , Z )-7,11- and ( Z , E )-7,11-hexadecadienyl acetates, were shown to be biosynthesized from oleic acid by initial 2 carbon chain-shortening to ( Z )-7-hexadecenoate followed by Δ11 desaturation. When labelled stearic or palmitic acids were applied to the sex pheromone glands of female pink bollworm, label was not detected in the two pheromone components suggesting that oleate for pheromone biosynthesis is not produced in the gland but is sequestered from elsewhere in the insect.