Biosynthetic Pathway of Bombykol, the Sex Pheromone of the Female Silkworm Moth

Abstract

For investigation of the biosynthetic pathway of bombykol ((10E,12Z)-10,12-hexadecadien-1-ol, the female sex pheromone of the silkworm moth), some ¹⁴C-labelled compounds were applied to pheromone glands of 1-day-old virgin female moths 4 hr after lighting (25 ~ 27 hr after eclosion), and their incorporation into the pheromone was measured by the succeeding fractionation with normal-phase and reversed-phase TLC plates. [1-¹⁴C](Z)-11-Hexadecenoic acid changed more easily to bombykol than [1-¹⁴C]hexadecanoic acid, while [1-¹⁴C](E)-11-hexadecenoic acid and [1-¹⁴C]hexadecan-1-ol were scarcely incorporated into the pheromone. This result confirms the biosynthetic pathway via (Z)-l 1-hexadecenoate and (10E,12Z)-10,12-hexadecadienoate, which has been proposed by Yamaoka et al. and Bjostad and Roelofs. Some [1-¹⁴C](Z)-11-hexadecen-1-ol was changed to bombykol, suggesting that the alcohol was oxidized to (Z)-l 1-hexadecenoic acid and this acid was taken into the biosynthetic pathway.