Sex pheromone of the housefly: Metabolism of (Z)-9-tricosene to (Z)-9,10-epxytricosane and (Z)-14-tricosen-10-one

Abstract

Components of the sex pheromone of the female housefly, (Z)-9,10-epoxytricosane and (Z)-14-tricosen-10-one, are absent on the surface of newly emerged insects, first appear on females on day 2, and increase in amount to day 10. All body parts contain these components, with the legs and abdomen containing the largest amounts. The incorporation of [1- 14C]acetate into the non-hydrocarbon cuticular (NHC) fraction, which includes 9,10-epoxytricosane and (Z)-14-tricosen-10-one is very low in newly emerged and one-day-old female houseflies and then increases dramatically from day 2 to 6. The major labelled components in this fraction are the C 23 epoxide and ketone. The increased amounts and incorporation of [1- 14C]acetate into the C 23 epoxide and ketone correlate closely with the production of (Z)-9-tricosene. [9,10- 3H](Z)-9-Tricosene is readily converted to oxygenated components in female insects giving rise to the C 23 epoxide (85.5%), C 23 ketone (13.0%) and more polar components (1.5%). Both female and male insects of all ages metabolize [9,10- 3H](Z)-9-tricosene to the epoxide and ketone. All major body parts in both males and females metabolized (Z)-9-tricosene when it was applied to the surface of the insect, with the highest rate of metabolism observed by the legs of male insects.