Identification of conjugated pentadecadienals as sex pheromone components of the sphingid moth, Dolbina tancrei

J Chem Ecol. 2013 Dec;39(11-12):1441-7. doi: 10.1007/s10886-013-0357-1. Epub 2013 Nov 6.

Abstract

Homologs of bombykal, (10E,12Z)-10,12-hexadecadienal, have been reported to be sex pheromones or sexual attractants of several species of sphingid moths. In this study, we identified novel bombykal analogs as sex pheromone components from a Japanese sphingid moth, Dolbina tancrei. Staudinger (Sphingidae: Lepidoptera). Sex pheromone gland extracts from calling female moths were subjected to gas chromatography/electroantennograhic detection (GC/EAD), gas chromatography/mass spectrometry (GC/MS), and gas chromatography (GC) analyses. GC/EAD analyses showed two active components in the crude pheromone extracts. GC/MS analysis determined these two components to be pentadecadienals. GC/MS of their MTAD derivatives showed conjugated double bonds at the 9- and 11-positions, indicating 9,11-pentadecadienals. The isomeric configurations of these candidates were determined by comparison of their Kováts retention indices with those of synthetic compounds. Field bioassays with the four isomers of 9,11-pentadecadienal and their mixtures confirmed that the two sex pheromone components of D. tancrei are (9E,11Z)-9,11-pentadecadienal and (9Z,11Z)-9,11-pentadecadienal, with the highest male catches observed for a 90:10 blend. This is the first report of 9,11-pentadecadienals as sex pheromone components in lepidopteran species.

MeSH terms

  • Alkadienes / analysis*
  • Animals
  • Female
  • Male
  • Moths / physiology*
  • Sex Attractants / chemistry*
  • Sex Attractants / physiology
  • Sexual Behavior, Animal

Substances

  • Alkadienes
  • Sex Attractants
  • bombykal