Synergism between Enantiomers Creates Species-Specific Pheromone Blends and Minimizes Cross-Attraction for Two Species of Cerambycid Beetles

J Chem Ecol. 2016 Nov;42(11):1181-1192. doi: 10.1007/s10886-016-0782-z. Epub 2016 Oct 22.

Abstract

Research over the last decade has revealed extensive parsimony among pheromones within the large insect family Cerambycidae, with males of many species producing the same, or very similar aggregation pheromones. Among some species in the subfamily Cerambycinae, interspecific attraction is minimized by temporal segregation, and/or by minor pheromone components that synergize attraction of conspecifics or inhibit attraction of heterospecifics. Less is known about pheromone-based mechanisms of reproductive isolation among species in the largest subfamily, the Lamiinae. Here, we present evidence that the pheromone systems of two sympatric lamiine species consist of synergistic blends of enantiomers of (E)-6,10-dimethyl-5,9-undecadien-2-ol (fuscumol) and the structurally related (E)-6,10-dimethyl-5,9-undecadien-2-yl acetate (fuscumol acetate), as a mechanism by which species-specific blends of pheromone components can minimize interspecific attraction. Male Astylidius parvus (LeConte) were found to produce (R)- and (S)-fuscumol + (R)-fuscumol acetate + geranylacetone, whereas males of Lepturges angulatus (LeConte) produced (R)- and (S)-fuscumol acetate + geranylacetone. Field experiments confirmed that adult beetles were attracted only by their species-specific blend of the enantiomers of fuscumol and fuscumol acetate, respectively, and not to the individual enantiomers. Because other lamiine species are known to produce single enantiomers or blends of enantiomers of fuscumol and/or fuscumol acetate, synergism between enantiomers, or inhibition by enantiomers, may be a widespread mechanism for forming species-specific pheromone blends in this subfamily.

Keywords: Astylidius parvus; Cerambycidae; Fuscumol; Fuscumol acetate; Lepturges angulatus; Longhorned beetle; Reproductive isolation; Semiochemical.

MeSH terms

  • Animals
  • Biological Assay
  • Coleoptera / drug effects*
  • Drug Synergism
  • Female
  • Male
  • Sex Attractants / chemistry*
  • Sex Attractants / pharmacology*
  • Sexual Behavior, Animal / drug effects*
  • Species Specificity
  • Stereoisomerism

Substances

  • Sex Attractants