Oxaspiropentane derivatives as effective sex pheromone analogues in the gypsy moth: electrophysiological and behavioral evidence

Chem Senses. 2007 Oct;32(8):755-63. doi: 10.1093/chemse/bjm043. Epub 2007 Jul 14.

Abstract

A number of oxaspiropentane derivatives (OXPs) were tested as potential (+)-disparlure analogues, with the aim of identifying any possible interaction of these compounds, be it additive, synergetic, or inhibitory, with the pheromone response in the male gypsy moth Lymantria dispar. As assessed by male electroantennograms, 2 OXPs, 2-decyl-1-oxaspiro[2.2]pentane (OXP-01) and 4-(1-oxaspiro[2.2]pent-2-yl)butan-1-ol (OXP-04), were found to be effective. OXP-01 had no stimulatory effect but strongly decreased the response to (+)-disparlure in a blend in a 1:1 ratio. By contrast, OXP-04 proved to be more stimulating than (+)-disparlure and also had an additive effect in the blend. Single-cell recordings from the sensilla trichoidea showed the activity of 2 cells, one of which responded to (+)-disparlure. OXP-01 reduced the stimulating effectiveness of pheromone by silencing the pheromone-responding unit when the 2 compounds were presented in blend, whereas OXP-04 mimicked the pheromone response, evidenced by exciting the pheromone-responding neuron when tested alone. Behavioral observations are in agreement with electrophysiological results.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Air
  • Animals
  • Behavior, Animal
  • Dose-Response Relationship, Drug
  • Electrophysiology / methods*
  • Epoxy Compounds / chemistry*
  • Female
  • Male
  • Models, Chemical
  • Moths
  • Odorants
  • Pheromones
  • Sex Attractants / metabolism*
  • Sexual Behavior, Animal
  • Spiro Compounds / chemistry*
  • Time Factors

Substances

  • Epoxy Compounds
  • Pheromones
  • Sex Attractants
  • Spiro Compounds
  • spiropentaneacetic acid