title: (7R,8S)-cis-7,8-epoxy-2-methyloctadec-17-ene: a novel trace component from the sex pheromone gland of gypsy moth, Lymantria dispar.
abstract: Considering the vast Eurasian distribution of gypsy moth, Lymantria dispar (Lepidoptera: Lymantriidae), the many subspecies, and their presence in different lymantriid communities, we tested the hypothesis that L. dispar populations in eastern Asia employ one or more pheromone components in addition to the previously known single component pheromone (7R,8S)-cis-7,8-epoxy-2-methyloctadecane [= (+)-disparlure]. Coupled gas chromatographic-electroantennographic detection (GC-EAD) analyses of pheromone gland extracts of female L. dispar sensu lato (including both AGM and NAGM) on four GC columns (DB-5, DB-23, DB-210, and SP-1000) revealed a new trace component that eluted just before (DB-5; DB-210) or after (DB-23, SP-1000) disparlure, and elicited strong antennal responses. Isolation of this compound by high-performance liquid chromatography and hydrogenation produced disparlure, suggesting that the new component had the molecular skeleton of disparlure, with one or more double bonds. Of all possible monounsaturated cis-7,8-epoxy-2-methyloctadecenes, only cis-7,8-epoxy-2-methyloctadec-17-ene co-chromatographed with the insect-produced compound on all GC columns and elicited comparable antennal responses. In field experiments in Honshu (Japan) with enantioselectively synthesized compounds, (7R,8S)-cis-7,8-epoxy-2-methyloctadec-17-ene (7R8S-epo-2me-17-ene-18Hy) was weakly attractive to male L. dispar, but was less effective as a trap bait than (+)-disparlure, and failed to enhance attractiveness of (+)-disparlure when tested in blends. The antipode, (7S,8R)-cis-7,8-epoxy-2-methyloctadec-17-ene, was not attractive, and when added to (+)-disparlure and/or 7R8S-epo-2me-17-ene-18Hy reduced attractiveness. Thus, the biological role of 7R8S-epo-2me-17-ene-18Hy remains unclear. It may enhance pheromone attractiveness or specificity in other L. dispar populations within their vast Eurasian distribution.
authors.affiliation: Department of Biological Sciences, Simon Fraser University Burnaby, British Columbia, Canada V5A 1S6. gries@sfu.ca
authors.forename: Regine
authors.initials: R
authors.lastname: Gries
authors.forename: Grigori
authors.initials: G
authors.lastname: Khaskin
authors.forename: Paul W
authors.initials: PW
authors.lastname: Schaefer
authors.forename: Roger
authors.initials: R
authors.lastname: Hahn
authors.forename: Tadao
authors.initials: T
authors.lastname: Gotoh
authors.forename: Gerhard
authors.initials: G
authors.lastname: Gries
mesh_terms: D000818:Animals; D004594:Electrophysiology; D004852:Epoxy Compounds / Q000032:analysis*; D005088:Exocrine Glands / Q000737:chemistry / Q000502:physiology; D005260:Female; D008401:Gas Chromatography-Mass Spectrometry; D008297:Male; D009036:Moths / Q000737:chemistry / Q000502:physiology*; D012724:Sex Attractants / Q000032:analysis / Q000737:chemistry*; D013229:Stearic Acids / Q000032:analysis*
chemical_list: C503516:(7R,8S)-cis-7,8-epoxy-2-methyloctadec-17-ene; D004852:Epoxy Compounds; D012724:Sex Attractants; D013229:Stearic Acids