Identification of a female-specific, antennally active volatile compound of the currant stem girdler

We identified (Z)-9-octadecen-4-olide as a female-specific, antennally active compound from the currant stem girdler Janus integer Norton. Female specificity was demonstrated by gas chromatographic comparison of liquid chromatography fractions of male and female volatile emissions and whole body ext...

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Bibliographic Details
Published in:Journal of chemical ecology 2001-09, Vol.27 (9), p.1841-1853
Main Authors: COSSE, Allard A, BARTELT, Robert J, JAMES, David G, PETROSKI, Richard J
Format: Article
Language:English
Subjects:
Analytical chemistry
Animal and plant ecology
Animal, plant and microbial ecology
Animals
Autoecology
Biological and medical sciences
Cephidae
Chromatography
Chromatography, Gas
Emissions
Female
Fundamental and applied biological sciences. Psychology
Gas Chromatography-Mass Spectrometry
Hymenoptera - chemistry
Janus integer
Lactones - chemistry
Liquid chromatography
Oleic Acids - chemistry
Protozoa. Invertebrata
Sex Attractants - chemistry
Volatilization
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Summary:We identified (Z)-9-octadecen-4-olide as a female-specific, antennally active compound from the currant stem girdler Janus integer Norton. Female specificity was demonstrated by gas chromatographic comparison of liquid chromatography fractions of male and female volatile emissions and whole body extracts. The gamma-lactone was identified by coupled gas chromatographic-electroantennographic detection (GC-EAD), coupled gas chromatographic-mass spectrometric (GC-MS) analysis, microchemical reactions, and GC and MS comparison with authentic standards. GC-EAD analysis of female volatile emissions and cuticular extracts showed a single peak of activity on male antennae, which was not present in male-derived materials. Female antennae did not respond to any of the tested materials. The hydrogenation product of the natural EAD-active material was a known saturated gamma-lactone. The mass spectrum of the dimethyl disulfide derivative of the natural y -lactone was consistent with a double bond present in the 9 position. Comparison of the natural gamma-lactone and a synthesized racemic mixture of (Z)-9-octadecen-4-olide on a chiral GC column showed the presence of a single enantiomer in the natural material.
ISSN:0098-0331
1573-1561
DOI:10.1023/A:1010412826373