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(S)-fuscumol and (S)-fuscumol acetate produced by a male Astyleiopus variegatus (Coleoptera: Cerambycidae)

Published online by Cambridge University Press:  29 January 2013

Gabriel P. Hughes ,
Yunfan Zou ,
Jocelyn G. Millar  and
Matthew D. Ginzel
Gabriel P. Hughes
Affiliation:
Department of Entomology, Purdue University, West Lafayette, Indiana 47907, United States of America
Yunfan Zou
Affiliation:
Department of Entomology, University of California, Riverside, California 92521, United States of America
Jocelyn G. Millar
Affiliation:
Department of Entomology, University of California, Riverside, California 92521, United States of America
Matthew D. Ginzel*
Affiliation:
Department of Entomology, Purdue University, West Lafayette, Indiana 47907, United States of America
*
1Corresponding author (e-mail: [email protected]).
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Abstract

Within the family Cerambycidae (Coleoptera), (E)-6,10-dimethyl-5,9-undecadien-2-ol (fuscumol) and (E)-6,10-dimethyl-5,9-undecadien-2-yl acetate (fuscumol acetate) have been shown to attract several species in the subfamily Lamiinae. However, it is not yet clear whether beetles within the subfamily actually produce these compounds as pheromones or rather respond to them as kairomones. We report here that male Astyleiopus variegatus (Haldeman) produce both fuscumol and fuscumol acetate, suggesting that the compounds are indeed pheromones for this species. We also determined that the absolute configurations of these compounds are (S)-fuscumol and (S)-fuscumol acetate by synthesis of both enantiomers of each.

Résumé

Il est connu qu'au sein de la famille des Cerambycidae (Coleoptera), le (E)-6,10-diméthyl-5,9-undécadién-2-ol (fuscumol) et l'acétate de (E)-6,10-diméthyl-5,9-undécadién-2-yle (acétate de fuscumol) attirent plusieurs espèces de la sous-famille des Lamiinae. Il n'est cependant pas clair si les coléoptères de la sous-famille produisent de fait ces composés comme phéromones ou alors y réagissent comme à des kairomones. Nous rapportons ici que les mâles d’Astyleiopus variegatus (Haldeman) produisent à la fois du fuscumol et de l'acétate de fuscumol, ce qui laisse croire que les deux composés servent de phéromones chez cette espèce. Nous avons aussi déterminé que les configurations absolues de ces composés sont le (S)-fuscumol et l'acétate de (S)-fuscumol par la synthèse des deux énantiomères de chacun.

Type
Behaviour & Ecology – NOTE
Information
The Canadian Entomologist , Volume 145 , Issue 3 , June 2013 , pp. 327 - 332
Copyright
Copyright © Entomological Society of Canada 2013 

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