The sex pheromones of two pine sawfly species, <i>Gilpinia frutetorum</i> and <i>Gilpinia socia</i>: Chemical identification, synthesis and biological activity
Hedenström, Erik; Edlund, Helene; Wassgren, Ann-Britt; Bergström, Gunnar, et al. (2009). The sex pheromones of two pine sawfly species, <i>Gilpinia frutetorum</i> and <i>Gilpinia socia</i>: Chemical identification, synthesis and biological activity. Zeitschrift fuer Naturforschung. Section C: A Journal of Biosciences, 64, (9-10), 733 - 742
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Published
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English
Authors:
Hedenström, Erik
;
Edlund, Helene
;
Wassgren, Ann-Britt
;
Bergström, Gunnar
, et al.
Department:
Functional zoology
Department of Biology
Biodiversity
Pheromone Group
Project:
Chemical communication in sawflies
Research Group:
Pheromone Group
Abstract:
3,7-Dimethylpentadecan-2-ol and 3-methylpentadecan-2-ol were identified in female whole body extracts from the two pine sawfly species Gilpinia frutetorum and Gilpinia socia. This is the first observation of 3-methylpentadecan-2-ol in extracts of a female pine sawfly species. Synthetic and highly pure stereoisomers of 3,7-dimethylpentadecan-2-ol and 3-methylpentadecan-2-ol were used to verify that the (2S,3R,7R)isomer of 3,7-dimethylpentadecan-2-ol and (2S,3R)-3-methylpentadecan-2-ol were present in the extracts. The four stereoisomers of 3-methylpentadecan-2-ol and their biologically active esters were produced via chemoenzymatic methods and the synthesis is described in detail. Male G. socia antennae responded strongly in EAG recordings to the (2S,3R)-isomer of the acetate and propionate of 3-methylpentadecan-2-ol. Male antennae of both G. frutetorum and G. socia also responded to the (2S,3R,7R)- and (2S,3R,7S)-acetates of 3,7-dimethylpentadecan-2-ol.
Keywords:
Sex Pheromone ;
Gilpinia frutetorum ;
Gilpinia socia ;
Biological Sciences ;
Zoology
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