The sex pheromones of two pine sawfly species, Gilpinia frutetorum and Gilpinia socia: Chemical identification, synthesis and biological activity
Author
Summary, in English
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.
Publishing year
2009
Language
English
Pages
733-742
Publication/Series
Zeitschrift fuer Naturforschung. Section C: A Journal of Biosciences
Volume
64
Issue
9-10
Document type
Journal article
Publisher
Verlag der Zeitschrift für Naturforschung
Topic
- Biological Sciences
- Zoology
Keywords
- Sex Pheromone
- Gilpinia frutetorum
- Gilpinia socia
Status
Published
Project
- Chemical communication in sawflies
Research group
- Pheromone Group
ISBN/ISSN/Other
- ISSN: 0939-5075