The sex pheromones of two pine sawfly species, Gilpinia frutetorum and Gilpinia socia: Chemical identification, synthesis and biological activity
(2009) In Zeitschrift fuer Naturforschung. Section C: A Journal of Biosciences 64(9-10). p.733-742- 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... (More)
- 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. (Less)
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https://lup.lub.lu.se/record/1532192
- author
- organization
- publishing date
- 2009
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- Sex Pheromone, Gilpinia frutetorum, Gilpinia socia
- in
- Zeitschrift fuer Naturforschung. Section C: A Journal of Biosciences
- volume
- 64
- issue
- 9-10
- pages
- 733 - 742
- publisher
- Verlag der Zeitschrift für Naturforschung
- external identifiers
-
- wos:000272764800020
- scopus:70449589203
- ISSN
- 0939-5075
- project
- Chemical communication in sawflies
- language
- English
- LU publication?
- yes
- id
- 7f56f065-6242-4f23-aa9b-83195455e607 (old id 1532192)
- date added to LUP
- 2016-04-01 12:55:37
- date last changed
- 2024-01-09 05:13:37
@article{7f56f065-6242-4f23-aa9b-83195455e607, abstract = {{3,7-Dimethylpentadecan-2-ol and 3-methylpentadecan-2-ol were identified in female whole body extracts from the two pine sawfly species <i>Gilpinia frutetorum</i> and <i>Gilpinia socia</i>. 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.}}, author = {{Hedenström, Erik and Edlund, Helene and Wassgren, Ann-Britt and Bergström, Gunnar and Anderbrant, Olle and Östrand, Fredrik and Sierpinski, Andrzej and Auger-Rozenberg, Marie-Anne and Herz, Annette and Heitland, Werner and Varama, Martti}}, issn = {{0939-5075}}, keywords = {{Sex Pheromone; Gilpinia frutetorum; Gilpinia socia}}, language = {{eng}}, number = {{9-10}}, pages = {{733--742}}, publisher = {{Verlag der Zeitschrift für Naturforschung}}, series = {{Zeitschrift fuer Naturforschung. Section C: A Journal of Biosciences}}, title = {{The sex pheromones of two pine sawfly species, <i>Gilpinia frutetorum</i> and <i>Gilpinia socia</i>: Chemical identification, synthesis and biological activity}}, volume = {{64}}, year = {{2009}}, }