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The sex pheromones of two pine sawfly species, Gilpinia frutetorum and Gilpinia socia: Chemical identification, synthesis and biological activity

Hedenström, Erik; Edlund, Helene; Wassgren, Ann-Britt; Bergström, Gunnar; Anderbrant, Olle LU ; Östrand, Fredrik LU ; Sierpinski, Andrzej; Auger-Rozenberg, Marie-Anne; Herz, Annette and Heitland, Werner, et al. (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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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
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
2010-01-29 12:39:50
date last changed
2016-09-23 18:11:29
@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},
  keyword      = {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},
}