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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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organization
publishing date
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}},
}