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

Författare:
  • Erik Hedenström
  • Helene Edlund
  • Ann-Britt Wassgren
  • Gunnar Bergström
  • Olle Anderbrant
  • Fredrik Östrand
  • Andrzej Sierpinski
  • Marie-Anne Auger-Rozenberg
  • Annette Herz
  • Werner Heitland
  • Martti Varama
Publiceringsår: 2009
Språk: Engelska
Sidor: 733-742
Publikation/Tidskrift/Serie: Zeitschrift fuer Naturforschung. Section C: A Journal of Biosciences
Volym: 64
Nummer: 9-10
Dokumenttyp: Artikel i tidskrift
Förlag: Verlag der Zeitschrift für Naturforschung

Sammanfattning

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.

Nyckelord

  • Biological Sciences
  • Zoology
  • Sex Pheromone
  • Gilpinia frutetorum
  • Gilpinia socia

Övriga

Published
  • Chemical communication in sawflies
  • Pheromone Group
  • ISSN: 0939-5075

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