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Sex pheromone of the pine sawfly, Gilpinia pallida: Chemical identification, synthesis, and biological activity

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Author

  • Erik Hedenström
  • Helén Edlund
  • Ann-Britt Wassgren
  • Gunnar Bergström
  • Olle Anderbrant
  • Fredrik Östrand
  • A Sierpinski
  • MA Auger-Rozenberg
  • Anette Herz
  • Werer Heitland
  • M Varama
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Summary, in English

We present the identification of the sex pheromone in the pine sawfly, Gilpinia pallida, including analysis of the female pheromone content, male antennal response and attraction in the field, and synthesis of the most active pheromone component. Several 3,7-dimethyl-2-alkanols were identified from female whole-body extracts, including some compounds with a 2R configuration. This is the first observation of such compounds in a pine sawfly species. Antennae of male G. pallida responded strongly in electroantennograph (EAG) recordings to the (2S,3R,7R)-isomers of the propionates of 3,7-dimethyl-2-tridecanol, 3,7-dimethyl-2-tetradecanol, and 3,7-dimethyl-2-pentadecanol, as well as to the acetates of the tri- and pentadecanols (the acetate of the tetradecanol was not tested). The propionate of (2S,3R,7R)-3,7-dimethyl-2-tetradecanol caught more males in the field than the corresponding isomer of tri- or pentadecanol. We suggest that the (2S,3R,7R)-isomer of 3,7-dimethyl-2-tetradecanol is likely the main sex pheromone precursor in G. pallida, with a subsidiary role for the (2S,3R,7R)-isomer of the tridecanol. Preparation of highly pure (2R,3R,7R)- and (2S,3R,7R)-stereoisomers of 3,7-dimethyl-2-tetradecanol, including the biological active esters, was performed via chemoenzymatic methods and is described in detail.

Publishing year

2006

Language

English

Pages

2525-2541

Publication/Series

Journal of Chemical Ecology

Volume

32

Issue

11

Document type

Journal article

Publisher

Springer

Topic

  • Zoology
  • Biological Sciences

Keywords

  • 3
  • 7-dimethyl-2-tetradecanol
  • sex pheromone
  • electrophysiology
  • gas chromatography
  • mass spectrometry
  • synthesis
  • stereoisomer
  • lipase
  • field activity
  • Gilpinia pallida

Status

Published

Project

  • Chemical communication in sawflies

Research group

  • Pheromone Group

ISBN/ISSN/Other

  • ISSN: 1573-1561