The browser you are using is not supported by this website. All versions of Internet Explorer are no longer supported, either by us or Microsoft (read more here: https://www.microsoft.com/en-us/microsoft-365/windows/end-of-ie-support).

Please use a modern browser to fully experience our website, such as the newest versions of Edge, Chrome, Firefox or Safari etc.

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

Author

  • 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

Summary, in English

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.

Publishing year

2009

Language

English

Pages

733-742

Publication/Series

Zeitschrift fuer Naturforschung. Section C: A Journal of Biosciences

Volume

64

Issue

9-10

Document type

Journal article

Publisher

Verlag der Zeitschrift für Naturforschung

Topic

  • Biological Sciences
  • Zoology

Keywords

  • Sex Pheromone
  • Gilpinia frutetorum
  • Gilpinia socia

Status

Published

Project

  • Chemical communication in sawflies

Research group

  • Pheromone Group

ISBN/ISSN/Other

  • ISSN: 0939-5075