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

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.

• 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
• Avdelning/ar: Funktionell zoologi; Biologiska institutionen; Biodiversitet; Feromongruppen
• Publiceringsår: 2009
• Språk: Engelska
• Sidor: 733-742
• Publikation/Tidskrift/Serie: Zeitschrift fuer Naturforschung. Section C: A Journal of Biosciences
• Volym: 64
• Issue: 9-10
• Dokumenttyp: Artikel i tidskrift
• Förlag: Verlag der Zeitschrift für Naturforschung
• Ämne: Biological Sciences; Zoology
• Nyckelord: Sex Pheromone; Gilpinia frutetorum; Gilpinia socia
• Status: Published
• Projekt: Chemical communication in sawflies
• Forskningsgrupp: Pheromone Group
• ISBN/ISSN/Övrigt: ISSN: 0939-5075