Abstract
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.
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Acknowledgments
We thank Johan Kristoffersson for help with the field test in Arjeplog, Sweden. The research was supported by the Swedish Natural Science Research Council (NFR), Swedish Council for Forestry and Agricultural Research (SJFR), Carl Trygger’s Foundation for Scientific Research and the Commission of the European Communities, Agriculture and Fisheries (FAIR), specific RTD program, contract no. FAIR1-CT95-0339, “Pine sawfly pheromones for sustainable management of European forests” (PHERODIP). This study does not necessarily reflect the Commission’s view and in no way anticipates its future policies in this area. Financial support to the group in Göteborg from The Royal Society of Arts and Sciences in Göteborg (KVVS) and the Ebba and Sven Schwartz Foundation is gratefully acknowledged.
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Hedenström, E., Edlund, H., Wassgren, AB. et al. Sex Pheromone of the Pine Sawfly, Gilpinia pallida: Chemical Identification, Synthesis, and Biological Activity. J Chem Ecol 32, 2525–2541 (2006). https://doi.org/10.1007/s10886-006-9161-5
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DOI: https://doi.org/10.1007/s10886-006-9161-5