Sex Pheromone of the Pine Sawfly, Gilpinia pallida: Chemical Identification, Synthesis, and Biological Activity

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• 作者：Erik Hedenstr枚m (1)
  Helene Edlund (1)
  Ann-Britt Wassgren (2)
  Gunnar Bergstr枚m (2)
  Olle Anderbrant (3)
  Fredrik 脰strand (3)
  Andrzej Sierpinski (4)
  Marie-Anne Auger-Rozenberg (5)
  Annette Herz (6) (8)
  Werner Heitland (6)
  Martti Varama (7)
  
• 关键词：3 ; 7 ; Dimethyl ; 2 ; tetradecanol ; sex pheromone ; electrophysiology ; gas chromatography ; mass spectrometry ; synthesis ; stereoisomer ; lipase ; field activity ; Gilpinia pallida
• 刊名：Journal of Chemical Ecology
• 出版年：2006
• 出版时间：November 2006
• 年：2006
• 卷：32
• 期：11
• 页码：2525-2541
• 全文大小：288KB
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  29. Wmphasis type-small-caps">assgren , A.-B., Bmphasis type-small-caps">ergstr枚m , G., Smphasis type-small-caps">ierpinski , A., Amphasis type-small-caps">nderbrant , O., Hmphasis type-small-caps">枚gberg , H.-E., and Hmphasis type-small-caps">edenstr枚m , E. 2000. Sex pheromone of the pine sawfly / Macrodiprion nemoralis (Hymenoptera: Diprionidae): Identification of the precursor (2 / S,3 / R,7 / R,9 / S)-3,7,9-trimethyl-2-tridecanol and the active pheromone (2 / S,3 / R,7 / R,9 / S)-3,7,9-trimethyl-2-tridecyl acetate. / Naturwissenschaften 87:24鈥?9. CrossRef
  
• 作者单位：Erik Hedenstr枚m (1)
  Helene Edlund (1)
  Ann-Britt Wassgren (2)
  Gunnar Bergstr枚m (2)
  Olle Anderbrant (3)
  Fredrik 脰strand (3)
  Andrzej Sierpinski (4)
  Marie-Anne Auger-Rozenberg (5)
  Annette Herz (6) (8)
  Werner Heitland (6)
  Martti Varama (7)
  
  1. Department of Natural Sciences, Mid Sweden University, 85170, Sundsvall, Sweden
  2. Chemical Ecology, G枚teborg University, P.O. Box 461, 40530, G枚teborg, Sweden
  3. Department of Ecology, Lund University, Ecology Building, 22362, Lund, Sweden
  4. Forest Research Institute, Bitwy Warszawskiej 1920 R. No. 3, 00-973, Warsaw, P.O. Box 61, Poland
  5. Institut National de la Recherche Agronomique, Centre de Recherches d`Orleans, Ardon, 45160, Olivet, France
  6. Department of Ecology, Institute of Animal Ecology, Technische Universit盲t M眉nchen, Am Hochanger 13, 85343, Freising, Germany
  8. Institute for Plant Protection in Fruit Crops, Federal Research Centre for Agriculture and Forestry, Schwabenheimer Str. 101, 69221, Dossenheim, Germany
  7. The Finnish Forest Research Institute, Vantaa Research Centre, P. O. Box 18, 01301, Vantaa, Finland
  

文摘

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.