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Sex pheromone of th...
Sex pheromone of the pine sawfly, Gilpinia pallida: Chemical identification, synthesis, and biological activity
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- Hedenström, Erik (author)
- Mid Sweden University,Mittuniversitetet,Institutionen för naturvetenskap (-2008)
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- Edlund, Helene (author)
- Mid Sweden University,Mittuniversitetet,Institutionen för naturvetenskap (-2008)
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- Wassgren, Ann-Britt (author)
- Gothenburg University,Göteborgs universitet,University of Gothenburg,Institutionen för växt- och miljövetenskaper,Department of Plant and Environmental Sciences,Göteborg University
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- Bergström, Gunnar (author)
- Gothenburg University,Göteborgs universitet,University of Gothenburg,Institutionen för växt- och miljövetenskaper,Department of Plant and Environmental Sciences,Göteborg University
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- Anderbrant, Olle (author)
- Lund University,Lunds universitet,Funktionell zoologi,Biologiska institutionen,Naturvetenskapliga fakulteten,Functional zoology,Department of Biology,Faculty of Science
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- Östrand, Fredrik (author)
- Lund University,Lunds universitet,Biologiska institutionen,Naturvetenskapliga fakulteten,Department of Biology,Faculty of Science
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- Sierpinski, Andrzej (author)
- Forest Research Institute, Poland,Forest Research Institute, Warsaw
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- Auger-Rozenberg, Marie-Anne (author)
- Institut National de la Recherche Agronomique, France,INRA National Institute of Agricultural Research
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- Herz, Marie-Anne (author)
- Technische Universität München, Germany
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- Heitland, Werner (author)
- Technische Universität München, Germany,Technical University of Munich
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- Varama, Martti (author)
- Finnish Forest Research Institute, Finland,Natural Resources Institute Finland (Luke)
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- Herz, Anette (author)
- Technical University of Munich
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(creator_code:org_t)
- 2006-10-31
- 2006
- English.
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In: Journal of Chemical Ecology. - : Springer Science and Business Media LLC. - 0098-0331 .- 1573-1561. ; 32:11, s. 2525-2541
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Abstract
Subject headings
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- 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.
Subject headings
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
- NATURVETENSKAP -- Biologi -- Zoologi (hsv//swe)
- NATURAL SCIENCES -- Biological Sciences -- Zoology (hsv//eng)
- NATURVETENSKAP -- Biologi (hsv//swe)
- NATURAL SCIENCES -- Biological Sciences (hsv//eng)
- NATURVETENSKAP -- Biologi -- Ekologi (hsv//swe)
- NATURAL SCIENCES -- Biological Sciences -- Ecology (hsv//eng)
- NATURVETENSKAP -- Biologi -- Biokemi och molekylärbiologi (hsv//swe)
- NATURAL SCIENCES -- Biological Sciences -- Biochemistry and Molecular Biology (hsv//eng)
Keyword
- 3
- 7-Dimethyl-2-tetradecanol
- Electrophysiology
- Field activity
- Gas chromatography
- Gilpinia pallida
- Lipase
- Mass spectrometry
- Sex pheromone
- Stereoisomer
- Synthesis
- Chemistry
- Kemi
- 3
- 7-dimethyl-2-tetradecanol
- sex pheromone
- electrophysiology
- gas chromatography
- mass spectrometry
- synthesis
- stereoisomer
- lipase
- field activity
- Gilpinia pallida
- candida-rugosa lipase
- neodiprion-sertifer
- stereoisomeric composition
- macrodiprion-nemoralis
- diprionyl acetate
- hymenoptera
- precursors
- acids
- esterification
- components
Publication and Content Type
- ref (subject category)
- art (subject category)
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- By the author/editor
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Hedenström, Erik
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Edlund, Helene
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Wassgren, Ann-Br ...
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Bergström, Gunna ...
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Anderbrant, Olle
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Östrand, Fredrik
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Sierpinski, Andr ...
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Auger-Rozenberg, ...
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Herz, Marie-Anne
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Heitland, Werner
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Varama, Martti
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Herz, Anette
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- About the subject
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- NATURAL SCIENCES
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NATURAL SCIENCES
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and Chemical Science ...
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- NATURAL SCIENCES
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NATURAL SCIENCES
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and Biological Scien ...
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and Zoology
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- NATURAL SCIENCES
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NATURAL SCIENCES
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and Biological Scien ...
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- NATURAL SCIENCES
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NATURAL SCIENCES
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and Biological Scien ...
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and Ecology
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- NATURAL SCIENCES
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NATURAL SCIENCES
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and Biological Scien ...
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and Biochemistry and ...
- Articles in the publication
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Journal of Chemi ...
- By the university
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Mid Sweden University
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Lund University
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University of Gothenburg