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Sex pheromone of the pine sawfly, Gilpinia pallida: Chemical identification, synthesis, and biological activity

Hedenström, Erik; Edlund, H; Wassgren, Ann-Britt; Bergström, Gunnar; Anderbrant, Olle LU ; Östrand, Fredrik LU ; Sierpinski, A; Auger-Rozenberg, MA; Herz, Anette and Heitland, Werer, et al. (2006) In Journal of Chemical Ecology 32(11). p.2525-2541
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... (More)
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. (Less)
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keywords
3, 7-dimethyl-2-tetradecanol, sex pheromone, electrophysiology, gas chromatography, mass spectrometry, synthesis, stereoisomer, lipase, field activity, Gilpinia pallida
in
Journal of Chemical Ecology
volume
32
issue
11
pages
2525 - 2541
publisher
Springer
external identifiers
  • wos:000242130700014
  • scopus:33751119255
ISSN
1573-1561
DOI
10.1007/s10886-006-9161-5
project
Chemical communication in sawflies
language
English
LU publication?
yes
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76d59ef7-e5c7-43f7-b5d6-5da45e32f648 (old id 163714)
date added to LUP
2011-07-11 11:10:51
date last changed
2019-08-07 01:52:24
@article{76d59ef7-e5c7-43f7-b5d6-5da45e32f648,
  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.},
  author       = {Hedenström, Erik and Edlund, H and Wassgren, Ann-Britt and Bergström, Gunnar and Anderbrant, Olle and Östrand, Fredrik and Sierpinski, A and Auger-Rozenberg, MA and Herz, Anette and Heitland, Werer and Varama, M},
  issn         = {1573-1561},
  keyword      = {3,7-dimethyl-2-tetradecanol,sex pheromone,electrophysiology,gas chromatography,mass spectrometry,synthesis,stereoisomer,lipase,field activity,Gilpinia pallida},
  language     = {eng},
  number       = {11},
  pages        = {2525--2541},
  publisher    = {Springer},
  series       = {Journal of Chemical Ecology},
  title        = {Sex pheromone of the pine sawfly, <i>Gilpinia pallida</i>: Chemical identification, synthesis, and biological activity},
  url          = {http://dx.doi.org/10.1007/s10886-006-9161-5},
  volume       = {32},
  year         = {2006},
}