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Identification of the sex pheromone of the currant shoot borer, Lampronia capitella

Löfstedt, Christer LU ; Zhu, Jun-Wei; Kozlov, Michail V; Buda, Vincas; Jirle, Erling LU ; Hellqvist, Sven; Löfqvist, Jan; Plass, E; Franke, S and Francke, Wittko (2004) In Journal of Chemical Ecology 30(3). p.643-658
Abstract
Under an artificial light: dark cycle, females of Lampronia capitella were observed calling, with extended terminal abdominal segments, during the first 2 hr of the photoperiod. Extracts of terminal abdominal segments from females elicited large electroantennographic responses from male antennae. Gas chromatography with electroantennographic detection revealed three active peaks. Based on comparison of retention times and mass spectra of synthetic standards, these compounds were identified as (Z;Z)-9,11-tetradecadienol and the corresponding acetate and aldehyde. The electroantennographic activity of the four geometric isomers of all three compounds was investigated, and the respective (Z,Z)-isomer was found to be the most active in all... (More)
Under an artificial light: dark cycle, females of Lampronia capitella were observed calling, with extended terminal abdominal segments, during the first 2 hr of the photoperiod. Extracts of terminal abdominal segments from females elicited large electroantennographic responses from male antennae. Gas chromatography with electroantennographic detection revealed three active peaks. Based on comparison of retention times and mass spectra of synthetic standards, these compounds were identified as (Z;Z)-9,11-tetradecadienol and the corresponding acetate and aldehyde. The electroantennographic activity of the four geometric isomers of all three compounds was investigated, and the respective (Z,Z)-isomer was found to be the most active in all cases. Aldehydes generally elicited larger antennal responses than alcohols, whereas acetates were the least active compounds. A subtractive trapping assay in the field, based on a 13: 26: 100 1 g mixture of (Z,Z)-9,11-tetradecadienal, (Z,Z)-9,11-tetradecadienyl acetate, and (Z,Z)-9,11-tetradecadienol confirmed that all three compounds are pheromone components. Subtraction of (Z,Z)-9,11-tetradecadienol from the blend completely eliminated its attractiveness, whereas the other two-component blends showed reduced activity. This is the first pheromone identification from the monotrysian superfamily Incurvarioidea, confirming that the common pheromones among ditrysian moths (long-chain fatty acid derivatives comprising alcohols, acetates, and aldehydes with one or more double bonds) is not an autapomorphy of Ditrysia, but a synapomorphy of the more advanced heteroneuran lineages. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Chemical Ecology
volume
30
issue
3
pages
643 - 658
publisher
Springer
external identifiers
  • wos:000220053300012
  • pmid:15139314
  • scopus:12144290766
ISSN
1573-1561
DOI
10.1023/B:JOEC.0000018635.40128.2e
language
English
LU publication?
yes
id
84edab44-5c2e-48f5-948b-4a5b3a8fcfa2 (old id 135853)
date added to LUP
2007-06-27 10:52:49
date last changed
2017-01-01 06:39:52
@article{84edab44-5c2e-48f5-948b-4a5b3a8fcfa2,
  abstract     = {Under an artificial light: dark cycle, females of Lampronia capitella were observed calling, with extended terminal abdominal segments, during the first 2 hr of the photoperiod. Extracts of terminal abdominal segments from females elicited large electroantennographic responses from male antennae. Gas chromatography with electroantennographic detection revealed three active peaks. Based on comparison of retention times and mass spectra of synthetic standards, these compounds were identified as (Z;Z)-9,11-tetradecadienol and the corresponding acetate and aldehyde. The electroantennographic activity of the four geometric isomers of all three compounds was investigated, and the respective (Z,Z)-isomer was found to be the most active in all cases. Aldehydes generally elicited larger antennal responses than alcohols, whereas acetates were the least active compounds. A subtractive trapping assay in the field, based on a 13: 26: 100 1 g mixture of (Z,Z)-9,11-tetradecadienal, (Z,Z)-9,11-tetradecadienyl acetate, and (Z,Z)-9,11-tetradecadienol confirmed that all three compounds are pheromone components. Subtraction of (Z,Z)-9,11-tetradecadienol from the blend completely eliminated its attractiveness, whereas the other two-component blends showed reduced activity. This is the first pheromone identification from the monotrysian superfamily Incurvarioidea, confirming that the common pheromones among ditrysian moths (long-chain fatty acid derivatives comprising alcohols, acetates, and aldehydes with one or more double bonds) is not an autapomorphy of Ditrysia, but a synapomorphy of the more advanced heteroneuran lineages.},
  author       = {Löfstedt, Christer and Zhu, Jun-Wei and Kozlov, Michail V and Buda, Vincas and Jirle, Erling and Hellqvist, Sven and Löfqvist, Jan and Plass, E and Franke, S and Francke, Wittko},
  issn         = {1573-1561},
  language     = {eng},
  number       = {3},
  pages        = {643--658},
  publisher    = {Springer},
  series       = {Journal of Chemical Ecology},
  title        = {Identification of the sex pheromone of the currant shoot borer, <i>Lampronia capitella</i>},
  url          = {http://dx.doi.org/10.1023/B:JOEC.0000018635.40128.2e},
  volume       = {30},
  year         = {2004},
}