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Sex pheromone components of the turnip moth, Agrotis segetum - Chemical identification, electrophysiological evaluation and behavioral activity

Löfstedt, Christer LU ; Van Der Pers, Jan N.C. ; Löfqvist, Jan ; Lanne, Boel S. ; Appelgren, Monica ; Bergström, Gunnar and Thelin, Bernt (1982) In Journal of Chemical Ecology 8(10). p.1305-1321
Abstract

Analysis of female abdominal tips of Agrotis segetum by means of GC-MS showed the presence of 13 aliphatic acetates and alcohols. (Z)-7-Dodecenyl acetate was found to be the main component in the extracts at amounts of about 1 ng/female. (Z)-9-Tetradecenyl acetate and (Z)-7-dodecenol were present to the extent of 49 and 19%, respectively, of the main component. Minor components could be identified as decyl acetate, (Z)-5-decenyl acetate, dodecyl acetate, (Z)-9-dodecenyl acetate, tetradecyl acetate, a tetradecenyl acetate, hexadecyl acetate, a hexadecenyl acetate, (Z)-5-decenol, and (Z)-9-tetradecenol. The presence and biological activity of decyl acetate, (Z)-5-decenyl acetate, and (Z)-7-dodecenyl acetate in the extracts could be... (More)

Analysis of female abdominal tips of Agrotis segetum by means of GC-MS showed the presence of 13 aliphatic acetates and alcohols. (Z)-7-Dodecenyl acetate was found to be the main component in the extracts at amounts of about 1 ng/female. (Z)-9-Tetradecenyl acetate and (Z)-7-dodecenol were present to the extent of 49 and 19%, respectively, of the main component. Minor components could be identified as decyl acetate, (Z)-5-decenyl acetate, dodecyl acetate, (Z)-9-dodecenyl acetate, tetradecyl acetate, a tetradecenyl acetate, hexadecyl acetate, a hexadecenyl acetate, (Z)-5-decenol, and (Z)-9-tetradecenol. The presence and biological activity of decyl acetate, (Z)-5-decenyl acetate, and (Z)-7-dodecenyl acetate in the extracts could be detected by GC-EAD. Tested by EAG (Z)-5-decenyl acetate evoked the highest response among pheromone candidates, followed by (E)-5-decenyl acetate and (Z)-7-dodecenyl acetate. Single-cell recordings from 100 male antennal sensilla trichodea revealed receptorcells highly sensitive to (Z)-5-decenyl, (Z)-7-dodecenyl, (Z)-8-dodecenyl, and (Z)-9-tetradecenyl acetate as well as (Z)-5-decenol. The (Z)-5-decenyl, (Z)-7-dodecenyl, and (Z)-9-tetradecenyl acetate receptors were activated significantly also by female extracts. When tested in a tube olfactometer, a blend of decyl, (Z)-5-decenyl, (Z)-7-dodecenyl, and (Z)-9-tetradecenyl acetate evoked the same male response as did female glands. Tested in the field, this blend was more attractive than virgin females. Other authors previously reported many of the compounds identified in the present study. However, both quantitative and qualitative discrepancies exist among the various investigations, possibly due to the existence of geographical races.

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author
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organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Agrotis segetum, behavior, electroantennography, entrainment, gas chromatography-mass spectrometry, Lepidoptera, Noctuidae, sex pheromone, single-cell recordings, straight-chain acetates, turnip moth
in
Journal of Chemical Ecology
volume
8
issue
10
pages
1305 - 1321
publisher
Springer
external identifiers
  • scopus:0000604552
ISSN
0098-0331
DOI
10.1007/BF00987764
project
Evolutionary mechanisms of pheromone divergence in Lepidoptera
language
English
LU publication?
yes
id
428e0b49-8822-44de-8b46-ee0c66c7e5b4
date added to LUP
2020-07-23 16:03:47
date last changed
2020-09-23 15:07:21
@article{428e0b49-8822-44de-8b46-ee0c66c7e5b4,
  abstract     = {<p>Analysis of female abdominal tips of Agrotis segetum by means of GC-MS showed the presence of 13 aliphatic acetates and alcohols. (Z)-7-Dodecenyl acetate was found to be the main component in the extracts at amounts of about 1 ng/female. (Z)-9-Tetradecenyl acetate and (Z)-7-dodecenol were present to the extent of 49 and 19%, respectively, of the main component. Minor components could be identified as decyl acetate, (Z)-5-decenyl acetate, dodecyl acetate, (Z)-9-dodecenyl acetate, tetradecyl acetate, a tetradecenyl acetate, hexadecyl acetate, a hexadecenyl acetate, (Z)-5-decenol, and (Z)-9-tetradecenol. The presence and biological activity of decyl acetate, (Z)-5-decenyl acetate, and (Z)-7-dodecenyl acetate in the extracts could be detected by GC-EAD. Tested by EAG (Z)-5-decenyl acetate evoked the highest response among pheromone candidates, followed by (E)-5-decenyl acetate and (Z)-7-dodecenyl acetate. Single-cell recordings from 100 male antennal sensilla trichodea revealed receptorcells highly sensitive to (Z)-5-decenyl, (Z)-7-dodecenyl, (Z)-8-dodecenyl, and (Z)-9-tetradecenyl acetate as well as (Z)-5-decenol. The (Z)-5-decenyl, (Z)-7-dodecenyl, and (Z)-9-tetradecenyl acetate receptors were activated significantly also by female extracts. When tested in a tube olfactometer, a blend of decyl, (Z)-5-decenyl, (Z)-7-dodecenyl, and (Z)-9-tetradecenyl acetate evoked the same male response as did female glands. Tested in the field, this blend was more attractive than virgin females. Other authors previously reported many of the compounds identified in the present study. However, both quantitative and qualitative discrepancies exist among the various investigations, possibly due to the existence of geographical races.</p>},
  author       = {Löfstedt, Christer and Van Der Pers, Jan N.C. and Löfqvist, Jan and Lanne, Boel S. and Appelgren, Monica and Bergström, Gunnar and Thelin, Bernt},
  issn         = {0098-0331},
  language     = {eng},
  month        = {10},
  number       = {10},
  pages        = {1305--1321},
  publisher    = {Springer},
  series       = {Journal of Chemical Ecology},
  title        = {Sex pheromone components of the turnip moth, Agrotis segetum - Chemical identification, electrophysiological evaluation and behavioral activity},
  url          = {http://dx.doi.org/10.1007/BF00987764},
  doi          = {10.1007/BF00987764},
  volume       = {8},
  year         = {1982},
}