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Structure-activity relationships for chain-shortened analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth, Agrotis segetum

Bengtsson, Marie LU ; Liljefors, Tommy ; Hansson, Bill S. ; Löfstedt, Christer LU and Copaja, Sylvia V. (1990) In Journal of Chemical Ecology 16(3). p.667-684
Abstract

Structure-activity relationships for chain-shortened analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth, Agrotis segetum, have been studied by electrophysiological single-sensillum technique and interpreted in terms of a previously reported receptor-interaction model. The results indicate that the terminal methyl group, as well as the acetate group, interacts with highly complementary receptor sites. The terminal alkyl chain is suggested to interact with a hydrophobic "pocket" extending over the two methylene groups closest to the terminal methyl group. The amounts of stimulus actually released from the odor source have been studied. The results demonstrate the necessity to take differences of volatility into... (More)

Structure-activity relationships for chain-shortened analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth, Agrotis segetum, have been studied by electrophysiological single-sensillum technique and interpreted in terms of a previously reported receptor-interaction model. The results indicate that the terminal methyl group, as well as the acetate group, interacts with highly complementary receptor sites. The terminal alkyl chain is suggested to interact with a hydrophobic "pocket" extending over the two methylene groups closest to the terminal methyl group. The amounts of stimulus actually released from the odor source have been studied. The results demonstrate the necessity to take differences of volatility into account in comparisons of electrophysiological data for compounds of different chain lengths. It is shown that relative vapor pressures may to a good approximation be employed to estimate correction factors.

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author
; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
(Z)-5-decenyl acetate, Agrotis segetum, chain-shortened analogs, Lepidoptera, Noctuidae, receptor interaction, single-cell recordings, Structure-activity, vapor pressure, volatility
in
Journal of Chemical Ecology
volume
16
issue
3
pages
18 pages
publisher
Springer
external identifiers
  • scopus:0000386955
ISSN
0098-0331
DOI
10.1007/BF01016478
project
Evolutionary mechanisms of pheromone divergence in Lepidoptera
language
English
LU publication?
yes
id
b4ce6713-ed6d-41e3-9746-27d977fa7894
date added to LUP
2020-05-26 17:45:26
date last changed
2020-07-12 06:08:49
@article{b4ce6713-ed6d-41e3-9746-27d977fa7894,
  abstract     = {<p>Structure-activity relationships for chain-shortened analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth, Agrotis segetum, have been studied by electrophysiological single-sensillum technique and interpreted in terms of a previously reported receptor-interaction model. The results indicate that the terminal methyl group, as well as the acetate group, interacts with highly complementary receptor sites. The terminal alkyl chain is suggested to interact with a hydrophobic "pocket" extending over the two methylene groups closest to the terminal methyl group. The amounts of stimulus actually released from the odor source have been studied. The results demonstrate the necessity to take differences of volatility into account in comparisons of electrophysiological data for compounds of different chain lengths. It is shown that relative vapor pressures may to a good approximation be employed to estimate correction factors.</p>},
  author       = {Bengtsson, Marie and Liljefors, Tommy and Hansson, Bill S. and Löfstedt, Christer and Copaja, Sylvia V.},
  issn         = {0098-0331},
  language     = {eng},
  month        = {03},
  number       = {3},
  pages        = {667--684},
  publisher    = {Springer},
  series       = {Journal of Chemical Ecology},
  title        = {Structure-activity relationships for chain-shortened analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth, Agrotis segetum},
  url          = {http://dx.doi.org/10.1007/BF01016478},
  doi          = {10.1007/BF01016478},
  volume       = {16},
  year         = {1990},
}