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Pheromonal Production of and Response to Optically Active Epoxydienes in Some Ceometrid Moths (Lepidoptera: Geometridae)

Tóth, Miklos ; Szöcs, Gabor ; Francke, Wittko ; Schmidt, F. ; Philipp, P. ; Lofstedt, C. LU ; Hansson, Bill S. and Farag, A. I. (1994) In Zeitschrift fur Naturforschung - Section C Journal of Biosciences 49(7-8). p.516-521
Abstract

In, pheromone extracts of calling female Chiasma clathrata, L. (Lepidoptera: Geometridae), a defoliator pest of alfalfa, (Z,Z,Z)-3,6,9–heptadecatriene and (Z,Z)-6,9–cis-3,4–epoxyhepta-decadiene was identified. Chiral gas chromatography using a modified cyclodextrin and synthetic reference samples proved the natural epoxide to show (3 R.4 S)-configuration. In field trapping tests, only the pure (3/R,4S)-enantiomer of the epoxide attracted males. The addition of the triene component was synergistic. Males of the sympatric species Tephrina arenaceciria Hbn. (Lepidoptera: Geometridae) were caught only in traps with baits containing the (3S,4R)-enantiomer [together with a previously described minor component,... (More)

In, pheromone extracts of calling female Chiasma clathrata, L. (Lepidoptera: Geometridae), a defoliator pest of alfalfa, (Z,Z,Z)-3,6,9–heptadecatriene and (Z,Z)-6,9–cis-3,4–epoxyhepta-decadiene was identified. Chiral gas chromatography using a modified cyclodextrin and synthetic reference samples proved the natural epoxide to show (3 R.4 S)-configuration. In field trapping tests, only the pure (3/R,4S)-enantiomer of the epoxide attracted males. The addition of the triene component was synergistic. Males of the sympatric species Tephrina arenaceciria Hbn. (Lepidoptera: Geometridae) were caught only in traps with baits containing the (3S,4R)-enantiomer [together with a previously described minor component, (Z,Z)-3,9–cis-6,7–epoxyheptadecadiene], In trapping tests conducted iNADifferent biotope Abraxas grossu-lariata, L. (Lepidoptera: Geometridae) males were attracted by the (3S,4R)-enantiomer, whereas the (3/L4S)-enantiomer attracted a close relative. Abraxas sylvata Scop. (Lepidoptera: Geometridae). The present results suggest that one of the key mechanisms responsible for pheromone specificity among both the two alfalfa geometrids and the two Abraxas species in their respective biotops, may be the use of different enantiomers of the same polyene-derived epoxide as a sex pheromone component. It is probable that this discrimination mechanism is widespread among moth species utilizing epoxide pheromone components.

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organization
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Contribution to journal
publication status
published
subject
keywords
(Z,Z)-69-ds-3, 4-Epoxyheptadecadiene (ZZZ)-3,6,9-Heptadecatriene, Enantiomers, Isolation, Reproductive, Sex Pheromone
in
Zeitschrift fur Naturforschung - Section C Journal of Biosciences
volume
49
issue
7-8
pages
516 - 521
publisher
Verlag der Zeitschrift für Naturforschung
external identifiers
  • scopus:0028002723
ISSN
0939-5075
DOI
10.1515/znc-1994-7-819
project
Evolutionary mechanisms of pheromone divergence in Lepidoptera
language
English
LU publication?
yes
id
7911d043-8053-4803-b1b3-7dbd8beac245
date added to LUP
2020-05-26 16:48:37
date last changed
2020-06-08 08:19:38
@article{7911d043-8053-4803-b1b3-7dbd8beac245,
  abstract     = {<p>In, pheromone extracts of calling female Chiasma clathrata, L. (Lepidoptera: Geometridae), a defoliator pest of alfalfa, (Z,Z,Z)-3,6,9–heptadecatriene and (Z,Z)-6,9–cis-3,4–epoxyhepta-decadiene was identified. Chiral gas chromatography using a modified cyclodextrin and synthetic reference samples proved the natural epoxide to show (3 R.4 S)-configuration. In field trapping tests, only the pure (3/R,4S)-enantiomer of the epoxide attracted males. The addition of the triene component was synergistic. Males of the sympatric species Tephrina arenaceciria Hbn. (Lepidoptera: Geometridae) were caught only in traps with baits containing the (3S,4R)-enantiomer [together with a previously described minor component, (Z,Z)-3,9–cis-6,7–epoxyheptadecadiene], In trapping tests conducted iNADifferent biotope Abraxas grossu-lariata, L. (Lepidoptera: Geometridae) males were attracted by the (3S,4R)-enantiomer, whereas the (3/L4S)-enantiomer attracted a close relative. Abraxas sylvata Scop. (Lepidoptera: Geometridae). The present results suggest that one of the key mechanisms responsible for pheromone specificity among both the two alfalfa geometrids and the two Abraxas species in their respective biotops, may be the use of different enantiomers of the same polyene-derived epoxide as a sex pheromone component. It is probable that this discrimination mechanism is widespread among moth species utilizing epoxide pheromone components.</p>},
  author       = {Tóth, Miklos and Szöcs, Gabor and Francke, Wittko and Schmidt, F. and Philipp, P. and Lofstedt, C. and Hansson, Bill S. and Farag, A. I.},
  issn         = {0939-5075},
  language     = {eng},
  month        = {08},
  number       = {7-8},
  pages        = {516--521},
  publisher    = {Verlag der Zeitschrift für Naturforschung},
  series       = {Zeitschrift fur Naturforschung - Section C Journal of Biosciences},
  title        = {Pheromonal Production of and Response to Optically Active Epoxydienes in Some Ceometrid Moths (Lepidoptera: Geometridae)},
  url          = {http://dx.doi.org/10.1515/znc-1994-7-819},
  doi          = {10.1515/znc-1994-7-819},
  volume       = {49},
  year         = {1994},
}