Advanced

Species discrimination in five species of winter-flying geometrids (Lepidoptera) based on chirality of semiochemicals and flight season

Szöcs, G. ; Tóth, M. ; Francke, W. ; Schmidt, F. ; Philipp, P. ; König, W. A. ; Mori, K. ; Hansson, Bill S. and Löfstedt, C. LU (1993) In Journal of Chemical Ecology 19(11). p.2721-2735
Abstract

Enantiomer separation of (6 Z,9 Z)-cis-3,4-epoxynonadecadiene and (3 Z,9 Z)-cis-6,7-epoxynonadecadiene could be achieved using chiral high-resolution gas chromatography and a cyclodextrin-bond column. (3 Z,9 Z)-(6 R,7 S)-Epoxynonadecadiene was identified from ovipositor extracts of Colotois pen-Naria, while in Erannis defoliaria the 6 S,7 R-enantiomer was found. In field trapping tests pure synthetic enantiomers caught only conspecific males of these species. (3 Z,6 Z,9 Z)-Nonadecatriene was found in both species, while the presence of (3 Z,6 Z,9 Z)-heneicosatriene was indicated in C. Pennaria only. A 10:10:3 blend of (3 Z,9 Z)-(6 R,7 S)-epoxynonadecadiene, (3 Z,6 Z,9 Z)-heneicosatriene, and (3 Z,6 Z,9 Z)-nonadecatriene was found to be... (More)

Enantiomer separation of (6 Z,9 Z)-cis-3,4-epoxynonadecadiene and (3 Z,9 Z)-cis-6,7-epoxynonadecadiene could be achieved using chiral high-resolution gas chromatography and a cyclodextrin-bond column. (3 Z,9 Z)-(6 R,7 S)-Epoxynonadecadiene was identified from ovipositor extracts of Colotois pen-Naria, while in Erannis defoliaria the 6 S,7 R-enantiomer was found. In field trapping tests pure synthetic enantiomers caught only conspecific males of these species. (3 Z,6 Z,9 Z)-Nonadecatriene was found in both species, while the presence of (3 Z,6 Z,9 Z)-heneicosatriene was indicated in C. Pennaria only. A 10:10:3 blend of (3 Z,9 Z)-(6 R,7 S)-epoxynonadecadiene, (3 Z,6 Z,9 Z)-heneicosatriene, and (3 Z,6 Z,9 Z)-nonadecatriene was found to be optimal for catching C. Pennaria, while E. Defoliaria males were optimally caught by a 1:1 mixture of (3 Z,9 Z)-(6 S,7 R)-epoxynonadecadiene and (3 Z,6 Z,9 Z)-nona-decatriene. (6 Z,9 Z)-(3 S,4 R)-Epoxynonadecadiene was identified from ovipositor extracts of Agriopis (Erannis) aurantiaria. In field tests the pure enantiomer proved to be a highly specific sex attractant for both the late autumn/early winter flying A. Aurantiaria and the late winter/early spring flying A. Leucophearia. Males of Agriopis marginaria, which fly in late winter/early spring, were attracted to (3 Z,9 Z)-(6 S,7 R)-epoxynonadecadiene. The addition of (3 Z,6 Z,9 Z)-nonadecatriene to the S,R-enantiomer increased captures. Optimal catches were recorded with a 10:3 epoxide-hydrocarbon blend. Enantiomer specificity in all species was confirmed in EAG measurements.

(Less)
Please use this url to cite or link to this publication:
author
; ; ; ; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
(3 Z,9 Z)-(6 R,7 S)-epoxynonadecadiene, (3 Z,9 Z)-(6 S,7 R)-epoxynonadecadiene, (6 Z,9 Z)-(3 S,4 R)-epoxynonadecadiene, A. leucophearia, A. marginaria, Agriopis aurantiaria, Chirality, Colotois pennaria, electroantennogram, enantiomers, Erannis defoliaria, field trapping, Geometridae, Lepidoptera, sex pheromones
in
Journal of Chemical Ecology
volume
19
issue
11
pages
2721 - 2735
publisher
Springer
external identifiers
  • scopus:0027135070
ISSN
0098-0331
DOI
10.1007/BF00980703
project
Evolutionary mechanisms of pheromone divergence in Lepidoptera
language
English
LU publication?
yes
id
dff68238-a801-4dba-9b8e-5dcfd93e1b2c
date added to LUP
2020-05-26 17:11:13
date last changed
2020-06-09 12:12:40
@article{dff68238-a801-4dba-9b8e-5dcfd93e1b2c,
  abstract     = {<p>Enantiomer separation of (6 Z,9 Z)-cis-3,4-epoxynonadecadiene and (3 Z,9 Z)-cis-6,7-epoxynonadecadiene could be achieved using chiral high-resolution gas chromatography and a cyclodextrin-bond column. (3 Z,9 Z)-(6 R,7 S)-Epoxynonadecadiene was identified from ovipositor extracts of Colotois pen-Naria, while in Erannis defoliaria the 6 S,7 R-enantiomer was found. In field trapping tests pure synthetic enantiomers caught only conspecific males of these species. (3 Z,6 Z,9 Z)-Nonadecatriene was found in both species, while the presence of (3 Z,6 Z,9 Z)-heneicosatriene was indicated in C. Pennaria only. A 10:10:3 blend of (3 Z,9 Z)-(6 R,7 S)-epoxynonadecadiene, (3 Z,6 Z,9 Z)-heneicosatriene, and (3 Z,6 Z,9 Z)-nonadecatriene was found to be optimal for catching C. Pennaria, while E. Defoliaria males were optimally caught by a 1:1 mixture of (3 Z,9 Z)-(6 S,7 R)-epoxynonadecadiene and (3 Z,6 Z,9 Z)-nona-decatriene. (6 Z,9 Z)-(3 S,4 R)-Epoxynonadecadiene was identified from ovipositor extracts of Agriopis (Erannis) aurantiaria. In field tests the pure enantiomer proved to be a highly specific sex attractant for both the late autumn/early winter flying A. Aurantiaria and the late winter/early spring flying A. Leucophearia. Males of Agriopis marginaria, which fly in late winter/early spring, were attracted to (3 Z,9 Z)-(6 S,7 R)-epoxynonadecadiene. The addition of (3 Z,6 Z,9 Z)-nonadecatriene to the S,R-enantiomer increased captures. Optimal catches were recorded with a 10:3 epoxide-hydrocarbon blend. Enantiomer specificity in all species was confirmed in EAG measurements.</p>},
  author       = {Szöcs, G. and Tóth, M. and Francke, W. and Schmidt, F. and Philipp, P. and König, W. A. and Mori, K. and Hansson, Bill S. and Löfstedt, C.},
  issn         = {0098-0331},
  language     = {eng},
  month        = {11},
  number       = {11},
  pages        = {2721--2735},
  publisher    = {Springer},
  series       = {Journal of Chemical Ecology},
  title        = {Species discrimination in five species of winter-flying geometrids (Lepidoptera) based on chirality of semiochemicals and flight season},
  url          = {http://dx.doi.org/10.1007/BF00980703},
  doi          = {10.1007/BF00980703},
  volume       = {19},
  year         = {1993},
}