Species discrimination in five species of winter-flying geometrids (Lepidoptera) based on chirality of semiochemicals and flight season
(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)
- author
- Szöcs, G. ; Tóth, M. ; Francke, W. ; Schmidt, F. ; Philipp, P. ; König, W. A. ; Mori, K. ; Hansson, Bill S. and Löfstedt, C. LU
- organization
- publishing date
- 1993-11-01
- 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
- 2021-01-06 05:59:51
@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}},
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}},
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}},
}