Journal of Chemical Ecology (2002) 28, 1839-1852

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Qing-He Zhang, Till Tolasch, Fredrik Schlyter and Wittko Francke (2002)
Enantiospecific antennal response of bark beetles to spiroacetal (E)-conophthorin
Journal of Chemical Ecology 28 (9), 1839-1852
Abstract: Optically pure synthetic enantiomers of (E)-conophthorin [(E)-7-methyl-1,6-dioxaspiro[4.5]decane], one of the volatiles affecting coniferophagous bark beetles, were tested on antennae of Ips typographus, I. duplicatus, I. subelongatus, Dendroctonus micans, and five Scolytus spp. by using combined gas chromatography-electroantennographic detection (GC-EAD). EAD dose-responses indicated that all three Ips species perceived only the naturally occurring and quantitatively dominant (5S,7S)-enantiomer, while its antipode, (5R,7R)-(E)-conophthorin was antennally inactive. Response thresholds for the Ips species were estimated as between 0.1 ng and 1 ng, or lower. The antennal responses of the Ips species caused by 100 ng of the (5R,7R)-enantiomer might be due to 1% impurity-(the active (5S,7S)-enantiomer) in the (5R,7R)-sample. At the 50-ng level, D. micans and five angiosperm Scolytus species (S. intracatus, S. mali, S. ratzeburgi, S. rugulosus, and S. scolytus) responded strongly to the (5S,7S)-enantiomer, while the (5R,7R)-enantiomer was antennally inactive. Currently updated knowledge on the natural occurrence, and electrophysiological and behavioral activity of (E)-conophthorin is summarized.
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Database assignments for author(s): Qing He Zhang, Fredrik Schlyter

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Scolytus rugulosus
Scolytus scolytus
Scolytus mali
Dendroctonus micans
Ips typographus
Ips subelongatus
Ips duplicatus