Discovery of tetrasubstituted pyrazines as semiochemicals in a sexually deceptive orchid
Date
2012
Authors
Bohman, Bjorn
Jeffares, Lynne
Flematti, Gavin
Byrne, Lindsay T.
Skelton, Brian
Phillips, Ryan
Dixon, Kingsley
Peakall, Rodney
Barrow, Russell
Journal Title
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Volume Title
Publisher
American Chemical Society
Abstract
Sexually deceptive orchids employ mimicry of insect sex pheromones to exploit a diverse group of pollinators. The chemical structures of five semiochemicals (1-3, 7, 8) produced by populations of the warty hammer orchid, Drakaea livida, pollinated by a thynnine wasp in the genus Catocheilus were elucidated. With the exception of (2,5-dimethylpyrazin-3-yl)methyl 3-methylbutanoate (7), all active compounds were tetrasubstituted pyrazines, including hydroxymethyl (1) and ester (2 and 3) trimethylpyrazine derivatives. Male Catocheilus wasps were responsive to all of these compounds in GC-EAD experiments.
Description
Keywords
Keywords: butyric acid derivative; ester derivative; hydroxyl group; methyl group; pyrazine derivative; sex pheromone; analytic method; article; electroantennographic detection; gas chromatography; heteronuclear multiple bond correlation; heteronuclear single quant
Citation
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Source
Journal of Natural Products
Type
Journal article
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Restricted until
2037-12-31