Anatomical localization and stereoisomeric composition of Tribolium castaneum aggregation pheromones

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Show simple item record Yujie, Lu Beeman, Richard W. Campbell, James F. Park, Yoonseong Aikins, Michael J. Mori, Kenji Akasaka, Kazuaki Tamogami, Shigeyuki Phillips, Thomas W. 2011-10-19T15:05:08Z 2011-10-19T15:05:08Z 2011-10-19
dc.description.abstract We report that the abdominal epidermis and associated tissues are the predominant sources of male-produced pheromones in the red flour beetle, Tribolium castaneum and, for the first time, describe the stereoisomeric composition of the natural blend of isomers of the aggregation pheromone 4,8-dimethyldecanal (DMD) in this important pest species. Quantitative analyses via gas chromatography–mass spectrometry showed that the average amount of DMD released daily by single feeding males of T. castaneum was 878 ± 72 ng (SE). Analysis of different body parts identified the abdominal epidermis as the major source of aggregation pheromone; the thorax was a minor source, while no DMD was detectable in the head. No internal organs or obvious male-specific glands were associated with pheromone deposition. Complete separation of all four stereoisomers of DMD was achieved following oxidation to the corresponding acid, derivatization with (1R, 2R)- and (1S, 2S)-2-(anthracene-2,3-dicarboximido)cyclohexanol to diastereomeric esters, and their separation on reversed-phase high-performance liquid chromatography at −54°C. Analysis of the hexane eluate from Porapak-Q-collected volatiles from feeding males revealed the presence of all four isomers (4R,8R)/(4R,8S)/(4S,8R)/(4S,8S) at a ratio of approximately 4:4:1:1. A walking orientation bioassay in a wind tunnel with various blends of the four synthetic isomers further indicated that the attractive potency of the reconstituted natural blend of 4:4:1:1 was equivalent to that of the natural pheromone and greater than that of the 1:1 blend of (4R,8R)/(4R,8S) used in commercial lures. en_US
dc.relation.uri en_US
dc.subject Chirality en_US
dc.subject 4,8-Dimethyldecanal en_US
dc.subject Insect en_US
dc.subject Red flour beetle en_US
dc.subject Tribolium en_US
dc.subject Chemical ecology en_US
dc.subject Stored grain en_US
dc.title Anatomical localization and stereoisomeric composition of Tribolium castaneum aggregation pheromones en_US
dc.type Article (author version) en_US 2011 en_US
dc.citation.doi doi:10.1007/s00114-011-0824-x en_US
dc.citation.epage 761 en_US
dc.citation.issue 9 en_US
dc.citation.jtitle Naturwissenschaften en_US
dc.citation.spage 755 en_US
dc.citation.volume 98 en_US
dc.contributor.authoreid twp1 en_US
dc.contributor.authoreid rwbeeman en_US
dc.contributor.authoreid campbell en_US
dc.contributor.authoreid ypark en_US
dc.contributor.authoreid mja8338 en_US

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