Anatomical localization and stereoisomeric composi

Authors: Yujie Lu Richard W Beeman James F Campbell Yoonseong Park Michael J Aikins Kenji Mori Kazuaki Akasaka Shigeyuki Tamogami Thomas W Phillips

Publish Date: 2011/08/04

Volume: 98, Issue: 9, Pages: 755-

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Abstract

We report that the abdominal epidermis and associated tissues are the predominant sources of maleproduced 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 48dimethyldecanal 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 malespecific 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 2S2anthracene23dicarboximidocyclohexanol to diastereomeric esters and their separation on reversedphase highperformance liquid chromatography at −54°C Analysis of the hexane eluate from PorapakQcollected volatiles from feeding males revealed the presence of all four isomers 4R8R/4R8S/4S8R/4S8S at a ratio of approximately 4411 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 4411 was equivalent to that of the natural pheromone and greater than that of the 11 blend of 4R8R/4R8S used in commercial luresThe authors thank Alain VanRyckeghem Insects Limited Westfield IN for providing an authentic standard of DMD as a GC standard and David Hagstrum Lee Cohnstaedt and Jim Throne for constructive reviews Partial funding for this research came from the Kansas Agricultural Experiment Station and the USDA Risk Avoidance and Mitigation Program Mention of trade names or commercial products in this publication is solely for the purpose of providing specific information and does not imply recommendation or endorsement by the US Department of Agriculture or Kansas State University USDA is an equalopportunity provider and employer

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