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Naturwissenschaften

Title:		Anatomical localization and stereoisomeric composition of Tribolium castaneum aggregation pheromones
Author(s):		Lu Y; Beeman RW; Campbell JF; Park Y; Aikins MJ; Mori K; Akasaka K; Tamogami S; Phillips TW;
Address:		"Department of Entomology, Kansas State University, Manhattan, KS 66506, USA"
Journal Title:		Naturwissenschaften
Year:		2011
Volume:		20110804
Issue:		9
Page Number:		755 - 761
DOI:		10.1007/s00114-011-0824-x
ISSN/ISBN:		1432-1904 (Electronic) 0028-1042 (Linking)
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 degrees 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"
Keywords:		"Aldehydes/chemistry Animals Chromatography, High Pressure Liquid Epidermis/metabolism Male Pheromones/*chemistry Stereoisomerism Tribolium/*anatomy & histology/*chemistry/metabolism;"
Notes:		"MedlineLu, Yujie Beeman, Richard W Campbell, James F Park, Yoonseong Aikins, Michael J Mori, Kenji Akasaka, Kazuaki Tamogami, Shigeyuki Phillips, Thomas W eng Research Support, U.S. Gov't, Non-P.H.S. Germany 2011/08/05 Naturwissenschaften. 2011 Sep; 98(9):755-61. doi: 10.1007/s00114-011-0824-x. Epub 2011 Aug 4"