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J Chem Ecol

Title:		"Determination of the stereochemistry of the aggregation pheromone of harlequin bug, Murgantia histrionica"
Author(s):		Khrimian A; Shirali S; Vermillion KE; Siegler MA; Guzman F; Chauhan K; Aldrich JR; Weber DC;
Address:		"US Department of Agriculture, Agricultural Research Service, Invasive Insect Biocontrol and Behavior Laboratory, Beltsville, MD, 20705, USA, ashot.khrimian@ars.usda.gov"
Journal Title:		J Chem Ecol
Year:		2014
Volume:		20141119
Issue:		11-Dec
Page Number:		1260 - 1268
DOI:		10.1007/s10886-014-0521-2
ISSN/ISBN:		1573-1561 (Electronic) 0098-0331 (Linking)
Abstract:		"Preparation of a complete stereoisomeric library of 1,10-bisaboladien-3-ols and selected 10,11-epoxy-1-bisabolen-3-ols was pivotal for the identification of the aggregation pheromone of the brown marmorated stink bug, Halyomorpha halys. Herein, we describe syntheses of the remaining 10,11-epoxy-1-bisabolen-3-ols, and provide additional evidence on the assignment of relative and absolute configurations of these compounds by single-crystal X-ray crystallography of an intermediate, (3S,6R,7R,10S)-1-bisabolen-3,10,11-triol. To demonstrate the utility of this stereoisomeric library, we revisited the aggregation pheromone of the harlequin bug, Murgantia histrionica, and showed that the male-produced pheromone consists of two stereoisomers of 10,11-epoxy-1-bisabolen-3-ol. Employment of eight cis-10,11-epoxy-1-bisabolen-3-ol stereoisomeric standards, two enantioselective GC columns, and NMR spectroscopy enabled the identification of these compounds as (3S,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol and (3S,6S,7R,10R)-10,11-epoxy-1-bisabolen-3-ol, which are produced by M. histrionica males in 1.4:1 ratio"
Keywords:		"Animals *Chemotaxis Chromatography, Gas Crystallography, X-Ray Heteroptera/growth & development/*physiology Male Pheromones/*metabolism Stereoisomerism;"
Notes:		"MedlineKhrimian, Ashot Shirali, Shyam Vermillion, Karl E Siegler, Maxime A Guzman, Filadelfo Chauhan, Kamlesh Aldrich, Jeffrey R Weber, Donald C eng 2014/11/20 J Chem Ecol. 2014 Dec; 40(11-12):1260-8. doi: 10.1007/s10886-014-0521-2. Epub 2014 Nov 19"