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Sci Rep

Title:		"Stereochemistry of two pheromonal components of the bumblebee wax moth, Aphomia sociella"
Author(s):		Wallin EA; Kalinova B; Kindl J; Hedenstrom E; Valterova I;
Address:		"Mid Sweden University, Department of Chemical Engineering, SE-851 70, Sundsvall, Sweden. Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Research Group of Infochemicals, 166 10, Prague, Czech Republic. Faculty of Forestry and Wood Sciences, Extemit-K group, Czech University of Life Sciences, 165 21, Prague, Czech Republic. Faculty of Forestry and Wood Sciences, Department of Forest Protection and Entomology, Czech University of Life Sciences, 165 21, Prague, Czech Republic. Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Research Group of Infochemicals, 166 10, Prague, Czech Republic. irena@uochb.cas.cz. Faculty of Tropical AgriSciences, Department of Crop Sciences and Agroforestry, Czech University of Life Sciences, 165 21, Prague, Czech Republic. irena@uochb.cas.cz"
Journal Title:		Sci Rep
Year:		2020
Volume:		20200207
Issue:		1
Page Number:		2094 -
DOI:		10.1038/s41598-020-59069-1
ISSN/ISBN:		2045-2322 (Electronic) 2045-2322 (Linking)
Abstract:		"The bumblebee wax moth, Aphomia sociella, is a parasite of bumblebees. In this species, males produce sexual pheromone to attract females, while females produce an aphrodisiac pheromone that initiates male courtship. Both pheromones contain 6,10,14-trimethylpentadecan-2-one (TMPD-one) and the corresponding alcohol, 6,10,14-trimethylpentadecan-2-ol (TMPD-ol) in sex specific quantities. Male sex pheromone consists of 7 components with TMPD-one as a minor one and traces of TMPD-ol. In female aphrodisiac pheromone, TMPD-ol is the major component, while TMPD-one is present in traces. Here we report on the absolute configuration of TMPD-one in male sex pheromone and TMPD-ol in female aphrodisiac pheromone of A. sociella. The configuration was determined from GC/MS of prepared (S)-acetoxypropionyl esters of TMPD-ol. TMPD-one was first reduced to the alcohol that was then derivatized with (S)-acetoxypropionyl chloride. The GC/MS data of obtained diastereoisomers were compared with synthetic standards. The absolute configuration of TMPD-one in the male pheromone was (6R,10R). The configuration of TMPD-ol in the female pheromone was (2R,6R,10R). Electrophysiological experiments showed that TMPD-one and TMPD-ol are perceived by both sexes. The synthetic standards of naturally produced stereoisomers elicited higher responses than mixtures of all stereoisomers"
Keywords:		Animals Female Gas Chromatography-Mass Spectrometry Male Moths/*metabolism Sex Attractants/*chemistry/isolation & purification Stereoisomerism;
Notes:		"MedlineWallin, Erika A Kalinova, Blanka Kindl, Jiri Hedenstrom, Erik Valterova, Irena eng Research Support, Non-U.S. Gov't England 2020/02/09 Sci Rep. 2020 Feb 7; 10(1):2094. doi: 10.1038/s41598-020-59069-1"