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J Chem Ecol

Title:		"Purification, stereoisomeric analysis and quantification of sex pheromone precursors in female whole body extracts from pine sawfly species"
Author(s):		Bang J; Hedenstrom E; Sjodin K;
Address:		"Department of Natural Sciences, Engineering and Mathematics, Mid Sweden University, Sundsvall, Sweden"
Journal Title:		J Chem Ecol
Year:		2011
Volume:		20101126
Issue:		1
Page Number:		125 - 133
DOI:		10.1007/s10886-010-9886-z
ISSN/ISBN:		1573-1561 (Electronic) 0098-0331 (Linking)
Abstract:		"A GC-MS method to analyze the stereoisomeric composition of chiral secondary alcohols found in whole body extracts of pine sawfly females was developed. The tested alcohols were derivatized with optically pure (S)-2-acetoxypropionyl chloride prior to GC-MS analysis. Baseline separation was obtained for all sixteen stereoisomers of 3,7,9-trimethyltridecan-2-ol and for the four 3-methylpentadecan-2-ol stereoisomers. For 3,7-dimethyltridecan-2-ol, 3,7-dimethyltetradecan-2-ol and 3,7-dimethylpentadecan-2-ol baseline separation was obtained for 6 of the possible 8 stereoisomers. When a mixture of 16 stereoisomers of 3,7,11-trimethyltridecan-2-ol was tested, baseline separation of 7 peaks out of 16 possible was obtained. The investigated alcohols are pheromone precursors for some pine sawfly species that are severe defoliators of pine. Females from several Diprion, Neodiprion, Macrodiprion, Microdiprion, and Gilpinia species emit esters of such secondary alcohols as sex pheromones that attract males for mating. To quantify the small amounts of the precursor alcohol and its stereoisomeric composition found in whole body extracts from female pine sawflies, a purification method was optimized. An extract of 20 females of D. pini contained about 8 ng of (2S,3R,7R)-3,7-dimethyltridecan-2-ol per female, and three extracts of 18, 20, and 90 females of N. sertifer contained between 5 and 13 ng of (2S,3S,7S)-3,7-dimethylpentadecan-2-ol per female"
Keywords:		Animals Diptera/*chemistry Female Gas Chromatography-Mass Spectrometry Sex Attractants/analysis/chemistry/*isolation & purification Stereoisomerism;
Notes:		"MedlineBang, Joakim Hedenstrom, Erik Sjodin, Kristina eng Research Support, Non-U.S. Gov't 2010/11/27 J Chem Ecol. 2011 Jan; 37(1):125-33. doi: 10.1007/s10886-010-9886-z. Epub 2010 Nov 26"