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Med Vet Entomol

Title:		"Determination by HPLC fluorescence analysis of the natural enantiomers of sex pheromones in the New World screwworm fly, Cochliomyia hominivorax"
Author(s):		Akasaka K; Carlson DA; Ohtaka T; Ohrui H; Mori K; Berkebile DR;
Address:		"Graduate School of Life Sciences, Tohoku University, Sendai, Miyagi, Japan"
Journal Title:		Med Vet Entomol
Year:		2009
Volume:		23 Suppl 1
Issue:
Page Number:		126 - 130
DOI:		10.1111/j.1365-2915.2008.00781.x
ISSN/ISBN:		1365-2915 (Electronic) 0269-283X (Linking)
Abstract:		"Bioassays of six racemic synthesized candidate sex pheromone compounds against male New World screwworm Cochliomyia hominivorax (Coquerel) flies showed that the most potent bioactivity was found with 6-acetoxy-19-methylnonacosane and 7-acetoxy-15-methylnonacosane compared with four other isomeric acetoxy nonacosanes and a larger aliphatic ketone. As all these methyl-branched compounds have two asymmetric carbons and four possible enantiomers, characterization of the natural enantiomers was essential. All four enantiomers for the two most bioactive isomers of the natural sex pheromone were synthesized for bioassay. Hydrolysis and derivatization of these enantiomers with different fluorescent reagents was followed by column-switched high-performance liquid chromatography. The use of two linked, reversed-phase columns of different polarity held at sub-ambient temperatures allowed good separation of each enantiomer. This analysis applied to natural material was successful, as (6R,19R)-6-acetoxy-19-methylnonanocosane, and (7R,15R)- and (7R,15S)-7-acetoxy-15-methylnonanocosane were detected in extracts of recently colonized female flies"
Keywords:		"Alkanes/analysis Animals Anthracenes/analysis Chromatography, High Pressure Liquid Chromatography, Liquid Diptera/pathogenicity/*physiology Female Fluorescence Indicators and Reagents Male Screw Worm Infection/veterinary Sex Attractants/*chemistry/*isolat;"
Notes:		"MedlineAkasaka, K Carlson, D A Ohtaka, T Ohrui, H Mori, K Berkebile, D R eng Research Support, Non-U.S. Gov't England 2009/04/02 Med Vet Entomol. 2009 Jun; 23 Suppl 1:126-30. doi: 10.1111/j.1365-2915.2008.00781.x"