Determination by HPLC fluorescence analysis of the natural enantiomers of sex pheromones in the New World screwworm fly,Cochliomyia hominivorax
| Autor: | T. Ohtaka, Dennis R. Berkebile, David A. Carlson, K. Akasaka, H. Ohrui, K. Mori |
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| Rok vydání: | 2009 |
| Předmět: |
Male
Ketone Fluorescence Hydrolysis Hplc fluorescence Alkanes Botany Animals Bioassay Sex Attractants Chromatography High Pressure Liquid Ecology Evolution Behavior and Systematics Anthracenes chemistry.chemical_classification Chromatography General Veterinary biology Natural materials Diptera biology.organism_classification Screw Worm Infection chemistry Insect Science Sex pheromone Female Indicators and Reagents Parasitology Enantiomer Cochliomyia hominivorax Chromatography Liquid |
| Zdroj: | Medical and Veterinary Entomology. 23:126-130 |
| ISSN: | 1365-2915 0269-283X |
| DOI: | 10.1111/j.1365-2915.2008.00781.x |
| Popis: | 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 nona- cosanes 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 derivatiza- tion 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 (6 R ,19 R )- 6-acetoxy-19-methylnonanocosane, and (7 R ,15 R )- and (7 R ,15 S )-7-acetoxy-15-methyl- nonanocosane were detected in extracts of recently colonized female flies. |
| Databáze: | OpenAIRE |
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