Male-Specific Sesquiterpenes from Phyllotreta Flea Beetles
| Autor: | Bruce W. Zilkowski, Udo Schnupf, Allard A. Cossé, Karl E. Vermillion, Robert J. Bartelt, Frank A. Momany |
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| Rok vydání: | 2011 |
| Předmět: |
Male
Flea Pharmaceutical Science Brassica Sesquiterpene Gas Chromatography-Mass Spectrometry Pheromones Analytical Chemistry Electroantennography chemistry.chemical_compound Drug Discovery Botany Animals Pest Control Biological Pharmacology Flea beetle Molecular Structure biology Organic Chemistry biology.organism_classification Terpenoid Coleoptera Chemical ecology Complementary and alternative medicine chemistry Sex pheromone Molecular Medicine Pheromone Female Sesquiterpenes |
| Zdroj: | Journal of Natural Products. 74:585-595 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/np100608p |
| Popis: | Flea beetles in several genera are known to possess male-specific sesquiterpenes, at least some of which serve as aggregation pheromones that attract both sexes. In continuing research on the chemical ecology of Phyllotreta flea beetles, six new male-specific sesquiterpenes were identified, one from P. striolata (hydroxyketone 9) and five from P. pusilla (aldehydes 10-12 and 14 and alcohol 13); both species are crop pests. The minute amounts from beetles provided mass spectra and chromatographic data but were insufficient for complete structure determination. However, it was discovered that the new compounds could all be produced by applying organic reactions to previously identified flea beetle sesquiterpenes, and the resulting, larger amounts of material permitted definitive structure analysis by NMR. Molecular modeling was used in conjunction with NMR to define relative configurations of several newly created stereogenic centers. The absolute configurations of natural 9-14 were established by chiral gas chromatography/mass spectrometry. In electrophysiological tests (GC-EAD) conducted with P. striolata, compound 9 was detected with high sensitivity by the beetle antennae, which is consistent with a pheromonal function. The research opens new possibilities for using behavioral chemicals to monitor or manage these pest species. |
| Databáze: | OpenAIRE |
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