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J Nat Prod

Title:		Male-specific sesquiterpenes from Phyllotreta flea beetles
Author(s):		Bartelt RJ; Zilkowski BW; Cosse AA; Schnupf U; Vermillion K; Momany FA;
Address:		"USDA Agricultural Research Service, National Center for Agricultural Utilization Research, 1815 North University Street, Peoria, Illinois 61604, USA. Robert.Bartelt@sbcglobal.net"
Journal Title:		J Nat Prod
Year:		2011
Volume:		20110222
Issue:		4
Page Number:		585 - 595
DOI:		10.1021/np100608p
ISSN/ISBN:		1520-6025 (Electronic) 0163-3864 (Linking)
Abstract:		"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"
Keywords:		"Animals Brassica/parasitology Coleoptera/*chemistry/*physiology Female Gas Chromatography-Mass Spectrometry Male Molecular Structure *Pest Control, Biological Pheromones/chemistry/*isolation & purification/*physiology Sesquiterpenes/chemistry/*isolation &;"
Notes:		"MedlineBartelt, Robert J Zilkowski, Bruce W Cosse, Allard A Schnupf, Udo Vermillion, Karl Momany, Frank A eng 2011/02/24 J Nat Prod. 2011 Apr 25; 74(4):585-95. doi: 10.1021/np100608p. Epub 2011 Feb 22"