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J Agric Food Chem

Title:		"Analysis of 2,4,6-nonatrienal geometrical isomers from male flea beetles, Epitrix hirtipennis and E. fuscula"
Author(s):		Zilkowski BW; Bartelt RJ; Vermillion K;
Address:		"USDA-ARS National Center for Agricultural Utilization Research, 1815 North University Street, Peoria, Illinois 61604, USA. Bruce.Zilkowski@ars.usda.gov"
Journal Title:		J Agric Food Chem
Year:		2008
Volume:		20080614
Issue:		13
Page Number:		4982 - 4986
DOI:		10.1021/jf8005273
ISSN/ISBN:		1520-5118 (Electronic) 0021-8561 (Linking)
Abstract:		"Geometrical isomers of 2,4,6-nonatrienal have been reported from a variety of food- and insect-related sources. It was discovered recently that the eggplant flea beetle, Epitrix fuscula, uses the (2 E,4 E,6 Z) and (2 E,4 E,6 E) isomers as components of its male-produced aggregation pheromone. Here, we learned that the related species, E. hirtipennis, also emits a blend of 2,4,6-nonatrienals, including isomers not previously characterized. Patterns in emission and response suggest a pheromonal function. In an effort to acquire standards to aid in identification, we found that exposing (2 E,4 E,6 E)-2,4,6-nonatrienal (or other available 2,4,6-nonatrienals) to light readily generated a mixture of six geometrical isomers. Configurations of these were determined by NMR, and chromatographic properties (GC and HPLC) were documented. On the basis of chromatographic comparison to these standards, the most abundant, new compound from E. hirtipennis was concluded to be (2 E,4 Z,6 Z)-2,4,6-nonatrienal. Minor components from both E. hirtipennis and E. fuscula were also characterized. The analytical approach given here would also be of use in the food industry, where 2,4,6-nonatrienals are important as aroma compounds"
Keywords:		"Animals Chromatography, High Pressure Liquid Coleoptera/*chemistry/physiology Isomerism Male Mass Spectrometry Nuclear Magnetic Resonance, Biomolecular Pheromones/*chemistry/metabolism Reference Standards alpha-Linolenic Acid/*analogs & derivatives/chemis;"
Notes:		"MedlineZilkowski, Bruce W Bartelt, Robert J Vermillion, Karl eng Comparative Study 2008/06/17 J Agric Food Chem. 2008 Jul 9; 56(13):4982-6. doi: 10.1021/jf8005273. Epub 2008 Jun 14"