« Previous Abstract"Novel components of the sex pheromones produced by emerald moths: identification, synthesis, and field evaluation"    Next AbstractFemale sex pheromone of Cystidia couaggaria couaggaria (Lepidoptera: Geometridae): identification and field attraction »

J Chem Ecol

Title:		"Characterization of epoxytrienes derived from (3Z,6Z,9Z)-1,3,6,9-tetraenes, sex pheromone components of arctiid moths and related compounds"
Author(s):		Yamakawa R; Takubo Y; Shibasaki H; Murakami Y; Yamamoto M; Ando T;
Address:		"Graduate School of Bio-Applications and Systems Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan"
Journal Title:		J Chem Ecol
Year:		2012
Volume:		20120727
Issue:		8
Page Number:		1042 - 1049
DOI:		10.1007/s10886-012-0165-z
ISSN/ISBN:		1573-1561 (Electronic) 0098-0331 (Linking)
Abstract:		"Cis-9,10-epoxy-(3Z,6Z)-1,3,6-henicosatriene has been identified from a pheromone gland of arctiid species, such as Hyphantria cunea. Since the diversity of lepidopteran species suggests that structurally related compounds of the 9,10-epoxide are also utilized as a sex pheromone components, epoxytrienes derived from (3Z,6Z,9Z)-1,3,6,9-tetraenes with a C(19)-C(21) chain were systematically synthesized and characterized. While 1,2-epoxy-3,6,9-triene was not obtained, peracid oxidation of each tetraene produced a mixture of three cis-epoxides (3,4-epoxy-1,6,9-triene, 6,7-epoxy-1,3,9-triene, and 9,10-epoxy-1,3,6-triene), which were separable by LC as well as GC. Detailed inspection of the mass spectra of the C(19)-C(21) epoxides indicated the following diagnostic ions for determining the chemical structures: m/z 79, M-70, and M-41 for the 3,4-epoxytrienes; m/z 79, 95, 109, and 149 for the 6,7-epoxytrienes; and m/z 79, 106, 120, M-121, and M-107 for the 9,10-epoxytrienes. Resolution of two enantiomers of each C(21) epoxytriene was accomplished by HPLC equipped with a chiral column, and analysis of the pheromone extracted from virgin females of H. cunea revealed the 9S,10R configuration of the natural epoxytriene as the same configuration of C(21) 9,10-epoxydiene, a main pheromone component of this species. GC-EAD analysis of the optically pure epoxides showed that the antennae of male H. cunea were stimulated more strongly (>100 times) by the (9S,10R)-isomers than the antipodes"
Keywords:		"Animals Behavior, Animal/drug effects Chromatography, High Pressure Liquid Epoxy Compounds/*chemistry Female Gas Chromatography-Mass Spectrometry Magnetic Resonance Spectroscopy Male Moths/drug effects/*metabolism Polyenes/*chemistry/pharmacology Sex Attr;"
Notes:		"MedlineYamakawa, Rei Takubo, Yoshiko Shibasaki, Hiroshi Murakami, Yoko Yamamoto, Masanobu Ando, Tetsu eng 2012/07/28 J Chem Ecol. 2012 Aug; 38(8):1042-9. doi: 10.1007/s10886-012-0165-z. Epub 2012 Jul 27"