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Insect Biochem Mol Biol

Title:		Thiafatty acids as tracers to investigate biosynthetic pathways of lepidopteran sex pheromones
Author(s):		Pinilla A; Mas E; Camps F; Fabrias G;
Address:		"Departamento de Quimica Organica Biologica, Instituto de Investigaciones Quimicas y Ambientales de Barcelona (IIQAB), CSIC, Jordi Girona 18, 08034, Barcelona, Spain"
Journal Title:		Insect Biochem Mol Biol
Year:		2001
Volume:		31
Issue:		4-May
Page Number:		401 - 405
DOI:		10.1016/s0965-1748(00)00134-x
ISSN/ISBN:		0965-1748 (Print) 0965-1748 (Linking)
Abstract:		"In order to investigate the potential utility of thiafatty acids as tracers for biosynthetic studies of moth sex pheromones, a series of thiatetradecanoic acids, namely 8-, 9-, 10-, 11-, 12- and 13-thiatetradecanoic, were prepared and their metabolism was investigated in pheromone glands of Spodoptera littoralis. Analysis by gas chromatography coupled to mass spectrometry of extracts from pheromone glands treated with the above acids showed that only 8-thiatetradecanoic acid and 13-thiatetradecanoic acid were metabolized by desaturation and were incorporated into the sex pheromone biosynthetic pathway. 13-Thiatetradecanoic acid was converted into (E)- and (Z)-13-thiatetradec-11-enoic acids, (Z,E)-13-thiatetradeca-9,11-dienoic acid, 11-thiadodecanoic acid, (E)- and (Z)-11-thiadodec-9-enoic acids and 15-thiahexadecanoic acid. 8-Thiatetradecanoic acid gave rise to two monoenoic thiafatty acids and two dienoic thiafatty acids, which were assigned to (Z)- and (E)-8-thiatetradec-11-enoic acids, (Z,E)-8-thiatetradeca-9,11-dienoic acid and (E,E)-8-thiatetradeca-10,12-dienoic acid. The other thiafatty acids tested, 9-, 10-, 11- and 12-thiatetradecanoic acids, were not metabolized by desaturation, although the corresponding products of beta-oxidation and chain elongation were detected. The occurrence of sulfoxides was not detected in this case, in disagreement with results on the metabolism of some thiaacids previously reported by other authors in yeast, Saccharomyces cerevisiae"
Keywords:		"Animals Exocrine Glands/metabolism Fatty Acids, Unsaturated/metabolism Gas Chromatography-Mass Spectrometry Myristic Acids/chemistry/*metabolism Sex Attractants/*biosynthesis Spodoptera/*metabolism Sulfur Compounds/chemistry/*metabolism;"
Notes:		"MedlinePinilla, A Mas, E Camps, F Fabrias, G eng Research Support, Non-U.S. Gov't England 2001/02/27 Insect Biochem Mol Biol. 2001 Mar 15; 31(4-5):401-5. doi: 10.1016/s0965-1748(00)00134-x"