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Eur J Biochem

Title:		Biosynthesis of scarab beetle pheromones
Author(s):		Leal WS; Zarbin PH; Wojtasek H; Ferreira JT;
Address:		"Laboratory of Chemical Prospecting, National Institute of Sericultural and Entomological Science, Tsukuba, Japan. leal@nises.affrc.go.jp"
Journal Title:		Eur J Biochem
Year:		1999
Volume:		259
Issue:		1-Feb
Page Number:		175 - 180
DOI:		10.1046/j.1432-1327.1999.00018.x
ISSN/ISBN:		0014-2956 (Print) 0014-2956 (Linking)
Abstract:		"Chemical communication in scarab beetles (Coleoptera: Scarabaeidae) is achieved with a wide variety of pheromones, but one typical structure is the gamma-lactone having a long unsaturated hydrocarbon chain. Several species utilize (R, Z)-5-(-)-(oct-1-enyl)-oxacyclopentan-2-one (buibuilactone), (R, Z)-5-(-)-(dec-1-enyl)-oxacyclopentan-2-one and (S, Z)-5-(+)-(dec-1-enyl)-oxacyclopentan-2-one [(R)-japonilure and (S)-japonilure]. Using deuterated precursors, we have demonstrated that these compounds are biosynthesized from fatty acids. (9, 10-d4)-Palmitic acid, (9,10-d4)-stearic acid, (9,10-d2)-palmitoleic acid, (9,10-d2)-oleic acid, (9,10-d2)-8-hydroxypalmitoleic acid and (9,10-d2)-8-hydroxyoleic acid were readily incorporated by female Anomala cuprea into the pheromone molecules, while (Z)-(5, 6-d2)-5-dodecenoic acid and (Z)-(5,6-d2)-5-tetradecenoic acid were not. Therefore, the reaction pathway starts from saturated fatty acids, involves their desaturation, followed by 8-hydroxylation, chain shortening and cyclization. The products obtained from racemic (9,10-d2)-8-hydroxypalmitoleic acid and (9,10-d2)-8-hydroxyoleic acid were also racemic, implying that the steps following hydroxylation were not stereospecific. Perdeuterated palmitic acid was applied to disclose the mechanism of the unique hydroxylation reaction. Retention of all deuterium atoms implied that this reaction was a direct process mediated by a specific fatty acid hydroxylase, and preceding desaturation or epoxidation was not involved"
Keywords:		"4-Butyrolactone/*analogs & derivatives/biosynthesis Animals Coleoptera/*metabolism Fatty Acids/*metabolism Female Hydroxylation Lactones/metabolism Male Mass Spectrometry Models, Chemical Pheromones/*biosynthesis Sex Attractants/biosynthesis Stereoisomeri;"
Notes:		"MedlineLeal, W S Zarbin, P H Wojtasek, H Ferreira, J T eng Research Support, Non-U.S. Gov't England 1999/01/23 Eur J Biochem. 1999 Jan; 259(1-2):175-80. doi: 10.1046/j.1432-1327.1999.00018.x"