« Previous Abstract[Progress in the application of preparative gas chromatography in separating volatile compounds]    Next Abstract"The ubc2 gene of Ustilago maydis encodes a putative novel adaptor protein required for filamentous growth, pheromone response and virulence" »

J Chem Ecol

Title:		Steps in the biosynthesis of fuscumol in the longhorn beetles Tetropium fuscum (F.) and Tetropium cinnamopterum Kirby
Author(s):		Mayo PD; Silk PJ; Cusson M; Beliveau C;
Address:		"Natural Resources Canada, Canadian Forest Service - Atlantic Forestry Centre, PO Box 4000, Fredericton, NB, E3B 5P7, Canada"
Journal Title:		J Chem Ecol
Year:		2013
Volume:		20130305
Issue:		3
Page Number:		377 - 389
DOI:		10.1007/s10886-013-0260-9
ISSN/ISBN:		1573-1561 (Electronic) 0098-0331 (Linking)
Abstract:		"Fuscumol [(2S,5E)-6,10-dimethyl-5,9-undecadien-2-ol] was recently identified as the male-produced aggregation pheromone of the brown spruce longhorn beetle, Tetropium fuscum (F.), and the eastern larch borer, Tetropium cinnamopterum Kirby. Several other species use this homoterpenoid alcohol motif, its ketone, or its acetate as part of their pheromone system. Investigation of the biosynthesis of this compound in these two Tetropium species demonstrated that geranylacetone [(5E)-6,10-dimethyl-5,9-undecadien-2-one] and farnesol [(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol] are both intermediates in this process. This was accomplished by applying deuterium-labeled geranylacetone and deuterium-labeled farnesol in separate experiments to the abdominal sterna of live T. fuscum and T. cinnamopterum and analyzing the deuterium labeling in the fuscumol and geranylacetone emitted by the insects with solid-phase microextraction (SPME) and GC/MS analysis. Deuterium labeling studies also showed that nerolidol[(3S,6E)-3-hydroxy-3,7,11-trimethyl-1,6,10-dodecatriene] and 2,3-epoxyfarnesol are not intermediates in fuscumol or geranylacetone synthesis in T. fuscum or T. cinnamopterum. Tissue-specific expression of T. fuscum farnesyl diphosphate synthase (TfFPPS), an enzyme expected to provide a key fuscumol precursor, was measured. TfFPPS transcripts were relatively abundant in male midguts, but were also present at significant levels in other tissues"
Keywords:		"Animals Cloning, Molecular Coleoptera/enzymology/genetics/*metabolism Female Gene Expression Regulation, Enzymologic Geranyltranstransferase/genetics/metabolism Male Organ Specificity Pheromones/*biosynthesis RNA, Messenger/genetics/metabolism Terpenes/me;"
Notes:		"MedlineMayo, Peter D Silk, Peter J Cusson, Michel Beliveau, Catherine eng Research Support, Non-U.S. Gov't 2013/03/08 J Chem Ecol. 2013 Mar; 39(3):377-89. doi: 10.1007/s10886-013-0260-9. Epub 2013 Mar 5"