title: Steps in the biosynthesis of fuscumol in the longhorn beetles Tetropium fuscum (F.) and Tetropium cinnamopterum Kirby.
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.
authors.affiliation: Natural Resources Canada, Canadian Forest Service - Atlantic Forestry Centre, PO Box 4000, Fredericton, NB, E3B 5P7, Canada.
authors.forename: Peter D
authors.initials: PD
authors.lastname: Mayo
authors.forename: Peter J
authors.initials: PJ
authors.lastname: Silk
authors.forename: Michel
authors.initials: M
authors.lastname: Cusson
authors.forename: Catherine
authors.initials: C
authors.lastname: Béliveau
mesh_terms: D000818:Animals; D003001:Cloning, Molecular; D001517:Coleoptera / Q000201:enzymology / Q000235:genetics / Q000378:metabolism*; D005260:Female; D015971:Gene Expression Regulation, Enzymologic; D051228:Geranyltranstransferase / Q000235:genetics / Q000378:metabolism; D008297:Male; D009928:Organ Specificity; D010675:Pheromones / Q000096:biosynthesis*; D012333:RNA, Messenger / Q000235:genetics / Q000378:metabolism; D013729:Terpenes / Q000378:metabolism
chemical_list: D010675:Pheromones; D012333:RNA, Messenger; D013729:Terpenes; C000588602:fuscumol; D051228:Geranyltranstransferase