title: Transformation of presumptive precursors to frontalin and exo-brevicomin by bark beetles and west Indian sugarcane weevil (Coleoptera).
abstract: (Z)-6-Nonen-2-one (1) has recently been shown to be the biosynthetic precursor for the aggregation pheromone exo-brevicomin (2) in mountain pine beetle (MPB) males, Dendroctonus ponderosae (Hopkins). We tested the hypotheses that (1) 6-methyl-6-hepten-2-one (3) is the biosynthetic precursor for the aggregation pheromone frontalin (4) in the spruce beetle (SB), Dendroctonus rufipennis (Kirby), and (2) that frontalin and exo-brevicomin are produced from 3 and 1, respectively, only by beetles that utilize them as aggregation pheromones. Exposure of scolytids MPB, SB, pine engraver (PE), Ips pini (Say) and Ips tridens (Mannerheim) and West Indian sugar cane weevil (WISW), Metamasius hemipterus sericeus (Olivier) to deuterio- or protio-3 invariably resulted in the production of deuterio- or protio-4. Similarly, exposure of SB, WISW and I. tridens to 1 resulted in the production of 2. We were unable to demonstrate the presence of 3 in SB volatiles, nor were we able to demonstrate the conversion of 6-methyl-5-hepten-2-one to 3 by SB. Production of enantiomerically enriched frontalin and exo-brevicomin by all the beetles exposed to respective precursors reveals widespread occurrence of nonspecific polysubstrate monooxidases in the Coleoptera.
authors: Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, Canada.
authors: A L
authors: AL
authors: Perez
authors: R
authors: R
authors: Gries
authors: G
authors: G
authors: Gries
authors: A C
authors: AC
authors: Oehlschlager
mesh_terms: D000080:Acetals / Q000378:metabolism; D000818:Animals; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000378:metabolism*; D001517:Coleoptera / Q000378:metabolism*; D005260:Female; D008401:Gas Chromatography-Mass Spectrometry; D007659:Ketones / Q000378:metabolism; D008297:Male; D010675:Pheromones / Q000378:metabolism*; D013237:Stereoisomerism
chemical_list: C101379:6-nonen-2-one; D000080:Acetals; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007659:Ketones; D010675:Pheromones; C101378:6-methyl-6-hepten-2-one; C012327:frontalin; C012219:brevicomin