| Title: | "exo-Brevicomin biosynthesis in the fat body of the mountain pine beetle, Dendroctonus ponderosae" |
| Author(s): | Song M; Gorzalski A; Nguyen TT; Liu X; Jeffrey C; Blomquist GJ; Tittiger C; |
| Address: | "Department of Biochemistry and Molecular Biology, University of Nevada, Reno, Mail Stop 330, Reno, NV, 89557, USA" |
| DOI: | 10.1007/s10886-014-0381-9 |
| ISSN/ISBN: | 1573-1561 (Electronic) 0098-0331 (Linking) |
| Abstract: | "exo-Brevicomin (exo-7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]octane) is an important semiochemical for a number of beetle species, including the highly destructive mountain pine beetle, Dendroctonus ponderosae. It also has been found in other insects and even in the African elephant. Despite its significance, little is known about its biosynthesis. In order to fill this gap and to identify new molecular targets for potential pest management methods, we performed gas chromatography-mass spectrometry analyses of cell cultures and in vitro assays of various D. ponderosae tissues with exo-brevicomin intermediates, analogs, and inhibitors. We confirmed that exo-brevicomin was synthesized by 'unfed' males after emerging from the brood tree. Furthermore, in contrast to the paradigm established for biosynthesis of monoterpenoid pheromone components in bark beetles, exo-brevicomin was produced in the fat body, and not in the anterior midgut. The first committed step involves decarboxylation or decarbonylation of omega-3-decenoic acid, which is derived from a longer-chain precursor via beta-oxidation, to (Z)-6-nonen-2-ol. This secondary alcohol is converted to the known precursor, (Z)-6-nonen-2-one, and further epoxidized by a cytochrome P450 to 6,7-epoxynonan-2-one. The keto-epoxide is stable at physiological pH, suggesting that its final cyclization to form exo-brevicomin is enzyme-catalyzed. exo-Brevicomin production is unusual in that tissue not derived from ectoderm apparently is involved" |
| Keywords: | "Animals Bridged Bicyclo Compounds, Heterocyclic/analysis/*metabolism Coleoptera/chemistry/*metabolism Fat Body/chemistry/*metabolism Female Ketones/analysis/metabolism Male Pheromones/analysis/*metabolism;" |
| Notes: | "MedlineSong, Minmin Gorzalski, Andrew Nguyen, Trang T Liu, Xibei Jeffrey, Christopher Blomquist, Gary J Tittiger, Claus eng 8 P20GM103440-11/GM/NIGMS NIH HHS/ Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, Non-P.H.S. 2014/02/18 J Chem Ecol. 2014 Feb; 40(2):181-9. doi: 10.1007/s10886-014-0381-9. Epub 2014 Feb 16" |
