Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, Canada.
J Chem Ecol. 1992 Aug;18(8):1389-404. doi: 10.1007/BF00994364.
The ability of (E)- and (Z)-6-nonen-2-one to serve as precursors of the common scolytid pheromonesEndo- andexo-brevicomin was examined in vivo. When mountain pine beetles (MPB),Dendroctonus ponderosae Hopkins, or western balsam bark beetles (WBBB),Dryocoetes confusus Swaine, were exposed to 6,7-D2-6-nonen-2-one, theEndo-brevicomin produced was enriched with two deuterium atoms per molecule (as determined by GC-MS), indicating that (E)-6-nonen-2-one served as a precursor of this pheromone. Similarly, when the beetles were exposed to 4,4-D2-6-nonen-2-one, theexo-brevicomin produced was enriched with two deuterium atoms per molecule. Evidence in support of biological relevance of the latter observation include: (1) (Z)-6-nonen-2-one was found in the volatiles of male MPBs and WBBBs, indicating that this is a natural metabolite; (2) theexo-brevicomin produced by MPB was shown to be of natural (+) chirality by complexation chromatography; and (3) female WBBBs and MPBs (which are not known to produceexo-brevicomin) produced significantly lessexo-brevicomin when exposed to the precursor than did the males.
（E）-和（Z）-6-壬烯-2-酮作为常见的小蠹虫信息素endo-和exo-法尼醇的前体在体内进行了研究。当山松甲虫（MPB）或西部扁柏树皮甲虫（WBBB）暴露于[6,7-D2]（E）-6-壬烯-2-酮时，产生的endo-法尼醇每个分子中都富集了两个氘原子（通过 GC-MS 确定），表明（E）-6-壬烯-2-酮是该信息素的前体。同样，当甲虫暴露于[4,4-D2]（Z）-6-壬烯-2-酮时，产生的exo-法尼醇每个分子中都富集了两个氘原子。支持后一种观察结果具有生物学相关性的证据包括：（1）在雄性 MPB 和 WBBB 的挥发物中发现了（Z）-6-壬烯-2-酮，表明这是一种天然代谢物；（2）通过络合色谱法证明 MPB 产生的 exo-法尼醇具有天然的（+）手性；（3）暴露于前体的雌性 WBBB 和 MPB（已知不产生 exo-法尼醇）产生的 exo-法尼醇明显少于雄性。
