Mori Kenji
Photosensitive Materials Research Center, Toyo Gosei Co., Ltd, Wakahagi 4-2-1, Inba-mura, Inba-gun, Chiba 270-609, Japan.
Bioorg Med Chem. 2007 Dec 15;15(24):7505-23. doi: 10.1016/j.bmc.2007.08.040. Epub 2007 Aug 25.
Pheromones play important roles in chemical communication among organisms. Various chiral and non-racemic pheromones have been identified since the late 1960s. Their enantioselective syntheses could establish the absolute configuration of the naturally occurring pheromones and clarified the relationships between absolute configuration and bioactivity. For example, neither the (R)- nor (S)-enantiomer of sulcatol, the aggregation pheromone of an ambrosia beetle Gnathotrichus sulcatus, is behaviorally active, while their mixture is bioactive. In the case of olean, the olive fruit fly pheromone, its (R)-isomer is active for the males, and the (S)-isomer is active for the females. About 140 chiral pheromones are reviewed with regard to their stereochemistry-bioactivity relationships. Problems encountered in studying chirality of pheromones were examined and analyzed to think about possible future directions in pheromone science.
信息素在生物体之间的化学通讯中发挥着重要作用。自20世纪60年代末以来，已鉴定出各种手性和非外消旋信息素。它们的对映选择性合成可以确定天然存在的信息素的绝对构型，并阐明绝对构型与生物活性之间的关系。例如，粉蠹Gnathotrichus sulcatus的聚集信息素sulcatol的（R）-对映体和（S）-对映体在行为上均无活性，而它们的混合物具有生物活性。就橄榄实蝇信息素olean而言，其（R）-异构体对雄性有活性，（S）-异构体对雌性有活性。本文综述了约140种手性信息素的立体化学-生物活性关系。对研究信息素手性时遇到的问题进行了研究和分析，以思考信息素科学未来可能的发展方向。
