Faculty of Biology, University of Freiburg, 79104, Freiburg, Germany.
Chembiochem. 2020 Sep 1;21(17):2384-2407. doi: 10.1002/cbic.201900786. Epub 2020 May 8.
Tropone natural products are non-benzene aromatic compounds of significant ecological and pharmaceutical interest. Herein, we highlight current knowledge on bacterial tropones and their derivatives such as tropolones, tropodithietic acid, and roseobacticides. Their unusual biosynthesis depends on a universal CoA-bound precursor featuring a seven-membered carbon ring as backbone, which is generated by a side reaction of the phenylacetic acid catabolic pathway. Enzymes encoded by separate gene clusters then further modify this key intermediate by oxidation, CoA-release, or incorporation of sulfur among other reactions. Tropones play important roles in the terrestrial and marine environment where they act as antibiotics, algaecides, or quorum sensing signals, while their bacterial producers are often involved in symbiotic interactions with plants and marine invertebrates (e. g., algae, corals, sponges, or mollusks). Because of their potent bioactivities and of slowly developing bacterial resistance, tropones and their derivatives hold great promise for biomedical or biotechnological applications, for instance as antibiotics in (shell)fish aquaculture.
天然托品酮类化合物是非苯芳香族化合物,具有重要的生态和药物学意义。本文重点介绍了细菌托品酮及其衍生物(如托品酮、 tropodithietic 酸和 roseobacticides)的最新研究进展。其独特的生物合成途径依赖于一种普遍存在的 CoA 结合前体,该前体以 7 元碳环为骨架,是苯乙酸代谢途径的副反应生成的。然后,由不同基因簇编码的酶通过氧化、CoA 释放或掺入硫等反应进一步修饰这一关键中间体。托品酮在陆地和海洋环境中发挥着重要作用,它们可以作为抗生素、藻类抑制剂或群体感应信号,而其细菌产生者通常参与与植物和海洋无脊椎动物(如藻类、珊瑚、海绵或软体动物)的共生关系。由于其强大的生物活性和细菌耐药性的缓慢发展,托品酮及其衍生物在生物医药或生物技术应用方面具有巨大的潜力,例如作为(贝类)鱼类养殖中的抗生素。