Development of a novel photosynthesis inhibitor based on cyanobacterin

点击翻译按钮获取中文摘要

Cyanobacterin (1a) is an allelopathic substance isolated from the freshwater cyanobacterium Scytonema hofmanni, UTEX2349 which inhibits the growth of other cyanobacteria and green algae by inhibiting photosynthetic electron transport in the oxygen-evolving system of photosynthesis (photosystem II). A total synthesis of (+)-1a was achieved using (5R)-5-(1-menthyloxy)-2(5H)-furanone as a chiral synthon. Neither synthesized (+)-1a nor its derivatives showed distinct herbicidal activity on Oryza sativa. On the other hand, (+)-cyanobacterin and its epimer at 3-C, epicyanobacterin, showed potent argicidal activity against red tide pytoplanktons, Heterocapsa circularisquama and Chattonella marina, while they were inactive against Enteromorpha compressa. These results demonstrate cyanobacterin and epicyanobacterin to be potential lead compounds for development of a novel species-specific anti-red tide agent.