Costa, MargaridaSampaio-Dias, Ivo E.Castelo-Branco, RaquelScharfenstein, HugoRezende de Castro, RobertaSilva, ArturSchneider, Maria Paula C.Araújo, Maria JoãoMartins, RosárioDomingues, Valentina F.Nogueira, FátimaCamões, VeraVasconcelos, Vitor M.Leão, Pedro N.2020-10-302020-10-302019-020163-3864http://hdl.handle.net/10400.22/16396Small, single-celled planktonic cyanobacteria are ubiquitous in the world's oceans yet tend not to be perceived as secondary metabolite-rich organisms. Here we report the isolation and structure elucidation of hierridin C, a minor metabolite obtained from the cultured picocyanobacterium Cyanobium sp. LEGE 06113. We describe a simple, straightforward synthetic route to the scarcely produced hierridins that relies on a key regioselective halogenation step. In addition, we show that these compounds originate from a type III PKS pathway and that similar biosynthetic gene clusters are found in a variety of bacterial genomes, most notably those of the globally distributed picocyanobacteria genera Prochlorococcus, Cyanobium and Synechococcus.engAnisolesCyanobacteriaGenomeMultigene FamilyResorcinolsBacteriaMetabolismAromatic compoundsCluster chemistryjournal article10.1021/acs.jnatprod.8b01038