Structure of Hierridin C, Synthesis of Hierridins B and C, and Evidence for Prevalent Alkylresorcinol Biosynthesis in Picocyanobacteria

• Autor(a) principal: Costa, Margarida
• Data de Publicação: 2019
• Outros Autores: Sampaio-Dias, Ivo E., Castelo-Branco, Raquel, Scharfenstein, Hugo, Rezende de Castro, Roberta, Silva, Artur, Schneider, Maria Paula C., Araújo, Maria João, Martins, Rosário, Domingues, Valentina F., Nogueira, Fátima, Camões, Vera, Vasconcelos, Vitor M., Leão, Pedro N.
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
• Texto Completo: http://hdl.handle.net/10400.22/16396
• topic: Anisoles; Cyanobacteria; Genome; Multigene Family; Resorcinols; Bacteria; Metabolism; Aromatic compounds; Cluster chemistry

Small, 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.