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

• Autor(es): Costa, Margarida ; Sampaio-Dias, Ivo E. ; Castelo-Branco, Raquel ; Scharfenstein, Hugo ; Rezende de Castro, Roberta ; Silva, Artur ; Schneider, Maria Paula C. ; Araújo, Maria João ; Martins, Rosario ; Domingues, Valentina F. ; Nogueira, Fátima ; Camões, Vera ; Vasconcelos, Vitor M. ; Leão, Pedro N.
• Data: 2019
• Identificador Persistente: http://hdl.handle.net/10400.22/12978
• Origem: Repositório Científico do Instituto Politécnico do Porto
• Assunto(s): Picocyanobacterium; bacterial genomes
• Tipo de Documento: Artigo científico
• Idioma: Inglês
• Contribuidor(es): REPOSITÓRIO P.PORTO

Descrição

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.