Structure of hierridin c, synthesis of hierridins b and c, and evidence for prevalent alkylresorcinol biosynthesis in picocyanobacteria

Margarida Costa, Ivo E. Sampaio-Dias, Raquel Castelo-Branco, Hugo Scharfenstein, Roberta Rezende De Castro, Artur Silva, Maria Paula C. Schneider, Maria Joao Araújo, Rosário Martins, Valentina F. Domingues, Fátima Nogueira, Vera Camoes, Vitor M. Vasconcelos, Pedro N. Leao

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)393-402
Number of pages10
JournalJournal Of Natural Products
Volume82
Issue number2
DOIs
Publication statusPublished - 22 Feb 2019

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