Structure, synthesis of hierridin C and discovery of prevalent alkylresorcinol biosynthesis in picocyanobacteria

Margarida Costa, I.E. Sampaio-Dias, R. Castelo-Branco, H. Scharfenstein, R. Rezende de Castro, Artur M. S. Silva, M.P.C. Schneider, Maria João Araújo, Rosário Martins, V.F. Domingues, F. Nogueira, V. Camões, V.M. Vasconcelosa, P.N. Leão

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Abstract

Small, single-celled planktonic cyanobacteria are ubiquitous in the world’s oceans yet tend not to to be perceived as biosynthetically-prolific organisms. Here we report the isolation and structure elucidation of hierridin C, an antiplasmodial halogenated alkylresorcinol produced in very low amounts by the picocyanobacterium Cyanobiumsp. LEGE 06113. We describe a simple, straightforward synthetic route to the scarcely-produced hierridins that relies on a key, highly 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, Cyanobiumand Synechococcus.
Original languageEnglish
PublisherChemRxiv
Number of pages8
DOIs
Publication statusPublished - 2018

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