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

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.

Palavras-chave

QD Chemistry QR Microbiology General Biochemistry,Genetics and Molecular Biology General Pharmacology, Toxicology and Pharmaceutics Drug Discovery SDG 3 - Good Health and Well-being

URI

http://hdl.handle.net/10362/157780

Editora

ChemRxiv

DOI

10.26434/chemrxiv.7090526.v1

Coleções

Home collection (IHMT)

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