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

Costa, Margarida Sofia, Sampaio-Dias, Ivo E., Castelo-Branco, Raquel, Scharfenstein, Hugo, Rezende de Castro, Roberta C., Artur M. S. Silva, Schneider, Maria Paula Cruz, Araújo, Maria João, R. Martins, Valentina F. Domingues, F Nogueira, Camões, Vera, Vitor Vasconcelos, Leão, Pedro Nuno

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2 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. © 2019 American Chemical Society and American Society of Pharmacognosy.
Original languageEnglish
Pages (from-to)393-402
Number of pages9
JournalJournal Of Natural Products
VolumeVol. 82
Issue numbern.º 2
DOIs
Publication statusPublished - 22 Feb 2019

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    Margarida Sofia, C., Ivo E., S-D., Raquel, C-B., Hugo, S., Roberta C., R. D. C., Silva, A. M. S., ... Pedro Nuno, L. (2019). Structure of hierridin c, synthesis of hierridins b and c, and evidence for prevalent alkylresorcinol biosynthesis in picocyanobacteria. Journal Of Natural Products, Vol. 82(n.º 2), 393-402. https://doi.org/10.1021/acs.jnatprod.8b01038