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Author(s): Costa, M.
Sampaio-Dias, I.E.
Castelo-Branco, R.
Scharfenstein, H.
Rezende De Castro, R.
Silva, A.
Schneider, M.P.C.
Araújo, M.J.
Martins, R.
Domingues, V.F.
Nogueira, F.
Camoes, V.
Vasconcelos, V.M.
Leao, P.N.
Title: Structure of hierridin c, synthesis of hierridins b and c, and evidence for prevalent alkylresorcinol biosynthesis in picocyanobacteria
Publisher: American Chemical Society
Issue Date: 2019
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.
Source: Journal of Natural Products 2019, 82, 393−402
Document Type: Artigo em Revista Científica Internacional
Rights: restrictedAccess
Appears in Collections:CIIMAR - Artigo em Revista Científica Internacional

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