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dc.creatorCosta, M.
dc.creatorSampaio-Dias, I.E.
dc.creatorCastelo-Branco, R.
dc.creatorScharfenstein, H.
dc.creatorRezende De Castro, R.
dc.creatorSilva, A.
dc.creatorSchneider, M.P.C.
dc.creatorAraújo, M.J.
dc.creatorMartins, R.
dc.creatorDomingues, V.F.
dc.creatorNogueira, F.
dc.creatorCamoes, V.
dc.creatorVasconcelos, V.M.
dc.creatorLeao, P.N.
dc.identifier.issnISSN 1520-6025
dc.description.abstractSmall, 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.
dc.description.sponsorshipWe thank CEMUP for HRESIMS and NMR analyses. This research was supported by the Structured Program of R&D&I INNOVMAR - Innovation and Sustainability in the Manage- ment and Exploitation of Marine Resources (reference NORTE-01-0145-FEDER-000035, Research Line NOVEL- MAR), funded by the Northern Regional Operational Program (NORTE2020) through the European Regional Development Fund (ERDF). This work was also funded by Fundacão para a Ciência e Tecnologia (FCT), under the framework of projects UID/Multi/04423/2013, GHTM - UID/Multi/04413/2013 andPTDC/MAR-BIO/2818/2013,IFCTcontractIF/01358/ 2014 to P.N.L., and Ph.D. scholarship SFRH/BD/93632/2013 to IESD. In addition, this work was also partially supported by the Associate Laboratory for Green Chemistry - LAQV, which is financed by national funds from FCT/MCTES (UID/QUI/ 50006/2013) and cofinanced by the ERDF under the PT2020 Partnership Agreement (POCI-01-0145-FEDER-007265).
dc.publisherAmerican Chemical Society
dc.relation.ispartofJournal of Natural Products 2019, 82, 393−402
dc.titleStructure of hierridin c, synthesis of hierridins b and c, and evidence for prevalent alkylresorcinol biosynthesis in picocyanobacteria
dc.typeArtigo em Revista Científica Internacional
dc.contributor.uportoCentro Interdisciplinar de Investigação Marinha e Ambiental
Appears in Collections:CIIMAR - Artigo em Revista Científica Internacional

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