TY - JOUR
T1 - Structure of hierridin c, synthesis of hierridins b and c, and evidence for prevalent alkylresorcinol biosynthesis in picocyanobacteria
AU - Costa, Margarida
AU - Sampaio-Dias, Ivo E.
AU - Castelo-Branco, Raquel
AU - Scharfenstein, Hugo
AU - Rezende De Castro, Roberta
AU - Silva, Artur
AU - Schneider, Maria Paula C.
AU - Araújo, Maria Joao
AU - Martins, Rosário
AU - Domingues, Valentina F.
AU - Nogueira, Fátima
AU - Camoes, Vera
AU - Vasconcelos, Vitor M.
AU - Leao, Pedro N.
PY - 2019/2/22
Y1 - 2019/2/22
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85061266922&partnerID=8YFLogxK
U2 - 10.1021/acs.jnatprod.8b01038
DO - 10.1021/acs.jnatprod.8b01038
M3 - Article
C2 - 30715888
AN - SCOPUS:85061266922
SN - 0163-3864
VL - 82
SP - 393
EP - 402
JO - Journal Of Natural Products
JF - Journal Of Natural Products
IS - 2
ER -