ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
1/1
0/0

Structure, Synthesis of Hierridin C and Discovery of Prevalent Alkylresorcinol Biosynthesis in Picocyanobacteria

preprint
submitted on 14.09.2018 and posted on 18.09.2018 by Margarida Costa, Ivo E. Sampaio-Dias, Raquel Castelo-Branco, Hugo Scharfenstein, Roberta Rezende de Castro, Artur Silva, Maria Paula Cruz Schneider, Maria João Araújo, Rosário Martins, Valentina F. Domingues, Fatima Nogueira, Vera Camões, Vitor M. Vasconcelos, Pedro Leao
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.

Funding

NORTE-01-0145-FEDER-000035 (ERDF/NORTE2020); POCI-01-0145-FEDER-007265 (PT2020/ERDF), UID/Multi/04423/2013, GHTM - UID/Multi/04413/2013, PTDC/MAR-BIO/2818/2013, UID/QUI/50006/2013

History

Email Address of Submitting Author

pleao@ciimar.up.pt

Institution

CIIMAR - University of Porto

Country

Portugal

ORCID For Submitting Author

0000-0001-5064-9164

Declaration of Conflict of Interest

The authors declare the following conflicts of interest: The antiplasmodial activity of hierridin C, one of the compounds reported herein, has formed the basis for of a patent application (WO2016207869), in which some of the authors are co-inventors.

Exports

Logo branding

Exports