Structure of Hierridin C, Synthesis of Hierridins B and C, and Evidence for Prevalent Alkylresorcinol Biosynthesis in Picocyanobacteria

• Type: Article in International Scientific Journal
• Date: 2019-02-04

Authors

Maria J Araujo (Author) FCUP; Ivo E Sampaio-Dias (Author) FCUP

Journal

Title: Journal of Natural Products

Vol. 82

Pages: 393-402

ISSN: 0163-3864

Publisher: American Chemical Society

Indexing

ISI Web of Knowledge - 13 Citations

Scopus - 15 Citations

Other information

Authenticus ID: P-00Q-7CQ

DOI: 10.1021/acs.jnatprod.8b01038

Abstract (EN): 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.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 10