Resorculins: hybrid polyketide macrolides from Streptomyces sp. MST-91080

Heather J. Lacey, Rachel Chen, Daniel Vuong, Ernest Lacey, Peter J. Rutledge, Yit-Heng Chooi, Andrew M. Piggott and Thomas J. Booth

Organic and Biomolecular Chemistry 21, 2531-2538.

Publication Date: Feb 27, 2023


Fourteen-membered macrolides are a class of compounds with significant clinical value as antibacterial agents. As part of our ongoing investigation into the metabolites of Streptomyces sp. MST-91080, we report the discovery of resorculins A and B, unprecedented 3,5-dihydroxybenzoic acid (α-resorcylic acid)-containing 14-membered macrolides. We sequenced the genome of MST-91080 and identified the putative resorculin biosynthetic gene cluster (rsn BGC). The rsn BGC is hybrid of type I and type III polyketide synthases. Bioinformatic analysis revealed that the resorculins are relatives of known hybrid polyketides: kendomycin and venemycin. Resorculin A exhibited antibacterial activity against Bacillus subtilis (MIC 19.8 μg mL−1), while resorculin B showed cytotoxic activity against the NS-1 mouse myeloma cell line (IC50 3.6 μg mL−1).

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