Mindapyrroles A-C, Pyoluteorin Analogues from a Shipworm-Associated Bacterium

  • J Nat Prod. 2019 Apr 26;82(4):1024-1028. doi: 10.1021/acs.jnatprod.8b00979.
Noel M Lacerna 2nd  1 ,  Bailey W Miller  2 ,  Albebson L Lim  1 ,  Jortan O Tun  1 ,  Jose Miguel D Robes  1 ,  Mark Jeremiah B Cleofas  1 ,  Zhenjian Lin  2 ,  Lilibeth A Salvador-Reyes  1 ,  Margo G Haygood  2 ,  Eric W Schmidt  2 ,  Gisela P Concepcion  1
Affiliations
  • 1. The Marine Science Institute , University of the Philippines , Diliman, Quezon City 1101 , Philippines.
  • 2. Department of Medicinal Chemistry , University of Utah , Salt Lake City , Utah 84112 , United States.
PMID: 30793902 DOI: 10.1021/acs.jnatprod.8b00979
Abstract

Three new pyoluteorin analogues, mindapyrroles A-C (1-3), were purified from Pseudomonas aeruginosa strain 1682U.R.0a.27, a gill-associated bacterium isolated from the tissue homogenate of the giant shipworm Kuphus polythalamius. Mindapyrroles B and C inhibit the growth of multiple pathogenic bacteria, with mindapyrrole B (2) showing the most potent antimicrobial activity and widest selectivity index over mammalian cells. Preliminary structure-activity relationship analysis showed that dimerization of the pyoluteorin moiety through a C-C linkage is detrimental to the antimicrobial activity, but addition of an aerugine unit in the methylene bridge is favorable for both the antimicrobial activity and selectivity index.