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. Epub 2019 Feb 22.

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.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Anti-Infective Agents / pharmacology
  • Bivalvia / chemistry*
  • Pseudomonas aeruginosa / chemistry*
  • Pyrroles / chemistry
  • Pyrroles / isolation & purification*
  • Pyrroles / pharmacology

Substances

  • Anti-Infective Agents
  • Pyrroles