Identification of four new agr quorum sensing-interfering cyclodepsipeptides from a marine Photobacterium

Mar Drugs. 2013 Dec 12;11(12):5051-62. doi: 10.3390/md11125051.

Abstract

During our search for new natural products from the marine environment, we discovered a wide range of cyclic peptides from a marine Photobacterium, closely related to P. halotolerans. The chemical fingerprint of the bacterium showed primarily non-ribosomal peptide synthetase (NRPS)-like compounds, including the known pyrrothine antibiotic holomycin and a wide range of peptides, from diketopiperazines to cyclodepsipeptides of 500-900 Da. Purification of components from the pellet fraction led to the isolation and structure elucidation of four new cyclodepsipeptides, ngercheumicin F, G, H, and I. The ngercheumicins interfered with expression of virulence genes known to be controlled by the agr quorum sensing system of Staphylococcus aureus, although to a lesser extent than the previously described solonamides from the same strain of Photobacterium.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / metabolism
  • Bacterial Proteins / genetics
  • Bacterial Proteins / isolation & purification*
  • Bacterial Proteins / metabolism
  • Depsipeptides / genetics
  • Depsipeptides / isolation & purification*
  • Depsipeptides / metabolism
  • Lactams / metabolism
  • Peptide Synthases / genetics
  • Peptide Synthases / metabolism
  • Photobacterium / chemistry*
  • Photobacterium / genetics
  • Photobacterium / metabolism
  • Quorum Sensing / drug effects*
  • Quorum Sensing / genetics
  • Staphylococcus aureus / drug effects
  • Staphylococcus aureus / genetics
  • Staphylococcus aureus / metabolism
  • Virulence / genetics

Substances

  • Anti-Bacterial Agents
  • Bacterial Proteins
  • Depsipeptides
  • Lactams
  • holomycin
  • Peptide Synthases
  • non-ribosomal peptide synthase