Revisiting quorum sensing: Discovery of additional chemical and biological functions for 3-oxo-N-acylhomoserine lactones

Gunnar F. Kaufmann, Rafaella Sartorio, Sang Hyeup Lee, Claude J. Rogers, Michael M. Meijler, Jason A. Moss, Bruce Clapham, Andrew P. Brogan, Tobin J. Dickerson, Kim D. Janda

Research output: Contribution to journalArticlepeer-review

258 Scopus citations

Abstract

Bacteria use small diffusible molecules to exchange information in a process called quorum sensing. An important class of autoinducers used by Gram-negative bacteria is the family of N-acylhomoserine lactones. Here, we report the discovery of a previously undescribed nonenzymatically formed product from N-(3-oxododecanoyl)-L-homoserine lactone; both the N-acylhomoserine and its novel tetramic acid degradation product 3-(1-hydroxydecylidene)-5-(2- hydroxyethyl)pyrrolidine-2,4-dione, are potent antibacterial agents. Bactericidal activity was observed against all tested Gram-positive bacterial strains, whereas no toxicity was seen against Gram-negative bacteria. We propose that Pseudomonas aeruginosa utilizes this tetramic acid as an interference strategy to preclude encroachment by competing bacteria. Additionally, we have discovered that this tetramic acid binds iron with comparable affinity to known bacterial siderophores, possibly providing an unrecognized mechanism for iron solubilization. These findings merit new attention such that other previously identified autoinducers be reevaluated for additional biological functions.

Original languageEnglish
Pages (from-to)309-314
Number of pages6
JournalProceedings of the National Academy of Sciences of the United States of America
Volume102
Issue number2
DOIs
StatePublished - 11 Jan 2005
Externally publishedYes

Keywords

  • Bactericidal agents
  • Evolution
  • Tetramic acid

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