Premium
An Unsaturated Quinolone N ‐Oxide of Pseudomonas aeruginosa Modulates Growth and Virulence of Staphylococcus aureus
Author(s) -
Szamosvári Dávid,
Böttcher Thomas
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201702944
Subject(s) - pseudomonas aeruginosa , virulence , staphylococcus aureus , quinolone , microbiology and biotechnology , chemistry , opportunistic pathogen , pathogen , bacteria , nitrate reductase , biology , antibiotics , biochemistry , enzyme , gene , genetics
The pathogen Pseudomonas aeruginosa produces over 50 different quinolones, 16 of which belong to the class of 2‐alkyl‐4‐quinolone N ‐oxides (AQNOs) with various chain lengths and degrees of saturation. We present the first synthesis of a previously proposed unsaturated compound that is confirmed to be present in culture extracts of P . aeruginosa , and its structure is shown to be trans‐Δ 1 ‐2‐(non‐1‐enyl)‐4‐quinolone N ‐oxide. This compound is the most active agent against S. aureus , including MRSA strains, by more than one order of magnitude whereas its cis isomer is inactive. At lower concentrations, the compound induces small‐colony variants of S . aureus , reduces the virulence by inhibiting hemolysis, and inhibits nitrate reductase activity under anaerobic conditions. These studies suggest that this unsaturated AQNO is one of the major agents that are used by P . aeruginosa to modulate competing bacterial species.