Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
5 years ago

An Unsaturated Quinolone N-Oxide of Pseudomonas aeruginosa Modulates Growth and Virulence of Staphylococcus aureus

An Unsaturated Quinolone N-Oxide of Pseudomonas aeruginosa Modulates Growth and Virulence of Staphylococcus aureus
Thomas Böttcher, Dávid Szamosvári
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-Δ1-2-(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. Pseudomonas’ secret weapon: trans-Δ1-2-Nonenyl-4-quinolone N-oxide, the most active quinolone N-oxide produced by Pseudomonas aeruginosa against Staphylococcus aureus, was synthesized. The efficacy of this compound is also demonstrated by its ability to inhibit the hemolytic and nitrate reductase activity of S. aureus at low concentrations. These results shed new light onto how P. aeruginosa chemically modulates the growth and behavior of its competitors.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201702944

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