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Electrospray/mass spectrometric identification and analysis of 4-hydroxy-2-alkylquinolines (HAQs) produced by Pseudomonas aeruginosa

Lépine, François; Milot, Sylvain; Déziel, Éric; He, Jianxin; Rahme, Laurence G. (2004). Electrospray/mass spectrometric identification and analysis of 4-hydroxy-2-alkylquinolines (HAQs) produced by Pseudomonas aeruginosa Journal of the American Society for Mass Spectrometry , vol. 15 , nº 6. p. 862-869. DOI: 10.1016/j.jasms.2004.02.012.

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Résumé

The opportunistic pathogen Pseudomonas aeruginosa produces a large array of 4-hydroxy-2alkylquinolines (HAQs). These compounds were analyzed by LC/MS, using positive electrospray ionization, in the culture supernatant of strain PA14. Fifty-six HAQs and related compounds were detected and their [M + H](+) ions were further analyzed by collision induced dissociation (CID). These HAQs were grouped into five different series based on the presence of an hydrogen or hydroxyl group at the 3 position, an N-oxide group in place of the quinoline nitrogen, and an unsaturation on their alkyl side chain. Two new analogs of 3,4-dihydroxy-2 heptylquinoline, the Pseudomonas quinolone signal (PQS), were found with an alkyl chain longer by one and two methylene groups. Moreover, two additional series of compounds were identified in which a saturated or unsaturated alkyl side chain is located at the 3 position along with an hydroxyl group at the 3 position and a ketone at the 2 position. No HAQ N-oxides, nor any compounds from the latter two series, were detected in a pqsL mutant derivative of PA14, indicating that this gene is involved in the biosynthesis of these compounds. This work demonstrates the large repertoire of HAQ and HAQ-related compounds produced by P. aeruginosa, and provides insight into N-oxides biosynthesis and confirm the hypothesis that N-oxides are the precursors of compounds from Series 6 and 7

Type de document:
Mots-clés libres: bacterial strain, bacterium culture, biosynthesis, collisionally activated dissociation, electrospray mass spectrometry, liquid chromatography, Pseudomonas aeruginosa, supernatant
Centre: Centre INRS-Institut Armand Frappier
Date de dépôt: 02 mai 2014 14:04
Dernière modification: 02 mai 2014 14:04
URI: http://espace.inrs.ca/id/eprint/2247

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