Rapid identification of 4-hydroxy-2-alkylquinolines produced by Pseudomonas aeruginosa using gas chromatography—electron-capture mass spectrometry

Taylor, Graham W.; Machan, Zoe A.; Mehmet, Senel; Cole, Peter; Wilson, Robert

doi:10.1016/0378-4347(94)00494-p

Cited by 28 publications

(27 citation statements)

References 13 publications

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“…The lack of significant inhibition of Xcc growth in vitro in iron-rich media encouraged us to conclude that the siderophore produced by KA19 could be one of the several metabolites responsible for black rot control. The identified metabolite, 4-hydroxy-2-alkyl-quinoline, comprises a class of heterocyclic molecules produced by P. aeruginosa that demonstrated antimicrobial properties against gram-positive bacteria including methicillin-resistant Staphylococcus aureus (Taylor et al 1995). These types of molecules are known as pseudans (Royt et al 2001).…”

Section: Discussionmentioning

confidence: 99%

“…These types of molecules are known as pseudans (Royt et al 2001). This group of molecules is based on the 4-hydroxy-2-alkyl-quinoline structure and is differentiated based upon the size and degree of saturation of the alkyl chain, as well as the presence or absence of the N-oxide (Taylor et al 1995). Pseudan IX, 4-hydroxy-2-nonyl-quinoline, and pseudan VII, 4-hydroxy-2-heptylquinoline, have been found to act as siderophores and reside in the cytoplasmic membrane of P. aeruginosa (Royt et al 2001).…”

Section: Discussionmentioning

confidence: 99%

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Evaluation of rhizospheric Pseudomonas and Bacillus as biocontrol tool for Xanthomonas campestris pv campestris

Mishra

Arora

2011

World J Microbiol Biotechnol

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Xanthomonas campestris pv campestris (Xcc), causing black rot, is one of the most yield-limiting and destructive pathogens of cruciferous crops. The intention of this study was to evaluate the potential of rhizobacteria in black rot management. Fifty-four isolates from rhizosphere soil of Brassica campestris were screened against Xcc. Two isolates namely, KA19 and SE, with inhibition radius >11 mm were selected. The combined use of them produced an average inhibition zone of 18.1 ± 1.4 mm radius (P < 0.05). 16S rRNA gene sequencing and phylogenetic analysis identified KA19 and SE as the nearest homologs (>99.4%) of Pseudomonas aeruginosa and Bacillus thuringiensis, respectively. In greenhouse study, both isolates were effective (P < 0.05) in reducing black rot lesions compared to untreated control involving either a foliar spray or the combined seed soak and soil drench. However, the combined strains (KA19 + SE) were significantly more effective (P < 0.05) when the mode of application was combined seed and soil drench. The lipid content of seeds increased significantly with the application of these strains, especially with SE alone and in combination. After 9 weeks, the Xcc population was significantly lower in soil treated with combined strains (P < 0.05). KA19 produced extracellular siderophores, influenced by various carbon sources and identified as 4-hydroxy-2-nonyl-quinoline by NMR. In Bacillus SE, two antibacterial factors corresponding to autolysins (β-N-acetylglucosaminidase) and AHL-lactonases were established. This study would strengthen our understanding for application of different rhizobacteria with various active principles like Pseudomonas and Bacillus as ingredients of a biocontrol mixture.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Evaluation of rhizospheric Pseudomonas and Bacillus as biocontrol tool for Xanthomonas campestris pv campestris

Mishra

Arora

2011

World J Microbiol Biotechnol

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“…The C 7 (HHQ) and C 9 (HNQ) congeners, shown in Fig. 2, were reported by Wells in 1952 (11) whereas the structures of the other series A congeners were later determined by using GC͞MS (32). In contrast, the only reported series B congener is 3,4-dihydroxy-2-heptylquino- line, first isolated in 1959 (33), and later fully characterized and named PQS (7).…”

Section: Haq Identification: Mvfr Is Required For the Production Of Fmentioning

confidence: 98%

“…For series C, the C 7 , C 9 , C 8 , and C 11 congeners have been reported (28,34) and are further discussed below whereas the series E and the series B PQS congeners are identified in this study. The simultaneous mass spectrometric detection of all these HAQ congeners, notably those of series C and E, which have polar N-oxide functions, could not be achieved by GC͞MS (32,35). Positive electrospray ionization MS is better suited than GC͞electron impact-MS for the detection of such relatively basic and͞or polar compounds.…”

Section: Haq Identification: Mvfr Is Required For the Production Of Fmentioning

confidence: 99%

Analysis of Pseudomonas aeruginosa 4-hydroxy-2-alkylquinolines (HAQs) reveals a role for 4-hydroxy-2-heptylquinoline in cell-to-cell communication

Déziel

Lépine

Milot

et al. 2004

Proc. Natl. Acad. Sci. U.S.A.

583

743

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Bacterial communities use ''quorum sensing'' (QS) to coordinate their population behavior through the action of extracellular signal molecules, such as the N-acyl-L-homoserine lactones (AHLs). The versatile and ubiquitous opportunistic pathogen Pseudomonas aeruginosa is a well-studied model for AHL-mediated QS. This species also produces an intercellular signal distinct from AHLs, 3,4-dihydroxy-2-heptylquinoline (PQS), which belongs to a family of poorly characterized 4-hydroxy-2-alkylquinolines (HAQs) previously identified for their antimicrobial activity. Here we use liquid chromatography (LC)͞MS, genetics, and whole-genome expression to investigate the structure, biosynthesis, regulation, and activity of HAQs. We show that the pqsA-E operon encodes enzymes that catalyze the biosynthesis of five distinct classes of HAQs, and establish the sequence of synthesis of these compounds, which include potent cytochrome inhibitors and antibiotics active against human commensal and pathogenic bacteria. We find that anthranilic acid, the product of the PhnAB synthase, is the primary precursor of HAQs and that the HAQ congener 4-hydroxy-2-heptylquinoline (HHQ) is the direct precursor of the PQS signaling molecule. Significantly, whereas phnAB and pqsA-E are positively regulated by the virulence-associated transcription factor MvfR, which is also required for the expression of several QSregulated genes, the conversion of HHQ to PQS is instead controlled by LasR. Finally, our results reveal that HHQ is itself both released from, and taken up by, bacterial cells where it is converted into PQS, suggesting that it functions as a messenger molecule in a cell-to-cell communication pathway. HAQ signaling represents a potential target for the pharmacological intervention of P. aeruginosa-mediated infections.

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“…Until recently, HAQ analysis was indirect and problematic: PQS was quantified by thin-layer chromatography and densitometric analysis [14,15] or by an indirect biological assay [11]; while HAQs were assessed by gas chromatography coupled to electron capture MS [16], which requires prior derivatization. Furthermore, polar N-oxide congeners, which behave poorly in gas chromatography, have to first be reduced to their corresponding quinolines, which can lead to ambiguous results, as P. aeruginosa cultures typically contain both these N-oxides and their corresponding quinolines.…”

mentioning

confidence: 99%

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

Lépine

Milot

Déziel

et al. 2004

J. Am. Soc. Mass Spectrom.

237

243

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The opportunistic pathogen Pseudomonas aeruginosa produces a large array of 4-hydroxy-2-alkylquinolines (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.

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Rapid identification of 4-hydroxy-2-alkylquinolines produced by Pseudomonas aeruginosa using gas chromatography—electron-capture mass spectrometry

Cited by 28 publications

References 13 publications

Evaluation of rhizospheric Pseudomonas and Bacillus as biocontrol tool for Xanthomonas campestris pv campestris

Evaluation of rhizospheric Pseudomonas and Bacillus as biocontrol tool for Xanthomonas campestris pv campestris

Analysis of Pseudomonas aeruginosa 4-hydroxy-2-alkylquinolines (HAQs) reveals a role for 4-hydroxy-2-heptylquinoline in cell-to-cell communication

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

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