Comparison of seven structurally related coumarins on the inhibition of Quorum sensing of Pseudomonas aeruginosa and Chromobacterium violaceum

D’Almeida, Romina E.; Molina, R.; Viola, Carolina María; Luciardi, María Constanza; Peñalver, Carlos Nieto; Bardón, Alicia; Arena, Mario Eduardo

doi:10.1016/j.bioorg.2017.05.011

Cited by 56 publications

(34 citation statements)

References 33 publications

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“…In a similar study, quercetin 4′-O-β-D glucopyranoside, without impacting the growth of pathogens such as C. violaceum 12472, P. aeruginosa PAO1, S. marcescens , and L. monocytogenes , significantly inhibited ( P < 0·05) the biofilm formation and production of virulence factors including pyocyanin, protease, and elastase at sublethal doses (Al-Yousef et al, 2017 ). Further, our findings are in accordance with other results published on methyl eugenol (Abraham et al, 2012 ), eugenol (Zhou et al, 2013 ), carvacrol (Burt et al, 2014 ), caffeine (Husain et al, 2015a ), menthol (Husain et al, 2015b ), and coumarins (D'Almeida et al, 2017 ). Owing to the previous report on QS inhibition by palmitic acid and linoleic acid (Widmer et al, 2007 ), it is envisaged that the QS inhibitory property of the PCMF is due to the presence of palmitic acid, linoleic acid, and bakuchiol.…”

Section: Resultssupporting

confidence: 93%

Seed Extract of Psoralea corylifolia and Its Constituent Bakuchiol Impairs AHL-Based Quorum Sensing and Biofilm Formation in Food- and Human-Related Pathogens

Husain

Ahmad

Khan

et al. 2018

Front. Cell. Infect. Microbiol.

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The emergence of multi-drug resistance in pathogenic bacteria in clinical settings as well as food-borne infections has become a serious health concern. The problem of drug resistance necessitates the need for alternative novel therapeutic strategies to combat this menace. One such approach is targeting the quorum-sensing (QS) controlled virulence and biofilm formation. In this study, we first screened different fractions of Psoralea corylifolia (seed) for their anti-QS property in the Chromobacterium violaceum 12472 strain. The methanol fraction was found to be the most active fraction and was selected for further bioassays. At sub-inhibitory concentrations, the P. corylifolia methanol fraction (PCMF) reduced QS-regulated virulence functions in C. violaceum CVO26 (violacein); Pseudomonas aeruginosa (elastase, protease, pyocyanin, chitinase, exopolysaccharides (EPS), and swarming motility), A. hydrophila (protease, EPS), and Serratia marcescens (prodigiosin). Biofilm formation in all the test pathogens was reduced significantly (p ≤ 0.005) in a concentration-dependent manner. The β-galactosidase assay showed that the PCMF at 1,000 μg/ml downregulated las-controlled transcription in PAO1. In vivo studies with C. elegans demonstrated increased survival of the nematodes after treatment with the PCMF. Bakuchiol, a phytoconstituent of the extract, demonstrated significant inhibition of QS-regulated violacein production in C. violaceum and impaired biofilm formation in the test pathogens. The molecular docking results suggested that bakuchiol efficiently binds to the active pockets of LasR and RhlR, and the complexes were stabilized by several hydrophobic interactions. Additionally, the molecular dynamics simulation of LasR, LasR–bakuchiol, RhlR, and RhlR–bakuchiol complexes for 50 ns revealed that the binding of bakuchiol to LasR and RhlR was fairly stable. The study highlights the anti-infective potential of the PCMF and bakuchiol instead of bactericidal or bacteriostatic action, as the extract targets QS-controlled virulence and the biofilm.

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Section: Resultssupporting

confidence: 93%

Seed Extract of Psoralea corylifolia and Its Constituent Bakuchiol Impairs AHL-Based Quorum Sensing and Biofilm Formation in Food- and Human-Related Pathogens

Husain

Ahmad

Khan

et al. 2018

Front. Cell. Infect. Microbiol.

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“…As coumarin has been identified as a potent antivirulence molecule, and because different substitutions in specific sites of the coumarin molecule can affect its biological activity (Barot et al 2015 ), a SAR analysis was a logical undertaking in relation to understanding QSI and antibiofilm activity. D'Almeida et al ( 2017 ) followed such an approach to test if the different substitutions on the coumarin structure could affect the QSI activity (D'Almeida et al 2017 ). Using P. aeruginosa and C. violaceum as test species, D’Almeida and colleagues (D'Almeida et al 2017 ) performed a comparison of seven structurally related coumarins (coumarin and different hydroxylated derivatives).…”

Section: Structure-function Analysis Of the Qsi And Antibiofilm Activmentioning

confidence: 99%

“…D'Almeida et al ( 2017 ) followed such an approach to test if the different substitutions on the coumarin structure could affect the QSI activity (D'Almeida et al 2017 ). Using P. aeruginosa and C. violaceum as test species, D’Almeida and colleagues (D'Almeida et al 2017 ) performed a comparison of seven structurally related coumarins (coumarin and different hydroxylated derivatives). Initially using a bioassay with the QS biosensor C. violaceum CV026, and adding exogenous hexanoyl homoserine lactone (HHL), the authors demonstrated that all the different coumarins tested, with the exception of 4-hydroxycoumarin and dihydrocoumarin, were able to inhibit the violacein production.…”

Section: Structure-function Analysis Of the Qsi And Antibiofilm Activmentioning

confidence: 99%

Coumarin: a novel player in microbial quorum sensing and biofilm formation inhibition

Reen

Gutiérrez‐Barranquero

Parages

et al. 2018

Appl Microbiol Biotechnol

106

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Antibiotic resistance is a growing threat worldwide, causing serious problems in the treatment of microbial infections. The discovery and development of new drugs is urgently needed to overcome this problem which has greatly undermined the clinical effectiveness of conventional antibiotics. An intricate cell-cell communication system termed quorum sensing (QS) and the coordinated multicellular behaviour of biofilm formation have both been identified as promising targets for the treatment and clinical management of microbial infections. QS systems allow bacteria to adapt rapidly to harsh conditions, and are known to promote the formation of antibiotic tolerant biofilm communities. It is well known that biofilm is a recalcitrant mode of growth and it also increases bacterial resistance to conventional antibiotics. The pharmacological properties of coumarins have been well described, and these have included several that possess antimicrobial properties. More recently, reports have highlighted the potential role of coumarins as alternative therapeutic strategies based on their ability to block the QS signalling systems and to inhibit the formation of biofilms in clinically relevant pathogens. In addition to human infections, coumarins have also been found to be effective in controlling plant pathogens, infections in aquaculture, food spoilage and in reducing biofouling caused by eukaryotic organisms. Thus, the coumarin class of small molecule natural product are emerging as a promising strategy to combat bacterial infections in the new era of antimicrobial resistance.

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“…Inhibition of violacein production of C. violaceum is commonly used as an indicator of QS inhibition in gram-negative bacteria ( 31 , 32 ). The QS mechanism in C. violaceum ATCC 12472 is controlled by the CviI/CviR system (Luxl/LuxR homologs), correlated with the production of the purple pigment violacein in response to threshold concentrations of the autoinducer N-hexanoyl homoserine lactone ( 61 ). EONEs at sub-MICs were tested.…”

Section: Resultsmentioning

confidence: 99%

Rheological Behavior, Antimicrobial and Quorum Sensig Inhibition Study of an Argentinean Oregano Essential Oil Nanoemulsion

et al. 2020

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In this study, Argentinean oregano essential oil (OEO) nanoemulsions (NEs) were developed. Four NEs were prepared: a control (CNE), EONE1 (10.6 mg EO/g NE), EONE2 (106 mg EO/ g NE), and EONE3 (160 mg EO/g NE) and tested for antimicrobial activity against Staphylococcus aureus ATCC 13565, Listeria monocytogenes Scott A, Pseudomonas aeruginosa ATCC 14213, and Escherichia coli O157:H7 using a broth microdilution assay and quorum sensing inhibition in a model using Chromobacterium violaceum ATCC 12472, where the production of violacein was quantified. The chemical composition of the EO was determined by gas chromatography–mass spectrometry. The average particle size (nm) and polydispersity index were monitored over 14 days at two different storage temperatures (4 and 23°C). A rheological behavior study was carried out using a dynamic shear rheometer, and flow curves, as well as viscoelastic properties, were determined. E. coli and L. monocytogenes were the most sensitive microorganisms to EONE (MIC of 2 and 5 mg/ml for EOEN3). Sub-MICs for NE were found at lower concentrations than those for pure EO. A significant reduction in violet pigment intensity and colorless coloration ( p < 0.05) were observed at different NE concentrations concerning the control sample. The flow behavior index ( n ) decreased, and the consistency index (k) increased when the EO concentration was increased. CNE, EONE1, and EONE2 showed liquid-like behavior (G′ < G″) in the low-frequency region, whereas a solid-like behavior (G′ > G″) was observed in the high-frequency region, presenting a viscoelastic behavior, appearing as a wormlike micellar solution. For EONE3, a strong increase in both moduli was observed with increasing OEO concentration. The G′ was about one order of magnitude higher than the G″ over the whole frequency range, indicating the presence of a gel-like structure. The incorporation of EOs into an NE increased their stability, lowering the particle size, leading to a wormlike micelle with higher viscosity. Moreover, this NE had good antimicrobial activity and novel quorum-sensing inhibition activity. The results of this study indicated that Argentinean OEO NE could be used in a food system as a natural and stable antimicrobial agent.

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Comparison of seven structurally related coumarins on the inhibition of Quorum sensing of Pseudomonas aeruginosa and Chromobacterium violaceum

Cited by 56 publications

References 33 publications

Seed Extract of Psoralea corylifolia and Its Constituent Bakuchiol Impairs AHL-Based Quorum Sensing and Biofilm Formation in Food- and Human-Related Pathogens

Seed Extract of Psoralea corylifolia and Its Constituent Bakuchiol Impairs AHL-Based Quorum Sensing and Biofilm Formation in Food- and Human-Related Pathogens

Coumarin: a novel player in microbial quorum sensing and biofilm formation inhibition

Rheological Behavior, Antimicrobial and Quorum Sensig Inhibition Study of an Argentinean Oregano Essential Oil Nanoemulsion

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