Synthesis of (R)-norbgugaine and its potential as quorum sensing inhibitor against Pseudomonas aeruginosa

Majik, Mahesh S.; Naik, Deepak; Bhat, Chinmay; Tilve, Santosh G.; Tilvi, Supriya; D’Souza, Lisette

doi:10.1016/j.bmcl.2013.02.051

Cited by 51 publications

(25 citation statements)

References 47 publications

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“…The non‐methylated version of the pyrrolidin alkaloid ( R )‐norbgugaine superficially resembles 3‐oxo‐C12‐HSL and inhibited swarming motility and production of virulence factors of P. aeruginosa . The anti‐inflammatory drugs diclofenac and also ketoprofen were shown to inhibit swarming motility of P. aeruginosa at 5 m m concentration without any growth inhibition.…”

Section: Swarming and Bacterial Signalingmentioning

confidence: 99%

“…[54] The non-methylated version of the pyrrolidin alkaloid (R)norbgugaine superficially resembles 3-oxo-C12-HSLa nd inhibited swarming motility and production of virulence factors of P. aeruginosa. [55] The anti-inflammatory drugs diclofenac and also ketoprofen were shown to inhibit swarming motility of P. aeruginosa at 5mm concentration withouta ny growth inhibition. Reduced production of virulence factors as wella sa ctivity in an AHL-quorum-sensingi nhibition screen suggested that these compounds inhibited swarming through the quorum-sensing circuits with the molecular targets yet to be identified.…”

Section: Blockingahl Receptorsmentioning

confidence: 99%

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Inhibitors of Bacterial Swarming Behavior

Rütschlin

Böttcher

2019

Chemistry A European J

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Bacteria can migrate in groups of flagella‐driven cells over semisolid surfaces. This coordinated form of motility is called swarming behavior. Swarming is associated with enhanced virulence and antibiotic resistance of various human pathogens and may be considered as favorable adaptation to the diverse challenges that microbes face in rapidly changing environments. Consequently, the differentiation of motile swarmer cells is tightly regulated and involves multi‐layered signaling networks. Controlling swarming behavior is of major interest for the development of novel anti‐infective strategies. In addition, compounds that block swarming represent important tools for more detailed insights into the molecular mechanisms of the coordination of bacterial population behavior. Over the past decades, there has been major progress in the discovery of small‐molecule modulators and mechanisms that allow selective inhibition of swarming behavior. Herein, an overview of the achievements in the field and future directions and challenges will be presented.

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Section: Swarming and Bacterial Signalingmentioning

confidence: 99%

Section: Blockingahl Receptorsmentioning

confidence: 99%

Inhibitors of Bacterial Swarming Behavior

Rütschlin

Böttcher

2019

Chemistry A European J

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“…In the presence of a quorum sensing inhibitory compound, the motility and therefore the virulence will be limited. 11 Six different forms of bacterial movement have been described including Pharmacognosy Journal, Vol 10, Issue 5, Sep-Oct, 2018 swimming, swarming, twitching, gliding, sliding and darting. 12 These various forms of surface motility enable bacteria to increase their efficiency of nutrient uptake, avoid toxic substances, move to preferred hosts and provide access to optimal colonization sites within, and spread themselves into the environment.…”

Section: Introductionmentioning

confidence: 99%

Attenuation of Pseudomonas aeruginosa Virulence by Some Indonesian Medicinal Plants Ethanolic Extract

Pratiwi¹,

Handayani²

2018

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Context:One strategy to address the emergence of infectious diseases supported by the increasing cases of microbial antibiotic resistance is the development of anti-pathogenic drugs, a quorum quenching compound(s) capable of inhibiting microbial communication (quorum sensing inhibitor). Pseudomonas aeruginosa is one of the most common source of chronic opportunistic infections, which demonstrates the most consistent resistance to antimicrobial agents. Quorum sensing (QS) controls secretion of virulence factors in P. aeruginosa. Aim: This study aims to discover quorum sensing inhibitors (QSI) from some Indonesian medicinal plants ethanol extract to analyze their inhibitory activities against QS-mediated virulence factors in P. aeruginosa. Settings and Design: In-vitro experimental study-laboratory setting Materials and Methods: Indonesian medicinal plant ethanolic extracts were tested for their capability to inhibit P. aeruginosa motility, biofilm formation using microtiter plate method, pyocyanin and LasA production using LasA staphylolytic assay. Statistical analysis used: Statistical significance of the data were determined using one way ANOVA, followed by Dunnett's test. Differences were considered significant with P values of 0.05 or less. Results: Ethanolic extract of T. catappa leaves and A. alitilis flower capable to inhibit P. aeruginosa motility as well as pyocyanin production and biofilm formation. Both extracts also showed capability in reducing LasA protease production. Conclusion: T. catappa and A. alitilis are an interesting sources of innovative plant derived quorum quenching compound(s), thus can be used in the development of new antipathogenic drug.

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“…Therefore, derivatives 78 and 79 displayed a less familiar performance against the production of pyocyanin at 100 μM . Moreover, the natural product ( R )‐norbgugaine ( 80 ) was tested as a QS inhibitor for investigating pyocyanin production . 2‐Heptyl‐3‐hydroxy‐4(1 H ) quinolone, known as Pseudomonas quinolone signal (PQS), is the third signaling molecule in the QS system, which can interact with the two AHL systems ( las and rhl ) and provide a regulatory link between these two AHL‐based QS systems .…”

Section: Pigments Of Representative Colored Pathogens and Their Inhibmentioning

confidence: 99%

Targeting virulence factors as an antimicrobial approach: Pigment inhibitors

et al. 2019

Medicinal Research Reviews

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The fascinating and dangerous colored pathogens contain unique chemically pigmented molecules, which give varied and efficient assistance as virulence factors to the crucial reproduction and growth of microbes. Therefore, multiple novel strategies and inhibitors have been developed in recent years that target virulence factor pigments. However, despite the importance and significance of this topic, it has not yet been comprehensively reviewed. Moreover, research groups around the world have made successful progress against antibacterial infections by targeting pigment production, including our serial works on the discovery of CrtN inhibitors against staphyloxanthin production in Staphylococcus aureus. On the basis of the previous achievements and recent progress of our group in this field, this article will be the first comprehensive review of pigment inhibitors against colored pathogens, especially S. aureus infections, and this article includes design strategies, representative case studies, advantages, limitations, and perspectives to guide future research.

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Synthesis of (R)-norbgugaine and its potential as quorum sensing inhibitor against Pseudomonas aeruginosa

Cited by 51 publications

References 47 publications

Inhibitors of Bacterial Swarming Behavior

Inhibitors of Bacterial Swarming Behavior

Attenuation of Pseudomonas aeruginosa Virulence by Some Indonesian Medicinal Plants Ethanolic Extract

Targeting virulence factors as an antimicrobial approach: Pigment inhibitors

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