Aurone derivatives as promising antibacterial agents against resistant Gram-positive pathogens

Olleik, Hamza; Yahiaoui, Samir; Roulier, Brayan; Courvoisier-Dezord, Élise; Perrier, Josette; Pérès, Basile; Hijazi, Akram; Baydoun, Elias; Raymond, Josette; Boumendjel, Ahcène; Maresca, Marc; Haudecoeur, Romain

doi:10.1016/j.ejmech.2019.01.022

Cited by 58 publications

(56 citation statements)

References 28 publications

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“…Mycobacterium smegmatis (mc2155, ATCC 700084) was used as model of Mycobacterium species. Bacteria were cultured as previously described [ 15 , 16 , 17 , 18 ] Briefly, most of the bacterial strains were routinely grown on Luria Bertani (LB) agar plates and LB broth at 37 °C in aerobic condition except H. pylori that was grown in BHI in micro-aerobic condition using microaerobic BD GasPak generator (Sigma-Aldrich, Lyon, France). M. smegmatis was cultured in Middlebrook 7H10 agar plate and Middlebrook 7H10 broth at 37 °C in aerobic condition.…”

Section: Methodsmentioning

confidence: 99%

“…Antimicrobial activity of berberine and its derivatives was evaluated by determination of their minimal inhibitory concentration (MIC) using two-fold serial dilutions in bacterial liquid media following the National Committee of Clinical Laboratory Standards (NCCLS, 1997) as previously described [ 15 , 16 , 17 , 18 ]. Briefly, for most of the bacteria, single colonies of the different bacterial strains cultured on specific agar plates were used to inoculate 3 mL of Mueller-Hinton (MH), except C. difficile , C. perfringens , H. pylori , E. faecalis , and S. pyogenes that were cultured in 3 mL of BHI and or M. smegmatis that was cultured in 3 mL of Middlebrook 7H10 broth.…”

Section: Methodsmentioning

confidence: 99%

“…Experiments were conducted in independent triplicate (n = 3). Antimicrobial activity of berberine and berberine’s derivatives was also evaluated by determination of the minimal bactericidal concentration (MBC), i.e., the minimum concentration of the test compound killing 99.9% of the bacteria as previously described [ 15 ]. MBCs were measured by streaking 10 µL of wells with no observed growth of previously prepared MIC plates on agar plates.…”

Section: Methodsmentioning

confidence: 99%

“…The toxicity of berberine and berberine’s derivatives on human cells was evaluated using resazurin assay as previously described [ 15 , 16 , 17 , 19 , 20 , 21 ]. Human cells used were BEAS (ATCC CRL-9609), Caco2 (ATCC HTB-37) and HepG2 (ATCC HB-8065) corresponding respectively to human airway epithelial cells, intestinal epithelial cells and liver cells.…”

Section: Methodsmentioning

confidence: 99%

“…Membrane permeabilization by berberine derivatives was evaluated using the cell-impermeable DNA/RNA probe propidium iodide as previously explained [ 15 , 16 , 22 , 23 ]. Logarithmic growing bacterial suspensions were prepared from overnight bacterial suspension by 1 in 10 dilution.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis and Evaluation of the Antibacterial Activities of 13-Substituted Berberine Derivatives

et al. 2020

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The biological activities of berberine, a natural plant molecule, are known to be affected by structural modifications, mostly at position 9 and/or 13. A series of new 13-substituted berberine derivatives were synthesized and evaluated in term of antimicrobial activity using various microorganisms associated to human diseases. Contrarily to the original molecule berberine, several derivatives were found strongly active in microbial sensitivity tests against Mycobacterium, Candida albicans and Gram-positive bacteria, including naïve or resistant Bacillus cereus, Staphylococcus aureus and Streptococcus pyogenes with minimal inhibitory concentration (MIC) of 3.12 to 6.25 µM. Among the various Gram-negative strains tested, berberine’s derivatives were only found active on Helicobacter pylori and Vibrio alginolyticus (MIC values of 1.5–3.12 µM). Cytotoxicity assays performed on human cells showed that the antimicrobial berberine derivatives caused low toxicity resulting in good therapeutic index values. In addition, a mechanistic approach demonstrated that, contrarily to already known berberine derivatives causing either membrane permeabilization, DNA fragmentation or interacting with FtsZ protein, active derivatives described in this study act through inhibition of the synthesis of peptidoglycan or RNA. Overall, this study shows that these new berberine derivatives can be considered as potent and safe anti-bacterial agents active on human pathogenic microorganisms, including ones resistant to conventional antibiotics.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Synthesis and Evaluation of the Antibacterial Activities of 13-Substituted Berberine Derivatives

et al. 2020

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Longevity effects of hispidol in Caenorhabditis elegans

et al. 2020

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In this study, we investigated the longevity effects of hispidol, a 6,4 0-dihydroxyaurone, using the Caenorhabditis elegans model system. Our lifespan assay data revealed that hispidol could prolong the lifespan of wild-type worms under normal culture condition. Moreover, hispidol increased the survival rate of the worms against a heat stress condition through up-regulated expressions of HSP-16.2. Similarly, hispidol protected worms from paraquat-induced oxidative stress. We also found that the hispidol elevated the activities of antioxidant enzymes, thereby attenuating the generation of intracellular reactive oxygen species. These results suggest that the enhancement of lifespan and stress resistance by the hispidol treatment might be attributed to its strong in vivo antioxidant capacity and regulation of stress proteins. Further tests on the aging-related factors revealed that hispidol could regulate the speed of pharyngeal pumping, indicating the association of dietary restriction with the hispidol-mediated longevity. However, there were no significant alterations in the body length of the worms between the groups. We then investigated the effects of hispidol on body movement and lipofuscin accumulation in aged worms. Interestingly, these healthspan parameters were strongly improved by the hispidol treatment. Our genetic studies showed no significant change in the lifespan of the daf-16 null mutants by hispidol supplementation. In addition, enhanced nuclear translocation of DAF-16 was observed in the hispidol-fed DAF-16::GFP fused transgenic mutants, suggesting the requirement of DAF-16/FOXO activation for the longevity effect of hispidol.

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Asymmetric Synthesis of Quaternary α‐Aryl Stereocentres in Benzofuran‐3(2H)‐Ones Using Decarboxylative Asymmetric Allylic Alkylation

McNeill,

Twamley,

Guiry

2024

Chemistry A European J

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The Pd‐catalysed decarboxylative asymmetric allylic alkylation (DAAA) has been applied to the enantioselective synthesis of sterically hindered benzofuran‐3(2H)‐one‐derived α‐aryl‐β‐keto esters employing the (R,R)‐ANDEN phenyl Trost ligand. A range of substrates were synthesised, employing previously developed aryllead triacetate methodology to install various aryl groups. The resulting α‐aryl‐α‐allyl benzofuran‐3(2H)‐one DAAA products were obtained in moderate to high yields and in enantioselectivities of up to 96% ee, with the best results observed for substrates containing a di‐ortho‐substitution pattern on the aryl ring as well as naphthyl‐containing substrates.

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Aurone derivatives as promising antibacterial agents against resistant Gram-positive pathogens

Cited by 58 publications

References 28 publications

Synthesis and Evaluation of the Antibacterial Activities of 13-Substituted Berberine Derivatives

Synthesis and Evaluation of the Antibacterial Activities of 13-Substituted Berberine Derivatives

Longevity effects of hispidol in Caenorhabditis elegans

Asymmetric Synthesis of Quaternary α‐Aryl Stereocentres in Benzofuran‐3(2H)‐Ones Using Decarboxylative Asymmetric Allylic Alkylation

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