Antibacterial activity of a novel flavonoid, 7-O-butyl naringenin, against methicillin-resistant Staphylococcus aureus (MRSA)

Lee, Kyoung Ah; Moon, Seong-Yong; Lee, Joo-Yeon; Kim, Kee‐Tae; Park, Yong-Sun; Paik, Hyun‐Dong

doi:10.1007/s10068-013-0272-9

Cited by 32 publications

(25 citation statements)

References 18 publications

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“…pneumoniae cells were killed within one hour. A comparative literature study revealed that ClCl-flav has a higher bactericidal activity, up to 100-fold more active against Gram positive bacteria and up to 8-fold against Gram negative bacteria compared to most of the reported synthetic flavonoids [ 24 – 26 ].…”

Section: Discussionmentioning

confidence: 99%

A novel synthetic flavonoid with potent antibacterial properties: In vitro activity and proposed mode of action

et al. 2018

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The emergence of pathogenic multidrug-resistant bacteria demands new approaches in finding effective antibacterial agents. Synthetic flavonoids could be a reliable solution due to their important antimicrobial activity. We report here the potent in vitro antibacterial activity of ClCl-flav—a novel synthetic tricyclic flavonoid. The antimicrobial effects were tested using the minimum inhibitory concentration (MIC), time kill and biofilm formation assays. Fluorescence microscopy and scanning electron microscopy were employed to study the mechanism of action. MTT test was used to assess the cytotoxicity of ClCl-flav. Our results showed that Gram positive bacteria were more sensitive (MIC = 0.24 μg/mL) to ClCl-flav compared to the Gram negative ones (MIC = 3.9 μg/mL). We found that our compound showed significantly enhanced antibacterial activities, 32 to 72-fold more active than other synthetic flavonoids. ClCl-flav showed bactericidal activity at concentrations ranging from 0.48 to 15.62 μg/mL. At twice the MIC, all Escherichia coli and Klebsiella pneumoniae cells were killed within 1 h. Also ClCl-flav presented good anti-biofilm activity. The mechanism of action is related to the impairment of the cell membrane integrity. No or very low cytotoxicity was evidenced at effective concentrations against Vero cells. Based on the strong antibacterial activity and cytotoxicity assessment, ClCl-flav has a good potential for the design of new antimicrobial agents.

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Section: Discussionmentioning

confidence: 99%

A novel synthetic flavonoid with potent antibacterial properties: In vitro activity and proposed mode of action

et al. 2018

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“…Lee et al reported that 7- O -butylnaringenin displayed antimicrobial activity against methicillin-resistant S. aureus (MRSA). The action of this derivative was compared with that of naturally occurring flavonoids—quercetin and naringenin—and has been described as Minimal Inhibitory Concentration (MIC) [ 12 ]. In our research, 9a , which has a dodecyl group attached to the C-7 position in naringenin, exhibited the best inhibitory effect against S. aureus DSM799 among all the tested O -alkyl derivatives ( Figure 2 ).…”

Section: Resultsmentioning

confidence: 99%

“…Derivatives with a benzyl group at the C-7 position regulate apoptosis in human colorectal carcinoma (RKO) cells as a result of the intracellular production of reactive oxygen species (ROS) [ 11 ]. Furthermore, 7- O -butylnaringenin exhibits antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA), which is one of the most important pathogens in hospitals [ 12 ].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Biological Activity of Novel O-Alkyl Derivatives of Naringenin and Their Oximes

et al. 2017

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O-Alkyl derivatives of naringenin (1a–10a) were prepared from naringenin using the corresponding alkyl iodides and anhydrous potassium carbonate. The resulting products were used to obtain oximes (1b–10b). All compounds were tested for antimicrobial activity against Escherichia coli ATCC10536, Staphylococcus aureus DSM799, Candida albicans DSM1386, Alternaria alternata CBS1526, Fusarium linii KB-F1, and Aspergillus niger DSM1957. The resulting biological activity was expressed as the increase in optical density (ΔOD). The highest inhibitory effect against E. coli ATCC10536 was observed for 7,4′-di-O-pentylnaringenin (8a), 7-O-dodecylnaringenin (9a), naringenin oxime (NG-OX), 7,4′-di-O-pentylnaringenin oxime (8b), and 7-O-dodecylnaringenin oxime (9b) (ΔOD = 0). 7-O-dodecylnaringenin oxime (9b) also inhibited the growth of S. aureus DSM799 (ΔOD = 0.35) and C. albicans DSM1386 (ΔOD = 0.22). The growth of A. alternata CBS1526 was inhibited as a result of the action of 7,4′-di-O-methylnaringenin (2a), 7-O-ethylnaringenin (4a), 7,4′-di-O-ethylnaringenin (5a), 5,7,4′-tri-O-ethylnaringenin (6a), 7,4′-di-O-pentylnaringenin (8a), and 7-O-dodecylnaringenin (9a) (ΔOD in the range of 0.49–0.42) in comparison to that of the control culture (ΔOD = 1.87). In the case of F. linii KB-F1, naringenin (NG), 7,4′-di-O-dodecylnaringenin (10a), 7-O-dodecylnaringenin oxime (9b), and 7,4′-di-O-dodecylnaringenin oxime (10b) showed the strongest effect (ΔOD = 0). 7,4′-Di-O-pentylnaringenin (8a) and naringenin oxime (NG-OX) hindered the growth of A. niger DSM1957 (ΔOD = 0).

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“…Also, they have advantages over antibiotics that they have multiple activities acting on the cells, so it is hard for bacteria to develop resistance to them (11). Thus, many approaches have been carried out to seek natural origin flavonoids having anti-bacterial effect and develop to make them have stronger efficacy (12). For example, catechins can disrupt the bacterial membrane by interacting with membrane and inhibiting enzymes (13).…”

Section: Introductionmentioning

confidence: 99%

Naringenin as an antibacterial reagent controlling of biofilm formation and fatty acid metabolism in MRSA

Song

Bhatia

Gurav

et al. 2020

Preprint

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24MRSA is Methicillin-resistant Staphylococcus aureus and they are widespread and making 25 trouble in treatment in communities and surgical areas. MRSA have been adapted to antibiotics 26 so that they can block the access of antibiotics physically or chemically deactivate it or modify 27 the precursor of the target. Flavonoids are secondary metabolites which are naturally produced 28 by plant or fungus and they are acting generally as pigment, quorum sensing molecules, 29 antibiotics to other competitive microorganisms. Their natural origins and multiple activities 30 have drawn much attention to be developed as the potential drugs since flavonoids could be a 31 good candidate to overcome antibiotic resistant bacteria. Among various flavonoids, we found 32 out naringenin has antibacterial activity on MRSA and Δagr mutants which are more resistance 33 than MRSA to beta-lactam antibiotics by decreasing biofilm formation dramatically and 34 decreasing the secretion of fatty acid. It also showed high synergetic activity with oxacillin to 35 both antibacterial activity and biofilm inhibition. Considering the number of flavonoids, our 36 experiments expand the possibility of the use of flavonoids to MRSA.37 38

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Antibacterial activity of a novel flavonoid, 7-O-butyl naringenin, against methicillin-resistant Staphylococcus aureus (MRSA)

Cited by 32 publications

References 18 publications

A novel synthetic flavonoid with potent antibacterial properties: In vitro activity and proposed mode of action

A novel synthetic flavonoid with potent antibacterial properties: In vitro activity and proposed mode of action

Synthesis and Biological Activity of Novel O-Alkyl Derivatives of Naringenin and Their Oximes

Naringenin as an antibacterial reagent controlling of biofilm formation and fatty acid metabolism in MRSA

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