Anti-MRSA activity of sophoraflavanone G and synergism with other antibacterial agents

Sakagami, Yoshikazu; Mimura, Mayumi; Kajimura, K.; Yokoyama, H.; Iinuma, Munekazu; Tanaka, Tsukasa; Ohyama, Masayoshi

doi:10.1046/j.1472-765x.1998.00386.x

Cited by 28 publications

(13 citation statements)

References 7 publications

(11 reference statements)

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“…Binary combinations of sophoraflavanone G, a geranylated flavanone isolated from Sophora spp., with vancomycin, fosfomycin, methicillin, cefzonam, gentamicin, minocycline, or levofloxacin, have inhibited 27 strains of MRSA. An increase in the inhibitory activity of vancomycin during the second stage of the synthesis of the bacterial cell wall has been postulated as a mechanism fostering the synergy that results from combining it with sophoraflavanone G (Sakagami et al 1998).…”

Section: Resultsmentioning

confidence: 99%

C-Geranylated flavonoids fromPaulownia tomentosafruits with antimicrobial potential and synergistic activity with antibiotics

Navrátilová

Nešuta

Vančatová

et al. 2016

Pharmaceutical Biology

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Context C-6-Geranylated flavonoids possess promising biological activities. These substances could be a source of lead compounds for the development of therapeutics. Objective The study was designed to evaluate their antibacterial and antileishmanial activity. Materials and methods C-6-Geranylated flavanones were tested in micromolar concentrations against promastigote forms of Leishmania brazilensis, L. donovani, L. infantum, and L. panamensis against methicillin-resistant Staphylococcus aureus (MRSA); and synergistic potential with antibiotics was analyzed. IC50 values (after 72 h) were calculated and compared with that of miltefosine. Flow cytometry and DNA fragmentation analysis were used the mechanism of the effect. Geranylated flavanones or epigallocatechin gallate were combined with oxacillin, tetracycline, and ciprofloxacin, and the effects of these two-component combinations were evaluated. Minimal inhibitory concentrations (MICs) and minimal bactericidal concentrations (MBCs) were established (after 24 h), the synergy was measured by the checkerboard titration technique, and the sums of the fractional inhibitory concentrations (∑FICs) were computed. Results 3'-O-Methyl-5'-O-methyldiplacone and 3'-O-methyldiplacone showed good antileishmanial activities (IC50 8-42 μM). 3'-O-Methyl-5'-hydroxydiplacone activates the apoptotic death at leishmanias, the effect of 3'-O-methyl-5'-O-methyldiplacone has another mechanism. The test of the antibacterial activity showed good effects of 3'-O-methyldiplacol and mimulone against MRSA (MIC 2-16 μg/mL), and in six cases, the results showed synergistic effects when combined with oxacillin. Synergistic effects were also found for the combination of epigallocatechin gallate with tetracycline or oxacillin. Conclusion This work demonstrates anti-MRSA and antileishmanial potential of geranylated flavanones and uncovers their promising synergistic activities with antibiotics. In addition, the mechanism of antileishmanial effect is proposed.

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Section: Resultsmentioning

confidence: 99%

C-Geranylated flavonoids fromPaulownia tomentosafruits with antimicrobial potential and synergistic activity with antibiotics

Navrátilová

Nešuta

Vančatová

et al. 2016

Pharmaceutical Biology

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“…Many research groups have gone one step further and either isolated and identified the structure of flavonoids that possess antibacterial activity, or quantified the activity of commercially available flavonoids. Examples of such flavonoids are apigenin [65][66][67][68][69][70][71][72][73], galangin [35,[74][75][76][77], pinocembrin [78,79], ponciretin [80,81], genkwanin [66,82], sophoraflavanone G and its derivatives [29,[83][84][85], naringin and naringenin [29,60,86,87], epigallocatechin gallate and its derivatives [74,[88][89][90][91][92][93][94][95], luteolin and luteolin 7glucoside [69,73,96], quercetin, 3-O-methylquercetin and various quercetin glycosides [60,65,72,87,[97][98]…”

Section: Reports Of Flavonoids Possessing Antibacterial Activitymentioning

confidence: 99%

“…Some researchers have reported synergy between naturally occurring flavonoids and other antibacterial agents against resistant strains of bacteria. Examples of these include epicatechin gallate [122][123][124][125] and sophoraflavanone G [83,84]. At least one group has demonstrated synergy between flavonoids with antibacterial activity [126].…”

Section: Reports Of Flavonoids Possessing Antibacterial Activitymentioning

confidence: 99%

“…A research team that had previously found sophoraflavanone G to have intensive antibacterial activity against MRSA and streptococci [83][84][85] recently reported attempts to elucidate the mechanism of action of this flavanone [139]. The effect of sophoraflavanone G on membrane fluidity was studied using liposomal model membranes and compared with the less active flavanone naringenin, which lacks 8-lavandulyl and 2 -hydroxyl groups.…”

Section: Inhibition Of Cytoplasmic Membrane Functionmentioning

confidence: 99%

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Antimicrobial activity of flavonoids

Cushnie

Lamb

2005

International Journal of Antimicrobial Agents

3,417

1,980

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Flavonoids are ubiquitous in photosynthesising cells and are commonly found in fruit, vegetables, nuts, seeds, stems, flowers, tea, wine, propolis and honey. For centuries, preparations containing these compounds as the principal physiologically active constituents have been used to treat human diseases. Increasingly, this class of natural products is becoming the subject of anti-infective research, and many groups have isolated and identified the structures of flavonoids possessing antifungal, antiviral and antibacterial activity. Moreover, several groups have demonstrated synergy between active flavonoids as well as between flavonoids and existing chemotherapeutics. Reports of activity in the field of antibacterial flavonoid research are widely conflicting, probably owing to inter- and intra-assay variation in susceptibility testing. However, several high-quality investigations have examined the relationship between flavonoid structure and antibacterial activity and these are in close agreement. In addition, numerous research groups have sought to elucidate the antibacterial mechanisms of action of selected flavonoids. The activity of quercetin, for example, has been at least partially attributed to inhibition of DNA gyrase. It has also been proposed that sophoraflavone G and (-)-epigallocatechin gallate inhibit cytoplasmic membrane function, and that licochalcones A and C inhibit energy metabolism. Other flavonoids whose mechanisms of action have been investigated include robinetin, myricetin, apigenin, rutin, galangin, 2,4,2'-trihydroxy-5'-methylchalcone and lonchocarpol A. These compounds represent novel leads, and future studies may allow the development of a pharmacologically acceptable antimicrobial agent or class of agents.

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“…The synergism of SFG had been observed with VCM and also with FOM, and partial synergism with methicillin, cefzonam, GM and LVFX (Sakagami et al, 1998).…”

Section: Discussionmentioning

confidence: 94%

Anti-VRE and Anti-MRSA Activities of New Quinolones and Their Synergism with Commercial Antibiotics. Part 2

et al. 2008

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Anti-MRSA activity of sophoraflavanone G and synergism with other antibacterial agents

Cited by 28 publications

References 7 publications

C-Geranylated flavonoids fromPaulownia tomentosafruits with antimicrobial potential and synergistic activity with antibiotics

C-Geranylated flavonoids fromPaulownia tomentosafruits with antimicrobial potential and synergistic activity with antibiotics

Antimicrobial activity of flavonoids

Anti-VRE and Anti-MRSA Activities of New Quinolones and Their Synergism with Commercial Antibiotics. Part 2

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