The relationship between structure and <i>in vitro</i>
 antibacterial activity of selected isoflavones and their metabolites with special focus on antistaphylococcal effect of demethyltexasin

Hummelova, Jana; Rondevaldova, Johana; Balastikova, A.; Lapčı́k, Oldřich; Kokoška, Ladislav

doi:10.1111/lam.12361

Cited by 42 publications

(27 citation statements)

References 27 publications

(59 reference statements)

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“…The results reported by Hummelova et al . 25 agree partially with our observations, since the isoflavonoids with the strongest S . aureus inhibitory effect were ortho -dihydroxyisoflavones.…”

Section: Discussionsupporting

confidence: 92%

See 1 more Smart Citation

Looking to nature for a new concept in antimicrobial treatments: isoflavonoids from Cytisus striatus as antibiotic adjuvants against MRSA

Abreu

Coqueiro

Sultan³

et al. 2017

Sci Rep

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The spread of multidrug-resistant Staphylococcus aureus strains, including methicillin-resistant S. aureus (MRSA), has shortened the useful life of anti-staphylococcal drugs enormously. Two approaches can be followed to address this problem: screening various sources for new leads for antibiotics or finding ways to disable the resistance mechanisms to existing antibiotics. Plants are resistant to most microorganisms, but despite extensive efforts to identify metabolites that are responsible for this resistance, no substantial progress has been made. Plants possibly use multiple strategies to deal with microorganisms that evolved over time. For this reason, we searched for plants that could potentiate the effects of known antibiotics. From 29 plant species tested, Cytisus striatus clearly showed such an activity and an NMR-based metabolomics study allowed the identification of compounds from the plant extracts that could act as antibiotic adjuvants. Isoflavonoids were found to potentiate the effect of ciprofloxacin and erythromycin against MRSA strains. For the structure-activity relationship (SAR), 22 isoflavonoids were assessed as antibiotic adjuvants. This study reveals a clear synergy between isoflavonoids and the tested antibiotics, showing their great potential for applications in the clinical therapy of infections with antibiotic-resistant microorganisms such as MRSA.

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Section: Discussionsupporting

confidence: 92%

“…aureus inhibitory effect were ortho -dihydroxyisoflavones. Other studies showed that 5,7-dihydroxylation of the flavonoid A-ring was important for anti-MRSA activity 25, 50, 51 and monomethoxy B-ring derivatives were generally found to be more active (antibiotic synergy) than the disubstituted B-ring derivatives 29 .…”

Section: Discussionmentioning

confidence: 97%

Looking to nature for a new concept in antimicrobial treatments: isoflavonoids from Cytisus striatus as antibiotic adjuvants against MRSA

Abreu

Coqueiro

Sultan³

et al. 2017

Sci Rep

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show abstract

“…This observation is in correspondence with previously published reports describing orthodihydroxy groups as the most important structural feature of high biological activity for phenolic compounds (e.g., stilbenes scavenging radicals) [29]. In addition, the increasing effect of antibacterial activity due to the presence of orthodihydroxy groups in structure of selected various classes of polyphenols, such as isoflavones, has also previously been proposed [31].…”

Section: Discussionsupporting

confidence: 90%

The relationship between structure and in vitro antistaphylococcal effect of plant-derived stilbenes

Zakova

Rondevaldova

Bernardos

et al. 2018

AMicr

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Staphylococcus aureus is a major human pathogen that is responsible for both hospital-and community-acquired infections. Stilbenes are polyphenol compounds of plant origin known to possess a variety of pharmacological properties, such as antibacterial, antiviral, and antifungal effects. This study reports the in vitro growth-inhibitory potential of eight naturally occurring stilbenes against six standard strains and two clinical isolates of S. aureus, using a broth microdilution method, and expressing the results as minimum inhibitory concentrations (MICs). Pterostilbene (MICs = 32-128 μg/ml), piceatannol (MICs = 64-256 μg/ml), and pinostilbene (MICs = 128 μg/ml) are among the active compounds that possess the strongest activity against all microorganisms tested, followed by 3′-hydroxypterostilbene, isorhapontigenin, oxyresveratrol, and rhapontigenin with MICs 128-256 μg/ml. Resveratrol (MIC = 256 μg/ml) exhibited only weak inhibitory effect. Furthermore, structure-activity relationships were studied. Hydroxyl groups at ortho-position (B-3′ and -4′) played crucial roles for the inhibitory effect of hydroxystilbene piceatannol. Compounds with methoxy groups at ring A (3′-hydroxypterostilbene, pinostilbene, and pterostilbene) produced stronger effect against S. aureus than their analogues (isorhapontigenin and rhapontigenin) with methoxy groups at ring B. These findings provide arguments for further investigation of stilbenes as prospective leading structures for development of novel antistaphylococcal agents for topical treatment of skin infections.

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“…A n t i m i c r o b i a l s t u d i e s o f i s o l a t e d isoflavone are rarely found in literature. The isoflavone 6,7,4'-trihydroxy-isoflavone showed antibacterial activity against Bacillus cereus ATCC 11778, Listeria monocytogenes ATCC 7644, Staphylococcus aureus ATCC 29213, Staphylococcus epidermidis ATCC 12228 and Streptococcus pyogenes ATCC 19615 at concentrations of 32, 128, 16, 32 and 64 μg/ml (Hummelova et al 2014).…”

Section: Oxidation Inhibition With β-Carotene and Linoleic Acid (Bcb)mentioning

confidence: 99%

Evaluation of the antimicrobial and antioxidant activity of 7-hydroxy-4’, 6-dimethoxy-isoflavone and essential oil from Myroxylon peruiferum L.f

Pereira

Ferreira

et al. 2019

An. Acad. Bras. Ciênc.

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This study evaluated the antibacterial, antifungal, and antioxidant effect of 7-hydroxy-4',6dimethoxy-isoflavone and essential oil of Myroxylon peruiferum. The compound was isolated and its structure elucidated by NMR. The chemical composition of essential oil determined by gC-MS analysis. To evaluation of antimicrobial activity, the Minimum Inhibitory Concentration (MIC), Minimum Bactericidal Concentration (MBC) and Minimum Fungicidal Concentration (MFC) were performed. In addition to analysis of antioxidant activity, DPPH radical scavenging tests, iron chelating assay (FIC), antioxidant reducing power assay (FRAP) and β-carotene bleaching assay (BCB) were performed. For the essential oil were identified 24 organized compounds having as main constituents; Germacrene D (17.2%), α-pinene (14.8%) and E-caryophyllene (10.8%). The results showed that isoflavone (2000 to 156 μg/mL) and essential oil (5.0 to 1.25%) present antibacterial and antifungal activity against Gram-positive bacteria and filamentous fungi. The isoflavone and the essential oil also presented antioxidant activity in all the tests, mainly on inhibition of the oxidation of β-carotene test concentrations ranging from 60 to 100%. In conclusion, isoflavone and essential oil from M. peruiferum present an antimicrobial alternative against gram-positive bacteria, especially of the genus Staphylococcus and dermatophyte fungi of the genus Trichophyton, as well as a natural compound antioxidant.

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The relationship between structure and in vitro antibacterial activity of selected isoflavones and their metabolites with special focus on antistaphylococcal effect of demethyltexasin

Cited by 42 publications

References 27 publications

Looking to nature for a new concept in antimicrobial treatments: isoflavonoids from Cytisus striatus as antibiotic adjuvants against MRSA

Looking to nature for a new concept in antimicrobial treatments: isoflavonoids from Cytisus striatus as antibiotic adjuvants against MRSA

The relationship between structure and in vitro antistaphylococcal effect of plant-derived stilbenes

Evaluation of the antimicrobial and antioxidant activity of 7-hydroxy-4’, 6-dimethoxy-isoflavone and essential oil from Myroxylon peruiferum L.f

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