Reduction of membrane fluidity by antibacterial sophoraflavanone G isolated from Sophora exigua

Tsuchiya, Hironori; Iinuma, Munekazu

doi:10.1016/s0944-7113(00)80089-6

Cited by 185 publications

(114 citation statements)

References 19 publications

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“…8,18,21) Various flavonoids interact with membrane lipids to change the fluidity. 22,23) The present study has revealed that the membrane-rigidifying effect is greatest in the order of 1, 2, 3 and 4 and that the anti-platelet activity of 3 is enhanced by dimerization as in 1 but reduced by 4′-glucosylation as in 4. Membrane rigidification appears to be one of pharmacological mechanisms underlying the antiaggregatory and disaggregatory effects of the brownish scale of onion.…”

Section: Resultsmentioning

confidence: 51%

Anti-Platelet and Membrane-Rigidifying Flavonoids in Brownish Scale of Onion

Furusawa

Tsuchiya

Nagayama

et al. 2003

JOURNAL OF HEALTH SCIENCE

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The bio-activity of the brownish scale of onion (Allium cepa) was studied together with identifying the active components and addressing the mode of action. A crude MeOH extract (0.5-1.0 mg/ml) showed the inhibitory effects on human platelet aggregation induced by collagen, adenosine 5′-diphosphate (ADP), thrombin and epinephrine. The anti-platelet extract (1.0 µg/ml) rigidified liposomal membranes by acting on the hydrocarbon core more intensively than the surface of membrane lipid bilayers. Serial solvent extractions and chromatographic purifications provided four isolates which were structurally identified as different quercetin dimers (1 and 2), quercetin (3) and quercetin-4′-glucoside (4). The flavonoidal components 1, 3, 2 and 4 (0.5-2 mM) inhibited collagen-induced platelet aggregation in increasing order of intensity. More active 1 and 3 (2 mM) also dissociated the aggregates produced by ADP. The anti-platelet flavonoids (0.25-10 µM) acted on liposomes of the lipid composition resembling human platelets to cause membrane rigidification which was greatest in the order of 1, 2, 3 and 4. The interaction with membrane lipids to modify membrane fluidity appears to be partly responsible for the anti-aggregatory and disaggregatory effects on human platelets. Although the inedible scale of onion is usually regarded as waste, it has the possibility to be a medicinal resource.

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Section: Resultsmentioning

confidence: 51%

Anti-Platelet and Membrane-Rigidifying Flavonoids in Brownish Scale of Onion

Furusawa

Tsuchiya

Nagayama

et al. 2003

JOURNAL OF HEALTH SCIENCE

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“…Antibacterial flavonoids might be having multiple cellular targets, rather than one specific site of action. Tsuchiya and Iinuma, (2000) suggested an alteration of membrane fluidity in hydrophilic and hydrophobic regions in this way flavonoids might reduce the fluidity of outer and inner layers of membranes. Mishra et al (2009) propose that one of the molecular actions of flavonoids is to form complex with proteins through nonspecific forces such as hydrogen bonding and hydrophobic effects, as well as by covalent bond formation, this interactions have the ability to inactivate microbial adhesions, enzymes, cell envelope transport proteins, and so forth.…”

Section: Antimicrobial Activity Of P Americana By-productsmentioning

confidence: 99%

Bioactive characterization of Persea americana Mill. by-products: A rich source of inherent antioxidants

Melgar

Días

Ćirić

et al. 2018

Industrial Crops and Products

128

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A B S T R A C TAvocado (Persea americana Mill.) is a worldwide consumed fruit, with great interest for cosmetic and pharmaceutical industries; however, 30% of avocado fruits are bio-wastes (peels and kernels), converting them into a potential source of bioactive compounds, such as phenolic compounds. Therefore, the hydroethanolic extracts of peels and kernels of Persea america Mill. var. Hass were analysed regarding their individual phenolic profile by HPLC-DAD/ESI-MS and correlated with their antioxidant, antimicrobial and cytotoxic activities. Avocado byproducts presented a very distinct phenolic profile, presenting higher concentration in peels (227.9 mg/g of extract for total phenolic content), mainly in (epi)catechin derivatives (175 mg/g of extract), followed by chlorogenic derivatives (42.9 mg/g of extract). In this study hydrophilic and lipophilic antioxidant assays were performed together for the first time in P. americana by-products, and although kernels showed a great antioxidant potential (EC 50 values ranging from 18.1 to 276 μg/mL), peels presented the highest potential (EC 50 ranging from 11.7 to 152 μg/mL), mainly due to the presence of phenolic compounds, and an overall better performance in the antibacterial assays. Further studies needs to be conducted to better understand the correlation between the presence of phenolic compounds and bioactivities, however, the main objective is to implement these biocompounds in different products and industries, due to results obtained, P. americana peels could be a great alternative in the substitution of synthetic antioxidants.

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“…The structure of the yellow crystalline compound was confirmed by 1 H NMR, 13 C NMR spectra and its melting point (Iinuma et al, 1995). This data revealed that this compound was 5,7,2Ј,4Ј-tetrahydroxy-8-lavandulylflavanone (sophoraflavanone G), previously isolated from Sophora exigua (Tsuchiya and Iinuma, 2000).…”

Section: Resultsmentioning

confidence: 64%

Sophoraflavanone G from Sophora pachycarpa Enhanced the Antibacterial Activity of Gentamycin against Staphylococcus aureus

Fakhimi

Iranshahi

Emami

et al. 2006

Zeitschrift Für Naturforschung C

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In this study the enhancement effect of Sophora pachycarpa roots' acetone extract on the antibacterial activity of gentamycin was evaluated against Staphylococcus aureus. Disc diffusion and broth dilution methods were used to determine the antibacterial activity of gentamycin in the absence and presence of plant extract and its various fractions separated by TLC. A clinical isolate of S. aureus was used as test strain. The active component of the plant extract involved in enhancement of gentamycin's activity had R f = 0.72 on a TLC plate. The spectral data ( 1 H NMR, 13 C NMR) of this compound revealed that this compound was 5,7,2Ј,4Ј-tetrahydroxy-8-lavandulylflavanone (sophoraflavanone G), previously isolated from Sophora exigua. In the presence of 0.03 μg/ mL of sophoraflavanone G the MIC value of gentamycin for S. aureus decreased from 32 to 8 μg/mL (a fourfold decrease). These results signify that the ultra-low concentration of sophoraflavanone G potentiates the antimicrobial action of gentamycin suggesting a possible utilization of this compound in combination therapy against Staphylococcus aureus.

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Reduction of membrane fluidity by antibacterial sophoraflavanone G isolated from Sophora exigua

Cited by 185 publications

References 19 publications

Anti-Platelet and Membrane-Rigidifying Flavonoids in Brownish Scale of Onion

Anti-Platelet and Membrane-Rigidifying Flavonoids in Brownish Scale of Onion

Bioactive characterization of Persea americana Mill. by-products: A rich source of inherent antioxidants

Sophoraflavanone G from Sophora pachycarpa Enhanced the Antibacterial Activity of Gentamycin against Staphylococcus aureus

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