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Flavonoids as reductants of ferryl hemoglobin

100%
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issue 3
509-513
EN
The ferryl derivatives of hemoglobin are products of the reactions of oxy- and methemoglobin with hydrogen peroxide. Ferryl hemoglobins, either with or without a radical site on the protein moiety, are oxidizing species. Plant polyphenols, flavonoids, have been shown to act as antioxidants in vivo and in vitro. Reactions of met- and oxyhemoglobin with hydrogen peroxide in the presence of catechin, quercetin and rutin were studied. These flavonoids accelerated reduction of ferryl hemoglobin to methemoglobin. The rate constants of the reactions of ferryl hemoglobin with catechin, quercetin and rutin were in the order of 102 M-1 s-1, i.e. similar to the rate constants of ferryl hemoglobin with intracellular reducing compounds like urate or ascorbate. The beneficial effect of flavonoids against oxidative damage of hemoglobin caused by hydroperoxides, reported in the literature, is probably, at least in part, connected with the ability of flavonoids to scavenge ferryl hemoglobin.
EN
Flavonoids exhibit prooxidant cytotoxicity in mammalian cells due to the formation of free radicals and oxidation products possessing quinone or quinomethide structure. However, it is unclear how the cytotoxicity of flavonoids depends on the ease of their single-electron oxidation in aqueous medium, i.e., the redox potential of the phenoxyl radical/phenol couple. We verified the previously calculated redox potentials for several flavonoids according to their rates of reduction of cytochrome c and ferricyanide, and proposed experimentally-based values of redox potentials for myricetin, fisetin, morin, kaempferol, galangin, and naringenin. We found that the cytotoxicity of flavonoids (n=10) in bovine leukemia virus-transformed lamb kidney fibroblasts (line FLK) and murine hepatoma (line MH-22a) increases with a decrease in their redox potential of the phenoxyl radical/phenol couple and an increase in their lipophilicity. Their cytotoxicity was decreased by antioxidants and inhibitors of cytochromes P-450, α-naphthoflavone and isoniazide, and increased by an inhibitor of catechol-O-methyltransferase, 3,5-dinitrocatechol. It shows that although the prooxidant action of flavonoids may be the main factor in their cytotoxicity, the hydroxylation and oxidative demethylation by cytochromes P-450 and O-methylation by catechol-O-methyltransferase can significantly modulate the cytotoxicity of the parent compounds.
EN
The aim of the studies was to establish relationships between flavonoids and elements important for human health. Therefore, total contents of flavonoids and phosphorus were determined by UV/Vis methods, flavonoids by HPLC, and Ca, Mg, Fe, Mn, Zn and Cu by FAAS in 68 infusions of medicinal herbs. Total flavonoids content in the aqueous extracts were in the range of 0.26 - 16.40 mg per 100 mL. The mean flavonoid contents (in mg per 100 mL of aqueous extract) were 2.24, 2.01, 1.83, 1.88 for rutin, myricetin, quercetin and kaempferol, respectively. The concentrations of Ca, Mg, P were determined in mg per 100 mL, and of Fe, Mn, Zn and Cu in μg per 100 mL. Total content of flavonoids was weakly correlated with quercetin (r = 0.41), kaempferol (r = 0.53), Cu (r = 0.43), and Ca (r = -0.30). Statistically significant correlations were also found among Cu, Ca, Mn, Zn and Fe. Cluster analysis grouped the studied herbs based on total flavonoids, also four flavonoids and essential elements contents, extracted from the whole population of herbs Sambuci flos, Betulae folium, and Sylibi mariani semen. Principal component analysis confirmed these findings and enabled identification of quercetin, kaempferol, Cu and Fe as the factors responsible for differentiation of the studied material.
EN
Thymus serpyllum L. (T.serpyllum) has a great interest as a potential plant component, which is used in the production of fermented milk products with anticancer effect. The plant material was collected at the flowering stage. Chemical composition of essential oil and flavonoids from the aerial parts of the T. serpyllum, grown in the Southern Altai of the East Kazakhstan region, has been investigated for the first time. Output of the essential oil received from the aerial part of the plant in the flowering stage was on average 0,2%. Forty-one compounds were identified in T. serpyllum essential oil, which accounts for 96, 1% of the total oil. The main components of the oil were thymol (41,8%), γ-terpinene (15,3%), o-cymene (10,9%). Apart from the composition of essential oils, there were shown some flavonoids, such asapigenin 7 glucoside (0.24 % of dried plant material), luteolin (0,039 %), quercetin (0,006 %), which demonstrated a cytotoxic effect on cancer cells. In our experiments, luteolin had greater cytotoxic effect on cancer cells HCT-15 than quercetin. IC50 value of quercetin (100 μM) was higher than that of luteolin (50 μM).
EN
SSixteen ethanolic extracts were obtained from seven different bee bread samples. The total flavonoid content in the extracts was determined by aluminium-chloride method and was in the range of 8.3 mg/L±6.24% to 195.3 mg/L±1.35% and 28.8 mg/L±19.33% to 603.3 mg/L±4.64% with reference to quercetin and rutin, respectively. The relative standard deviations (RSD) for parallel measurements for the calibration curves of quercetin dehydrate and rutin trihydrate were in the range of 0.51% to 9.39% and 5.02% to 19.91%, respectively. The RSD for parallel measurements for the extracts with reference to quercetin dihydrate and rutin trihydrate were in the range of 0.23% to 11.64% and 4.64% 19.33%, respectively. The total flavonoid content mainly depended on a ratio of bee bread to 50% ethanol and technology of obtaining bee bread. The significant differences between results were statistically confirmed. The best antibacterial activity of bee bread extracts was found against Bacillus cereus CCM 2010, Clostridium perfringens CCM 4435, and Staphylococcus aureus subsp. aureus CCM 4223. The activity of the bee bread extracts against Gram negative bacteria, Aspergillus and Penicillium genera was lower with moderate anticandidal activity. The obtained results indicated that it was very important to employ extracts with a high content of bee bread in 50% ethanol (1:5, 1:10). According to the results of this study, bee bread is a product which is rich in flavonoids and with good antibacterial activity against Gram positive bacteria and can be considered as a raw material for development of diet supplements and antimicrobial medicinal products
EN
A magistral preparation based on the sage leaf decoction or infusion is one of the most popular herbal prescription prepared in pharmacies in Lower Silesia (Poland) for gargling in the pharyngitis or mouth infections. Other components of this preparation are boric acid, aluminum(III) acetotartrate or Burow's solution, and glycerol. The study aimed to investigate the polyphenolic composition and relations between herbal and chemical ingredients that are present in this mixture in comparison with the traditional aqueous galenic forms – infusion and decoction. The analysis was performed using HPLC-DAD and ESI-MS methods. The main polyphenolic ingredients of sage leaf were rosmarinic acid and luteolin 7-O-β-glucuronide. The content of analyzed polyphenols was higher in the decoction than in the infusion. The pharmacological activity of the examined mixture results from the presence of boric acid, aluminum(III) salts and polyphenolic components of sage leaf. The study showed that in the presence of excess salts of aluminum(III) and boric acid, sage polyphenols are partially soluble in an aqueous medium (mainly phenolic acids) and complexed as precipitated sediment (especially flavonoids). The aqueous solutions of this preparation are cloudy, which suggests limited solubility of the formed complexes. Therefore, the therapeutic activity of the sage leaf magistral preparation should be associated with the presence of water soluble caffeic acid esters like rosmarinic acid. The influence of luteolin glycosides coordination complexes is not evident. The obtained results also confirm the stability of the examined formula in the conditions of cold storage (4-6 °C) within 7 days from its production.
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2017
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vol. 64
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issue 2
265-271
EN
The aim of this study was to evaluate the bioactivity of flavonoids extracted from sweet-cherry stems which are often used by a traditional system of medicine to treat gastro-intestinal and urinary tract infections but lacking any consistent scientific evidence; moreover the information about the class of phenolics, their content and the potential bioactivity of such material is very scarce. Thus, in this context, we have set a research study in which we evaluated the profile and content of phenolics extracted from sweet-cherry stems through a conventional (70ºC and 20 min) and ultrasound assisted extraction (40 kHz, room temperature and 20 min). The extracts were phytochemically characterized by using an HPLC-DAD-UV/VIS system and assayed by an in vitro minimum inhibitory concentration (MIC) bioassay against Escherichia coli isolates. Simultaneously, the total antioxidant activities were measured using the 2,2'-azinobis-3-ethylbenzothiazoline-6-sulphonate (ABTS•+) radical cation assay. Our results indicate that sweet-cherry stems have a high content of sakuranetin, ferulic acid, p-coumaric acid, p-coumaroylquinic acid, chlorogenic acid and its isomer neochlorogenic acid. Their average levels were highly affected by the extraction method used (p<0.001). The same trend was observed for total antioxidant activity and MIC values. The extracts produced with ultrasounds presented both, a higher total antioxidant activity and a lower minimum inhibitory concentration. Statistical analyses of our results showed a significant correlation (p<0.01) of total antioxidant activity and minimum inhibitory concentration with phenolics present in the extracts studied. Thus, we can conclude that cherry stems can be further exploited to purify compounds and produce coproducts with enhanced biologically added value for pharmaceutical industry.
EN
Bioactive polyphenolics are ubiquitously present in plants and may play an important role in the prevention and management of certain human diseases. Three known flavonoids viz Kaemperol-3-O-rutinoside (1), quercetin-3-O-glucoside (2) and kaemperol-3-O-glucoside (3) and inseparable mixture (1:1) of quercetin-3-O-glucose/galactose (4) were isolated, and identified for the first time from Holarrhena floribunda. The antioxidant capacity using the ORAC, FRAP and TEAC assays and inhibition of lipid peroxidation were measured for isolated flavonoids. The result showed that compounds 2 and 4 showed significantly increased ORAC, TEAC, and FRAP activities with low pro-oxidant potential as well as improved lipid peroxidation inhibition levels when compared to compounds 1 and 3. The most active compounds were found to be flavonoids with a quercetin basic structure. These results imply that the isolated flavonoid glycosides are responsible for the antioxidant activity of the plant leaves and it forms the scientific basis for its traditional usage.
EN
The chemical investigation of the chloroform and ethyl acetate extracts of the aerial parts of Forsskaolea viridis Ehrenb. ex Webb (Family: Urticaceae) led to isolation eight compounds for the first time from this plant, while two phenolic compounds, identified as p-coumaric and caffeic acids as well as six flavonoid compounds identified as 5-hydroxy-6,7,3',4'-tetramethoxy flavone, chrysoeriol, acacetin, chrysoeriol-7-O-β-D-glucoside, kaempferol-3-O-(2"-O-E--p-coumaroyl)-β-D-glucoside and isovetixin. The chemical structure of the isolated compounds was established by spectroscopic methods including UV, MS, 1H-NMR, and 13C-NMR. Antimicrobial, antioxidant and cytotoxic activities of the ethyl acetate and chloroform extracts were evaluated. The ethyl acetate extract exhibited strong antimicrobial activity (12-30 mm) against the tested strains. The ethyl acetate and chloroform extracts showed fair antioxidant and cytotoxicity.
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2015
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vol. 62
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issue 3
547-552
EN
Kaempferide (3,5,7-trihydroxy-4'-methoxyflavone, 1), a naturally occurring flavonoid with potent anticancer activity in a number of human tumour cell lines, was first semisynthesized from naringin. Based on Mannich reaction of kaempferide with various secondary amines and formaldehyde, nine novel kaempferide Mannich base derivatives 2-10 were synthesized. The aminomethylation occurred preferentially in the position at C-6 and C-8 of the A-ring of kaempferide. All the synthetic compounds were tested for antiproliferative activity against three human cancer cell lines (Hela, HCC1954, SK-OV-3) by the standard MTT method. The results showed that compounds 1, 2 and 5-10 were more potent against Hela cells with IC50 values of 12.47-28.24 μM than the positive control cis-platin (IC50 41.25 μM), compounds 5, 6, 8 and 10 were more potent against HCC1954 cells with IC50 values of 8.82-14.97 μM than the positive control cis-platin (IC50 29.68 μM), and compounds 2, 3, 5, 6 and 10 were more potent against SK-OV-3 cells with IC50 values of 7.67-18.50 μM than the positive control cis-platin (IC50 21.27 μM).
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2015
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vol. 62
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issue 2
207-213
EN
Quercetin, a member of the flavonoid family is a major antioxidant acquired in humans by food consumption, while Cadmium fluoride (CdF2) is one of the naturally occurring chemicals having adverse effects. The protective effect of quercetin on time dependent oxidative damage induced in mice liver by CdF2 was studied in the following groups of mice consisting of six mice each: (i) control group; (ii) mice treated with single i.p injection of 2 mg/kg bw CdF2 for 24 h; (iii) mice treated with single i.p injection of 2 mg/kg bw CdF2 for 48 h; (iv) mice treated with single i.p injection of quercetin (100 mg/kg bw); (v) mice treated with i.p injection of 100 mg/kg bw of quercetin followed by i.p injection of CdF2 (2 mg/kg bw) for 24 h; and (vi) mice treated with i.p injection of 100mg/kg bw of quercetin followed by CdF2 (2 mg/kg bw) for 48 h. Administration of quercetin two hours before CdF2 significantly reduced the biochemical alterations in reduced glutathione, ascorbic acid, lipid peroxidation, super oxide dismutase, catalase and total protein (p<0.05). Histopathology also showed the protective effect of quercetin. The livers treated with CdF2 were atrophic, markedly nodular, inflamed and necrotic. However, this effect was reduced to a minimum in the mice pre-treated for two hours with quercetin.
EN
Two natural flavonoids, quercetin and isorhamnetin 3-O-acylglucosides, were examined for their inhibitory influence on the in vitro production and release of reactive oxygen species in polymorphonuclear neutrophils (PMNs). The generation of superoxide radical, hydrogen peroxide and hypochlorous acid were measured by, respectively, cytochrome c reduction, dichlorofluorescin oxidation and taurine chlorination. Membrane lipid oxidation was studied by the thiobarbituric acid method in mouse spleen microsomes. The addition of flavonoids at the concentration range 1-100 μM inhibited PMNs oxidative metabolism and lipid peroxidation in a dose-dependent manner. The results suggest that these flavonoids suppress the oxidative burst of PMNs and protect membranes against lipid peroxidation.
EN
Talipariti elatum (Sw.) Malvaceae, also known as Blue Mahoe or Mountain Mahoe, commonly named as Majagua azul or Majagua, with red or crimson flowers, is a medicinal tree traditionally used against cough, asthma, catarrh, and expectorant. Its flowers contain a lot different chemical compounds, mainly flavonoids. From red petals of the flowers a flavonol glucoside was isolated and characterized by TLC, UV, IR, HPLC-MS/MS and NMR spectroscopy. Structure analyses of that chemical component revealed that It have the identical glucoside moiety attached to a flavonol skeleton like gossypitrin (gossypetin-7-O--glucoside) but in different position for which the structure of gossypetin-3’-O-glucoside was deduced from HSQC, HMBC, COSY and NOESY correlations.
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2011
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vol. 58
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issue 4
433-448
EN
Multidrug resistance (MDR) of cancer cells poses a serious obstacle to successful chemotherapy. The overexpression of multispecific ATP-binding cassette transporters appears to be the main mechanism of MDR. A search for MDR-reversing agents able to sensitize resistant cells to chemotherapy is ongoing in the hope of their possible clinical use. Studies of MDR modulators, although they have not produced clinically beneficial effects yet, may greatly enrich our knowledge about MDR transporters, their specificity and mechanism of action, especially substrate and/or inhibitor recognition. In the present review, interactions of three groups of modulators: phenothiazines, flavonoids and stilbenes with both P-glycoprotein and MRP1 are discussed. Each group of compounds is likely to interact with the MDR transporters by a different mechanism. Phenothiazines probably interact with drug binding sites, but they also could indirectly affect the transporter's activity by perturbing lipid bilayers. Flavonoids mainly interact with ABC proteins within their nucleotide-binding domains, though the more hydrophobic flavonoids may bind to regions within transmembrane domains. The possible mechanism of MDR reversal by stilbenes may result from their direct interaction with the transporter (possibly within substrate recognition sites) but some indirect effects such as stilbene-induced changes in gene expression pattern and in apoptotic pathways should also be considered. Literature data as well as some of our recent results are discussed. Special emphasis is put on cases when the interactions of a given compound with both P-glycoprotein and MRP1 have been studied simultaneously.
18
75%
EN
Introduction. Flavonoids are a large group of natural compounds that have been considered to be beneficial in ameliorating some age-dependent disorders. However, a potential use of these compounds in epilepsy treatment has not been systematically reviewed. Aim. This review describes the pharmacological activity of some polyphenols (flavonoids) in different animal models of seizures e.g. pentylenetetrazole-induced seizures, kainate-induced seizures and pentylenetetrazole kindling in rats. Method and Discussion. A literature review was conducted using PubMed from 1963 to October 2013 relating effects of flavonoids on experimentally-induced seizures in rodents. Articles chosen for references were queried with the following prompts: “flavonoids and epilepsy”, “flavonoids and seizures”, “plant polyphenols and epilepsy”, and “plant polyphenols and seizures”. Out of 84 reports 32 pharmacological studies with chemically well-defined flavonoids and using widely accepted animal models of seizures have been taken into account in this review. No clinical data on the antiepileptic effect of flavonoids have been reported so far. Conclusion. The reviewed data suggest the possible benefits of some chemically well-defined polyphenolic compounds of plant origin in antiepileptic treatment. Among flavonoids, resveratrol, baicalein, quercetin and rutin showed significant antiseizure activity. The ability of flavonoids to prevent brain excitability and to protect the brain against oxidative stress-induced damage suggests a potential use of some flavonoids at least as adjunctive therapy for the treatment of epilepsy.
PL
Ziołolecznictwo stanowi jedną z głównych gałęzi tradycyjnej medycyny chińskiej (traditional Chinese medicine – TCM). W pracy skupiono się na aktywności biologicznej wybranych flawonoidów, a także konkretnych przykładach wpływu tych substancji na różne układy organizmu. Flawonoidy to grupa związków chemicznych zawartych w surowcach roślinnych, miodzie, propolisie czy grzybach stosowanych w TCM. Chryzyna, galangina, kemferol i fisetyna to przykłady flawonoidów wykazujących m.in. właściwości przeciwutleniające, przeciwzapalne czy przeciwbakteryjne. Właściwości te są przedmiotem wielu badań naukowych, mających na celu zbadanie ich potencjalnego działania terapeutycznego.
EN
One of the branches of traditional Chinese medicine (TCM) is herbal medicine. In this paper, we focus on the biological activity of substances belonging to flavonoids and specific examples of their impact on various body systems. Flavonoids are a group of chemical compounds included in plant materials, honey, propolis or mushrooms used in TCM. Chrysin, galangin, kaempferol and fisetin are examples of flavonoids showing, among others, antioxidant, anti-inflammatory or antibacterial properties, which are the subject of various scientific studies aimed at examining their potential therapeutic effect.
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