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Results for “RUTIN”

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At least 613 records · Page 34Linked to original sources

PubMed1999

Dietary flavonoids protect human colonocyte DNA from oxidative attack in vitro.

BACKGROUND & AIMS: Epidemiological studies suggest that antioxidant polyphenols in the human diet may protect against diseases such as cancer. In this study we investigated the cytoprotective potential of the flavonoids, quercetin, myricetin, kaempferol and rutin against oxidative DNA damage in human colonocytes in vitro. METHODS: Caco-2 cells, which display specialised enterocyte/colonocyte cell functions, were used as an in vitro model for human colonocytes. Hydrogen peroxide was employed as the oxidant. DNA damage (strand breakage, oxidised purines and oxidised pyrimidines) was determined using the alkaline single cell gel electrophoresis or comet assay. Cell growth and viability were measured. RESULTS: Hydrogen peroxide caused a dose-dependent increase in DNA strand breakage in human colonocytes, presumably via oxygen free radical generation. Quercetin and myricetin protected Caco-2 cells against oxidative attack. In addition, quercetin decreased hydrogen peroxide-mediated inhibition of growth. Neither rutin nor kaempferol was effective. However, quercetin, while inhibiting DNA strand breakage, did not alter the levels of oxidised bases following peroxide treatment. The antifungal agent ketoconazole, prevented quercetin cytoprotection in Caco-2 cells, indicating that P450-mediated metabolism may alter the efficacy of the flavonoids against oxidative DNA damage. CONCLUSION: Flavonoids, particularly quercetin, the most abundant flavonoid in the human diet, are likely to be important in defending human colonocytes from oxidative attack.

Cell Survival↗

PubMed1992

Oxygen radical-mediated mutagenic effect of asbestos on human lymphocytes: suppression by oxygen radical scavengers.

The mutagenic effect of chrysotile asbestos fibers and zeolite and latex particles on human lymphocytes in whole blood has been studied. It was concluded that their mutagenic activities were mediated by oxygen radicals because they were inhibited by antioxidant enzymes (SOD and catalase) and oxygen radical scavengers (rutin, ascorbic acid, and bemitil). It was proposed that oxygen radicals were released by phagocytes activated upon exposure to mineral dusts and fibers. The study of lucigenin- and luminol-amplified chemiluminescence of peritoneal macrophages stimulated by chrysotile fibers and zeolite and latex particles has shown that their mutagenic action is probably mediated by different oxygen species, namely, by the iron-oxygen complexes (perferryl ions) plus hydrogen peroxide, hydrogen peroxide, and superoxide ion, respectively. From the oxygen radical scavengers studied, rutin was the most effective inhibitor of the mutagenic effect of mineral fibers and dusts.

Animals↗

PubMed1994

Chemopreventive potential of dietary bioflavonoids against 20-methylcholanthrene-induced tumorigenesis.

The effect of dietary supplementation of flavonoidal compounds such as quercetin, rutin, luteolin and (+)-catechin on the incidence of fibrosarcoma induced by 20-methylcholanthrene (20-MC) in male Swiss albino mice was observed. Subcutaneous injection of 20-MC produced 100% tumor incidence and the onset of tumor appeared within 7 weeks, while flavonoid-treated mice (1% quercetin- and luteolin-mixed diets) produced tumors in the 9th week, and the tumor incidences in mice treated with quercetin- and luteolin-mixed diets were 52% and 60%, respectively. Subcutaneous administration of 20-MC along with the flavonoidal compounds (quercetin, luteolin) was found to have significant effect on tumor expression. The compounds rutin and (+)-catechin did not influence tumor expression in both experiments. Elevated levels of lipid peroxides, cytochrome P450 and decreased activity of glutathione-S-transferase (GST) were observed in the tumor bearing animals. Test-diet-treated animals showed reduction in the lipid peroxides and cytochrome P450, and increased activity of GST (P < 0.001). In vitro [3H]thymidine incorporation showed the inhibition of DNA synthesis in fibrosarcoma cells by the flavonoids. The possible mode of action of the flavonoidal compounds may be through their influence on the initiation and promotion phases of the carcinogenic process coupled with enhancement of the detoxification process.

Animals↗

PubMed1995

Inhibition of lung metastasis in mice induced by B16F10 melanoma cells by polyphenolic compounds.

Several polyphenolic compounds were tested for the inhibition of lung metastasis induced by B16F10 melanoma cells in mice. Oral administration of polyphenols such as curcumin and catechin at concentrations of 200 nmol/kg body weight were found to inhibit the lung metastasis maximally as seen by the reduction in the number of lung tumor nodules (80%). Other polyphenols which inhibited the lung tumor nodule formation were rutin (71.2%), epicatechin (61%), naringin (27.2%) and naringenin (26.1%). The polyphenols which did not inhibit lung tumor nodule formation were quercetin, morin and ellagic acid. Consequent to the inhibition of the lung tumor nodules, the life span of animals treated with polyphenols was also found to be increased. Curcumin (143.85%), catechin (80.81%) and rutin (63.59%) had maximal increase in life span. The results indicate a possible use of these compounds in arresting the metastatic growth of tumor cells.

Animals↗

PubMed2004

DNA hypomethylation induced by non-genotoxic carcinogens in mouse and rat colon.

The ability of non-genotoxic colon carcinogens to induce DNA hypomethylation was evaluated. Administering 0, 0.2 and 0.4 mg/kg of 5-aza-2'-deoxycytidine to female mice for 5 days resulted in a dose-related decrease in 5-methylcytosine in colon DNA. Rutin (3.0 mg/kg) and five bile acids (4.0 mg/kg) were administered in the diet to male F344 rats for 14 days. Rutin and four bile acids that promote colon cancer, deoxycholic acid, chenodeoxycholic acid, cholic acid and lithocholic acid caused DNA hypomethylation, while ursodeoxycholic acid that prevents colon cancer did not. Bromodichloromethane (BDCM) was administered to male F344 rats and B6C3F1 mice by gavage at 0, 50 and 100 mg/kg or in their drinking water at 0, 350 and 700 mg/l for up to 28 days. In rats, BDCM decreased DNA methylation, being more effective when administered by gavage, correlating to its greater carcinogenic potency by this route. In mice, BDCM did not decrease DNA methylation, corresponding to its lack of carcinogenic activity in the colon of this species. In summary, the ability of non-genotoxic colon carcinogens to cause DNA hypomethylation correlated with their carcinogenic activity in the colon.

Animals↗

PubMed2005

Relationship between vasodilation capacity and phenolic content of Spanish wines.

We aimed to determine: 1) the concentration of polyphenols in Spanish red wines, 2) the vasodilatory properties of those wines in relation with their polyphenol concentrations and 3) the vasodilation induced by some of these polyphenols in rat aortic rings. In the wines studied the concentration of rutin and kaempferol was high compared with other polyphenols. All wines relaxed precontracted rat aortic rings and this effect was directly related with the concentration of myricetin and kaempferol in the wines. Kaempferol and rutin also induced endothelium-dependent and independent relaxation, kaempferol was more potent. This relaxation was not inhibited by the estrogen receptor alpha antagonist ICI 182,760. Kaempferol also potentiated the endothelium-dependent relaxation induced by acetylcholine, which was reversed by Nw-nitro-l-arginine methyl ester (l-NAME). These findings show a good correlation between the concentration of polyphenols (especially kaempferol) of Spanish red wines and the vasodilatory effect, which may confer on them unique features in the prevention of cardiovascular disease.

Analysis of Variance↗

PubMed2005

In vitro basal and metabolism-mediated cytotoxicity of flavonoids.

The purpose of this study was to compare the basal cytotoxicity and metabolism-mediated cytotoxicity of kaempferol, quercetin and rutin. McCoy cells were exposed to various concentrations of the flavonols with and without the S9 system. The neutral red uptake assay was used to determine viability after 24 h at 35-37 degrees C. Dose-response curves were established for each flavonol in the presence and absence of external metabolizing systems. Kaempferol and quercetin were cytotoxic and provoked a dose-dependent decrease in cell viability, without the S9 system. The hepatic S9 microsomal fraction metabolized these compounds to less cytotoxic metabolites. In contrast, rutin at 500 microg/ml failed to produce any overt signs of toxicity in either assay.

Animals↗

PubMed2006

Total flavonoids quantification from O/W emulsion with extract of Brazilian plants.

A new derivative spectrophotometric (DS) method was proposed and validated for quantification of total flavonoids from in O/W emulsion with polyacrylamide (and) C13-14 isoparaffin (and) laureth-7 containing Catuaba (Trichilia catigua Adr. Juss) (and) Marapuama (Ptychopetalum olacoides Bentham) extract. DS method was optimized to perform the assay in most favorable conditions. Linearity, specificity and selectivity, recovery (Rc, %), precision (R.S.D., %), accuracy (E, %), detection (LOD, microg ml(-1)) and quantification limits (LOQ, microg ml(-1)) were established for method validation. First-derivative at 388.0 nm (zero-to-peak; amplitude= +/- 0.12; wavelength range= 300.0-450.0 nm and Deltalambda = 4 nm) offered linearity for rutin concentrations ranging from 10.0 to 60.0 microg ml(-1) in ethanol 99.5%. Second-derivative provided to be unsuitable for interval evaluation obtaining unacceptable accuracy. Analytical method was validated for first-derivative, according to the experimental results: correlation coefficient (r = 0.9999); specificity to total flavonoids quantification, expressed in rutin, at wavelength 388.0 nm and selectivity with elimination of interference from matrix; Rc = 108.78%; intra- and inter-run precision (1.30-3.65% and 3.48-4.68%), and intra- and inter-run accuracy (100.00-112.19% and 101.25-118.44%); LOD = 0.62 microg ml(-1) and LOQ = 1.86 microg ml(-1).

Brazil↗

PubMed2006

Quality evaluation of Platycladus orientalis (L.) Franco through simultaneous determination of four bioactive flavonoids by high-performance liquid chromatography.

Platycladus orientalis (L.) Franco (Cupressaceae), a traditional Chinese herb and food additive, has been used for treatments of gout, rheumatism, diarrhoea and chronic tracheitis. To evaluate the quality of P. orientalis (L.) Franco, a sensitive, simple and accurate reversed-phase high-performance liquid chromatographic (RP-HPLC) separation method with a photodiode array detector (DAD) was developed for the determination of four main bioactive flavonoids, rutin, quercitrin, quercetin and amentoflavone. Separation of the four compounds was achieved by the HPLC assay (Agilent Eclipse XDB-C 18 column with mobile phase, methanol-acetonitrile-18 mM sodium acetate buffer (pH 3.5) and recorded at UV 356 nm). This method showed good linear relation in the range of 0.8-80 microg/ml for rutin, 1.84-184 microg/ml for quercitrin, 0.72-72 microg/ml for quercetin and 0.72-72 microg/ml for amentoflavone. The correlation coefficients of the calibration curve for the analysis were all higher than 0.999. In addition, the contents of those four flavonoids in P. orientalis (L.) Franco growing in 12 different locations in China were compared to establish the effectiveness of the method.

Biflavonoids↗

PubMed2005

Identification of linear plasmid pAM1 in the flavonoid degrading strain Actinoplanes missouriensis(T) (DSM 43046).

By pulsed-field gel electrophoresis, a linear DNA element of about 100 kb was identified in Actinoplanes missouriensis(T) DSM 43046, which grows on the flavonoids hesperidin, rutin and quercetin, and which contains a CO forming quercetinase. Among six Actinoplanes species and strains tested, including A. globisporus(T) DSM 43857, A. philippinensis(T) DSM 43019, A. brasiliensis(T) DSM 43805, A. auranticolor(T) DSM 43031, and A. utahensis(T) DSM 43147, only the A. missouriensis strain exhibited such a genetic element. The linear plasmid, named pAM1, has proteins covalently attached to its 5'-ends like other linear replicons of actinomycetes. Attempts to cure pAM1 failed, however a mutant with reduced plasmid content was obtained, which showed reduced ability to degrade the flavonoid rutinosides rutin and hesperidin. Plasmid pAM1 is the first extrachromosomal genetic element identified in an Actinoplanes species and may be useful to develop genetic tools for biotechnologically important Actinoplanes strains.

Biodegradation, Environmental↗

PubMed2001

Inhibition of nitric oxide synthase expression by a methanolic extract of Crescentia alata and its derived flavonols.

In order to validate the use of Crescentia alata (Bignoniaceae) in the traditional medicine of Guatemala as an antiinflammatory remedy, the methanolic (MeOH) extract has been evaluated in vivo for antiinflammatory activity on carrageenin paw edema in rats and in vitro on Escherichia coli lipopolysaccharide- (LPS)-induced nitric oxide (NO) production and inducible nitric oxide synthase (iNOS) expression in J774.A1 macrophage cell line. This extract exerted in vivo a significant anti-inflammatory activity at the highest dose tested. The same extract showed in vitro an inhibitory activity on inducible nitric oxide synthase expression and on NO formation in LPS-primed J774.A1 cells. Subsequent fractionation and analysis of the extract has led to the isolation and characterization as major constituents of two flavonol glycosides: quercetin 3-O-alpha-L-rhamnopyranosyl-(1->6)-beta-D-glucopyranoside (rutin) 1, kaempferol 3-O-alpha-L-rhamnopyranosyl-(1->6)-beta-D-glucopyranoside (kaempferol 3-O-rutinoside) 2, and flavonol aglycone, kaempferol 3. Their structures were elucidated by spectral methods. The bioassay-directed analysis of flavonols 1-3 indicated that kaempferol (3) was the most active compound contained in the MeOH extract because it reduced in vitro both NO production and iNOS expression in LPS-primed J774.A1 cells, whereas rutin (1) and kaempferol 3-O-rutinoside (2) showed no significant activity. The MeOH extract and all of flavonoids tested did not show in vitro significant cytotoxic effect in J774.A1 macrophage cell line.

Animals↗

PubMed2003

Purification and characterization of a flavonol 3-O-beta-heterodisaccharidase from the dried herb of Fagopyrum esculentum Moench.

A flavonol-3-O-beta-heterodisaccharide glycosidase (FHG I) was isolated from dried aerial tissues of Fagopyrum esculentum Moench (Fagopyri herba). It has a specific enzyme activity of ca. 3.5 nkat mg(-1) protein in buffered extracts when rutin (quercetin-3-O-rutinoside) was used as substrate and an optimal enzyme activity was seen at around pH 4.8 and 30 degrees C. FHG I was purified about 156-fold to apparent homogeneity by hydrophobic interaction, anion exchange and size exclusion chromatographic steps. The apparent molecular mass of FHG I was 74.5+/-2 kDa as determined by SDS-PAGE and it is a monomeric glycoprotein with a carbohydrate content of 23%. The isoelectric point as determined by isoelectric focusing was 5.7 and the energy of activation was 32 kJ mol(-1). FHG I exhibits a high substrate specificity, preferring flavonol 3-O-glycosides comprising the disaccharide rutinose. The K(m) and V(max) values for the natural substrate rutin were calculated to be 0.561 microM and 745 nkat mg (-1) protein, respectively. Two oligopeptide fragments obtained after enzymatic digestion of FHG I were sequenced and showed similarities to sequences of beta-glucohydrolases from other plant species. Polyclonal antibodies were raised and their specificities determined. Another flavonol 3-O-beta-heterodisaccharide glycosidase (FHG II) could also be detected in buckwheat herb, having a molecular mass of 85.3+/-2 kDa and an isoelectric point between pH 6.0 and 6.5.

Amino Acid Sequence↗

PubMed2002

Mechanisms of flavonoid repair reactions with amino acid radicals in models of biological systems: a pulse radiolysis study in micelles and human serum albumin.

Neutral tryptophan (*Trp) and tyrosine (TyrO(*)) radicals are repaired by certain flavonoids in buffer, in micelles and in human serum albumin (HSA) with corresponding formation of semioxidized flavonoid radicals. In deaerated buffer, *Trp but not TyrO(*) radicals react with catechin. In micelles, quercetin and rutin repair both *Trp and TyrO(*) radicals. In addition to amino acid reactivity, microenvironmental factors and nature of the flavonoids govern this repair. Electron transfer efficiencies from quercetin to negatively charged *Trp radicals are 100% in the micellar pseudophases of positively charged cetyltrimethylammonium bromide, (CTAB), and neutral Triton X100 (TX100), but 55% in negatively charged sodium dodecyl sulfate (SDS). In oxygen-saturated CTAB micelles, quercetin also reacts with the superoxide radical anion. When bound to domain IIA of HSA, quercetin repairs, by intra- or intermolecular encounter, less than 20% of oxidative damage to HSA. Quercetin can also repair freely circulating oxidized molecules with repair efficiencies falling to 7% for oxidized *Trp, Tyr and alpha-MSH and to less than 2% for urate radical. This limited effectiveness is attributed both to the inaccessibility of bound quercetin and rutin toward radicals of circulating molecules and to the diffusion-controlled recombination of these radicals.

Catechin↗

PubMed2002

Mechanisms of flavonoid repair reactions with amino acid radicals in models of biological systems: a pulse radiolysis study in micelles and human serum albumin.

Neutral tryptophan (*Trp) and tyrosine (TyrO(*)) radicals are repaired by certain flavonoids in buffer, in micelles and in human serum albumin (HSA) with corresponding formation of semioxidized flavonoid radicals. In deaerated buffer, *Trp but not TyrO(*) radicals react with catechin. In micelles, quercetin and rutin repair both *Trp and TyrO(*) radicals. In addition to amino acid reactivity, microenvironmental factors and nature of the flavonoids govern this repair. Electron transfer efficiencies from quercetin to negatively charged *Trp radicals are 100% in the micellar pseudophases of positively charged cetyltrimethylammonium bromide, (CTAB), and neutral Triton X100 (TX100), but 55% in negatively charged sodium dodecyl sulfate (SDS). In oxygen-saturated CTAB micelles, quercetin also reacts with the superoxide radical anion. When bound to domain IIA of HSA, quercetin repairs, by intra- or intermolecular encounter, less than 20% of oxidative damage to HSA. Quercetin can also repair freely circulating oxidized molecules with repair efficiencies falling to 7% for oxidized Trp, Tyr and alpha-MSH and to less than 2% for urate radical. This limited effectiveness is attributed both to the inaccessibility of bound quercetin and rutin toward radicals of circulating molecules and to the diffusion-controlled recombination of these radicals.

Catechin↗

PubMed1997

Quercetin protects cutaneous tissue-associated cell types including sensory neurons from oxidative stress induced by glutathione depletion: cooperative effects of ascorbic acid.

Oxidation reactions are essential biological reactions necessary for the formation of high-energy compounds used to fuel metabolic processes, but can be injurious to cells when produced in excess. Cutaneous tissue is especially susceptible to damage mediated by reactive oxygen species and low-density lipoprotein oxidation, triggered by dysmetabolic diseases, inflammation, environmental factors, or aging. Here we have examined the ability of the flavonoid quercetin to protect cutaneous tissue-associated cell types from injury induced by oxidative stress, and possible cooperative effects of ascorbic acid. Human skin fibroblasts, keratinocytes, and endothelial cells were cultured in the presence of buthionine sulfoximine (BSO), an irreversible inhibitor of glutathione (GSH) synthesis. Depletion of intracellular levels of GSH leads to an accumulation of cellular peroxides and eventual cell death. Quercetin concentration-dependently (EC50: 30-40 microM) reduced oxidative injury of BSO to all cell types, and was also effective when first added after BSO washout. BSO caused marked decreases in the intracellular level of GSH, which remained depressed in quercetin-protected cells. Ascorbic acid, while by itself not cytoprotective synergized with quercetin, lowered the quercetin EC50 and prolonged the window for cytoprotection. The related flavonoids rutin and dihydroquercetin also decreased BSO-induced injury to dermal fibroblasts, albeit less efficaciously so than quercetin. The cytoprotective effect of rutin, but not that of dihydroquercetin, was enhanced in the presence of ascorbic acid. Further, quercetin rescued sensory ganglion neurons from death provoked by GSH depletion. Direct oxidative injury to this last cell type has not been previously demonstrated. The results show that flavonoids are broadly protective for cutaneous tissue-type cell populations subjected to a chronic intracellular form of oxidative stress. Quercetin in particular, paired with ascorbic acid, may be of therapeutic benefit in protecting neurovasculature structures in skin from oxidative damage.

3T3 Cells↗

PubMed1999

Urinary excretion of hydroxycinnamates and flavonoids after oral and intravenous administration.

The urinary recoveries of the hydroxycinnamates, ferulic acid (3-methoxy, 4-hydroxy cinnamic acid), and chlorogenic acid (the quinic acid ester of 3,4-dihydroxycinnamic acid), and three structurally related flavonoids were studied in the rat. For the latter, the aglycone quercetin was compared with its 3-glucoside (isoquercitrin) and 3-rhamnoglucoside (rutin). Doses of 50 mg/kg were administered via the oral and intravenous routes and urine collected over the subsequent 24-h period. Reverse phase HPLC with photo-diode array detection was used to analyze the unchanged compound and their metabolites excreted in the urine. Ferulic acid and isoquercitrin were orally absorbed (5.4 and 0.48% of administered dose, respectively) and are therefore bioavailable. In contrast, neither unchanged chlorogenic acid, rutin, quercetin, nor the conjugated metabolites in the form of glucuronide or sulphate were detected in the urine after oral dosing. All the flavonoids studied produced low total urinary recoveries after intravenous administration, 9.2% for quercetin-3-rhamnoglucoside, 6.7% for the 3-glucoside, and 2.4% for the aglycone, indicating that extensive metabolism to low molecular weight compounds or excretion via other routes may be occurring. Overall it can be stated that renal excretion is not a major pathway of elimination for intact flavonoids and hydroxycinnamates in the rat.

Administration, Oral↗

PubMed2003

Comparative study of flavonoids in experimental models of inflammation.

The anti-inflammatory activities of flavonols (quercetin, rutin and morin) and flavanones (hesperetin and hesperidin) were investigated in animal models of acute and chronic inflammation. Rutin was only effective in the chronic process, principally in adjuvant arthritis. On neurogenic inflammation induced by xylene, only the flavanones were effective; besides, these compounds were the most effective on subchronic process. The most important compound in reducing paw oedema induced by carrageenan was quercetin.

Animals↗

PubMed2002

Quercetin, but not its glycosides, is absorbed from the rat stomach.

Absorption and metabolism of quercetin, isoquercitrin (quercetin 3-O-glucose), and rutin (quercetin 3-O-glucose-rhamnose) were investigated in rats after in situ gastric administration (15 micromol/L) for 30 min. At the end of the experiment, 38% of the initial dose of quercetin had disappeared. Quercetin was rapidly absorbed by the stomach, and was recovered in the bile 20 min after infusion (4.07 +/- 0.10 micromol/L). The administration of rutin and isoquercitrin indicated that these glycosides were not hydrolyzed nor absorbed by this tissue. In conclusion, when flavonols are present in the diet as aglycons, they could be partly absorbed in the stomach, in contrast to their glycosidic forms which are not absorbed.

Absorption↗