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PubMed2000

Synergistic action of rutin and orthovanadate on nitric oxide release from mouse macrophage cells.

The cooperative action of sodium orthovanadate (a putative protein-phosphotyrosine phosphatase inhibitor) and rutin (an effective superoxide scavenger) on the nitric oxide (NO) production of J774A.1 mouse macrophage cells has been investigated. Orthovanadate alone caused a mild but significant increase in NO production of the cells at its highest concentration used (500 microM). Orthovanadate and rutin together caused a significant increase in the nitrite level of the supematants of the J774A.1 cells after a 24-hour incubation period, in a concentration dependent manner. The optimal doses for orthovanadate and rutin were 50 microM and 100 microM, respectively. This cooperative action of rutin and orthovanadate was totally inhibitable by catalase, reduced glutathion, N-acetylcystein, cycloheximide, pyrrolidine dithiocarbamate (a putative NF-kappaB inhibitor), genistein and tyrphostin-AG126 (two protein tyrosine-kinase inhibitors). Superoxide dismutase had no inhibitory effect. Orthovanadate and rutin (only together) could induce the oxidation of 2',7'-dichlorofluorescein-diacetate, a marker of hydrogen peroxide. This effect was inhibitable by reduced glutathion, a hydrogen peroxide specific scavenger. These findings suggest, that orthovanadate can induce the production of NO by J774A.1 macrophages not only by inhibition of protein tyrosine-phosphatases, but, using it with rutin, by increasing the level of hydrogen peroxide in the cells.

Animals↗
PubMed2002

Different action of IBMX, isoproterenol and rutin on orthovanadate-induced nitric oxide release in mouse macrophage cells.

The effects of cAMP-elevating compounds IBMX (3-isobutyl-1-methylxanthine) and isoproterenol, and that of rutin (an effective superoxide scavenger) were studied on orthovanadate--(a putative protein-phosphotyrosine phosphatase inhibitor) induced nitric oxide (NO) production in J774A.1 mouse macrophage cells. As we previously reported (Koncz and Horváth, 2000), rutin and sodium orthovanadate act synergistically to induce production of high amount of NO in J774A.1 cells. IBMX, an agent that can elevate cAMP level in the cells, can reduce the production of both the LPS- and rutin + orthovanadate-induced NO in macrophages. In contrast, isoproterenol, a non-selective beta-adrenergic receptor agonist, that reduced the LPS-induced NO production in macrophage cells, was unable to reduce the rutin + orthovanadate-induced NO production without negatively affecting cell viability. Moreover, isoproterenol dramatically enhanced the orthovanadate-induced NO synthesis in J774A.1 cells. Our previous study clarified that rutin and orthovanadate, in a specific concentration ratio of both, were able to produce hydrogen peroxide (H2O2). Using 2',7'-dichlorofluorescein-diacetate as a marker for H2O2, isoproterenol alone induced its oxidation but the rutin plus orthovanadate-induced H2O2 production was reduced by isoproterenol. These observations have revealed that, in some cases, H2O2 and superoxide (O2-) scavengers can act in a reverse mode on macrophage cells depending on the presence or absence of orthovanadate.

1-Methyl-3-isobutylxanthine↗
PubMed1998

[Study of the inclusion compound of rutin with beta-cyclodextrin].

In order to improve the solubility of Rutin in aqueous solution and the stability, the inclusion compound of Rutin with beta-CD was manufacted by saturated aqueous solution method. The formation of the inclusion compound was confirmed by IR spectroscopy and differential scauning calorimetry. The content of Rutin in inclusion compound was determined by UV. The results indicated that the inclusion compound of Rutin with beta-CD was formed. Quantitative analysis demmonstrated that the molecular ratio of Rutin to beta-CD in the complex was 1:1 with the inclusion constant of 283.79 L/mol at 30 degrees C. The dissolubility of Rutin in water has added to 643.19 mg/L (20 degrees C).

Biological Availability↗
PubMed2000

[Real time monitor of rutin stability during heating by Fourier transform infrared spectroscopy].

The thermal stability of the natural product of rutin was studied by Fourier Transform Infrared Spectroscopy (FTIR) in this paper for the first time. To monitor the changing of rutin in real time, the temperature-control accessory was also used to in-situ follow the thermal behavior. It is demonstrated that as the temperature increased from 25 degrees C to 270 degrees C, the thermally-induced denaturation of rutin was accompanied by the oxidation and thermal discomposed procedure. The structure of rutin changed at a lower temperature (75 degrees C). This is not only indicating the existence of an intermediate state, but also approved that the stability of rutin is poor. While at the higher temperature (270 degrees C), rutin discomposed into two results. It is proved that this method is fast, accurate and having no solvent effect. Samples can thus be examined undestroyed.

Computer Systems↗
PubMed1998

The influence of rutin on the weight, metastasis and melanin content of B16 melanotic melanoma in C57BL/6 mice.

The influence of rutin on the growth rate and tumor weight of B16 melanoma as well as melanin content and ultrastructure of melanoma cells and metastasis formation was studied in mice. All mice were injected s.c. into the left flank with 0.2 ml of suspension containing 10(6) B16 melanoma cells. The experimental groups were treated with a solution of rutin i.p. every two days with total doses of 1, 5 or 10 mg/mouse. The rutin was dissolved in DMSO. The control groups of mice were injected with 0.2 ml 0.9% NaCl and 0.2 ml DMSO. Increasing doses of rutin 1, 5 or 10 mg per mouse caused augmentation of the tumor mass to 2400 mg, 2600 mg and 2800 mg respectively, whereas the tumor weight of the control group was 980 mg. The median number of lung metastases in the control groups was 12; after treatment with 5 or 10 mg of rutin, the number of lung colonies increased to 19 and 27, respectively. The administration of 10 mg rutin inhibited melanin formation by about 43%. The melanosomes in the experimental groups were in the 2nd or 3rd stage, and the low content of melanin was noticed.

Animals↗
PubMedDate not supplied

Kinetic spectrophotometric determination of rutin by its inhibitory effect on the oxidation of amaranth by potassium periodate.

A novel kinetic spectrophotometric method is described for the determination of rutin. The method is based on the inhibitory effect of rutin on the oxidation reaction of amaranth by potassium periodate in acidic media at 100 degrees C. The linear range for the determination of rutin is 0.02 - 0.50 microg/ml, and the detection limit is 0.014 microg/ml. The method has been successfully applied to the determination of rutin in medicine of rutin tablet and traditional Chinese medicine.

Amaranth Dye↗
PubMed1977

Effect of lysine and diethanolamine-rutin on blood levels, withdrawal reaction, and acute toxicity of ethanol in mice.

The effects of L-Lysine and diethanolamine-rutin on blood ethanol levels and withdrawal convulsions following a 4-day exposure to ethanol vapors were evaluated in 30-40-g male Swiss-Webster mice. The animals were exposed in groups, along with simultaneous controls, in a 34-liter dynamic Plexiglas exposure chamber. Blood was collected by retro-orbital puncture and analyzed enzymatically for ethanol. At the end of the inhalation period, convulsions on handling were scored over 24 hr. In addition, the effects of L-Lysine and diethanolamine-rutin on blood ethanol levels and on acute ethanol toxicity following oral and intraperitoneal administration were evaluated. L-Lysine lowered blood ethanol levels following inhalation or oral administration of ethanol. Diethanolamine-rutin had no effect on blood ethanol levels. Both L-Lysine and diethanolamine-rutin decreased the withdrawal reaction in dependent mice. L-Lysine increased the oral LD50 of ethanol, while diethanolamine-rutin decreased the intraperitoneal LD50 of ethanol.

Animals↗
PubMed2005

Modulation of osteoclastogenesis in porcine bone marrow cultures by quercetin and rutin.

Flavonols, in contrast to soybean isoflavones, are the most abundant phytoestrogens in western diets, being present in onions, beans, fruits, red wine, and tea. They may protect against atherosclerosis, inhibit certain cancer cell types, and reduce bone resorption. The most widely distributed flavonol is quercetin, which occurs mainly as its glycoside, rutin, but data are very scarce regarding the precise mechanism of action of these compounds on bone-resorbing cells at concentrations similar to those detected in human plasma. We have therefore investigated the effects of nanomolar concentrations of quercetin and rutin on the development and activity of osteoclasts in vitro compared with the effects of 17beta-estradiol. Nonadherent porcine bone marrow cells were cultured on dentine slices in the presence of 10 nM 1,25-dihydroxyvitamin D3 (1,25(OH)2D3), with or without 10 nM quercetin, 10 nM rutin or 10 nM 17beta-estradiol for 11 days. Multinuclear TRAP+ cells that resorbed dentine (osteoclasts) developed in the presence of 1,25(OH)2D3, but their number was significantly reduced by quercetin, rutin, and 17beta-estradiol (P < 0.05). Like 17beta-estradiol, both flavonols also significantly reduced resorption (P<0.05) as assessed by the size of pits resorbed on dentine slices. Osteoclasts and osteoclast progenitors contained estrogen receptor alpha (ERalpha), ERbeta, and RANK proteins. Both flavonols increased nuclear ERbeta protein and decreased ERalpha protein of osteoclast progenitors. Moreover, rutin reduced RANK protein, whereas 17beta-oestradiol and quercetin promoted apoptosis by cleavage of caspase-8 and caspase-3. All the effects of flavonols were reversed by 1 microM ICI 182,780, an estrogen antagonist. Thus, the anti-resorbing properties of flavonols are mainly mediated by ER proteins through the inhibition of RANK protein or the activation of caspases.

Animals↗
PubMed2006

Rutin improves the antioxidant status in streptozotocin-induced diabetic rat tissues.

Rutin, a polyphenolic flavonoid, was investigated for its antioxidant potential in streptozotocin (STZ)-induced diabetic rats. Rats were rendered diabetic by a single intraperitoneal injection of streptozotocin (50 mg/kg). The levels of fasting plasma glucose and insulin were estimated. Lipid peroxidative products and antioxidants were estimated in liver, kidney and brain. Histopathological studies were carried out in these tissues. A significant (p < 0.05) increase in the levels of fasting plasma glucose, lipid peroxidative products (thiobarbituric acid reactive substances [TBARS] and lipid hydroperoxides [HP]) and a significant (p < 0.05) decrease in plasma insulin, enzymic antioxidants (superoxide dismutase [SOD], catalase, glutathione peroxidase [GPx] and glutathione reductase [GRx]) and nonenzymic antioxidants (reduced glutathione [GSH], vitamin C and E) in diabetic liver, kidney and brain were observed. Oral administration of rutin (100 mg/kg) for a period of 45 days significantly (p < 0.05) decreased fasting plasma glucose, increased insulin levels and improved the antioxidant status of diabetic rats by decreasing lipid peroxidative products and increasing enzymic and nonenzymic antioxidants. Normal rats treated with rutin (100 mg/kg) showed no significant (p < 0.05) effect on any of the parameters studied. Histopathological studies of the liver, kidney and brain showed the protective role of rutin. Thus, our study clearly shows that rutin has antioxidant effect in STZ-induced experimental diabetes.

Animals↗
PubMed1989

Chelating and free radical scavenging mechanisms of inhibitory action of rutin and quercetin in lipid peroxidation.

Inhibitory effects of flavonoids rutin and quercetin on ferrous ion-dependent lipid peroxidation of lecithin liposomes and NADPH- and CCl4-dependent lipid peroxidation in rat liver microsomes were studied to elucidate the chelating and free radical scavenging activities of these compounds. The interaction of rutin with superoxide ion and ferrous ions and the reaction of quercetin with lipid peroxy radicals were also studied. Both flavonoids were significantly more effective inhibitors of iron ion-dependent lipid peroxidation systems due to chelating iron ions with the formation of inert iron complexes unable to initiate lipid peroxidation. At the same time, iron complexes of flavonoids retained their free radical scavenging activities. The chelating mechanism of inhibition was more important for rutin than for quercetin. The mutual effect of rutin and ascorbic acid on non-enzymatic lipid peroxidation was also studied. It was concluded that rutin and quercetin are able to suppress free radical processes at three stages: the formation of superoxide ion, the generation of hydroxyl (or cryptohydroxyl) radicals in the Fenton reaction and the formation of lipid peroxy radicals.

Aminopyrine N-Demethylase↗
PubMed1994

Prevention by rutin of gastric lesions induced by ethanol in rats: role of endogenous prostaglandins.

1. This study was designed to demonstrate the cytoprotective effect of Rutin against ethanol-induced gastric injury in rats and to determine whether this cytoprotective effect is mediated by endogenous prostaglandins. 100 and 200 mg/kg of Rutin given orally 1 hr before administration of 1 ml of 100% ethanol significantly (p < 0.01) reduced the area of macroscopic lesions induced by ethanol (84.16 +/- 23.01 and 54.75 +/- 16.05 respectively) when compared to distilled water (305.60 +/- 67.20). However, it did not induce changes in the amount and total proteins and hexosamines content of gastric mucus. 2. Pretreatment with indomethacin, 10 mg/kg s.c. 30 min before Rutin administration, slightly but not significantly reduced the cytoprotective effect. 3. The levels of PGE2 present in the mucous material were not significantly modified with administration of Rutin (100 mg/kg). 4. These results show that Rutin has a cytoprotective effect against ethanol injury in the rat, but this property does not appear to be mediated by endogenous prostaglandins.

Animals↗
PubMed2005

Optimal recovery of high-purity rutin crystals from the whole plant of Fagopyrum esculentum Moench (buckwheat) by extraction, fractionation, and recrystallization.

Rutin, one of the flavonoids derived from plants, is increasingly in demand in the food, pharmaceutical, and cosmetic industries due to its various biological and physiological activities including antioxidation, anti-inflammation, and anti-hypertension. The whole plant of buckwheat (Fagopyrum esculentum Moench) is a major source of natural rutin. This study developed a low-cost process encompassing the efficient extraction, fractionation, and recrystallization to obtain high-purity rutin from buckwheat, and it could improve the economic utilization of this abundant low-value agricultural product. The sequential separation and purification procedures established in this study involved extraction with 50% (v/v) aqueous ethanol at 80 degrees C for 1 h followed by elution with water and aqueous ethanols at 20% and 30% (v/v) on a styrene-based resin column, and recrystallization at 4 degrees C for 12 h. These conditions resulted in the recovery of 92% of total rutin with over 95% purity. In the present study, high-purity rutin was obtained from whole buckwheat through low-cost processes, the separation and purification strategy established in this study could provide valuable information to the relevant industries.

Chemical Fractionation↗
PubMed2004

Separation of rutin nona(H-) and deca(H-) sulfonate sodium by ion-pairing reversed-phase liquid chromatography.

Ion-pairing reversed-phase liquid chromatography (RPLC) was used to separate two polysulfonates, rutin nona(H-) sulfonate sodium and rutin deca(H-) sulfonate sodium, which have very similar chemical structures. The final product always contained both of them when one of the compounds was synthesized. Baseline separation was achieved on a C8-bonded silica column at ambient temperature. The eluent was acetonitrile-15 mM phosphate buffer solution containing 20 mM TBA (pH 6.0) (46:54, v/v). The calibration plot was linear in the concentration range 0.5-200 microg ml(-1) for both analytes. The limits of detection (LODs; 254 nm) were 0.03 microg ml(1-) for rutin nona(H-) sulfonate sodium and 0.04 microg ml(-1) for rutin deca(H-) sulfonate sodium. Three batches of rutin deca(H-) sulfonate sodium were analyzed using the assay; the results showed that the analytical performance is really satisfactory.

Chromatography, Liquid↗
PubMed2006

Development of a biosensor based on gilo peroxidase immobilized on chitosan chemically crosslinked with epichlorohydrin for determination of rutin.

A new reagentless biosensor for the square-wave voltammetric determination of rutin in pharmaceutical formulations was developed by immobilization of gilo (Solanum gilo) crude extract in chitosan matrix. The gilo tissue acts as a source of peroxidase. The highest biosensor performance was obtained after immobilization of the peroxidase in chemically crosslinked chitosan with epichlorohydrin and glutaraldehyde that was incorporated in a carbon paste electrode. In the presence of hydrogen peroxide this enzyme catalyses the oxidation of rutin to quinone and the electrochemical reduction of the product was obtained at a fixed potential of +124 mV versus Ag/AgCl (3.0 M KCl). The performance and factors influencing the resulting biosensor were studied in detail. The bioelectrode exhibited a linear response for rutin concentrations from 3.4x10(-7) to 7.2x10(-6) M (r=0.9998) and the recovery of rutin from the samples ranged from 96.2 to 102.4%. The detection and quantification limits were 2.0x10(-8) and 6.3x10(-8) M, respectively. The relative standard deviation was less than 1.0% for solutions containing 3.4x10(-7) to 7.2x10(-6) M rutin in 0.1 M phosphate buffer solution at pH 7.0 (n=10). The lifetime of this biosensor was 8 months (at least 500 determinations).

Benzoquinones↗
PubMed2004

The modulating effects of quercetin and rutin on the mitomycin C induced DNA damage.

The present study was carried out to investigate the modulating effects of the two flavonoids quercetin and rutin on the mutagenic anticancer drug mitomycin C by single cell gel electrophoresis (Comet assay) in human lymphocytes. Lymphocytes were incubated with different concentrations of quercetin and rutin, with or without mitomycin C, and DNA damage was evaluated. Concentrations of 0.03, 0.15, 0.3, 0.6, 1.5 and 3mM quercetin significantly reduced the DNA strand breakage induced by mitomycin C (P<0.001) but the highest concentration of 6mM quercetin did not show a protective effect. The frequency of damaged cells induced by mitomycin C was not changed at 0.02 mM, and also at the highest concentrations of 1.64 and 3.28 mM rutin. However, at concentrations of 0.08, 0.16, 0.33 and 0.82 mM rutin cells were protected from DNA damage. Thus, in human lymphocytes quercetin and rutin displayed protective effects on DNA damage induced by mitomycin C, in a concentration-dependent manner.

Antibiotics, Antineoplastic↗
PubMed2003

Antioxidant status and mineral contents in tissues of rutin and baicalin fed rats.

The versatile benefit effects of flavonoids lead some nutritionists to believe that they are micronutrients. However, excess intake of flavonoids may cause side effects. In this paper, the effects produced by a higher intake of rutin and baicalin on antioxidant status as well as trace minerals such as iron, copper and zinc in rat tissues were studied. When rats were fed a rutin or baicalin containing diet (1%) for 20 days, the body weight gain was lower than that of the control group. Both rutin and baicalin caused significant a decrease of catalase activity and a moderate increase of total superoxide dismutase activity in the liver. The total antioxidant status of flavonoid fed rats was increased in the liver but decreased in the serum. In comparison to the control group, the lipid peroxidation level in the liver of the rutin fed group was significantly decreased; however, there was no statistical significance in the liver of the baicalin fed group and the brain of both flavonoids groups. The liver homogenates of both flavonoid fed rats significantly inhibited alkyl radical-induced lipid peroxidation. The iron contents in the liver of flavonoid fed rats were significantly decreased; rutin also caused zinc and copper decrease in the liver. These results indicated that high flavonoid intake can improve rat antioxidant systems in the liver; while it can also cause a trace mineral decrease and, in turn, reduce the activities of some metal-containing enzymes and may cause harmful effects on health.

Animals↗
PubMed1997

The flavonols quercetin, rutin and morin in DNA solution: UV-vis dichroic (and mid-infrared) analysis explain the possible association between the biopolymer and a nucleophilic vegetable-dye.

Previous studies showed evidence that quercetin can bind DNA by intercalation [R. Solimani et al., J. Agric. Food Chem. 43 (1995) 876-882] and a comparison with the flavanol dihydroquercetin indicated that the interaction is correlated to the planarity and hydrophobicity of the benzopyranic-4-one plane [R. Solimani, Int. J. Biol. Macromol. 18 (1996) 287-295]. In this study flow linear dichroism (LD) spectra of the hydrophobic quercetin were compared with hydrophilic aglycoside morin and 3-glycoside rutin in the same conditions: [DNA] = 3.1 x 10(-2) mol/l phosphate, [dye] = (1.0-4.0) x 10(-4) mol/l. Morin and rutin in an aqueous environment showed the same behaviour as quercetin in buffer-ethanol (70:30, v/v) solution, with their common benzopyranic-4-one part within the biopolymer. The LD(R) values (LD normalised to the relative isotropic absorption) indicated a greater affinity of the quercetin for the DNA. Comparison of the LD(R) of morin and rutin showed a ratio LD(R)morin/LD(R)rutin approximately 1.1-1.2 very close to unity and this suggests the localisation of the 3-rutinoside of rutin outside the intercalation site. Dichroic measurements recorded in extreme conditions of concentration partly clarified the sequences of interaction between quercetin and DNA in solution which shows the prototypical behaviour of the flavonolic group. This consists of an initial weak external association, where an electrostatic component is excluded, and which can evolve to intercalation changing the DNA concentration, whereas the quantity of the flavonol influences relatively the association. The carbonylic region of the benzopyranic-4-one chromophore is probably localised outside the intercalation site. This was suggested by indirect infrared (attenuated total reflection ATR) data of the quercetin-ethanol solution: the presence of free and chelated carbonyl determines a greater density of negative charges in this region of the chromophore, with the consequent lower probability of this portion penetrating the external polyanionic perimeter of the DNA. A simple approach to determine the order of magnitude of the anisotropic band II of the flavonols completely covered by the more intense DNA band at 260 nm, was also proposed. The low number of intercalated chromophores did not determine an alteration of the flexibility and hydrodynamic behaviour of the biopolymer and this can be correlated to a biological consideration: the flavonols probably do not interfere with the genetic functionality of the DNA. In contrast, the potentially close relationship between these nucleophilic dyes and the biopolymer, shown in this study, suggests a protective role on the nucleophilic groups of the DNA, which are a target of free radicals and the reactive electrophilic groups.

Anisotropy↗
PubMed2000

Mechanism of protection by the flavonoids, quercetin and rutin, against tert-butylhydroperoxide- and menadione-induced DNA single strand breaks in Caco-2 cells.

Protection by the flavonoids, quercetin and rutin, against tert-butylhydroperoxide (tert-BOOH)- and menadione-induced DNA single strand breaks was investigated in Caco-2 cells. Both tert-BOOH and menadione induced DNA single strand breaks in a concentration-dependent manner. Pre-incubation of Caco-2 cells with either quercetin or rutin for 24 h significantly decreased the formation of DNA single strand breaks evoked by tert-BOOH (P <.05). Iron chelators, 1,10-phenanthroline (o-Phen) and deferoxamine mesylate (DFO), also protected against tert-BOOH-induced DNA damage, whereas butylated hydroxytoluene (BHT) had no effect. Quercetin, and not rutin, decreased the extent of menadione-induced DNA single strand breaks. DFO and BHT, and not o-Phen, protected against menadione-induced DNA strand break formation (P <.05). From the results of this study, iron ions were involved in tert-BOOH-induced DNA single strand break formation in Caco-2 cells, whereas DNA damage evoked by menadione was far more complex. We demonstrated that the flavonoids, quercetin and rutin, protected against tert-BOOH-induced DNA strand breaks by way of their metal ion chelating mechanism. However, quercetin, and not rutin, protected against menadione-induced DNA single strand breaks by acting as both a metal chelator and radical scavenger.

Butylated Hydroxytoluene↗