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PubMed2003

Tartary buckwheat (Fagopyrum tataricum Gaertn.) as a source of dietary rutin and quercitrin.

Two samples of tartary buckwheat (Fagopyrum tataricum Gaertn.) from China and one from Luxembourg were studied by high-performance liquid chromatography (HPLC) to reveal the possibilities of growing tartary buckwheat herb as a possible source of rutin, quercetin, and quercitrin. The content of rutin was determined as up to 3% dry weight (DW) in tartary buckwheat herb. Quercitrin values were in the range of 0.01-0.05% DW. Only traces of quercetin were detected in just some of the samples. Tartary buckwheat seeds contained more rutin (about 0.8-1.7% DW) than common buckwheat seeds (0.01% DW). Rutin and quercetin content in seeds depends on variety and growing conditions. Tartary buckwheat seeds contained traces of quercitrin and quercetin, which were not found in common buckwheat seeds.

Chromatography, High Pressure Liquid↗
PubMed2002

Rutin is essential for the antidepressant activity of Hypericum perforatum extracts in the forced swimming test.

It has been shown that aqueous alcoholic extracts of Hypericum perforatum (St. John's wort) are active in the forced swimming test (FST), an animal model for antidepressant activity. In this study, a series of ethanolic and methanolic extracts were investigated and, in almost all cases, the extracts showed strong activity. Only one methanolic research extract had no effect in the in vivo pharmacological experiments. Analytical characterisation using HPLC showed that the inactive extract had a reduced level of the diglycoside flavonoid rutin. Addition of rutin to the inactive extract, to produce a concentration within the normal range, resulted in a strong pharmacological effect comparable to that of the other extracts. First experiments suggest that this re-activation is not dose-dependent, indicating that rutin must be present above a threshold limit. It therefore appears vital that extracts of St. John's wort which are designed for the therapy of depressive disorders should be manufactured using plant material with sufficient amounts of rutin.

Animals↗
PubMed1995

Quercetin metabolites in plasma of rats fed diets containing rutin or quercetin.

We studied the bioavailability and the plasma transport of flavonols in rats fed quercetin or rutin diets. Wistar rats were fed one of the following purified diets for 10 d: control; 16.4 or 8.2 mmol rutin/kg diet; or 16.4, 8.2 or 4.1 mmol quercetin/kg diet. Flavonol concentrations were determined in plasma, ileal and cecal contents, and feces. In rats fed diets containing 16.4 mmol quercetin or rutin/kg, the concentration of circulating flavonols was approximately 115 mumol/L. Quercetin or rutin administration resulted in similar concentrations of quercetin in cecal contents. By HPLC analysis and beta-glucuronidase/sulfatase treatment, plasma flavonols have been identified as conjugated quercetin itself, or a conjugated form (4.5-fold as abundant) of an aglycone less polar than quercetin. Rats fed quercetin or rutin diets had a green/yellow-colored plasma that exhibited a peak absorbance at 411 nm, vs. 363 or 375 nm for pure rutin or quercetin solutions, respectively. This shift of band I absorption was obtained when pure quercetin was in the presence of albumin or added to a plasma fraction. The bathochromic properties of flavonoids in the presence of albumin are highly dependent on the presence of the C-2/C-3 double bond on the C-ring and are influenced by the degree of B-ring hydroxylation. The existence of intermolecular bonds between albumin and quercetin is supported by in vitro absorbance and fluorescence studies. With human albumin, the fluorescence intensity and the shift of quercetin absorbance increased in parallel to the albumin/quercetin molar ratio. Conjugated diene formation, resulting from Cu(2+)-catalyzed oxidation of human LDL or rat VLDL+LDL was effectively inhibited in vitro by 0.5 mumol/L quercetin. These results show that dietary flavonols are recovered in rat plasma as conjugated metabolites in non-negligible concentrations, and that these flavonols may be interesting antioxidant micronutrients with a variety of biological effects.

Albumins↗
PubMed2006

Quercetin, but not its glycosidated conjugate rutin, inhibits azoxymethane-induced colorectal carcinogenesis in F344 rats.

The effect of the flavonoid quercetin and its conjugate rutin was investigated on (biomarkers of) colorectal cancer (CRC). Male F344 rats (n = 42/group) were fed 0, 0.1, 1, or 10 g quercetin/kg diet or 40 g rutin/kg diet. Two wk after initial administration of experimental diets, rats were given 2 weekly subcutaneous injections with 15 mg/kg body wt azoxymethane (AOM). At wk 38 post-AOM, quercetin dose dependently (P < 0.05) decreased the tumor incidence, multiplicity, and size, whereas tumor incidences were comparable in control (50%) and rutin (45%) groups. The number of aberrant crypt foci (ACF) in unsectioned colons at wk 8 did not correlate with the tumor incidence at wk 38. Moreover, at wk 8 post-AOM, the number and multiplicity of ACF with or without accumulation of beta-catenin were not affected by the 10 g quercetin/kg diet. In contrast, another class of CRC-biomarkers, beta-catenin accumulated crypts, contained less beta-catenin than in controls (P < 0.05). After enzymatic deconjugation, the plasma concentration of 3'-O-methyl-quercetin and quercetin at wk 8 was inversely correlated with the tumor incidence at wk 38 (r = -0.95, P </= 0.05). Rats supplemented with 40 g rutin/kg diet had only 30% of the (3'-O-methyl-) quercetin concentration of 10 g quercetin/kg diet-fed rats (P < 0.001). In conclusion, quercetin, but not rutin, at a high dose reduced colorectal carcinogenesis in AOM-treated rats, which was not reflected by changes in ACF-parameters. The lack of protection by rutin is probably due to its low bioavailability.

Animals↗
PubMed2001

Fast repair of the radical cations of dCMP and poly C by quercetin and rutin.

The effects of quercetin and rutin on the repair of the radical cations of dCMP and poly C were studied using the technique of pulse radiolysis. The radical cations of dCMP and poly C were formed by the reaction of dCMP and poly C with SO( 4)(-). After pulse irradiation of nitrogen-saturated aqueous solutions containing dCMP, 20 mM K(2)S(2)O(8), 200 mM t-BuOH and either rutin or quercetin, the initially formed radical cation of dCMP, detected spectrophotometrically, rapidly decayed with the concurrent formation of the phenoxyl radical of rutin or quercetin within 8-40 micros. The repair efficiencies of the tested compounds towards the poly C radical cation were also determined using the same procedure. The results indicate that dCMP and poly C radical cations can be rapidly repaired by quercetin and rutin. The rate constants of the repair reactions were determined to be 4.3-8.8x10(8) M/s and 1.5-3.6x10(8) M/s for dCMP and poly C radical cations, respectively. Together with findings from our previous studies, the present results demonstrate that non-enzymatic fast repair may be a universal form of repair involving phenolic antioxidants.

Antioxidants↗
PubMed2003

Modeling the metabolism of idarubicin to idarubicinol in rat heart: effect of rutin and phenobarbital.

Since the severe cardiotoxicity of anthracyclines has been attributed to the intramyocardial formation of C-13 alcohol metabolites, the kinetics of cardiac metabolite formation and disposition as well as the effect of carbonyl reductase inhibitors are of specific interest. This study was designed to investigate the effect of rutin and phenobarbital on the pharmacokinetics of idarubicin (IDA) and its conversion to idarubicinol (IDOL) in the single-pass perfused rat heart. After infusion of IDA (0.5 mg) during 1min, the venous outflow concentrations of IDA and IDOL were measured up to 80 min in the presence and absence of rutin and phenobarbital. A kinetic model was developed to help to interpret the concentration profiles in terms of compartmentation of IDOL formation and to estimate parameters quantitatively descriptive of the transport and biotransformation processes. Rutin and phenobarbital significantly reduced the residual amount of IDOL in heart to 64 and 47% of control, respectively. Pharmacokinetic modeling of the data revealed that IDOL is generated in two different compartments, besides the tissue compartment characterized by saturable uptake, also the compartment that accounts for the quasi-instantaneous initial distribution process is involved. The efflux rate constant of IDOL, k(21,IDOL,) was much smaller than that of IDA. Rutin and phenobarbital significantly reduced IDOL production. Additionally, phenobarbital competitively inhibited the saturable uptake of both IDA and IDOL (increase in apparent Michaelis constants). Reanalysis of data obtained in previous experiments showed that P-glycoprotein inhibitors (verapamil and amiodarone) reduced IDOL uptake in a similar way as already shown for IDA. The present study further supports the utility of pharmacokinetic modeling in identifying sites of drug interactions within the heart.

Amiodarone↗
PubMed2006

Preventive effect of rutin, a bioflavonoid, on lipid peroxides and antioxidants in isoproterenol-induced myocardial infarction in rats.

The consumption of diets rich in plant foods is associated with a reduced risk of cardiovascular diseases. This study aimed to evaluate the preventive role of rutin on lipid peroxides and antioxidants in normal and isoproterenol-induced myocardial infarction in rats. Subcutaneous injection of isoproterenol (150 mg kg(-1)) to male Wistar rats at an interval of 24 h for two days showed a significant increase in the activity of serum cardiac marker enzymes (creatine kinase, lactate dehydrogenase, aspartate transaminase and alanine transaminase) and a significant decrease in the activity of these enzymes in the heart. Lipid peroxidative products (thiobarbituricacid reactive substances and lipid hydroperoxides) were significantly increased and enzymic (superoxide dismutase, catalase and glutathione peroxidase) and non-enzymic (reduced glutathione and vitamin C) antioxidants showed a significant decrease in isoproterenol-treated rats. Pretreatment with rutin (40 or 80 mg kg(-1)) to isoproterenol-treated rats orally for a period of 42 days daily caused a significant effect. Administration of rutin to normal rats did not have any significant effect on any of the parameters studied. The results of our study show that rutin possesses antioxidant activity in isoproterenol-induced experimental myocardial infarction.

Animals↗
PubMed2004

[Effect of hesperidin and rutin on oxidative modification of high density lipoprotein in vitro].

OBJECTIVE: To study the effect of hesperidin and rutin on oxidative modification of high density lipoprotein (HDL) in vitro. METHODS: HDL was isolated from healthy human plasma by sequential ultracentrifugation, and was oxidized by copper ions. The inhibitory effects of hesperidin and rutin on HDL oxidative modification were valued by the formation of malondialdehyde (MDA). RESULTS: Hesperidin and rutin significantly inhibited copper-induced oxidation of HDL in a dose-dependent manner. CONCLUSION: Both hesperidin and rutin can prevent HDL from copper-induced oxidative modification in vitro. This result suggests that they might have antiatherogenic effect.

Arteriosclerosis↗
PubMed2002

[Experimental study on inhibitory effect of rutin against platelet activation induced by platelet activating factor in rabbits].

OBJECTIVE: To explore the inhibitory effect and mechanism of rutin against platelet activating factor (PAF) induced platelet aggregation, 5-HT release and intra-platelet free calcium concentration. METHODS: The rate of washed rabbit platelet (WRP) aggregation was measured by turbidimetry and O-phthaldialdehyde (OPT) fluoro-spectrophotometry (FSPM) was used to determine 5-HT content. The intraplatelet free calcium concentration was measured with Fura-2/AM FSPM assay. RESULTS: Rutin in vitro was concentration-dependently inhibiting PAF (9.55 x 10(-9) mol/L) induced WRP aggregation, the IC50 of 5-HT release was 0.73, 1.13 mmol/L respectively and the intraplatelet free calcium concentration elevation evoked by PAF (4.78 x 10(-10) mol/L) were inhibited by 68.3, 136, 274, 545 mumol/L of rutin dose-dependently. CONCLUSION: Rutin could inhibit PAF induced platelet aggregation, 5-HT release and the increase of intraplatelet free calcium.

Animals↗
PubMed2004

[Inhibitory effect of quercetin, rutin and puerarin on HDL oxidation induced by Cu2+].

OBJECTIVE: To evaluate the inhibitory effect of quercetin, rutin and puerarin on the HDL oxidation induced by Cu2+ and to investigate their action on the prevention and cure of atherosclerosis. METHODS: The serum HDL of healthy human was isolated by the one step density gradient ultracentrifugation. The HDL oxidation was induced by Cu2+ in vitro for different time, quercetin and rutin at 5 micromol/L were added ahead, respectively. HDL was oxidized, then identified by A234, REM, TBARS and protein carbonyls content, and was compared with control group. Inhibition of puerarin was weak. RESULTS: (1) A234, REM, TBARS and protein carbonyls formation increased gradually during HDL oxidation induced by Cu2+ in vitro. (2) During HDL oxidation induced by Cu2+ in vitro and incubation with quercetin and rutin, the kinetic changes of A234, REM, TBARS and protein carbonyls formation showed lag phases of 2 h, 2-4 h, 2-4 h and 4 h respectively, and showed reductions by 24.2%-49.0% (P<0.001) and 9.4%-42.0% (P<0.01); 3.0%-25.0% and 4.0%-20.7% (P<0.05); 7.9%-34.1% and 1.2%-26.8% (P<0.05); 28.3%-50.4% and 18.6%-64.6% (P<0.001) respectively. In the puerarin group, only protein carbonyls formation showed a lag phase of 4 h and a reduction by 14.1%-52.1% (P<0.001) while its A234, REM, TBARS reduced to a small extent. CONCLUSION: The above findings suggested that quercetin and rutin inhibit oxidation of HDL significantly, but puerarin has less antioxidative function.

Antioxidants↗
PubMed2004

[Determination of scutellarin and rutin in Shenfukang capsules by reversed-phase high performance liquid chromatography].

A rapid and simple method for the determination of scutellarin and rutin in Shenfukang capsules has been developed using reversed-phase high performance liquid chromatography. Scutellarin and rutin were first extracted by ultrasonic extraction with methanol-water (1:1, v/v). The resulting extracts were separated on a C18 column (4.6 mm i.d. x 150 mm, 5 microm). The mobile phase consisting of 0.02 mol/L KH2PO4 solution containing 1.0% glacial acetic acid-methanol (63:37, v/v) was run at a flow rate of 1.0 mL/min. The detection wavelength was 330 nm and the injection volume was 20 microL. Good linearity in the range of 10 mg/L to 300 mg/L was obtained for scutellarin and rutin. The method was successfully used for the quantification of scutellarin and rutin of Shenfukang capsules.

Apigenin↗
PubMed2005

[Oxidative metabolism of neutrophils in obese patients before and during body mass reduction: the in vitro effect of quercetin and rutin].

Obese people are at high risk for developing diabetes, dyslipidemia, hypertension, and cardiovascular diseases, which lead to an increased risk of mortality. Activated polymorphonuclear neutrophils (PMN) generate extremely high amounts of reactive oxygen species (ROS), but these are normally targeted at pathogens inside intracellular phagosomes. These same beneficial antimicrobial functions can cause significant local tissue injury and lead to the development of pathologic systemic inflammatory conditions. PMN apoptosis is a major mechanism associated with the resolution of inflammatory reactions. The goals of the present study were: 1) to evaluate the level of reactive oxygen species production in PMN from obese people before and during body mass reduction, 2) to investigate the in vitro effect of flavonoids: quercetin and rutin on oxidative metabolism and apoptosis of stimulated neutrophils in obese patient. We tested 30 obese patients (women) before body mass reduction and 20 patients during low calories diet. The inclusion criteria were based on physical examination, BMI, WHR, the body composition examination based on bioimpedance method and biochemical assessment. PMN were isolated and oxidant production, in response to 1 microg/ml PMA, was characterised by the production of hydrogen peroxide, nitric oxide and chemiluminescence intensity. Caspase-3 activation was assayed by the method of DEVD-AMC cleavage in PMN cultured up to 24 hours. The results of our study showed: 1) the decrease in PMN oxidant production in patient during the mass reduction, 2) the strong antioxidant activity of quercetin and rutin in obese patients before and during the body mass reduction, these effects were dose dependent and rutin was less potent than quercetin, 3) acceleration of PMN apoptosis by rutin is associated with an increase in caspase 3 activity.

Adult↗
PubMed1984

Characterization of oral streptococci that activate the dietary glycoside rutin to a mutagen.

Oral streptococci are described that hydrolyze the dietary glycoside rutin (CAS: 153-18-4), resulting in mutagenic activity. Bacteria that hydrolyze rutin were isolated from the mouth of each of 10 healthy volunteers. The activity was inducible, and the product was mutagenic in the Salmonella mutagenicity assay. These bacteria were present in the greatest proportion on the dorsum of the tongue where they formed 1.5% of the total cultivable microflora. The appearance of the colonies, cell morphology, and biochemical characteristics were those of Streptococcus milleri. However, rutin hydrolysis did not occur with any of 30 isolates of this species from blood of patients with bacteremia, with any of 4 stock strains, or with any of 14 strains of streptococci from the other 4 major oral species. Therefore, activation of rutin to a mutagen is not a universal function of the normal oral flora, but it can be accomplished by some strains of S. milleri.

Biotransformation↗
PubMed1983

The role of rutin and quercitrin in stimulating flavonol glycosidase activity by cultured cell-free microbial preparations of human feces and saliva.

The non-mutagenic flavonol glycosides, rutin and quercitrin, are hydrolysed by cell-free extracts of human fecal cultures to the mutagenic product, quercetin, detectable in the Ames test and by thin-layer chromatography. Cell-free extracts of human saliva cultures hydrolyse rutin but not quercitrin. The pH optima for rutin glycosidase is 7.0 and for quercitrin glycosidase, 5.0. These findings indicate that (a) the bulk of the glycosidase activity in cell-free preparations of fecal and salivary cultures is 'inducible'; (b) the two glycosidases are distinctly different; (c) they are produced by different organisms; and (d) both types of organisms are present in feces while only the rutin-glycosidase-elaborating organisms occur in saliva.

Biotransformation↗
PubMed2004

Comparative study on the inclusion behaviour of cyclodextrin derivatives with venoruton and rutin by thin layer chromatography.

The interaction of rutin and venoruton (troxerutin), with alpha-, beta- and gamma-cyclodextrin (CD), hydroxypropyl-beta-cyclodextrin (HP-beta-CD) and methyl-beta-cyclodextrin (M-beta-CD) was investigated by reversed-phase thin layer chromatography on polyamide plates. A mobile phase consisted of NH(4)OH; NH(4)Cl buffer solution containing various CD concentrations (pH = 9.7, 20 degrees C) was used as mobile phase. The equilibrium constants (K(f)) and the retention factor (R(f)) were determined and used to study the inclusion process. The in fluence of CDs on the solubility of rutin and venoruton was characterized by R(M) values and the increasing hydrophilicity of drugs. The results show that the inclusion capacity of cyclodextrins follows the order HP-beta-CD > M-beta-CD > beta-CD > gamma-CD, and rutin is more easily included by the studied cyclodextrins than venoruton. In addition, the thermodynamic parameters (Delta H, Delta S) for the formation of complexes were obtained from the van't Hoff equation, displaying the enthalpy-entropy compensation effect.

2-Hydroxypropyl-beta-cyclodextrin↗
PubMed2001

Inhibition of nitric oxide synthase inhibitors and lipopolysaccharide induced inducible NOS and cyclooxygenase-2 gene expressions by rutin, quercetin, and quercetin pentaacetate in RAW 264.7 macrophages.

Several natural flavonoids have been demonstrated to perform some beneficial biological activities, however, higher-effective concentrations and poor-absorptive efficacy in body of flavonoids blocked their practical applications. In the present study, we provided evidences to demonstrate that flavonoids rutin, quercetin, and its acetylated product quercetin pentaacetate were able to be used with nitric oxide synthase (NOS) inhibitors (N-nitro-L-arginine (NLA) or N-nitro-L-arginine methyl ester (L-NAME)) in treatment of lipopolysaccharide (LPS) induced nitric oxide (NO) and prostaglandin E2 (PGE2) productions, inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) gene expressions in a mouse macrophage cell line (RAW 264.7). The results showed that rutin, quercetin, and quercetin pentaacetate-inhibited LPS-induced NO production in a concentration-dependent manner without obvious cytotoxic effect on cells by MTT assay using 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide as an indicator. Decrease of NO production by flavonoids was consistent with the inhibition on LPS-induced iNOS gene expression by western blotting. However, these compounds were unable to block iNOS enzyme activity by direct and indirect measurement on iNOS enzyme activity. Quercetin pentaacetate showed the obvious inhibition on LPS-induced PGE2 production and COX-2 gene expression and the inhibition was not result of suppression on COX-2 enzyme activity. Previous study demonstrated that decrease of NO production by L-arginine analogs effectively stimulated LPS-induced iNOS gene expression, and proposed that stimulatory effects on iNOS protein by NOS inhibitors might be harmful in treating sepsis. In this study, NLA or L-NAME treatment stimulated significantly on LPS-induced iNOS (but not COX-2) protein in RAW 264.7 cells which was inhibited by these three compounds. Quercetin pentaacetate, but not quercetin and rutin, showed the strong inhibitory activity on PGE2 production and COX-2 protein expression in NLA/LPS or L-NAME/LPS co-treated RAW 264.7 cells. These results indicated that combinatorial treatment of L-arginine analogs and flavonoid derivates, such as quercetin pentaacetate, effectively inhibited LPS-induced NO and PGE2 productions, at the same time, inhibited enhanced expressions of iNOS and COX-2 genes.

Animals↗
PubMed2001

Fragmentation study of rutin, a naturally occurring flavone glycoside cationized with different alkali metal ions, using post-source decay matrix-assisted laser desorption/ionization mass spectrometry.

A post-source decay matrix-assisted laser desorption/ionization mass spectrometric (PSD-MALDI-MS) study of rutin, a naturally occurring flavone glycoside cationized with different alkali metal ions, is reported. The fragmentations of rutin were performed by selecting the [R + Cat]+ peaks for PSD, where R represents a rutin molecule and Cat an alkali metal ion (Li+, Na+, K+). The PSD-MALDI mass spectra showed, depending on Cat, different fragmentation patterns with respect to both the quality and quantity of the fragment ions formed. The intensity of fragmentation decreased in the order Li+ > Na+ > K+. The fragmentation mechanism and an explanation for the observed differences are suggested.

Cations↗
PubMed1999

Hypolipidaemic effects of naringenin, rutin, nicotinic acid and their associations.

Atherosclerosis can be defined as being a disease of coronary circulation. The present work evaluates the action of the naringenin, rutin, nicotinic acid, isolated and in association, on the metabolism of lipids. Cholesterol, cholesterol HDL, and triacylglycerols have been dosed after retreat of blood, following the administration of the compounds dissolved in propylene glycol by intraperitoneal route in doses of 5 mg kg-1 body wt. Results evidence that naringenin and nicotinic acid, isolated as well as their association with naringenin and nicotinic acid-rutin, present the largest percentual reduction of cholesterol. On the other hand, the best results for cholesterol-HDL have been obtained with naringenin, while rutin has shown the best triacylglycerols levels.

Animals↗