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PubMedDate not supplied

Enzymatic synthesis and antioxidant properties of poly(rutin).

Rutin, quercetin-3-rutinoside, is one of the most famous glycosides of flavonoid and widely present in many plants. In this study, we performed an oxidative polymerization of rutin using Myceliophthora laccase as catalyst in a mixture of methanol and buffer to produce a flavonoid polymer and evaluated antioxidant properties of the resultant polymer. Under selected conditions, the polymer with molecular weight of several thousands was obtained in good yields. The resulting polymer was readily soluble in water, DMF, and DMSO, although rutin monomer showed very low water solubility. UV measurement showed that the polymer had broad transition peaks around 255 and 350 nm in water, which were red-shifted in an alkaline solution. Electron spin resonance (ESR) measurement showed the presence of a radical in the polymer. The polymer showed greatly improved superoxide scavenging activity and inhibition effects on human low-density lipoprotein (LDL) oxidation initiated by 2,2'-azobis(2-amidinopropane)dihydrochloride (AAPH), compared with the rutin monomer. The polymer also protected endothelial cells from oxidative injury induced by AAPH as a radical generator with a much greater effect than the rutin monomer.

Animals↗
PubMed2001

Chemiluminescence investigation of detection of rutin in medicine and human urine using controlled-reagent-release technology.

A novel continuous-flow sensor based on chemiluminescence (CL) detection was developed for the determination of rutin in pharmaceutical preparations and human urine by controlled-reagent-release technology. The analytical reagents involved in the CL reaction, including luminol and hexacyanoferrate(III), were both immobilized on an anion-exchange column in a flow-injection system. The CL signal produced by the reaction between luminol and hexacyanoferrate(III), which were eluted from the column through sodium phosphate injection, was decreased in the presence of rutin. CL intensity was inhibited by rutin; the decrement of CL intensity was linear over the logarithm of the rutin concentration range of 1.0-400 ng x mL(-1), and the detection limit was 0.35 ng x mL(-1) (3 sigma). The whole process, including sampling and washing, could be completed in 1.5 min with a relative standard deviation of <3.5%. The flow sensor showed remarkable stability and could be easily reused >450 time; the sensor proposed was applied successfully to the determination of rutin in pharmaceutical preparations and human urine.

Chromatography, Ion Exchange↗
PubMed2006

Effect of molecular sieves on lipase-catalyzed esterification of rutin with stearic acid.

Rutin was acylated with stearic acid in the esterification reaction catalyzed by immobilized Candida antarctica lipase B (Novozym 435) in tert-amyl alcohol with and without molecular sieves. The lipophilic rutin stearate was synthesized by this method, which had a potential use in food, cosmetics, and pharmacy. The structure of rutin stearate was characterized by spectral methods of 1H NMR and 13C NMR, Fourier transform infrared, and UV-vis. The results suggested that the regioselectivity of the lipase-catalyzed esterification of rutin was specific at the C(4''')-position of the rhamnose moiety. It was found that the addition of molecular sieves increased both the reaction rate and the yield. The time effect of adding molecular sieves in the reaction system on the conversion of rutin stearate was further examined. Instead of adding molecular sieves at the beginning of the reaction, the addition of molecular sieves at 5, 18, 24, 31, and 44 h after the beginning of the reaction was also applied. The final conversion for the case to add molecular sieves at 24 h after the beginning of reaction was the highest, with the conversion yield about 46%.

Acylation↗
PubMed2006

The relative contribution of the small and large intestine to the absorption and metabolism of rutin in man.

Tomato juice containing rutin (quercetin-3-rutinoside) was ingested by healthy volunteers and ileostomists. Blood and urine collected over 24 h were analysed by HPLC with photodiode array (PDA) and tandem mass spectrometric detection. Low concentrations of isorhamnetin-3-glucuronide (Cmax = 4.3 +/- 1.5 nmoles/l) and quercetin-3-glucuronide (Cmax = 12 +/- 2 nmoles/l) were detected in plasma of healthy subjects. Metabolites appeared in blood after 4 h indicating absorption from the large intestine. Nine metabolites of rutin were detected in urine but with considerable variation in total amount (40 +/- 1-4981 +/- 115 nmoles over 24 h). No metabolites were detected in plasma or urine of ileostomists and 86 +/- 3% of the ingested rutin was recovered in ileal fluid. In subjects with an intact large intestine, but not ileostomists, rutin was catabolised with the appearance of 3,4-dihydroxyphenylacetic acid, 3-methoxy-4-hydroxyphenylacetic acid and 3-hydroxyphenylacetic acid in urine accounting for 22% of rutin intake.

Adult↗
PubMed2006

Protective effect of rutin on lipids, lipoproteins, lipid metabolizing enzymes and glycoproteins in streptozotocin-induced diabetic rats.

The protective role of rutin on lipids, lipoproteins, lipid metabolizing enzymes and glycoproteins in streptozotocin-induced diabetic rats has been studied. A single intraperitoneal injection of streptozotocin (50 mg kg(-1)) to rats led to a significant (P < 0.05) increase in the levels of lipids (cholesterol, triglycerides, free fatty acids and phospholipids) in plasma and tissues (liver, kidney, heart and brain). The levels of low density and very low density lipoprotein (LDL and VLDL, respectively) cholesterol were increased, whereas the levels of high density lipoprotein (HDL) cholesterol were decreased significantly (P < 0.05) in plasma. The activity of 3-hydroxy 3-methylglutaryl coenzyme A (HMG CoA) reductase increased significantly (P < 0.05) in liver, kidney and heart, and the activity of lipoprotein lipase (LPL) and lecithin cholesterol acyltransferase (LCAT) decreased significantly (P < 0.05) in the plasma of diabetic rats. Streptozotocin injection also increased the levels of glycoproteins such as hexose, hexosamine, fucose and sialic acid in plasma, liver and kidney. Oral administration of rutin to streptozotocin-induced diabetic rats significantly (P < 0.05) decreased the levels of lipids in plasma and tissues. The levels of plasma HDL-cholesterol increased and the levels of LDL- and VLDL-cholesterol decreased significantly (P < 0.05). The activity of HMG CoA reductase decreased in the tissues and the activity of plasma LPL and LCAT increased significantly (P < 0.05). The levels of glycoproteins were found to be significantly (P < 0.05) decreased in plasma, liver and kidney of rutin-treated diabetic rats. Rutin administration to normal rats did not exhibit any significant (P < 0.05) changes in any of the parameters studied. In conclusion, the beneficial effect of rutin on lipids, lipoproteins, lipid metabolizing enzymes and glycoproteins could be due to its antioxidant property.

Animals↗
PubMed2000

Rutin inhibits ovariectomy-induced osteopenia in rats.

Several studies suggest that polyphenols might exert a protective effect against osteopenia. The present experiment was conducted to observe the effects of rutin (quercetin-3-O-glucose rhamnose) on bone metabolism in ovariectomized (OVX) rats. Thirty 3-month-old Wistar rats were used. Twenty were OVX while the 10 controls were sham-operated (SH). Among the 20 OVX, for 90 days after surgery 10 were fed the same synthetic diet as the SH or OVX ones, but 0. 25% rutin (OVX + R) was added. At necropsy, the decrease in uterine weight was not different in OVX and OVX + R rats. Ovariectomy also induced a significant decrease in both total and distal metaphyseal femoral mineral density, which was prevented by rutin consumption. Moreover, femoral failure load, which was not different in OVX and SH rats, was even higher in OVX + R rats than in OVX or SH rats. In the same way, on day 90, both urinary deoxypyridinoline (DPD) excretion (a marker for bone resorption) and calciuria were higher in OVX rats than in OVX + R or SH rats. Simultaneously, plasma osteocalcin (OC) concentration (a marker for osteoblastic activity) was higher in OVX + R rats than in SH rats. High-performance liquid chromatography (HPLC) profiles of plasma samples from OVX + R rats revealed that mean plasma concentration of active metabolites (quercetin and isorhamnetin) from rutin was 9.46+/-1 microM, whereas it was undetectable in SH and OVX rats. These results indicate that rutin (and/or its metabolites), which appeared devoid of any uterotrophic activity, inhibits ovariectomy-induced trabecular bone loss in rats, both by slowing down resorption and increasing osteoblastic activity.

Animals↗
PubMed2002

Effects of rutin supplementation on antioxidant status and iron, copper, and zinc contents in mouse liver and brain.

The effect of rutin on total antioxidant status as well as on trace elements such as iron, copper, and zinc in mouse liver and brain were studied. Mice were administrated with 0.75 g/kg or 2.25 g/kg P. O. of rutin for 30 d consecutively. Following the treatment, the activity of total antioxidant status, catalase, Cu,Zn-superoxide dismutase, Mn-superoxide dismutase, zinc, copper, and iron were measured in mouse liver and brain. The results showed that rutin significantly increased the antioxidant status and Mn-superoxide dismutase activities in mouse liver, but it had no effect on these variables in the brain. Treatment with a higher concentration of rutin significantly decreased catalase activity and iron, zinc, and copper contents in mouse liver; it also resulted in a slower weight gain for the first 20 d. These results indicate that rutin taken in proper amount can effectively improve antioxidant status, whereas at an increased dosage, it may cause trace element (such as iron, zinc, and copper) deficiencies and a decrease in the activities of related metal-containing enzymes.

Animals↗
PubMed2002

Biological effects of rutin on the survival of Escherichia coli AB1157 and on the electrophoretic mobility of plasmid PUC 9.1 DNA.

The use of natural products as medicines is growing in the world. The rutin, a compound isolated from Ruta graveolens, is a flavonoid, which has been suggested to have antioxidant properties and to reduce the triacylglycerol levels. In this study, plasmid desoxyribonucleic acid (DNA) was exposed to rutin (0.33, 10, 20, 30 microg/ml) in presence of stannous chloride (SnCl2), a reducing agent widely used to obtain radiopharmaceuticals labeled with technetium-99m. Samples of the plasmid DNA were analyzed through agarose gel electrophoresis. E. coli AB1157 culture was also incubated with rutin (3, 30, 50, 100 microg/ml) and the survival fractions were calculated. The results show that the rutin, in these concentrations, is not capable of: i/ damaging the DNA, ii/ protecting the DNA from the SnCl2 redox action, and iii/ inactivating the E. coli AB1157 culture. The analysis of our data indicates that rutin do not present toxic activity in the evaluated systems.

Antioxidants↗
PubMed2001

[Determination of rutin and quercetin in mulberry leaves by high performance capillary electrophoresis].

Rutin and quercetin are the main effective components of mulberry leaves with the functions of controlling the increase of fat in serum and controlling the formation of arterio-sclerosis. In this article a high performance capillary electrophoretic(HPCE) method was used to separate and determine rutin and quercetin in mulberry leaves collected from different periods, different places and different kinds in Xinjiang. Electrophoretic conditions were as follows: a capillary tube (75 microns i.d. x 57 cm (effective length, 50 cm)), with 10 mmol/L dihydrogen sodium phosphate-20 mmol/L sodium borate containing 15% methanol as the running buffer (pH 8.62) and an applied voltage of 20 kV, at 25 degrees C, detected at a wavelength of 245 nm. Under the optimum conditions, rutin and querctin were separated successfully from other components within 12 minutes. The corrected peak areas of rutin and quercetin increased linearly with the increase of their concentrations in the range of 4.4 mg/L-28.8 mg/L and 1.8 mg/L-145.8 mg/L respectively. The corresponding regression equations for rutin and quercetin were Y = 71.60 rho + 30.51 (r = 0.9991) and Y = 315.17 rho - 929.70 (r = 0.9949) respectively, and the recoveries were 95.64% and 99.36%. The analytical results demonstrate the method is simple, quick and well reproducible, and can be used as a reliable tool for the quality control of mulberry leaves.

Drugs, Chinese Herbal↗
PubMed2002

[Study on the absorption of quercetin and rutin at different segments of intestine].

The absorption of quercetin and rutin at different segments of intestine was examined. Seventy two Wistar rats were divided randomly into 3 groups (control group, quercetin group and rutin group), each group was divided into 4 subgroups (duodenum group, jejunum group, ileum group and colon group). Different solutions (1% dimethyl sulfoxide, 20 mumol/L of quercetin and rutin) were perfused respectively. At the end of perfusion, effluent solution samples were analyzed with HPLC. The results showed that both quercetin and rutin could be absorbed at different segments of intestine, but the absorption of rutin was significantly lower than quercetin. On the length basis, the absorption rate of quercetin was colon > ileum > duodenum > jejunum. On the area basis, the absorption rate was ileum > jejunum > duodenum > colon. After the perfusion of quercetin, there were unidentified peaks appearing on HPLC chromatogram. The results suggested that quercetin was derived from intestine and then re-excreted into intestinal lumen.

Animals↗
PubMed2006

[Comparative study on effects of rutin and quercetin on metabolism in osteoblast cells].

OBJECTIVE: To investigate the mechanism of rutin and its aglycone (quercetin) in preventing and treating osteoporosis and their effects on stimulating bone formation were studied comparatively in osteoblast cells. METHODS: The effects of rutin and quercetin on the proliferation, differentiation and mineralization were studied respectively by using tetrazolium (MTT), alkaline phosphatase (ALP) and mineralized nodules assays in newborn rat calvarial osteoblast (ROB) cells. RESULTS: Quercetin showed significant stimulatory effects on proliferation and mineralization in ROB cells, so it could promote bone formation. However, rutin could not imporve stimulation of bone formation because it increased proliferation and inhibited differentation and had no remarkable influence on ROB cells in vitro. CONCLUSION: Rutin showed less activity than quercetin on bone formation in ROB cells in vitro. Therefore the mechanism that some foods and traditional Chinese medicine containing rutin can prevent and treat osteoporosis is that its metaboite in vivo can promote bone formation in ROB cells.

Alkaline Phosphatase↗
PubMed1988

[Chelating and antiradical effect of rutin during peroxidation of lipids from microsomes and liposomes].

The antioxidative effect of rutin (vitamin P) on Fe2+-induced lipid peroxidation (LPO) in bovine heart microsomes and lecithin liposomes was studied. It was shown that the LPO-induced inhibition of microsomes and liposomes in the presence of rutin occurs via two mechanisms, i.e., association of Fe2+ ions to form an inactive complex and a direct interaction between rutin and free radicals. The contribution of these mechanisms depends on the composition of the reaction mixture. In bovine heart microsomes and liposomes, ascorbic acid has a dual activity towards LPO. At high concentrations of Fe2+ necessary for LPO induction (approximately 1 x 10(-3) M), ascorbic acid blocks LPO, whereas at low Fe2+ concentrations (less than 1 x 10(-4) M) it has a prooxidative effect. A combined use of ascorbic acid and rutin results in an additive antioxidative effect at high Fe2+ concentrations (approximately 1.10(-3) M). However, at low Fe2+ concentrations rutin acts as an antagonist of the prooxidative effect of ascorbic acid.

Animals↗
PubMed1981

Studies on drug metabolism by use of isotopes XXVI: Determination of urinary metabolites of rutin in humans.

Determination of urinary metabolites of orally administered rutin and rutin-2',5',6'-d3 in humans was carried out by TLC and GLC-mass spectrometry. In human urine, 3-hydroxyphenylacetic acid, 3-methoxy-4-hydroxyphenylacetic acid, 3,4-dihydroxyphenylacetic acid, 3,4-dihydroxytoluene, and beta-m-hydroxyphenylhydracrylic acid were identified as rutin metabolites. Unchanged rutin and quercetin were not present in urine.

Biotransformation↗
PubMed1981

Carcinogenicity examination of quercetin and rutin in ACI rats.

Carcinogenicity of quercetin and rutin were examined in inbred ACI strain rats. Rats were given a diet containing 1% or 5% quercetin or 5% rutin for 540 days, or 10% quercetin and 10% rutin for 850 days. Rats in control groups were fed a normal basal diet. Most tumors found in experimental groups were also found in the corresponding control groups. Furthermore, there was no significant difference between the incidence of tumors in the experimental or control groups (P greater than 0.05). Thus, quercetin and rutin tested were not shown to be carcinogenic to ACI rats.

Animals↗
PubMed2002

In vitro and in vivo inhibitory activities of rutin, wogonin, and quercetin on lipopolysaccharide-induced nitric oxide and prostaglandin E(2) production.

Flavonoids are widely distributed in plants, but their biological functions are still unclear. In the present study, in vitro and in vivo experiments were performed to demonstrate the inhibitory activities of rutin, wogonin, and quercetin on lipopolysaccharide-induced nitric oxide (NO) and prostaglandin E(2) production in RAW 264.7 macrophages, primary peritoneal macrophages, and Balb/c mice, respectively. In vitro results showed that wogonin and quercetin dose-dependently suppressed lipopolysaccharide-induced NO production in RAW 264.7 macrophages and primary peritoneal macrophages without a notable cytotoxic effect on either cell types associated with a decrease in inducible nitric oxide synthase (iNOS) protein expression in both cells. Rutin, at 80 microM only, had a slight but obvious inhibitory effect on lipopolysaccharide-induced NO production in primary peritoneal macrophages. Both wogonin and quercetin attenuated lipopolysaccharide-induced prostaglandin E(2) production in vitro. Intravenous injection of lipopolysaccharide (10 mg/kg, i.v.) resulted in a time-dependent induction of NO production in serum, and pretreatment with the L-arginine analog N-nitro-L-arginine methyl ester (L-NAME) blocked this induction. Intravenous pretreatment of Balb/c mice with rutin, wogonin or quercetin for 1 h followed by lipopolysaccharide treatment significantly inhibited lipopolysaccharide-induced NO production, but no inhibition of prostaglandin E(2) production was found. A decrease in iNOS protein, but not cyclooxygenase-2 protein, was detected in liver and lung specimens of lipopolysaccharide-treated Balb/c mice in the presence of rutin, wogonin or quercetin. In conclusion, data obtained both in vitro and in vivo suggest that wogonin and quercetin exert inhibitory activity on lipopolysaccharide-induced NO production through suppression of iNOS expression.

Animals↗
PubMed1997

Bioavailability of rutin and quercetin in rats.

Quercetin is a powerful antioxidant which is widely distributed in edible plants, mainly as glycosides such as rutin. It has been reported to be absorbed in mammals, but its metabolism needs further investigation to evaluate its possible physiological effects. We compared the evolution of the absorption of quercetin and rutin in rats fed with supplemented diets. Rutin was absorbed more slowly than quercetin because it must be hydrolysed by the cecal microflora, whereas quercetin was absorbed from the small intestine. Conjugated derivatives of quercetin, and its methylated forms isorhamnetin and tamarixetin, were recovered in plasma from rats receiving the two kinds of experimental diets after the first meal, but after 10 days, no traces of tamarixetin were detected anymore. The rate of elimination of quercetin metabolites seems very low, and high plasma concentrations are easily maintained with a regular supply of quercetin or rutin in the diet.

Adaptation, Physiological↗
PubMed2002

Evaluation of the genotoxic effect of rutin and quercetin by comet assay and micronucleus test.

Flavonoids are phenolic compounds, naturally found in vegetables, tea and red wines. A recent study has demonstrated that the flavonoids rutin and quercetin show a protective role against the deleterious effects of free radicals in cirrhotic rats. Considering this finding and the controversial results concerning the mutagenicity of rutin and quercetin recorded in the literature, the capacity of these flavonoids to cause damage to the DNA was evaluated using the alkaline single-cell gel electrophoresis (SCG) and micronucleus test in the bone marrow of mice. The doses for both compounds were 2 x 2500, 2 x 1250 and 2 x 625 mg/kg. Micronucleus test showed that rutin caused no damage to the DNA of the mice bone marrow cells, and the SCG assay demonstrated an increase of damage only at the dose of 2 x 1250 mg/kg. But when the mice cells of the three quercetin doses were compared with the negative control, significantly higher damage was observed by SCG assay, although not proportional to the dose. The micronucleus test also demonstrated a significant increase of damage, but only at the 2 x 1250 mg/kg dose. Considering the results obtained in this study with very high doses, it is unlikely that the consumption of rutin and quercetin produces any clastogenic effects. Our results also indicated that SCG could profitably be used in drug genotoxicity evaluation protocols.

Animals↗