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Anti-inflammatory properties of plant flavonoids. Effects of rutin, quercetin and hesperidin on adjuvant arthritis in rat.

The anti-inflammatory activities of three flavonoids were investigated in rats using the Mizushima et al. model of acute and chronic inflammation. Intraperitoneal administration of rutin, quercetin (flavonols) and hesperidin (flavanone), given at daily doses equivalent to 80 mg/kg, inhibited both acute and chronic phases of this experimental model of inflammation. Rutin was the most active in the chronic phase.

Acute Disease↗

Determination of puerarin, daidzein and rutin in Pueraria lobata (Wild.) Ohwi by capillary electrophoresis with electrochemical detection.

A method based on capillary electrophoresis with electrochemical detection was developed for the determination of puerarin, daidzein and rutin. Effects of several important factors such as the acidity and concentration of running buffer, separation voltage, injection time, and detection potential were investigated to acquire the optimum conditions. The working electrode was a 300-microm diameter carbon disc electrode positioned opposite the outlet of capillary. The three analytes could be well separated within 12 min in a 40 cm length capillary at a separation voltage of 9 kV in a 50 mmol/l borate buffer (pH 9.0). The relationship between peak currents and analyte concentrations was linear over about three orders of magnitude with detection limits (SIN=3) ranging from 0.241 x 10(-6) to 0.511 x 10(-6) mol/l for all compounds. This proposed method demonstrated long-term stability and reproducibility with relative standard deviations of less than 5% for both migration time and peak current (n=7). It has been successfully applied for the determination of puerarin, daidzein and rutin in Chinese traditional drugs, the vines of Pueraria lobata (Wild.) Ohwi and Puerariae Radix.

Buffers↗

The extraction of rutin from flower buds of Sophora japonica.

The efficiency of extraction of rutin from Sophora japonica is improved by ultrasound but is dependent on the solvent employed. Rutin is a compound with antioxidant activity and aqueous solvents appear to be unsuitable for ultrasonic extractions due to the formation of free radicals from the insonation of the solvent. The application of ultrasound to methanolic extraction gave a significant reduction in extraction time and an increase in maximum yield.

Free Radicals↗

Preparation and spectral investigation on inclusion complex of beta-cyclodextrin with rutin.

Solid inclusion complex of rutin with beta-cyclodextrin (beta-CD) was prepared by coprecipitate method. The formation of inclusion complex was confirmed by differential scanning calorimetry (DSC) and X-ray diffraction. The formation constant was obtained by steady-state fluorescence measurements and the result suggested the complex preferred 1:1 (rutin:CD) stoichiometry. Furthermore, the spatial configuration of the complex has been proposed based on NMR and molecular modeling.

Cyclodextrins↗

Effects of lipase, lipoxygenase, peroxidase, and rutin on quality deteriorations in buckwheat flour.

To investigate the effects of changes in lipase, lipoxygenase, peroxidase (POX), and rutin concentrations on the quality of buckwheat flour, 14 buckwheat varieties were stored for 0, 4, 10, and 30 days at 5 or 20 degrees C. During the storage period, lipase activity correlated to pH (significantly negative) and water-soluble acid (WSA) (significantly positive). The lipoxygenase 1 protein concentration had a negative correlation to WSA (significant at 0 and 4 storage days at 5 degrees C and at 0 and 10 storage days at 20 degrees C). POX had significant correlation to pH and peroxide value (POV) at 5 degrees C, whereas it was not significant at 20 degrees C. The rutin concentration had negative correlations to WSA (significant at 30 days of storage at 5 degrees C and at 4 days of storage at 20 degrees C). Thus, lipase activity plays an important role that relates to lipid degradation in quality deterioration of buckwheat flour.

Fagopyrum↗

Treatment of metastatic melanoma B16F10 by the flavonoids tangeretin, rutin, and diosmin.

Melanoma is one of the most frequently metastasizing malignant neoplasias. This study examines an experimental model of pulmonary metastasis and the B16F10 cell subline, highly metastatic in the lung. Antimetastatic effects of the flavonoids tangeretin, rutin, and diosmin were analyzed, and at the same time an analysis of the metastatic activity of ethanol was performed, considered to be necessary because it is used as a vehicle for administering the flavonoids. Lentini's model, which complements the macroscopic evaluation of nodule numbers by using a stereoscopic microscope and image analysis at the microscopic level, was used. The greatest reduction in the number of metastatic nodules (52%) was obtained with diosmin; similarly, the percentages of implantation, growth index, and invasion index (79.40, 67.44, and 45.23%, respectively), were all compared with those of the ethanol group, considered to be an effective control group. Rutin- and tangeretin-treated groups also showed reductions of the same index compared with the ethanol group. It would seem that structural factors would better explain these results and the antimetastatic activity of each flavonoid and the respective metabolites.

Animals↗

Evidence for antiradical and antioxidant properties of four biologically active N,N-diethylaminoethyl ethers of flavanone oximes: a comparison with natural polyphenolic flavonoid (rutin) action.

The antiradical and antioxidant activities of four biologically active N,N-diethyloaminoethyl ethers of flavanone oximes (N,N-DEAEFo) were investigated in vitro and compared with these of polyphenolic flavonoid (rutin). Four experimental models were used: iron- and ascorbate driven Fenton systems, gamma-radiolysis, xanthine/xanthine oxidase system and diphenylpicrylhydrazyl (DPPH) radical scavenging. The results clearly indicate that N,N-DEAEFo are acting as promising antioxidants and radioprotectors comparable to rutin activities: they should prove to be useful under acute oxidative stress conditions for which both properties were required.

Antioxidants↗

Modulation of aberrant crypt foci and apoptosis by dietary herbal supplements (quercetin, curcumin, silymarin, ginseng and rutin).

It is estimated that one-third of Americans use dietary herbal supplements on a regular basis. Diets rich in bioactive phytochemicals are associated with reduced risk of certain cancers, notably, colon cancer. Herbal supplements have not been directly tested as sources of bioactive cancer preventives. Hence, this study compares the ability of four herbal flavonoids (quercetin, curcumin, rutin and silymarin) and one whole herb mixture (ginseng powder) to suppress aberrant crypt foci (ACF) in an azoxymethane (AOM)-induced rat colon cancer model. Second, this study examines the effect of these herbal compounds on apoptosis and the mechanisms by which these compounds evoke apoptosis. The results of this study show that diets containing quercetin, curcumin, silymarin, ginseng and rutin decreased the number of ACFs by 4-, 2-, 1.8-, 1.5- and 1.2-fold, respectively compared with control. Histological analysis of the colon mucosa revealed that all the herbal supplements, except silymarin, induced apoptosis, with quercetin being the most potent (3x increase compared with control). Furthermore, ginseng and curcumin were region-specific in inducing apoptosis. The ability of quercetin and curcumin to modulate ACFs correlates well with their ability to induce apoptosis. Western blot analysis of caspase 9, Bax (proapoptotic) and Bcl-2 (antiapoptotic) proteins from the colon scraping suggests that quercetin and curcumin induce apoptosis via the mitochondrial pathway. Taken together, the results of this study suggest that these herbal supplements may exert significant and potentially beneficial effects on decreasing the amount of precancerous lesions and inducing apoptosis in the large intestine.

Animals↗

In vitro pollen tube growth reveals the cytotoxic potential of the flavonols, quercetin and rutin.

Flavonols are phytochemicals widely found in commonly consumed foods. In spite of their beneficial effects on human health, however, cytotoxicity and even suspected genotoxicity have also been reported for the flavonol, quercetin. This points to the need for preventive studies to identify any cytotoxic effects associated with pure flavonol intake. This work was performed with the aim of verifying whether a plant-based in vitro system, the pollen tube, could be used to evaluate the cytotoxic potential of exogenous flavonols. Increasing concentrations of the aglycone, quercetin, and its glycoside, rutin, were assayed with regard to tube growth of kiwifruit pollen, determined by applying the pollen tube growth test protocol. This test, based on the photometric quantification of pollen tube mass production in suspension cultures, has already been applied in the sensitive and reliable toxicological evaluation of a wide range of chemicals. Whereas 60-800 microM rutin promoted kiwifruit pollen tube elongation, 10-50 microM quercetin strongly inhibited growth, and also produced irreversible malformations, such as screw-like tube growth, abnormal vacuolation, alteration of organelle streaming, and nuclear positioning. Thus, the cytotoxic potentials of the two flavonols have been confirmed to differ. Pollen tubes seem to afford a promising test system for a preventive, rapid in vitro biosafety assessment of antioxidant nutritional supplements, without using laboratory animals.

Actinidia↗

Protection by the flavonoids myricetin, quercetin, and rutin against hydrogen peroxide-induced DNA damage in Caco-2 and Hep G2 cells.

Flavonoids are reported to exhibit a wide variety of biological effects, including antioxidant and free radical-scavenging activities. Reactive oxygen species have been implicated in a range of human pathological diseases such as atherosclerosis and certain cancers. The aims of this present study were 1) to investigate the effect of the flavonoids myricetin, quercetin, and rutin on cell viability, endogenous antioxidant enzyme activities, and DNA integrity in Caco-2 and Hep G2 cells and 2) to determine whether these flavonoids could protect against H2O2-induced DNA damage. Both cell lines were supplemented with various concentrations (0-200 microM) of myricetin, quercetin, and rutin for 24 hours or H2O2 (50 microM) for 30 minutes, and cell viability was assessed. Over the concentration range tested, neither the flavonoids nor H2O2 significantly affected cell viability. The effect of the flavonoids on the activities of the antioxidant enzymes catalase (EC 1.11.1.6) and superoxide dismutase (EC 1.15.1.1) and on DNA integrity was assessed. The flavonoids did not significantly affect catalase or superoxide dismutase activity and did not induce DNA damage in either cell line. Exposure to 50 microM H2O2 for 30 minutes at 37 degrees C resulted in significant DNA damage, and preincubation with the flavonoids before H2O2 exposure significantly (p < 0.05) protected Caco-2 and Hep G2 cells against H2O2-induced DNA damage.

Animals↗

Anti- and pro-oxidant activity of rutin and quercetin derivatives.

Some semi-synthetic flavonoids, particularly derivatives of rutin, are used as therapeutic agents in the treatment of diseases involving free radicals. Here, for the first time, a complete study has been made of the relationship between the structure of such molecules and their superoxide, hydroxyl and peroxyl radical scavenging activity. The molecules chosen for this study were rutin, its aglycone (quercetin), and their methyl ethyl and hydroxyl-ethyl derivatives. Our results are consistent with the general agreement on the structural requirements for free radical scavenging activity. Moreover, we have shown that alkylation of the hydroxyl in position 7 enhanced the scavenging, and also that in a Fenton reaction system, some quercetin derivatives with free catechol moiety or free hydroxyl in position 3 (or both) were pro-oxidant, through superoxide radical and hydrogen peroxide production. Although the structural features needed for pro-oxidant activity are not entirely clear, it appears that to avoid pro-oxidant behaviour, the hydroxyl group in position 3 should be blocked to prevent its auto-oxidation. Thus, flavonoids cannot only be considered purely as antioxidants, since under certain reaction conditions they can also display pro-oxidant activity. This unexpected behaviour could explain, in part, the observed toxicity of some flavonoids in-vivo.

Antioxidants↗

Use of rutin for medical management of idiopathic chylothorax in four cats.

Four cats with idiopathic chylothorax were given rutin. Three of the 4 cats had clinical improvement, and complete resolution of chylous effusion was evident in 2 cats. Idiopathic chylothorax in cats is a condition that may be difficult to resolve with medical or surgical treatment. Currently, thoracic duct ligation is considered the preferred technique, but expense and a guarded prognosis for resolution may make this procedure undesirable to cat owners. Rutin administration may offer an alternative to traditional treatments or may be useful as an adjunctive treatment.

Animals↗

[Hypocholesterolemic effect of naringin and rutin flavonoids].

Flavonoids are pigments fenolics of plants that possess several biological activities, and many of these are associated with prevention of chronic diseases as cancer and hyperlipidemia. This work had as objective evaluates the effect of the flavonoids naringin and rutin on the metabolism lipidic of chicks hypercholesterolemic. In agreement with the results it can be observed that naringin and rutin reduced the levels of total cholesterol significantly, cholesterol-LDL, cholesterol-VLDL and triglycerols, not presenting, however, reductions in the levels of cholesterol-HDL.

Animals↗

[Determination of syringin and rutin in 11 species of Saussurea by high performance liquid chromatography].

Zorbax ODS column and gradient elution of acetonitrile-acetic acid solution as mobile phase were employed to determine the content of syringin and rutin in 11 species of Saussurea by RP-HPLC. The detection wavelength was 260 nm. The results showed that standard curves of syringin and rutin were linear in the range of 0.0525 microgram-1.05 micrograms and 0.0658 microgram-1.32 micrograms, respectively. The correlation coefficients were 0.9988 and 0.9999. The method provides new indices for quality control of Saussurea.

Chromatography, High Pressure Liquid↗

[Quantitative analysis of rutin and vitamin C by NIR FTIR].

In this paper, near-infrared diffuse reflectance spectroscopy(NIRDRS) method was used as a quantitative tool to measure the solid mixture of rutin and vitamin C by collecting NIR spectra in the range 7,000-3,900 cm-1. The quantitative mathematics model was established with partial least squares(PLS) method. The correlation coefficient was 99.75%, the standard error of Rutin was 0.363%, and the standard error of Vitamin C was 1.078%. The methods are rapid, exact and nondestructive to samples. The components of the samples can be individually analyzed with high accuracy and precision, so NIRDRS can be a useful method of quality control of pharmaceuticals in the future.

Ascorbic Acid↗

[Research concerning rutin semisynthetic derivatives, synthesis and pharmaco-toxicological properties of some new morpholine and piperidine derivatives].

In order to continue the research of the rutin semisynthetic derivatives we obtained some new morpholine and piperidine derivatives. Melting points, solubility, yield, C, H, N elemental analysis and UV spectra characterised all of these compounds. The toxicity was established by intraperitoneal administration at mice; the values of LD50 are between 743.75 and 856.25 mg/kg (medium toxicity). Pharmacological assays included the following parameters: leukocytes formula, NBT test, and serum complement activity. The new derivatives of rutin have a very good solubility in water, a pH closed to physiological value and immunosuppressive activity: peripheric blood PMN and lymphocytes are decreased; fagocytic capacity of peripheric blood PMN is also decreased; serum complement activity is not changed.

Animals↗

Determination of free radical scavenging activity of quercetin, rutin, luteolin and apigenin in H2O2-treated human ML cells K562.

We investigated protective effects of four flavonoids against H2O2- induced DNA damage in human myelogenous leukemia cells (K562) using the comet assay. The structural difference of studied flavonoids -- quercetin, rutin, luteolin and apigenin -- are characterized by the number of hydroxyl groups on the B ring. The presence of an o-dihydroxy structure on the B-ring confers a higher degree of stability to the flavonoid phenoxyl radicals by participating in electron delocalization and is, therefore, an important determinant for antioxidative potential. The results correlate with earlier published data obtained in murine leukemia cell line L1210. Hydrogen peroxide induced in human K562 cells a concentration-dependent increase of single cell DNA strand breaks. The strongest inhibition against H2O2-induced DNA damage (44%, 42%) was found in a range of luteolin and quercetin concentrations of 20-100 micromol/l. Protective effect of rutin (100 and 1000 micromol/l) was only marginal (8-10%). Apigenin had no protective effect on DNA single strand breaks induced by H2O2. Luteolin and quercetin are therefore effective in the protection of human single cell DNA from oxidative attack.

Apigenin↗

Validation assay for total flavonoids, as rutin equivalents, from Trichilia catigua Adr. Juss (Meliaceae) and Ptychopetalum olacoides Bentham (Olacaceae) commercial extract.

An ultraviolet spectrophotometric method was validated for total flavonoid quantitation, as rutin equivalents, present in the Trichilia catigua Adr. Juss (Meliaceae) and Ptychopetalum olacoides Bentham (Olacaceae) commercial extract. Parameters as linearity, interval (range), specificity, estimated limit of detection (LOD, microg/mL), estimated limit of quantitation (LOQ, microg/mL), recovery (R, %), precision or relative standard deviation (RSD, %), and accuracy (E, %) were established. The analytical method was validated according to the experimental results: correlation coefficient (r = 0.9997); interval (RSD = 0.15-0.47%; E = 98.98-101.24%); specificity to total flavonoids quantitation, as rutin equivalents, at wavelength 361.0 nm; LOD = 0.09 microg/mL and LOQ = 0.27 microg/mL; R = 99.36-102.14%; adequate intra- and interrun precision (0.30-0.49% and 0.31-0.81%), and intra- and interrun accuracy (100.60-102.38% and 98.58-100.38%).

Calibration↗