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PubMed1988

Interaction of flavonoid compounds with contractile proteins of skeletal muscle.

Flavonoids (quercetin, rutin) influence ATPase activity and actomyosin superprecipitation. Low concentrations (below 20 mumol/l) of flavonoids were found to cause conformational changes in the myosin structure accompanied by an increase in ATPase activity. At higher concentrations an inhibitory action of flavonoids on both ATPase activity and actomyosin superprecipitation occurred. Conformational changes are likely to be due to flavonoids binding to regulatory site near the active centre of the myosin head. The effect of quercetin was stronger than that of rutin.

Actomyosin↗

PubMedDate not supplied

Antiaggregatory effects of flavonoids in vivo and their influence on lipoxygenase and cyclooxygenase in vitro.

Quercetin, rutin and troxerutin were found to inhibit platelet aggregation on collagen strip superfused with blood of anesthetized cats. Quercetin was the most potent acting at the dose of 1 micrograms/kg. Its effect was shortlasting. Troxerutin was a weak inhibitor of platelet aggregation and its effect was delayed. Quercetin inhibited in 50% 15-lipoxygenase and 12-lipoxygenase in vitro at the concentration of 1.3 microm and 13 microM respectively. It stimulated cyclooxygenase when 100 microM of arachidonic acid was applied. Quercetin inhibited cyclooxygenase in the presence of 1.6 microM of substrate. Rutin was a weaker inhibitor of lipoxygenase. Troxerutin was inactive in all experiments in vitro. It is concluded that unusually strong effect of quercetin in vivo can be explained neither by its influence on cyclooxygenase nor on lipoxygenase because the effects in vitro were observed in much higher concentrations.

Animals↗

PubMed1976

Studies on Vaccinium myrtillus anthocyanosides. I. Vasoprotective and antiinflammatory activity.

A Vaccinium myrtillus anthocyanosides preparation (equivalent to 25% of anthocyanidins) demonstrated significant vasoprotective and antioedema properties in exerimental animals. In rabbits, the skin capillary permeability increase, due to chloroform, was reduced both after i.p. (25--100 mg/kg) and oral administration (200--400 mg/kg) of anthocyanosides. Their activity was more lasting in comparison to rutin or mepyramine and this did not seem to be due to a specific antagonism towards inflammatory process mediators such as histamine or bradykinin. Experiments carried out in rats demonstrated that Vacinium myrtillus anthocyanosides were effective both in skin capillary permeability test as well as on vascular resistance of rats fed a P factor deficient diet. In the former test effective doses were in the range of 25--100 mg/kg (by oral route). In both the animal species investigated, anthocyanosides were two-fold more active when compared to the flavonoid rutin. Vaccinium myrtillus anthocyanosides by oral route inhibited carrageein paw oedema in rats showing a dose-response relationship. An antioedema activity was detected also after i.v. or topical application.

Animals↗

PubMedDate not supplied

[Effect of aluminum poisoning and gamma-irradiation on the antioxidant system of the body and study of possibilities for correction].

The influence of selenium and rutin on the antioxidant protection system of the organisms in connection with Al-intoxication and gamma-irradiation was investigated. It has been determined that selenium increases the antioxidant protection caused by aluminium. Under simultaneous action of aluminium and gamma-irradiation upon the organism selenium stimulated accumulation of toxic lipids peroxide oxidation products. Rutin action in the situations under investigation caused weakening of antioxidant protection.

Aluminum↗

PubMed1993

Type II estrogen binding sites and antiproliferative activity of quercetin in human meningiomas.

Eleven cases of meningiomas were investigated for the presence of estrogen and progesterone receptors. These tumors specifically bound estradiol. This binding activity almost exclusively resulted from the presence of high numbers of type II estrogen binding sites (EBS). Estrogen receptors were absent or present at low concentrations. Competition analysis showed that the flavonoid, quercetin, competed for tritiated estradiol binding to type II EBS; both rutin and hesperidin did not. In addition, 10 microM quercetin, unlike rutin or hesperidin, was effective in inhibiting in vitro bromodeoxyuridine incorporation by meningioma cells. Although the mechanism of the antiproliferative activity of quercetin remains to be clarified, it is possible that this flavonoid may regulate cell growth through a ligand interaction with type II EBS.

Adult↗

PubMed2003

Effect of diluting agent on sensitivity in capillary electrophoresis with amperometric detection.

Besides the running buffer, pH of buffer, separation voltage and sampling time, the diluting agent was studied in this paper as one of the important factors influencing the sensitivity in capillary electrophoresis (CE) with amperometric detection (AD) when electrokinectic sampling was used. Clonidine hydrochloride, hydrochlorothiazide and rutin, which are positively charged, neutral and negatively charged, respectively, in aqueous solutions, could be perfectly separated by CE with 25 mmol x L(-1) Na(2)B(4)O(7) - 50 mmol x L(-1) NaH(2)PO(4) as running buffer and detected by measuring their current responses with AD. Before CE running, some kinds of diluents including water, methanol, formamide, running buffer, hydrochloric acid and sodium hydroxide were, respectively, applied to dilute the stock solutions of above three analytes and their effects on the sensitivity of CE-AD were investigated. The results showed that for electrokinetic injection, the current responses of these three analytes were greatly affected in different ways when different diluting agents were used. This method was applied to simultaneously determine the active ingredients in one Chinese compound hypotensor named Zhen Ju Jiang Ya Pian, in which the contents of clonidine hydrochloride, hydrochlorothiazide and rutin is very different as 0.03 mg : 5 mg : 20 mg per tablet, and satisfactory results were obtained by adjusting their sensitivity by selecting the suitable diluting agent.

Buffers↗

PubMed2003

Quantitative analysis of aglycone quercetin in mulberry leaves (Morus alba L.) by capillary zone electrophoresis.

A capillary zone electrophoresis method was established for analysis of aglycone quercetin in mulberry leaves (Morus alba L.). The influence of, e.g., background electrolyte concentrations and pH, surfactant concentrations, organic solvents, temperature, and voltage on the separation of aglycone quercetin, rutin, quercitrin, kaempferol, catechin, and gallic acid was systematically investigated. The optimum condition providing baseline separation of all compounds within 16.5 min was obtained in 150 mM boric acid (pH 10.0) using a fused-silica capillary with an effective length of 42.5 cm (50 microm inner diameter), temperature of 32 degrees C, and voltage of 15 kV. Method assessment was performed by standard addition method using rutin as an internal standard. Linearity of the method was excellent (r(2) > 0.999) over the concentration tested (40-160 microg/mL). The relative standard deviations (%RSDs) from injection, intraday, and interday precision were less than 2.5%. Recoveries were good (asymptotically equal to 100.0%,%RSD = 0.8%) with a limit of detection (LOD) and limit of quantitation (LOQ) of 0.86 and 3.16 microg/mL (%RSD = 1.8%), respectively. The aglycone quercetin found in the mulberry leaves was 0.452 g/100 g (%RSD = 0.6%) on dry weight.

Electrophoresis, Capillary↗

PubMed2002

Food-derived polyphenols inhibit pancreatic cancer growth through mitochondrial cytochrome C release and apoptosis.

There is increasing evidence that food-derived polyphenols have a beneficial effect for cancers. Our purpose was to determine the effect and mechanism of action of these compounds on pancreatic cancer. We measured effects of quercetin on pancreatic cancer in a nude mouse model. We also investigated the effects of quercetin, rutin, trans-resveratrol and genistein on apoptosis and underlying signaling in pancreatic carcinoma cells in vitro. Quercetin decreased primary tumor growth, increased apoptosis and prevented metastasis in a model of pancreatic cancer. In vitro quercetin and trans-resveratrol, but not rutin, markedly enhanced apoptosis, causing mitochondrial depolarization and cytochrome c release followed by caspase-3 activation. In addition, the effect of a combination of quercetin and trans-resveratrol on mitochondrial cytochrome c release and caspase-3 activity was greater than the expected additive response. The inhibition of mitochondrial permeability transition prevented cytochrome c release, caspase-3 activation and apoptosis caused by polyphenols. Nuclear factor-kappa B activity was inhibited by quercetin and trans-resveratrol, but not genistein, indicating that this transcription factor is not the only mediator of the polyphenols' effects on apoptosis. The results suggest that food-derived polyphenols inhibit pancreatic cancer growth and prevent metastasis by inducing mitochondrial dysfunction, resulting in cytochrome c release, caspase activation and apoptosis.

Animals↗

PubMed2005

Comparison of the 2,2'-azinobis-3-ethylbenzotiazo-line-6-sulfonic acid (ABTS) and ferric reducing anti-oxidant power (FRAP) methods to asses the total antioxidant capacity in extracts of fruit and vegetables.

A comparison was made on the use of two spectrophotometric methods, the ferric reducing antioxidant power (FRAP) method and the 2,2'-azinobis-3-ethylbenzotiazoline-6-sulfonic acid (ABTS) method, for the measurement of the total antioxidant capacity (TAC) of plant foods. The correlations of TAC measured by the two methods were highly significant in both water-soluble (r2= 0.90) and water-insoluble extracts (r2= 0.98) from 13 strawberry samples. Also a corresponding comparison of TAC in extracts from 14 plant species showed high correlation coefficients, r2= 0.98 for water-soluble extracts and r2= 0.88 for water-insoluble extracts. The ratio of TAC values obtained with the two methods (ABTS/FRAP) varied between 0.7 and 3.3 for different plant extracts indicating that they contained antioxidants with varying reactivity in the two methods. TACs in six pure antioxidant substances were ranked in the following order by both methods: quercetin > ferulic acid > catechin > rutin > caffeic acid > Trolox = chlorogenic acid. The two methods showed similar TAC values for quercetin, rutin, caffeic acid and chlorogenic acid while ferulic acid and catechin gave higher results with the ABTS method than with the FRAP method, and such differences probably explain the varying ratios of ABTS/FRAP obtained in foods. Regarding storage TAC in water-soluble strawberry extracts stored at -20 or -80 degrees C was stable for at least five months while storage at 4 degrees C decreased the TAC value with 40% during five weeks of storage. The study showed that both the ABTS and FRAP methods can be used for convenient monitoring of the antioxidant capacities in fruit and vegetables, and that different antioxidants had varying reactivity in the two methods.

Antioxidants↗

PubMed2006

Antioxidants from Rabdosia japonica.

The antioxidant activities of phenolic compounds: pedalitin, quercetin, rutin, isoquercitrin, and rosmarinic acid, isolated from the dried leaves of Rabdosia japonica Hara (Labiatae) were elucidated. All the phenolics tested exhibited superoxide scavenging activity and an inhibitory effect on xanthine oxidase (EC 1.1.3.22), and pedalitin showed the most potent antioxidant activity. Pedalitin prevents the generation of superoxide radicals in part by inhibiting xanthine oxidase competitively. Both pedalitin and quercetin inhibited uric acid formation by xanthine oxidase, and the inhibition kinetics analysed by Lineweaver-Burk plots found both flavonoids to be competitive inhibitors. On the other hand, isoquercitrin, rutin and rosmarinic acid were effective in scavenging superoxide radicals generated by the xanthine-xanthine oxidase system without inhibiting the enzyme.

Antioxidants↗

PubMed1977

[Isolation and identification of flavon(ol)-O-glycosides in caraway (Carum carvi L.), fennel (Foeniculum vulgare Mill.), anise (Pimpinella anisum L.), and coriander (Coriandrum sativum L.), and of flavon-C-glycosides in anise. I. Phenolics of spices (author's transl)].

The flavonoid constituents of various spices were separated by means of chromatography on cellulose colums, and the following compounds were obtained crystalline: Quercetin 3-glucuronide from caraway, fennel, anise, and coriander; isoquercitrin from caraway and fennel; rutin from fennel and anise; quercetin 3-O-caffeylglucoside and kaempferol 3-glucoside from caraway; quercetin 3-arabinoside from fennel, and luteolin 7-glucoside, isoorientin and isovitexin from anise. Other constitutents which were however not obtained crystalline, but which could be identified by the usual procedures were kaempferol 3-glucuronide and kaempferol 3-arabinoside in fennel, apigenin 7-glucoside and a luteolin glycoside in anise, and isoquercitrin and rutin in coriander. The glycosides contained in the fruit of the four spices also occur in the leaves. Leaves of caraway and fennel in addition contain isorhammetin glycosides in low concentration.

Condiments↗

PubMed1989

Flavones and flavonol glycosides from Eupatorium cannabinum L.

The 6-methoxyflavones hispidulin and eupafolin have been identified for the first time from the aerial parts of Eupatorium cannabinum L. The presence of the previously known flavonol glycosides astragalin, kaempferol-3-rutinoside, hyperoside, isoquercitrin and rutin could be confirmed. Hispidulin, eupafolin and rutin were screened for cytotoxicity in vitro.

Animals↗

PubMed2005

Hepatoprotective effect of flavonol glycosides rich fraction from Egyptian Vicia calcarata Desf. against CCl4-induced liver damage in rats.

The hepatoprotective activity of flavonol glycosides rich fraction (F-2), prepared from 70% alcohol extract of the aerial parts of V. calcarata Desf., was evaluated in a rat model with a liver injury induced by daily oral administration of CCl4 (100 mg/kg, b.w) for four weeks. Treatment of the animals with F-2 using a dose of (25 mg/kg, b.w) during the induction of hepatic damage by CCl4 significantly reduced the indices of liver injuries. The hepatoprotective effects of F-2 significantly reduced the elevated levels of the following serum enzymes: alanine aminotransferase (ALT), aspartate aminotransferase (AST), alkaline phosphatase (ALP) and lactate dehydrogenase (LDH). The antioxidant activity of F-2 markedly ameliorated the antioxidant parameters including glutathione (GSH) content, glutathione peroxidase (GSH-Px), superoxide dismutase (SOD), plasma catalase (CAT) and packed erythrocytes glucose-6-phosphate dehydrogenase (G6PDH) to be comparable with normal control levels. In addition, it normalized liver malondialdehyde (MDA) levels and creatinine concentration. Chromatographic purification of F-2 resulted in the isolation of two flavonol glycosides that rarely occur in the plant kingdom, identified as quercetin-3, 5-di-O-beta-D-diglucoside (5) and kaempferol-3, 5-di-O-beta-D-diglucoside (4) in addition to the three known compounds identified as quercetin-3-O-alpha-L-rhamnosyl- (1-->6)-beta-D-glucoside [rutin, 3], quercetin-3-O-beta-D-glucoside [isoquercitrin, 2] and kaempferol-3-O-beta-D-glucoside [astragalin, 1]. These compounds were identified based on interpretation of their physical, chemical, and spectral data. Moreover, the spectrophotometric estimation of the flavonoids content revealed that the aerial parts of the plant contain an appreciable amount of flavonoids (0.89%) calculated as rutin. The data obtained from this study revealed that the flavonol glycosides of F-2 protect the rat liver from hepatic damage induced by CCl4 through inhibition of lipid peroxidation caused by CCl4 reactive free radicals.

Animals↗

PubMed1984

Flavonoid inhibition of human basophil histamine release stimulated by various agents.

Eleven naturally occurring flavonoids representing five different chemical classes were studied for their effects on human basophil histamine release triggered by six different stimuli. The flavonoids included flavone, quercetin, taxifolin, chalcone, apigenin, fisetin, rutin, phloretin, tangeretin, hesperetin, and naringin. The stimuli were antigen, anti-IgE, concanavalin A, ionophore A23187, formylmethionylleucylphenylalanine, and tetradecanoyl phorbol acetate. Concentration-effect relationships were established for each flavonoid (5-50 microM) at concentrations of stimuli which produced near optimal histamine release. Variable degrees of inhibition were noted depending on the nature of the stimulus and flavonoid structure. The flavonols, quercetin and fisetin, and the flavone, apigenin, exhibited a predilection to inhibit histamine release stimulated by IgE-dependent ligands (antigen, anti-IgE, and con A). The flavanone derivatives, taxifolin and hesperetin, were inactive, as were the glycosides, rutin and naringin. The open chain congeners, chalcone and phloretin, also possessed inhibitory activity. Thus, the flavonoids may be useful probes in comparative analysis of secretory phenomena. The findings suggest that the biochemical pathways leading to secretion differ subtly from one stimulus to another. The differences are detectable with flavonoids of different structures and possibly reflect distinct pathways of Ca2+ mobilization or other unique mechanisms of action.

Arachidonic Acid↗

PubMed1987

Effects of tobacco glycoprotein (TGP) on the immune system. III. The effect of aging on the mitogenic response of human peripheral blood lymphocytes to TGP.

We have shown that the mitogenic response of human peripheral blood lymphocytes (PBL) to tobacco glycoprotein (TGP), a glycoprotein rich in rutin or rutinlike polyphenol moieties, which is isolated from cured tobacco leaves, does not decrease with age. In contrast, the proliferative response to lipopolysaccharide (LPS) tends to decline with age, and a significant decrease is observed in the mitogenic response to rutin-bovine serum albumin (R-BSA). LPS and R-BSA are similar in some aspects to TGP, the former in that TGP and LPS are both T-independent B-cell mitogens for mice and are both highly negatively charged, and the latter in that covalently bound polyphenol groups are present on both R-BSA and TGP. Although the kinetics of the mitogenic responses to these three mitogens are similar (T. Francus, R. F. Klein, L. Staiano-Coico, G. W. Siskind, and C. G. Becker, Effects of tobacco glycoprotein (TGP) on the immune system. II. TGP is a mitogen for human peripheral blood lymphocytes. Submitted for publication.), multiple regression analyses show no correlation in the mitogenic responses of PBL from young donors to TGP and LPS, to TGP and R-BSA, or to LPS and R-BSA. In contrast, there are significant correlations between the proliferative responses to these mitogens by PBL from old donors. The results suggest that only a small subpopulation of the cells which are stimulated by R-BSA and LPS are not altered with age, and these are most likely the cells that are stimulated by the three mitogens studied.

Adult↗

PubMed1986

Effects of flavonoids on enzyme secretion and endocytosis in normal and mucolipidosis II fibroblasts.

The effect of flavonoids on beta-hexosaminidase transport and endocytosis has been studied in cultured human skin fibroblasts. In mucolipidosis II fibroblast cultures, characterized by their preferential secretion of most newly synthesized hydrolases, quercetin and phloretin (200 microM) inhibited beta-hexosaminidase synthesis as well as total culture-associated enzyme activity. Taxifolin induced a 2.4-fold increase in the total enzyme activity without altering the intra- and extracellular distribution of the enzyme. Rutin, although less effective, also stimulated an overall increase in total enzyme. The flavonoid effects were all concentration-dependent. Very little effect was observed in either the distribution or the total beta-hexosaminidase activity in normal fibroblast cultures. Taxifolin and hesperitin inhibited receptor-mediated endocytosis of beta-hexosaminidase by fibroblasts up to 50% of control uptake. Naringin, quercetin, and phloretin moderately inhibited uptake by 30% while rutin and fisetin had no effect. The results demonstrate that certain naturally occurring flavonoids affect the secretion of lysosomal enzymes as well as their endocytosis by fibroblasts. Since most individuals ingest up to one gram per day of these substances, flavonoids may prove to have significant effects on normal lysosomal enzyme physiology.

Acetylglucosaminidase↗

PubMed1986

Heterogeneous effect of flavonoids on K+ loss and lipid peroxidation induced by oxygen-free radicals in human red cells.

Treatment of fresh erythrocytes with phenazine methosulfate, an intracellular generator of oxygen-free radicals, and diethyldithiocarbamate an inhibitor of superoxide dismutase results in membrane damage consisting in lipid peroxidation and increase in passive K+ permeability. Various flavonoids which have previously been reported to act as oxygen-free radical scavengers were tested on this erythrocyte model. Surprisingly, flavonoids did not exhibit the same effect on the oxygen free radical-stimulated K+ permeability. It was possible to classify these agents into four groups: protective (those decreasing the oxygen-free radical-stimulated K+ permeability): kaempferol, naringenin, apigenin, naringin; toxic (those increasing the deleterious effect of oxygen-free radicals): myricetin, delphinidin, quercetin; biphasic effective (characterized by opposite effects depending on the concentration): phloretin, cyanin, catechin, morin and inactive: rutin, phloridzin. In addition, a similar classification was observed when membrane lipid peroxidation was examined, i.e. kaempferol decreased lipid peroxide formation whereas myricetin enhanced it, morin exhibited a biphasic effect and rutin has no effect. The previously reported metal chelating effect of flavonoids could not totally explain the protective effect of kaempferol as was demonstrated by the partial protective effect exhibited by desferrioxamine. Moreover, this study suggests that a generation of oxygen-free radicals in red cells induced a K+ loss which probably results from membrane lipid peroxidation.

Cell Membrane Permeability↗

PubMed1989

Modifying role of dietary factors on the mutagenicity of aflatoxin B1: in vitro effect of plant flavonoids.

Eighteen flavonoids have been tested for their ability to inhibit the mutagenicity of aflatoxin B1 (AFB1) towards strains TA100 and TA98 of Salmonella typhimurium provided with a rat liver activation system. These flavonoids belong to 5 different groups: flavone, isoflavone, flavanone, flavanol and flavonol, and many individual members are natural products present in edible portions of a variety of food plants. Several flavonoids exhibited significant inhibitory ability in both strains. Flavonols in general are more active in this regard, while flavanones show a strain-specific response. The flavanol group of compounds did not display any activity. Among the most effective flavonoids are kaempferol, morin, fisetin, biochanin A and the glycoside rutin, all of which exhibit a dose-dependent inhibition pattern. Kaempferol and rutin, in particular, show exceptional activity inasmuch as, on a molar basis, only a 10-fold excess dose of each can inhibit the mutagenic activity of AFB1 in strain TA98 by 50%. The action of flavonoids is possibly mediated through interaction with microsomal activating enzymes. Previous evidence from this laboratory about their inhibitory action on DNA-adduct formation and metabolic activation together with the present results suggests that certain flavonoids, notably polyhydroxylated flavonols, may have potential anticarcinogenic activity against AFB1.

Aflatoxin B1↗