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PubMedDate not supplied

UV spectrophotometric determination of bioflavonoids from a semisolid pharmaceutical dosage form containing Trichilia catigua Adr. Juss and Ptychopetalum olacoides Bentham standardized extract: analytical method validation and statistical procedures.

A precise, accurate, and sensitive UV spectrophotometric method was developed and validated for routine quantification of total bioflavonoids, expressed as rutin, from a topical oil-in-water pharmaceutical emulsion containing the extract of Trichilia catigua Adr. Juss and Ptychopetalum olacoides Bentham. The method was validated experimentally, and the data were treated rigorously by statistical analysis. The following analytical parameters were assessed: linearity, specificity, intra- and interrun precision measured as relative standard deviation (RSD, %), intra- and interrun accuracy (E, %), recovery (Rec., %), limit of detection (LOD, microg/mL), and limit of quantification (LOQ, microg/mL). The UV spectrophotometric method was linear (r = 0.9995) for standard rutin over the concentration range of 5.0-15.0 microg/mL with specificity for total bioflavonoids (expressed as rutin) at 361.0 nm with an absence of interferents from the complex matrix; RSD of < or = 1.79%, intrarun (E = 97.88 +/- 1.75 to 99.0 +/- 0.33%) and interrun (E = 98.38 +/- 1.12 to 100.79 +/- 1.30%) accuracy; Rec. = 98.64 +/- 0.42 to 100.74 +/- 0.41%; LOD = 0.20 microg/mL; and LOQ = 0.30 microg/mL.

Administration, Topical↗

PubMed1980

[Antiexudative effect of naringin in experimental pulmonary edema and peritonitis].

The authors examined antiexudative activity of bioflavonoids naringin and rutin in comparative aspect in two models of acute inflammation. The experiments were carried out on 180 male white rats and 24 guinea pigs. The two flavonoids manifested marked antiexudative effect in rats with experiments peritonitis, induced by the model of U. M. Teotino et al. ED50 of naringin was 200 mg per kg after oral administration, but of rutin-260 mg per kg. In the same model ED50 of naringin was 67 mg per kg of body weight after intramuscular administration. In rats and guinea pigs with experimental lung oedema naringin, used in a dose of 200 mg per kg intraperitoneally two hours before injection of edemogenous substance (a water solution of ammonium chloride), reduced lethality with 57,4% in rats and with 37% in guinea pigs, but rutin-with 50% and 25% respectively. The examined substances were used in doses, presenting 10% of DL50. There was no statistically significant difference in respect to their antiexudative activity.

Animals↗

PubMed1996

High-performance liquid chromatography/continuous-flow liquid secondary ion mass spectrometry of flavonoid glycosides in leguminous plant extracts.

A method for the identification of flavonoid glycosides utilizing continuous-flow liquid secondary ion mass spectrometry (CF-LSIMS) is presented. Minimum detectable quantities (MDQs) were determined for three model flavonoid glycosides (rutin, naringin and esculin) by both positive ion direct insertion probe (DIP)-LSIMS (1.6 nmol, 1.7 nmol and 730 pmol, respectively) and positive ion CF-LSIMS (330 pmol, 340 pmol and 290 pmol, respectively). Optimization of CF-LSIMS instrumental parameters was performed using the model compound rutin. Parameters optimized included mobile phase composition, glycerol concentration, mobile phase flow rate, ion source temperature, acceleration lens potential (amplitude and polarity) and Cs+ primary ion energy. Final instrumental optimization yielded an MDQ of 1.0 ng (1.6 pmol) for rutin by flow-injection CF-LSIMS. The optimization parameters were utilized in the identification of flavonoid glucosides in alfalfa (Medicago sativa L) and chickpea (Cicer arietinum) extracts by high-performance liquid chromatogrphy/CF-LSIMS. The results support the controversial identification of a major extract component as formononetin-7-O-glucoside-6"-malonate as opposed to afrormosin-7-O-glucoside-6"-malonate.

Chromatography, High Pressure Liquid↗

PubMed1990

Type-II estrogen binding sites in a lymphoblastoid cell line and growth-inhibitory effect of estrogen, anti-estrogen and bioflavonoids.

Type-II estrogen-binding sites (type-II EBS) have been demonstrated in the human lymphoblastoid cell line IM-9 using a whole-cell assay with (6,7-3H) estradiol (3H-E2) as tracer. Competition analysis showed that the anti-estrogen tamoxifen and the flavonoids quercetin and rutin competed for (3H)-E2 binding to type-II EBS. Growth experiments demonstrated that diethylstilbestrol (DES) tamoxifen (TAM), quercetin and rutin exerted a reversible dose-dependent inhibition of cell proliferation in the range of concentrations between 10 nM and 10 microM. The relative binding affinity of quercetin, rutin, DES and TAM for type-II EBS correlated well with their potency as cell growth inhibitors. Moreover, hesperidin, a flavonoid which does not bind to type-II EBS, was ineffective in inhibiting cell growth. Cell-cycle analysis showed that the growth-inhibitory effect of DES, TAM or quercetin was due to a blocking effect in the G0-G1 phases. Our results suggest that high estrogen and anti-estrogen concentrations and flavonoids may regulate IM-9 cell growth through a common mechanism involving a binding interaction with type-II EBS.

Binding, Competitive↗

PubMed1998

Intestinal bacterial metabolism of flavonoids and its relation to some biological activities.

Flavonoid glycosides were metabolized to phenolic acids via aglycones by human intestinal microflora producing alpha-rhamnosidase, exo-beta-glucosidase, endo-beta-glucosidase and/or beta-glucuronidase. Rutin, hesperidin, naringin and poncirin were transformed to their aglycones by the bacteria producing alpha-rhamnosidase and beta-glucosidase or endo-beta-glucosidase, and baicalin, puerarin and daidzin were transformed to their aglycones by the bacteria producing beta-glucuronidase, C-glycosidase and beta-glycosidase, respectively. Anti-platelet activity and cytotoxicity of the metabolites of flavonoid glycosides by human intestinal bacteria were more effective than those of the parental compounds. 3,4-Dihydroxyphenylacetic acid and 4-hydroxyl-phenylacetic acid were more effective than rutin and quercetin on anti-platelet aggregation activity. 2,4,6-Trihydroxybenzaldehyde, quercetin and ponciretin were more effective than rutin and ponciretin on the cytotoxicity for tumor cell lines. We insist that these flavonoid glycosides should be natural prodrugs.

Bacteria↗

PubMed2005

A comparison between hairy root cultures and wild plants of Saussurea involucrata in phenylpropanoids production.

Saussurea involucrata is an important medicinal plant that produces a few bioactive secondary metabolites, such as hispidulin, rutin, and syringin. Previously, we established a hairy root culture system for this species through Agrobacterium-mediated transformation. The present study addressed the issue as how hairy root cultures perform in phenylpronoid accumulation. From the ethanolic extract of a hairy root culture established for Saussurea involucrata, syringin, rutin and hispidulin, were isolated and their chemical structures were confirmed by HPLC-ESI-MS. A quantitative study of the compounds showed great levels of syringin and hispidulin (being 43.5+/-1.13 and 0.34+/-0.023 mg g-1 dry weight, respectively), about 40 and 3 times, respectively, higher than those from wild plants. But, the levels of rutin from hairy roots were much lower (0.71+/-0.043 vs. 6.59+/-0.56 mg g-1 dry weight). Compared with untransformed root cultures, syringin and hispidulin levels were also higher. An experiment on culture media showed that MS was superior to others for phenylpropanoids accumulation in hairy roots, a 28-day culture produced 405 mg l-1 syringin.

Chromatography, High Pressure Liquid↗

PubMed2005

Are chemical compounds important for soybean resistance to Anticarsia gemmatalis?

The identification and quantification of flavonoids (rutin and genistin) present in extracts of soybean genotypes, and their effects on the biology and physiology of Anticarsia gemmatalis Hübner (Lep.: Noctuidae) were studied. Analysis of covariance and bicoordinate utilization plots were used to remove the effect of feeding time from pupal weight and consumption as well as to separate pre- and postingestive effects of treatment on A. gemmatalis growth. Genotypes PI 274454, PI 227687, and "IAC-100" extracts in general, caused higher mortality, negatively influenced initial larval and pupal weight, and elongated larval cycle. Larvae fed on the "IAC-100" extract diet ingested larger amounts of food per unit of time, but were less efficient in its conversion to biomass. Leaf extracts of PI 227687 had the largest concentration of rutin (quercitin 3-O-rhamnosylglucoside), followed by PI 274454, and "IAC-100"; PI 74454 also had the highest genistin (genistein 7-O-glucoside) content. The susceptible cultivar "BR-16" showed only a kaempferol-based flavonoid in its chemical profile, indicating that after successive crosses, secondary compounds responsible for plant defenses were eliminated. Genotypes PI 274454, PI 227687, and "IAC-100" showed accentuated resistance characteristics and were considered inadequate sources for the development of A. gemmatalis. Considering rutin and genistin concentration in these genotypes, it is suggested that flavonoids are important factors conferring resistance to A. gemmatalis.

Animals↗

PubMed1985

Actions of flavonoids and the novel anti-inflammatory flavone, hypolaetin-8-glucoside, on prostaglandin biosynthesis and inactivation.

The newly identified plant-derived flavone-glycoside hypolaetin-8-glucoside, which has anti-inflammatory and gastric ulcer protective properties, and its corresponding aglycone, hypolaetin, were tested for effects on prostaglandin biosynthesis and degradation. They were compared with four other flavonoids, viz. rutin and its corresponding aglycone, quercetin, and the aglycones isoscutellarein and kaempferol. Over the range 10-1000 microM the glycosides rutin and hypolaetin-8-glucoside stimulated prostaglandin formation by sheep seminal vesicle microsomes incubated with radiolabelled arachidonic acid; the other compounds were essentially inactive. Over 5-5000 microM rutin and hypolaetin-8-glucoside enhanced the release of prostacyclin (and other prostanoids) from fragments of rat caecum incubated in the absence of additional arachidonic acid; the four aglycones compounds did not stimulate prostacyclin release but some reduced it at 5000 microM. However, the glycosides did not affect the enzymatic inactivation of radiolabelled prostaglandin F2 alpha by semi-purified bovine lung prostaglandin 15-hydroxydehydrogenase (PGDH) or in 100,000 g supernatants prepared from homogenised rat stomach. Three of the four aglycones (quercetin, kaempferol, isoscutellarein, in descending order of potency) were inhibitory to PGDH with ID50 values in the range 130-2100 microM. The results show that the capacity of flavonoids to enhance prostaglandin formation is associated with the presence of glycosidic substitution, whereas PGDH inhibition requires its absence. The relevance of this biochemical profile of hypolaetin-8-glucoside to its anti-inflammatory gastroprotective effects in vivo is discussed.

Animals↗

PubMed1990

Flavonoids as superoxide scavengers and antioxidants.

The superoxide anions scavenging activity and antioxidation of seven flavonoids--quercetin, rutin, morin, acacetin, hispidulin, hesperidin, and naringin--were studied. The superoxide anions were generated in a phenazin methosulphate-NADH system and were assayed by reduction of nitroblue tetrazolium. The scavenging activity ranked: rutin was the strongest, and quercetin and naringin the second, while morin and hispidulin were very weak. The concentration values yielding 50% inhibition of lipid peroxidation in mouse liver homogenate were in order of 10(-6) M for quercetin, rutin, and morin; and of 10(-5) M for acacetin and hispidulin, while naringin and hesperidin had no antioxidative action. In comparison with the antioxidative and scavenging activities of flavonoids, there are no correlations.

Animals↗

PubMed1992

Quercetin prevents the cytotoxicity of oxidized LDL on lymphoid cell lines.

Low-density lipoproteins oxidized by ultraviolet radiations constitute a useful model system for studying their cytotoxic effect on cultured cells. Polyphenolic flavonoids were able to inhibit the peroxidation of low-density lipoproteins (IC50; 10-20 microM for quercetin or rutin) and their subsequent cytotoxicity. The inhibition of the cytotoxic effect was well correlated with that of TBARS formation. Our most important and novel conclusion is that quercetin and rutin are able to prevent directly at the cellular level the cytotoxic effect of oxidized LDL, since cells preincubated with polyphenolic flavonoids were protected against the cytotoxic effect of previously oxidized low-density lipoprotein (IC50; 0.1 and 3 microM with quercetin and rutin, respectively). In contrast, flavone was completely inefficient. In conclusion polyphenolic flavonoids can protect cells against the injury due to oxidation of low-density lipoproteins by constituting two lines of defence: (1) at high concentrations, antioxidant effect inhibiting the lipoprotein oxidation and the subsequent cytotoxicity; (2) at low concentrations, direct protection of cells against the cytotoxic effect of oxidized low-density lipoproteins.

Arteriosclerosis↗

PubMed2005

Resveratrol and curcumin reduce the respiratory burst of Chlamydia-primed THP-1 cells.

The intracellular bacterium Chlamydia pneumoniae is involved in the inflammation process of atherosclerosis. We previously demonstrated that C. pneumonia infected monocytes (THP-1 cells) responded to stimulation by an increased respiratory burst linked to an increased NADPH oxidase (NOX) activity. We now tested agents acting on the assembly of the NOX subunits or on protein kinase C, a trigger of NOX activity. Apocynin, resveratrol, rutin, quercetin, curcumin, and tocopherols were tested. The cells were pre-incubated with Chlamydia and the agent for 19 h, and then stimulated with phorbol myristate acetate. The NOX activity was monitored by measuring the hydrogen peroxide production. Resveratrol and curcumin (10(-4)-10(-6) M) were better inhibitors than apocynin. alpha-Tocopherol was inactive, and gamma-tocopherol inhibitor at 10(-4) M only. Quercetin was inactive, and rutin a moderate but significant inhibitor. The inhibition by resveratrol was increased by 10(-6) M rutin or quercetin. Resveratrol and curcumin thus appeared to be interesting for atherosclerosis treatment.

Antioxidants↗

PubMed2006

Application of reverse-flow micellar electrokinetic chromatography for the simultaneous determination of flavonols and terpene trilactones in Ginkgo biloba dosage forms.

A reverse-flow micellar electrokinetic chromatographic (RF-MEKC) method was developed for the simultaneous qualitative determination of 10 components consisting of the flavonol glycosides, rutin and quercitrin, the flavonol aglycones, isorhamnetin, kaempferol and quercetin, the terpene trilactones, ginkgolides A, B, C and J and the sesquiterpene, bilobalide. This method was used to fingerprint Ginkgo biloba solid oral dosage forms and validated for the quantitation of the marker compounds, rutin and quercetin in some commercial products. In addition to the usual variables, the influence of some essential background electrolyte (BGE) components such as sodium dodecyl sulphate (SDS) and -cyclodextrin concentrations were investigated. A polyimide fused-silica square capillary column (75 microm I.D. x 360 microm O.D.) with a total length of 60.0 cm and effective length of 45.0 cm was used for the separation. The final BGE consisted of 20 mM phosphoric acid, 40 mM SDS and 12 mM -cyclodextrin (pH 2.2) using reverse polarity with a voltage of -17.5 kV. Samples were injected electrokinetically at -5 kV for 3 s for the qualitative analysis and hydrodynamically at 20 mbar for 0.6 s for the quantitative assay. The total run time was 22 min and the limits of detection were 3.13 microg/ml and 1.88 microg/ml for rutin and quercetin, respectively. Fingerprint profiles of the solid oral dosage forms and the results of the quantitative analysis indicated that there were major discrepancies in the marker content between products and illustrates the value of this method for use as a procedure to assess product quality of commercially available Ginkgo biloba products.

Chromatography, Micellar Electrokinetic Capillary↗

PubMed2005

Anti-inflammatory effect of Ruta graveolens L. in murine macrophage cells.

Ruta graveolens L. (Rutaceae) is used for several therapeutic purposes worldwide. The present study is designed to investigate the effect of plant extract of Ruta graveolens on murine macrophage cells (J-774) challenged with lipopolysaccharide (LPS). LPS induces inflammatory response by stimulating the production of nitric oxide and other mediators. Significant inhibition (p=0.01 to p<0.002) of the LPS-induced nitric oxide production was observed in cells treated with plant extract in a concentration dependent manner. The inhibition observed for the extract was significantly higher than that observed for rutin, a flavonoid constituent of the plant. At 40 microM rutin, a comparable concentration of this flavonoid in the highest concentration (500 microg/ml) of plant extract was used in this study; a 20% inhibition (p=0.058) was observed. Inhibition in inducible nitric oxide synthase (inos) gene expression in the cells treated with the plant extract suggests an inhibition at the transcription level. Interestingly, a concomitant decrease in transcription of cyclooxygenase-2 (COX-2) gene has also been observed in cells treated with the plant extract and this inhibition is significantly higher than that observed with the highest concentration of rutin (80 microM) used in the study. As an inflammatory response, upregulation of nitric oxide synthase (iNOS) and COX-2 enzymes leads to production of pro-inflammatory mediators, namely nitric oxide and prostaglandins, respectively. Hence, the significant inhibitory effects on both of these inflammatory mediators unravel a novel anti-inflammatory action of this plant.

Animals↗

PubMed1982

The influence of food flavonoids on the activity of some hepatic microsomal monooxygenases in rats.

The effects of several food flavonoids on the activities of some drug-metabolizing enzymes in rat-liver microsomes were determined in vivo. When quercetin, chrysin, hesperetin and (+)-catechin were injected ip at doses of 150 mg/kg body weight/day for 3 days, quercetin and chrysin stimulated aminopyrine demethylase. When quercetin, rutin, hesperetin and (+)-catechin were fed as components (0 . 1%) of purified diets administered to rats for 4 wk, rutin and (+)-catechin increased microsomal cytochrome b5 levels and quercetin and (+)-catechin increased aminopyrine demethylase activity. On the other hand rutin, quercetin and hesperetin inhibited NADH-cytochrome c reductase. Aniline hydroxylase was not affected by any of the flavonoids administered by either route. The results show that each flavonoid affects different components of the monooxygenase system. The fact that some flavonoids give different effects according to the route and/or the duration of administration is discussed.

Animals↗

PubMed2000

Antibacterial and allelopathic activity of extract from Castanea sativa leaves.

Following the extraction of Castanea sativa with an aqueous solution of sulfuric acid (pH 3.0), the ethyl acetate soluble fraction was tested for its antibacterial and allelopathic activity. The extract was shown to have pronounced antibacterial effects against seven of the eight strains of Gram-positive and Gram-negative bacteria used (MIC in the range of 64-256 microg/ml and MBC in the range of 256-512 microg/ml). The active fraction was analyzed by TLC and HPLC showing the presence of rutin, hesperidin, quercetin, apigenin, morin, naringin, galangin and kaempferol. Standards of the identified flavonoids were tested against the same bacterial strains. The highest activity was shown by quercetin, rutin and apigenin. The allelopathic effect was tested against Raphanus sativus seed germination. The extract, quercetin, rutin and apigenin caused a decrease in the percentage of seed germination and root and epicotyl growth.

Anti-Bacterial Agents↗

PubMed2001

Common phytochemicals are ecdysteroid agonists and antagonists: a possible evolutionary link between vertebrate and invertebrate steroid hormones.

Many plant compounds are able to modulate growth and reproduction of herbivores by directly interacting with steroid hormone systems. In insects, several classes of phytochemicals, including the phytoestrogens, interfere with molting and reproduction. We investigated whether the anti-ecdysone activity may be due to interaction with the ecdysone receptor (EcR) using a reporter-gene assay and a cell differentiation assay of an ecdysone-responsive cell line, Cl.8+. We tested rutin (delays molt in insects); four flavones: luteolin and quercetin (metabolites of rutin), and apigenin and chrysin; and three non-flavones, coumestrol and genistein (both estrogenic) and tomatine (alters molt in insects). None of the phytochemicals tested were ecdysone agonists in the reporter-gene assay, but the flavones were able to significantly inhibit EcR-dependent gene transcription. In the Cl.8+ cells, quercetin and coumestrol were mixed agonists/antagonists, while genistein, tomatine and apigenin showed a synergistic effect with ecdysteroid in the reduction of cell growth. We suggest that the rutin effects on molting in insects are most likely due to the metabolites, luteolin or quercetin, while tomatine acts via a non-EcR pathway. Flavones not only interact with EcR and estrogen receptor (ER), but also signal nitrogen-fixing bacteria to form root nodules. The NodD protein which regulates this symbiosis has two ligand-binding domains similar to human ERalpha. The evolutionary significance of these findings are discussed.

Animals↗

PubMed2003

Characterization and content of flavonoid glycosides in genetically modified tomato (Lycopersicon esculentum) fruits.

There is a growing interest in producing food plants with increased amounts of flavonoids because of their potential health benefits. Tomatoes contain small amounts of flavonoids, most of which are located in the peel of the fruit. It has been shown that flavonoid accumulation in tomato flesh, and hence an overall increase in flavonoid levels in tomato fruit, can be achieved by means of simultaneous overexpression of the maize transcription factors LC and C1. Fruit from progeny of two modified lines (2027 and 2059) was selected for a detailed analysis and individual identification of flavonoids, at different stages of maturity. Nine major flavonoids were detected in the flesh of transgenic ripe tomatoes. LC/NMR, LC/MS, and LC/MS/MS enabled us to identify these as kaempferol-3,7-di-O-glucoside (1), kaempferol-3-O-rutinoside-7-O-glucoside (2), two dihydrokaempferol-O-hexosides (3 and 4), rutin (5), kaempferol-3-O-rutinoside (6), kaempferol-3-O-glucoside (7), naringenin-7-O-glucoside (8) and naringenin chalcone (9), which were quantified by HPLC/DAD. All but 5, 6, and 9 were detected in tomato for the first time. The total flavonoid glycoside content of ripe transgenic tomatoes of line 2059 was about 10-fold higher than that of the controls, and kaempferol glycosides accounted for 60% of this. Kaempferol glycosides comprised around 5% of the flavonoid glycoside content of ripe control tomatoes (the rest was rutin and naringenin chalcone). The rutin concentration in both transgenic and control fruits was similar.

Chromatography, High Pressure Liquid↗

PubMed2005

Content of chalconaringenin and chlorogenic acid in cherry tomatoes is strongly reduced during postharvest ripening.

The contents of chalconaringenin, chlorogenic acid, rutin, ascorbic acid, lycopene, and beta-carotene were analyzed during postharvest and vine ripening of cherry tomatoes (Lycopersicon esculentumMill.) (cv. Jennita) produced in a greenhouse. A remarkable decrease in the content of chalconaringenin took place during postharvest ripening. The tomatoes were found to contain 15.26 mg 100 g(-1) fresh weight (FW) at harvest but held only 0.41 mg after 3 weeks at 20 degrees C in darkness. Chalconaringenin did not convert into naringenin. The content of chlorogenic acid fell from 0.51 to 0.06 mg 100 g(-1) FW at the same conditions. The content of rutin and that of total phenolics remained stable during postharvest ripening. The amounts of lycopene as well as beta-carotene and ascorbic acid increased during postharvest ripening. No significant change in the amount of methanol soluble antioxidants or total soluble solids was found during postharvest ripening of the tomato fruits. During vine ripening, the total amount of phenolics and that of soluble solids (% Brix) increased. The content of phenolics correlated well with the content of methanol soluble antioxidants (p < 0.001). The amount of ascorbic acid increased from 9.7 mg in green-yellow tomatoes to 17.1 mg 100 g(-1) FW in red tomatoes. The amount of chalconaringenin decreased to 8.16 mg 100 g(-1) FW, whereas no significant change was observed for chlorogenic acid or rutin. Possible causes for the decrease in chalconaringenin are discussed.

Ascorbic Acid↗