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PubMed2002

[Synthesis of hirsutrin and hyperin]

OBJECTIVE: To investigate an easier method for preparation of hirsutrin and hyperin. METHODS: Rutin was utilized as the starting material. The target compounds were produced via benzoylation, hydrolysis, glycosidation and deproteination. RESULTS: The yield of key intermediate 5,7,3',4'-tetra-O-benzoyl quercetin was improved by reducing the hydrolysis time of 5,7,3',4'-tetra-O-benzoyl rutin in HCl/EtOH. Hirsutrin and hyperin were synthesized. CONCLSION: Hirsutrin can be synthesized and the yield of hyperin improved by this method.

Journal Article↗

PubMed2006

[Human pregnane X receptor-mediated transcriptional regulation of cytochrome P450 3A4 by some phytochemicals].

OBJECTIVE: To test the effect on human pregnane X receptor (hPXR)-mediated transcription regulation of CYP3A4 by five selected phytochemicals. METHODS: Transient cotransfection reporter gene assays in HepG(2) cells were performed with the hPXR expression plasmid and the reporter gene plasmid which contains XRE in the promoter of CYP3A4 linked to luciferase. RESULTS: In the dose-effect study, soybean isoflavone, luteolin and curcumin induced the CYP3A4 transcription via PXR in an evident dose-dependent manner, but isorhamnetin and rutin did not. The inducibility of soybean isoflavone, luteolin and curcumin was also increased in concentrations between 1 micromol/L and 50 micromol/L, 24 h after induction, 50 micromol/L soybean isoflavone, luteolin and curcumin exhibited a 5.46-fold, 2.87-fold, and 2.07-fold increase respectively, compared with 0.1% DMSO treated cells. In the time-effect study, 10 micromol/L and 50 micromol/L soybean isoflavone, luteolin and curcumin induced CYP3A4 transcription between 12 h and 48 h, the strongest induction appeared in 48 h. 48 h after induction, 50 micromol/L soybean isoflavone, luteolin and curcumin exhibited a 6.72-fold, 3.24-fold, and 2.13-fold increase respectively, compared with 0.1% DMSO treated cells. CONCLUSION: Three phytochemicals, i.e. soybean isoflavone, luteolin and curcumin stimulate the PXR-mediated transcription of CYP3A4. Isorhamnetin and rutin have no effect on the CYP3A4 transcription via PXR.

Carcinoma, Hepatocellular↗

PubMed2001

Oxidation of lovastatin in the solid state and its stabilization with natural antioxidants.

Oxidative instability of the hydroxy methylglutaryl Co-A reductase inhibitor lovastatin in the solid state and stabilization with natural antioxidants (ascorbic acid, rutin, gallic acid, quercetin and caffeic acid) was investigated. Lovastatin in the solid state and binary mixtures with 10% (w/w), 25% (n/n), 12.5% (n/n) and 6.3% (n/n) of each of the antioxidants were prepared. Oxidation experiments were performed on the scanning calorimeter using dynamic oxygen atmosphere. The amount of non-oxidized lovastatin was determined using HPLC. The results of the experiments have shown that lovastatin is unstable to oxidation under higher temperatures and in the presence of oxygen, and that some antioxidants markedly stabilize the drug. The most significant antioxidative effect was seen with caffeic acid and rutin, followed by gallic acid and quercetin. Ascorbic acid was only moderately effective. The results prove that flavonoids do have significant antioxidative potential. This phenomenon can be used to improve oxidative stability of drugs such as lovastatin which are sensitive to the presence of oxygen.

Anticholesteremic Agents↗

PubMed2001

[Determination of polyphenols in tobacco by solid phase extraction and high performance liquid chromatography].

A high performance liquid chromatographic (HPLC) method for the determination of polyphenols in tobacco was studied. Polyphenols can be extracted from tobacco sample by refluxing with 80% (volume fraction) methanol, then subjected to degrease by solid phase extraction with Sep-Pak-C18 column. Chlorogenic acid, rutin, scopoletin, caffeic acid, scopolin and other polyphenols can be separated on a Nova-Pak-C18 column (3.9 mm i.d. x 150 mm) gradiently eluted with methanol and 0.05 mol.L-1 potassium dihydrogen phosphate buffer solution as mobile phase at a flow-rate of 0.5 mL.min-1. Polyphenols were determined at the maximum wavelength of each polyphenol, for chlorogenic acid 326.1 nm, rutin 354.8 nm, scopoletin 344.0 nm, caffeic acid 323.7 nm and scopolin 365.2 nm by photodiode array detector. The main polyphenols in tobacco can be identified with UV spectroscopy. The recoveries of tobacco polyphenols were 94%-105%, and the relative standard deviations were 1.28%-1.49%. This method can be applied to the determination of polyphenols in tobacco with satisfactory results.

Chromatography, High Pressure Liquid↗

PubMed2003

[HPLC analysis of main flavonoid chemicals and their spatio-temporal dynamics in Bt transgenic cotton].

Flavonoids are important chemicals of resistance to pests in cotton plant. The main flavonoid chemicals and their spatio-temporal dynamics of content in Bt transgenic cotton were tested by HPLC. The results showed that the flavonoid chemicals of resistance to pests mainly including rutin, isoquercitrin and quercetin could be detected and quantitatively analyzed by HPLC. The contents of rutin, isoquercitrin and quercetin were the highest in petal, but lower in calyx, bract and cotton boll. Moreover, the total content of flavonoid chemicals in top leaf was much higher at developmental stage than at seedling stage. The content of each flavonoid chemicals of resistance to pests was different during different developmental stage and in different organs. It was indicated that different flavonoid chemicals played different roles in resistance to pests.

Bacillus thuringiensis↗

PubMed2003

St. John's wort extracts and some of their constituents potently inhibit ultimate carcinogen formation from benzo[a]pyrene-7,8-dihydrodiol by human CYP1A1.

Commercially available St. John's wort (Hypericum perforatum) preparations and some of their main constituents (hypericin, pseudohypericin, hyperforin, rutin, and quercetin) were examined for their potential to inhibit carcinogen activation by human cytochrome P450 1A1 (CYP1A1). We used a reconstituted system consisting of purified human CYP1A1, purified human NADPH-cytochrome P450 reductase, and dilaurylphosphatidylcholine as lipid component. St. John's wort extracts potently inhibited CYP1A1-catalyzed (+/-)-trans-7,8-dihydro-7,8-dihydroxy-benzo(a)pyrene (7,8-diol-B[a]P) epoxidation, the terminal reaction leading to the ultimate carcinogenic product (+/-)-B[a]P-r-7,t-8-dihydrodiol-t-9,10-epoxide (diolepoxide 2). All constituents, except rutin, were shown to possess strong inhibitory potencies toward diolepoxide 2 formation from 7,8-diol-B[a]P, with IC(50) values of 0.5 microM (hypericin), 1.2 microM (hyperforin), 1.5 microM (quercetin), and 8 microM (pseudohypericin), respectively. Preincubation experiments revealed that their action was not mechanism based. Inhibition kinetics studies showed the anthrodianthrone compound hypericin to be a noncompetitive inhibitor, with a K(i) value of 0.6 microM, and the phloroglucinol hyperforin to be a competitive inhibitor, with a K(i) value of 1.1 microM. When the effects on NADPH-P450 reductase activity were investigated, all constituents of St. John's wort studied turned out to be rather ineffective inhibitors; quercetin was the only exception, with an IC(50) value of approximately 20 microM. These in vitro data indicate that St. John's wort extracts and some of their constituents potently inhibit the major human procarcinogen-activating enzyme CYP1A1.

Animals↗

PubMed2004

[HPLC investigation of antioxidant components in Solidago herba].

Representatives of Solidago species have been used in European phytotheraphy for centuries as a component of urological and antiphlogistical remedies. Solidago canadensis L. (Asteraceae) contains a wide range of active ingredients, such as flavonoids, saponins, hydroxycinnamates and mineral elements, which are responsible for its characteristic anti-inflammatory, spasmolytic and diuretic properties. Quality control of collected Solidaginis herba were performed according to the instructions of the X. German Pharmacopoea, while different LC-MS technologies were applied to evaluate the exact phenoloid composition. Three flavonol aglycons (quercetin, kaempferol and isorhamnetin) connected to several sugar components (glucose, rhamnose, galactose and rutinose), caffeoylquinic acid and a caffeoyl-shikimic acid glycoside were identified in the samples. Quercetin-3-O-beta-glucoside (isoquercitrin), quercetin-3-O-beta-galactoside (hyperoside), quercetin-3-O-beta-rhamnoside (quercitrin), quercetin-3-O-beta-rutinoside (rutin), kaempferol-3-O-beta-rhamnoside (afzelin), kaempferol-3-O-beta-rutinoside (nicotiflorin), caffeoil-quinic acid (chlorogenic acid) were identified in sample "A", while the presence of quercetin, quercetin-3-O-beta-glucoside (isoquercitrin), quercetin-3-/6"-O-acetyl-/-beta-glucopiranoside, quercetin-3-O-beta-rutinoside (rutin), kaempferol, kaempferol-3-O-beta-glucoside (astragalin), kaempferol-3-/6"-O-acetyl-/-beta-glucopiranoside, isorhamnetin, isorhamnetin-3-/6"-O-acetyl-/-beta-glucopiranoside, isorhamnetin-3-O-beta-rutinoside (narcissin), caffeoil-quinic acid (chlorogenic acid), caffeoil-shikimic acid-glucoside (dattelic acid-glucoside) were confirmed in sample "B". According to the occurrence of acetyl-glycosides and the diversity of sugar component of flavonoid glycosides Solidaginis herba samples chemotaxonomically were classified into different varieties. Incidence of acetyl-glycosidic flavonoids and absence of flavonoid galactosides and rhamnosides in the sample "B" together give support for the taxonomic recognition of varietases Solidago canadensis L. var. canadensis and var. scabra. Sample "A" was identified as Solidago canadensis L. var. canadensis, while sample "B" has proved to be belong to variety Solidago canadensis L. var. scabra. Due to the same flavonoid aglycons and the large amounts of flavonol glycosides occurring in each drug, phytochemical characteristics of investigated samples proved to be very similar.

Antioxidants↗

PubMed1990

[Several years observation of a Catergen (cyanidanol-3) induced immunohemolysis].

A report is presented on repeated severe episodes of cyanidanol-induced immune hemolysis in a 75-year-old woman suffering from chronic active hepatitis. One year after the first hemolytic episode, high titers of anticyanidanol antibodies were still demonstrated in the patient's serum (as well as sensitization of the patient's lymphocytes by the drug). 4 years later virtually no decrease of the antibody titer was found. Further investigations of the patient's serum revealed antibodies against flavonoids with free hydroxyl groups (cyanidanol and rutin). However, no antibodies against flavonoids with derivatized hydroxyl groups (troxerutin, mixture of hydroxy-ethyl-rutin and silibinin) could be demonstrated. Sensitization with flavonoids other than cyanidanol preceding cyanidanol-induced hemolysis has been proposed by others. In this case storage of approximately 75 flavonoid containing preparations in a chemist's shop in the patient's house may have contributed to the astonishing persistence of dry dependent antibodies.

Aged↗

PubMedDate not supplied

[Flavonoids as medicines].

Although flavonoids have been used for a long time, many medical practitioners and pharmacists know very little about them. This article gives a few particulars of some flavonoids and plant extracts: rutin, water soluble derivatives of rutin, citroflavonoids, anthrocyanins, procyanidins, silymarin, Ginkgo biloba, Chrysanthellum indicum and Lespedeza capitata.

Animals↗

PubMed1985

Effects of hypolaetin-8-glucoside and related flavonoids on soybean lipoxygenase and snake venom phospholipase A2.

Hypolaetin-8-glucoside, a novel flavonoid isolated from Sideritis mugronensis and possessing anti-inflammatory and gastroprotective properties in the rat, was compared with the structurally related flavonoids hypolaetin, isoscutellarein, rutin, quercetin and kaempferol for inhibitory effects on the enzymes soybean 15-lipoxygenase and snake venom phospholipase A2. The aglycone flavonoids dose-dependently inhibited snake venom phospholipase A2 but the glycosides hypolaetin-8-glucoside and rutin were inactive. All 6 flavonoids inhibited soybean 15-lipoxygenase with no differences between glycosides and aglycones, although flavonols appeared more active than flavones. The inhibition of these enzyme activities cannot explain the anti-inflammatory action of hypolaetin-8-glucoside, unless a significant proportion of the drug reaches the target tissue as the aglycone, hypolaetin.

Animals↗

PubMed1978

On the vascular action of crataemon.

The vascular action of crataemon is studied. The effect of the drug on organ blood flow is examined using isotope methods. It is established that under conditions of blood loss, 10 mg/kg crataemon sharply inceases the blood supply to the myocardium and liver. Under the same conditions the blood flow in the kidneys and intestines decreases after administration of the drug. Its effect is weaker in case of normal blood pressure. In the case of perfusion of cat hind legs the flavonoid mixture studied has a biphasic effect manifested in the form of initial brief hypertension, followed by a more prolonged and stronger depressor reaction. In larger oral doses (100 and 200 mg/kg) crataemon increases the resistance of the capillaries and decreases capillary permeability in albino rats. The experiments carried out confirm the predominantly action of crataemon on some vascular regions (heart and liver). It has biphasic effect on peripheral vessels, which may be attributed to the presence of different components. The capillary-tonic action is most probably due to the presence of rutin and rutin-like flavonoids.

Animals↗

PubMed1995

Myocardial effects of flavonoids from Crataegus species.

The influence of the main flavonoids from Crataegus species (hawthorn, Rosaceae) on coronary flow, heart rate and left ventricular pressure as well as on the velocity of contraction and relaxation was investigated in Langendorff perfused isolated guinea pig hearts at a constant pressure of 70 cmH2O. Drug action was evaluated in a concentration range of 10(-7) to 5 x 10(-4) mol/l. An increase of coronary flow caused by the O-glycosides luteolin-7-glucoside (186%), hyperoside (66%) and rutin (66%) as well as an increase of the relaxation velocity (positive lusitropism) by luteolin-7-glucoside (104%), hyperoside (62%) and rutin (73%) were the major effects observed at a maximum concentration of 0.5 mmol/l. Furthermore, slight positive inotropic effects and a rise in heart rate were seen. Similar but less intensive actions were found with the C-glycosides vitexin, vitexin-rhamnoside and monoacetyl-vitexin-rhamnoside. Possible beta-adrenergic activities of the flavonoids could be excluded by the addition of propranolol in fixed concentrations of 10(-8) to 10(-5) mol/l. Moreover, pretreatment of the animals with reserpine (7 mg/kg) did not influence myocardial activity of hyperoside (10(-4) mol/l). As previous experiments showed an inhibition of the 3',5'-cyclic adenosine monophosphate phosphodiesterase, the results suggest an inhibition of this enzyme as the possible underlying mechanism of cardiac action of flavonoids from Crataegus species.

3',5'-Cyclic-AMP Phosphodiesterases↗

PubMed1994

Inhibition of lipoperoxidation of linoleic acid by five antioxidants of different lipophilicity.

The efficacy of oxidation inhibition of five natural and synthetic antioxidants (BHT, BHA, nordihydroguaiaretic acid (NDGA), quercetin and rutin) was studied in O/W emulsions. Linoleic acid was used as a reference molecule; the reaction was initiated by an azo-compound. The kAH characterizing the reaction of the antioxidant with the peroxyl radical decreases in the following order: kAH(BHA) > kAH(BHT) > kAH(NDGA) > kAH(quercetin) > kAH(rutin).

Antioxidants↗

PubMed1997

Effect of flavonoids on daunomycin-induced toxicity in cultivated endothelial cells.

The cytotoxicity of daunomycin in cultivated endothelial cells was differentially influenced by selected flavonoids. One group (myricetin, flavone, apigenin) enhanced daunomycin toxicity whereas flavonols like quercetin, kaempferol, rutin and morin significantly inhibited this cytotoxicity. Other flavonoids like hesperidin, naringin and catechin did not interact with the daunomycin-induced inhibition of proliferation. There was no correlation between lipophilicity and toxicity of the flavonoids and the observed effects on daunomycin-induced cytotoxity. The protective effect of quercetin and rutin seems to be connected with the antioxidative properties of these flanonols.

Animals↗

PubMed1998

Effects of selected flavonoids on deformability, osmotic fragility and aggregation of human erythrocytes.

The effects of 8 selected flavonoids of deformability, osmotic fragility and dextran-induced aggregation of human erythrocytes were studied. The following flavonoids were found to protect against loss of filterability (deformability) through 5 microns diameter pores of erythrocytes dehydrated with calcium ionophore A23187 (1.9 mumol/l): apigenin > quercetin > cirsimaritin > rutin > luteolin > chrysoeriol-4'-O-glucoside > 3,5,7-trihydroxy 4'-methoxy flavone 7-rutinoside, whereas beta-naphtho flavone enhanced the loss of filterability. When the potassium ionophore valinomycin (18 mumol/l) was used to induce cell dehydration, the order of potency of the flavonoids in protecting against loss of filterability was apigenin > cirsimaritin = chrysoeriol-4'-O-glucoside > 3,5,7-trihydroxy 4'-methoxy flavone 7-rutinoside > luteolin = rutin > quercetin, whereas beta-naphtho flavone again enhanced the loss of filterability. All flavonoids reduced ESR measured over 1 h except for 3,5,7-trihydroxy 4'-methoxy flavone 7-rutinoside which showed no effect, and for quercetin which significantly enhanced ESR. All flavonoids also improved erythrocyte osmotic fragility except for apigenin which significantly increased osmotic fragility. These effects were explained in terms of the number and location of hydroxyl groups on the basic skeleton of flavone. The results suggest that the presence of an OH and C5 is essential for the described rheological effects of these flavonoids.

Adult↗

PubMed2000

Antiinflammatory activity of extracts and fractions from the leaves of Gochnatia polymorpha.

The aqueous and ethanol extracts from the leaves of Gochnatia polymorpha and further fractions obtained from the latter extract using solvents with increasing polarity, including its aqueous residue and the amino acid, 4-hydroxy-N-methyl-proline were investigated by carrageenin-induced pedal oedema formation. It was shown that the aqueous and ethanol extracts and the ethyl acetate fraction demonstrated significant antiinflammatory activity. The chemical investigation of the latter fraction revealed the presence of caffeic acid, chlorogenic acid, 3-0-methylquercetin, hyperosid and rutin. The amino acid 4-hydroxy-N-methyl-proline, a nonprotein amino acid that has not been reported before in the Asteraceae was isolated as a major compound and identified by spectroscopic methods.

Analgesics↗

PubMed2001

Transcellular transport of genistein, a soybean-derived isoflavone, across human colon carcinoma cell line (Caco-2).

Genistein, a soybean-derived isoflavone, is thought to have an anticarcinogenic action, but little is known about the cellular mechanisms of its intestinal absorption. This study was designed to investigate the absorption mechanisms of genistein using human colon carcinoma cell line, Caco-2 cells. The apical-to-basolateral transcellular transport of genistein across a Caco-2 cell monolayer was significantly greater than that in the opposite direction. An uptake experiment revealed that cellular uptake of genistein by Caco-2 cells was concentrative. The transcellular transport of genistein was saturable and temperature-dependent, and was inhibited by other flavonoids such as rutin, quercetin, (+)-catechin and (-)-epicatechin. These results suggest that genistein is transported across Caco-2 cells by a carrier-mediated system, located on the apical membrane.

Antineoplastic Agents↗

PubMedDate not supplied

Chemiluminescence determination of pharmacologically active compounds by capillary electrophoresis.

A simple and rapid capillary electrophoresis with direct chemiluminescence method has been developed for the determination of five natural pharmacologically active compounds including rutin, protocatechuic aldehyde, chlorogenic acid, luteolin and protocatechuic acid. The luminol as a component of the separation electrolyte buffer was introduced at the head of the separation capillary. The separation of five compounds was carried out in a fused-silica capillary with 15.0 mmol/L tetraborate, 1.0 mmol/L SDS and 0.42 mmol/L luminol (pH 8.5). The analytes was determined by enhancing the chemiluminescence of luminol with 0.13 mmol/L K3Fe(CN)6 in 0.05 mol/L NaOH, which was introduced at the post-column stage. The voltage applied was 16 kV. Under the optimum conditions, the analytes were separated within 10 min. The excellent linearity was obtained over two to three orders of magnitude with a detection limit (signal:noise = 3) of 0.012-0.055 micromol/L for all five analytes. The method was successfully used in the analysis of pharmaceutical and biological samples, and the assay results were satisfactory.

Benzaldehydes↗