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Antihyperlipidemic effect of hydroalcoholic extract, and polyphenolic fraction from Dracocephalum kotschyi Boiss.

Blood lipid levels in rats with hyperlipidemia resulting from high-fat feeding were determined after oral administration of hydroalcoholic extract and polyphenolic fraction of Dracocephalum kotschyi leaves. Administration of the hydroalcoholic extract and polyphenolic fraction produced a significant decrease of blood triglyceride, total cholesterol and LDL-cholesterol levels. HDL-cholesterol level was significantly increased.

Administration, Oral↗

Antioxidative polyphenols from walnuts (Juglans regia L.).

Three hydrolyzable tannins, glansrins A-C, together with adenosine, adenine, and 13 known tannins were isolated from the n-BuOH extract of walnuts (the seeds of Juglans regia L.). Glansrins A-C were characterized as ellagitannins with a tergalloyl group, or related polyphenolic acyl group, based on spectral and chemical evidence. The 14 walnut polyphenols had superoxide dismutase (SOD)-like activity with EC(50) 21.4-190 microM and a remarkable radical scavenging effect against 1,1-diphenyl-2-picrylhydrazyl (DPPH) (EC(50) 0.34-4.72 microM).

Biphenyl Compounds↗

Sodium sulphite inhibition of potato and cherry polyphenolics in nucleic acid extraction for virus detection by RT-PCR.

Phenolic compounds from plant tissues inhibit reverse transcription-polymerase chain reaction (RT-PCR). Multiple-step protocols using several additives to inhibit polyphenolic compounds during nucleic acid extraction are common, but time consuming and laborious. The current research highlights that the inclusion of 0.65 to 0.70% of sodium sulphite in the extraction buffer minimizes the pigmentation of nucleic acid extracts and improves the RT-PCR detection of Potato virus Y (PVY) and Potato leafroll virus (PLRV) in potato (Solanum tuberosum) tubers and Prune dwarf virus (PDV) and Prunus necrotic ringspot virus (PNRSV) in leaves and bark in the sweet cherry (Prunus avium) tree. Substituting sodium sulphite in the nucleic acid extraction buffer eliminated the use of proteinase K during extraction. Reagents phosphate buffered saline (PBS)-Tween 20 and polyvinylpyrrolidone (PVP) were also no longer required during RT or PCR phase. The resultant nucleic acid extracts were suitable for both duplex and multiplex RT-PCR. This simple and less expensive nucleic acid extraction protocol has proved very effective for potato cv. Russet Norkotah, which contains a high amount of polyphenolics. Comparing commercially available RNA extraction kits (Catrimox and RNeasy), the sodium sulphite based extraction protocol yielded two to three times higher amounts of RNA, while maintaining comparable virus detection by RT-PCR. The sodium sulphite based extraction protocol was equally effective in potato tubers, and in leaves and bark from the cherry tree.

Flavonoids↗

In situ ageing of fine beech roots (Fagus sylvatica) assessed by transmission electron microscopy and electron energy loss spectroscopy: description of microsites and evolution of polyphenolic substances.

Root biomass is quantitatively and qualitatively important in most ecosystems, but its contribution to the pool of organic matter in the soil is not clear. This work was designed to specify root ageing on an ultrastructural scale by transmission electron microscopy combined with microanalysis by electron energy loss spectroscopy. This approach is very suitable for studying the soil/plant interface, and for semi-quantitative analysis of the evolution of polyphenolic substances during root evolution. Three root segments were studied according to a gradient of root senescence: the apical and basal segments of the mycorrhiza and the mycorrhiza-carrier root. Each segment contained a certain proportion of senescent cells, some of which were of fungal origin, and this proportion increased as the root aged. In the three segments, the soil/plant interfaces were differentiated, and the micro-organisms observed in situ were described. Senescent root cells contained many polyphenolic substances and our results showed that these substances were, according to the root segment, differently associated with Ca, N and Si. When all these ultrastructural data are correlated with more global data, they can be usefully applied to root cell physiology, microbiology and pedology. This approach makes it possible to specify the evolution of organic matter in situ in soils whatever its origin.

Cellular Senescence↗

Inhibition of 1,2-dimethylhydrazine-induced oxidative DNA damage in rat colon mucosa by black tea complex polyphenols.

The effect of black tea polyphenols on 1,2-dimethylhydrazine (DMH)-induced oxidative DNA damage in rat colon mucosa has been investigated. Fischer 344 rats were treated orally with thearubigin (TR) or theafulvin (TFu) for 10 days (40 mg/kg), injected ip with DMH (20 mg/kg) or saline and sacrificed 24 hr after DMH administration. The levels of 8-hydroxy-2'-deoxyguanosine (8-OHdG) were measured in colonic mucosa DNA and expressed as a ratio relative to 2'-deoxyguanosine (2dG). Control rat mucosa had 8-OHdG values of 1.12 +/- 0.14/10(5) dG (mean +/- SEM, n=11), whereas DMH-treated rats significantly higher values (1.52 +/- 0.14/10(5) dG, n=26, P<0.05). Pretreatment of rats with TR had significantly inhibited DMH-induced oxidative DNA damage 0.99 +/- 0.09/10(5) dG, n=10, P<0.05) and a similar, although less marked, effect was observed with TFu (1.15 +/- 0.19/10(5), n=9, P=0.06). These findings confirm that DMH causes oxidative DNA damage in the colon mucosa of rats and demonstrate that this effect is prevented by the consumption of complex polyphenols from black tea.

1,2-Dimethylhydrazine↗

Green tea polyphenols and tannic acid act as potent inhibitors of phorbol ester-induced nitric oxide generation in rat hepatocytes independent of their antioxidant properties.

The deleterious effects of excessive release of nitric oxide (NO) have been implicated in the tissue damage and inflammation. In this study, the effect of various flavonoids and other oxidant scavenging chemical agents have been studied for their ability to inhibit 12-O-tetradecanoyl phorbol 13-acetate (TPA)-induced NO generation in rat hepatocyte. Hepatocytes activated with TPA (25-200 nM) released NO in a concentration- and time-dependent manner. Green tea polyphenols (GTP) and tannic acid (TA) were most effective in inhibiting TPA-induced NO generation (90%). These agents were also effective in inhibiting NO formation when added 2 h following TPA addition. The other oxidant scavengers, such as L-histidine, sodium azide, vitamin E and sodium benzoate, were not found to be effective even up to 1.0 mM concentration. These results suggest that TA and GTP are potent inhibitors of NOS activity and the inhibition of TPA-induced NO generation by these polyphenols is independent of their antioxidant activity. It is tempting to speculate that these agents could be utilized in the pharmacological manipulations of NO-dependent pathophysiological responses.

Animals↗

Molecular analysis of the inhibitory effects of oolong tea polyphenols on glucan-binding domain of recombinant glucosyltransferases from Streptococcus mutans MT8148.

An oolong tea polyphenol (OTF6) has been shown to possess a strong anti-glucosyltransferase (GTF) activity and inhibit experimental dental caries in rats infected with mutans streptococci. The effects of OTF6 on the functional domains of GTFs of Streptococcus mutans, an N-terminal catalytic domain (CAT), and a C-terminal glucan-binding domain (GBD), were examined. The maximum velocity of glucan synthesis by recombinant GTFB (rGTFB) and GTFD (rGTFD) became significantly slower in the presence of OTF6, however, Km values remained stable when compared in their absence. These results suggest that OTF6 reduces glucan synthesis by non-competitively inhibiting the GBD of S. mutans GTFB and GTFD. Further, the recombinant proteins of CAT (rCAT) and GBD (rGBD) were expressed using Escherichia coli, and purified by affinity column chromatography. rGBD but not rCAT was found to possess dextran-binding activity, which was shown to be inhibited by OTF6. These results indicate that OTF6, a polymeric polyphenol specific for oolong tea is able to reduce glucan synthesis by inhibiting the GBD of S. mutans GTFB.

Binding Sites↗

Reduction of oxidative stress and cytokine-induced neutrophil chemoattractant (CINC) expression by red wine polyphenols in zinc deficiency induced intestinal damage of rat.

Consumption of red wine has been associated with health promotion and disease prevention. We have previously found that the intestine of zinc-deficient (ZD) rats develop oxidative damage associated with inflammation. Here we have used this model to investigate whether red wine polyphenols could protect against intestinal injury and, if so, whether this protection was achieved through antioxidant and anti-inflammatory activity. The intestinal alterations induced by zinc deficiency such as morphological damage, increased TBA-RS level and CuZn-superoxide dismutase activity, and decreased glutathione peroxidase activity, did not develop with the administration to ZD rats of a suspension of dealcoholated red wine (RWS). The same treatment induced in control rats a decrease of TBA-RS level but also of glutathione peroxidase and catalase activity. Treatment with RWS to ZD rats prevented a marked mucosal macrophage and neutrophil infiltration. The expression of pro-inflammatory cytokines, such as tumor necrosis factor alpha and cytokine-induced neutrophil chemoattractant (CINC), was induced by zinc deficiency, whereas that of the anti-inflammatory interleukin-10 was suppressed. Treatment with RWS reduced CINC expression. These results report a novel activity of red wine polyphenols in downregulation of intestinal CINC expression, which likely protects cells against inflammatory processes.

Animals↗

Effects of tannins and related polyphenols on superoxide-induced histamine release from rat peritoneal mast cells.

The effects of tannins and related polyphenols on KO2- and compound 48/80-induced histamine release from rat peritoneal mast cells were examined. Pretreatment with hydrolyzable tannins (1-100 microM) significantly inhibited KO2-induced histamine release. Dimeric ellagitannins, which have hexahydroxydiphenoyl (HHDP) and valoneoyl residues and/or a valoneoyl-related acyl unit in the molecule, showed more potent inhibitory effects than monomeric hydrolyzable tannins. The most effective inhibition was exhibited by agrimoniin and euphorbin C (IC50 0.68 and 0.80 microM), which have dehydrodigalloyl and euphorbinoyl groups, respectively, as well as the HHDP group. However, procyanidins, flavonoids and related polyphenols with small molecular weights, except for epigallocatechin gallate, exhibited negligible effects. Although clinically used antiallergic drugs, azelastine, astemizole, ketotifen and epinastine have been shown to prevent KO2-induced histamine release, their potencies were all less than those of ellagitannins. An inhibitory effect on compound 48/80-induced histamine release was also exhibited by higher molecular weight tannins. The inhibitory effect on histamine release caused by different stimulants suggested that ellagitannins act as cell membrane stabilizers as well as radical scavengers.

Animals↗

Green tea polyphenols: DNA photodamage and photoimmunology.

Green tea is a popular beverage consumed worldwide. The epicatechin derivatives, which are commonly called 'polyphenols', are the active ingredients in green tea and possess antioxidant, anti-inflammatory and anti-carcinogenic properties. Studies conducted by our group on human skin have demonstrated that green tea polyphenols (GTP) prevent ultraviolet (UV)-B-induced cyclobutane pyrimidine dimers (CPD), which are considered to be mediators of UVB-induced immune suppression and skin cancer induction. GTP treated human skin prevented penetration of UV radiation, which was demonstrated by the absence of immunostaining for CPD in the reticular dermis. The topical application of GTP or its most potent chemopreventive constituent (-)-epigallocatechin-3-gallate (EGCG) prior to exposure to UVB protects against UVB-induced local as well as systemic immune suppression in laboratory animals. Additionally, studies have shown that EGCG treatment of mouse skin inhibits UVB-induced infiltration of CD11b+ cells. CD11b is a cell surface marker for activated macrophages and neutrophils, which are associated with induction of UVB-induced suppression of contact hypersensitivity responses. EGCG treatment also results in reduction of the UVB-induced immunoregulatory cytokine interleukin (IL)-10 in skin as well as in draining lymph nodes, and an elevated amount of IL-12 in draining lymph nodes. These in vivo observations suggest that GTPs are photoprotective, and can be used as pharmacological agents for the prevention of solar UVB light-induced skin disorders associated with immune suppression and DNA damage.

Animals↗

Quantitative EPR study on free radicals in the natural polyphenols interacting with metal ions and other environmental pollutants.

Quantitative electron paramagnetic resonance (EPR) method was applied to characterise radicals stabilised in polyphenolic matrices of various biogenic materials: lichens, mosses, composts, soils, peats, brown coals and sewage sludge sediments. The investigations were carried out on raw materials and extracted fractions of humic acids (HA). General trends of g value and spin concentration changes were found. These parameters in lichens strongly depend on lichen species and air pollution. Determination of the g value and semiquinone spin concentration allows to assess degree of transformation of organic matter in compost, soil, peat and lignite. Application of gaseous ammonia as a base penetrating the organic matrices extends the possibilities and usefulness of the method. Interaction of metal ions with humic materials is illustrated by interaction of VO2+ ion with peat and lignite HA as well as demineralised (raw and carbonised) brown coal. Our investigations demonstrate that quantitative EPR is a rapid and effective monitoring method to study the influence of various environmental factors on substances containing polyphenolic matrices.

Bryopsida↗

Enzymatically and combinatorially generated array-based polyphenol metal ion sensor.

Phenolic polymers were synthesized via soybean hull peroxidase catalysis and used as metal-based sensor components in a polymer array. A sensor array for Fe(3+), Cu(2+), Co(2+), and Ni(2+) has been developed consisting of 15 phenolic homopolymers and copolymers generated from five phenolic monomers by peroxidase-catalyzed oxidative polymerization. Sensing was based on the change of intrinsic polyphenol fluorescence upon addition of a metal ion or a metal ion mixture to an aqueous suspension of a polyphenol. Importantly, the fluorescence response of copolymers differed, in some cases dramatically, from the constituent homopolymers and was dependent upon the relative ratio of monomers that comprise the polymer. This finding suggests that an extremely broad range of sensor arrays can be generated from a limited number of phenolic monomers. Using a statistical analysis, histograms constructed for the four different metal ions yielded unique fingerprints of the array response and can be used to identify specific metal ions.

Biosensing Techniques↗

Polyphenols newly extracted in red wine from southwestern France by centrifugal partition chromatography.

Polyphenols from the ethyl acetate extracts of red wine were successfully fractionated using a four-step process (solvent extraction, ion-exchange column chromatography, centrifugal partition chromatography, and semipreparative HPLC), which resulted in the isolation of 22 compounds belonging to different classes of polyphenols (stilbenes, cinnamic acids, flavonoids). Five of them are red wine constituents reported for the first time. The newly isolated compounds include resveratrol dimers, dihydroflavonols, and a cinnamic derivative.

Chromatography↗

Factors affecting the caffeine and polyphenol contents of black and green tea infusions.

The effects of product and preparation variables on the in-cup chemical composition of tea extracts is of interest because the appearance and taste characteristics and the possible health effects of a tea liquor arise from the chemical components extracted from the leaf during tea preparation. A comprehensive study was therefore undertaken to determine the contributions of product and preparation variables on the total soluble solids, caffeine, and polyphenol contents of tea extracts. The results of this study show that the variety, growing environment, manufacturing conditions, and grade (particle size) of the tea leaves each influence the tea leaf and final infusion compositions. In addition, the composition of the tea infusion was shown to be influenced by whether the tea was contained in a teabag and, if so, the size and material of construction of the bag. Finally, the preparation method, including the amounts of tea and water used, infusion time, and amount of agitation, was shown to be a major determinant of the component concentrations of tea beverages as consumed. An illustration of the variation introduced by these product and preparation factors is provided by comparing solids, caffeine, and polyphenol contents of green and black tea infusions when commercial products are prepared according to the instructions given on their packaging.

Caffeine↗

Black tea polyphenols, theaflavins, prevent cellular DNA damage by inhibiting oxidative stress and suppressing cytochrome P450 1A1 in cell cultures.

Tea polyphenols have been demonstrated as chemopreventive agents in a number of experimental models. However, less is known about the mechanism of chemoprevention by black tea compared with that of green tea. Some beneficial properties of theaflavins, the black tea polyphenols, were investigated in the present study. Theaflavins showed inhibitory effects on H(2)O(2)- and tert-butyl hydroperoxide (tBuOOH)-induced cytotoxicity (evaluated by tetrazolium bromide reduction), cellular oxidative stress (detected by oxidation of 2', 7'-dichlorofluorescin), and DNA damage (measured by amount of 8-OHdG and comet assay) in rat normal liver epithelium cell RL-34 cell lines. In addition, theaflavins also exhibited suppression of cytochrome P450 1A1 induced by omeprazole in the human hepatoma HepG2 cell line. Furthermore, when HepG2 cells were pretreated with omeprazole to induce CYP1A1, then exposed to benzo[a]pyrene (B[a]P), DNA damage was observed using the comet assay. However, theaflavins could inhibit this DNA damage. These results indicated that theaflavins could prevent cellular DNA damage by inhibiting oxidative stress and suppressing cytochrome P450 1A1 in cell cultures.

Animals↗

Determination of antioxidant power of red and white wines by a new electrochemical method and its correlation with polyphenolic content.

A new method for measuring the antioxidant power of wine has been developed based on the accelerated electrochemical oxidation of 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS). The calibration (R = 0.9922) and repeatability study (RSD = 7%) have provided good statistical parameters. The method is easy and quick to apply and gives reliable results, requiring only the monitoring of time and absorbance. It has been applied to various red and white wines of different origins. The results have been compared with those obtained by the total antioxidant status (TAS) method. Both methods reveal that the more antioxidant wines are those with higher polyphenolic content. From the HPLC study of the polyphenolic content of the same samples, it is confirmed that there is a positive correlation between the resveratrol content of a wine and its antioxidant power.

Antioxidants↗

Isolation and characterization of polyphenol type-A polymers from cinnamon with insulin-like biological activity.

The causes and control of type 2 diabetes mellitus are not clear, but there is strong evidence that dietary factors are involved in its regulation and prevention. We have shown that extracts from cinnamon enhance the activity of insulin. The objective of this study was to isolate and characterize insulin-enhancing complexes from cinnamon that may be involved in the alleviation or possible prevention and control of glucose intolerance and diabetes. Water-soluble polyphenol polymers from cinnamon that increase insulin-dependent in vitro glucose metabolism roughly 20-fold and display antioxidant activity were isolated and characterized by nuclear magnetic resonance and mass spectroscopy. The polymers were composed of monomeric units with a molecular mass of 288. Two trimers with a molecular mass of 864 and a tetramer with a mass of 1152 were isolated. Their protonated molecular masses indicated that they are A type doubly linked procyanidin oligomers of the catechins and/or epicatechins. These polyphenolic polymers found in cinnamon may function as antioxidants, potentiate insulin action, and may be beneficial in the control of glucose intolerance and diabetes.

Antioxidants↗

Activity and concentration of polyphenolic antioxidants in apple juice. 3. Stability during storage.

Kinetic data are reported describing the stability of various classes of polyphenolic antioxidants in an apple juice enriched in these compounds as a function of storage temperature and oxygen concentration. The most thermally sensitive compounds were the various quercetin glycosides and epicatechin, whereas phloridzin and chlorogenic acid were more stable. The quercetin glycosides showed differences in their stability: quercetin galactoside approximately quercetin rhamnoside > quercetin glucoside/rutinoside > quercetin arabinoside. The effect of the presence of oxygen on the degradation rates was clear for only quercetin and to a lesser extent for epicatechin. Accelerated shelf-life testing of enriched apple juice during 4 days at 80 degrees C showed decreases in the antioxidant activity of 20-40%. The parameters obtained were used to predict the stability at different storage conditions. Calculations showed that polyphenolic antioxidants and antioxidant activity of enriched apple juice will be quite stable at ambient or refrigerated storage conditions up to half a year.

Antioxidants↗