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PubMed2006

Recognition characters in peptide-polyphenol complex formation.

Dietary polyphenols have received attention for their anti-oxidative, anti-carcinogenic and anti-neurodegenerative effects. Polyphenols bind to proteins leading to the formation of soluble or insoluble protein-polyphenol complexes which could significantly influence their biological activities. NMR and molecular modeling studies were performed to investigate the influence of the bulk, flexibility and hydrophobicity of polyphenols on the association with bradykinin, the peptide model. Our results show that the strength of the interactions could be positively correlated with polyphenol hydrophobicity and a comparison between pentagalloylglucose and vescalagin indicated that flexibility might play a positive role in the interaction with peptides and proteins.

Biphenyl Compounds↗
PubMed2006

Regulation of inflammation and redox signaling by dietary polyphenols.

Reactive oxygen species (ROS) play a key role in enhancing the inflammation through the activation of NF-kappaB and AP-1 transcription factors, and nuclear histone acetylation and deacetylation in various inflammatory diseases. Such undesired effects of oxidative stress have been found to be controlled by the antioxidant and/or anti-inflammatory effects of dietary polyphenols such as curcumin (diferuloylmethane, a principal component of turmeric) and resveratrol (a flavonoid found in red wine). The phenolic compounds in fruits, vegetables, tea and wine are mostly derivatives, and/or isomers of flavones, isoflavones, flavonols, catechins, tocopherols, and phenolic acids. Polyphenols modulate important cellular signaling processes such as cellular growth, differentiation and host of other cellular features. In addition, they modulate NF-kappaB activation, chromatin structure, glutathione biosynthesis, nuclear redox factor (Nrf2) activation, scavenge effect of ROS directly or via glutathione peroxidase activity and as a consequence regulate inflammatory genes in macrophages and lung epithelial cells. However, recent data suggest that dietary polyphenols can work as modifiers of signal transduction pathways to elicit their beneficial effects. The effects of polyphenols however, have been reported to be more pronounced in vitro using high concentrations which are not physiological in vivo. This commentary discusses the recent data on dietary polyphenols in the control of signaling and inflammation particularly during oxidative stress, their metabolism and bioavailability.

Animals↗
PubMed2006

Polyphenols prevent cell shedding from mouse mammary cancer spheroids and inhibit cancer cell invasion in confrontation cultures derived from embryonic stem cells.

The prognosis of cancer disease is worsened upon shedding of tumor cells from the primary tumor, which escape to the blood stream and form metastases at distant sites within the body. Inhibition of cell shedding from the primary tumor could therefore be exploited to avoid metastasis and delay the progression of the cancer disease. In the present study, we investigated the effects of the polyphenols resveratrol, baicalein, epicatechin, epigallocatechin and polyphenon 60 on cell shedding from multicellular tumor spheroids of the murine mammacarcinoma cell line 4T1, cell invasion into embryonic stem cell-derived tissues, generation of reactive oxygen species (ROS) and expression of matrix metalloproteinase 9 (MMP-9). With increasing tumor spheroid growth MMP-9 expression was upregulated and cells detached from tumor spheroids and formed subspheroids that displayed pronounced ROS generation. Upon incubation with polyphenols tumor growth was arrested and cell shedding was totally abolished. Polyphenol treatment decreased ROS generation and downregulated MMP-9 expression. Furthermore, polyphenols significantly inhibited invasion of tumor cells into embryonic stem cell-derived, vascularized tissues. Our data suggest, that polyphenols inhibit cell shedding and invasion by their anti-oxidative capacity and downregulation of MMP-9 expression.

Animals↗
PubMed2004

Vascular effects of wine polyphenols.

Moderate consumption of red wine has been putatively associated with lowering the risk of developing coronary heart disease. This beneficial effect is mainly attributed to the occurrence of polyphenol compounds such as anthocyanosides (ACs), catechins, proanthocyanidins (PAs), stilbenes and other phenolics in red wine. This review focuses on the vascular effects of red wine polyphenols (RWPs), with emphasis on anthocyanosides and proanthocyanidins. From in vitro studies, the effect of red wine polyphenols on the vascular tone is thought to be due to short- and long-term mechanisms. NO-mediated vasorelaxation represents the short-term response to wine polyphenols, which exert the effect by increasing the influx of extracellular Ca(2+), and the mobilization of intracellular Ca(2+) in endothelial cells. Polyphenolic compounds may also have long-term properties, as they increase endothelial NO synthase expression acting on the promoter activity. In addition, they decrease the expression of adhesion molecules and growth factors, involved in migration and proliferation of vascular smooth muscle cells. Moreover, they inhibit platelet aggregation. However, a paucity of data as regards the bioavailability and metabolism of these compounds in human studies is a limiting factor to proving their efficacy in vivo.

Anthocyanins↗
PubMed2006

Molecular targets of tea polyphenols in the cardiovascular system.

Tea-derived polyphenols have attracted considerable attention in the prevention of cancer and cardiovascular diseases. In comparison to tumour cells, the elucidation of their molecular targets in cardiovascular relevant cells is still at the beginning. Although promising experimental and clinical data demonstrate protective effects for the cardiovascular system, little information is actually available on how these beneficial effects of tea polyphenols are mediated at the cellular level. By affecting the activity of receptor and signal transduction kinases, both catechins and theaflavins--the major ingredients of green and black tea, respectively--exert a variety of cardiovascular beneficial effects. In general, the number and positions of galloyl groups have major influence on the potency of polyphenols. Compared to their broad impact on cellular signal transduction, tea polyphenols reveal little transcriptional effects. However, more detailed and profound analysis of molecular actions in different cells of the cardiovascular system is necessary before safe clinical use of tea polyphenols for treatment of cardiovascular diseases will become possible.

Animals↗
PubMed2006

Effects of polyphenolic antioxidants on exercise-induced oxidative stress.

Polyphenols are of increasing interest to consumers and food manufacturers for several reasons. Commonly referred to as antioxidants (they are the most abundant antioxidants in our diets), they may prevent various oxidative stress-related diseases, such as cancer, cardiovascular disease, inflammation and others. Physical activity is known to induce oxidative stress in individuals after intensive exercise. In this study, the effect of the flavonoid contents (which are the most abundant polyphenols) was investigated, as the only antioxidant in a replacement drink designed for sportsmen on various oxidative stress biomarkers after two identical trials of sub-maximal aerobic exercise, in a group of 30 sportsmen. In one of the trials, the cyclists consumed the antioxidant supplement (with 2.3g polyphenols/trial), and in another they consumed a placebo. Blood samples were collected both at rest and after exercise immediately and 45 minutes (min) later, for measurements of plasmatic indices of oxidative stress: lipid oxidation (TBARS), total antioxidant status (TAS); protein oxidation (carbonyl groups, CO) and the lactate dehydrogenase (LDH) and creatine kinase (CK) enzymes for each trial. All values were adjusted for changes in plasma volume. No changes were detected in plasma TAS and LDH after exercise or after the polyphenolic supplement. CK and TBARS increased after exercise in both tests. However, in response to strenuous exercise, the polyphenol-supplemented test showed a smaller increase in plasma TBARS and CK than the placebo test. CO increased by 12% in response to the placebo test, whereas it decreased by 23% in the polyphenol-supplement test. This may indicate that the antioxidant supplement offered protection against exercise-induced oxidative stress.

Adult↗
PubMed2006

Antioxidant activity of polyphenols from solid olive residues of c.v. Coratina.

The antioxidant profile of extracts from solid olive residue (SOR) of c.v. Coratina, a cultivar widely diffused in the south of Italy, using both cell-free and cell-based experimental models, was investigated. A total hydroalcoholic extract (polyphenols content 19.7%) and a purified extract (Oleaselecttrade mark) (polyphenols content 35.1%) were tested for their ability to quench the stable free radical DPPH, the peroxyl radicals (ORAC assay), by monitoring the loss in fluorescence of R-phycoerythrin induced by the peroxyl radical generator AAPH and their ability to inhibit the cumene hydroperoxide-induced lysis of rat red blood cells (RBC). The total hydroalcoholic extract showed IC(50) 26.96+/-1.53 microg/ml in the DPPH assay, that 10 microg/ml were equivalent to 2.11+/-0.12 microg/ml Trolox (ORAC assay) and IC(50) 1.7+/-0.20 microg/ml in the RBC hemolysis. The Oleaselect extract was 4 to 5 folds more active than the hydroalcoholic extract in all the experimental models, with IC(50) values of 7.36+/-0.38 microg/ml in the DPPH test and of 0.38+/-0.03 microg/ml in RBC; the antioxidant activity in the ORAC assay was slightly greater than that of Trolox (10 microg/ml equivalent to 11.45+/-0.40 microg/ml). The scavenging effect of the extract in the ORAC assay was compared to that of verbascoside (the main polyphenol component) and of caffeic acid (the basic constituent of verbascoside): the results indicate that caffeic acid (10 microg/ml equivalent to 35.70+/-2.95 microg/ml Trolox) is more potent than verbascoside (10 microg/ml equivalent to 15.42+/-1.21 microg/ml Trolox) in entrapping peroxyl radicals. Finally the antioxidant activity of the Oleaselect extract was confirmed in human umbilical endothelial cells (EC) exposed to the site-specific peroxyl radical inducer AAPH, where a massive lipid peroxidation process (marker the fluorescence probe BODIPY) takes place, paralleled by a marked loss of cell viability (calcein assay). The purified extract (1-20 microg/ml) pre-incubated with EC for 1 h dose-dependently inhibited both the lipid-peroxidation damage and cell death. Taking into account the total polyphenol content, these results clearly indicate a greater antioxidant activity for the purified extract, due to a cooperative antioxidant interaction among its polyphenol constituents.

Amidines↗
PubMed2004

Wine polyphenols and ethanol do not significantly scavenge superoxide nor affect endothelial nitric oxide production.

Epidemiological studies have shown that moderate intake of red wine reduces the risk of coronary heart disease. It has been proposed that the antiatherogenic effect be due to the scavenging of reactive oxygen species by polyphenols and ethanol or an effect on endothelial nitric oxide (NO) production. We have determined the reaction rates of superoxide with four different polyphenols and ethanol. The superoxide reaction rates were determined at 37 degrees C and pH 7.4 using competitive spin trapping and electron paramagnetic resonance (EPR) spectroscopy. Ethanol did not scavenge superoxide. For the polyphenols catechin, epicatechin, gallic acid, and quercetin, we find rate constants of respectively 2.3*10(4), 2.2*10(4), 2.3*10(3) and 1.9*10(4)(mole per second)(-1). Polyphenols can only exert a significant scavenging effect, if the plasma concentration reach sufficiently high levels. At concentrations found in vivo (low nanomolar range), the scavenging of superoxide by polyphenols and ethanol is negligible in comparison with endogenous protection against superoxide. Incubation of cultured endothelial cells with 5 micromol/L of catechin, epicatechin, gallic acid, quercetin, or ethanol 0.05% (v/v) did not influence the maximal production of NO by these cells as measured by fluorescent nitric oxide cheletropic traps (FNOCT). The observed antiatherogenic effects must be caused by a mechanism other than direct scavenging of superoxide or influence on maximal endothelial NO production.

Animals↗
PubMed2005

Spectrophotometric method for polyphenols analysis: prevalidation and application on Plantago L. species.

The prevalidation strategy was applied to evaluate UV-vis spectrophotometric procedure with Folin-Ciocalteu's reagent for polyphenols determination. Favourable prevalidation characteristics verified this procedure as a valuable tool in polyphenols analysis and it was successfully applied for determination of total polyphenols and tannins in leaves, stems and flowers of Plantago L. species growing in Croatia. The results showed the variety of total polyphenols content between different plant parts (leaves: up to 10.15%; stems: up to 4.34% and flowers: up to 5.56%). The content of tannins in stems was from 0.28% to 1.00%, while leaves and flowers contained tannins in concentrations of 2.26% and 2.21%, respectively. The results of polyphenols determination were evaluated by using multivariate analysis (UPGMA and PCA) as a contribution to elucidation of relations between different taxa of genus Plantago L.

Chemistry, Pharmaceutical↗
PubMed2006

Protective effect of Mangifera indica L. polyphenols on human T lymphocytes against activation-induced cell death.

Activation-induced cell death (AICD) plays an important role in maintenance of peripheral lymphocyte homeostasis. Reactive oxygen species (ROS) combined with simultaneous calcium (Ca(2+)) influx into the cytosol are required for induction of AICD. The extract obtained from the stem bark of Mangifera indica L. has shown to protect T cells from in vitro AICD. This extract is rich in polyphenolic compounds, the three main components of which are mangiferin (MA), catechin (C) and epicatechin (EC). The present study has focused on the possible contribution of the polyphenols MA, C and EC to the demonstrated protective effect of M. indica extract on in vitro human T cell AICD. Our results show that these polyphenols diminished the increase of intracellular ROS and free Ca(2+) induced by T cell receptor (TCR) triggering. In addition, these polyphenols attenuated AICD. Our findings suggest that the T cell survival effect of M. indica extract is mediated, at least in part, by its main polyphenols.

Apoptosis↗
PubMed2003

Successful storage of peripheral nerve before transplantation using green tea polyphenol: an experimental study in rats.

Green tea polyphenol is known to act as a buffer, reducing biological responses to oxidative stress. Several effects of polyphenol have been reported, such as protection of tissue from ischemia, antineoplasmic and anti-inflammatory effects, and suppression of arteriosclerosis. In this study, we investigated whether peripheral nerve segments could be kept viable in a polyphenol solution for 1 month. Sciatic nerve segments, 20 mm long, were harvested from Lewis rats and treated in three different ways before transplanting to recipient Lewis rats to bridge sciatic nerve gaps created by removal of 15-mm-long nerve segments. Group F: nerve segments were transplanted immediately after harvesting. Group P: nerve segments were transplanted after they had been stored in Dulbecco's Modified Eagle's Medium (DMEM) containing polyphenol for 7 days at 4 degrees C and then in DMEM for 21 days at 4 degrees C. Group M: nerve segments were stored in DMEM solution alone for 28 days at 4 degrees C. Viability of the nerve segments was assessed by vital staining (calcein-AM/ethidium homodimer), by electron microscopy and by genomic studies before transplantation. Nerve regeneration was evaluated using electrophysiological and morphological studies 12 and 24 weeks after transplantation. Neural cell viability of the preserved nerve segments was confirmed in group P, in which the nerve regeneration was similar to that in group F and superior to that in group M. Peripheral nerve segments can be successfully preserved for 1 month using green tea polyphenol.

Animals↗
PubMedDate not supplied

Direct reduction of N-acetoxy-PhIP by tea polyphenols: a possible mechanism for chemoprevention against PhIP-DNA adduct formation.

The chemopreventive effect of tea against 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP)-DNA adduct formation and its mechanism were studied. Rats were exposed to freshly prepared aqueous extracts of green tea (3% (w/v)) as the sole source of drinking water for 10 days prior to administration with a single dose of PhIP (10 mg/kg body weight) by oral gavage. PhIP-DNA adducts in the liver, colon, heart, and lung were measured using the 32P-postlabelling technique. Rats pre-treated with tea and given PhIP 20 h before sacrifice had significantly reduced levels of PhIP-DNA adducts as compared with controls given PhIP alone. The possible mechanism of protective effect of tea on PhIP-DNA adduct formation was then examined in vitro. It was found that an aqueous extract of green and black tea, mixtures of green and black tea polyphenols, as well as purified polyphenols could strongly inhibit the DNA binding of N-acetoxy-PhIP, a putative ultimate carcinogen of PhIP formed in vivo via metabolic activation. Among these, epigallocatechin gallate was exceptionally potent. HPLC analyses of these incubation mixtures containing N-acetoxy-PhIP and the tea polyphenols each revealed the production of the parent amine, PhIP, indicating the involvement of a redox mechanism. In view of the presence of relatively high levels of tea polyphenols in rat and human plasma after ingestion of tea, this study suggests that direct reduction of the ultimate carcinogen N-acetoxy-PhIP by tea polyphenols is likely to be involved in the mechanism of chemoprotection of tea against this carcinogen.

Animals↗
PubMed1996

Tea polyphenols as inhibitors of mutagenicity of major classes of carcinogens.

Previous research suggested that the mutagenicity of some genotoxic carcinogens, mainly heterocyclic amines, was decreased by green or black tea extracts, or tea polyphenol fractions. Thus, it seemed important to test a variety of genotoxic carcinogens with distinct chemical structures and means of biochemical activation as regards modification of mutagenicity in appropriate strains of Salmonella typhimurium by 3 concentrations of polyphenols 60, 100, or B, standard commercial polyphenol preparations from green or black tea. Polyphenols sharply decreased the mutagenicity of a number of aryl- and heterocyclic amines, of aflatoxin B1, benzo[a]pyrene, 1,2-dibromoethane, and more selectively, of 2-nitropropane, all involving an induced rat liver S9 fraction. Good inhibition was found with 2 nitrosamines that required a hamster S9 fraction for biochemical activation. No effect was found with 1-nitropyrene, and with the direct-acting (no S9) 2-chloro-4-methyl-thiobutanoic acid. Thus, with some exceptions, polyphenols considerably decreased the mutagenicity of diverse types of carcinogens.

Amines↗
PubMed2003

Isolation and structure elucidation of the major individual polyphenols in carob fibre.

Although it is already known that carob fibre contains several classes of polyphenolic substances, a comprehensive analysis of these has not been conducted to date. Therefore, the major polyphenolic compounds were extracted with organic solvents, and, following fractionation by normal-phase column chromatography on silicic acid, their structures were elucidated by liquid-chromatography electrospray-ionisation mass spectrometry (LC-ESI), nano-electrospray-ionisation mass spectrometry (ESI-MS), and gas-chromatography mass spectrometry (GC-MS). In addition, complete 1H and 13C NMR assignments were obtained for the isolated gallotannins 1,6-di-, 1,2,6-tri- and 1,2,3,6-tetra-O-galloyl-beta-D-glucose. Carob fibre was found to contain a rich variety of phenolic antioxidants. A total of 24 polyphenol compounds were identified with a yield of 3.94 g/kg (dry weight). The profile was dominated by gallic acid in various forms: free gallic acid (42% of polyphenols by weight), gallotannins (29%), and methyl gallate (1%), while simple phenols, mainly cinnamic acid, made up about 2% of the total. Flavonoids represented 26% of the polyphenols, and the major components were identified as the glycosides myricetin- and quercetin-3-O-alpha-L-rhamnoside (ca. 9% and 10%, respectively). These data indicate that carob fibre is rich in both amount and variety of phenolic antioxidant substances, and its inclusion in the diet may have chemopreventive properties.

Chromatography, Ion Exchange↗
PubMed2002

The metabolic fate of dietary polyphenols in humans.

Dietary polyphenols are widely considered to contribute to health benefits in humans. However, little is yet known concerning their bioactive forms in vivo and the mechanisms by which they may contribute toward disease prevention. Although many studies are focusing on the bioavailability of polyphenols through studying their uptake and the excretion of their conjugated forms, few are emphasizing the occurrence of metabolites in vivo formed via degradation by the enzymes of colonic bacteria and subsequent absorption. The purpose of this research was to investigate the relationship between biomarkers of the colonic biotransformation of ingested dietary polyphenols and the absorbed conjugated polyphenols. The results show that the majority of the in vivo forms derive from cleavage products of the action of colonic bacterial enzymes and subsequent metabolism in the liver. Those include the glucuronides of 3-hydroxyphenylacetic, homovanillic, vanillic and isoferulic acid as well as 3-(3-methoxy-4-hydroxyphenyl)-propionic, 3-(3-hydroxyphenyl)-propionic acid, and 3-hydroxyhippuric acid. In contrast, intact conjugated polyphenols themselves, such as the glucuronides of quercetin, naringenin and ferulic, p-coumaric, and sinapic acid were detected at much lower levels. The results suggest that consideration should be given to the cleavage products as having a putative role as physiologically relevant bioactive components in vivo.

Adult↗
PubMed2003

Protective effects of green tea polyphenols on human HepG2 cells against oxidative damage of fenofibrate.

The aim of this work was to investigate the protective effects of green tea polyphenols on the cytotoxic effects of hypolipidemic agent fenofibrate (FF), a peroxisome proliferator (PP), in human HepG2 cells. The results showed that high concentrations of FF induced human HepG2 cell death through a mechanism involving an increase of reactive oxygen species (ROS) and intracellular reduced glutathione (GSH) depletion. These effects were partially prevented by antioxidant green tea polyphenols. The elevated expression of PP-activated receptors alpha (PPARalpha) in HepG2 cells induced by FF was also decreased by treatment with green tea polyphenols. In conclusion, this result demonstrates that oxidative stress and PPARalpha are involved in FF cytotoxicity and green tea polyphenols have a protective effect against FF-induced cellular injury. It may be beneficial for the hyperlipidemic patients who were administered the hypolipidemic drug fenofibrate to drink tea or use green tea polyphenols synchronously during their treatment.

Cell Line, Tumor↗
PubMed2000

Antimutagenic activity of cacao: inhibitory effect of cacao liquor polyphenols on the mutagenic action of heterocyclic amines.

We investigated the effect of polyphenols derived from cacao liquor on the mutagenic action of heterocyclic amines (HCAs) in vitro and ex vivo. In the Ames test, the cacao liquor polyphenols showed antimutagenic effects in bacteria treated with HCA in the presence of an S-9 mixture; however, they showed less efficacy than quercetin. On the other hand, the cacao liquor polyphenols showed potent antimutagenic activity in bacteria treated with activated forms of HCA, compared with quercetin. We also evaluated the effect of these compounds on enzymatic activation of HCA. They weakly suppressed the production of activated HCA. In the host-mediated assay in mice, a method used to estimate the potential carcinogenicity of chemicals ex vivo, oral administration of the cacao liquor polyphenols, reduced the number of colonies of revertant bacteria recovered from the liver. These data suggest that the cacao liquor polyphenols have an antimutagenic effect not only in vitro, but also ex vivo.

Animals↗
PubMed2001

Polyphenolic content in olive oil waste waters and related olive samples.

The production of olive oil yields a considerable amount of waste water, which is a powerful pollutant and is currently discarded. Polyphenols and other natural antioxidants, extracted from olives during oil extraction process, partially end up in the waste waters. Experimental and commercial olive oil waste waters from four Mediterranean countries were analyzed for a possible recovering of these biologically interesting constituents. Identification and quantitation of the main polyphenols were carried out by applying HPLC-DAD and HPLC-MS methods. Representative samples of ripe olives were also analyzed at the same time to correlate, if possible, their polyphenolic profiles with those of the corresponding olive oil waste waters. The results demonstrate that Italian commercial olive oil waste waters were the richest in total polyphenolic compounds with amounts between 150 and 400 mg/100 mL of waste waters. These raw, as yet unused, matrices could represent an interesting and alternative source of biologically active polyphenols.

Antioxidants↗