cyanidin-3-o-beta-glucopyranoside and ferulic-acid

Higher dietary intakes of anthocyanins have been linked epidemiologically to decreased risk for metabolic syndrome, type 2 diabetes and cardiovascular events; clinical trials and rodent studies evaluating ingestion of anthocyanin-rich extracts confirm favorable effects of these agents on endothelial function and metabolic syndrome. However, these benefits of anthocyanins are lost in rats whose gut microbiome has been eliminated with antibiotic treatment - pointing to bacterial metabolites of anthocyanins as the likely protective agents. A human pharmacokinetic assessment of orally administered cyanidin-3-O-glucoside, a prominent anthocyanin, has revealed that, whereas this compound is minimally absorbed, ferulic acid (FA) is one of its primary metabolites that appears in plasma. FA is a strong antioxidant and phase 2 inducer that has exerted marked anti-inflammatory effects in a number of rodent and cell culture studies; in particular, FA is highly protective in rodent models of diet-induced weight gain and metabolic syndrome. FA, a precursor for lignan synthesis, is widely distributed in plant-based whole foods, mostly in conjugated form; whole grains are a notable source. Coffee ingestion boosts plasma FA owing to gastrointestinal metabolism of chlorogenic acid. Hence, it is reasonable to suspect that FA mediates some of the broad health benefits that have been associated epidemiologically with frequent consumption of whole grains, anthocyanins, coffee, and unrefined plant-based foods. The molecular basis of the anti-inflammatory effects of FA may have been clarified by a recent study demonstrating that FA can target the adaptor protein MyD88; this plays an essential role in pro-inflammatory signaling by most toll-like receptors and interleukin-1β. If feasible oral intakes of FA can indeed down-regulate MyD88-dependent signaling, favorable effects of FA on neurodegeneration, hypothalamic inflammation, weight gain, adipocyte and beta cell function, adiponectin secretion, vascular health, and cartilage and bone integrity can be predicted. Since FA is well tolerated, safe, and natural, it may have great potential as a protective nutraceutical, and clinical trials evaluating its effects are needed.

Topics: Adiponectin; Administration, Oral; Animals; Anthocyanins; Anti-Inflammatory Agents; Antioxidants; Coffee; Coumaric Acids; Diabetes Mellitus; Gastrointestinal Microbiome; Glucosides; Glutathione; Humans; Inflammation; Myeloid Differentiation Factor 88; Osteoclasts; Oxidative Stress; Rats; Signal Transduction; Whole Grains

Rice bran is obtained from the rice polishing process, and this by-product contains many bioactive compounds. In this study, the composition of phenolic compounds from red and black rice brans was determined by HPLC-DAD-MS. Additionally, the neuroprotective ability of these brans in SH-SY5Y cells insulted with hydrogen peroxide (H

Topics: Anthocyanins; Antioxidants; Cell Line, Tumor; Chromatography, High Pressure Liquid; Coumaric Acids; Glucosides; Humans; Neurons; Neuroprotective Agents; Oryza; Phenols; Phytochemicals; Plant Extracts; Seeds

Cyanidin-3-glucoside (C3G) is a major anthocyanin in berries and a potential nutritional supplement for preventing retinal degeneration. However, the protective mechanism of C3G and its metabolites, protocatechuic acid (PCA) and ferulic acid (FA), remain unclear. The molecular mechanisms of C3G and its metabolites against retinal photooxidative damage in vivo are investigated.. Pigmented rabbits were orally administered C3G, PCA, and FA (0.11 mmol/kg/day) for 3 weeks. Electroretinography, histological analysis, and TUNEL assay showed that C3G and its metabolites attenuated retinal cell apoptosis. The expression of oxidative stress markers were upregulated after light exposure but attenuated by C3G and FA, which may be attributed to the elevated secretion and expression of heme oxygenase (HO-1) and nuclear factor erythroid-2 related factor 2 (Nrf2). C3G, PCA, and FA attenuated the secretion or expression of inflammation-related genes; FA suppressed nuclear factor kappa B (NF-κB) activation. The treatments attenuated the light-induced changes on certain apoptotic proteins and angiogenesis-related cytokines.. C3G and FA reduced light-induced retinal oxidative stress by activating the Nrf2/HO-1 antioxidant pathway. FA attenuated the light-induced retinal inflammation by suppressing NF-κB activation. C3G and its metabolites attenuated the photooxidation-induced apoptosis and angiogenesis in the retina.

Topics: 8-Hydroxy-2'-Deoxyguanosine; Aldehydes; Animals; Anthocyanins; Antioxidants; Apoptosis; Coumaric Acids; Cytokines; Deoxyguanosine; Glucosides; Heme Oxygenase-1; Hydroxybenzoates; In Situ Nick-End Labeling; Light; NF-E2-Related Factor 2; NF-kappa B; Oxidative Stress; Rabbits; Retina; Retinal Degeneration; Signal Transduction; Tyrosine; Up-Regulation

The interactions between polyphenols and plant fibres play an important role in controlling the release of phenolic compounds from food matrices for absorption in the gastrointestinal tract. This study probed the molecular interactions of diverse polyphenols with cellulose fibres by using a pure cellulose-producing bacterial model. Alkali treatment of bacterial cellulose was an effective method for obtaining a high purity cellulose model for study of polyphenol binding. Representatives of different polyphenol classes all bound to cellulose spontaneously, rapidly, and to comparable extents (up to 60% w/w of cellulose). Langmuir binding isotherms were applied to determine quantitative aspects of the adsorption at equilibrium. The study indicated that binding was similar on a molar basis for ferulic acid, gallic acid, catechin and cyanidin-3-glucoside (but lower for chlorogenic acid), with the native charge of polyphenols a secondary factor in the interactions between polyphenols and cellulose.

Topics: Adsorption; Alkalies; Anthocyanins; Catechin; Cellulose; Coumaric Acids; Gallic Acid; Gluconacetobacter xylinus; Glucosides; Kinetics; Magnetic Resonance Spectroscopy; Microscopy, Confocal; Nutritional Physiological Phenomena; Polyphenols

Advanced breeding lines made from the cross between the black and white rice as parents were collected to evaluate phenolic levels and antioxidant properties. No free phenolic acid was found in the soluble fraction, while p-coumaric acid, ferulic acid, isoferulic acid and vanillic acid were identified in insoluble bound fractions. Of noteworthy, is isoferulic acid which has rarely been reported to occur in cereal grains. Phenolic dehydrodimers were only observed in the insoluble bound fractions, which mainly consisted of 8-5'-coupled diferulic acids and 5-5'-coupled diferulic acids. Cyanidin 3-glucoside, peonidin 3-glucoside and cyanidin occurred in black and some light-purple rice samples. The breeding line YF53 has the highest total phenolic content (23.3mg ferulic acid equiv./g), total anthocyanin content (2.07 mg cyanidin-3-glu equiv./g), and antioxidant activities. The results indicate that it is possible to develop advanced breeding lines for improvement of the phenolic profiles and antioxidant capacity with high yield.

Topics: Anthocyanins; Antioxidants; Coumaric Acids; Edible Grain; Glucosides; Hydroxybenzoates; Oryza; Plant Extracts; Propionates; Vanillic Acid

In vitro and in vivo studies suggest that dietary anthocyanins modulate cardiovascular disease risk; however, given anthocyanins extensive metabolism, it is likely that their degradation products and conjugated metabolites are responsible for this reported bioactivity.. Human vascular endothelial cells were stimulated with either oxidized LDL (oxLDL) or cluster of differentiation 40 ligand (CD40L) and cotreated with cyanidin-3-glucoside and 11 of its recently identified metabolites, at 0.1, 1, and 10 μM concentrations. Protein and gene expression of IL-6 and VCAM-1 was quantified by ELISA and RT-qPCR. In oxLDL-stimulated cells the parent anthocyanin had no effect on IL-6 production, whereas numerous anthocyanin metabolites significantly reduced IL-6 protein levels; phase II conjugates of protocatechuic acid produced the greatest effects (>75% reduction, p ≤ 0.05). In CD40L-stimulated cells the anthocyanin and its phase II metabolites reduced IL-6 protein production, where protocatechuic acid-4-sulfate induced the greatest reduction (>96% reduction, p ≤ 0.03). Similarly, the anthocyanin and its metabolites reduced VCAM-1 protein production, with ferulic acid producing the greatest effect (>65% reduction, p ≤ 0.04).. These novel data provide evidence to suggest that anthocyanin metabolites are bioactive at physiologically relevant concentrations and have the potential to modulate cardiovascular disease progression by altering the expression of inflammatory mediators.

Topics: Anthocyanins; CD40 Ligand; Coumaric Acids; Endothelial Cells; Gene Expression; Glucosides; Glucuronides; Human Umbilical Vein Endothelial Cells; Humans; Hydroxybenzoates; Interleukin-6; Lipoproteins, LDL; RNA, Messenger; Vascular Cell Adhesion Molecule-1

Four polyphenols: ferulic acid and p-coumaric acid (hydroxycinnamic acids), quercetin (flavonol) and cyanidin 3-glucoside (anthocyanin) were selected, and their antioxidant properties and their influence on cholesterol concentration in hypercholesterolemic and normal erythrocytes were investigated.. To determine the effect of phenolic compounds, we prospectively studied cholesterol concentration, lipid peroxidation and membranes fluidity. Whole-blood and isolated erythrocytes (2% hematocrit) were incubated for 24 h with selected compounds at concentration 1, 10 and 100 μmol/L. All investigated compounds decreased lipid peroxidation in whole blood. Cyanidin 3-glucoside and quercetin showed higher antioxidant properties than hydroxycinnamic acids (ferulic acid and p-coumaric acid).. Incubation of whole blood of hypercholesterolemic patients with quercetin and cyanidin 3-glucoside resulted in statistically significant reduction of cholesterol concentration in erythrocytes down to 75% (at 10 μmol/L of polyphenols) and 69% (at 100 μmol/L of polyphenols) of initial values. The effect of both compounds on isolated erythrocytes was even more pronounced, reduction down to 70% (at 10 μmol/L of polyphenols) and 58% (at 100 μmol/L of polyphenols) of initial values. After incubation of isolated erythrocytes of hypercholesterolemic patients with quercetin and cyanidin 3-glucoside, increase of membrane fluidity was noticed. After incubation of isolated erythrocytes of healthy donors with investigated compounds, no changes in membrane fluidity were observed.. Our results indicate that flavonols and anthocyanins have higher antioxidant properties and higher influence on cholesterol concentration in erythrocytes membranes than simple hydroxycinnamic acids.

Topics: Anthocyanins; Antioxidants; Cholesterol; Coumaric Acids; Dietary Supplements; Erythrocyte Membrane; Erythrocytes; Glucosides; Humans; Hypercholesterolemia; Hypolipidemic Agents; Lipid Peroxidation; Male; Membrane Fluidity; Middle Aged; Osmolar Concentration; Propionates; Quercetin; Thiobarbituric Acid Reactive Substances

Intermolecular copigmentation reactions are significantly responsible for the manifold color expression of fruits, berries, and their products. These reactions were investigated with five anthocyanins and five phenolic acids acting as copigments. The stability of the pigment-copigment complexes formed was studied during a storage period of 6 months. The study was conducted using a UV-visible spectrophotometer to monitor the hyperchromic effect and the bathochromic shift of the complexes. The greatest copigmentation reactions took place in malvidin 3-glucoside solutions. The strongest copigments for all anthocyanins were ferulic and rosmarinic acids. The immediate reaction of rosmarinic acid with malvidin 3-glucoside resulted in the biggest bathochromic shift (19 nm) and the strongest hyperchromic effect, increasing the color intensity by 260%. The color induced by rosmarinic acid was not very stable. The color intensity of pelargonidin 3-glucoside increased greatly throughout the storage period with the addition of ferulic and caffeic acids.

Topics: Anthocyanins; Caffeic Acids; Cinnamates; Color; Coumaric Acids; Depsides; Drug Stability; Food Preservation; Glucosides; Hydroxybenzoates; Pigments, Biological; Rosmarinic Acid; Solutions; Time Factors