cyanidin-3-o-beta-glucopyranoside and petunidin-3-glucoside

In this study, intermolecular copigmentation between five primary wine monoglucosidic anthocyanins (cyanidin-3-O-glucoside, peonidin-3-O-glucoside, delphinidin-3-O-glucoside, petunidin-3-O-glucoside, and malvidin-3-O-glucoside) and three common wine phenolics (gallic acid, (-)-epicatechin, and quercetin-3-O-glucoside) were investigated through experimental and theoretical methods, and the influence of substituent pattern of anthocyanin B ring was studied emphatically. Chromatic and thermodynamic analysis showed there were great differences among these different pigment-copigment systems. Spatial conformations of the 15 copigmentation complexes were obtained through theoretical calculation, and diverse π-π stacking modes were observed. These results indicated that the substituent pattern of anthocyanin B ring had significant impact on its affinity to copigments, and more, the structures of pigments and copigments determined the color expression and stability of copigmentation together.

Topics: Anthocyanins; Color; Glucosides; Molecular Structure; Phenols; Quercetin; Wine

The reaction kinetics of five primary wine anthocyanins (cyanidin-3-O-glucoside, peonidin-3-O-glucoside, delphinidin-3-O-glucoside, petunidin-3-O-glucoside, and malvidin-3-O-glucoside) and (-)-epicatechin with the presence of acetaldehyde were evaluated in model wine solutions at a range of varying temperatures (25, 35, 45, and 55 °C). The loss of anthocyanins followed first-order reaction model, while the formation of two isomers of anthocyanin ethyl-linked (-)-epicatechin was fitted to zero-order reaction model. The rate constant (k) showed that petunidin-3-O-glucoside was the most reactive anthocyanin, followed by the two 3',4'-substituted anthocyanins (peonidin-3-O-glucoside and cyanidin-3-O-glucoside), while the least reactive were another two 3',4',5'-substituted anthocyanins (malvidin-3-O-glucoside and delphindin-3-O-glucoside). The activation energies (E

Topics: Acetaldehyde; Anthocyanins; Catechin; Color; Glucosides; Isomerism; Kinetics; Spectrophotometry; Temperature; Thermodynamics; Wine

Beibinghong Vitis amurensis Rupr has wide plantation area, high productivity and rich anthocyanin. Common hot-extraction has poor deficiency and destroys anthocyanin severely. For Beibinghong V. amurensis Rupr as materials, response surface-optimised electric fields were used, the structure of Beibinghong was observed by SEM, antioxidant activity was measured by DPPH, ABTS and reducing force, the component of anthocyanin was analyzed by HPLC-MS. We found the content of total anthocyanin extracted by pulsed electric fields was 166.65 ± 3.88 mg/100 g.FW. Total anthocyanin from Beibinghong had high antioxidant activity, also contained multiple steady anthocyanin of delphinidin 3-O-glucoside, cyanidin 3-O-glucoside, petunidin 3-O-glucoside, peonidin 3-O-glucoside, malvidin 3-O-glucoside, delphinidin-3-O-(6-O-acetyl) glucoside and delphinidin-3-O-(6-O-p-coumaroyl) glucoside et al. In conclusion, the optimised pulsed electric fields method can quickly and efficiently extract several kinds of anthocyanins from V. amurensis Rupr. This study promoted the intensive processing of V. amurensis Rupr and widened the practical application of pulsed electric field technology.

Topics: Anthocyanins; Antioxidants; Chemical Fractionation; Chromatography, High Pressure Liquid; Electric Stimulation; Glucosides; Mass Spectrometry; Microscopy, Electron, Scanning; Vitis

Ultrasound-Assisted Extraction (UAE) of total anthocyanins (TA) and phenolics (TP) from Blueberry Wine Pomace (BWP) was optimized using Response Surface Methodology (RSM). A Box-Behnken design was used to predict that the optimized conditions were an extraction temperature of 61.03°C, a liquid-solid ratio of 21.70mL/g and a sonication time of 23.67min. Using the modeled optimized conditions, the predicted and experimental yields of TA and TP were within a 2% difference. The yields of TA and TP obtained through the optimized UAE method were higher than those using a Conventional Solvent Extraction (CSE) method. Seven anthocyanins, namely delphinidin-3-O-glucoside, delphindin-3-O-arabinoside, petunidin-3-O-glucoside, cyanidin-3-O-arabinoside, cyanidin-3-O-glucoside, malvidin-3-O-glucoside and malvidin-3-O-arabinoside, were found in the BWP extract from both the UAE and CSE methods.

Topics: Anthocyanins; Blueberry Plants; Food Handling; Glucosides; Phenols; Plant Extracts; Tandem Mass Spectrometry; Ultrasonics; Wine

The present study investigated the underlying mechanism associated with the hypocholesterolemic activity of blueberry anthocyanins by examining its effect on fecal sterol excretion and gene expression of major receptors, enzymes, and transporters involved in cholesterol metabolism.. Hamsters were divided into three groups and fed a 0.1 % cholesterol diet containing 0 % (CTL), 0.5 % (BL), and 1.0 % (BH) blueberry anthocyanins, respectively, for six weeks. Plasma total cholesterol (TC), triacylglycerols (TAG), and non-high-density lipoproteins cholesterol (non-HDL-C) were measured using the enzymatic kits, and the gene expression of transporters, enzymes, and receptors involved in cholesterol absorption and metabolism was quantified using the quantitative PCR. GC analysis was used to quantify hepatic cholesterol and fecal acidic and neutral sterols.. Dietary supplementation of 0.5 and 1.0 % blueberry anthocyanins for 6 weeks decreased plasma TC concentration by 6-12 % in a dose-dependent manner. This was accompanied by increasing the excretion of fecal neutral and acidic sterols by 22-29 % and 41-74 %, respectively. Real-time PCR analyses demonstrated that incorporation of blueberry anthocyanins into diet down-regulated the genes of NPC1L1, ACAT-2, MTP, and ABCG 8. In addition, blueberry anthocyanins were also able to down-regulate the gene expression of hepatic HMG-CoA reductase.. The cholesterol-lowering activity of blueberry anthocyanins was most likely mediated by enhancing the excretion of sterols accompanied with down-regulation on gene expression of intestinal NPC1L1, ACAT-2, MTP, and ABCG 8.

Topics: Animals; Anthocyanins; Anticholesteremic Agents; ATP-Binding Cassette Transporters; Blueberry Plants; Carrier Proteins; Cricetinae; Feces; Fruit; Glucosides; Hydroxymethylglutaryl CoA Reductases; Hypercholesterolemia; Intestine, Small; Liver; Male; Mesocricetus; Phytotherapy; Plant Extracts; Sterol O-Acyltransferase; Sterol O-Acyltransferase 2; Sterols

Flavonoids present in skin extracts of red seedless table grape varieties Summer Royal, Autumn Royal, and Crimson, and white seedless varieties Carati and Thompson were analyzed by HPLC-DAD-MS, in 3 y of study (2006 to 2008). The anthocyanins, delphinidin-3-O-glucoside, cyanidin-3-O-glucoside, petunidin-3-O-glucoside (with their corresponding p-coumaroyl derivatives), peonidin-3-O-glucoside, and malvidin-3-O-glucoside (with their corresponding acetyl, caffeoyl, and p-coumaroyl derivatives) were found. In addition the flavonols quercetin-3-O-glucuronide, quercetin-3-O-rutinoside, quercetin-3-O-glucoside, kaempferol-3-O-glucoside, kaempferol-3-O-galactoside, and the flavan-3-ols procyanidin B1, procyanidin B2, and catechin were also detected. Anthocyanins were the main flavonoids in red grapes ranging from 24 (Crimson) to 500 (Summer Royal) mg/kg fresh weight of grapes; consistent levels of flavonols and flavan-3-ols were also quantified in all varieties. To determine the effective climatic influence on flavonoids content in field conditions, viticultural practices have been developed, that could exclude the effects of direct solar radiation from confounding the assessment of those related to thermal conditions alone. A strong positive correlation was determined between flavonoids and temperature data that seem to be responsible for the difference of these metabolites along the years; furthermore, it has been possible to define a linear relationship (R(2) = 0.6871, P = 0.0057) between thermal amplitude and total flavonoids values in the red grapes.. Grapes are economically the most important fruit species in the world and approximately 30% of its production is used as fresh fruit. Because of the very important role of flavonoids in food quality as well as their health-promoting properties, and considering that our experiments were performed along 3 consecutive years, gathered results in this research are quite promising to give a useful information on the flavonoid contents and their evolution in 5 seedless table grapes that are widespread in Mediterranean regions but also in California and South America, and are grown in a viticultural climate (Apulia, South Italy) very close to some regions of Spain, Turkey, Tunisia, and Israel.

Topics: Anthocyanins; Biflavonoids; Catechin; Chromatography, High Pressure Liquid; Flavonoids; Galactosides; Glucosides; Italy; Kaempferols; Linear Models; Monosaccharides; Proanthocyanidins; Quercetin; Vitis

To investigate neuroprotective effects of three major anthocyanins (cyanidin-3-O-glucoside, delphinidin-3-O-glucoside, and petunidin-3-O-glucoside) isolated from the black soybean (Glycine max L.) cv. Cheongja 3 seed coat against H(2)O(2)-induced cell death of human brain neuroblastoma SK-N-SH cells.. Cell viability, reactive oxygen species (ROS) generation, production and expression of heme oxygenase (HO)-1 and inactivation of mitogen-activated protein (MAP) kinase cascades were determined by MTT assay, 2,7-dichlorofluorescein diacetate (DCF-DA) assay, reverse transcriptase polymerase chain reaction (RT-PCR), and western blotting, respectively.. Pretreatment with anthocyanins reduced the cytotoxicity of H(2)O(2) on SK-N-SH cells, dose-dependently reduced the intracellular ROS level and inactivated apoptosis signal-regulating kinase (ASK1, Thr845), p38, and c-Jun N-terminal kinase (JNK) proteins. The HO-1 and Neu1 mRNA levels were increased by H(2)O(2) (25 μM) and further elevated by the pretreatment with anthocyanins. Sialic acids added to the culture plates not only attenuated the cytotoxicity of H(2)O(2) (25 μM) but also reduced intracellular ROS level. These results suggest that Cheongja 3 black soybean seed coat anthocyanins have brain neuroprotective effects against oxidative stress (H(2)O(2)) by inhibiting the activation of ASK1-JNK/p38 pathways, scavenging ROS, stimulating the expression of HO-1 and, more interestingly, recruiting cellular free sialic acids through up-regulation of Neu1 sialidase gene expression.. This is the first report indicating potent health benefits of black soybean seed coat anthocyanins in neuroprotection by triggering mobilization of cellular free sialic acid and utilizing it as an additional biological antioxidant in brain neural cells.

Topics: Anthocyanins; Antioxidants; Cell Death; Cell Line, Tumor; Cell Survival; Gene Expression Regulation; Glucosides; Glycine max; Humans; Hydrogen Peroxide; JNK Mitogen-Activated Protein Kinases; MAP Kinase Kinase Kinase 5; Neuroblastoma; Neuroprotective Agents; Oxidative Stress; p38 Mitogen-Activated Protein Kinases; Reactive Oxygen Species; Sialic Acids

Anthocyanins are naturally occurring polyphenols that impart bright color to fruits, vegetables and plants. In this study, the extraction of anthocyanins from freeze-dried fruit skin of downy rose-myrtle (Rhodomyrtus tomentosa (Ait.) Hassk var. Gangren) was optimized using response surface methodology (RSM). Using 60% ethanol containing 0.1% (v/v) hydrochloric acid as extraction solvent, the optimal conditions for maximum yields of anthocyanin (4.358 ± 0.045 mg/g) were 15.7:1 (v/w) liquid to solid ratio, 64.38 °C with a 116.88 min extraction time. The results showed good fits with the proposed model for the anthocyanin extraction (R(2) = 0.9944). Furthermore, the results of high-performance liquid chromatography-electrospray ionization-mass spectrometry (HPLC-ESI-MS) analysis of the anthocyanins extracted from the fruit skin of downy rose-myrtle revealed the presence of five anthocyanin components, which were tentatively identified as delphinidin-3-glucoside, cyanidin-3-glucoside, peonidin-3-glucoside, petunidin-3-glucoside and malvidin-3-glucoside.

Topics: Anthocyanins; Chromatography, High Pressure Liquid; Fruit; Glucosides; Myrtaceae; Plant Extracts; Spectrometry, Mass, Electrospray Ionization

Anthocyanins belong to a class of flavonoids exhibiting antioxidant and anti-inflammatory actions as well as a variety of chemotherapeutic effects. However, little is known about the cellular and molecular mechanism of anticancer activity. In this study, we investigated if the anthocyanins (delphinidin-3,5-diglucoside: cyanidin-3,5-diglucoside: petunidin-3,5-diglucoside: delphinidin-3-glucoside: malvdin-3,5-diglucoside: peonidin-3,5-diglucoside: cyanidin-3-glucoside: petunidin-3-glucoside: peonidin-3- glucoside: malvidin-3- glucoside = 27:63:8.27:1:2.21:2.21:6.7:1.25:5.72:1.25) [corrected] isolated from meoru (Vitis coignetiae Pulliat) exerted antiproliferative and anti-invasive and apoptotic effects on human hepatoma Hep3B cells. It was found that the anthocyanins could inhibit cell growth by 75% at the concentration of 400 microg/mL for 48 h. Flow cytometric analysis showed that the anthocyanins increased the amount of DNA fragments (sub-G1 fraction) in a dose-dependent manner, which is closely related to mitochondrial dysfunction and reduction in antiapoptotic proteins (Bcl-2, xIAP, cIAP-1, and cIAP-2). The anthocyanins also significantly inhibited the migration and invasion of Hep3B cells through a matrigel-coated chamber. Taken together this study indicates that the anthocyanins from meoru have antiproliferative and anti-invasive effects and may induce apoptosis through the activation of the mitochondrial pathway and inhibition of antiapoptotic proteins. This study provides evidence that the anthocyanins isolated from meoru might be useful in the treatment of human hepatitis B-associated hepatoma.

Topics: Anthocyanins; Apoptosis; bcl-2-Associated X Protein; bcl-X Protein; Blotting, Western; Carcinoma, Hepatocellular; Cell Line, Tumor; Cell Movement; DNA Fragmentation; Dose-Response Relationship, Drug; Flow Cytometry; Glucosides; Humans; Inhibitor of Apoptosis Proteins; Liver Neoplasms; Membrane Potential, Mitochondrial; Neoplasm Invasiveness; Proto-Oncogene Proteins c-bcl-2; Reverse Transcriptase Polymerase Chain Reaction; Vitis; X-Linked Inhibitor of Apoptosis Protein

The inhibitory effect of anthocyanins has been investigated in the peroxidation of linoleic acid in micelles in the presence and in the absence of (+)-catechin. The peroxidation was initiated by thermal decomposition of 2,2(')-azobis[2-(2-imidazolin-2-yl)propane], and the kinetics of peroxidation were followed by measuring the rate of oxygen consumption and the rate of disappearance of the antioxidant. The analysis of the antioxidant effect of various anthocyanins, alone or in the presence of catechin, demonstrates that catechin, which is relatively inefficient at inhibiting linoleic acid oxidation, regenerates the highly efficient antioxidant malvidin 3-glucoside and, at a lower extent, peonidin 3-glucoside. The malvidin 3-glucoside recycling by catechin strongly increases the antioxidant efficiency of these two antioxidants. This protective mechanism appears specific for malvidin and peonidin 3-glucosides. The high unpaired spin density of the phenolic O atoms in the radicals generated by these anthocyanins, calculated by the semiempirical quantum chemical AM1 method, may explain the observed behavior.

Topics: Anthocyanins; Antioxidants; Azo Compounds; Catechin; Dose-Response Relationship, Drug; Drug Synergism; Free Radicals; Glucosides; Imidazoles; Inhibitory Concentration 50; Linoleic Acid; Lipid Peroxidation; Lipoproteins, LDL; Micelles; Oxygen