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

The pigmented rice has been consumed in China, Japan, and Korea for a long time. It has been used for strengthening kidney function, treating anemia, promoting blood circulation, removing blood stasis, treating diabetes, and ameliorating sight in traditional Chinese medicine. The extracts from pigmented rice are used as natural food colorants in bread, ice cream, and liquor as well as functional food. The pigmented rice is mainly black, red, and dark purple rice, and contains a variety of flavones, tannin, phenolics, sterols, tocols, γ-oryzanols, amino acids, and essential oils. Anthocyanins are thought as major functional components of pigmented rice. Several anthocyanins have been isolated and identified from the pigmented rice, including cyanidin 3-glucoside, cyanidin 3-galactoside, cyanidin 3-rutinoside, cyanidin 3,5-diglucoside, malvidin 3-galactoside, peonidin 3-glucoside, and pelargonidin 3,5-diglucoside. This review provides up-to-date coverage of pigmented rice in regard to bioactive constituents, extraction and analytical methods, and bioactivities. Special attention is paid to the bioactivities including antioxidant and free radical scavenging, antitumor, antiatherosclerosis, hypoglycemic, and antiallergic activities.

Topics: Animals; Anthocyanins; Anti-Allergic Agents; Anticholesteremic Agents; Antineoplastic Agents; Antioxidants; China; Galactosides; Glucosides; Humans; Hypoglycemic Agents; Japan; Oryza; Phenols; Pigmentation; Plant Extracts; Republic of Korea

Formation of advanced glycation end products (AGEs), which are associated with diabetes mellitus, contributes to prominent features of osteoarthritis, i.e., inflammation-mediated destruction of articular cartilage. Among the phytochemicals which play a role in anti-inflammatory effects, anthocyanins have also been demonstrated to have anti-diabetic properties. Purple corn is a source of three major anthocyanins: cyanidin-3-O-glucoside, pelargonidin-3-O-glucoside and peonidin-3-O-glucoside. Purple corn anthocyanins have been demonstrated to be involved in the reduction of diabetes-associated inflammation, suggesting that they may have a beneficial effect on diabetes-mediated inflammation of cartilage. This investigation of the chondroprotective effects of purple corn extract on cartilage degradation found a reduction in glycosaminoglycans released from AGEs induced cartilage explants, corresponding with diminishing of uronic acid loss of the cartilage matrix. Investigation of the molecular mechanisms in human articular chondrocytes showed the anti-inflammatory effect of purple corn anthocyanins and the metabolite, protocatechuic acid (PCA) on AGEs induced human articular chondrocytes via inactivation of the NFκb and MAPK signaling pathways. This finding suggests that purple corn anthocyanins and PCA may help ameliorate AGEs mediated inflammation and diabetes-mediated cartilage degradation.

Topics: Anthocyanins; Cartilage; Cell Line; Chondrocytes; Diabetes Complications; Diabetes Mellitus; Glucosides; Glycation End Products, Advanced; Glycosaminoglycans; Humans; Hydroxybenzoates; Inflammation; MAP Kinase Signaling System; NF-kappa B; Osteoarthritis; Zea mays

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

Two tightly linked genes for rice purple leaf sheath were identified via map-based cloning. Further analysis indicated that these two genes together with OsC1 co-regulating the purple leaf sheath. The purple color of the leaf sheath in rice is dependent on the accumulation of anthocyanins such as cyanidin 3-O-glucoside (C3G) and peonidin 3-O-glucoside (P3G). Although many genes related to leaf sheath color have been mapped, the genetic basis for leaf sheath color is not yet clear. Here, PSH1 (purple leaf sheath 1) was mapped to chromosome 1 using an F

Topics: Anthocyanins; Chromosome Mapping; Genes, Plant; Glucosides; Oryza; Phenotype; Pigmentation; Plant Leaves; Plants, Genetically Modified; Quantitative Trait Loci

1. Anthocyanins are a subgroup of flavonoids responsible for the blue, purple and red color of many fruits, flowers and leaves. Consumption of foods rich in anthocyanins is associated with a reduced risk of cardiovascular disease and cancer. Most food intervention studies employ once or twice per day dose schedules. 2. The current study demonstrated that plasma concentrations of cyanidin-3-galactoside and cyanidin-3-xyloside, the two major components of saskatoon berries, were significantly increased following three consecutive saskatoon berry supplements 4 hours apart. This accumulation is due to the residual concentrations of anthocyanins at the time of second and third supplements. 3. Accumulation was especially pronounced for peonidin-3-glucoside and peonidin-3-galactoside, the methylated metabolites of cyanidin-3-glucoside and cyanidin-3-galactoside, respectively. Little or no accumulation was observed for cyanidin-3-arabinoside and cyanidin-3-glucoside, two other components of saskatoon berries, possibly due to their short half-lives. 4. Thus, taking anthocyanin supplements with every meal would provide higher plasma concentrations for some anthocyanins and their metabolites than the once or twice-a-day dose regimens.

Topics: Anthocyanins; Dietary Supplements; Galactosides; Glucosides; Humans; Plasma; Rosaceae

Paramagnetic species (radicals) related pigments in Thai purple rice were investigated by electron paramagnetic resonance (EPR), X-band (9 GHz) EPR imaging (EPRI), and HPLC. The location and distribution of the paramagnetic species in purple and white rice were determined by EPR and EPRI. EPR primarily detected three paramagnetic species in purple rice, which were identified as organic radicals, Mn

Topics: Anthocyanins; Chromatography, High Pressure Liquid; Electron Spin Resonance Spectroscopy; Glucosides; Oryza; Pigmentation; Pigments, Biological; Thailand

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

This study aimed to investigate the associations between phenolic composition of selected purple maize genotypes and their anti-inflammatory, anti-adipogenic and anti-diabetic properties in vitro. Anthocyanin-rich water extracts (PMWs) from 20 purple maize genotypes were evaluated in RAW 264.7 macrophages and 3T3-L1 adipocytes under different conditions. Cyanidin-3-O-glucoside (C3G), pelargonidin-3-O-glucoside (Pr3G), peonidin-3-O-glucoside (P3G) and corresponding acylated forms were major anthocyanins in PMW, accompanied by ten tentatively identified non-anthocyanin phenolics. Correlation studies showed that C3G, P3G, and derivatives, but not Pr3G and its acylated form contributed to the biological properties of PMW. Besides anthocyanins, quercetin, luteolin, and rutin were the dominant anti-inflammatory and anti-diabetic components, in terms of down-regulating pro-inflammatory mediator production in inflamed macrophages and adipocytes, modulating diabetes-related key enzymes and improving insulin sensitivity in insulin-resistant adipocytes. Quercetin and phenolic acids, especially vanillic acid and protocatechuic acid, were closely associated with anti-adipogenic properties of PMW via inhibition of the preadipocyte-adipocyte transition.

Topics: 3T3-L1 Cells; Adipocytes; Adipogenesis; Animals; Anthocyanins; Anti-Inflammatory Agents; Cell Differentiation; Genotype; Glucosides; Hypoglycemic Agents; Insulin Resistance; Mice; Phenols; Plant Extracts; Principal Component Analysis; RAW 264.7 Cells; Reactive Oxygen Species; Tumor Necrosis Factor-alpha; Zea mays

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

In this study, the anthocyanin from Lonicera caerulea 'Beilei' fruit (ABL) was extracted and purified. The purified component (ABL-2) was then evaluated for its anti-tumor properties on human hepatoma cells (SMMC-7721) in vitro and the murine hepatoma cells (H22) in vivo. In vitro, ABL-2 not only significantly inhibited the growth of SMMC-7721 cells, but also remarkably blocked the cells' cycle in G2/M phase, inducing DNA damage and eventually leading to apoptosis. In vivo, ABL also killed tumor cells, inhibited tumor growth, and improved the survival status of H22 tumor-bearing mice. These effects were associated with an increase in the activities of antioxidase and a decrease in the level of lipid peroxidation, as evidenced by changes in SOD, GSH-Px, GSH, and MDA levels. In addition, ABL-2 also regulated the levels of immune cytokines including IL-2, IFN-γ, and TNF-α. These results revealed that ABL-2 exerts an effective anti-tumor effect by dynamically adjusting the REDOX balance and improving the immunoregulatory activity of H22 tumor-bearing mice. High performance liquid chromatography (HPLC) analysis revealed that cyanidin-3,5-diglucoside (8.16 mg/g), cyanidin-3-glucoside (387.60 mg/g), cyanidin-3-rutinoside (23.62 mg/g), and peonidin-3-glucoside (22.20 mg/g) were the main components in ABL-2, which may contribute to its anti-tumor activity.

Topics: Animals; Anthocyanins; Antineoplastic Agents; Antioxidants; Apoptosis; Carcinoma, Hepatocellular; Cell Line, Tumor; Cytokines; DNA Damage; Fruit; G2 Phase Cell Cycle Checkpoints; Glucosides; Humans; Lipid Peroxidation; Liver Neoplasms; Lonicera; Male; Mice; Plant Extracts

We investigated the pigments in Thai purple rice using electron paramagnetic resonance (EPR), X-band (9 GHz) EPR imaging (EPRI), and HPLC. The location and spatial distribution of the paramagnetic species in purple and white rice were determined by EPR and EPRI. EPR primarily detected three paramagnetic species in purple rice, which were identified as stable radicals, Mn

Topics: Anthocyanins; Chromatography, High Pressure Liquid; Coloring Agents; Electron Spin Resonance Spectroscopy; Glucosides; Iron; Manganese; Oryza; Thailand

Purple sweet potato was fermented into alcoholic beverage. By using LC-MS analysis, 12 types of anthocyanins were found in the purple sweet potato alcoholic beverage (PSPFAB); these were based on cyanidin and peonidin as aglycones. The anthocyanins in young PSPFAB mainly consisted of acylates. The acylated anthocyanins, however, degraded gradually with aging. Cyanidin 3-sophoroside-5-glucoside and peonidin 3-sophoroside-5-glucoside were found to be major anthocyanins in the PSPFAB after two years of aging. Moreover, 52 kinds of volatile components were detected in PSPFAB by GC-MS analysis. Alcohol and ester substances constituted a major proportion of these volatile components of PSPFAB. After two years of aging, levels of high-alcohols such as 1-pentanol remarkably decreased to below the detection limit, while the level of total esters increased significantly. Such variation of aromas enriched and improved the flavor of PSPFAB.

Topics: Alcoholic Beverages; Anthocyanins; Chromatography, Liquid; Fermentation; Food Analysis; Food Handling; Glucosides; Ipomoea batatas; Mass Spectrometry; Plant Extracts; Volatile Organic Compounds

The objectives of this study were to systematically analyze degradation rate of functional substances, such as total phenolic content (TPC), total flavonoid content (TFC), condensed tannin content (CTC), monomeric anthocyanin content (MAC), cyanidin-3-glucoside (Cy3glc), and peonidin-3-glucoside (Pn3glc), as well as antioxidant activities in cooked waxy and non-waxy black rice through different home cooking manners. Results showed that greater phenolics and antioxidant capacities were detected in non-waxy rice rather than waxy one. All processed black rice exhibited significantly (p<0.05) lower TPC, TFC, CTC, MAC, Cy3glc, Pn3glc, and antioxidants as compared to the raw rice. Different processing methods significantly degraded the content and activities of antioxidants of both waxy and non-waxy black rice. Under the same cooking time, black rice porridge retained more active substances than that of cooked rice by rice cooker. Therefore, to maintain bioavailability of active components, black rice porridge may gain more health promoting effects.

Topics: Anthocyanins; Antioxidants; Color; Cooking; Glucosides; Humans; Oryza; Phenols

The goal of this work was to determine the anthocyanin retention and physicochemical properties of haskap powder prepared by Refractance Window™ (RW) drying. In general, the RW-dried powder particles had a smooth surface with similar thickness, consistent with the preparation method, and had a solubility of 75.63% in water. The RW-dried powder (consisting of 98% haskap berries) retained approximately 93.8% of anthocyanins from the original frozen fruits, as assessed by the pH-differential method. This result is in good agreement with HPLC analysis that indicated 92.9% retention. Three anthocyanins were identified in frozen berries and RW-dried powder: cyanidin 3-glucoside, cyanidin 3-rutinoside, and peonidin 3-glucoside. Surprisingly, cyanidin 3-rutinoside exhibited the lowest retention.

Topics: Anthocyanins; Chemical Phenomena; Chromatography, High Pressure Liquid; Fruit; Glucosides

Anthocyanin-rich blue corn is an emerging specialty crop in the USA. The antioxidant properties of blue corn offer health benefits in the human diet. The objectives of this study were to identify, characterize and quantify the anthocyanins from blue corn. Hypotheses tested were that total anthocyanin content was similar among southwestern US accessions and that it would vary across locations. It was also examined whether different anthocyanin components were unique to certain genotypes.. Across all locations and accessions, an average of 0.43 g kg(-1) total anthocyanin content (TAC) was observed. Accessions Santa Clara Blue and Ohio Blue displayed the highest TAC. The TAC of accession Flor del Rio was lower by nearly a factor of six. A total of five anthocyanin components were identified. Cyanidin 3-glucoside was the most abundant, followed by pelargonidin and peonidin 3-glucoside. Succinyl and disuccinyl glycosidic forms of cyanidin were also identified. Cyanidin 3-disuccinylglucoside was newly identified as a novel form of anthocyanin.. Quantitative and qualitative anthocyanin expression was determined to be relatively stable across multiple southwestern environments. Increased expression of red and purple pigmentation in accession Flor del Rio appeared to be associated more with reduced TAC and cyanidin 3-glucoside than with elevated pelargonidin per se. A previously unreported anthocyanin component in blue corn, cyanidin 3-disuccinylglucoside, is present in southwestern landraces. © 2016 Society of Chemical Industry.

Topics: Altitude; Anthocyanins; Antioxidants; Crop Production; Crops, Agricultural; Food Quality; Functional Food; Glucosides; Humans; Pigments, Biological; Plant Breeding; Principal Component Analysis; Seeds; Southwestern United States; Species Specificity; Succinates; Zea mays

Trastuzumab (Herceptin®) is a recombinant humanized monoclonal antibody that is targeted against the human epidermal growth factor receptor 2 (HER2) tyrosine kinase receptor. Trastuzumab has been successfully used to treat patients with HER2-positive breast cancer, which accounts for ~25% of invasive breast cancer. However, the majority of patients who initially respond to trastuzumab demonstrate disease progression within 1 year of treatment. Therefore, identifying alternative drugs that overcome trastuzumab resistance and target HER2 may increase the magnitude and duration of response. Through a high‑throughput screening approach, we previously identified numerous anthocyanins that exert activity in HER2‑positive human breast cancer cell lines. The present study aimed to evaluate the anti‑tumor properties of anthocyanins against parental HER2‑positive cells and derivative trastuzumab‑resistant cells in vitro and in vivo. Cell proliferation, western blotting, Annexin V staining, migration and invasion assays were used to determine the effects of anthocyanins in vitro. Cyanidin-3-glucoside and peonidin-3-glucoside were able to inhibit phosphorylation of HER2, induce apoptosis, suppress migration and invasion, and inhibit tumor cell growth. Coupled with the fact that anthocyanins have been used for decades as supplements for the treatment of various types of cancer in Asia, the present study may have established a framework for the development and testing of anthocyanins as a novel treatment paradigm used to overcome classical trastuzumab-resistance and to improve the outcome of this disease.

Topics: Animals; Anthocyanins; Apoptosis; Breast Neoplasms; Drug Resistance, Neoplasm; Female; Glucosides; Humans; Mice; Mice, Nude; Trastuzumab; Xenograft Model Antitumor Assays

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

The determination of rate and equilibrium constants of anthocyanin metabolites with in vivo occurrence, cyanidin-4'-O-methyl-3-glucoside (Cy4'Me3glc) and cyanidin-7-O-glucuronyl-3-glucoside (Cy7Gluc3glc), was carried out for the first time by means of direct and reverse pH jumps. The thermodynamics and kinetics of these compounds are similar to the anthocyanin monoglucosides in particular for the analogous cyanidin-3-glucoside (Cy3glc) and peonidin-3-glucoside (Peo3glc). The rate and equilibrium constants of metabolites were also compared with malvin (malvidin 3,5-diglucoside) and with a bioinspired compound 3',4'-dihydroxy-7-O-glucopyranosyloxyflavylium (DGF). In Cy4'Me3glc and Cy7Gluc3glc the rate of hydration for a fixed pH value is slower than in DGF and the dominant species at moderately acidic solutions is the hemiketal. Oppositely, in DGF trans-chalcone is the dominant species at moderately acidic solutions.

Topics: Anthocyanins; Chromatography, High Pressure Liquid; Glucosides; Hydrogen-Ion Concentration; Kinetics; Spectrometry, Mass, Electrospray Ionization; Spectrophotometry, Ultraviolet; Thermodynamics

Juçara (Euterpe edulis M.) fruits are an interesting source of phenolic compounds, mainly anthocyanins, making them valuable to the food and pharmaceutical industries. Juçara fruits were harvested along the on-tree ripening process between March and June as practiced in Paraná state, Brazil and examined for their total anthocyanin content (TAC), total phenolic content (TPC), total phenolic acid (TPA) and total antioxidant capacity (TAA). Overall, TAC increased (91.52-236.19 mg cyanidin-3-glucoside equivalent/100 g dm) whereas TPC (81.69-49.09 mg GAE/g dm) and TPA (44.27-30.95 mg/100 g dm) decreased during ripening of juçara fruits. Use of tandem mass spectrometry allowed the identification of cyanidin-3,5-diglucoside, peonidin-3-glucoside and peonidin-3-rutinoside for the first time in juçara fruits. The analysis of the phenolic acids by HPLC-MS/MS indicated the presence of gallic, protocatechuic, p-hydroxybenzoic, vanillic, chlorogenic, caffeic, syringic, p-coumaric, sinapinic and ferulic acids. The high antioxidant capacity using DPPH radical scavenging capacity (655.89-745.32 μmol TE/g dm) and ORAC assays (1088.10-2071.55 μmol TE/g dm) showed that juçara fruits have potential as a source of novel natural antioxidants for disease prevention and health promotion, and also as natural food additives for developing new functional food products.

Topics: Anthocyanins; Antioxidants; Caffeic Acids; Carboxylic Acids; Euterpe; Fruit; Glucosides; Hydroxybenzoates

Human epidermal growth factor receptor 2 (HER2) has been found to be overexpressed in ~25% of invasive breast cancer and is significantly associated with a poor prognosis in breast cancer patients. The anthocyanins cyanidin-3-glucoside (C3G) and peonidin-3-glucoside have been identified as potential drugs for the therapy of HER2‑positive breast cancer. They have been used as supplements in targeted therapeutics and chemotherapeutics in Asia, however, the underlying mechanism remains to be elucidated. The aim of the present study was to investigate the synergism between C3G and trastuzumab (Trast). To address this question, the response to C3G, Trast and a combination of the two drugs, in three representative HER2‑positive cell lines was evaluated. The combination treatments induced apoptosis, inhibited cell growth and affected HER2 and its downstream signaling pathway in MDA‑MB‑453, BT474 and HCC1569 cells, and the effects were synergistic. The combination of 3CG and Trast inhibited tumor growth in an in vivo xenograft model. The data from the present study suggested that C3G exhibits potent antitumor activity when combined with Trast under the investigated conditions.

Topics: Animals; Anthocyanins; Antibodies, Monoclonal, Humanized; Antineoplastic Agents; Apoptosis; Breast Neoplasms; Cell Line, Tumor; Drug Synergism; Female; Glucosides; Humans; Kidney; Liver; Mice; Mice, Nude; Mitogen-Activated Protein Kinase 1; Mitogen-Activated Protein Kinase 3; Proto-Oncogene Proteins c-akt; Receptor, ErbB-2; Spleen; Transplantation, Heterologous; Trastuzumab

Purple rice (Oryza sativa L. var. indica) cv. Kum Doisaket is cultivated in northern Thailand. This study evaluated the mutagenic and antimutagenic properties of hydrophilic and lipophilic components of purple rice using the Ames test. The seed and hull of purple rice were extracted with hexane, methanol, ethanol, and water. The methanol extracts had the highest amounts of phenolic acids and flavonoids, while the hexane extracts contained large amount of tocols and γ-oryzanol. None of the extracts were mutagenic in Salmonella typhimurium strains TA98 and TA100. The hexane extract of rice hull and the methanol extract of rice seed were strongly effective against aflatoxin B1- and 2-amino-3, 4 dimethylimidazo (4, 5-f) quinoline-induced mutagenesis, while aqueous extracts showed weakly antimutagenic properties. All extracts with the exception of aqueous extracts enhanced the number of revertant colonies from benzo (a) pyrene induced-mutagenesis. None of the extracts inhibited mutagenesis induced by the direct mutagens 2-(2-furyl)-3-(5-nitro-2-furyl)-acrylamide and sodium azide. The hull extracts showed more potent antimutagenicity than the seed extracts. Based on a chemical analysis, γ-oryzanol and γ-tocotrienol in the hull and cyanidin-3-glucoside and peonidin-3-glucoside in the seed are candidate antimutagens in purple rice. The antimutagenic mechanisms of purple rice might be related to either modulation of mutagen metabolizing enzymes or direct attack on electrophiles. These findings supported the use of Thai purple rice as a cancer chemopreventive agent.

Topics: Anthocyanins; Antimutagenic Agents; Flavonoids; Glucosides; Hydrophobic and Hydrophilic Interactions; Mutagenicity Tests; Mutagens; Oryza; Phenylpropionates; Plant Extracts; Salmonella typhimurium; Seeds; Thailand

Petals from different rose (Rosa centifolia) cultivars ("passion," "pink noblesse," and "sphinx") were assessed for antimutagenicity using Escherichia coli RNA polymerase B (rpoB)-based Rif (S) →Rif (R) (rifampicin sensitive to resistant) forward mutation assay against ethyl methanesulfonate (EMS)-induced mutagenesis. The aqueous extracts of rose petals from different cultivars exhibited a wide variation in their antimutagenicity. Among these, cv. "passion" was found to display maximum antimutagenicity. Upon further fractionation, the anthocyanin extract of cv. "passion" displayed significantly higher antimutagenicity than its phenolic extract. During thin-layer chromatography (TLC) analysis, the anthocyanin extract got resolved into 3 spots: yellow (Rf : 0.14), blue (Rf : 0.30), and pink (Rf : 0.49). Among these spots, the blue one displayed significantly higher antimutagenicity than the other 2. Upon high-performance liquid chromatography analysis, this blue spot further got resolved into 2 peaks (Rt : 2.7 and 3.8 min). The 2nd peak (Rt : 3.8 min) displaying high antimutagenicity was identified by ESI-IT-MS/MS analysis as peonidin 3-glucoside, whereas less antimutagenic peak 1 (Rt : 2.7) was identified as cyanidin 3, 5-diglucoside. The other TLC bands were also characterized by ESI-IT-MS/MS analysis. The least antimutagenic pink band (Rf : 0.49) was identified as malvidin 3-acetylglucoside-4-vinylcatechol, whereas non-antimutagenic yellow band (Rf : 0.14) was identified as luteolinidin anthocyanin derivative. Interestingly, the anthocyanin extracted from rose tea of cv. "passion" exhibited a similar antimutagenicity as that of the raw rose petal indicating the thermal stability of the contributing bioactive(s). The findings thus indicated the health protective property of differently colored rose cultivars and the nature of their active bioingredients.

Topics: Anthocyanins; Antimutagenic Agents; Chromatography, High Pressure Liquid; Chromatography, Thin Layer; Escherichia coli; Ethyl Methanesulfonate; Glucosides; Mutagenesis; Plant Extracts; Polyphenols; Rosa; Tandem Mass Spectrometry

To observe the inhibitive effects of black rice pericarp extracts on cell proliferation of human prostate cancer cell PC-3 and to explore its effecting mechanism.. The black rice pericarp extract was used to treat the PC-3 cells. The inhibitory effect of black rice pericarp extract on cells proliferation of PC-3 was tested by MTT method. Cell apoptosis rates and cell cycle were measured by flow cytometric assay (FCM). Western blot was used to study the protein expression levels of p38, p-p38, JNK, p-JNK.. A dose-dependent and time-dependent proliferation inhibition of black rice pericarp extract was demonstrated in PC-3. The most prominent experiment condition was inhibitory concentration with 300microg/ml and treated for 72 h. The experiment result of flow cytometry analysis demonstrates that the apoptosis rate of PC-3 cells increased along with the increasing of black rice pericarp extract concentration, and a G1-S cell cycle arrest was induced in a dose-dependent manner. After PC-3 cell was treated with black rice pericarp extract for 72 h, the expressions of p-p38, p-JNK protein increased.. Black rice pericarp extract could inhibit proliferation, change the cell cycle distributions and induce apoptosis in human prostatic cancer cell PC-3. Its inhibitory effect may be through promoting activation of the JNK, p38 signaling pathway. These results suggest that black rice pericarp extract maybe has an inhibitory effect on prostatic cancer.

Topics: Anthocyanins; Antineoplastic Agents; Apoptosis; Cell Line, Tumor; Cell Proliferation; Glucosides; Humans; Male; Oryza; Plant Extracts; Prostatic Neoplasms

Purple corn color is a widely used food colorant that was reported to have attenuating effects on hypertension, diabetes, and to have anti-cancer effects on colon and breast cancer. Our study is the first on its possible chemoprevention effects against prostate cancer. For this purpose an androgen-dependent prostate cancer cell line, LNCaP, was used to examine effects in vitro. Purple corn color inhibited the proliferation of LNCaP cells by decreasing the expression of Cyclin D1 and inhibiting the G1 stage of the cell cycle. Thirty-six male transgenic rats for adenocarcinoma of prostate were fed basic diet or diet with purple corn color for 8 weeks. Purple corn color decreased the incidence of adenocarcinoma in the lateral prostate and slowed down the progression of prostate cancer. A lower Ki67 positive rate, a decrease of the expression of Cyclin D1, and downregulation of the activation of Erk1/2 and p38 MAPK were observed in the group consuming purple corn color in the diet. Since purple corn color is a mixture, determining its active component should help in the understanding and usage of purple corn color for prostate cancer chemoprevention. Therefore, the three major anthocyanins in purple corn color, cyanidin-3-glucoside, pelargonidin-3-glucoside and peonidin-3-glucoside, were tested with LNCaP cells. The results suggested that cyanidin-3-glucoside and pelargonidin-3-glucoside are the active compounds.

Topics: Adenocarcinoma; Animals; Animals, Genetically Modified; Anthocyanins; Cell Cycle; Cell Proliferation; Food Coloring Agents; Glucosides; Male; Prostatic Neoplasms; Rats

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

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 have been studied as potential antimicrobial agents against Helicobacter pylori. We investigated whether the biosynthesis and secretion of cytotoxin-associated protein A (CagA) and vacuolating cytotoxin A (VacA) could be suppressed by anthocyanin treatment in vitro. H. pylori reference strain 60190 (CagA(+)/VacA(+)) was used in this study to investigate the inhibitory effects of anthocyanins; cyanidin 3-O-glucoside (C3G), peonidin 3-O-glucoside (Peo3G), pelargonidin 3-O-glucoside (Pel3G), and malvidin 3-O-glucoside (M3G) on expression and secretion of H. pylori toxins. Anthocyanins were added to bacterial cultures and Western blotting was used to determine secretion of CagA and VacA. Among them, we found that C3G inhibited secretion of CagA and VacA resulting in intracellular accumulation of CagA and VacA. C3G had no effect on cagA and vacA expression but suppressed secA transcription. As SecA is involved in translocation of bacterial proteins, the down-regulation of secA expression by C3G offers a mechanistic explanation for the inhibition of toxin secretion. To our knowledge, this is the first report suggesting that C3G inhibits secretion of the H. pylori toxins CagA and VacA via suppression of secA transcription.

Topics: Anthocyanins; Antigens, Bacterial; Bacterial Proteins; Gene Expression Regulation, Bacterial; Glucosides; Helicobacter pylori; Humans

The effect of white and black rice consumption on lipid profile, hydroperoxides, thiobarbituric reactive substances and oxidized low-density lipoprotein (LDL) induced by hypercholesterolemia was investigated in 24 male rabbits; a purified normal diet (NC, n = 6), a high fat/cholesterol (1.0 g/100 g) diet (PC group, n = 6), a high fat/cholesterol diet with 25 g/100 g white ground rice (PCWR group, n = 6), 25 g/100 g black ground rice (PCBR group, n = 6) for 10 weeks. Blood samples were collected for lipid measurements. Results indicate that serum high-density lipoprotein-cholesterol was higher (P < 0.05) in the PCBR compared with the PC and PCWR groups. Hydroperoxides and thiobarbituric reactive substances were significantly lower (P < 0.05) in the PCBR compared with PCWR and PC groups. Cyanidin-3-glucoside (Cy-3-Glu) and peonidin-3-glucoside have been tested in vitro against copper-mediated low-density lipoprotein. Cy-3-Glu was excelled peonidin-3-glucoside by increasing the lag time of NC from 80 to 500 minutes in the presence of 2.0 μM of Cy-3-Glu. Hierarchically, black rice rabbits group was given the best results compared with other groups. The results may be indicating to a suggested mechanism (anthocyanins protection; Cy-3-Glu) of the cardioprotective effect of black rice.

Topics: Animals; Anthocyanins; Cholesterol, Dietary; Cholesterol, HDL; Dietary Fats; Glucosides; Lipid Metabolism; Lipid Peroxidation; Lipid Peroxides; Lipids; Lipoproteins, LDL; Male; Models, Animal; Oryza; Oxidation-Reduction; Rabbits; Thiobarbituric Acid Reactive Substances

To asses the hypothesis that anthocyanins are rapidly taken up from the blood into tissues, where they accumulate up to their bioactivity threshold, an intravenous dose of cyanidin 3-glucoside (1) was administered to anaesthetized rats. Cyanidin 3-glucoside (1) and its metabolites were analyzed in the plasma, kidneys, liver, urine, and bile, using last-generation mass spectrometry. Compound 1 was found to rapidly disappear from plasma (t/2=0.36 min). As soon as 15 s after its administration, both 1 and its methylation product, peonidin 3-glucoside (2), were detected in the plasma, kidneys, and liver. At 1 min, both 1 and 2 had almost disappeared from the plasma, but attained their peak concentrations in the kidneys and in the liver. Compound 2 was rapidly excreted both in the bile and in the urine. Three additional methylated metabolites were detected in traces, namely, delphinidin 3-glucoside (3), petunidin 3-glucoside (4), and malvidin 3-glucoside (5). These data contribute to solving the paradox of the high bioactivity of anthocyanins in spite of their apparent low bioavailability.

Topics: Animals; Anthocyanins; Bile; Glucosides; Kidney; Liver; Molecular Structure; Rats

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

Tumor metastasis is the most important cause of cancer death and various treatment strategies have targeted on preventing the occurrence of metastasis. Anthocyanins are natural colorants belonging to the flavonoid family, and are wildly used for their antioxidant properties. Here, we provided molecular evidence associated with the anti-metastatic effects of peonidin 3-glucoside and cyanidin 3-glucoside, major anthocyanins extracted from black rice (Oryza sativa L. indica), by showing a marked inhibition on the invasion and motility of SKHep-1 cells. This effect was associated with a reduced expression of matrix metalloproteinase (MMP)-9 and urokinase-type plasminogen activator (u-PA). Peonidin 3-glucoside and cyanidin 3-glucoside also exerted an inhibitory effect on the DNA binding activity and the nuclear translocation of AP-1. Furthermore, these compounds also exerted an inhibitory effect of cell invasion on various cancer cells (SCC-4, Huh-7, and HeLa). Finally, anthocyanins from O. sativa L. indica (OAs) were evidenced by its inhibition on the growth of SKHep-1 cells in vivo.

Topics: Animals; Anthocyanins; Cell Adhesion; Cell Movement; Cell Survival; Electrophoretic Mobility Shift Assay; Glucosides; HeLa Cells; Humans; Male; Matrix Metalloproteinase 9; Matrix Metalloproteinase Inhibitors; Mice; Mice, Inbred BALB C; Mice, Nude; Neoplasms, Experimental; NF-kappa B; Oryza; Specific Pathogen-Free Organisms; Transcription Factor AP-1; Urokinase-Type Plasminogen Activator

Dietary polyphenols, including anthocyanins, are suggested to be involved in the protective effects of fruits and vegetables against cancer. However, anticancer effects of peonidin 3-glucoside have not been clearly demonstrated, with only limited studies being available concerning the inhibitory effect of cyanidin 3-glucoside for tumor cell growth. Therefore, in this study, we have isolated and identified the two bioactive compounds, peonidin 3-glucoside and cyanidin 3-glucoside, from Oryza sativa L. indica, to treat various cancer cells. The results showed that, among analyzed cell lines, HS578T was the most sensitive to peonidin 3-glucoside and cyanidin 3-glucoside. Treatment with peonidin 3-glucoside or cyanidin 3-glucoside resulted in a strong inhibitory effect on cell growth via G2/M arrest. Regarding cell cyclerelated proteins, peonidin 3-glucoside treatment resulted in down-regulation of protein levels of cyclin-dependent kinase (CDK)-1, CDK-2, cyclin B1, and cyclin E, whereas cyanidin 3-glucoside could decrease the protein levels of CDK-1, CDK-2, cyclin B1, and cyclin D1. In addition, cyanidin 3-glucoside or peonidin 3-glucoside also induced caspase-3 activation, chromatin condensation, and cell death. Furthermore, anthocyanins from O. sativa L. indica were evidenced by their inhibition on the growth of Lewis lung carcinoma cells in vivo.

Topics: Animals; Anthocyanins; Antineoplastic Agents; Apoptosis; Blotting, Western; Carcinoma, Lewis Lung; Cell Cycle; Cell Line, Tumor; Cell Survival; Dose-Response Relationship, Drug; Glucosides; Humans; Male; Mice; Mice, Inbred C57BL; Neoplasms; Oryza; Time Factors

Anthocyanins are natural pigments that possess antioxidant activities and are implicated in various health effects. Recent studies showed that the stomach is a site of anthocyanin absorption. However, the fate of anthocyanins in the small intestine remains unknown. We therefore investigated anthocyanin absorption after in situ perfusion of the jejunum + ileum in rats. The intestine was perfused for 45 min with a physiological buffer supplemented with various anthocyanins. Purified anthocyanin glycosides (9.2 nmol/min) or blackberry (9.0 nmol/min) or bilberry (45.2 nmol/min) anthocyanins were perfused. A high proportion of anthocyanin glycosides was absorbed through the small intestine after perfusion. The rate of absorption was influenced by the chemical structure of the anthocyanin and varied from 10.7 (malvidin 3-glucoside) to 22.4% (cyanidin 3-glucoside). Regardless of the anthocyanins perfused, only glycosides were recovered in the intestinal lumen. After perfusion of a high amount of blackberry anthocyanins (600 nmol/min), native cyanidin 3-glucoside was recovered in urine and plasma from the aorta and mesenteric vein. Methylated and/or glucuronidated derivatives were also identified. Analysis of bile samples revealed that cyanidin 3-glucoside and its methylated derivatives (peonidin 3-glucoside + peonidin glucuronide) quickly appeared in bile. This study demonstrated that anthocyanin glycosides are rapidly and efficiently absorbed from the small intestine. Furthermore, anthocyanins are quickly metabolized and excreted into bile and urine as intact glycosides as well as methylated forms and glucuronidated derivatives.

Topics: Animals; Anthocyanins; Bile; Chromatography, High Pressure Liquid; Drug Stability; Fruit; Glucosides; Glucuronides; Glycosides; Ileum; Intestinal Absorption; Intestine, Small; Jejunum; Male; Rats; Rats, Wistar; Vaccinium myrtillus

Jasmonic acid altered the accumulation of major anthocyanins in Vitis vinifera cell culture. Peonidin 3-glucoside content at day three was increased from 0.3 to 1.7 mg g(-1) dry cell wt while other major anthocyanins were increased by smaller increments. By day 14, the content of methylated and acylated anthocyanins (peonidin 3-p-coumaroylglucoside and malvidin 3-p-coumaroylglucoside) was 6.3 mg g(-1) DCW, in response to treatment with jasmonic acid, and comprising approximately 45% (w/w) of total anthocyanins. In comparison, the untreated control culture contained 1.2 mg g(-1) DCW which made up approximately 32% (w/w) of total anthocyanins. Light further enhanced anthocyanin accumulation induced by jasmonic acid elicitation. The content of peonidin 3-glucoside at day 3 was 6.6 mg g(-1) DCW, 22-fold higher than control cultures while the content in response to light irradiation alone was 0.6 mg g(-1) DCW. When a highly pigmented cell line was elicited with jasmonic acid total anthocyanins increased from 9.2 to 20.7 mg g(-1) DCW, but there was no change in the anthocyanin composition.

Topics: Anthocyanins; Cell Culture Techniques; Cell Line; Chromatography, High Pressure Liquid; Cyclopentanes; Glucosides; Light; Oxylipins; Pigments, Biological; Vitis

After consumption, anthocyanins are rapidly absorbed as glycosides. Their rapid appearance in plasma could result from absorption through the gastric wall. The aim of this study was to evaluate the fate of anthocyanins in the stomach. Absorption of purified anthocyanins (14 micromol/L) as well as blackberry 14 and 750 micromol/L) and bilberry (88 micromol/L) anthocyanins was compared after in situ gastric administration for 30 min. A high proportion (approximately 25%) of anthocyanin monoglycosides (glucoside or galactoside) was absorbed from the stomach, whereas absorption of cyanidin 3-rutinoside was lower. Bilberry anthocyanins were also efficiently absorbed, but absorption varied greatly (19-37%) according to the anthocyanin structure; delphinidin glycosides were the most absorbed. When a high concentration of blackberry anthocyanins (750 micromol/L) was injected into the gastric lumen, the percentage of cyanidin 3-glucoside (Cy 3-glc) absorption was lower than after administration of a low concentration (14 micromol/L). After administration of this high concentration, blackberry anthocyanins were observed in plasma from gastric vein and aorta, whereas neither aglycones nor metabolites were detected. Analysis of bile samples revealed that Cy 3-glc appeared in bile after as little as 20 min. Peonidin 3-glucoside (the methylated form of Cy 3-glc) as well as unknown anthocyanin metabolites were also observed in bile. Thus, this study demonstrated that anthocyanin glycosides were quickly and efficiently absorbed from the stomach and rapidly excreted into bile as intact and metabolized forms.

Topics: Absorption; Animals; Anthocyanins; Aorta; Bile; Fruit; Gastric Mucosa; Glucosides; Male; Rats; Rats, Wistar; Stomach; Time Factors; Veins