pelargonidin and cyanidin

Diet is an essential factor affecting the development of and risk for diabetes mellitus. In search of preventative and therapeutic strategies, the potential role of certain foods and their bioactive compounds to prevent the pathogenesis associated with metabolic diseases is to be considered. Human consumption of anthocyanins is among the highest of all flavonoids. Epidemiological studies have suggested that the consumption of anthocyanins lowers the risk of diabetes and diabetic complications. Anthocyanins are important natural bioactive pigments responsible for red to blue colour of fruits, leaves, seeds, stems and flowers, which are present in a variety of plant species particularly in berries and cherries. A large number of bioactive anthocyanins, such as cyanidin, malvidin, delphinidin, pelargonidin, peonidin, petunidin and their metabolites have shown multiple biological activities with apparent effects on glucose absorption, glucose uptake, insulin secretion and sensitivity, on the enzymes involved in glucose metabolism, gene expressions, inflammatory mediators, glucose transporters in progression of diabetes and associated complications, such as diabetic retinopathy, nephropathy, neuropathy and diabetic vascular diseases. The versatility of the anthocyanins provides a promising approach for diabetes management than synthetic drugs. Here we summarize the effect of several anthocyanins on many in vitro, in vivo and clinical studies and also reveal the mechanisms which could prevent or reverse the underlying mechanisms of diabetic pathologies including promotion of antioxidant, antihyperlipidemic, anti-inflammatory and anti-apoptotic activities.

Topics: Anthocyanins; Diabetes Mellitus; Diet; Fruit; Humans; Hydroxybenzoates; Oxidative Stress

Topics: Anthocyanins; Phenols

Thirteen anthocyanins were isolated from the flowers of two Aeschynanthus species, A. fulgens and A. pulcher, and six cultivars, 'Mahligai', 'Mona Lisa', 'SoeKa', 'Redona', 'Freshya' and 'Bravera', and identified as pelargonidin and cyanidin 3-O-sambubiosides and their malonates, succinates, p-coumarates and caffeates, and pelargonidin 3-O-glucoside by acid hydrolysis, HR-MS and NMR. Of their anthocyanins, pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-malonylglucoside)] (2), pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-succinylglucoside)] (3), pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-E-p-coumaroylglucoside)] (4), pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-Z-p-coumaroylglucoside)] (5), pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-E-caffeoylglucoside)] (6) and cyanidin 3-O-[xylosyl-(1 → 2)-(6''-succinylglucoside)] (9) were reported in nature for the first time.

Topics: Anthocyanins; Disaccharides; Flowers

Anthocyanins are a major source of natural red colorants but currently face difficulties matching the hue range, stability, and affordability of synthetic options. Purple corn offers an FDA and EFSA-approved economical source of anthocyanin-based colorants. A C-glycosyl flavone and anthocyanin copigmentation system consisting of a flavone-rich anthocyanin-poor line and two anthocyanin-rich flavone-poor lines containing either pelargonidin or cyanidin-derived anthocyanins is described. This system offers a broad hue range and can improve stability. Cyanidin-rich model beverages had better stability than pelargonidin-rich beverages over time, but the addition of flavone-rich extract to both resulted in significantly longer half-lives (up to 50% longer). Flavone copigments produced hyperchromic and bathochromic shifts in both. A protective effect from flavone copigmentation was observed for glycosides. In contrast acylated forms displayed significantly shorter half-lives. Results suggest that corn C-glycosyl flavone-rich extracts could serve as a color enhancing and stabilizing agent for anthocyanin colorants.

Topics: Anthocyanins; Beverages; Flavones; Food Coloring Agents; Pigments, Biological; Plant Extracts; Zea mays

Anthocyanins from purple-fleshed sweetpotatoes constitute highly valued natural colorants and functional ingredients. In the past, anthocyanin extraction conditions and efficiencies using a single acidified solvent have been assessed. However, the potential of solvent mixes that can be generated by fermentation of biomass-derived sugars have not been explored. In this study, the effects of single and mixed solvent, time, temperature, sweetpotato genotype and preparation, on anthocyanin and phenolic extraction were evaluated. Results indicated that unconventional diluted solvent mixes containing acetone, butanol, and ethanol were superior or equally efficient for extracting anthocyanins when compared to commonly used concentrated extractants. In addition, analysis of anthocyanidins concentrations including cyanidin (cy), peonidin (pe), and pelargonidin (pl), indicated that different ratios of pn/cy were obtained depending on the solvent used. These results could be useful when selecting processing conditions that better suit particular end-use applications and more environmentally friendly process development for purple sweetpotatoes.

Topics: Acetone; Anthocyanins; Butanols; Chemical Fractionation; Ethanol; Ipomoea batatas; Phenols; Plant Extracts; Solvents

Unsaturated fatty acids (UFA) in milk give rise to radicals and lead to lipid oxidation during storage, reducing the commercial value of milk. The objective of this study was to observe the effect of anthocyanins from purple corn pigment on the oxidation of UFA in milk. Milk samples were randomly divided into 2 groups: (1) the control (without purple corn pigment) and (2) treatment (0.3% purple corn pigment), using a completely randomized design. The milk samples were placed into plastic tubes and stored at 4°C for a period of 0, 1, 3, and 7 d. Individual anthocyanin composition and UFA were detected by HPLC-mass spectrometry and gas chromatography-mass spectrometry, respectively. The results indicated that pelargonidin (0.258 vs. 0.054 µg/mL), cyanidin (5.550 vs. 1.808 µg/mL), petunidin (0.464 vs. 0.107 µg/mL), delphinidin (2.061 vs. 0.123 µg/mL), and total anthocyanin (8.332 vs. 2.091 µg/mL) significantly decreased in response to increasing storage day. Of interest, purple corn pigment had a significant effect on most of the UFA (C14:1n-5, C16:1n-7, C18:1n-9, C18:2n-6, C18:3n-3, C18:3n-6, C20:2n-6, C20:3n-3, and C20:4n-6), except for C17:1n-7 and C20:3n-6. Specifically, various stronger positive correlations were noted for anthocyanin composition and UFA (pelargonidin and petunidin with C14:1n-5, C17:1n-7, C18:2n-6, C20:2n-6, C20:3n-3, and C20:4n-6; and cyanidin and total anthocyanins with C14:1n-5, C16:1n-7, C17:1n-7). Collectively, the current study suggested that the addition of anthocyanins from purple corn pigment had the potential to maintain UFA concentrations in milk during the storage period.

Topics: Animals; Anthocyanins; Fatty Acids; Fatty Acids, Unsaturated; Food Storage; Milk; Pigments, Biological; Zea mays

Topics: Anthocyanins; Color; Flowers; Gene Expression Profiling; Gene Expression Regulation, Plant; Phenotype; Plant Proteins; Ranunculus

The nutritional composition - including total and individual phenolic compounds, carotenoids, and the antioxidant capacity - of two commercially available edible flowers, pansy and snapdragon, was studied. The edible flowers did not differ in their carbohydrates, fat, or ash contents, or in total energy, but pansy had higher values of moisture, protein, and total dietary fiber than snapdragon. Phenolic compounds were more abundant in pansy than in snapdragon, and flavonoids were the major compounds, followed by anthocyanins. The phenolic profile of pansy included flavonols, such as quercetin and isorhamnetin glycosides, flavones, such as apigenin glycosides, and anthocyanins, such as cyanidin and delphinidin glycosides; in snapdragon it included flavonol glycosides (e.g. quercetin and kaempferol glycosides) and anthocyanins, such as cyanidin and pelargonidin glycosides. The contents of total carotenoids were 146 and 29 µg/mg for pansy and snapdragon, respectively, and lutein was the dominant compound.

Topics: Anthocyanins; Antioxidants; Antirrhinum; Carotenoids; Flavonoids; Flavonols; Flowers; Glycosides; Lutein; Phenols; Plant Extracts; Viola

Unauthorized genetically engineered orange petunias were found on the market. Genetic engineering of petunia was shown to lead to novel flower color some 20 years ago. Here we show that petunia lines with orange flowers, generated for scientific purposes, apparently found their way to petunia breeding programmes, intentionally or unintentionally. Today they are widely available, but have not been registered for commerce.

Topics: Alcohol Oxidoreductases; Anthocyanins; Breeding; Flowers; Genetic Engineering; Petunia; Pigmentation; Pigments, Biological; Plant Proteins; Plants, Genetically Modified; Transgenes

Here, we are reporting a sensitive, simple and rapid method for the analysis of cyanidin chloride and pelargonidin chloride anthocyanins in cherry, sour cherry, pomegranate and barberry produced in Iran. The analytes were extracted with acetonitrile-hydrochloric acid (1% v/v) mixture under optimized pretreatment conditions. Clean-up of the extract from fruits was conducted by magnetic solid phase extraction using salicylic acid functionalized silica-coated magnetite nanoparticles (SCMNPs) as the adsorbent. The optimized conditions searched with central composite design. Working under optimum conditions specified as: SCMNPs modified with salicylic acid, sorbent contact time and sample 10min, mechanical stirring time 57.3min. HPLC with UV-detection was used for determination of the analytes. The limit of detection, LOD, obtained for the two anthocyanins were 0.02 and 0.03μgg

Topics: Anthocyanins; Chromatography, High Pressure Liquid; Fruit; Lythraceae; Magnetite Nanoparticles; Prunus avium; Solid Phase Extraction

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

Recently, we developed a novel tea cultivar 'Ziyan' with distinct purple leaves. There was a significant correlation between leaf color and anthocyanin pigment content in the leaves. A distinct allocation of metabolic flow for B-ring trihydroxylated anthocyanins and catechins in 'Ziyan' was observed. Delphinidin, cyanidin, and pelargonidin (88.15 mg/100 g FW in total) but no other anthocyanin pigments were detected in 'Ziyan', and delphinidin (70.76 mg/100 g FW) was particularly predominant. An analysis of the catechin content in 'Ziyan' and eight other cultivars indicated that 'Ziyan' exhibits a preference for synthesizing B-ring trihydroxylated catechins (with a proportion of 74%). The full-length cDNA sequences of flavonoid pathway genes were isolated by RNA-Seq coupled with conventional TA cloning, and their expression patterns were characterized. Purple-leaved cultivars had lower amounts of total catechins, polyphenols, and water extract than ordinary non-anthocyanin cultivars but similar levels of caffeine. Because dark-purple-leaved Camellia species are rare in nature, this study provides new insights into the interplay between the accumulations of anthocyanins and other bioactive components in tea leaves.

Topics: Anthocyanins; Caffeine; Camellia sinensis; Catechin; Flavonoids; Plant Extracts; Plant Leaves; Polyphenols; Tea

Possibility of use of dye extract from skin samples of a seasonal, indigenous fruit from Borneo, namely Canarium odontophyllum, in dye sensitized solar cells (DSSCs) are explored. Three main groups of flavonoid pigments are detected and these pigments exhibit different UV-vis absorption properties, and hence showing different light harvesting capabilities. When applied in DSSCs. The detected pigment constituents of the extract consist of aurone (maritimein), anthocyanidin (pelargonidin) and anthocyanidin (cyanidin derivatives). When tested in DSSC, the highest conversion efficiency of 1.43% is exhibited by cyanidin derivatives, and this is followed by conversion efficiencies of 0.51% and 0.79% for aurone and pelargonidin, respectively. It is shown that individual pigments, like cyanidin derivatives and pelargonidin, exhibit higher power conversion efficiency when compared to that of C.odontophyllum skin pigment mixture (with a conversion efficiency of only 0.68%). The results indicate a possibility of masking effects of the pigments when used as a mixture. The acidification of C.odontophyllum skin pigments with concentrated hydrochloric acid improves the conversion efficiency of the mixture from 0.68% to 0.99%. The discussion in this paper will draw data and observations from the variation in absorption and adsorption properties, the HOMO-LUMO levels, the energy band gaps and the functional group compositions of the detected flavonoids.

Topics: Anthocyanins; Coloring Agents; Electricity; Electrochemical Techniques; Fruit; Sapindaceae; Solar Energy; Spectrophotometry, Ultraviolet; Spectroscopy, Fourier Transform Infrared

Anthocyans (anthocyanins and their aglycones anthocyanidins) are colorful pigments, naturally occurring in fruits. They exhibit many biological effects and have potent health benefits. Anthocyans are widely used as dietary supplements and the safety of products containing them is of great importance. To investigate whether anthocyans influence the expression of hepatic uptake transporters from the organic anion transporting polypeptide (SLCO gene/OATP protein) family, we carried out studies on primary cultures of human hepatocytes. The hepato-cellular accumulation of widely used drugs such as statins and some anticancer drugs is mediated by the liver-specific OATP1B1 and OATP1B3, thus any interference with expression of these particular transporters might influence therapeutic outcomes. We evaluated the effects of 21 anthocyanins and their corresponding 6 anthocyanidins on the expression levels of SLCO1B1/SLCO1B3 by RT-qPCR. Changes in OATP protein levels were confirmed by western blotting. Our data show that OATP1B1 responds differently to anthocyans compared with OATP1B3. We observed the induction of SLCO1B1 gene and OATP1B1 protein in four hepatocyte samples by the anthocyanins malvin chloride, malvidin-3-O-galactoside chloride and cyanidin-3-O-sophoroside chloride. For SLCO1B3, a reduction in the expression levels was seen with delphin chloride and the anthocyanidin pelargonidin. Although the values varied considerably between primary hepatocyte isolates from different individuals, a mean induction of SLCO1B1 (up to 60%) and reduction of SLCO1B3 (by less than 25%) were detected. We propose that the effects of anthocyans derived from high dose dietary supplements may have to be taken into account in patients undergoing a therapy with drugs transported by OATP1B1 and OATP1B3.

Topics: Adult; Anthocyanins; Anticarcinogenic Agents; Cells, Cultured; Dietary Supplements; Fruit; Galactosides; Gene Expression Regulation; Glucosides; Hepatocytes; Humans; Liver-Specific Organic Anion Transporter 1; Male; Middle Aged; Molecular Structure; Organic Anion Transporters; Organic Anion Transporters, Sodium-Independent; Solute Carrier Organic Anion Transporter Family Member 1B3

Pelargonidin (PEL) and cyanidin (CYN) are among the six most abundant anthocyanidins which provide red, blue and purple colors to fruits and vegetables. Health benefits associated with intake of anthocyanins have been attributed mainly to antioxidant activity of these color pigments. The aim of our present study was to assess in mice the impact of PEL and CYN intake on genotoxic stress induced by DNA damaging environmental toxicants. These anthocyanidins were administered by gavage to mice before exposure to genotoxic carcinogens diepoxybutane (DEB) and urethane (URE). In addition, the inhibitory effect of PEL and CYN on endogenous nitrosation was evaluated by using a model nitrosation reaction mixture consisting of methyl urea (MU)+sodium nitrite (SN) which reacts in the stomach to form the carcinogenic methyl nitrosourea (MNU). All the test doses of PEL (2.5-20 mg/kg) and CYN (1-4 mg/kg) significantly reduced the genotoxicity of DEB. A dose-related increase was observed for antigenotoxicity of PEL against URE. The lowest test-dose of CYN showed maximum protection against URE. Co-administration of PEL/CYN with the nitrosation reaction mixture led to reduction in genotoxicity. CYN was more effective as an inhibitor of endogenous nitrosation. Combination of PEL with ascorbic acid (AA) enhanced the antinitrosating effect when compared to that with each phytochemical alone. The results of our present study indicate that common anthocyanidins PEL and CYN can play a major role in reducing genotoxic stress induced by environmental toxicants.

Topics: Animals; Anthocyanins; Antimutagenic Agents; Biphenyl Compounds; Carcinogens; DNA Damage; Epoxy Compounds; Male; Mice; Micronucleus Tests; Mutagens; Nitrosation; Picrates; Urethane

Experiments were performed to assess in mice the inhibitory effects of the anthocyanidins cyanidin, delphinidin, malvidin, and pelargonidin on genotoxic damage induced by the anticancer drugs cyclophosphamide, procarbazine, and cisplatin. Each anthocyanidin was administered 30 min before injecting the drug, and genotoxicity was assessed by measuring micronucleated polychromatic erythrocytes in bone marrow cells. In addition, we monitored the effect of anthocyanidins on apoptosis induced by cyclophosphamide and procarbazine. The results showed significant protective effects of cyanidin, delphinidin, malvidin, and pelargonidin against DNA damage induced by cyclophosphamide. With delphinidin and malvidin, a biphasic dose-response was observed for protection against cyclophosphamide. Dose-related reduction of genotoxicity was observed with pelargonidin against procarbazine. However with cyanidin, the medium dose of 2 mg/kg showed maximum protection against procarbazine. Cyanidin and pelargonidin significantly reduced the chromosomal damage induced by cisplatin. Furthermore, pre-treatment with these anthocyanidins reduced the level of apoptosis induced by cyclophosphamide and procarbazine. In conclusion, this study shows that anthocyanidins can reduce the efficacy of anticancer drugs for inducing DNA damage and apoptosis.

Topics: Animals; Anthocyanins; Antimutagenic Agents; Antineoplastic Agents; Apoptosis; Cisplatin; Cyclophosphamide; DNA Damage; Dose-Response Relationship, Drug; Mice; Micronucleus Tests; Mutagens; Procarbazine

During fruit ripening, strawberries show distinct changes in the flavonoid classes that accumulate, switching from the formation of flavan 3-ols and flavonols in unripe fruits to the accumulation of anthocyanins in the ripe fruits. In the common garden strawberry (Fragaria×ananassa) this is accompanied by a distinct switch in the pattern of hydroxylation demonstrated by the almost exclusive accumulation of pelargonidin based pigments. In Fragaria vesca the proportion of anthocyanins showing one (pelargonidin) and two (cyanidin) hydroxyl groups within the B-ring is almost equal. We isolated two dihydroflavonol 4-reductase (DFR) cDNA clones from strawberry fruits, which show 82% sequence similarity. The encoded enzymes revealed a high variability in substrate specificity. One enzyme variant did not accept DHK (with one hydroxyl group present in the B-ring), whereas the other strongly preferred DHK as a substrate. This appears to be an uncharacterized DFR variant with novel substrate specificity. Both DFRs were expressed in the receptacle and the achenes of both Fragaria species and the DFR2 expression profile showed a pronounced dependence on fruit development, whereas DFR1 expression remained relatively stable. There were, however, significant differences in their relative rates of expression. The DFR1/DFR2 expression ratio was much higher in the Fragaria×ananassa and enzyme preparations from F.×ananassa receptacles showed higher capability to convert DHK than preparations from F. vesca. Anthocyanin concentrations in the F.×ananassa cultivar were more than twofold higher and the cyanidin:pelargonidin ratio was only 0.05 compared to 0.51 in the F. vesca cultivar. The differences in the fruit colour of the two Fragaria species can be explained by the higher expression of DFR1 in F.×ananassa as compared to F. vesca, a higher enzyme efficiency (Kcat/Km values) of DFR1 combined with the loss of F3'H activity late in fruit development of F.×ananassa.

Topics: Alcohol Oxidoreductases; Amino Acid Sequence; Anthocyanins; Clone Cells; DNA, Complementary; Fragaria; Fruit; Gene Expression Profiling; Gene Expression Regulation, Developmental; Gene Expression Regulation, Plant; Isoenzymes; Molecular Sequence Data; Phenotype; Phylogeny; Plant Proteins; Sequence Homology, Amino Acid; Species Specificity; Substrate Specificity

The foliar anthocyanin profiles of two amphibious plants, Nesaea crassicaulis and Lobelia cardinalis were analysed for the first time. N. crassicaulis produced very simple anthocyanins, achieving the highest concentrations when grown submerged. In contrast, L. cardinalis produced leaves with a high content of very complex, acylated anthocyanins, especially when growing emergent. Anthocyanins were separated by high performance liquid chromatography. Nesaea crassicaulis anthocyanins were identified according to their fragment mass spectra and ultra-visible-violet spectral characteristics and 1D and 2D NMR spectra as -3,5-di-O-β-glucosides of delphinidin, cyanidin, petunidin, malvidin and peonidin as well as cyanidine and peonidin-3-O-β-glucoside. In L. cardinalis cyanidin-3-O-[6-O-(4-O-E-p-coumaroyl-O-α-rhamnopyranosyl)-β-glucopyrano]-5-O-β-glucopyranoside was the major anthocyanin and contributed more than 98% of total anthocyanin content. The remaining 2% was made up by cyanidin-3-O-[6-O-(4-O-E-caffeoyl-O-α-rhamnopyranosyl)-β-glucopyrano]-5-O-β-glucopyranoside and pelargonidin-3-O-[6-O-(4-O-E-p-coumaroyl-O-α-rhamnopyranosyl)-β-glucopyrano]-5-O-β-glucopyranoside.

Topics: Anthocyanins; Flavonoids; Glucosides; Lobelia; Lythraceae; Magnetic Resonance Spectroscopy; Plant Leaves

The anthocyanins of 21 hybrid red varieties produced by crossing V. vinifera, V. riparia, V. labrusca, V. lincecumii and V. rupestris species, the profiles for which have not yet been reported, were studied. Profiles were determined by LC/DAD, and identification of single anthocyanins was confirmed by LC/MS precursor-ion analysis. Anthocyanidin precursors (pelargonidin at m/z 271, dephinidin at m/z 303, cyanidin at m/z 287, petunidin at m/z 317, peonidin at m/z 301, and malvidin at m/z 331) and precursors of monoglucoside compounds allowed 24 different compounds to be identified. Analysis of precursor ions of monoglucoside anthocyanins at low capillary voltage revealed the signals of diglucosides only, providing a very selective method for analysis of diglucoside anthocyanins in grape. According to anthocyanin profile, the samples were subdivided into two groups: one characterized by the substantial presence of diglucoside compounds (particularly Seyve Villard 23-399 and Seyve Villard 23-369) and one by the scarce presence or practical absence of diglucosides (Seibel 10878, Burdin 4077, and Galibert 238-35). Particularly interesting for producing anthocyanin for the natural colorant industry were the varieties Siebel 8357, Bacò 30-12 and Terzi 100-31.

Topics: Anthocyanins; Chromatography, High Pressure Liquid; Spectrometry, Mass, Electrospray Ionization; Vitis

Current research indicates that anthocyanins are primarily degraded to form phenolic acid products. However, no studies have yet demonstrated the metabolic conjugation of these anthocyanin-derived phenolic acids in humans.. Within the present study, a simulated gastrointestinal digestion model was used to evaluate the potential degradation of anthocyanins post-consumption. Subsequently, cyanidin (Cy) and pelargonidin and their degradation products, protocatechuic acid and 4-hydroxybenzoic acid, were incubated in the presence of human liver microsomes to assess their potential to form hepatic glucuronide conjugates. For structural conformation, phenolic glucuronides were chemically synthesised and compared to the microsomal metabolites. During the simulated gastric digestion, anthocyanin glycosides (200 μM) remained stable however their aglycone derivatives were significantly degraded (20% loss), while during subsequent pancreatic/intestinal digestion only pelargonidin-3-glucoside remained stable while cyanidin-3-glucoside (30% loss) and Cy and pelagonidin aglycones were significantly degraded (100% loss, respectively). Following microsomal metabolism, pelargonidin formed 4-hydroxybenzoic acid, which was further metabolised (65%) to form two additional glucuronide conjugates, while Cy formed protocatechuic acid, which was further metabolised (43%) to form three glucuronide conjugates.. We propose that following ingestion, anthocyanins may be found in the systemic circulation as free or conjugated phenolic acids, which should be a focus of future dietary interventions.

Topics: Analysis of Variance; Anthocyanins; Chromatography, High Pressure Liquid; Digestion; Glucosides; Glucuronides; Humans; Hydroxybenzoates; Intestinal Mucosa; Male; Microsomes, Liver; Parabens

Colorectal cancer is the second most frequent cause of cancer death in the western world. Although the prognosis has improved after the introduction of newer anticancer drugs, the treatment of metastatic colorectal cancer still remains a challenge due to a high percentage of drug-resistant tumor forms. We aimed at testing whether anthocyanidins exerted cytotoxicity in primary (Caco-2) and metastatic (LoVo and LoVo/ADR) colorectal cancer cell lines. Both cyanidin and delphinidin, though neither pelargonidin nor malvidin, were cytotoxic in metastatic cells only. The cell line most sensitive to anthocyanidins was the drug-resistant LoVo/ADR. There, cellular ROS accumulation, inhibition of glutathione reductase, and depletion of glutathione could be observed. This suggests that anthocyanidins may be used as sensitizing agents in metastatic colorectal cancer therapy.

Topics: Anthocyanins; Antioxidants; Apoptosis; Caco-2 Cells; Camptothecin; Cell Line, Tumor; Colonic Neoplasms; Drug Resistance, Neoplasm; Glutathione; Glutathione Reductase; Humans; Oxidants; Oxidative Stress

Modern biotechnology has developed powerful tools for genetic engineering and flower colours are an excellent object to study possibilities and limitations of engineering strategies. Osteospermum hybrida became a popular ornamental plant within the last 20 years. Many cultivars display rose to lilac flower colours mainly based on delphinidin-derived anthocyanins. The predominant synthesis of delphinidin derivatives is referred to a strong endogenous flavonoid 3',5'-hydroxylase (F3'5'H) activity. Furthermore, since dihydroflavonol 4-reductase (DFR) of Osteospermum does not convert dihydrokaempferol (DHK) to leucopelargonidin, synthesis of pelargonidin-based anthocyanins is naturally not realised. In order to redirect anthocyanin biosynthesis in Osteospermum towards pelargonidin derivatives, we introduced cDNAs coding for DFRs which efficiently convert DHK to LPg. But neither the expression of Gerbera hybrida DFR nor of Fragaria x ananassa DFR - the latter is characterised by an unusual high substrate preference for DHK - altered anthocyanin composition in flowers of transgenic plants. However, chemical inhibition of F3'5'H activity in ray florets of dfr transgenic plants resulted in the accumulation of pelargonidin derivatives. Accordingly, retransformation of a transgenic plant expressing Gerbera DFR with a construct for RNAi-mediated suppression of F3'5'H activity resulted in double transgenic plants accumulating predominantly pelargonidin derivatives in flowers.

Topics: Alcohol Oxidoreductases; Anthocyanins; Asteraceae; Chalcones; DNA, Complementary; Flavones; Flavonoids; Flavonols; Flowers; Genetic Vectors; Isoenzymes; Plants, Genetically Modified

Anthocyanins are a group of natural occurring pigments responsible for the red-blue color of grapes and many fruits and vegetables. Anthocyanins and derived pigments are of double interest, one technological, as they can be used as natural colorants, and another one due to their implication on human health through their antioxidant activity. Although there are numerous studies regarding the antioxidant activity of grape extracts as well as red wine, the free radical scavenging activity of purified anthocyanins and pyranoanthocyanins is largely unknown. In the present study, the hydroxyl and superoxide anion scavenging activities of anthocyanins and their pyruvic acid adducts were systematically investigated by electron spin resonance spectroscopy and spin trapping. The 3-glucosides of delphinidin, cyanidin, petunidin, pelargonidin and malvidin, and the pyruvic adduct of the 3-glucoside of delphinidin exhibited a potent superoxide anion radical scavenging and, to a lesser extent hydroxyl anion radical scavenging activity. The pyranoanthocyanins of cyanidin, petunidin, malvidin and pelargonidin showed a high capacity to scavenge superoxide anion radicals but did not scavenge hydroxyl radicals. Current data indicate that formation of anthocyanin adducts with pyruvic acid, which may occur during wine ageing or fruit juice processing, decreases the hydroxyl and superoxide anion scavenging and thus could decrease the antioxidant potential of these compounds.

Topics: Anthocyanins; Electron Spin Resonance Spectroscopy; Free Radical Scavengers; Hydroxyl Radical; Pyruvic Acid; Superoxides; Wine

Weaning pigs (7.9 +/- 1.7 kg) were fed a freeze-dried powder of marionberry (MB) by stomach tube to study the absorption and metabolism of anthocyanins. Four major anthocyanins (ACNs) were found in MB: cyanidin-3-glucoside (Cy-3-glc, 78%), cyanidin-3-rutinoside (Cy-3-rutin, 20%), pelargonidin-3-glucoside (Pg-3-glc, 0.4%), and 1 unknown acylated cyanidin-based ACN (UACy, 1.5%). In the urine, the 4 original ACNs and 11 metabolites were identified and quantified. The main metabolites were glucuronidated and/or methylated forms of the original anthocyanins. Total recovery of the 4 original ACNs plus their related metabolites was 0.087 +/- 0.034% for Cy-3-glc, 0.084 +/- 0.026% for Cy-3-rutin, 0.583 +/- 0.229% for Pg-3-glc and 0.036 +/- 0.011% for UACy (mean +/- SD, n = 3), respectively. For the individual ACNs, the amount of metabolites recovered from Cy-3-rutin was lower than that of the original intact Cy-3-rutin, whereas the amounts of metabolites from Cy-3-glc and Pg-3-glc in the urine were much higher than their original forms. In pig plasma, the 2 original ACNs, Cy-3-glc and Cy-3-rutin, and a trace of 1 metabolite (cyanidin monoglucuronide) were detected. The plasma concentration:dose ratio of Cy-3-rutin was higher than that of Cy-3-glc. Different aglycones and/or sugar moieties may influence the absorption and metabolism of ACNs. Cy-3-glc and Cy-3-rutin had similar apparent excretion rates relative to dose, whereas Pg-3-glc had a much higher total urinary excretion than cyanidin-based anthocyanins. Most of Cy-3-glc and Pg-3-glc were excreted in the form of metabolites, whereas most of the Cy-3-rutin was excreted in its original unmetabolized form. Urinary recovery of the acylated anthocyanin was lower than that of nonacylated anthocyanins.

Topics: Animals; Anthocyanins; Area Under Curve; Chromatography, High Pressure Liquid; Intestinal Absorption; Plant Extracts; Structure-Activity Relationship; Swine

The antioxidant activity of the six common anthocyanidins, pelargonidin, cyanidin, delphinidin, peonidin, petunidin, and malvidin, and their glycosidic forms was evaluated in three lipid-containing models [human low-density lipoprotein (LDL) and bulk and emulsified methyl linoleate]. In addition, the radical scavenging activity of the compounds against the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical was studied. Most anthocyanins and their aglycons acted as strong antioxidants in emulsion and LDL. Many compounds showed an activity comparable to the well-known antioxidants alpha-tocopherol, Trolox, catechin, and quercetin. In bulk methyl linoleate, anthocyanins and anthocyanidins possessed only a weak antioxidant activity or even oxidation-promoting activity. Depending on the anthocyanidin, different glycosylation patterns either enhanced or diminished the antioxidant power. For the most part, the activities of the glycosides and the aglycons did not differ remarkably in emulsion. In LDL the aglycons showed in general higher activities than the glycosides. In bulk oil, to the contrary, the glycosides were more effective than the aglycons.

Topics: Anthocyanins; Antioxidants; Biphenyl Compounds; Emulsions; Free Radical Scavengers; Glucosides; Glycosides; Humans; Linoleic Acids; Lipid Peroxidation; Lipoproteins, LDL; Phenols; Picrates

The protective effect of anthocyanidins against the toxicity induced by linoleic acid hydroperoxide (LOOH) was examined in cultured human fetal lung fibroblasts, TIG-7. Cyanidin was more effective than pelargonidin or delphinidin in inhibiting LOOH-induced cytotoxicity. The presence of a catechol moiety in the B ring is shown to be important for the protective activities against the cytotoxicity of LOOH.

Topics: Anthocyanins; Antioxidants; Cell Line; Cell Survival; Fibroblasts; Humans; Linoleic Acids; Lipid Peroxides; Reactive Oxygen Species