pelargonidin and malvidin

Topics: Anthocyanins; Phenols

Hypothesis Anthocyanins possess well-known biological effects and suppress DNA damage induced by therapeutic topoisomerase poisons. Our study focusses on the modulatory effects of anthocyanidins-malvidin (MAL) and pelargonidin (PEL)-on topoisomerase II poison mitoxantrone (MXT)-induced cytotoxicity and genotoxicity in in vitro and in vivo conditions. Study design HepG2 cells were treated with MXT (1-10 µM), MAL (10-100 µM,) and PEL (5-640 µM) to determine cell viability. Further, experiments on cytotoxicity and apoptosis induction by single agents or combinations were performed. In vitro and in vivo antigenotoxic effect of MAL/PEL against MXT was evaluated in human lymphocytes and mouse bone marrow cells. Methods Cytotoxicity of test agents and apoptosis induction in HepG2 cells was assessed by MTT assay, trypan blue dye exclusion assay and Hoechst 33258 staining. Antigenotoxic effects of MAL/PEL against MXT were assessed in co-treated human lymphocytes and bone marrow from mice that received MXT intraperitoneally 30 minutes post MAL/PEL oral administration Results Dose-dependent cytotoxicity was observed with all 3 test agents in HepG2 cells. Highest test concentration of 100 µM MAL, 640 µM PEL, and 10 µM MXT decreased HepG2 cell viability by 80%, 30%, and 90%, respectively. The combination of 1 µM MXT + 80 µM MAL reduced cell viability better than single agents. MAL/PEL treatment significantly reduced MXT-induced genotoxicity in human lymphocytes and micronuclei formation in mice. Conclusion Combination of MAL/PEL with lower doses of MXT, especially MAL+MXT increases the cytotoxicity in cancer cells. In addition, MXT treatment with MAL/PEL reduced MXT-induced genotoxicity and protected normal cells during chemotherapy.

Topics: Animals; Anthocyanins; Apoptosis; Cell Line, Tumor; Cell Survival; Cells, Cultured; DNA Damage; Hep G2 Cells; Humans; Lymphocytes; Male; Mice; Mitoxantrone

The present study investigated the neuroprotective effect of anthocyanidins, including cyanidin, delphinidin, malvidin, pelargonidin, and peonidin, against hypoxia in C6 glial cells. The cells were first incubated with a medium containing anthocynidin in normoxia condition and then with a medium containing sodium dithionite (Na2S2O4) in an anaerobic incubator for the hypoxia treatment. Methylthiazole tetrazolium test and evaluation of antioxidant enzyme activities and glutathione concentration were performed on the treated cells. At least 74% of the C6 cells preincubated with 25 mg/L of any of the five anthocyanidins in serum-free Dulbecco's modified Eagle's medium at 37 °C for 24 h survived the hypoxia treatment as compared with a survival rate between 47 and 59% for the control that was preincubated without an anthocyanidin. The cells preincubated with any of the five anthocyanidins showed higher catalase activity and glutathione concentration after the hypoxia treatment as compared with the corresponding samples without the preincubation with anthocyanidin. The cells preincubated with malvidin, pelargonidin, or peonidin also showed higher superoxide dismutase activities. The results of this study justify further research for the development of anthocyanidins into neuroprotective food ingredients against hypoxia injury.

Topics: Animals; Anthocyanins; Antioxidants; Cell Hypoxia; Cell Line; Dithionite; Glutathione; Neuroglia; Rats; Superoxide Dismutase

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

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

Antioxidant extracts from 5 potato lines were evaluated for antioxidant activity, total phenolics, chlorogenic acid, anthocyanin content, and in vitro anticancer capacity. Analysis showed that Mexican wild species S. pinnatisectum had the highest antioxidant activity, total phenolic, and chlorogenic acid content. The proliferation of colon cancer and liver cancer cells was significantly inhibited by potato antioxidant extracts. The highest antiproliferative activity was observed in extracts of S. pinnatisectum and the lowest in Northstar. An inverse correlation was found between total phenolics and the EC(50) of colon cancer cell (R(2) = 0.9303), as well as liver cancer cell proliferation (R(2) = 0.8992). The relationship between antioxidant activity and EC(50) of colon cancer/liver cancer cell proliferation was significant (R(2) = 0.8144; R(2) = 0.956, respectively). A significant difference in inhibition of cancer cells (P < 0.01) existed between the 3 polyphenols: chlorogenic acid, pelargonidin chloride, and malvidin chloride, suggesting that chlorogenic acid was a critical factor in the antiproliferation of colon cancer and liver cancer cells.

Topics: Anthocyanins; Anticarcinogenic Agents; Antioxidants; Caco-2 Cells; Cell Proliferation; Chlorogenic Acid; Hep G2 Cells; Humans; Liver Neoplasms; Lung Neoplasms; Plant Extracts; Polyphenols; Solanum tuberosum

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

Garnacha Tintorera (also known as Alicante Bouschet) is one of the few V. vinifera grape cultivars with red-colored berry flesh. The study of the phenolic composition of both berry flesh and skin of Garnacha Tintorera grapes shows interesting findings. Anthocyanins were asymmetrically distributed within grape flesh and skins. Malvidin derivatives dominated in skin, followed by peonidin-type anthocyanins; in contrast, the flesh almost exclusively contained peonidin 3-glucoside. In addition, LC-UV-vis and LC-MS evidence suggest the presence of small amounts of peonidin 3,5-diglucoside and a second peonidin dihexoside derivative, and, very likely, the first report of the occurrence of pelargonidin 3-glucoside and its acetyl and p-coumaroyl derivatives in V. vinifera grapes. Flavonols also occurred in the flesh of Garnacha Tintorera grapes, but its flavonol profile showed lower contribution of trisubstituted flavonoid structures (myricetin, laricitrin, and syringetin) when compared to that of skin. The skin of Garnacha Tintorera grapes contained hydroxycinnamic acids in higher amounts than in flesh, caftaric acid being the main derivative found, and coutaric acid accounting for its highest proportion in the skin. The phenolic composition of the whole grape berries reflected the average of the differences described for the two aforementioned berry parts, and subsequently, the red wines made from these grapes had a phenolic composition closer to that shown by the whole berries. The formation of anthocyanin-derived pigments in Garnacha Tintorera red wines makes necessary the use of LC-MS for detecting the minor pelargonidin-based anthocyanins and peonidin dihexoside, which could be suggested as chemical markers for cultivar authentication of this grape cultivar and its wines.

Topics: Anthocyanins; Color; Fruit; Glucosides; Phenols; Pigments, Biological; Vitis; Wine

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

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