Cyanidin-3-O-glucoside chlorideCAS# 7084-24-4 |
- Cyanidin-3-O-galactoside chloride
Catalog No.:BCN3022
CAS No.:27661-36-5
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 7084-24-4 | SDF | Download SDF |
| PubChem ID | 197081 | Appearance | Dark, reddish powder |
| Formula | C21H21O11 | M.Wt | 449.38 |
| Type of Compound | Flavonoids | Storage | Desiccate at -20°C |
| Synonyms | Chrysontemin; Cyanidin 3-O-glucoside chloride | ||
| Solubility | DMSO : 30 mg/mL (61.88 mM; Need ultrasonic and warming) | ||
| Chemical Name | (2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;chloride | ||
| SMILES | C1=CC(=C(C=C1C2=C(C=C3C(=CC(=CC3=[O+]2)O)O)OC4C(C(C(C(O4)CO)O)O)O)O)O.[Cl-] | ||
| Standard InChIKey | YTMNONATNXDQJF-UBNZBFALSA-N | ||
| Standard InChI | InChI=1S/C21H20O11.ClH/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-6-10-12(25)4-9(23)5-14(10)30-20(15)8-1-2-11(24)13(26)3-8;/h1-6,16-19,21-22,27-29H,7H2,(H3-,23,24,25,26);1H/t16-,17-,18+,19-,21-;/m1./s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Cyanidin-3- O -glucoside exhibits strong antioxidant activities, it has protective effects from blackberry extract against peroxynitrite-induced endothelial dysfunction and vascular failure. Cyanidin-3-O-glucoside chloride decreased mutant p21 expression, and increased the ratio of Bax/Bcl-2 and the activation of caspase-3 to induce apoptosis. |
| Targets | Bcl-2/Bax | Caspase | p21 |
| In vitro | Protective effects of cyanidin-3-O-glucoside from blackberry extract against peroxynitrite-induced endothelial dysfunction and vascular failure.[Pubmed: 12818719]Life Sci. 2003 Jul 18;73(9):1097-114.Anthocyanins are a group of naturally occurring phenolic compounds as colorants in several plants, flowers and fruits. These pigments have a great importance as quality indicators, as chemotaxonomic markers and antioxidants.
Cytotoxicity and Apoptotic Effects of Polyphenols from Sugar Beet Molasses on Colon Carcinoma Cells in Vitro[Pubmed: 27347927]Int J Mol Sci. 2016 Jul; 17(7): 993.Three polyphenols were isolated and purified from sugar beet molasses by ultrasonic-aid extraction and various chromatographic techniques, and their structures were elucidated by spectral analysis. Cytotoxicity and the molecular mechanism were measured by methyl thiazolyl tetrazolium (MTT) assay, flow cytometry, caspase-3 activity assay and Western blot assay. The results showed that gallic acid, Cyanidin-3-O-glucoside chloride and epicatechin have cytotoxicity to the human colon, hepatocellular and breast cancer cells. Cyanidin-3-O-glucoside chloride showed its cytotoxicity against various tumor cell lines, particularly against colon cancer Caco-2 cells with half maximal inhibitory concentration (IC50) value of 23.21 ± 0.14 μg/mL in vitro. Cyanidin-3-O-glucoside chloride may be a potential candidate for the treatment of colon cancer. In the mechanism study, Cyanidin-3-O-glucoside chloride increased the ratio of cell cycle at G0/G1 phase and reduced cyclin D1 expression on Caco-2 cells. Cyanidin-3-O-glucoside chloride decreased mutant p21 expression, and increased the ratio of Bax/Bcl-2 and the activation of caspase-3 to induce apoptosis. |
| Cell Research | Antioxidant and in vitro anticancer activities of phenolics isolated from sugar beet molasses[Pubmed: 26347338 ]BMC Complement Altern Med. 2015; 15: 313.In the present study, the phenolic compounds were prepared using ultrasonic-aid extraction from sugar beet molasses (SBM).
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Cyanidin-3-O-glucoside chloride Dilution Calculator
Cyanidin-3-O-glucoside chloride Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.2253 mL | 11.1264 mL | 22.2529 mL | 44.5058 mL | 55.6322 mL |
| 5 mM | 0.4451 mL | 2.2253 mL | 4.4506 mL | 8.9012 mL | 11.1264 mL |
| 10 mM | 0.2225 mL | 1.1126 mL | 2.2253 mL | 4.4506 mL | 5.5632 mL |
| 50 mM | 0.0445 mL | 0.2225 mL | 0.4451 mL | 0.8901 mL | 1.1126 mL |
| 100 mM | 0.0223 mL | 0.1113 mL | 0.2225 mL | 0.4451 mL | 0.5563 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Kuromanin (chloride), extracted from mulberry leaves, has been shown to improve blood glucose concentrations and lipid homeostasis and to reduce obesity.
References:
[1]. Ha -Na Na, et al. Reduction of adenovirus 36-induced obesity andin?ammation by mulberry extract. Microbiol Immunol 2014; 58: 303–306
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Antioxidant and in vitro anticancer activities of phenolics isolated from sugar beet molasses.[Pubmed:26347338]
BMC Complement Altern Med. 2015 Sep 7;15:313.
BACKGROUND: In the present study, the phenolic compounds were prepared using ultrasonic-aid extraction from sugar beet molasses (SBM). METHODS: Gallic acid (GA), Cyanidin-3-O-glucoside chloride (CGC) and epicatechin (EP) were produced after column chromatography from the extraction, and further detected using NMR, QTOF-MS and ESI-MS/MS. RESULTS: The three compounds exhibited strong antioxidant activities including DPPH radical scavenging activities, ABTS radical scavenging activities and ORAC values. GA showed the strongest antioxidant activity. Antitumor activities significantly increased in a dose-dependent manner. In particular, the CGC had growth inhibitory activities of 94.86, 87.27 and 67.13% against the human colon (CACO-2), hepatocellular (HepG2) and breast (MCF-7) carcinoma cell lines, respectively, at the highest concentration of 400 mug/mL of the extracts. These results suggest that the three compounds are key chemical compositions valuable for preparing functional foods in the food industry. CONCLUSIONS: The results suggested that SBM is a natural source of antioxidant and antitumor agents for preparing functional foods.
Protective effects of cyanidin-3-O-glucoside from blackberry extract against peroxynitrite-induced endothelial dysfunction and vascular failure.[Pubmed:12818719]
Life Sci. 2003 Jul 18;73(9):1097-114.
Anthocyanins are a group of naturally occurring phenolic compounds as colorants in several plants, flowers and fruits. These pigments have a great importance as quality indicators, as chemotaxonomic markers and antioxidants. The content of blackberry (Rubus species) juice was investigated by HPLC/ESI/MS using narrow bore HPLC columns. Using this method we demonstrated that cyanidin-3-O-glucoside represents about 80% of the total anthocyanin contents in blackberry extract. Here we investigated antioxidant activity of the blackberry juice and cyanidin-3-O-glucoside on the endothelial dysfunction in cells and in vascular rings exposed to peroxynitrite. In human umbilical vein endothelial cells (HUVEC) in vitro, peroxynitrite caused a significant suppression of mitochondrial respiration (38 +/- 2.1% of control cells), as measured by the mitochondrial-dependent conversion of the dye MTT to formazan. Peroxynitrite caused DNA strand breakage (63 +/- 1.9% single strand vs 3 +/- 0.9% single strand in control cells), as measured by the alkaline unwinding assay, and caused an activation of PARS, as measured by the incorporation of radiolabeled NAD(+) to nuclear proteins. Blackberry juice (different dilutions that contained 80 ppm;40 ppm;14.5 ppm of cyanidin-3-O-glucoside) and cyanidin-3-O-glucoside (as chloride) (0.085 microM; 0.028 microM; 0.0085 microM) reduced the peroxynitrite-induced suppression of mitochondrial respiration, DNA damage and PARS activation in HUVECs. Vascular rings exposed to peroxynitrite exhibited reduced endothelium-dependent relaxant responses in response to acetylcholine as well as a vascular contractility dysfunction in response to norepinephrine. The development of this peroxynitrite-induced vascular dysfunction was ameliorated by the blackberry juice (different dilutions that contained 80 ppm;40 ppm;14.5 ppm of cyanidin-3-O-glucoside) and cyanidin-3-O-glucoside (as chloride) (0.085 microM;0.028 microM;0.0085 microM). In conclusion our findings clearly demonstrate that blackberry juice containing cyanidin-3-O-glucoside is a scavenger of peroxynitrite and that exert a protective effect against endothelial dysfunction and vascular failure induced by peroxynitrite.
Cytotoxicity and Apoptotic Effects of Polyphenols from Sugar Beet Molasses on Colon Carcinoma Cells in Vitro.[Pubmed:27347927]
Int J Mol Sci. 2016 Jun 23;17(7). pii: ijms17070993.
Three polyphenols were isolated and purified from sugar beet molasses by ultrasonic-aid extraction and various chromatographic techniques, and their structures were elucidated by spectral analysis. Cytotoxicity and the molecular mechanism were measured by methyl thiazolyl tetrazolium (MTT) assay, flow cytometry, caspase-3 activity assay and Western blot assay. The results showed that gallic acid, Cyanidin-3-O-glucoside chloride and epicatechin have cytotoxicity to the human colon, hepatocellular and breast cancer cells. Cyanidin-3-O-glucoside chloride showed its cytotoxicity against various tumor cell lines, particularly against colon cancer Caco-2 cells with half maximal inhibitory concentration (IC50) value of 23.21 +/- 0.14 mug/mL in vitro. Cyanidin-3-O-glucoside chloride may be a potential candidate for the treatment of colon cancer. In the mechanism study, Cyanidin-3-O-glucoside chloride increased the ratio of cell cycle at G(0)/G(1) phase and reduced cyclin D1 expression on Caco-2 cells. Cyanidin-3-O-glucoside chloride decreased mutant p21 expression, and increased the ratio of Bax/Bcl-2 and the activation of caspase-3 to induce apoptosis.
