Cyanidin
From Wikipedia, the free encyclopedia
| Cyanidin | |
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| IUPAC name | 2-(3,4-Dihydroxyphenyl) chromenylium-3,5,7-triol |
| Other names | Cyanidine |
| Identifiers | |
| CAS number | 13306-05-3 528-58-5 (chloride) |
| PubChem | |
| SMILES | C1=CC(=C(C=C1C2= C(C=C3C(=CC(=CC3= [O+]2)O)O)O)O)O |
| Properties | |
| Molecular formula | C15H11O6+ |
| Molar mass | 287.24 g/mol |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Cyanidin is a natural organic compound. It is a particular type of anthocyanidin (not to be confused with anthocyanins which are glycosides of anthocyanidins). It is a pigment found in many redberries including but not limited to grapes, bilberry, blackberry, blueberry, cherry, cranberry, elderberry, hawthorn, loganberry, acai berry and raspberry.[1] It can also be found in other fruits such as apples and plums. It is also found in red cabbage. It has a characteristic reddish-orange color, though this can change with pH, red ph < 3, violet at pH 7-8, blue at pH > 11. The highest concentrations of cyanidin are found in the skin of the fruit. Recently, the biosynthesis of cyanidin 3-O-glucoside in Escherichia coli was demonstrated.[2]
[edit] Effects on the human body
Cyanidin, like other anthocyanidins, has putative antioxidant and radical-scavenging effects which may protect cells from oxidative damage and reduce risk of cardiovascular diseases and cancer. One theory is that dietary intake of cyanidins may inhibit development of obesity and diabetes as well as contain inflammatory mechanisms.[3]
Other studies have generally shown that the glucoside derivative of cyanidin may have a role in cancer therapy.[4][5][6]
[edit] List of cyanidin derivates
- cyanidin-3-rutinoside (3-C-R)
- cyanidin 3-O, found in red onion
- cyanidin 7-O, found in red onion
- cyanidin 3,4′-di-O-β-glucopyranoside, found in red onion
- cyanidin 4′-O-β-glucoside, found in red onion
[edit] References
- ^ *Cyanidin at phytochemicals.info
- ^ Yan Y, Chemler J, Huang L, Martens S, Koffas MA (2005). "Metabolic engineering of anthocyanin biosynthesis in Escherichia coli". Appl. Environ. Microbiol. 71 (7): 3617–23. doi:. PMID 16000769.
- ^ Sasaki R, Nishimura N, Hoshino H, Isa Y, Kadowaki M, Ichi T, Tanaka A, Nishiumi S, Fukuda I, Ashida H, Horio F, Tsuda T. Cyanidin 3-glucoside ameliorates hyperglycemia and insulin sensitivity due to downregulation of retinol binding protein 4 expression in diabetic mice. Biochem Pharmacol. 2007 Dec 3;74(11):1619-27.[1]
- ^ Fimognari C, Berti F, Nusse M, Cantelli Forti G, Hrelia P (2005). "In vitro antitumor activity of cyanidin-3-O-beta-glucopyranoside". Chemotherapy 51 (6): 332–5. doi:. PMID 16224184.
- ^ Chen PN, Chu SC, Chiou HL, Kuo WH, Chiang CL, Hsieh YS (2006). "Mulberry anthocyanins, cyanidin 3-rutinoside and cyanidin 3-glucoside, exhibited an inhibitory effect on the migration and invasion of a human lung cancer cell line". Cancer Lett. 235 (2): 248–59. doi:. PMID 15975709.
- ^ Tulio AZ Jr, Reese RN, Wyzgoski FJ, Rinaldi PL, Fu R, Scheerens JC, Miller AR. Cyanidin 3-rutinoside and cyanidin 3-xylosylrutinoside as primary phenolic antioxidants in black raspberry. J Agric Food Chem. 2008 Mar 26;56(6):1880-8.[2]
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