Cyanidin
 | |
| Names | |
|---|---|
| IUPAC name
2-(3,4-Dihydroxyphenyl) chromenylium-3,5,7-triol | |
| Other names
Cyanidine | |
| Identifiers | |
13306-05-3  (chloride) 528-58-5 (chloride) (chloride)  | |
| 3D model (Jmol) | Interactive image Interactive image |
| ChEBI | CHEBI:27843 |
| ChEMBL | ChEMBL404515 |
| ChemSpider | 114193 |
| KEGG | C05905 |
| PubChem | 128861 |
| |
| |
| Properties | |
| C15H11O6+ | |
| Molar mass | 287.24 g/mol |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| Infobox references | |
Cyanidin is a natural organic compound. It is a particular type of anthocyanidin (glycoside version called anthocyanins). It is a pigment found in many red berries including grapes, bilberry, blackberry, blueberry, cherry, cranberry, elderberry, hawthorn, loganberry, açai berry and raspberry.[1] It can also be found in other fruits such as apples and plums, and in red cabbage and red onion. It has a characteristic reddish-purple color, though this can change with pH; solutions of the compound are red at pH < 3, violet at pH 7-8, and blue at pH > 11. In certain fruits, the highest concentrations of cyanidin are found in the seeds and skin.
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. Other studies have indicated that dietary intake of cyanidins may inhibit development of obesity[2] by inhibiting the effects of unhealthy diets.[3][4] Other studies have indicated that cyanidin intake may inhibit development of diabetes as well as provide anti-inflammatory effects.[2][5]
Other preliminary studies indicate that the glucoside derivative of cyanidin might have a role in cancer therapy, although this remains unproven beyond laboratory testing.[6][7][8]
List of cyanidin derivatives
- Antirrhinin (cyanidin-3-rutinoside or 3-C-R), found in black raspberry[8]
- Cyanidin-3-xylosylrutinoside, found in black raspberry[8]
- Cyanidin-3,4′-di-O-β-glucopyranoside, found in red onion
- Cyanidin-4′-O-β-glucoside, found in red onion
- Chrysontemin (cyanidin-3-O-glucoside), found in blackcurrant pomace
- Ideain (cyanidin 3-O-galactoside), found in Vaccinium species
- Cyanin (cyanidin-3,5-O-diglucoside), found in red wine[9]
References
- ↑ http://www.phytochemicals.info/phytochemicals/cyanidin.php[]
- 1 2 Sasaki, R; Nishimura, N; Hoshino, H; Isa, Y; Kadowaki, M; Ichi, T; Tanaka, A; Nishiumi, S; et al. (2007). "Cyanidin 3-glucoside ameliorates hyperglycemia and insulin sensitivity due to downregulation of retinol binding protein 4 expression in diabetic mice". Biochemical Pharmacology. 74 (11): 1619–27. doi:10.1016/j.bcp.2007.08.008. PMID 17869225.
- ↑ Johnson, Kelly. "Health Benefits of Cyanidin". 10 April 2015. Retrieved 13 August 2015.
- ↑ Tsuda, T; Ueno, Y; Aoki, H; Koda, T; Horio, F; Takahashi, N; Kawada, T; Osawa, T (2004). "Anthocyanin enhances adipocytokine secretion and adipocyte-specific gene expression in isolated rat adipocytes". Biochemical and Biophysical Research Communications. 316 (1): 149–57. doi:10.1016/j.bbrc.2004.02.031. PMID 15003523.
- ↑ He, YH; Xiao, C; Wang, YS; Zhao, LH; Zhao, HY; Tong, Y; Zhou, J; Jia, HW; Lu, C; Li, XM; Lu, AP (2005). "Antioxidant and anti-inflammatory effects of cyanidin from cherries on rat adjuvant-induced arthritis". Zhongguo Zhong Yao Za Zhi. 30 (20): 1602–5. PMID 16422543.
- ↑ Fimognari, Carmela; Berti, Fausto; Nüsse, Michael; Cantelli Forti, Giorgio; Hrelia, Patrizia (2005). "In vitro Antitumor Activity of Cyanidin-3-O-β-Glucopyranoside". Chemotherapy. 51 (6): 332–5. doi:10.1159/000088956. PMID 16224184.
- ↑ Chen, Pei-Ni; Chu, Shu-Chen; Chiou, Hui-Ling; Kuo, Wu-Hsien; Chiang, Chui-Liang; Hsieh, Yih-Shou (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 Letters. 235 (2): 248–59. doi:10.1016/j.canlet.2005.04.033. PMID 15975709.
- 1 2 3 Tulio AZ, Reese RN, Wyzgoski FJ, Rinaldi PL, Fu R, Scheerens JC, Miller AR (2008). "Cyanidin 3-rutinoside and cyanidin 3-xylosylrutinoside as primary phenolic antioxidants in black raspberry". Journal of Agricultural and Food Chemistry. 56 (6): 1880–8. doi:10.1021/jf072313k. PMID 18290621. Retrieved 2015-12-26.
Five anthocyanins were present in black raspberries: cyanidin 3-sambubioside, cyanidin 3-glucoside, cyanidin 3-xylosylrutinoside, cyanidin 3-rutinoside, and pelargonidin 3-rutinoside. Their identities and structures, with particular emphasis on cyanidin 3-xylosylrutinoside, were confirmed by NMR spectroscopy. Two of these anthocyanins, cyanidin 3-rutinoside and cyanidin 3-xylosylrutinoside, predominated, comprising 24-40 and 49-58%, respectively, of the total anthocyanins in black raspberries. On the basis of both potency and concentration, cyanidin 3-rutinoside and cyanidin 3-xylosylrutinoside were found to be the significant contributors to the antioxidant systems of black raspberries.
- ↑ He F, Liang NN, Mu L, Pan QH, Wang J, Reeves MJ, Duan CQ (2012). "Anthocyanins and their variation in red wines I. Monomeric anthocyanins and their color expression". Molecules (Basel, Switzerland). 17 (2): 1571–601. doi:10.3390/molecules17021571. PMID 22314380. Retrieved 2015-12-26.