Cyanidin

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Cyanidin
Cyanidin.svg
Names
IUPAC name
2-(3,4-Dihydroxyphenyl) chromenylium-3,5,7-triol
Other names
Cyanidine
Identifiers
13306-05-3 YesY
(chloride) 528-58-5 (chloride) (chloride) N
ChEBI CHEBI:27843 YesY
ChEMBL ChEMBL404515 YesY
ChemSpider 114193 YesY
Jmol-3D images Image
Image
KEGG C05905 YesY
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).
 N verify (what isYesY/N?)
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 but not limited to 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.[citation needed]

Effects on the human body[edit]

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.[citation needed] 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[edit]

References[edit]

  1. ^ http://www.phytochemicals.info/phytochemicals/cyanidin.php[self-published source?]
  2. ^ a b 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. 
  3. ^ Johnson, Kelly. "Health Benefits of Cyanidin". 10 April 2015. Retrieved 13 August 2015. 
  4. ^ 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. PMID 15003523. 
  5. ^ 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. 
  6. ^ 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. 
  7. ^ 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. 
  8. ^ Tulio, Artemio Z.; Reese, R. Neil; Wyzgoski, Faith J.; Rinaldi, Peter L.; Fu, Ruiling; Scheerens, Joseph C.; Miller, A. Raymond (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. 
  9. ^ Anthocyanins and Their Variation in Red Wines I. Monomeric Anthocyanins and Their Color Expression. Fei He, Na-Na Liang, Lin Mu, Qiu-Hong Pan, Jun Wang, Malcolm J. Reeves and Chang-Qing Duan, Molecules, 2012, 17, pages 1571-1601, doi:10.3390/molecules17021571