Antirrhinin
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| Names | |
|---|---|
| IUPAC name
(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxane-3,4,5-triol chloride | |
| Other names
Keracyanin Prunicyanin Sambucin Cyaninoside Keraciannai Keracyanine Keracyaninum Cyanidin 3-rutinoside Cyanidin 3-O-rutinoside Keracyanin chloride cyanidin-3-rhamnoglucoside | |
| Identifiers | |
18719-76-1  | |
| ChEBI | CHEBI:16726  |
| ChEMBL | ChEMBL592218 |
| ChemSpider | 27186 |
| Jmol interactive 3D | Image |
| PubChem | 29231 |
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| Properties | |
| C27H31O15+, Cl− | |
| Molar mass | 630.97 g/mol (chloride) 595.52 g/mol (cation) |
| 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 | |
Antirrhinin is an anthocyanin. It is the 3-rutinoside of cyanidin.
Occurrence
It can be found in Antirrhinum majus (common snapdragon).[1][2]
It can be found in blackcurrant,[3] açaí,[4] black raspberry,[5] litchi pericarp[6] and common fig.[7]
Metabolism
Cyanidin 3-O-rutinoside 5-O-glucosyltransferase uses UDP-glucose and cyanidin 3-O-rutinoside (antirrhinin) to produce UDP and cyanidin 3-O-rutinoside 5-O-beta-D-glucoside.
References
- ↑ Scott-Moncrieff, R (1930). "Natural anthocyanin pigments: The magenta flower pigment of Antirrhinum majus". Biochemical Journal 24 (3): 753–766. PMC 1254517. PMID 16744416.
- ↑ Gilbert, R.I. (1971). "An unusual anthocyanin in Antirrhinum majus". Phytochemistry 10 (11): 2848. doi:10.1016/S0031-9422(00)97309-6.
- ↑ Slimestad, Rune; Solheim, Haavard (2002). "Anthocyanins from Black Currants (Ribes nigrumL.)". Journal of Agricultural and Food Chemistry 50 (11): 3228–31. doi:10.1021/jf011581u. PMID 12009991.
- ↑ Gallori, S.; Bilia, A. R.; Bergonzi, M. C.; Barbosa, W. L. R.; Vincieri, F. F. (2004). "Polyphenolic Constituents of Fruit Pulp of Euterpe oleracea Mart. (Açai palm)". Chromatographia 59 (11–12). doi:10.1365/s10337-004-0305-x.
- ↑ 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.
- ↑ Sarni-Manchado, Pascale; Le Roux, Erwan; Le Guernevé, Christine; Lozano, Yves; Cheynier, Véronique (2000). "Phenolic Composition of Litchi Fruit Pericarp". Journal of Agricultural and Food Chemistry 48 (12): 5995–6002. doi:10.1021/jf000815r. PMID 11312772.
- ↑ Antioxidant activities and anthocyanin content of fresh fruits of common fig (Ficus carica L.). Solomon A, Golubowicz S, Yablowicz Z, Grossman S, Bergman M, Gottlieb HE, Altman A, Kerem Z and Flaishman MA, J Agric Food Chem., 2006 Oct 4, 54(20), pages 7717-7723, PubMed
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