Antirrhinin

Antirrhinin
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 N
ChEBI CHEBI:16726 YesY
ChEMBL ChEMBL592218 YesY
ChemSpider 27186 YesY
Jmol interactive 3D Image
PubChem 29231
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).
N verify (what is YesYN ?)
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

  1. Scott-Moncrieff, R (1930). "Natural anthocyanin pigments: The magenta flower pigment of Antirrhinum majus". Biochemical Journal 24 (3): 753–766. PMC 1254517. PMID 16744416.
  2. Gilbert, R.I. (1971). "An unusual anthocyanin in Antirrhinum majus". Phytochemistry 10 (11): 2848. doi:10.1016/S0031-9422(00)97309-6.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
  7. 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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