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
CAS Number	18719-76-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16726 ;
ChEMBL	ChEMBL592218 ;
ChemSpider	27186 ;
ECHA InfoCard	100.038.646
PubChem CID	29231;
UNII	V0N2VMB4FV ;
CompTox Dashboard (EPA)	DTXSID00927864 ;
	InChI InChI=1S/C27H30O15.ClH/c1-9-19(32)21(34)23(36)26(39-9)38-8-18-20(33)22(35)24(37)27(42-18)41-17-7-12-14(30)5-11(28)6-16(12)40-25(17)10-2-3-13(29)15(31)4-10;/h2-7,9,18-24,26-27,32-37H,8H2,1H3,(H3-,28,29,30,31);1H/t9-,18+,19-,20+,21+,22-,23+,24+,26+,27+;/m0./s1 Key: ADZHXBNWNZIHIX-XYGAWYNKSA-N ; InChI=1S/C27H30O15.ClH/c1-9-19(32)21(34)23(36)26(39-9)38-8-18-20(33)22(35)24(37)27(42-18)41-17-7-12-14(30)5-11(28)6-16(12)40-25(17)10-2-3-13(29)15(31)4-10;/h2-7,9,18-24,26-27,32-37H,8H2,1H3,(H3-,28,29,30,31);1H/t9-,18+,19-,20+,21+,22-,23+,24+,26+,27+;/m0./s1; Key: ADZHXBNWNZIHIX-XYGAWYNKSA-N;
	SMILES [Cl-].O(C[C@H]4O[C@@H](Oc2cc3c(O)cc(O)cc3[o+]c2c1ccc(O)c(O)c1)[C@H](O)[C@@H](O)[C@@H]4O)[C@@H]5O[C@H]([C@H](O)[C@@H](O)[C@H]5O)C;
Properties
Chemical formula	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. doi:10.1042/bj0240753. PMC 1254517. PMID 16744416.
Gilbert, R.I. (1971). "An unusual anthocyanin in Antirrhinum majus". Phytochemistry. 10 (11): 2848–2849. 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. S2CID 94388806.
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. 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.
Solomon, A; Golubowicz, S; Yablowicz, Z; Grossman, S; Bergman, M; Gottlieb, HE; Altman, A; Kerem, Z; Flaishman, MA (2006). "Antioxidant activities and anthocyanin content of fresh fruits of common fig (Ficus carica L.)". J Agric Food Chem. 54 (20): 7717–23. doi:10.1021/jf060497h. PMID 17002444.

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[1] Scott-Moncrieff, R (1930). "Natural anthocyanin pigments: The magenta flower pigment of Antirrhinum majus". Biochemical Journal. 24 (3): 753–766. doi:10.1042/bj0240753. PMC 1254517. PMID 16744416.

[2] Gilbert, R.I. (1971). "An unusual anthocyanin in Antirrhinum majus". Phytochemistry. 10 (11): 2848–2849. 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. S2CID 94388806.

[pmid18290621-5] 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. 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] Solomon, A; Golubowicz, S; Yablowicz, Z; Grossman, S; Bergman, M; Gottlieb, HE; Altman, A; Kerem, Z; Flaishman, MA (2006). "Antioxidant activities and anthocyanin content of fresh fruits of common fig (Ficus carica L.)". J Agric Food Chem. 54 (20): 7717–23. doi:10.1021/jf060497h. PMID 17002444.