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
KEGG	C04491 ;
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[edit]

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[edit]

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[edit]

^ 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 (1971). "An unusual anthocyanin in Antirrhinum majus". Phytochemistry. 10 (11): 2848–2849. Bibcode:1971PChem..10.2848G. doi:10.1016/S0031-9422(00)97309-6.
^ Slimestad R, Solheim H (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 AR, Bergonzi MC, Barbosa WL, Vincieri FF (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 P, Le Roux E, Le Guernevé C, Lozano Y, Cheynier V (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 (1971). "An unusual anthocyanin in Antirrhinum majus". Phytochemistry. 10 (11): 2848–2849. Bibcode:1971PChem..10.2848G. doi:10.1016/S0031-9422(00)97309-6.

[3] Slimestad R, Solheim H (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 AR, Bergonzi MC, Barbosa WL, Vincieri FF (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 P, Le Roux E, Le Guernevé C, Lozano Y, Cheynier V (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.

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