Antirrhinin

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Antirrhinin
Keracyanin.svg
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.038.646 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: ADZHXBNWNZIHIX-XYGAWYNKSA-N Yes check.svgY
  • 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
  • [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
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Antirrhinin is an anthocyanin. It is the 3-rutinoside of cyanidin.

Contents

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.

Related Research Articles

<i>Rubus idaeus</i> Red raspberry

Rubus idaeus is a red-fruited species of Rubus native to Europe and northern Asia and commonly cultivated in other temperate regions.

<span class="mw-page-title-main">Açaí palm</span> Palm tree with many uses, mainly fruit as cash crop

The açaí palm, Euterpe oleracea, is a species of palm tree (Arecaceae) cultivated for its fruit, hearts of palm, leaves, and trunk wood. Global demand for the fruit has expanded rapidly in the 21st century, and the tree is cultivated for that purpose primarily.

<span class="mw-page-title-main">Delphinidin</span> Chemical compound

Delphinidin is an anthocyanidin, a primary plant pigment, and also an antioxidant. Delphinidin gives blue hues to flowers in the genera Viola and Delphinium. It also gives the blue-red color of the grape variety Cabernet Sauvignon, and can be found in cranberries and Concord grapes as well as pomegranates, and bilberries.

<span class="mw-page-title-main">Cyanidin</span> Anthocyanidin pigment in flowering plant petals and fruits

Cyanidin is a natural organic compound. It is a particular type of anthocyanidin. It is a pigment found in many red berries including grapes, bilberry, blackberry, blueberry, cherry, chokeberry, cranberry, elderberry, hawthorn, loganberry, açai berry and raspberry. 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. Cyanidin has been found to be a potent sirtuin 6 (SIRT6) activator.

<span class="mw-page-title-main">Antioxidant effect of polyphenols and natural phenols</span>

A polyphenol antioxidant is a hypothetized type of antioxidant, in which each instance would contain a polyphenolic substructure; such instances which have been studied in vitro. Numbering over 4,000 distinct chemical structures, such polyphenols may have antioxidant activity {{{1}}} in vitro (although they are unlikely to be antioxidants in vivo). Hypothetically, they may affect cell-to-cell signaling, receptor sensitivity, inflammatory enzyme activity or gene regulation, although high-quality clinical research has not confirmed any of these possible effects in humans as of 2020.

<span class="mw-page-title-main">Malvin</span> Chemical compound

Malvin is a naturally occurring chemical of the anthocyanin family.

<span class="mw-page-title-main">Anthocyanin</span> Class of chemical compounds

Anthocyanins, also called anthocyans, are water-soluble vacuolar pigments that, depending on their pH, may appear red, purple, blue, or black. In 1835, the German pharmacist Ludwig Clamor Marquart gave the name Anthokyan to a chemical compound that gives flowers a blue color for the first time in his treatise "Die Farben der Blüthen". Food plants rich in anthocyanins include the blueberry, raspberry, black rice, and black soybean, among many others that are red, blue, purple, or black. Some of the colors of autumn leaves are derived from anthocyanins.

<span class="mw-page-title-main">Phenolic content in wine</span> Wine chemistry

The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.

<span class="mw-page-title-main">Wine color</span> Wine characteristic

The color of wine is one of the most easily recognizable characteristics of wines. Color is also an element in wine tasting since heavy wines generally have a deeper color. The accessory traditionally used to judge the wine color was the tastevin, a shallow cup allowing one to see the color of the liquid in the dim light of a cellar. The color is an element in the classification of wines.

<span class="mw-page-title-main">Isorhamnetin</span> Chemical compound

Isorhamnetin is an O-methylated flavon-ol from the class of flavonoids. A common food source of this 3'-methoxylated derivative of quercetin and its glucoside conjugates are pungent yellow or red onions, in which it is a minor pigment, quercetin-3,4'-diglucoside and quercetin-4'-glucoside and the aglycone quercetin being the major pigments. Pears, olive oil, wine and tomato sauce are rich in isorhamnetin. Almond skin is a rich source of isorhamnetin-3-O-rutinoside and isorhamnetin-3-O-glucoside, in some cultivars they comprise 75% of the polyphenol content, the total of which can exceed 10 mg/100 gram almond. Others sources include the spice, herbal medicinal and psychoactive Mexican tarragon (Tagetes lucida), which is described as accumulating isorhamnetin and its 7-O-glucoside derivate. Nopal is also a good source of isorhamnetin, which can be extracted by supercritical fluid extraction assisted by enzymes.

<span class="mw-page-title-main">Purple corn</span> Variety of flint maize

Purple corn or purple maize is group of flint maize varieties originating in South America, descended from a common ancestral variety termed "kʼculli" in Quechua. It is most commonly grown in the Andes of Peru, Bolivia and Ecuador.

<span class="mw-page-title-main">Chrysanthemin</span> Chemical compound

Chrysanthemin is an anthocyanin. It is the 3-glucoside of cyanidin.

<span class="mw-page-title-main">Myrtillin</span> Chemical compound

Myrtillin is an anthocyanin. It is the 3-glucoside of delphinidin. It can be found in all green plants, most abundantly in black beans, blackcurrant, blueberry, huckleberry, bilberry leaves and in various myrtles, roselle plants, and Centella asiatica plant. It is also present in yeast and oatmeal. The sumac fruit's pericarp owes its dark red colour to anthocyanin pigments, of which chrysanthemin, myrtillin and delphinidin have yet been identified.

The pyranoanthocyanins are a type of pyranoflavonoids. They are chemical compounds formed in red wines by yeast during fermentation processes or during controlled oxygenation processes during the aging of wine. The different classes of pyranoanthocyanins are carboxypyranoanthocyanins, methylpyranoanthocyanins, pyranoanthocyanin-flavanols, pyranoanthocyanin-phenols, portisins, oxovitisins and pyranoanthocyanin dimers; their general structure includes an additional ring that may have different substituents linked directly at C-10.

<span class="mw-page-title-main">Syringetin</span> Chemical compound

Syringetin is an O-methylated flavonol, a type of flavonoid. It is found in red grape, in Lysimachia congestiflora and in Vaccinium uliginosum. It is one of the phenolic compounds present in wine.

<span class="mw-page-title-main">Malvidin glucoside-ethyl-catechin</span> Chemical compound

Malvidin glucoside-ethyl-catechin is a flavanol-anthocyanin adduct. Flavanol-anthocyanin adducts are formed during wine ageing through reactions between anthocyanins and tannins present in grape, with yeast metabolites such as acetaldehyde. Acetaldehyde-induced reactions yield ethyl-linked species such as malvidin glucoside-ethyl-catechin.

<span class="mw-page-title-main">Flavanol-anthocyanin adduct</span>

Flavanol-anthocyanin adducts are formed during wine ageing through reactions between anthocyanins and tannins present in grape, with yeast metabolites such as acetaldehyde. Acetaldehyde-induced reactions yield ethyl-linked species such as malvidin glucoside-ethyl-catechin.

Cyanidin-3-O-glucoside 2-O-glucuronosyltransferase is an enzyme with systematic name UDP-D-glucuronate:cyanidin-3-O-beta-D-glucoside 2-O-beta-D-glucuronosyltransferase. This enzyme catalyses the following chemical reaction

<span class="mw-page-title-main">Ideain</span> Chemical compound

Ideain, the cyanidin 3-O-galactoside, is an anthocyanin, a type of plant pigment.

Purple sweet potato color (PSPC) is a natural anthocyanin food coloring obtained from the sweet potato. Some cultivars, like the Ayamurasaki, released in Japan in 1995, are specially developed to have a higher anthocyanin content.

References

  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.
  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.