Vitisin A (pyranoanthocyanin)

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Vitisin A
Vitisin A.svg
Names
IUPAC name
5′′-Formyl-3-(β-D-glucopyranosyloxy)-4′,7-dihydroxy-3′,5′-dimethoxy-6′′-oxo-1,6′′-dihydropyrano[4′′,3′′,2′′:4,5]flavylium
Preferred IUPAC name
3-Formyl-8-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-2-oxo-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-pyrano[4,3,2-de][1]benzopyran-6-ium
Other names
Malvidin 3-O-glucoside pyruvic acid
Malvidin 3-O-glucoside pyruvic adduct
5-carboxypyranomalvidin-3-glucoside
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C26H24O14/c1-35-14-3-9(4-15(36-2)19(14)30)23-24(40-26-22(33)21(32)20(31)16(8-28)39-26)17-11(7-27)25(34)38-13-6-10(29)5-12(37-23)18(13)17/h3-7,16,20-22,26,28-33H,8H2,1-2H3/p+1/t16-,20-,21+,22-,26+/m1/s1
    Key: DYYPRYJWENTOEN-DMRYIZGCSA-O
  • O=CC1=C2C3=C(OC1=O)C=C(O)C=C3[O+]([H])C(C4=CC(OC)=C(O)C(OC)=C4)=C2O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O
Properties
C26H25O14+
Molar mass 561.46 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Vitisin A is a natural phenol found in red wines. [1] [2] [3] It is a pyranoanthocyanin. [4] [5]

Contents

See also

Related Research Articles

Grape Edible berry of a flowering plant in the family Vitaceae

A grape is a fruit, botanically a berry, of the deciduous woody vines of the flowering plant genus Vitis.

Polyphenol Class of chemical compounds

Polyphenols are a large family of naturally occurring organic compounds characterized by multiples of phenol units. They are abundant in plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and for tanning garments.

Proanthocyanidins are a class of polyphenols found in many plants, such as cranberry, blueberry, and grape seeds. Chemically, they are oligomeric flavonoids. Many are oligomers of catechin and epicatechin and their gallic acid esters. More complex polyphenols, having the same polymeric building block, form the group of tannins.

Thearubigins are polymeric polyphenols that are formed during the enzymatic oxidation and condensation of two gallocatechins with the participation of polyphenol oxidases during the fermentation reactions in black tea. Thearubigins are red in colour and are responsible for much of the staining effect of tea. Therefore, a black tea often appears red while a green or white tea has a much clearer appearance. The colour of a black tea, however, is affected by many other factors as well, such as the amount of theaflavins, another oxidized form of polyphenols.

Phenolic content in wine

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.

Wine color

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.

Procyanidin C2 Chemical compound

Procyanidin C2 is a B type proanthocyanidin trimer, a type of condensed tannin.

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.

Grandinin Chemical compound

Grandinin is an ellagitannin. It can be found in Melaleuca quinquenervia leaves and in oaks species like the North American white oak and European red oak. It shows antioxydant activity. It is an astringent compound. It is also found in wine, red or white, aged in oak barrels.

Syringic acid Chemical compound

Syringic acid is a naturally occurring phenolic compound and dimethoxybenzene that is commonly found as a plant metabolite.

Naturally occurring phenols Group of chemical compounds

In biochemistry, naturally occurring phenols refers to phenol functional group that is found in natural products. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants.

Grape reaction product Chemical compound

The grape reaction product is a phenolic compound explaining the disappearance of caftaric acid from grape must during processing. It is also found in aged red wines. Its enzymatic production by polyphenol oxidase is important in limiting the browning of musts, especially in white wine production. The product can be recreated in model solutions.

Vitisin B (pyranoanthocyanin) Chemical compound

Vitisin B is a natural phenol found in red wines. It is a pyranoanthocyanin.

Hopeaphenol Chemical compound

Hopeaphenol is a stilbenoid. It is a resveratrol tetramer. It has been first isolated from Dipterocarpaceae like Shorea ovalis. It has also been isolated from wines from North Africa.

Pinotin

Pinotins are a type of pyranoanthocyanins, a class of phenolic compounds found in red wine. One such compound is pinotin A.

Wine chemistry

Wine is a complex mixture of chemical compounds in a hydro-alcoholic solution with a pH around 4.

Pinotin A Chemical compound

Pinotin A is a pinotin, a type of pyranoanthocyanins and a class of phenolic compounds found in red wine.

Proteins are present in wine. The most common proteins include thaumatin-like proteins and chitinases and have a role in the formation of turbidity (haze) especially visible in white wine. The quantity of haze forming is dependent on the quantity of phenolics in the wine.

Malvidin glucoside-ethyl-catechin 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.

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.

References

  1. Brazilian red wines made from the hybrid grape cultivar Isabel: Phenolic composition and antioxidant capacity. Suzana Lucy Nixdorf and Isidro Hermosín-Gutiérrez, Analytica Chimica Acta, Volume 659, Issues 1-2, 5 February 2010, Pages 208-215, doi : 10.1016/j.aca.2009.11.058
  2. Formation of vitisin A during red wine fermentation and maturation. Robert E. Asenstrfer, Andrew J. Markides, Patrick G. Iland and Graham P. Jones, Australian Journal of Grape and Wine Research, Volume 9, Issue 1, pages 40–46, April 2003, doi : 10.1111/j.1755-0238.2003.tb00230.x
  3. Vitisin A content in chilean wines from Vitis vinifera cv. cabernet sauvignon and contribution to the color of aged red wines. Schwarz Michael, Quast Peter, Von Baer Dietrich and Winterhalter Peter, Journal of agricultural and food chemistry, 2003, vol. 51, no21, pp. 6261-626, INIST : 15183115
  4. Charge equilibria and pK values of 5-carboxypyranomalvidin-3-glucoside (vitisin A) by electrophoresis and absorption spectroscopy. Robert E. Asenstorfer and Graham P. Jones, Tetrahedron, Volume 63, Issue 22, 28 May 2007, Pages 4788-4792, doi : 10.1016/j.tet.2007.03.052
  5. Effect of acetaldehyde and several acids on the formation of vitisin A in model wine anthocyanin and colour evolution. Romero C. and Bakker J., International journal of food science & technology, 2000, vol. 35, no. 1, pp. 129-140, INIST : 1283952