P-Coumaroylated anthocyanin

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Malvidin-3-O-(6-p-coumaroyl)glucoside Mv3Gcoum.PNG
Malvidin-3-O-(6-p-coumaroyl)glucoside

p-Coumaroylated anthocyanins are a type of anthocyanins with a p-coumaric acid unit linked with a sugar to an anthocyanidin aglycone. 3-(6-p-Coumaroyl)glucosides are found in grape and wine. Cyanidin-3-O-(di-p-coumarylglucoside)-5-glucoside is found in dark opal basil. Red leaves of Perilla frutescens also accumulate cyanidin 3-(6-O-p-coumaroyl-β-D-glucoside)-5-(6-O-malonyl-β-D-glucoside). [1]

Delphinidin 3-(6-p-coumaroyl)glucoside is formed by the enzyme anthocyanin 3-O-glucoside 6″-O-hydroxycinnamoyltransferase from delphinidin 3-O-glucoside and p-coumaroyl-CoA in the anthocyanin biosynthesis pathway. [2]

Red-berries vines of the Pinot varieties are known to not synthesize acetylated or para-coumaroylated anthocyanins, as other grape varietals do, only glucosylated anthocyanins. [3]

Anthocyanin 5-aromatic acyltransferase is an enzyme that uses hydroxycinnamoyl-CoA and anthocyanidin-3,5-diglucoside to produce CoA and anthocyanidin 3-glucoside-5-hydroxycinnamoylglucoside. This enzyme can be found in Gentiana triflora . [4]

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<i>Vitis vinifera</i> Species of flowering plant in the grape vine family Vitaceae

Vitis vinifera, the common grape vine, is a species of Vitis, native to the Mediterranean region, Central Europe, and southwestern Asia, from Morocco and Portugal north to southern Germany and east to northern Iran. There are currently between 5,000 and 10,000 varieties of Vitis vinifera grapes though only a few are of commercial significance for wine and table grape production.

Delphinidin

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 that produces Cabernet Sauvignon, and can be found in cranberries and Concord grapes as well as pomegranates, and bilberries.

Cyanidin anthocyanidin pigment in flowering plant 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, 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.

In enzymology, a dihydrokaempferol 4-reductase (EC 1.1.1.219) is an enzyme that catalyzes the chemical reaction

In enzymology, an anthocyanin 5-aromatic acyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, an anthocyanin 5-O-glucoside 6'''-O-malonyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, an anthocyanin 6"-O-malonyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, an anthocyanidin 3-O-glucosyltransferase is an enzyme that catalyzes the chemical reaction

<i>Gentiana triflora</i>

Gentiana triflora is a tall, flowering perennial plant in the genus Gentiana native to higher-elevation meadows and forests of China, Mongolia, Eastern Russia, Korea and Japan.

Anthocyanin

Anthocyanins are water-soluble vacuolar pigments that, depending on their pH, may appear red, purple, blue or black. 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.

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.

Petunidin

Petunidin (Pt), like Europinidin and Malvidin, is derived from Delphinidin and is an O-methylated anthocyanidin of the 3-hydroxy type. It is a natural organic compound, a dark-red or purple water-soluble pigment found in many redberries including chokeberries, Saskatoon berries or different species of grape, and also part of the pigments responsible for the petal colors in many flowers. This pigment gives the Indigo Rose tomatoes the majority of their deep purple color when the fruits are exposed to sunlight. The name of the molecule itself is derived from the word Petunia.

Myrtillin

Myrtillin is an anthocyanin. It is the 3-glucoside of delphinidin. It can be found in all green plants, most abundantly in 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.

Coumaroyl-coenzyme A is a chemical compound found in plants. The compound is the thioester of coenzyme-A and coumaric acid.

Delphinidin-3-<i>O</i>-(6-<i>p</i>-coumaroyl)glucoside

Delphinidin 3-O-(6-p-coumaroyl)glucoside is a p-coumaroylated anthocyanin. It can be found in some red Vitis vinifera grape cultivars and in red wine.

Malvidin-3-<i>O</i>-(6-<i>p</i>-coumaroyl)glucoside

Malvidin-3-O-(6-p-coumaroyl)glucoside is a p-coumaroylated anthocyanin found in grape and wine. There are two forms with the cis and trans isomers of p-coumaric acid. It is a cation.

Anthocyanin 3-O-glucoside 6″-O-hydroxycinnamoyltransferase is an enzyme forming delphinidin 3-(6-p-coumaroyl)glucoside from delphinidin 3-O-glucoside (myrtillin) and p-coumaroyl-CoA.

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

Basics of blue flower colouration

Blue flower colour was always associated with something unusual and desired. Blue roses especially were assumed to be a dream that cannot be realised. Blue colour in flower petals is caused by anthocyanins, which are members of flavonoid class metabolites. We can diversify three main classes of anthocyanin pigments: cyaniding type responsible for red coloration, pelargonidin type responsible for orange colour and delphinidin type responsible for violet/blue flower and fruits coloration. The main difference in the structure of listed anthocyanins type is the number of hydroxyl groups in the B-ring of the anthocyanin. Nevertheless in the monomeric state anthocyanins never show blue colour in the weak acidic and neutral pH. The mechanism of blue colour formation are very complicated in most cases, presence of delphinidin type pigments is not sufficient, great role play also the pH and the formation of complexes of anthocyanins with flavones and metal ions.

References

  1. Purification and characterization of anthocyanin 3-aromatic acyltransferase from Perilla frutescens. Fujiwara H, Tanaka Y, Fukui Y, Ashikari T, Yamaguchi M and Kusumi T, Plant Science, 1998, vol. 137, no1, pages 87-94, INIST : 2414423
  2. Delphinidin 3-(6-p-coumaroyl)glucoside synthesis reaction on www.kegg.jp
  3. Biosynthesis of Anthocyanins and Their Regulation in Colored Grapes. Fei He, Lin Mu, Guo-Liang Yan, Na-Na Liang, Qiu-Hong Pan, Jun Wang, Malcolm J. Reeves and Chang-Qing Duan, Molecules, 2010, 15, pages 9057-9091, doi : 10.3390/molecules15129057
  4. Fujiwara H, Tanaka Y, Fukui Y, Nakao M, Ashikari T, Kusumi T (1997). "Anthocyanin 5-aromatic acyltransferase from Gentiana triflora Purification, characterization and its role in anthocyanin biosynthesis". Eur. J. Biochem. 249 (1): 45–51. doi: 10.1111/j.1432-1033.1997.t01-1-00045.x . PMID   9363752.