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p-Coumaroylated anthocyanin

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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).

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.

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.

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.

See also

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.
Anthocyanidins and their anthocyanin glucosides
3-Hydroxyanthocyanidins
3-Deoxyanthocyanidins
O-Methylated anthocyanidins
Anthocyanins
(anthocyaninidin glycosides)
Glucosides:

Diglucosides:

Others glycosides:

Acylated anthocyanins
Acetylated anthocyanins
  • Cyanidin 3-O-(6-acetyl)glucoside
  • Delphinidin 3-O-(6-acetyl)glucoside
  • Malvidin 3-O-(6-acetyl)glucoside
  • Petunidin 3-O-(6-acetyl)galactoside
  • Petunidin 3-O-(6-acetyl)glucoside
  • Peonidin 3-O-(6-acetyl)glucoside
  • Coumaroylated anthocyanins
    (cis- and trans-)
    Caffeoylated anthocyanins
    Malonylated anthocyanins
    Acylated anthocyanin diglycosides
    Flavanol-anthocyanin adducts
    Miscellaneous


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