p-Coumaroylated anthocyanin

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]

References

^ 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
^ Delphinidin 3-(6-p-coumaroyl)glucoside synthesis reaction on www.kegg.jp
^ 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
^ 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.

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[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.

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p-Coumaroylated anthocyanin

See also

References