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 unflagged free DOI (link)
- ↑ 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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3-Hydroxyanthocyanidins |
- 5-Desoxy-peonidin
- Aurantinidin
- Cyanidin
- 6-Hydroxycyanidin
- Delphinidin
- Fisetinidin
- Guibourtinidin
- Pelargonidin
- Robinetinidin
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3-Deoxyanthocyanidins |
- Apigeninidin
- Columnidin
- Diosmetinidin
- Gesneridin
- Luteolinidin
- Tricetinidin
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O-Methylated anthocyanidins |
- 5-Desoxy-malvidin
- Capensinidin
- Europinidin
- Hirsutidin
- Kaempferidinidin
- Malvidin
- Peonidin
- Petunidin
- Pulchellidin
- Rosinidin
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Anthocyanins (anthocyaninidin glycosides) | Glucosides:
- Callistephin (Pelargonidin 3-O-glucoside)
- Chrysanthemin (Cyanidin 3-O-glucoside)
- Myrtillin (Delphinidin 3-O-glucoside)
- Oenin (Malvidin 3-O-glucoside)
- Peonidin 3-O-glucoside
- Petunidin 3-O-glucoside
- Pulchellidin 3-glucoside
Diglucosides:
- Cyanin (Cyanidin 3,5-O-diglucoside)
- Delphin (Delphinidin 3,5-O-diglucoside)
- Malvin (Malvidin 3,5-diglucoside)
- Pelargonin (Pelargonidin 3,5-O-diglucoside)
- Peonin (Peonidin 3,5-O-diglucoside)
- Petunin (Petunidin 3,5-O-diglucoside)
Others glycosides:
- Antirrhinin (Cyanidin 3-O-rutinoside)
- Ideain (Cyanidin 3-O-galactoside)
- Delphinidin 3-O-rhamnoside
- Petunidin 3-O-arabinoside
- Petunidin 3-O-galactoside
- Petunidin 3-O-rhamnoside
- Petunidin 3-O-rutinoside
- Primulin (Malvidin 3-O-galactoside)
- Pulchellidin 3-rhamnoside
- Tulipanin (Delphinidin 3-O-rutinoside)
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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
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Coumaroylated anthocyanins (cis- and trans-) |
- Cyanidin 3-O-(6-p-coumaroyl)glucoside
- Delphinidin 3-O-(6-p-coumaroyl)glucoside
- Malvidin 3-O-(6-p-coumaroyl)glucoside
- Petunidin 3-O-(6-p-coumaroyl)glucoside
- Peonidin 3-O-(6-p-coumaroyl)glucoside
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Caffeoylated anthocyanins |
- Malvidin 3-O-(6-p-caffeoyl)glucoside
- Peonidin 3-O-(6-p-caffeoyl)glucoside
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Malonylated anthocyanins |
- Malonylmalvin (malvidin 3-(6″-malonylglucoside)-5-glucoside)
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Acylated anthocyanin diglycosides |
- Cyanidin 3-O-(di-p-coumarylglucoside)-5-glucoside
- Gentiodelphin (delphinidin 3-''O''-glucosyl-5-''O''-(6-''O''-caffeoyl-glucosyl)-3′-''O''-(6-''O''-caffeoyl-glucoside))
- Nasunin (Delphinidin 3-(p-coumaroylrutinoside)-5-glucoside)
- Petanin (petunidin 3-[6-O-(4-O-(E)-p-coumaroyl-O-α-l-rhamnopyranosyl)-β-D-glucopyranoside]-5-O-β-D-glucopyranoside)
- Violdelphin (Delphinidin 3-rutinoside-7-O-(6-O-(4-(6-O-(4-hydroxybenzoyl)-β-D-glucosyl)oxybenzoyl)-β-D-glucoside)
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Flavanol-anthocyanin adducts |
- Malvidin glucoside-ethyl-catechin
- Catechin(4α→8)pelargonidin 3-O-β-glucopyranoside
- Epicatechin(4α→8)pelargonidin 3-O-β-glucopyranoside
- Afzelechin(4α→8)pelargonidin 3-O-β-glucopyranoside
- Epiafzelechin(4α→8)pelargonidin 3-O-β-glucopyranoside
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Miscellaneous |
- Metalloanthocyanins (commelinin)
- Cyanosalvianin
- Protocyanin
- Protodelphin)
- Pyranoanthocyanins
- Copigmentation
- Anthocyanone A (degradation product of oenin)
- Malvone (oxidation product of malvin)
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