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.[1][2]
This type of compound has a better color stability at pH 5.5 than normal anthocyanins. When the pH was increased from 2.2 to 5.5, the solution of the pigment became progressively more violet (λmax = 560 nm at pH 5.5), whereas similar solutions of the anthocyanin were almost colorless at pH 4.0.[3]
References
- ^ Morata, A; González, C; Suárez-Lepe, JA (2007). "Formation of vinylphenolic pyranoanthocyanins by selected yeasts fermenting red grape musts supplemented with hydroxycinnamic acids". International Journal of Food Microbiology. 116 (1): 144–52. doi:10.1016/j.ijfoodmicro.2006.12.032. PMID 17303275.
- ^ Asenstorfer, Robert E.; Lee, David F.; Jones, Graham P. (2006). "Influence of structure on the ionisation constants of anthocyanin and anthocyanin-like wine pigments". Analytica Chimica Acta. 563 (1–2): 10–14. doi:10.1016/j.aca.2005.09.040.
- ^ Escribano-Bailón, Teresa; Álvarez-García, Marta; Rivas-Gonzalo, Julian C.; Heredia, Francisco J.; Santos-Buelga, Celestino (2001). "Color and Stability of Pigments Derived from the Acetaldehyde-Mediated Condensation between Malvidin 3-O-Glucoside and (+)-Catechin". Journal of Agricultural and Food Chemistry. 49 (3): 1213–7. doi:10.1021/jf001081l. hdl:10366/141044. PMID 11312838.
See also
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3-Hydroxyanthocyanidins | |
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3-Deoxyanthocyanidins | |
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O-Methylated anthocyanidins | |
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Anthocyanins (anthocyaninidin glycosides) | Glucosides:
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-) | |
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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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- 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 | |
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