Skip to main content
Log in

Chemical transformations of anthocyanins yielding a variety of colours (Review)

  • Review article
  • Published:
Environmental Chemistry Letters Aims and scope Submit manuscript

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13
Fig. 14
Fig. 15

References

  • Bakker J, Bridle P, Honda T, Kuwano H, Saito N, Terahara N, Timberlake CF (1997) Isolation and identification of a new anthocyanin occurring in some red wines. Phytochemistry 44:1375–1382

    Article  CAS  Google Scholar 

  • Bakker J, Picinelli A, Bridle P (1993) Model wine solutions: Colour and composition changes during ageing. Vitis 32:111–118

    CAS  Google Scholar 

  • Bakker J, Timberlake CF (1997) Isolation, identification, and characterization of new color-stable anthocyanins occurring in some red wines. J Agric Food Chem 45:35–43

    Article  CAS  Google Scholar 

  • Bendz G, Martensson O, Nilsson E (1967) Studies of flavylium compounds. I. Some flavylium compounds and their properties. Arkiv Kemi 27:67–77

    Google Scholar 

  • Brouillard R, Dangles O (1994) Anthocyanin molecular interactions: the first step in the formation of new pigments during wine ageing. Food Chem 51:365–371

    Article  CAS  Google Scholar 

  • Brouillard R, Delaporte B, El Hage Chahine JM, Dubois JE (1979) Chimiedes pigments anthocyaniques. 4. Spectre d’absorption UV-visible de la forme chalcone de la glucoside-3 malvine. J Chim Phys 76:273–276

    CAS  Google Scholar 

  • Brouillard R, Mazza G, Saad Z, Albrecht-Gary AM, Cheminat A (1989) The copigmentation reaction of anthocyanins: a microprobe for the structural study of aqueous solutions. J Am Chem Soc 111:2604–2610

    Article  CAS  Google Scholar 

  • Escribano-Bailón T, Dangles O, Brouillard R (1996) Coupling reactions between flavylium ions and catechin. J Agric Food Chem 41:1583–1592

    Google Scholar 

  • Francia-Aricha EM, Guerra MT, Rivas-Gonzalo JC, Santos-Buelga C (1997) New anthocyanin pigments formed after condensation with flavanols. J Agric Food Chem 45:2262–2265

    Article  CAS  Google Scholar 

  • Fulcrand H, Benabdeljalil C, Rigaud J, Cheynier V, Moutounet MA (1998) new class of wine pigments generated by reaction between pyruvic acid and grape anthocyanins. Phytochemistry 47:1401–1407

    Article  CAS  Google Scholar 

  • Fulcrand H, Cameira dos Santos PJ, Sarni-Manchado P, Cheynier V, Bonvin JF (1996) Structure of a new anthocyanin-derived wine pigment. J Chem Soc Perkin Trans 1 1996:735–739

    Article  Google Scholar 

  • Giusti MM, Rodriguez-Saona LE, Wrolstad RE (1999) Molar absorptivity and color characteristics of acylated and non-acylated pelargonidin-based anthocyanins. J Agric Food Chem 47:4631–4637

    Article  CAS  Google Scholar 

  • Harborne JB, (1984) Phytochemical methods, 2nd edn. Chapman & Hall, London

    Google Scholar 

  • Jurd L, Gueissman TA (1963) Anthocyanins and related compounds. II. Structural transformations of some anhydrobases. J Org Chem 28:2394–2397

    Article  CAS  Google Scholar 

  • Liao H, Cai Y, Haslam E (1992) Polyphenol interactions. Anthocyanins: Copigmentation and colour changes in red wines. J Sci Food Agric 59:299–305

    Article  CAS  Google Scholar 

  • Maçanita AL, Moreira PF, Lima JC, Quina FH, Yihwa C, Vautier-Giongo C (2002) Proton transfer in anthocyanins and related flavylium salts. Determination of ground state constant with nanosecond laser flash photolysis. J Phys Chem A 106:1248–1255

    Article  Google Scholar 

  • Mateus N, Carvalho E, Carvalho A, Melo A, Santos-Buelga C, Silva AMS, De Freitas VAP (2003a) Isolation and Structural Characterization of New Acylated Anthocyanin-Vinyl-Flavanol Pigments Occurring in Aging Red Wines. J Agric Food Chem 51:277–282

    Article  CAS  Google Scholar 

  • Mateus N, De Freitas VAP (2001a) Evolution and stability of anthocyanin-derived pigments in Port wine during ageing. J Agric Food Chem 49:5217–5222

    Article  CAS  Google Scholar 

  • Mateus N, Oliveira J, Santos-Buelga C, Silva AMS, De Freitas VAP (2004) NMR structure characterization of a new vinylpyranoanthocyanin-catechin pigment. Tetrahedron Lett 45:3455–3457

    Article  CAS  Google Scholar 

  • Mateus N, Pascual-Teresa S, Rivas-Gonzalo JC, Santos-Buelga C, De Freitas VAP (2002a) Structural diversity of anthocyanin-derived pigments in Port wines. Food Chem 76:335–342

    Article  CAS  Google Scholar 

  • Mateus N, Silva AMS, Rivas-Gonzalo JC, Santos-Buelga C, De Freitas VAP (2002b) Identification of anthocyanin-flavanol pigments in red wines by NMR and mass spectrometry. J Agric Food Chem 50:2110–2116

    Article  CAS  Google Scholar 

  • Mateus N, Silva AMS, Rivas-Gonzalo JC, Santos-Buelga C, De Freitas VAP (2003b) A new class of blue anthocyanins-derived pigments isolated from red wines. J Agric Food Chem 51:1919–1923

    Article  CAS  Google Scholar 

  • Mateus N, Silva AMS, Vercauteren J, De Freitas VAP (2001b) Occurrence of anthocyanin-derived pigments in red wines. J Agric Food Chem 49:4836–4840

    Article  CAS  Google Scholar 

  • Mazza G, Brouillard R (1987) Recent developments in the stabilization of anthocyanins in food products. Food Chem 25:207–225

    Article  CAS  Google Scholar 

  • Pissarra J, Lourenço S, Gonzalez-Paramas AM, Mateus N, Santos-Buelga C, Silva AMS, De Freitas VAP (2005a) Isolation and structural characterization of new anthocyanin-alkyl-catechin pigments. Food Chem 90:81–87

    Article  CAS  Google Scholar 

  • Pissarra J, Lourenço S, Gonzalez-Paramas AM, Mateus N, Santos-Buelga C, Silva AMS, De Freitas VAP (2004a) Structural characterization of new malvidin-3-gluc-catechin alkyl/aryl-linked pigments. J Agric Food Chem 52:5519–5526

    Article  CAS  Google Scholar 

  • Pissarra J, Lourenço S, Mateus N, Gonzalez-Paramas AM, Santos-Buelga C, de Freitas VAP (2004b) Formation of new anthocyanin-alkyl-flavanol pigments. Anal Chim Acta 513:215–221

    Article  CAS  Google Scholar 

  • Pissarra J, Mateus N, Machado JM, Guimaraens D, de Freitas VAP (2005b) Contribution and importance of wine spirit to the Port wine final quality—Initial approach. J Sci Food Agric 85:1091–1097

    Article  CAS  Google Scholar 

  • Pissarra J, Mateus N, Rivas-Gonzalo J, Santos-Buelga C, De Freitas VAP (2003) Reaction between malvidin 3-glucoside and (+)-catechin in model solutions containing different aldehydes. J Food Sci 68:476–481

    Article  CAS  Google Scholar 

  • Remy S, Fulcrand H, Labarbe B, Cheynier V, Moutounet M (2000) First confirmation in red wine of products resulting from direct anthocyanin-tannin reactions. J Sci Food Agric 80:745–751

    Article  CAS  Google Scholar 

  • Rivas-Gonzalo JC, Bravo-Haro S, Santos-Buelga C (1995) Detection of compounds formed through the reaction of malvidin-3-monoglucoside and catechin in the presence of acetaldehyde. J Agric Food Chem 43:1444–1449

    Article  CAS  Google Scholar 

  • Rogerson FS, De Freitas VAP (2002) Fortification spirit, a contributor to the aroma complexity of Porto. J Food Sci 67:564–569

    Article  Google Scholar 

  • Romero C, Bakker J (2000) Anthocyanin and colour evolution during maturation of four Port wines: effect of pyruvic acid addition. J Sci Food Agric 81:252–260

    Article  Google Scholar 

  • Somers TC (1971) The polymeric nature of wine pigments. Phytochemistry 10:2175–216

    Article  CAS  Google Scholar 

  • Timberlake CF, Bridle P (1976) Interactions between anthocyanins, phenolic compounds and acetaldehyde and their significance in red wines. Am J Enol Vitic 27:97–105

    CAS  Google Scholar 

  • Wildenradt HL, Singleton VL (1974) The production of aldehydes as a result of oxidation of polyphenolic compounds and its relation to wine aging. Am J Enol Vitic 26:25–29

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Victor de Freitas.

Additional information

Selected articles from the XXII International Conference on Polyphenols, Helsinki, Finland, organized by Prof. Kristiina Wähälä

Rights and permissions

Reprints and permissions

About this article

Cite this article

de Freitas, V., Mateus, N. Chemical transformations of anthocyanins yielding a variety of colours (Review). Environ Chem Lett 4, 175–183 (2006). https://doi.org/10.1007/s10311-006-0060-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10311-006-0060-3

Keywords

Navigation