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Synlett 2017; 28(08): 898-906
DOI: 10.1055/s-0036-1589937
DOI: 10.1055/s-0036-1589937
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Wine-Inspired Chemistry: Anthocyanin Transformations for a Portfolio of Natural Colors
Further Information
Publication History
Received: 25 October 2016
Accepted after revision: 05 December 2016
Publication Date:
05 January 2017 (online)
Abstract
During wine aging and maturation, anthocyanins can react with flavanols (directly or mediated by aldehydes) and with small molecules derived from yeast metabolism during fermentation. It has been demonstrated that A-type vitisins (the main pyranoanthocyanins found in red wines) can react with other wine components yielding pyranoanthocyanin pigments with different colors ranging from yellow to turquoise blue. Wine-color chemistry has been an inspiration for the synthesis of new molecules with unique chromatic features.
1 Introduction
2 Formation of Anthocyanin Derivatives
3 Conclusion and Outlook
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References
- 1 Brouillard R, Lang J. Can. J. Chem. 1990; 68: 755
- 2 Liao H, Cai Y, Haslam EJ. Sci. Food Agric. 1992; 59: 299
- 3 Brouillard R, Dangles O. Food Chem. 1994; 51: 365
- 4 Mateus N, de Freitas V. J. Agric. Food Chem. 2001; 49: 5217
- 5 Berké B, Chèze C, Deffieux G, Vercauteren J In Plant Polyphenols 2 . Gross G, Hemingway R, Yoshida T, Branham S. Springer; New York: 2000: 779-790
- 6 Oliveira J, de Freitas V, Mateus N. Tetrahedron Lett. 2009; 50: 3933
- 7 He J, Santos-Buelga C, Silva AM. S, Mateus N, de Freitas V. J. Agric. Food Chem. 2006; 54: 9598
- 8 Sousa A, Mateus N, Soares Silva AM, Vivas N, Nonier M.-F, Pianet I, de Freitas V. J. Agric. Food Chem. 2010; 58: 5664
- 9 He J, Oliveira J, Silva AM. S, Mateus N, de Freitas V. J. Agric. Food Chem. 2010; 58: 8814
- 10 Bakker J, Timberlake CF. J. Agric. Food Chem. 1997; 45: 35
- 11 Fulcrand H, dos Santos P.-JC, Sarni-Manchado P, Cheynier V, Favre-Bonvin J. J. Chem. Soc., Perkin Trans. 1 1996; 735
- 12 Gomez-Alonso S, Blanco-Vega D, Victoria Gomez M, Hermosin-Gutierrez I. J. Agric. Food Chem. 2012; 60: 12210
- 13 Schwarz M, Jerz G, Winterhalter P. Vitis 2003; 42: 105
- 14 Schwarz M, Wabnitz TC, Winterhalter P. J. Agric. Food Chem. 2003; 51: 3682
- 15 Mateus N, Silva AM. S, Rivas-Gonzalo JC, Santos-Buelga C, de Freitas V. J. Agric. Food Chem. 2003; 51: 1919
- 16 Oliveira J, de Freitas V, Silva AM. S, Mateus N. J. Agric. Food Chem. 2007; 55: 6349
- 17 Oliveira J, Azevedo J, Silva AM. S, Teixeira N, Cruz L, Mateus N, de Freitas V. J. Agric. Food Chem. 2010; 58: 5154
- 18 Oliveira J, Mateus N, de Freitas V. Dyes Pigments 2014; 100: 190
- 19 Rivas-Gonzalo JC, Bravo-Haro S, Santos-Buelga C. J. Agric. Food Chem. 1995; 43: 1444
- 20 Francia-Aricha EM, Guerra MT, Rivas-Gonzalo JC, Santos-Buelga C. J. Agric. Food Chem. 1997; 45: 2262
- 21 Es-Safi NE, Fulcrand H, Cheynier V, Moutounet M. J. Agric. Food Chem. 1999; 47: 2096
- 22 Santos-Buelga C, Francia-Aricha EM, de Pascual-Teresa S, Rivas-Gonzalo JC. Eur. Food Res. Technol. 1999; 209: 411
- 23 Escribano-Bailon T, Alvarez-Garcia M, Rivas-Gonzalo JC, Heredia FJ, Santos-Buelga C. J. Agric. Food Chem. 2001; 49: 1213
- 24 Remy-Tanneau S, Le Guerneve C, Meudec E, Cheynier V. J. Agric. Food Chem. 2003; 51: 3592
- 25 Salas E, Fulcrand H, Meudec E, Cheynier V. J. Agric. Food Chem. 2003; 51: 7951
- 26 Pissarra J, Mateus N, Rivas-Gonzalo J, Buelga CS, de Freitas V. J. Food Sci. 2003; 68: 476
- 27 Pissarra J, Lourenco S, Gonzalez-Paramas AM, Mateus N, Santos-Buelga C, de Freitas V. Anal. Chim. Acta 2004; 513: 215
- 28 Somers TC. Phytochemistry 1971; 10: 2175
- 29 Jurd L. Am. J. Enol. Vitic. 1969; 20: 191
- 30 Remy S, Fulcrand H, Labarbe B, Cheynier V, Moutounet M. J. Sci. Food Agric. 2000; 80: 745
- 31 Pissarra JI, Lourenço S, Machado JM, Mateus N, Guimaraens D, de Freitas V. J. Sci. Food Agric. 2005; 85: 1091
- 32 Pissarra J, Lourenço S, Gonzalez-Paramas AM, Mateus N, Santos Buelga CS, Silva AM. S, de Freitas V. J. Agric. Food Chem. 2004; 52: 5519
- 33 Schwarz M, Winterhalter P. Tetrahedron Lett. 2003; 44: 7583
- 34 Oliveira J, Mateus N, Silva AM. S, de Freitas V. J. Phys. Chem. B 2009; 113: 11352
- 35 Oliveira J, Petrov V, Parola AJ, Pina F, Azevedo J, Teixeira N, Bras NF, Fernandes PA, Mateus N, Ramos MJ, de Freitas V. J. Phys. Chem. B 2011; 115: 1538
- 36 Oliveira J, Mateus N, de Freitas V. Tetrahedron Lett. 2013; 54: 5106
- 37 Cruz L, Petrov V, Teixeira N, Mateus N, Pina F, de Freitas V. J. Phys. Chem. B 2010; 114: 13232
- 38 Carvalho AR. F, Oliveira J, de Freitas V, Mateus N, Melo A. THEOCHEM-J. Mol. Struct. 2010; 948: 61
- 39 de Freitas V, Mateus N. Anal. Bioanal. Chem. 2011; 401: 1463
- 40 Mateus N, Oliveira J, Santos-Buelga C, Silva AM. S, de Freitas V. Tetrahedron Lett. 2004; 45: 3455
- 41 Chassaing S, Isorez G, Kueny-Stotz M, Brouillard R. Tetrahedron Lett. 2008; 49: 6999
- 42 Oliveira J, Mateus N, de Freitas V. Tetrahedron Lett. 2011; 52: 1996
- 43 Oliveira J, Fernandes A, de Freitas V. Tetrahedron Lett. 2016; 57: 1277
- 44 Oliveira J, Araujo P, Fernandes A, Mateus N, de Freitas V. Synlett 2016; 27: 2459