Oxovitisins: A new class of neutral pyranone-anthocyanin derivatives in red wines

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 15, 2010, Pages 8814-8819

  He, Jingren ^a,b   Oliveira, Joana ^a   Silva, Artur M S ^c   Mateus, Nuno ^a   De Freitas, Victor ^a  

^a UNIVERSITY OF PORTO   (Portugal)

^b UNIVERSITY OF ADELAIDE   (Australia)

^c UNIVERSITY OF AVEIRO   (Portugal)

Author keywords

Carboxy pyranoanthocyanin; oxidation; oxovitisins; pyranone anthocyanins; red wine aging; vitisin, NMR

Indexed keywords

CARBOXY-PYRANOANTHOCYANIN; OXOVITISINS; PYRANONE-ANTHOCYANINS; RED WINE; VITISIN, NMR;

CARBOXYLATION; IONIZATION OF LIQUIDS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; RESINS; WINE;

ANTHOCYANINS;

ANTHOCYANIN;

ARTICLE; CHEMISTRY; FOOD HANDLING; OXIDATION REDUCTION REACTION; WINE;

ANTHOCYANINS; FOOD HANDLING; OXIDATION-REDUCTION; WINE;

EID: 77955687811     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf101408q     Document Type: Article

References (36)

1. Jurd, L. Review of polyphenol condensation reactions and their possible occurence in the aging of wines Am. J. Enol. Vitic. 1969, 20, 195-197
2. Timberlake, C. F.; Bridle, P. Interactions between anthocyanins, phenolic compounds, and acetaldehyde and their significance in red wines Am. J. Enol. Vitic. 1976, 27, 97-105
3. Liao, H.; Cai, Y.; Haslam, E. Polyphenols interactions. Anthocyanins: Co-pigmentation and color changes in red wines J. Sci. Food Agric. 1992, 59, 299-305
4. Rivas-Gonzalo, J. C.; Bravo-Haro, S.; Santos-Buelga, C. Detection of compounds formed through the reaction of malvidin 3-monoglucoside and catechin in presence of acetaldehyde J. Agric. Food Chem. 1995, 43, 1444-1449
5. Remy, S.; Fulcrand, H.; Labarbe, B.; Cheynier, V.; Moutounet, M. First confirmation in red wine of products resulting from direct anthocyanin-tannin reactions J. Sci. Food Agric. 2000, 80, 745-751
6. Pissarra, J.; Lourenço, S.; González-Paramás, A. M.; Mateus, N.; Santos-Buelga, C.; Silva, A. M. S.; de Freitas, V. Structural characterization of new malvidin 3-glucoside-catechin aryl/alkyl-linked pigments J. Agric. Food Chem. 2004, 52, 5519-5526
7. Pissarra, J.; Mateus, N.; Rivas-Gonzalo, J. C.; Santos-Buelga, C.; De Freitas, V. Reaction between malvidin 3-glucoside and (+)-catechin in model solutions containing different aldehydes J. Food Sci. 2003, 68, 476-481
8. Brouillard, R.; Dangles, O. Anthocyanin molecular interactions: the first step in the formation of new pigments during wine aging? Food Chem. 1994, 51, 365-371
9. Atanasova, V.; Fulcrand, H.; Cheynier, V.; Moutounet, M. Effect of oxygenation on ployphenol changes occurring in the course of wine-making Anal. Chim. Acta 2002, 458, 15-27
10. Bakker, J.; Timberlake, C. Isolation, identification, and characterization of new color stable anthocyanins occuring in some red wines J. Agric. Food Chem. 1997, 45, 35-43
11. Fulcrand, H.; Benabdeljalil, C.; Rigaud, J.; Cheynier, V.; Moutounet, M. A new class of wine pigments generated by reaction between pyruvic acid and grape anthocyanins Phytochemistry 1998, 47, 1401-1407
12. Mateus, N.; Silva, A. M. S.; Vercauteren, J.; De Freitas, V. A. P. Occurrence of anthocyanin-derived pigments in red wines J. Agric. Food Chem. 2001, 49, 4836-4840
13. He, J.; Santos-Buelga, C.; Silva, A. M. S.; Mateus, N.; de Freitas, V. Isolation and structural characterization of new anthocyanin-derived yellow pigments in aged red wines J. Agric. Food Chem. 2006, 54, 9598-9603
14. Fulcrand, H.; Cameiro dos Santos, P. J.; Sarni-Machado, P.; Cheynier, V.; Moutounet, M. Structure of new anthocyanin derived wine pigment J. Chem. Soc., Perkin Trans. I 1996, 735-739 (Pubitemid 126801231)
15. Asenstorfer, R. E.; Hayasaka, Y.; Jones, G. P. Isolation and structures of oligomeric wine pigments by bisulfite-mediated ion-exchange chromatography J. Agric. Food Chem. 2001, 49, 5957-5963
16. Schwarz, M.; Wabnitz, T. C.; Winterhalter, P. Pathway leading to the formation of anthocyanin-vinylphenol adducts and related pigments in red wines J. Agric. Food Chem. 2003, 51, 3682-3687
17. Mateus, N.; Pascual-Teresa, S.; Rivas-Gonzalo, J. C.; Santos-Buelga, C.; De Freitas, V. Structural diversity of anthocyanin-derived pigments detected in Port Wines Food Chem. 2002, 76, 335-342
18. Mateus, N.; Silva, A. M. S.; Rivas-Gonzalo, J. C.; Santos-Buelga, C.; De Freitas, V. A new class of blue anthocyanin-derived pigments isolated from red wines J. Agric. Food Chem. 2003, 51, 1919-1923
19. Mateus, N.; Oliveira, J.; Santos-Buelga, C.; Silva, A. M. S.; De Freitas, V. NMR structure characterization of a new vinylpyranoanthocyanin-catechin pigment (a portisin) Tetrahedron Lett. 2004, 45, 3455-3457
20. Oliveira, J.; De Freitas, V.; Silva, A. M. S.; Mateus, N. Reaction between hydroxycinnamic acids and anthocyanin-pyruvic acid adducts yielding new portisins J. Agric. Food Chem. 2007, 55, 6349-6356
21. Oliveira., J.; Azevedo, J.; Silva, A. M. S.; Teixeira, N.; Cruz, L.; Mateus, N.; de Freitas, V. Pyranoanthocyanin dimers: a new family of turquoise blue anthocyanin-derived pigments found in Port wine J. Agric. Food Chem. 2010, 58, 5154-5159
22. He, J.; Santos-Buelga, C.; Mateus, N.; de Freitas, V. Isolation and quantification of oligomeric pyranoanthocyanin-flavanol pigments from red wines by combination of column chromatographic techniques J. Chromatogr., A 2006, 1134, 215-225
23. Oliveira, J.; Fernandes, V.; Miranda, C.; Santos-Buelga, C.; Silva, A.; de Freitas, V.; Mateus, N. Color properties of four cyanidin-pyruvic acid adducts J. Agric. Food. Chem. 2006, 54, 6894-6903
24. Bax, A.; Subramanian, S. Sensitivity enhanced two-dimensional heteronuclear shift correlation NMR spectroscopy J. Magn. Reson. 1986, 67, 565-569
25. 13C assignments from sensitivity-enhanced detection of heteronuclear multiple-bond connectivity by 2D multiple quantum NMR J. Am. Chem. Soc. 1986, 108, 2093-2094
26. Cameira dos Santos, P. J.; Brillouet, J. M.; Cheynier, V.; Moutounet, M. Detection and partial characterisation of new anthocyanins derived pigments in wine J. Sci. Food Agric. 1996, 70, 204-208
27. Mateus, N.; Carvalho, E.; Carvalho, A. R. F.; Melo, A.; González-Paramás, A. M.; Santos-Buelga, C.; Silva, A. M. S.; De Freitas, V. Isolation and structural characterization of new acylated anthocyanin-vinyl-flavanol pigments occuring in aging red wines J. Agric. Food Chem. 2003, 51, 277-282
28. Mateus, N.; Silva, A. M. S.; Santos-Buelga, C.; Rivas-Gonzalo, J. C.; De Freitas, V. A. P. Identification of anthocyanin-flavanol pigments in red wines by NMR and mass spectrometry J. Agric. Food Chem. 2002, 50, 2110-2116
29. Hayasaka, Y.; Asenstorfer, R. E. Screening for potential pigments derived from anthocyanins in red wine using nanoelectrospray tandem mass spectrometry J. Agric. Food Chem. 2002, 50, 756-761
30. Baranowski, J. D.; Nagel, C. W. Isolation of l-epicatechin and d-catechin by column chromatography J. Agric. Food Chem. 1981, 29, 63
31. Rakhmankulov, D. L.; Latypova, F. N.; Shmakov, V. S.; Zelenova, L. M.; Ilöyasova, A. I.; Nikitina, V. S.; Orazov, O. É. Polyamide sorbents for partitioning flavonoids possessing vitamin P activity Pharm. Chem. J. 1997, 31, 383-387
32. Timberlake, C. F.; Bridle, P. Anthocyanins. In Developments in Food Colors-I; Walford, J., Ed.; Applied Science Publishers Ltd.: London, 1980; pp 115-149.
33. Oliveira, J.; Mateus, N.; Silva, Artur M. S.; de Freitas, V. Equilibrium forms of vitisin B pigments in an aqueous system studied by NMR and visible spectroscopy J. Phys. Chem. B 2009, 113, 11352-11358
34. Asentorfer, R. E.; Jones, G. P. Charge equilibria and p K values of 5-carboxypyranomalvidin-3-glucoside (vitisin A) by electrophoresis and absorption spectroscopy Tetrahedron 2007, 63, 4788-4792
35. Streitwieser, A., Jr.; Healthcock, C. H. Introduction to Organic Chemistry, 3rd ed.; Macmillan: New York, 1985.
36. Mateus, N.; De Freitas, V. Evolution and stability of anthocyanin-derived pigments during Port wine aging J. Agric. Food Chem. 2001, 49, 5217-5222