Structural and chromatic characterization of a new Malvidin 3-glucoside-vanillyl-catechin pigment

Food Chemistry

Volumn 102, Issue 4, 2007, Pages 1344-1351

  Sousa, Carlos ^a   Mateus, Nuno ^a   Silva, Artur M S ^b   González Paramás, Ana M ^c   Santos Buelga, Celestino ^c   Freitas, Victor de ^a  

^a UNIVERSITY OF PORTO   (Portugal)

^b UNIVERSITY OF AVEIRO   (Portugal)

^c UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

Anthocyanin; Catechin; Colour; Oenin; Vanillin; Wine

Indexed keywords

ANTHOCYANIN; CATECHIN; MALVIDIN CHLORIDE GLUCOSIDE; PIGMENT; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; VANILLIN;

ANALYTIC METHOD; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; COLOR; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTRAL SENSITIVITY; STRUCTURE ANALYSIS; ULTRAVIOLET SPECTROSCOPY;

EID: 33846647502     PISSN: 03088146     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.foodchem.2006.04.050     Document Type: Article

References (32)

1. a of malvidin-3-glucoside by electrophoresis. Analytical Biochemistry 318 (2003) 219-299
2. Atanasova V., Fulcrand H., Cheynier V., and Moutounet M. Effect of oxygenation on polyphenol changes occurring in the course of wine-making. Analytica Chimica Acta 458 (2002) 15-27
3. Bakker J., Picinelli A., and Bridle P. Model wine solutions: colour and composition changes during ageing. Vitis 32 (1993) 111-118
4. Bax A., and Subramanian S. Sensitivity enhanced two-dimensional heteronuclear shift correlation NMR spectroscopy. Journal of Magnetic Resonance 67 (1986) 565-569
5. Bax A., and Summers M.F. H and C assignments from sensitivity-enhanced detection of heteronuclear multiple-bond connectivity by 2D multiple quantum NMR. Journal of the American Chemical Society 108 (1986) 2093-2094
6. Bendz G., Martensson O., and Nilsson E. Studies of flavilium compounds. I. Some flavilium compounds and their properties. Arkiv fur Kemi 27 (1967) 67-77
7. Brouillard R., and Delaporte B. Chemistry of anthocyanin pigments. 2. Kinetics and thermodynamic study of proton transfer, hydration, and tautomeric reactions of malvidin 3-glucoside. Journal of the American Chemical Society 99 (1977) 8461-8468
8. Chatonnet, P. (1991). Incidences du bois de chêne sur la composition chimique et les qualités organoleptiques des vins: applications technologiques. Thesis, Université de Bordeaux II, U.F.R. Institut d'Oenologie.
9. Chatonnet P., Boidron J.N., and Pons M. Effect of heat on oak wood and its chemical composition. Part 2. Variations of certain compounds in relation to toasting intensity. Connaissance de la Vigne et du Vin 23 (1989) 223-250
10. Dallas C., Ricardo da Silva J.M., and Laureano O. Products formed in model wine solutions involving anthocyanins, procyanidin B2 and acetaldehyde. Journal of Agricultural and Food Chemistry 44 (1996) 2402-2407
11. Dallas C., Ricardo da Silva J.M., and Laureano O. Interactions of oligomeric procyanidins in model wine solutions containing malvidin 3-glucoside and acetaldehyde. Journal of the Science of Food and Agriculture 70 (1996) 493-500
12. Escalona H., Birkmyre L., Piggott J.R., and Paterson A. Effect of maturation in small oak casks on the volatility of red wine aroma compounds. Analytica Chimica Acta 458 (2002) 45-54
13. Escribano-Bailón T., Alvarez-Garcia M., Rivas-Gonzalo J.C., Heredia F.J., and Santos-Buelga C. 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 (2001) 1213-1217
14. Escribano-Bailón T., Dangles O., and Brouillard R. Coupling reactions between flavylium ions and catechin. Phytochemistry 41 (1996) 1583-1592
15. Fletcher A.C., Porter L.J., Haslam E., and Gupta R.K. Plant proanthocyanidins. Part 3. Conformational and configurational studies of natural procyanidins. Journal of Chemical Society, Perkin Transactions 1 (1977) 1628-1637
16. Fulcrand H., Doco T., Es-Safi N.E., Cheynier V., and Moutounet M. Study of the acetaldehyde induced polymerisation of flavan-3-ols by liquid chromatography-ion spray mass spectrometry. Journal of Chromatography A 752 (1996) 85-91
17. Hurd R.E. Gradient-enhanced spectroscopy. Journal of Magnetic Resonance 87 (1990) 422-428
18. Jurd L. Review of polyphenol condensation reactions and their possible occurrence in the ageing of wines. American Journal of Enology and Viticulture 20 (1969) 191-195
19. Kay L.E., Keifer P., and Saarinen T. Pure absorption gradient enhanced heteronuclear single quantum correlation spectroscopy with improved sensitivity. Journal of the American Chemical Society 114 (1992) 10663-10665
20. Mateus N., and de Freitas V.A.P. Evolution and stability of anthocyanin-derived pigments in Port wine during ageing. Journal of Agricultural and Food Chemistry 49 (2001) 5217-5222
21. Mateus N., Pascual-Teresa S., Rivas-Gonzalo J.C., Santos-Buelga C., and de Freitas V. Structural diversity of anthocyanin-derived pigments detected in Port wines. Food Chemistry 76 (2002) 335-342
22. Miller D.P., Howell G.S., Michaelis C.S., and Dickmann D.I. The contents of phenolic acid and aldehyde flavor components of white oak as affected by site and species. American Journal of Enology and Viticulture 43 (1992) 333-338
23. Pissarra J., Lourenço S., González-Paramás A.M., Mateus N., Santos Buelga C., Silva A.M.S., et al. Structural characterization of new malvidin 3-glucoside-catechin aryl/alkyl-linked pigments. Journal of Agricultural and Food Chemistry 52 (2004) 5519-5526
24. Pissarra J., Mateus N., Rivas-Gonzalo J.C., Santos-Buelga C., and de Freitas V. Reaction between malvidin 3-glucoside and (+)-catechin in model solutions containing different aldehydes. Journal of Food Science 68 2 (2003) 476-481
25. Revilla I., Perez-Magariño S., Gonzalez-San Jose M.L., and Beltran S. Identification of anthocyanin derivatives in grape skin extracts and red wines by liquid chromatography with diode array and mass spectrometry detection. Journal of Chromatography A 847 (1999) 83-90
26. Rivas-Gonzalo J.C., Bravo-Haro S., and Santos-Buelga C. Detection of compounds formed through the reaction of malvidin-3-monoglucoside and catechin in the presence of acetaldehyde. Journal of Agricultural and Food Chemistry 43 (1995) 1444-1449
27. Sefton M.A., Francis I.L., Pocock P.J., and Williams P.J. The influence of natural seasoning on the concentrations of eugenol, vanillin, and cis- and trans-b-methyl-g-octalactone extracted from French and American oakwood. Sciences des Aliments 13 (1993) 629-643
28. Somers T.C. The polymeric nature of wine pigments. Phytochemistry 10 (1971) 2175-2216
29. Vivar-Quintana A.M., Santos-Buelga C., Francia-Aricha E., and Rivas-Gonzalo J.C. Formation of anthocyanin-derived pigments in experimental red wines. Food Science and Technology International 5 4 (1999) 347-352
30. Vivas N., and Glories Y. Étude de la flore fongique du chêne (Quercus sp.) caractéristique du séchage naturel des bois destinés à la tonnellerie. Cryptogamie-Mycologie 14 (1993) 127-148
31. Vivas N., Glories Y., Doneche B., and Gueho E. Observations sur la flore fongique du bois de chêne (Quercus sp.) au cours de son séchage naturel. Annales des Sciences Naturelles. (Botanique et Biologie vegetale) 13 11 (1991) 149-153
32. Wagner R., and Berger S. Gradient-selected NOESY-A fourfold reduction of the measurement time for the NOESY experiment. Journal of Magnetic Resonance 123A (1996) 119-121