Structural features of copigmentation of oenin with different polyphenol copigments

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 28, 2013, Pages 6942-6948

  Teixeira, Natércia ^a   Cruz, Luís ^a   Brás, Natércia F ^a   Mateus, Nuno ^a   Ramos, Maria João ^a   De Freitas, Victor ^a  

^a UNIVERSITY OF PORTO   (Portugal)

Author keywords

copigmentation binding constant; oenin (O) catechin; procyanidin B3; prodelphinidin B3

Indexed keywords

BINDING CONSTANT; CITRATE BUFFER; COMPUTATIONAL STUDIES; OENIN-(O)-CATECHIN; PROCYANIDINS; PRODELPHINIDIN B3; STRUCTURAL DATA; STRUCTURAL FEATURE;

ANTHOCYANINS; IONIC STRENGTH; ORGANIC COMPOUNDS; PHENOLS;

BINDING ENERGY;

ANTHOCYANIN; BIFLAVONOID; CATECHIN; DRUG DERIVATIVE; GALLOCATECHIN; PIGMENT; POLYPHENOL; PROANTHOCYANIDIN; PROCYANIDIN B3;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; PIGMENTATION; THERMODYNAMICS; WINE;

ANTHOCYANINS; BIFLAVONOIDS; CATECHIN; MOLECULAR STRUCTURE; PIGMENTATION; PIGMENTS, BIOLOGICAL; POLYPHENOLS; PROANTHOCYANIDINS; THERMODYNAMICS; WINE;

EID: 84880375401     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf401174b     Document Type: Article

References (50)

1. Brouillard, R.; Delaporte, B. Chemistry of anthocyanin pigments. 2. Kinetic and thermodynamic study of proton-transfer, hydration, and tautomeric reactions of malvidin 3-glucoside J. Am. Chem. Soc. 1977, 99, 8461-8468
2. Asen, S.; Stewart, R. N.; Norris, K. H. Copigmentation of anthocyanins in plant-tissues and its effect on color Phytochemistry 1972, 11, 1139-1144
3. Boulton, R. The copigmentation of anthocyanins and its role in the color of red wine: a critical review Am. J. Enol. Vitic. 2001, 52, 67-87
4. Dangles, O. Anthocyanin complexation and colour expression Analysis 1997, 25, M50-M52
5. Goto, T.; Kondo, T. Structure and molecular stacking of anthocyanins-flower color variation Angew. Chem., Int. Ed. 1991, 30, 17-33
6. Haslam, E. Anthocyanin Copigmentation-Fruit and Floral Pigment; Cambridge Press University: Cambridge, UK, 1998; pp 262-297.
7. Robinson, G. M.; Robinson, R. A survey of anthocyanins. I Biochem. J. 1931, 25, 1687-1705
8. Goto, T. Structure, stability and color variation of natural anthocyanins Prog. Chem. Org. Nat. Prod. 1987, 52, 113-158
9. Goto, T.; Tamura, H.; Kawai, T.; Hoshino, T.; Harada, N.; Kondo, T. Chemistry of metalloanthocyanins Ann. N.Y. Acad. Sci. 1986, 471, 155-173
10. Santos-Buelga, C.; De Freitas, V. Influence of phenolics on wine organoleptic properties. In Wine Chemistry and Biochemistry; Moreno-Arribas, M. V.; Polo, C., Eds.; Springer: Berling, Germany, 2009; pp 529-570.
11. Furtado, P.; Figueiredo, P.; Neves, H. C.; Pina, F. Photochemical and thermal degradation of anthocyanins J. Photochem. Photobiol. A 1993, 78, 113-118
12. Cruz, L.; Brás, N. F.; Teixeira, N.; Mateus, N.; Ramos, M. J.; Dangles, O.; de Freitas, V. Vinylcatechin dimers are much better copigments for anthocyanins then catechin dimer procyanidin B3 J. Agric. Food Chem. 2010, 58, 3159-3166
13. Brouillard, R.; Wigand, M. C.; Dangles, O.; Cheminat, A. pH and solvent effects on the copigmentation reaction of malvin with polyphenols, purine and pyrimidine-derivatives J. Chem. Soc., Perkin Trans. 2 1991, 8, 1235-1241
14. Gómez-Míguez, M.; González-Manzano, S.; Escribano-Bailón, M. T.; Heredia, F. J.; Santos-Buelga, C. Influence of different phenolic copigments on the color of malvidin 3-glucoside J. Agric. Food Chem. 2006, 54, 5422-5429
15. Liao, H.; Cai, Y.; Haslam, E. Polyphenols interactions. Anthocyanins: copigmentation and colour changes in red wines J. Sci. Food Agric. 1992, 59, 299-305
16. Berké, B.; de Freitas, V. A. P. Influence of procyanidin structures on their ability to complex with oenin Food Chem. 2005, 90, 453-460
17. Chen, L. J.; Hrazdina, G. Structural aspects of anthocyanin-flavonoid complex-formation and its role in plant color Phytochemistry 1981, 20, 297-303
18. Asen, S.; Stewart, R. N.; Norris, K. H. Co-pigmentation effect of quercetin glycosides on absorption characateristics of cyanidin glycosides and color of red wing azalea Phytochemistry 1971, 10, 171-175
19. Asen, S.; Stewart, R. N.; Norris, K. H. Copigmentation of aurone and flavone from petals of antirrhinum-majus Phytochemistry 1972, 11, 2739-2741
20. Mazza, G.; Brouillard, R. Polyphenol interations. Part 5 anthocyanin co-pigmentaion J. Chem. Soc., Perkin Trans. 1990, 2, 1287-1296
21. 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
22. Cai, Y.; Lilley, T. H.; Haslam, E. Polyphenol anthocyanin copigmentation J. Chem. Soc., Chem. Commun. 1990, 380-383
23. Dallas, C.; Ricardo-da-Silva, J. M.; Laureano, O. Products formed in model wine solutions involving anthocyanins, procyanidin B-2, and acetaldehyde J. Agric. Food Chem. 1996, 44, 2402-2407
24. Es-Safi, N. E.; Fulcrand, H.; Cheynier, V.; Moutounet, M. Studies on the acetaldehyde-induced condensation of (-)-epicatechin and malvidin 3- O -glucoside in a model solution system J. Agric. Food Chem. 1999, 47, 2096-2102
25. Rivas-Gonzalo, J. C.; Bravo-Haro, S.; Santos-Buelga, C. Detection of compounds formed through the reaction of malvidin-3-monoglucoside and catechin in the presence of acetaldehyde J. Agric. Food Chem. 1995, 43, 1444-1449
26. 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
27. 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
28. Hayasaka, Y.; Kennedy, J. A. Mass spectrometric evidence for the formation of pigmented polymers in red wine Aust. J. Grape Wine Res. 2003, 9, 210-220
29. Jurd, L. Review of polyphenol condensation reactions and their possible ocurrence in aging of wines Am. J. Enol. Vitic. 1969, 20, 195-197
30. 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
31. Somers, T. C. The polymeric nature of wine pigments Phytochemistry 1971, 10, 2175-2186
32. Duenas, M.; Salas, E.; Cheynier, V.; Dangles, O.; Fulcrand, H. UV-visible spectroscopic investigation of the 8,8-methylmethine catechin-malvidin 3-glucoside pigments in aqueous solution: structural transformations and molecular complexation with chlorogenic acid J. Agric. Food Chem. 2006, 54, 189-196
33. Remy-Tanneau, S.; Le Guerneve, C.; Meudec, E.; Cheynier, V. Characterization of a colorless anthocyanin-flavan-3-ol dimer containing both carbon-carbon and ether interflavanoid linkages by NMR and mass spectrometry J. Agric. Food Chem. 2003, 51, 3592-3597
34. Cruz, L.; Mateus, N.; De Freitas, V. Identification by mass spectrometry of new compounds arising from the reactions involving malvidin-3-glucoside-(O)- catechin, catechin and malvidin-3-glucoside Rapid Commun. Mass Spectrom. 2012, 26, 2123-2130
35. Dvorakova, M.; Moreira, M. M.; Dostalek, P.; Skulilova, Z.; Guido, L. F.; Barros, A. A. Characterization of monomeric and oligomeric flavan-3-ols from barley and malt by liquid chromatography-ultraviolet detection-electrospray ionization mass spectrometry J. Chromatogr., A 2008, 1189, 398-405
36. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09; Gaussian, Inc.: Wallingford, CT, 2009.
37. Bayly, C. I.; Cieplak, P.; Cornell, W. D.; Kollman, P. A. A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges-the RESP model J. Phys. Chem. U.S. 1993, 97 (40) 10269-10280
38. Wang, J. M.; Wolf, R. M.; Caldwell, J. W.; Kollman, P. A.; Case, D. A. Development and testing of a general amber force field J. Comput. Chem. 2004, 25 (9) 1157-1174
39. Izaguirre, J. A.; Catarello, D. P.; Wozniak, J. M.; Skeel, R. D. Langevin stabilization of molecular dynamics J. Phys. Chem. U.S. 2001, 114 (5) 2090-2098
40. Case, D. A.; Darden, T. A.; Cheatham, T. E., III; Simmerling, C. L.; Wang, J.; Duke, R. E.; Luo, R.; Crowley, M.; Walker, R. C.; Zhang, W.; Merz, K. M.; Wang, B.; Hayik, S.; Roitberg, A.; Seabra, G.; Kolossváry, I.; Wong, K. F.; Paesani, F.; Vanicek, J.; Wu, X.; Brozell, S. R.; Steinbrecher, T.; Gohlke, H.; Yang, L.; Tan, C.; Mongan, J.; Hornak, V.; Cui, G.; Mathews, D. H.; Seetin, M. G.; Sagui, C.; Babin, V.; Kollman, P. A. AMBER 10; University of California: San Francisco, CA, 2008.
41. Ryckaert, J. P.; Ciccotti, G.; Berendsen, H. J. C. Numerical-integration of Cartesian equations of motion of a system with constraints-molecular-dynamics of n -alkanes J. Comput. Phys. 1977, 23 (3) 327-341
42. Huo, S.; Massova, I.; Kollman, P. A. Computational alanine scanning of the 1:1 human growth hormone-receptor complex J. Comput. Chem. 2002, 23 (1) 15-27
43. Kollman, P. A.; Massova, I.; Reyes, C.; Kuhn, B.; Huo, S. H.; Chong, L.; Lee, M.; Lee, T.; Duan, Y.; Wang, W.; Donini, O.; Cieplak, P.; Srinivasan, J.; Case, D. A.; Cheatham, T. E. Calculating structures and free energies of complex molecules: combining molecular mechanics and continuum models Acc. Chem. Res. 2000, 33 (12) 889-897
44. Massova, I.; Kollman, P. A. Combined molecular mechanical and continuum solvent approach (MM-PBSA/GBSA) to predict ligand binding Perspect. Drug Discov. 2000, 18, 113-135
45. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Merz, K. M.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P A. A 2nd generation force-field for the simulation of proteins, nucleic-acids, and organic-molecules J. Am. Chem. Soc. 1995, 117 (19) 5179-5197
46. Dangles, O.; Brouillard, R. Polyphenol interactions-the copigmentation case-thermodynamic data from temperature-variation and relaxation kinetics-medium effect Can. J. Chem. 1992, 70, 2174-2189
47. Dangles, O.; Elhajji, H. Synthesis of 3-methoxy-flavylium and 3-(β- d -glucopyranosyloxy)flavylium ions-influence of the flavylium substitution pattern on the reactivity of anthocyanins in aqueous-solution Helv. Chim. Acta 1994, 77, 1595-1610
48. Malien-Aubert, C.; Dangles, O.; Amiot, M. J. Influence of procyanidins on the color stability of oenin solutions J. Agric. Food Chem. 2002, 50, 3299-3305
49. Macanita, A. L.; Moreira, P. F.; Lima, J. C.; Quina, F. H.; Yihwa, C.; Vautier-Giongo, C. Proton transfer in anthocyanins and related flavylium salts. Determination of ground-state rate constants with nanosecond laser flash photolysis J. Phys. Chem. A 2002, 106, 1248-1255
50. Meo, F. D.; Garcia, J. C. S.; Dangles, O.; Trouillas, P. Highlights on anthocyanin pigmentation and copigmentation: a matter of flavonoid π-stacking complexation to be described by DFT-D J. Chem. Theory Comput. 2012, 8, 2034-2043-2043