Antioxidant features of red wine pyranoanthocyanins: Experimental and theoretical approaches

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 29, 2014, Pages 7002-7009

  Azevedo, Joana ^a   Oliveira, Joana ^a   Cruz, Luis ^a   Teixeira, Natércia ^a   Brás, Natércia F ^a   De Freitas, Victor ^a   Mateus, Nuno ^a  

^a UNIVERSITY OF PORTO   (Portugal)

Author keywords

antioxidant; DFT; liposome; malvidin 3 glucoside; pyranoanthocyanins; red wine

Indexed keywords

ANTIOXIDANTS; CARBOHYDRATES; FREE RADICALS; LIPOSOMES; WINE; FLAVONOIDS;

ANTIOXIDANT COMPOUNDS; ANTIOXIDANT POTENTIAL; ANTIOXIDANT PROPERTIES; DFT; MALVIDIN-3-GLUCOSIDE; PYRANOANTHOCYANINS; RADICAL SCAVENGING CAPACITIES; RED WINE;

ANTHOCYANINS;

ANTHOCYANIN; ANTIOXIDANT; LIPOSOME; OXYGEN;

ANALYSIS; CHEMISTRY; DRUG EFFECTS; LIPID PEROXIDATION; THEORETICAL MODEL; WINE;

ANTHOCYANINS; ANTIOXIDANTS; LIPID PEROXIDATION; LIPOSOMES; MODELS, THEORETICAL; OXYGEN; WINE;

EID: 84904791617     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf404735j     Document Type: Article

References (50)

1. Rentzsch, M.; Weber, F.; Durner, D.; Fischer, U.; Winterhalter, P. Variation of pyranoanthocyanins in red wines of different varieties and vintages and the impact of pinotin A addition on their color parameters Eur. Food Res. Technol. 2009, 229, 689-696
2. Brouillard, R.; Chassaing, S.; Fougerousse, A. Why are grape/fresh wine anthocyanins so simple and why is it that red wine color lasts so long? Phytochemistry 2003, 64, 1179-1186
3. Bakker, J.; Timberlake, C. F. Isolation, identification, and characterization of new color-stable anthocyanins occurring in some red wines J. Agric. Food Chem. 1997, 45, 35-43
4. 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
5. Mateus, N.; Pascual-Teresa, S. D.; Rivas-Gonzalo, J. C.; Santos-Buelga, C.; de Freitas, V. Structural diversity of anthocyanin-derived pigments in port wines Food Chem. 2002, 76, 335-342
6. 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
7. 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
8. Fulcrand, H.; dos Santos, P.-J. C.; Sarni-Manchado, P.; Cheynier, V.; Favre-Bonvin, J. Structure of new anthocyanin-derived wine pigments J. Chem. Soc., Perkin Trans. 1 1996, 7, 735-739
9. 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
10. Schwarz, M.; Jerz, G.; Winterhalter, P. Isolation and structure of pinotin A, a new anthocyanin derivative from Pinotage wine Vitis 2003, 42, 105-106
11. Cruz, L.; Teixeira, N. R.; Silva, A. M. S.; Mateus, N.; Borges, J.; de Freitas, V. Role of vinylcatechin in the formation of pyranomalvidin-3- glucoside-(+)-catechin J. Agric. Food Chem. 2008, 56, 10980-10987
12. Van Acker, S. A. B. E.; Van Den Berg, D.-j.; Tromp, M. N. J. L.; Griffioen, D. H.; Van Bennekom, W. P.; Van Der Vijgh, W. J. F.; Bast, A. Structural aspects of antioxidant activity of flavonoids Free Radical Biol. Med. 1996, 20, 331-342
13. Tsuda, T.; Shiga, K.; Ohshima, K.; Kawakishi, S.; Osawa, T. Inhibition of lipid peroxidation and the active oxygen radical scavenging effect of anthocyanin pigments isolated from Phaseolus vulgaris L Biochem. Pharmacol. 1996, 52, 1033-1039
14. Garcia-Alonso, M.; Rimbach, G.; Sasai, M.; Nakahara, M.; Matsugo, S.; Uchida, Y.; Rivas-Gonzalo, J. C.; Pascual-Teresa, S. D. Electron spin resonance spectroscopy studies on the free radical scavenging activity of wine anthocyanins and pyranoanthocyanins Mol. Nutr. Food Res. 2005, 49, 1112-1119
15. Kahkonen, M. P.; Heinonen, M. Antioxidant activity of anthocyanins and their aglycons J. Agric. Food Chem. 2003, 51, 628-633
16. Wang, H.; Cao, G.; Prior, R. L. Oxygen radical absorbing capacity of anthocyanins J. Agric. Food Chem. 1997, 45, 304-309
17. Azevedo, J.; Fernandes, I.; Faria, A.; Oliveira, J.; Fernandes, A.; de Freitas, V.; Mateus, N. Antioxidant properties of anthocyanidins, anthocyanidin-3-glucosides and respective portisins Food Chem. 2010, 119, 518-523
18. Fernandes, I.; Faria, A.; Azevedo, J.; Soares, S.; Calhau, C.; De Freitas, V.; Mateus, N. Influence of anthocyanins, derivative pigments and other catechol and pyrogallol-type phenolics on breast cancer cell proliferation J. Agric. Food Chem. 2010, 58, 3785-3792
19. Faria, A.; Oliveira, J.; Neves, P.; Gameiro, P.; Santos-Buelga, C.; de Freitas, V.; Mateus, N. Antioxidant properties of prepared blueberry (Vaccinium myrtillus) extracts J. Agric. Food Chem. 2005, 53, 6896-6902
20. Kong, J. M.; Chia, L. S.; Goh, N. K.; Chia, T. F.; Brouillard, R. Analysis and biological activities of anthocyanins Phytochemistry 2003, 64, 923-933
21. Muselík, J.; García-Alonso, M.; Martín-López, M.; Žemlička, M.; Rivas-Gonzalo, J. Measurement of antioxidant activity of wine catechins, procyanidins, anthocyanins and pyranoanthocyanins Int. J. Mol. Sci. 2007, 8, 797-809
22. Leopoldini, M.; Marino, T.; Russo, N.; Toscano, M. Density functional computations of the energetic and spectroscopic parameters of quercetin and its radicals in the gas phase and in solvent Theor. Chem. Acc. 2004, 111, 210-216
23. Leopoldini, M.; Marino, T.; Russo, N.; Toscano, M. Antioxidant properties of phenolic compounds: H-atom versus electron transfer mechanism J. Phys. Chem. A 2004, 108, 4916-4922
24. Leopoldini, M.; Pitarch, I. P.; Russo, N.; Toscano, M. Structure, conformation, and electronic properties of apigenin, luteolin, and taxifolin antioxidants. A first principle theoretical study J. Phys. Chem. A 2004, 108, 92-96
25. Wright, J. S.; Johnson, E. R.; DiLabio, G. A. Predicting the activity of phenolic antioxidants: theoretical method, analysis of substituent effects, and application to major families of antioxidants J. Am. Chem. Soc. 2001, 123, 1173-1183
26. Alcaro, S.; Chiodo, S. G.; Leopoldini, M.; Ortuso, F. Antioxidant efficiency of oxovitisin, a new class of red wine pyranoanthocyanins, revealed through quantum mechanical investigations J. Chem. Inf. Model. 2013, 53, 66-75
27. Leopoldini, M.; Chiodo, S. G.; Russo, N.; Toscano, M. Detailed investigation of the OH radical quenching by natural antioxidant caffeic acid studied by quantum mechanical models J. Chem. Theory Comput. 2011, 7, 4218-4233
28. Leopoldini, M.; Rondinelli, F.; Russo, N.; Toscano, M. Pyranoanthocyanins: a theoretical investigation on their antioxidant activity J. Agric. Food Chem. 2010, 58, 8862-8871
29. Leopoldini, M.; Russo, N.; Toscano, M. The molecular basis of working mechanism of natural polyphenolic antioxidants Food Chem. 2011, 125, 288-306
30. Oliveira, J.; Santos-Buelga, C.; Silva, A. M. S.; de Freitas, V.; Mateus, N. Chromatic and structural features of blue anthocyanin-derived pigments present in Port wine Anal. Chim. Acta 2006, 563, 2-9
31. Mateus, N.; Silva, A. M. S.; Vercauteren, J.; de Freitas, V. Occurrence of anthocyanin-derived pigments in red wines J. Agric. Food Chem. 2001, 49, 4836-4840
32. He, J. R.; Oliveira, J.; Silva, A. M. S.; Mateus, N.; De Freitas, V. Oxovitisins: a new class of neutral pyranone-anthocyanin derivatives in red wines J. Agric. Food Chem. 2010, 58, 8814-8819
33. Oliveira, J.; de Freitas, V.; Mateus, N. A novel synthetic pathway to vitisin B compounds Tetrahedron Lett. 2009, 50, 3933-3935
34. 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
35. Cruz, L.; Borges, E.; Silva, A. M. S.; Mateus, N.; de Freitas, V. Synthesis of a new (+)-catechin-derived compound: 8-vinylcatechin Lett. Org. Chem. 2008, 5, 530-536
36. Hakansson, A. E.; Pardon, K.; Hayasaka, Y.; de Sa, M.; Herderich, M. Structures and colour properties of new red wine pigments Tetrahedron Lett. 2003, 44, 4887-4891
37. da Silva Porto, P. A.; Laranjinha, J. A.; de Freitas, V. A. Antioxidant protection of low density lipoprotein by procyanidins: structure/activity relationships Biochem. Pharmacol. 2003, 66, 947-954
38. Becke, A. D. Density-functional exchange-energy approximation with correct asymptotic-behavior Phys. Rev. A 1988, 38, 3098-3100
39. Becke, A. D. Density-functional thermochemistry. 4. A new dynamical correlation functional and implications for exact-exchange mixing J. Chem. Phys. 1996, 104, 1040-1046
40. Lee, C. T.; Yang, W. T.; Parr, R. G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron-density Phys. Rev. B 1988, 37, 785-789
41. 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, USA, 2009.
42. Tomasi, J.; Mennucci, B.; Cammi, R. Quantum mechanical continuum solvation models Chem. Rev. 2005, 105, 2999-3093
43. Bondet, V.; Brand-Williams, W.; Berset, C. Kinetics and mechanisms of antioxidant activity using the DPPḢ free radical method Lebensm. Wiss. Technol. 1997, 30, 609-615
44. Bors, W.; Heller, W.;; Michel, C.;; Saran, M. [36] Flavonoids as antioxidants: determination of radical-scavenging efficiencies. In Methods in Enzymology; Lester, P.; Alexander, N. G., Eds.; Academic Press: New York, 1990; pp 343-355.
45. Rice-Evans, C. A.; Miller, N. J.; Paganga, G. Structure-antioxidant activity relationships of flavonoids and phenolic acids Free Radical Biol. Med. 1996, 20, 933-956
46. Goupy, P.; Bautista-Ortin, A. B.; Fulcrand, H.; Dangles, O. Antioxidant activity of wine pigments derived from anthocyanins: hydrogen transfer reactions to the DPPH radical and inhibition of the heme-induced peroxidation of linoleic acid J. Agric. Food Chem. 2009, 57, 5762-5770
47. Esterbauer, H.; Gebicki, J.; Puhl, H.; Jürgens, G. The role of lipid peroxidation and antioxidants in oxidative modification of LDL Free Radical Biol. Med. 1992, 13, 341-390
48. Niki, E.; Saito, T.; Kawakami, A.; Kamiya, Y. Inhibition of oxidation of methyl linoleate in solution by vitamin E and vitamin C J. Biol. Chem. 1984, 259, 4177-4182
49. Estevez, L.; Mosquera, R. A. Conformational and substitution effects on the electron distribution in a series of anthocyanidins J. Phys. Chem. A 2009, 113, 9908-9919
50. Borkowski, T.; Szymusiak, H.; Gliszczynska-Swiglo, A.; Rietjens, I.; Tyrakowska, B. Radical scavenging capacity of wine anthocyanins is strongly pH-dependent J. Agric. Food Chem. 2005, 53, 5526-5534