Relative Contributions of Polyphenolic Constituents to the Antioxidant Status of Wines: Development of a Predictive Model

Journal of Agricultural and Food Chemistry

Volumn 45, Issue 10, 1997, Pages 3995-4003

  Soleas, George J ^a,b   Tomlinson, George ^a   Diamandis, Eleftherios P ^a   Goldberg, David M ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b Liquor Control Board of Ontario   (Canada)

Author keywords

Antioxidants; Caffeic acid; Catechin; Epicatechin; Ferulic acid; Flavonoids; Gallic acid; Gentisic acid; m coumaric acid; Morin; p coumaric acid; Phenolic acids; Polydatin; Quercetin; Resveratrol; Syringic acid; Trihydroxystilbenes; Vanillic acid; Wine

Indexed keywords

EID: 0001364060     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf9702959     Document Type: Article

References (79)

1. Ames, B. N. Endogenous oxidative DNA damage, aging and cancer. Free Radical Res. Commun. 1989, 7, 121-127.
2. Auge, N.; Pierragi, M. T.; Thiers, J. C.; Negre-Salvayre, A.; Salvayre, R. Proliferative and cytotoxic effects of mildly oxidized low-density lipoproteins on vascular smooth muscle cells. Biochem. J. 1995, 309, 1015-1020.
3. Berliner, J. A.; Schwartz, D. S.; Terrino, M. C.; Andalibi, A.; Almada, L.; Lusis, A. J.; Quismorio, D.; Fangz, P.; Fogelman, A. M. Induction of chemotactic cytokines by minimally oxidized LDL. Adv. Exp. Med. Biol. 1993, 351, 13-18.
4. Chen, C.-W.; Ho, C.-T. Antioxidant properties of polyphenols extracted from green and black teas. J. Food Lipids 1995, 2, 35-46.
5. Craig, W. Y. Autoantibodies against oxidized low density lipoprotein: a review of clinical findings and assay methodology. J. Clin. Lab. Anal. 1995, 9, 70-74.
6. Criqui, M. H. Alcohol and coronary heart disease: consistent relationship and public health implications. Clin. Chim. Acta 1996, 246, 51-57.
7. Criqui, M. H.; Ringel, B. L. Does diet or alcohol explain the French paradox? Lancet 1994, 344, 1719-1723.
8. Da Silva, J. M. R.; Darmon, N.; Fernandez, Y.; Mitjavila, S. Oxygen free radical scavenger capacity in aqueous models of different procyanidins from grape seeds. J. Agric. Food Chem. 1991, 39, 1549-1552
9. De Whalley, C. V.; Rankin, S. M; Hoult, J. R. S.; Jessup, W.; Leakes, D. S. Flavonoids inhibit the oxidative modification of low-density lipoproteins by macrophages. Biochem. Pharmacol. 1990, 39, 1743-1745.
10. Elford, H. L.; Van't Riet, B. Phenols and polyphenols as antioxidants and anticancer agents. Dev. Oncol. 1991, 67, 201-204.
11. Esterbauer, H.; Gebicki, J.; Puhl, H.; Jurgens, G. The role of lipid peroxidation and antioxidants in oxidative modification of LDL. Free Radical Biol. Med. 1992, 13, 341-390.
12. Frankel, E. N.; Kanner, J.; German, J. B.; Parks, E.; Kinsella, J. E. Inhibition of oxidation of human low-density lipoprotein by phenolic substances in red wine. Lancet 1993a, 341, 454-457.
13. Frankel, E. N.; Waterhouse, A. L.; Kinsella, J. E. Inhibition of human LDL oxidation by resveratrol. Lancet 1993b, 341, 1103-1104.
14. Frankel, E. N.; Waterhouse, A. L.; Teissedre, P. L. Principal phenolic phytochemicals in selected California wines and their antioxidant activity in inhibiting oxidation of human low-density lipoproteins. J. Agric. Food Chem. 1995, 43, 890-894.
15. Fritzemeier, K. H.; Kindl, H. Coordinate induction by ultraviolet light of stilbene synthase, phenylalanine ammonia lyase and cinnamate-4-hydroxylase in leaves of Vitaceae. Planta 1981, 151, 48-52.
16. Gaziano, J. M.; Buring, J. E.; Breslow, J. L.; Goldhabei, S. Z.; Rosner, B.; Van Denburgh, M.; Willett, W.; Hennekens, C. H. Moderate alcohol intake, increased levels of high-density lipoprotein and its subfractions and decreased risk of myocardial infarction. N. Engl. J. Med. 1993, 329, 1829-1834.
17. Goldberg, D. M.; Karumanchiri, A.; Ng, E.; Yan, J.; Diamandis, E. P.; Soleas, G. J. Direct gas chromatographic-mass spectrometric method to assay cis-resveratrol in wines: preliminary survey of its concentration in commercial wines. J. Agric. Food Chem. 1995a, 43, 1245-1250.
18. Goldberg, D. M.; Ng, E.; Karumanchiri, A.; Yan, J.; Diamandis, E. P.; Soleas, G. J. Assay of resveratrol glucosides and isomers in wine by direct-injection high-performance liquid chromatography. J. Chromatogr. A 1995b, 708, 89-98.
19. Goldberg, D. M.; Tsang, E.; Karumanchiri, A.; Diamandis, E. P.; Soleas, G. J.; Ng, E. A method to assay the concentrations of phenolic constituents of biological interest in wines. Anal. Chem. 1996, 68, 1688-1694.
20. Grisham, M. B. Oxidants and free radicals in inflammatory bowel disease. Lancet 1994, 344, 859-863.
21. Gronbaek, M.; Deis, A.; Sorensen, T. I. A.; Becker, U.; Borch-Johnsen, K.; Muller, C.; Schnohr, P.; Jensen, G. Influence of sex, age, body mass index, and smoking on alcohol intake and mortality. Br. Med. J. 1994, 308, 302-306.
22. Halliwell, B. Free radicals, antioxidants, and human disease: curiosity, cause, or consequence? Lancet 1994, 344, 721-724.
23. Hastie, T. J.; Tibshirani, R. J. Generalized additive models; Chapman and Hall: London, U.K., 1990.
24. Hegsted, D. M.; Ausman, L. M. Diet, alcohol and coronary heart disease in men. J. Nutr. 1988, 118, 1184-1189.
25. Hertog, M. G.; Hollman, P. C. H.; Katan, M. Content of potentially anticarcinogenic flavonoids of 28 vegetables and of 9 fruits commonly consumed in the Netherlands J. Agric. Food Chem. 1992, 40, 2379-2383.
26. Hertog, M. G. L.; Feakone, E. J. M.; Holleman, P. C. H.; Katan, J. B.; Kromhout, D. Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen elderly study. Lancet 1993, 342, 1007-1011.
27. Ho, C.-T.; Lee, C. Y.; Huang, M.-T. In Phenolic compounds in food and their effects on health; Ho, C.-T., Lee, C. Y., Huang, M.-T., Eds.; ACS Symposium Series 506; American Chemical Society: Washington, DC, 1991; Vols. I and II, pp 2-7.
28. Hrazdina, G.; Parsons, G. F.; Mattick, L. R. Physiological and biochemical events during development and maturation of grape berries. Am. J. Enol. Vitic. 1984, 35, 220-227.
29. Hubbard, R. W.; Mejia, A.; Horning, M. The potential of diet to alter disease processess. Nutr. Res. 1994, 14, 1853-1895.
30. Jeandet, P.; Bessis, R.; Maume, B. F.; Meunier, P.; Peyron, D.; Trollat, P. Effect of enological practices on the resveratrol isomer content of wine. J. Agric. Food Chem. 1995a, 43, 316-319.
31. Jeandet, P.; Bessis, R.; Sbaghi, M.; Meunier, P.; Trollat, P. Resveratrol content of wines of different ages: relationship with fungal disease pressure in the vineyard. Am. J. Enol. Vitic. 1995b, 46, 1-4.
32. Jijon, H. B.; Parsons, H. B. Mitogen activated protein kinase is required for tumor necrosis factor α-stimulated interleukin 8 secretion in a human colonic cell line. J. Clin. Invest. 1997, submitted.
33. Kannel, W. B.; Ellison, R. C. Alcohol and coronary heart disease: the evidence for a protective effect. Clin. Chim. Acta 1996, 246, 5976.
34. Kanner, J.; Frankel, E.; Granit, R.; German, B.; Kinsella, J. E. Natural antioxidants in grapes and wines. J. Agric. Food Chem. 1994, 42, 64-69.
35. Kiener, P. A.; Rankin, B. M.; Davis, P. M.; Yocum, S. A.; Warr, G. A.; Grove, R. I. Immune complexes of LDL induced atherogenic responses in human monocytic cells. Arterioscler., Thromb., Vasc. Biol. 1995, 15, 990-999.
36. Klatsky, A. L.; Armstrong, M. A.; Friedman, G. D. Alcohol and mortality. Ann. Intern. Med. 1992, 117, 646-654.
37. Klatsky, A. L.; Armstrong, M. A. Alcoholic beverage choice and risk of coronary artery disease mortality: Do red wine drinkers fare best? Am. J. Cardiol. 1993, 71, 467-469.
38. Kovac, V.; Alonso, E.; Revilla, E. The effect of adding supplementary quantities of seeds during fermentation on the phenolic composition of wines. Am. J. Enol. Vitic. 1995, 46, 363-367.
39. Kreuzaler, F.; Hahlbrock, K. Enzymic synthesis of an aromatic ring from acetate units. Partial purification and some properties of flavanone synthase of cell-suspension cultures of Petroselinum hortense. Eur. J. Biochem. 1975, 56, 205-213.
40. Lamuela-Raventos, R. M.; Waterhouse, A. L. A direct HPLC separation of wine phenolics. Am. J. Enol. Vitic. 1994, 45, 1-5.
41. Maclure, M. Demonstration of deductive meta-analysis: ethanol intake and risk of myocardial infarction. Epidemiol. Rev. 1993, 15, 328-351.
42. Mangiapane, H.; Thomson, J.; Salter, A.; Brown, S.; Bell, G. D.; White, D. A. The inhibition of the oxidation of low density lipoprotein by ( + )-catechin, a naturally occurring flavonoid. Biochem. Pharmacol. 1992, 43, 445-450.
43. Mattivi, F.; Nicolini, G.; Monetti, A. Spectrophotometric analysis of polyphenols, tool to characterize mono-variety red wines and orientate the wine making process. In 4th International Symposium: Innovations In Wine Technology; Killesberg, Stuttgart, Germany. 1995; pp 184-193.
44. McKenzie, S. J.; Baker, M. S.; Buffinton, G. D.; Doe, W. F. Evidence of oxidant-induced injury to epithelial cells during inflammatory bowel disease. J. Clin. Invest. 1996, 98, 136-141.
45. Mehra, M. R.; Lavie, C. J.; Ventura, H. O.; Milani, R. V. Prevention of atherosclerosis: the potential role of antioxidants. Postgrad. Med. 1995, 98, 175-184.
46. Melchior, F.; Kindl, H. Coordinate and elicitor-dependent expression of stilbene synthase and phenylalanine ammonia-lyase genes in Vitis cv. Optima. Arch. Biochem. Biophys. 1991, 258, 552-557.
47. Namiki, M. Antioxidants/antimutagens in foods. Crit. Rev. Food Sci. Nutr. 1990, 29, 273-300.
48. Nanji, A. A.; French, S. W. Alcoholic beverages and coronary heart disease. Atherosclerosis 1986, 60, 197-198.
49. Packer, L. Interactions among antioxidants in health and disease: Vitamin E and its redox cycle. Proc. Soc. Exp. Biol. Med. 1992, 200, 271-276.
50. Pikaar, N. A.; Wedel, M.; van der Beek, E. J.; van Dokkum, W.; Kempen, H. J.; Kluft, C.; Ockhuizen, T.; Hermus, R. J. Effects of moderate alcohol consumption on platelet aggregation, fibrinolysis, and blood lipids. Metabolism 1987, 36, 538-543.
51. Price, S. F.; Breen, P. J.; Valladao, M.; Watson, B. T. Cluster sun exposure and quercetin in Pinot Noir grapes and wine. Am. J. Enol. Vitic. 1995, 46, 187-194.
52. Renaud, S. C.; Ruf, J.-C. Effects of alcohol on platelet functions. Clin. Chim. Acta 1996, 246, 77-89.
53. Renaud, S. C.; Beswick, A. D.; Fehily, A. M.; Sharp, D. S.; Elwood, P. C. Alcohol and platelet aggregation: the Caerphilly prospective heart disease study. Am. J. Clin. Nutr. 1992, 55, 1012-1017.
54. Rice-Evans, C. Plant polyphenols: free radical scavengers or chain-breaking antioxidants? Biochem. Soc. Symp. 1995, 61, 103-116.
55. Rice-Evans, C. A.; Miller, N. J.; Bolwell, P. G.; Bramley, P. M.; Pridham, J. B. The relative antioxidant activities of plant-derived polyphenolic flavonoids. Free Radical Res. 1995, 22, 375-383.
56. Ridker, P. M.; Vaugham, D. E.; Stampfer, M. J.; Glynn, R. J.; Hennekens, C. H. Association of moderate alcohol consumption and plasma concentration of endogenous tissue-type plasminogen activator. JAMA, J. Am. Med. Assoc. 1994, 272, 929-933.
57. Rimm, E. B.; Giovannucci, E. L.; Willett, W. C.; Colditz, G. A.; Ascherio, A.; Rosner, B.; Stampfer, M. J. Prospective study of alcohol consumption and risk of coronary disease in men. Lancet 1991, 338, 464-468.
58. Rimm, E. B.; Klatsky, A.; Grobbee, D.; Stampfer, M. J. Review of moderate alcohol consumption and reduced risk of coronary heart disease: is the effect due to beer, wine, or spirits? Br. Med. J. 1996, 312, 731-736.
59. Roggero, J.-P.; Coen, S.; Archier, P. Wine phenolics: Optimization of HPLC analysis. J. Liq. Chromatogr. 1990, 13, 2593-2603.
60. Rosenberg, L.; Slone, D.; Shapiro, S.; Kaufman, D. W.; Miettinen, O. S.; Stolley, P. D. Alcoholic beverages and myocardial infarction in young women. Am. J. Public Health 1981, 71, 82-85.
61. Rubin, R.; Rand, M. L. Alcohol and platelet function. Alcohol Clin. Exp. Res. 1994, 18, 105-110.
62. Salah, N.; Miller, N. J.; Paganga, G.; Bolwell, G. P.; Rice-Evans, C. Polyphenolic flavonols as scavengers of aqueous phase radicals and as chain-breaking antioxidants. Arch. Biochem. Biophys. 1995, 322, 339-346.
63. Schofield, D.; Braganza, J. M. Shortcomings of an automated assay for total antioxidant status in biological fluids. Clin. Chem. 1996, 42, 1712-1714.
64. Sen, A.; Srivastava, M. Regression analysis: Theory, methods and applications. Springer-Verlag: New York, 1990.
65. Singleton, V. L.; Trousdale, E. White wine phenolics: Varietal and processing differences as shown by HPLC. Am. J. Enol. Vitic. 1983, 34, 27-34.
66. Soleas, G. J.; Diamandis, E. P.; Goldberg, D. M. Wine as a biological fluid: history, production, and role in disease prevention. J. Clin. Lab. Anal. 1997, 11, 287-313.
67. Soleas, G. J.; Goldberg, D. M.; Karumanchiri, A.; Diamandis, E. P.; Ng, E. Influences of viticultural and oenological factors on changes in cis- and trans-resveratrol in commercial wines. J. Wine Res. 1995, 2, 107-121.
68. Soleas, G. J.; Diamandis, E. P.; Karumanchiri, A.; Goldberg, D. M. A multiresidue derivatization gas-chromatographic assay for fifteen phenolic constituents with mass selective detector. Anal. Chem. 1997a, in press.
69. Soleas, G. J.; Goldberg, D. M.; Diamandis, E. P. Toward the fingerprinting of wines: Cultivar-related patterns of polyphenolic constituents in Ontario wines. J. Agric. Food Chem. 1997b, 45, 3871-3880.
70. Stampfer, M. J.; Rimm, E. B. Epidemiologic evidence for Vitamin E in prevention of cardiovascular disease. Am. J. Clin. Nutr. 1995, 62, 1365S-1369S.
71. Steinberg, D.; Parsatharathy, S.; Carew, T. E.; Khoo, J. C.; Witztum, J. L. Beyond cholesterol. Modifications of low-density lipoprotein that increase its atherogenicity. N. Engl. J. Med. 1989, 320, 915-924.
72. St. Leger, A. S.; Cochrane, A. L.; Moore, F. Factors associated with cardiac mortality in developed countries with particular reference to the consumption of wine. Lancet 1979, 1, 1017-1020.
73. Suh, L; Sheten, J.; Cutler, J. A.; Juller, L. H. Alcohol use and mortality from coronary heart disease: the role of high-density lipoprotein cholesterol. Ann. Intern. Med. 1992, 116, 881-887.
74. Teissedre, P. L.; Frankel, E. N.; Waterhouse, A. L.; Peleg, H.; German, J. B. Inhibition of in vitro human LDL oxidation by phenolic antioxidants from grapes and wines. J. Sci. Food Agric. 1996, 70, 55-61.
75. Thorin, E.; Hamilton, C. A.; Dominiczak, M. H.; Reid, J. L. Chronic exposure of cultured bovine endothelial cells to oxidized LDL abolishes prostacyclin release. Arterioscler. Thromb. 1994, 14, 453-459.
76. Tillement, J. P.; Hostettmann, K.; Testa, B. Electrochemical behavior and antioxidant activity of some natural polyphenols. Helv. Chim. Acta 1996, 79, 1147-1158.
77. Vinson, J. A.; Hontz, B. A. Phenol antioxidant index: comparative antioxidant effectiveness of red and white wines. J. Agric. Food Chem. 1995, 43, 401-403.
78. Vinson, J. A.; Jang, J.; Dabbagh, Y. A.; Serry, M. M.; Cai, S. Plant polyphenols exhibit lipoprotein-bound antioxidant activity using an in vitro oxidation model for heart disease. J. Agric. Food Chem. 1995, 43, 2798-2799.
79. Willet, W. C. Diet and health-what should we eat? Science 1994, 264, 532-537.