Wine as a biological fluid: History, production, and role in disease prevention

Journal of Clinical Laboratory Analysis

Volumn 11, Issue 5, 1997, Pages 287-313

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

^a UNIVERSITY OF TORONTO   (Canada)

^b Andres Wines   (Canada)

Author keywords

Anticarcinogenic agents; Antioxidants; Biological oxidation; Caffeic acid; Catechin; Cholesterol; Cinnamic acid; Cyclo oxygenase inhibitors; Eicosanoids; Epicatechin; Ferulic acid; Flavonoids; Gentisic acid; Leukotrienes; Low density lipoprotein; Nitric oxide; P coumaric acid; Phenolic acids; Platelet aggregation; Polyphenols; Quercetin; Resveratrol and polydatin; Stilbenes; Thromboxane; Vanlillic acid; Xanithine oxidase

Indexed keywords

ANTINEOPLASTIC AGENT; ANTIOXIDANT; CATECHIN; CYCLOOXYGENASE 1 INHIBITOR; EPICATECHIN; FERULIC ACID; FLAVONOID; GENTISIC ACID; LOW DENSITY LIPOPROTEIN; NITRIC OXIDE; PHENOL DERIVATIVE; POLYPHENOL; QUERCETIN; RESVERATROL; STILBENE; VANILLIC ACID; XANTHINE OXIDASE;

BODY FLUID; CHEMICAL COMPOSITION; DRUG SYNTHESIS; ENZYME INHIBITION; HISTORY; HUMAN; LIPOPROTEIN SYNTHESIS; PROPHYLAXIS; REVIEW; THROMBOCYTE AGGREGATION; WINE;

ANIMALS; CORONARY DISEASE; FLAVONOIDS; FOOD HANDLING; HISTORY, 16TH CENTURY; HISTORY, 20TH CENTURY; HISTORY, ANCIENT; HUMANS; NEOPLASMS; PHENOLS; POLYMERS; PREVENTIVE MEDICINE; ROSALES; WINE;

ANIMALIA; VITIS SP.;

EID: 0030760030     PISSN: 08878013     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-2825(1997)11:5<287::AID-JCLA6>3.0.CO;2-4     Document Type: Review

References (231)

1. Goldberg DM, Hahn SE, Parks JG: Beyond alcohol: beverage consumption and cardiovascular mortality. Clin Chim Acta 237:155-187, 1995.
2. Kannel WB, Ellison RC: Alcohol and coronary heart disease: The evidence for a protective effect. Clin Chim Acta 246:59-76, 1996.
3. Criqui MH: Alcohol and coronary heart disease: Consistent relationship and public health implications. Clin Chim Acta 246:51-57, 1996.
4. Steinmetz KA, Potter JD: Vegetables, fruit and cancer: I. Epidemiology. Cancer Causes Control 2:325-357, 1991.
5. Hertog MGL, Feakone EJM, Holleman PCH, Katan JB, Kromhout D: Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen elderly study. Lancet 342:1007-1011, 1993.
6. Hubbard RW, Mejia A, Horning M: The potential of diet to alter disease processess. Nutr Res 14:1853-1895, 1994.
7. Willet WC: Diet and health-what should we eat? Science 264:532-537, 1994.
8. McGovern P, Glusker D, Exner L: Neolithic resinated wine. Nature 381:480-481, 1996.
9. Zohary D, Hopf M: Domestication of Plants in the Old World. Oxford Univ. Press, Oxford, 1988.
10. Galet P: Vinifera wine grape varieties. In A Practical Ampelography: Grapevine Identification, 2nd ed. LT Morton, ed Comstock, Ithaca, NY, 1980, p 49-55.
11. Bourquin JC, Otter L, Walter B: Identification of grapevine rootstocks by RFLP. C R Acad Sci [III] 312:593-598, 1991.
12. Mauro M-C, Strefeler M, Weeden NF, Reisch BI: Genetic analysis of restriction fragment length polymorphisms in Vitis. J Hered 83:18-21, 1992.
13. Fanizza G. Multivariate analysis to estimate the genetic diversity of wine grapes (Vitis Vinifera) for cross breeding in southern Italy. In Proceedings of the 3rd International Symposium on Grape Breeding. VL Singleton, ed. University of California Press, Davis, 1980, p 105-110.
14. Brun S, Cabanis JC, Mestres JP: Analytical chemistry. Experientia 42:893-904, 1986.
15. Amerine MA, Roessler EB: Composition of wines. In Wines, Their Sensory Evaluation, MA Amerine, ed. Freeman, New York, 1982, p 67-80.
16. Crippen DD, Jr, Morrison JC: The effects of sun exposure on the phenolic content of Cabernet Sauvignon berries during development. Am J Enol Vitic 37:243-247, 1986.
17. Deibner L, Mourgues L, Cabibel-Hughes M: Evolution d l'indice des substances aromatiques volatiles des raisins de deux cepages rouges au cours de leur maturation. Ann Technol Agric 14:5-14, 1965.
18. Ribéreau-Gayon J, Ribéreau-Gayon P, Seguin G: Botrytis Cinerea in Enology. In The Biology of Botrytis. JR Coley-Smith, K Verhoeff, WR Jarvis, eds. Academic Press, London, 1980, p 251-274.
19. Williams AA, Rosser PR: Aroma enhancing effects of ethanol. Chem Senses 6:149-153, 1981.
20. Gnekow B, Ough CS: Methanol in wines and must. Source and amounts. Am J Enol Vitic 27:1-6, 1976.
21. Lee CY, Smith NL, Nelson RR: Relationship between pectin methyl esterase activity and formation of methanol in concord grape juice. Food Chem 4:143-148, 1979.
22. Rapp A, Mandery H: Wine aroma. Experientia 42:873-880, 1986.
23. Sponholz WR: Alcohols derived from sugars and other sources and fullbodiedness of wines. In Wine Analysis, HF Liskens, JF Jackson, eds. Springer-Verlag, Berlin, 1988, p 147-172.
24. Chen EC-H: The relative contribution of Ehrlich and biosynthetic pathways to the formation of fusel alcohols. J Am Soc Brew Chem 35:39-43, 1978.
25. 24a. Jackson RS: Chemical constituents of grapes and wine. In Wine Science: Principles and Applications, 1st ed, SL Taylor, ed. Academic Press, San Diego, 1993, p 178-219.
26. Lea AGH, Bridle P, Timberlake CF, Singleton VL: The procyanidins of white grapes and wines. Am J Enol Vitic 30:289-300, 1979.
27. Dumon MC, Michaud J, Masquelier J: Dosage des procyanides des pépins de raisin de cépages rouges et blancs du Bordelais: Bull O I V 64:533-542, 1991.
28. Kovac V, Bourzeix M, Heredia N, Ramos T: Études des catechins et proanthocyanidols de raisins et vins blancs. Rev Fr Oenol 125:7-15, 1990.
29. Hrazdina G, Parsons GF, Mattick LR: Physiological and biochemical events during development and maturation of grape berries. Am J Enol Vitic 35:220-227, 1984.
30. Packter NM: Biosynthesis of acetate-derived phenols (polyketides). In The Biochemistry of Plants, Vol 4. PK Stumpf, ed. Academic Press, New York, 1980, p 535-570.
31. Smith H, Holmes MG: The function of phytochrome in the natural environment. Measurement and calculation of phytochrome photoequilibria. Photochem Photobiol 25:547-550, 1977.
32. Smart RE, Smith SM, Winchester RV: Light quality and quantity effects on fruit ripening for Cabernet Sauvignon. Am J Enol Vitic 39:250-258, 1988.
33. Hahlbrock K: Flavonoids: In The Biochemistry of Plants, Vol 7. PK Stumpf, EE Conn, eds. Academic Press, New York, 1981, p425-456.
34. Blanke MM: Carbon economy of the grape inflorescence. Light transmission into grape berries. Wein-Wiss 45:21-23, 1990.
35. Smith S, Codrington IC, Robertson M, Smart R: Viticultural and oenological implications of leaf removal for New Zealand vineyards. In Proceedings of the 2nd International Symposium on Cool Climate Viticulture and Oenology. RE Smart SB Thornton, SB Rodriguez, JE Young, eds. New Zealand Society of Viticulture and Oenology, Auckland, 1988, p 127-133.
36. Coombe BG: Influence of temperature on composition and quality of grapes. Acta Hortic 206:23-35, 1987.
37. González-SanJosé ML, Barron LJR, Diez C: Evolution of anthocyanins during maturation of Tempranillo grape variety (Vitis vinifera) using polynomial regression models. J Sci Food Agric 51:337-343, 1990.
38. Sponholz WR: Nitrogen compounds in grapes, must and wine. In Proceedings of the International Symposium on Nitrogen in Grapes and Wine. JM Rantz, ed American Society of Enology and Viticulture, Davis, 1991, p 67-77.
39. Boulton R: The general relationship between potassium, sodium, and pH of grape juices and wines. Am J Enol Vitic 31:182-186, 1980.
40. Freeman BM, Kliewer WM: Effect of irrigation, crop level and potassium fertilization on Carignane vines. II. Grape and wine quality. Am J Enol Vitic 34:197-207, 1983.
41. Ramey D, Bertrand A, Ough CS, Singleton VL, Sanders E: Effects of skin contact temperature on Chardonnay must and wine composition. Am J Enol Vitic 37:99-106, 1986.
42. Marais J: Terpene concentrations and wine quality of Vitis vinifera L. cv.Gewü rztraminer as affected by grape maturity and cellar practices. Vitis 26:231-245, 1987.
43. 2 content and pomace contact time. Am J Enol Vitic 31:14-20, 1980.
44. Ribéreau-Gayon J, Peynard E, Ribéreau-Gayon P, Sudraud P, eds: Traité d'Oenologie: Sciences et Techniques du Vin, Vol. 3. Dunod, Paris, 1976.
45. Cuénat P, Zufferey E, Kobel D, Bregy CA, Crettenand J: Le cuvage du Pinot noir. Rôle des températures. Rev Suisse Vitic Arboric Hortic 23:267-272, 1991.
46. Rimm EB, Giovannucci EL, Willett WC, et al: Prospective study of alcohol consumption and risk of coronary disease in men. Lancet 339: 464-468, 1991.
47. Klatsky AL, Armstrong MA, Friedman GD: Alcohol and mortality. Ann Intern Med 117:646-654, 1992.
48. Gronbaek M, Deis A, Sorenson TIA, et al: Influence of sex, age, body mass index, and smoking on alcohol intake and mortality. Br Med J 308:302-306, 1994.
49. Doll R, Peto R, Hall E, et al.: Mortality in relation to consumption of alcohol: 13 years' observations on male British doctors. Br Med J 309:911-918, 1994.
50. Fuchs CS, Stampfer MJ, Colditz GA, et al.: Alcohol consumption and mortality among women. N Engl J Med 332:1245-1250, 1995.
51. Sun I, Sheten J, Cutler JA, Juller JH: Alcohol use and mortality from coronary heart disease: The role of high-density lipoprotein cholesterol. Ann Intern Med 116:881-887, 1992.
52. Gaziano JM, Buring JE, Breslow JL, et al.: Moderate alcohol intake, increased levels of high-density lipoprotein and its subfractions and decreased risk of myocardial infarction. N Engl J Med 329:1829-1834, 1993.
53. Renaud SC, Beswick AD, Fehily AM, Sharp DS, Elwood PC: Alcohol and platelet aggregation: The Caerphilly prospective heart disease study. Am J Clin Nutr 55:1012-1017, 1992.
54. Ridker PM, Vaugham DE, Stampfer MJ, Glynn RJ, Hennekens CH: Association of moderate alcohol consumption and plasma concentration of endogenous tissue-type plasminogen activator. JAMA 272:929-933, 1994.
55. Rubin R, Rand ML: Alcohol and platelet function. Alcohol Clin Exp Res 18:105-110, 1994.
56. Dunn EL, Cohen RG, Moore EE, Hamstra RD: Acute alcohol ingestion and platelet function, Arch Surg 116:1082-1083, 1981.
57. Fenn CG, Littleton JM: Inhibition of platelet aggregation by ethanol in vitro shows specificity for aggregating agent used and is influenced by platelet lipid composition. Thromb Haemost 48:49-53, 1982.
58. Mikhailidis DP, Jeremy JY, Barradas MA, Green N, Dandona P: Effect of ethanol on vascular prostacyclin synthesis, platelet aggregation and platelet thromboxane release. Br Med J 287:1495-1498, 1983.
59. Galli C, Colli S, Gianfranceshi G: Acute effects of ethanol, caffeine, or both on platelet aggregation, thromboxane formation, and plasma free fatty acids in normal subjects. Drug-Nutr Interact 3:6107, 1984.
60. Landolfi R, Steiner M: Ethanol raises prostacyclin in vivo and in vitro. Blood 64:679-682, 1984.
61. Rand ML, Packham MA, Kinlough-Rathbone RL, Mustard JF: Effects of ethanol on pathways of platelet aggregation in vitro. Thromb Haemost 59:383-387, 1988.
62. Veenstra J, Kluft C, Ockhuizen T, Pol HVD, Wedel M, Schaafsma G: Effects of moderate alcohol consumption on platelet function, tissue-type plasminogen activator and plasminogen activator inhibitor. Thromb Haemost 63:345-348, 1990.
63. Torel J, Cillard J, Cillard P: Antioxidant activity of flavonoids and reactivity with peroxyl radical. Phytochemistry 25:383-385, 1986.
64. Bors W, Saran M: Radical scavenging by flavonoid antioxidants Free Radic Res Commun 2:289-294, 1987.
65. Slater TF, Cheeseman KH, Davies MJ, et al: Free radical scavenging properties of modulators of eicosanoid metabolism. Adv Prostaglandin Thromboxane Res 17:1098-1102, 1987.
66. Afanas'ev IB, Dorozhko AI, Brodskii AV, Kostyuk VA, Potapovitch AI: Chelating and free radical scavenging mechanisms of inhibitory actions of rutin and quercetin in lipid peroxidation. Biochem Pharmacol 38:1763-1769, 1989.
67. De Whalley CV, Rankin SM, Hoult JRS, Jessup W, Leakes DS: Flavonoids inhibit the oxidative modification of low-density lipoproteins by macrophages Biochem Pharmacol 39:1743-1745, 1990.
68. Mangiapane H, Thomson J, Salter A, Brown S, Bell GD, White DA: The inhibition of the oxidation of low density lipoprotein by (+)-catechin, a naturally occurring flavonoid. Biochem Pharmacol 43:445-450, 1992.
69. St. Leger AS, Cochrane AL, Moore F: Factors associated with cardiac mortality in developed countries with particular reference to the consumption of wine. Lancet 1:1017-1020, 1979.
70. Nanji AA: Alcohol and ischemic heart disease: Wine, beer, or both? Int J Cardiol 8:487-489, 1985.
71. Nanji AA, French SW: Alcoholic beverages and coronary heart disease. Atherosclerosis 60:197-198, 1986.
72. Hegsted DM, Ausman LM: Diet, alcohol and coronary heart disease in men. J Nutr 118:1184-1189, 1988.
73. Renaud S, De Lorgeril M: Wine, alcohol, platelets, and the French paradox for coronary heart disease. Lancet 339:1523-1526, 1992.
74. Rosenberg L, Slone D, Shapiro S, Kaufman DW, Miettinen OS, Stolley PD: Alcoholic beverages and myocardial infarction in young women. Am J Public Health 71:82-85, 1981.
75. Gronbaek AD, Sorenson TIA, Becker U, Schnohr P, Jensen G: Mortality associated with moderate intakes of wine, beer, or spirits. Br Med J 310:1165-1169, 1995.
76. Criqui HM: The reduction of coronary heart disease with light to moderate alcohol consumption: effect or artifact? Br J Addict 85:854-857, 1990.
77. Yano K, Rhoads CG, Kagan A: Coffee, alcohol and risk or coronary heart disease among Japanese men living in Hawaii. N Engl J Med 297:405-409, 1977.
78. Klatsky AL, Armstrong MA, Friedman GD: Relations of alcoholic beverage use to subsequent coronary artery disease hospitalization. Am J Cardiol 58:710-714, 1986.
79. Rimm EB, Klatsky A, Grobbe D, Stampfer MJ: Review of moderate alcohol consumption and reduced risk of coronary heart disease: Is the effect due to beer, wine, or spirits? Br Med J 312:731-736, 1996.
80. Weisse ME, Eberly B, Person DA: Wine as a digestive aid: Comparative antimicrobial effects of bismuth salicylate and red and white wine. Br Med J 311:1657-1660, 1995.
81. Fugelsang KC, Muller CJ: The in vitro effect of red wine on Helicobacter pylori. In Wine in Context: Nutrition, Physiology, Policy. AL Waterhouse, JM Rantz, eds. Proceedings of the Symposium on Wine Health, American Society of Enology and Viticulture, Davis, 1996, p 43-45.
82. Klurfeld DM, Kritchevsky D: Differential effects of alcoholic beverages on experimental atherosclerosis in rabbits. Exp Mol Pathol 34:62-71, 1981.
83. Yugarani T, Tan BKH, Teh M, Das NP: Effects of polyphenolic natural products on the lipid profiles of rats fed high fat diets. Lipids 27:181-186, 1992.
84. Tebib K, Bitri L, Besancon P, Rouanet J-M. Polymeric grape seed tannins prevent plasma cholesterol changes in high-cholesterol-fed rats. Food Chem 49:403-406, 1994.
85. Ruf J-C, Berger J-L, Renaud S: Platelet rebound effect of alcohol withdrawal and wine drinking in rats. Arterioscler Thromb Vasc Biol 15:140-144, 1995.
86. Renaud SC, Ruf J-C: Effects of alcohol on platelet functions. Clin Chim Acta 246:77-89, 1996.
87. Demrow HS, Slane PR, Folts JD: Administration of wine and grape juice inhibits in vivo platelet activity and thrombosis in stenosed canine coronary arteries. Circulation 91:1182-1188, 1995.
88. Seigneur M, Bonnet J, Dorian B, et al.: Effect of the consumption of alcohol, white wine, and red wine on platelet function and serum lipids. J Appl Cardiol 5:215-222, 1990.
89. Lavy A, Furhman B, Markel A, et al.: Effect of dietary supplementation of red or white wine on human blood chemistry, hematology, and coagulation: Favourable effect of red wine on plasma high-density lipoprotein. Ann Nutr Metab 38:287-294, 1994.
90. Struck M, Watkins T, Tomeo A, Halley J, Bierenbaum M: Effect of red and white wine on serum lipids, platelet aggregation, oxidation products and antioxidants: A preliminary report. Nutr Res 14:1811-1819, 1994.
91. Fuhrman B, Lavy A, Aviram M: Consumption of red wine with meals reduces the susceptibility of human plasma and low density lipoprotein to lipid peroxidation. Am J Clin Nutr 61:549-554, 1995.
92. Pace-Asciak CR, Rounova O, Hahn SE, Diamandis EP, Goldberg DM: Wines and grape juices as modulators of platelet aggregation in healthy human subjects. Clin Chim Acta. 246:163-182, 1996.
93. Goldberg DM, Garovic-Kocic V, Diamandis EP, Pace-Asciak CR: Wine: Does the colour count? Clin Chim Acta 246:183-193, 1996.
94. Singleton VL: Grape and wine phenolics; background and prospects. In Proceedings of The University of California, Davis, Grape and Wine Centennial Symposium. AD Webb, ed. University of California Press, Davis, 1982, p 215-227.
95. Swain T: The evolution of flavonoids. In Plant Flavonoids in Biology and Medicine. V Cody, E Middleton, JB Harborne, eds. Alan R. Liss, New York, 1986, p 1-14.
96. Denno RF, McClure MS (eds.): Variable Plants and Herbivores in Natural and Managed Systems. Academic Press, New York, 1983.
97. Frankel EN: In search of better methods to evaluate natural antioxidants and oxidative stability in food lipids. Trend Food Sci Technol 4:220-225, 1993.
98. Loomis WD: Overcoming problems of phenolics and quinones in the isolation of plant enzymes and organelles. Methods Enzymol 31:528-544, 1974.
99. Oh HI, Hoff JE, Armstrong GF, Haff LA: Hydrophobic interaction in tannin-protein complexes. J Agric Food Chem. 28:394-398, 1980.
100. Hasegawa S, Maier VP: Biosynthesis of trans-cinnamate from phenyl pyruvate and L-glutamate by cell-free extracts of grapefruit. Phytochemistry 9:2483-2490, 1970.
101. Hrazdina G, Parsons GF, Mattick LR: Physiological and biochemical events during development and maturation of grape berries. Am J Enol Vitic 35:220-227, 1984.
102. 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 56:205-213, 1975.
103. Gorham JL: The stilbenoids. Progr Phytochem 6:203-252, 1980.
104. Pratt DE, Hudson BJF: Natural antioxidants not exploited commercially. In Food antioxidants. BJF Hudson, ed. Elsevier, London, 1990, p 171-191.
105. Mehta AC, Seshadi TR: Flavonoids as antioxidants. J Sci Industr Res 18B:24-28, 1959.
106. Pratt DE, Watts BM: The antioxidant activity of vegetable extracts. I Flavone aglycones. J Food Sci 29:27-33, 1964.
107. Darmon N, Fernandez Y, Cambon-Gros C, Mitjavila S: Quantification of the scavenger capacity of different flavonoids in regards to the superoxide ion. Foods Addit Contam 7:560-563, 1990.
108. Letan A: The relation of structure to amioxidant activity of quercetin and some of its derivatives. Primary activity. J Food Sci 31:518-523, 1966.
109. Teissedre PL, Frankel EN, Waterhouse AL, Peleg H, German JB; Inhibition of in vitro human LDL oxidation by phenolic antioxidants from grapes and wines. J Sci Food Agric 70:55-61, 1996.
110. Packer L. Interactions among antioxidants in health and disease: Vitamin E and its redox cycle Proc Soc Exp Biol Med 200:271-276, 1992.
111. Mehra MR, Lavie CJ, Ventura HO, Milani RV: Prevention of atherosclerosis: the potential roles of antioxidants. Postgrad Med 98:175-184, 1995.
112. Byers T, Bowman B: Vitamin E supplements and coronary heart disease. Nutr Rev 51:333-336, 1993.
113. Gaziano JM: Antioxidant vitamins and coronary artery disease risk. Am J Med 97:185-195, 1994.
114. Stampfer MJ, Rimm EB: Epidemiologic evidence for Vitamin E in prevention of cardiovascular disease. Am J Clin Nutr 62:1365S-1369S, 1995.
115. Maxwell S, Cruikshank A, Thorpe G: Red wine and antioxidant activity in serum. Lancet 344:193-194, 1994.
116. Whitehead TP, Robinson D, Allaway S, Syms J, Hale A: Effect of red wine ingestion on the antioxidant capacity of serum. Clin Chem 41:32-35, 1995.
117. Steinberg D, Parsatharathy S, Carew TE, Khoo JC, Witztum JL: Beyond cholesterol. Modifications of low-density lipoprotein that increase its atherogenicity. N Engl J Med 320:915-924, 1989.
118. Steinberg D. LDL oxidation and atherogenesis. Atherosclerosis IX. In Proceedings of the Ninth International Simposium on Atherosclerosis. O Stein, S Eisenberg, Y Stein, eds. R and D Creative Communications, Tel Aviv, 1992, p 41-46.
119. Witzum JL: The oxidation hypothesis of atherosclerosis. Lancet 344:793-795, 1994.
120. Frankel EN, Kanner J, German JB, Parks E, Kinsella JE: Inhibition of oxidation of human low-density lipoprotein by phenolic substances in red wine. Lancet 341:454-457, 1993.
121. Frankel EN, Waterhouse AL, Kinsella JE: Inhibition of human LDL oxidation by resveratrol. Lancet 341:1103-1104, 1993.
122. Kanner J, Frankel E, Granit R, German B, Kinsella JE: Natural antioxidants in grapes and wines. J Agric Food Chem 42:64-69, 1994.
123. Frankel EN, Waterhouse AL, Tetssedre PL: Principal phenolic phytochemicals in selected California wines and their antioxidant activity in inhibiting oxidation of human low-density lipoproteins. J Agric Food Chem 43:890-894, 1995.
124. Frankel EN, German JB, Davis PA: Headspace gas chromatography to determine human low density lipoprotein oxidation. Lipids 27:1047-1051, 1992.
125. Castelluccio C, Paganga G, Melikian N, et al.: Antioxidant potential of intermediates in phenylpropanoid metabolism in higher plants. FEBS Lett 368:188-192, 1995.
126. Vinson JA, Hontz, BA: Phenol antioxidant index: comparative antioxidant effectiveness of red and white wines. J Agric Food Chem 43:401-403, 1995.
127. Laranjinha J, Vieira O, Madeira V, Almeida L: Two related phenolic antioxidants with opposite effects on Vitamin E content m low density lipoproteins oxidized by ferrylmyoglobin consumption vs regeneration Arch Biochem Biophys 323:373-381, 1995.
128. Jessup W, Rankin SM, De Whalley CV, Hoult JR, Scott J, Leake DS: Alpha-tocopherol consumption during low-density-lipoprotein oxidation. Biochem J 265:399-405, 1990.
129. Negre-Salvayre A, Alomar Y, Troly M, Salvayre R: Ultraviolet-treated lipoproteins as a model system for the study of the biological effects of lipid peroxides on cultured cells: The protective effect of antioxidants (probucol, catechin, Vitamin E) against the cytotoxicity of oxidized LDL occurs in two ways. Biochim Biophys Actai 1096:291-300, 1991.
130. Ikeda I, Imasato Y, Sasaki E, et al.: Tea catechins decrease micellar solubility and intestinal absorption of cholesterol in rats. Biochim Biophys Acta 1129:141-146, 1992.
131. Igarashi K, Ohmuma M. Effects of isorhamnetin, rhamnetin, and quercetin on the concentrations of cholesterol and lipoperoxide in the serum and liver and on the blood and liver antioxidative enzyme activities of rats. Biosci Biotech Biochem 59:595-601, 1995.
132. Laughton MJ, Halliwell B, Hoult JRS: Inhibition of flavonoids of lipid peroxidation, 5-lipoxygenase, and cyclo-oxygenase: Distinct structure-activity relationships. In Flavonoids in Biology & Medicine III. Current Issues in Flavonoid Research National University of Singapore, Singapore, 1990, p 245-249.
133. Yutin C, Ronglian Z, Zhongjian J, Yong J: Flavonoids as superoxide scavengers and antioxidants. Free Radic Biol Med 9:19-21, 1990.
134. Scott BC, Butler J, Halliwell B, Aruoma OI: Evaluation of the antioxidant actions of ferulic acid and catechins. Free Radic Res Commun 19:241-253, 1993.
135. Salah N, Miller NJ, Paganga G, Tijburg L, Bolwell GP, Rice-Evans C: Polyphenolic flavonols as scavengers of aqueous phase radicals and as chain-breaking antioxidants. Arch Biochem Biophys 322:339-346, 1995.
136. Terao J, Piskula M, Yao Q: Protective effect of epicatechin, epicatechin gallate, and quercetin on lipid peroxidation in phospholipid bilayers. Arch Biochem Biophys 308:278-284, 1994.
137. Ioku K, Tsushida T, Takei Y, Nakatani N, Terao J: Antioxidative activity of quercetin and quercetin monoglucosides in solution and phospholipid bilayers. Biochim Biophys Acta 1234:99-104, 1995.
138. Ruch RJ, Cheng S, Klaunig, JE: Prevention of cytotoxicity and inhibition of intercellular communication by antioxidant catechins isolated from Chinese green tea. Carcinogenesis 10:1003-1008, 1989.
139. Wallett JC, Gaydon EM, Cotelle N, Bernier JL, Henichart JP, Catteau JP: Antiradical and antioxidant properties of ten synthetic flavones. In Proceedings of the Sixteenth International Group Polyphenols Symposium. D.T.A. Publishing, Paris, 1992, p 343-345.
140. Yokozawa T, Oura H, Nakagawa H, Sakamaka S, Kim M: Effects of a component of green tea on the proliferation of vascular smooth muscle cells. Biosci Biotechnol Biochem 59:2134-2136, 1995.
141. Nakayama T: Suppression of hydroperoxide-induced cytotoxicity by polyphenols. Cancer Res 54:1991s-1993s, 1994.
142. Subirade I, Fernandez Y, Periquet A, Mitjavila S: Catechin protection of 3T3 Swiss fibroblasts in culture under oxidative stress. Biol Trace Elem Res 47:313-319, 1995.
143. McCord JM, Fridovich I: The reduction of cytochrome C by milk xanthine oxidase. J Biol Chem 243:5753-5760, 1968.
144. Hearse DJ, Manning AS, Downey JM, Yellon DM: Xanthine oxidase: A critical mediator of myocardial injury during ischemia and repefusion. Acta Physiol Scand (Suppl) 548:65-78, 1986.
145. Chan PH, Schimidley JW, Fishman RA, Longar SM: Brain injury, edema and vascular permeability changes induced by oxygen-derived free radicals. Neurology 34:315-320, 1984.
146. Bowman WC, Rand MJ: The blood: Drugs affecting coagulation, fibrinolysis, haematopoiesis and the functioning of blood cells. In Textbook of Pharmacology, 2nd ed. Blackwell, Australia, 1980, p 21.3.
147. Kokuglu E, Belce A, Ozyurt E, Tepeler Z: Xanthine oxidase levels in human brain tumors. Cancer Lett 50:179-181, 1990.
148. Chang W-S, Lee Y, Lu F, Chiang H: Inhibitory effects of flavonoids on xanthine oxidase. Anticancer Res 13:2165-2170, 1993.
149. Keaney JF, Jr: Atherosclerosis, oxidative stress, and antioxidant protection in endothelium-derived relaxing factor action. Progr Cardivasc Dis 38:129-154, 1995.
150. Fitzpatrick DF, Hirschfield SL, Coffey RG: Endothelium-dependent vasorelaxing activity of wine and other grape products. Am J Physiol 265:H774-H778, 1993.
151. Elwood PC, Renaud S, Sharp DS, Beswick AD, O'Brien JR, Yarnell JWG: Ischemic heart disease and platelet aggregation. Circulation 83:38-44, 1991.
152. Ferrell JE, Peter DG, Sing C, et al.: Structure-activity studies of flavonoids as inhibitors of cAMP phosphodiesterase and relationship to quantum chemical indices. Mol Pharmacol 16:556-568, 1979.
153. Ruckstuhl M, Beretz A, Anton R, Landry Y: Flavonoids are selective cGMP phophodiesterase inhibitors. Biochem Pharmacol 28:535-538, 1979.
154. Beretz A, Stierle A, Anton R, Cazenave JP: Role of cAMP in the inhibition of human platelet aggregation by quercetin, a flavonoid that potentiates the effect of prostacyclin. Biochem Pharmacol 31:3597-3600, 1981.
155. Mower R, Landolfi R, Steiner M: Inhibition in vitro of platelet aggregation and arachidonic acid metabolism by fiavone. Biochem Pharmacol 33:357-363, 1984.
156. Landolfi R, Mower R, Steiner M: Modification of platelet function and arachidonic acid metabolism by bioflavonoids. Biochem Pharmacol 33:1525-1530, 1984.
157. Corvazier E, Maclouf J: Interference of some flavonoids and non-steroidal drugs with oxidative metabolism of arachidonic acid by human platelets and neutrophils. Biochim Biophys Acta 835:315-321, 1985.
158. Gryglewski R, Korbut R, Robak J, Swies J: On the mechanism of antithrombotic action of flavonoids. Biochem Pharmacol 36:317-322, 1987.
159. Pace-Asiak CR, Hahn S, Diamandis E, Soleas G, Goldberg DM: The red wine phenolics trans-resveratrol and quercetin block human platelet aggregation and eicosanoid synthesis: Implications for protection against coronary heart disease. Clin Chim Acta 235:207-219, 1995.
160. Garcia Barroso C, Cela Torrijos R, Perez-Bustamante JAA: Study of behavioural grouping of polyphenolic species in "Fino" sherry wine. Z Lebensm Unters Forsch 18:307-314, 1987.
161. Mahler S, Edwards PA, Chisholm MG: HPLC identification of phenols in Vidal Blanc wines using electrochemical detection. J Agric Food Chem 36:946-951, 1988.
162. Singleton VL, Esau P: Phenolic Substances in Grapes and Wines and their Significance. Academic Press, New York, 1969.
163. Woodring PJ, Edward PA, Chisholm MG: HPLC determination of non-flavonoid phenols in vidai blanc wine using electrochemical detection. J Agric Food Chem 38:729-732, 1990.
164. Betts WH, Whitehouse MW, Cleland TJ, Vemon-Roberts B: In vitro antioxidant properties of potential biotransformation products of salicylate, sulphasalazine, and amidopyrine. Free Radic Biol Med 1:273-280, 1985.
165. Budavari S (ed): The Merck Index, 11th ed. Merck and Co., New Jersey, 1989, 688.
166. Curelier ME, Richard TT, Berset C: Comparison of antioxidative activity of some acid-phenols: Structure-activity relationships. Biosci Biotech Biochem 56:324-325, 1992.
167. Samuelson B: Leukotrienes: Mediators of immediate hypersensitivity reactions and inflammation. Science 220:568-575, 1983.
168. Parsatharathy S, Wieland E, Steinberg D: A role for endothelial cell lipoxygenase in the oxidative modification of low-density lipoprotein. Proc Nat Acad Sci USA 86:1046-1050, 1989.
169. Ross R: The pathogenesis of atherosclerosis: A perspective for the 1990s. Nature 362:801-809, 1993.
170. Moroney M-A, Alcaraz MJ, Forden RA, Carey F, Hoult JRS: Selectivity of neutrophil 5-lipoxygenase and cycloxygenase inhibition by an anti-inflammatory flavonoid glycoside and related aglycone flavonoids. J Pharm Pharmacol 40:787-792, 1988.
171. Goldberg DM, Soleas GJ, Hahn SE, Diamandis EP, Karumanchiri A: Identification and assay of trihydroxystilbenes in wine and their biological properties. In Wine Composition and Health Benefits. T Watkins, ed. American Chemical Society, Washington, 1996, p. 24-43.
172. Pace-Asciak CR: Hepoxilins. Gen Phannacol 24:805-810, 1993.
173. Spector AA, Moore SA, Gordon EEI, Gordon JA, Kaduce TL: HETEs and endothelial function. In Proceedings of the Ninth International Symposium on Atherosclerosis. O Stein, S Eisenberg, Y Stein, eds. R and L Creative Communications, Tel Aviv, 1992, p 367-370.
174. Ohki S, Ogino N, Yamamoto S, Hayaishi O: Prostaglandin hydroperoxidase, an integral part of prostaglandin endoperoxide synthetase from bovine vesicular glands. J Biol Chem 254:829-836, 1979.
175. Pagels WR, Sachs RJ, Mamett LJ, Dewitt DL, Day JS, Smith WL: Immunochemical evidence for the involvement of prostaglandin H synthase in hydroperoxide-dependent oxidations by ram seminal vesicle microsomes. J Biol Chem 258:6517-6523, 1983.
176. Bakovic M, Dunford HB: Oxidation kinetics of caffeic acid by prostaglandin H synthase: Potential role in regulation of prostaglandin biosynthesis. Prostaglandins Leukot Essent Fatty Acids 51:337-345, 1994.
177. Koshihara Y, Neichi T, Murota SI, Lao AN, Fujimoto Y, Tatsuno T: Caffeic acid is a selective inhibitor for leukotriene biosynthesis. Biochim Biophys Acta 792:92-97, 1984.
178. Kemal C, Louis-Flamberg P, Krupinski-Olsen R, Shorter AL: Reductive inactivation of soybean lipoxygenase I by catechols' A possible mechanism for regulation of lipoxygenase activity. Biochemistry 26:7064-7072, 1987.
179. 2 by quercetin. Inflammation 17:573-582, 1993.
180. 2: Function and pharmacological regulation. Biochem Pharmacol 36:2429-2436, 1987.
181. 2 gene expression in human hepatoma cells by mediators of the acute phase response. J Biol Chem 266:2647-2651, 1981.
182. 2 - a mediator between proximal and distal effectors of inflammation. Immunol Today 12:143-146, 1991.
183. Suolinna EM, Buchsbaum RN, Racker E: The effect of flavonoids on aerobic glycolysis and growth of tumor cells. Cancer Res 35:1865-1872, 1975.
184. Markaverich BM, Roberts RR, Alejandro MA, Johson GA, Middleditch BS, Clark JH: Bioflavonoid interaction with rat uterine type II binding sites and cell growth inhibition. J Steroid Biochem 30:71-78, 1988.
185. Castillo MH, Perkins E, Campbell JH, et al.: The effects of the bioflavonoid quercetin on squamous cell carcinoma of head and neck origin. Am J Sur 158:351-355, 1989.
186. Yoshida M, Sakai T, Hosokawa N, et al.: The effect of quercetin on cell cycle progression and growth of human gastric cancer cells. FEBS Lett 260:10-13, 1990.
187. Hosokawa N, Hosokawa Y, Sakai T, et al.: Inhibitory effect of quercetin on the synthesis of a possible cell-cycle-related 17 kDa protein in human colon cancer cells. Int J Cancer 45:1119-1124, 1990.
188. Uddin S, Choudhry MA: Quercetin, a bioflavonoid, inhibits the DNA synthesis of human leukemia cells. Biochem Mol Biol Int 36:545-550, 1995.
189. 1 phase of the cell cycle. Cancer Res 52:6676-6681, 1992.
190. Avila MA, Velasco JA, Cansado J, Notario V: Quercetin mediates the down-regulation of mutant p53 in the human breast cancer cell line MDA-MB468. Cancer Res 54:2424-2428, 1994.
191. Wei Y, Zhao X, Kariya Y, Gukata H, Teshigawara K, Uchida A: Induction of apoptosis by quercetin: involvement of heat shock protein. Cancer Res 4952-4957, 1994.
192. + adenosine triphosphatase and its partial reactions by quercetin. Biochemistry 15:4951-4958, 1974.
193. Beretz A, Anton R, Stodet JC: Flavonoid compounds are potent inhibitors of cyclic AMP phosphodiesterase. Experientia 34:1054-1055, 1977.
194. Graziani Y, Chayoth R: Regulation of cyclic AMP level and synthesis of DNA, RNA, and protein by quercetin in Ehrlich ascites tumor cells. Biochem Pharmacol 28:397-403, 1979.
195. Levi J, Teuerstien I, Marbach M, Radians S, Sharoni Y: Tyrosine protein kinase activity in the DMBA-induced rat mammary tumor: inhibition by quercetin. Biochem Biophys Res Commun 123:1224-1233, 1984.
196. Akiyama T, Ishida J, Nakagawa S, et al.: Genistein, a specific inhibitor of tyrosine-spectfic protein kinases. J Biol Chem 262:5592-5595, 1987.
197. Ruckstuhl M, Beretz A, Anton R, Landry Y: Flavonoids are selective cyclic GMP phosphodiesterase inhibitors. Biochem Pharmacol 28:535-538, 1979.
198. Gschwendt M, Horn F, Killestein W, Marks I: Inhibition of the calcium and phospholipid-dependent protein kinase activity from mouse brain cytosol by quercetin. Biochem Biophys Res Commun 117:444-447, 1983.
199. 2+)-ATPase of sarcoplasmic reticulum. J Biol Chem 256:887-892, 1981.
200. Glossmann H, Presek P, Eigenbrot E: Quercetin inhibits tyrosine phosphorylation by the cyclic nucleotide-independent transforming protein kinase. Naunyn-Schmeideberg Arch Pharmakol 317:100-102, 1981.
201. Ono K, Nakane H, Fukushima M, Cherman J-C, Barre-Sinoussi F: Differential inhibitory effects on the activities of reverse transcriptase and cellular DNA and RNA polymerases. Eur J Biochem 190:469-476, 1990.
202. Matter WF, Brown RF, Vlahos CJ: The inhibition of phosphatidylinositol 3-kinase by quercetin and analogues. Biochem Biophys Res Commun 186:624-631, 1992.
203. Rizzo MT, Weber G: 1-phosphotidylinositol 4-kinase: An enzyme linked with proliferation and malignancy. Cancer Res 54:2611-2614, 1994.
204. Yeh YA, Herenyiora M, Sledge GW, Weber G: Quercetin: Synergistic action with carboxyamidotriazole in human breast carcinoma cell lines. Proc Am Assoc Cancer Res 36:295, 1995.
205. Yanagihara K, Ito A, Toge T, Numoto M: Antiproliferative effects of isoflavones on human cancer cell lines established from the gastrointestinal tract. Cancer Res 53:5815-5821, 1993.
206. Scambia G, Ranelletti FO, Benedetti P, et al.: Inhibitory effect of quercetin on OVA 433 cells and presence of type II estrogen binding sites in primary ovarian tumours and cultured cells. Br J Cancer 62:942-946, 1990.
207. Scambia G, Ranelletti FO, Benedetti PP, et al.: Inhibitory effect of quercetin (q) on primary ovarian and endometrial cancers and synergistic activity with cis-diamminedichloroplatinum (II) (CDDP). Proc Am Soc Clin Oncol 11:760, 1992.
208. Teofili L, Pierelli L, Iovino S, et al.: The combination of quercetin and cytosine arabinoside synergistically inhibits leukemic cell growth. Leuk Res 16:479-503, 1992.
209. Hoffmann J, Fiebig HH, Winterhalter BR, et al.: Enhancement of the antiproliferative activity of cis-diamminedichloroplatinum (II) by quercetin. Int J Cancer 45:536-539, 1990.
210. Manach C, Morand C, Texier O, et al.: Quercetin metabolites in plasma of rats fed diets containing rutin or quercetin. J Nutr 125:1911-1922, 1995.
211. Xu X, Wang HJ, Murphy PA, Cook L, Hendrich S: Daidzein is a more bioavailable soymilk isoflavone than is genistein in adult women. J Nutr 124:825-832, 1994.
212. Ferry DR, Smith A, Malkhandi J, et al.: Phase I clinical trial of the flavonoid quercetin: Pharmacokinetics and evidence for in vivo tyrosine kinase inhibition. Clin Cancer Res 2:659-668, 1996.
213. Huang MT, Wood AW, Newmark HL, et al.: Inhibition of the mutagenicity of bay-region diol-epoxides of polycyclic aromatic hydrocarbons by phenolic plant flavonoids. Carcinogenesis 4:1631-1637, 1983.
214. Alldrick AJ, Flynn J, Rowland IR: Effect of plant-derived flavonoids and polyphenolic acids on the activity of mutagens from cooked food. Mutat Res 163:225-232, 1986.
215. Nakadate T, Yamamoto S, Aizu E, Kato R: Effects of flavonoids and antioxidants on 12-O-tetradecanoylphorbol-13-acetate caused epidermal ornithine decarboxylase induction and tumor promotion in relation to lipoxygenase inhibition by these compounds. Gann 75:214-222, 1984.
216. Liu L, Castonguay A: Inhibition of the metabolism and genotoxicity of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in rat hepatocytes by (+)-catechin. Carcinogenesis 12:1203-1208, 1991.
217. Fan XJ: In vitro effect of catechin on cell growth. Chung Hua Chung Liu Tsa Chih 14:190-192, 1992.
218. Kuenzig W, Chan J, Norkus E, et al.: Caffeic acid and ferulic acid as blockers of nitrosamine formation. Carcinogenesis 5:309-313, 1984.
219. San RH, Chan RI: Inhibitory effect of phenolic compounds on aflatoxin BI metabolism and induced mutagenesis. Mutat Res 177:229-239, 1987.
220. Huang MT, Smart RC, Wong CQ, Conney AH: Inhibitory effect of curcumin, chlorogenic acid, caffeic acid, and ferulic acid on tumor promotion in mouse skin by 12-O-tetradecanoylphorbol-13-acetate. Cancer Res 48:5941-5946, 1988.
221. Chen G, Perchellet EM, Gao XM, et al.: Ability of m-chloroperoxybenzoic acid to induce the ornithine decarboxylase marker of skin tumor promotion and inhibition of this response by gallotannins, oligomeric proanthocyanidins, and their monomeric units in mouse epidermis m vivo. Anticancer Res 15:1183-1189, 1995.
222. Wattenberg LW, Coccia JB, Lam LK: Inhibitory effects of phenolic compounds on benzo (α) pyrene-induced neoplasia. Cancer Res 40:2820-2823, 1980.
223. Raj AS, Heddle JA, Newmark HL, Katz M: Caffeic acid as an inhibitor of DMBA-induced chromosomal breakage in mice assessed by bone-marrow micronucleus test. Mutat Res 124:247-253, 1983.
224. Stavric B: Quercetin in our diet: From potent mutagen to a probable anticarcinogen. Clin Biochem 27:245-248, 1994
225. Henneckens CH, Buring JE, Peto R: Antioxidant vitamins-benefits not yet proved. N Engl J Med 330:1080-1081, 1994.
226. Waterhouse AL, Frankel EN: Wine antioxidants may reduce heart disease and cancer. In Proceedings OIV 73rd General Assembly. OIV Press, Paris, 1993, p 1-15.
227. Goldberg DM: Does wine work? Clin Chim Acta 41:14-16, 1995.
228. Soleas GJ, Diamandis EP, Goldberg DM: Resveratrol: A molecule whose time has come? and gone? Clin Biochem 30:91-113, 1997.
229. Jeandet P, Bessis R, Maume BF, Meunier P, Peyron D, Trollat P: Effect of enological practices on the resveratrol isomer content of wine. J Agric Food Chem 43:316-319, 1995.
230. 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 46:363-367, 1995.
231. Soleas GJ, Goldberg DM, Karumanchiri A, Diamandis EP, Ng E: Influences of viticultural and oenological factors on changes in cis- and trans-resveratrol in commercial wines. J Wine Res 2:107-121, 1995.