Quercetin and p-coumaric acid concentrations in commercial wines

American Journal of Enology and Viticulture

Volumn 49, Issue 2, 1998, Pages 142-151

  Goldberg, David M ^a   Tsang, Elisa ^b   Karumanchiri, Alex ^b   Soleas, George J ^c  

^a UNIVERSITY OF TORONTO   (Canada)

^b Liquor Control Board of Ontario   (Canada)

^c Andres Wines Ltd   (Canada)

Author keywords

Coumaric acid; Quercetin

Indexed keywords

AUSTRALIA; FLAVANOL; FLAVONOID; FOOD ANALYSIS; FRANCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PARA COUMARIC ACID; PHENOLIC ACID; QUERCETIN; SOUTH AFRICA; SOUTH AMERICA; TRIHYDROXYSTILBENE; UNITED STATES; WINE;

EID: 0031810594     PISSN: 00029254     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (78)

1. Achilli, G., G. P. Cellerino, and P. H. Gamache. Identification and determination of phenolic constituents in natural beverages and plant extracts by means of a coulometric electrode array system. J. Chromatogr. 632:111-117 (1993).
2. Akiyama, T., J. Ishida, S. Nakagawa, et al. Genistein, a specific inhibitor of tyrosine-specific protein kinases. J. Biol. Chem. 262:5592-5595 (1987).
3. Avila, M. A., J. A. Velasco, J. Cansado, and V. Notario. Quercetin mediates the down-regulation of mutant p53 in the human breast cancer cell line MDA-MB468. Cancer Res. 54:2424-2428 (1994).
4. Bakovic, M., and H. B. Dunford. Oxidation kinetics of caffeic acid by prostaglandin H synthase: potential role in regulation of prostaglandin biosynthesis. Prost. Leukot. Essent. Fatty Acids 51:337-345 (1994).
5. Beretz, A., R. Anton, and J. C. Stodet. Flavonoid compounds are potent inhibitors of cyclic AMP phosphodiesterase. Experientia 34:1054-1055 (1977).
6. Beretz, A., A. Stierle, et al. 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).
7. Castelluccio C., G. Paganga, et al. Antioxidant potential of intermediates in phenylpropanoid metabolism in higher plants. FEBS Lett. 368:188-192 (1995).
8. Castillo, M. H., E. Perkins, J. H. Campbell, et al. The effects of the bioflavonoid quercetin on squamous cell carcinoma of head and neck origin. Am. J. Surgery 158:351-355 (1989).
9. 2: Function and pharmacological regulation. Biochem. Pharmacol. 36:2429-2436 (1987).
10. Chang, W.-S., Y. Lee, F. Lu, and H. Chiang. Inhibitory effects of flavonoids on xanthine oxidase. Anticancer Res. 13:2165-2170 (1993).
11. Criqui, M. H. Alcohol and coronary heart disease: consistent relationship and public health implications. Clin. Chim. Acta 246:51-57 (1996).
12. Corvazier, E., and J. MacLouf. 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).
13. Ferry D. R., A. Smith. J. Malkhandi, D.W. Fyfe, 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).
14. Fitzpatrick, D. F., S. L. Hirshfield, and R.G. Coffey. Endothelium-dependent vasorelaxing activity of wine and other grape products. Am. J. Physiol. 265:H774-H778 (1993).
15. Frankel, E. N., J. Kanner, J. B. German, E. Parks, and J.E. Kinsella. Inhibition of oxidation of human low-density lipoprotein by phenolic substances in red wine. Lancet 341:454-457 (1993).
16. Frankel, E. N., A. L. Waterhouse, and J.E. Kinsella. Inhibition of human LDL oxidation by resveratrol. Lancet 341:1103-1104 (1993).
17. Frankel, E. N., A. L. Waterhouse, and P.L. Teissedre. 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).
18. Fritzemeier, K. H., and H. Kindl. Coordinate induction by ultraviolet light of stilbene synthase, phenylalanine ammonia lyase and cinnamate-4-hydroxylase in leaves of Vitaceae. Planta 151:48-52 (1981).
19. Glossmann, H., P. Presek, and E. Eigenbrot. Quercetin inhibits tyrosine phosphorylation by the cyclic nucleotide-independent transforming protein kinase. Naunyn-Schmeideberg Arch. Pharmakol. 317:100-102 (1981).
20. Goldberg, D. M., S. E. Hahn, and J. G. Parkes. Beyond alcohol: beverage consumption and cardiovascular mortality. Clin. Chim. Acta 237:155-187 (1995).
21. Goldberg, D. M., A. Karumanchiri, E. Tsang, et al. Catechin and epicatechin concentrations of red wines. Regional and cultivar-related differences. Am. J. Enol. Vitic. 49:23-34 (1998).
22. Goldberg, D.M., E. Ng, A. Karumanchiri, E.P. Diamandis and G.J. Soleas. Resveratrol glucosides are important components of commercial wines. Am. J. Enol. Vitic. 47:415-420 (1996).
23. Goldberg, D. M., E. Ng, J. Van et al. Regional differences in resveratrol isomer concentrations of wines from various cultivars. J. Wine Res. 7:13-24 (1996).
24. Goldberg, D. M., G. J. Soleas, S. E. Hahn, et al. Identification and assay of trihydroxystilbenes in wine and their biological properties. In: Wine Composition and Health Benefits. T. Watkins (Ed.). pp 24-43. American Chemical Society, Washington (1997).
25. Goldberg, D. M., E. Tsang, A. Karumanchiri, et al. A method to assay the concentrations of phenolic constituents of biological interest in wines. Anal. Chem. 68:1688-1694 (1996).
26. Goldberg, D. M., J. Van, E. Ng, et al. A global survey of transresveratrol concentrations in commercial wines. Am. J. Enol. Vitic. 46:159-165 (1995).
27. Gorham, J. L. The stilbenoids. Progr. Phytochem. 6:203-252 (1980)
28. Graziani, Y., and R. Chayoth. 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).
29. Gronbaek, A. D., T. I. A. Sorensen, U. Becker, et al. Mortality associated with moderate intakes of wine, beer, or spirits. Br. Med. J. 310:1165-1169 (1995).
30. Gryglewski, R., R. Korbut, J. Robak, and J. Swies. On the mechanism of anti-thrombotic action of flavonoids. Biochem. Pharmacol. 36:317-322 (1987).
31. Gschwendt, M., F. Horn, W. Killestein, and I. Marks. Inhibition of the calcium and phospholipid-dependent protein kinase activity from mouse brain cytosol by quercetin. Biochem. Biophys. Res. Commun. 117:444-447 (1983).
32. Hasegawa, S., and V. P. Maier. Biosynthesis of trans-cinnamate from phenyl pyruvate and L-glutamate by cell-free extracts of grapefruit. Phytochemistry 9:2483-2490 (1970).
33. Hertog, M. G. L., P. C. H. Hollman, and P. van de Putte. Content of potentially anticarcinogenic flavonoids of tea infusions, wines, and fruit juices. J. Agric. Food Chem. 41:1242-1246 (1993).
34. Hoffman, J., H.,H. Fiebig, B.,R. Winterhalter, et al. Enhancement of the antiproliferative activity of c/s-diamminedichloroplatinum (II) by quercetin. Int. J. Cancer 45:536-539 (1990).
35. Hosokawa, N., Y. Hosokawa, T. Sakari, et al. Inhibitory effect of quercetin on the synthesis of a possible cell-cycle-related 17kDa protein in human colon cancer cells. Int. J. Cancer 45:1119-1124 (1990).
36. Hrazdina, G., G. G. Parsons, and L. R. Mattick. Physiological and biochemical events during development and maturation of grape berries. Am. J. Enol. Vitic. 35:220-227 (1984).
37. Igarashi, K., and M. Ohmuma. 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).
38. Ioku K., T. Tsushida, Y. Takei, et al. Antioxidative activity of quercetin and quercetin monoglucosides in solution and phospholipid bilayers. Biochim. Biophys. Acta 1234:99-104 (1995).
39. Jeandet, P., R. Bessis, B. F. Maume, and M. Sbaghi. Analysis of resveratrol in Burgundy wines. J. Wine Res. 4:79-85 (1993).
40. Kannel, W. B., and R. C. Ellison. Alcohol and coronary heart disease: the evidence for a protective effect. Clin. Chim. Acta 246:59-76 (1996).
41. Kanner, J., E. Frankel, R. Granit, et al. Natural antioxidants in grapes and wines. J. Agric. Food Chem. 42:64-69 (1994).
42. Klurfeld, D. M., and D. Kritchevsky. Differential effects of alcoholic beverages on experimental atherosclerosis in rabbits. Exp. Mol. Pathol., 34:62-71 (1981).
43. Kreuzaler, F., and K. Hahlbrock. 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).
44. Lamuela-Raventos, R. M., and A.L. Waterhouse. Occurrence of resveratrol in selected California wines by a new HPLC method. J. Agric. Food Chem., 41:521-523 (1993).
45. + adenosine triphosphatase and its partial reactions by quercetin. Biochemistry 15:4951-4958 (1974).
46. Laranjinha, J., O. Vieira, V. Madeira and L. Almeida. Two related phenolic antioxidants with opposite effects on Vitamin E content in low density lipoproteins oxidized by ferrylmyoglobin consumption vs regeneration. Arch. Biochem. Biophys. 323:373-381 (1995).
47. Laughton, M. J., B. Halliwell, and J. R. S. Hoult. Inhibition of flavonoids of lipid peroxidation, 5-lipoxygenase, and cyclo-oxygenase: Distinct structure-activity relationships. In: Flavonoids in Biology and Medicine III: Current Issues in Flavonoid Research, pp.245-249. National University of Singapore, Singapore (1990).
48. Levi, J., I. Teuerstein, M. Marbach, et al. Tyrosine protein kinase activity in the DMBA-induced rat mammary tumor: inhibition by quercetin. Biochem. Biophys. Res. Commun. 123:1224-1233 (1984).
49. 2 by quercetin. Inflammation 17:573-582 (1993).
50. Markaverich, B. M., R. R. Roberts, M. A. Alejandro, et al. Bioflavonoid interaction with rat uterine type II binding sites and cell growth inhibition. J. Steroid Biochem. 30:71-78 (1988).
51. Matter, W. F., R. F. Brown, and C. J. Vlahos. The inhibition of phosphatidylinositol 3-kinase by quercetin and analogues. Biochem. Biophys. Res. Commun. 186:624-631 (1992).
52. Melchior, F., and H. Kindl. Coordinate-and elicitor-dependent expression of stilbene synthase and phenylalanine ammonia-lyase genes in Vitis cv. optima. Arch. Biochem. Biophys. 288:552-557 (1991).
53. Ono, K., H. Nakane, M. Fukushima,et al. Differential inhibitory effects on the activities of reverse transcriptase and cellular DNA and RNA polymerases. Eur. J. Biochem. 190:469-476 (1990).
54. Pace-Asciak, C. R., S. Hahn, E. Diamandis, et al. 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).
55. Price, S. F., P. J. Breen, M. Valladao, et al. Cluster sun exposure and quercetin in Pinot Noir grapes and wine. Am. J. Enol. Vitic. 46:187-194 (1995).
56. Rimm, E. B., A. Klatsky, D. Grobbe, and M. J. Stampfer. 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).
57. Rizzo, M. T., and G. Weber, I-phosphotidylinositol 4-kinase: an enzyme linked with proliferation and malignancy. Cancer Res. 54:2611-2614 (1994).
58. Ruckstuhl, M., A. Beretz, R. Anton, and Y. Landry. Flavonoids are selective cyclic GMP phosphodiesterase inhibitors. Biochem. Pharmacol. 28:535-538 (1979).
59. Salagoïty-Auguste, M.-H., and A. Bertrand. Wine phenolics -Analysis of low molecular weight components by high performance liquid chromatography. J. Sci. Food Agric. 35:1241-1247 (1984).
60. Scambia, G., F. O. Ranelletti, P. Panici, 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).
61. Scambia, G., F. O. Ranelletti, P. P. Benedetti, 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).
62. Schroeder, J., F. Kreuzaler, E. Schafer, and K. Hahlbrock. Concomitant induction of phenylalanine ammonia-lyase and flavanone synthase mRNAs in irradiated plant cells. J. Biol. Chem. 254:57-65 (1979).
63. Seigneur, M., J. Bonnet, B. Dorian, 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).
64. 2+)-ATPase of sarcoplasmic reticulum. J. Biol. Chem. 256:887-892 (1981).
65. Siemann, E. H., and L. L. Creasy. Concentration of the phyloalexin resveratrol in wine. Am. J. Enol. Vitic. 43:49-52 (1992).
66. Spanos, G. A., and R. E. Wrolstad. Influence of processing and storage on the phenolic composition of Thompson seedless grape juice. J. Agric. Food Chem. 38:1565-1571 (1990).
67. Stavric B. Quercetin in our diet: From potent mutagen to a probable anticarcinogen. Clin. Biochem. 27:245-248 (1994).
68. St. Leger, A. S., A. L. Cochrane, and F. Moore. Factors associated with cardiac mortality in developed countries with particular reference to the consumption of wine. Lancet 1:1017-1020 (1979).
69. Suolinna, E. M., R. N. Buchsbaum, and E. Racker. The effect of flavonoids on aerobic glycolysis and growth of tumor cells. Cancer Res. 35:1865-1872 (1975).
70. Teissedre, P. L., E. N. Frankel, A. L. Waterhouse, et al. Inhibition of in vitro human LDL oxidation by phenolic antioxidants from grapes and wines. J. Sci. Food Agric. 70:55-61 (1996).
71. Teofili, L., L. Pierelli, M. S. Iovino et al. The combination of quercetin and cytosine arabinoside synergistically inhibits leukemic cell growth. Leuk. Res. 16:497-503 (1992).
72. Terao, J., M. Piskula, and Q. Yao. Protective effect of epicatechin, epicatechin gallate, and quercetin on lipid peroxidation in phospholipid bilayers. Arch. Biochem. Biophys. 308:278-284 (1994).
73. Uddin, S., and M. A. Choudhry. Quercetin, a bioflavonoid, inhibits the DNA synthesis of human leukemia cells. Biochem. Mol. Biol. Int. 36:545-550 (1995).
74. Wei, Y., X. Zhao, Y. Kariya, et al. Induction of apoptosis by quercetin: involvement of heat shock protein. Cancer Res. 4952-4957 (1994).
75. Yanagihara, K., A. Ito, T. Toge, and M. Numoto. Antiproliferative effects of isoflavones on human cancer cell lines established from the gastrointestinal tract. Cancer Res. 53:5815-5821 (1993).
76. Yoshida, M., T. Sakai, N. Hosokawa, et al. The effect of quercetin on cell cycle progression and growth of human gastric cancer cells. FEBS Lett. 260:10-13 (1990).
77. 1 phase of the cell cycle. Cancer Res. 52:6676-6681 (1992).
78. Yutin, C., Z. Ronglian, J. Zhongjian, and J. Yong. Flavonoids as superoxide scavengers and antioxidants. Free Radic. Biol. Med. 9:19-21 (1990).