Quercetin Metabolites Downregulate Cydooxygenase-2 Transcription in Human Lymphocytes Ex Vivo but Not in Vivo

Journal of Nutrition

Volumn 134, Issue 3, 2004, Pages 552-557

  De Pascual Teresa, Sonia ^a,d   Johnston, Kelly L ^b   DuPont, M Susan ^a   O'Leary, Karen A ^a   Needs, Paul W ^a   Morgan, Linda M ^b   Clifford, Mike N ^b   Bao, Yongping ^a   Williamson, Gary ^c  

^a INSTITUTE OF FOOD RESEARCH   (United Kingdom)

^b UNIVERSITY OF SURREY   (United Kingdom)

^c NESTLÉ RESEARCH CENTER   (Switzerland)

^d INSTITUTO DEL FRÍO CSIC   (Spain)

Author keywords

Cyclooxgenase 2; Flavonoids; Gene expression; Lymphocyte; Quercetin metabolites

Indexed keywords

3' METHYLQUERCETIN 3 GLUCURONIDE; CYCLOOXYGENASE 2; MESSENGER RNA; QUERCETIN 3 GLUCURONIDE; QUERCETIN 3' SULFATE; QUERCETIN DERIVATIVE; UNCLASSIFIED DRUG;

ADULT; ARTICLE; BLOOD LEVEL; CLINICAL TRIAL; CONTROLLED CLINICAL TRIAL; CONTROLLED STUDY; CROSSOVER PROCEDURE; DIETARY INTAKE; DOWN REGULATION; FEMALE; GENE EXPRESSION; HUMAN; HUMAN CELL; HUMAN EXPERIMENT; INFLAMMATION; LYMPHOCYTE; MALE; NORMAL HUMAN; ONION; PROTEIN EXPRESSION; RANDOMIZED CONTROLLED TRIAL; REAL TIME POLYMERASE CHAIN REACTION; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; SINGLE BLIND PROCEDURE; TEST MEAL; TRANSCRIPTION REGULATION;

ALLIUM CEPA;

EID: 1542286868     PISSN: 00223166     EISSN: None     Source Type: Journal    
DOI: 10.1093/jn/134.3.552     Document Type: Article

References (46)

1. World Cancer Research Fund (1997) Food, Nutrition and The Prevention of Cancer, A Global Perspective. American Institute for Cancer Research, Washington, DC.
2. Gupta, K. & Panda, D. (2002) Perturbation of microtubule polymerization by quercetin through tubulin binding: a novel mechanism of its antiproliferative activity. Biochemistry 41: 13029-13038.
3. Wadsworth, T. L., McDonald, T. L. & Koop, D. R. (2001) Effects of Ginkgo biloba extract (EGb 761) and quercetin on lipopolysaccharide-induced signaling pathways involved in the release of tumor necrosis factor-alpha. Biochem. Pharmacol. 62: 963-974.
4. Amin, A. R., Attur, M., Patel, R. N., Thakker, G. D., Marshall, P. J., Rediske, J., Stuchin, S. A., Patel, I. R. & Abramson, S. B. (1997) Superinduction of cyclooxygenase-2 activity in human osteoarthritis-affected cartilage. Influence of nitric oxide. J. Clin. Investig. 99: 1231-1237.
5. Anderson, G. D., Hauser, S. D., McGarity, K. L., Bremer, M. E., Isakson, P. C. & Gregory, S.A. (1996) Selective inhibition of cyclooxygenase (COX)-2 reverses inflammation and expression of COX-2 and interleukin 6 in rat adjuvant arthritis. J. Clin. Investig. 97: 2672-2679.
6. Hernandez, G. L., Volpert, O. V., Iñiguez, M. A., Lorenzo, E., Martinez-Martinez, S., Grau, R., Fresno, M. & Redondo, J. M. (2001) Selective inhibition of vascular endothelial growth factor-mediated angiogenesis by cyclosporin A: roles of the nuclear factor of activated T cells and cyclooxygenase 2. J. Exp. Med. 193: 607-620.
7. Molina, M. A., Sitja-Arnau, M., Lemoine, M. G., Frazier, M. L. & Sinicrope, F. A. (1999) Increased cyclooxygenase-2 expression in human pancreatic carcinomas and cell lines: growth inhibition by nonsteroidal anti-inflammatory drugs. Cancer Res. 59: 4356-4362.
8. Yip-Schneider, M. T., Barnard, D. S., Billings, S. D., Cheng, L., Heilman, D. K., Lin, A., Marshall, S. J., Crowell, P. L., Marshall, M. S. & Sweeney, C. J. (2000) Cyclooxygenase-2 expression in human pancreatic adenocarcinomas. Carcinogenesis 21: 139-146.
9. Sun, Y., Tang, X. M., Half, E., Kuo, M. T. & Sinicrope, F. A. (2002) Cyclooxygenase-2 overexpression reduces apoptotic susceptibility by inhibiting the cytochrome c-dependent apoptotic pathway in human colon cancer cells. Cancer Res. 62: 6323-6328.
10. Maier, J., Hia, T. & Maciag, T. (1990) Cyclooxygenase is an immediate early gene induced by interleukin-1 in human endothelial cells. J. Biol. Chem. 265: 10805-10808.
11. Notoya, K., Jovanovic, D. V., Reboul, P., Martel-Pelletier, J., Mineau, F. & Pelletier, J. P. (2000) The induction of cell death in human osteoarthritis chondrocytes by nitric oxide is related to the production of prostaglandin E2 via the induction of cyclooxygenase-2. J. Immunol. 165: 3402-3410.
12. O'Banion, M. K., Winn, V. D. & Young, D. A. (1992) cDNA cloning and functional activity of a glucocorticoid-regulated inflammatory cyclooxygenase. Proc. Natl. Acad. Sci. U.S.A. 89: 4888-4892.
13. Pablos, J. L., Santiago, B., Carreira, P. E., Galindo, M. & Gomez-Reino, J. J. (1999) Cyclooxygenase-1 and -2 are expressed by human T cells. Clin. Exp. Immunol. 115: 86-90.
14. Di Popolo, A., Memoli, A., Apicella, A., Tuccillo, C., di Palma, A., Ricchi, P., Acquaviva, A. M. & Zarrilli, R. (2000) IGF-II/IGF-I receptor pathway upregulates COX-2 mRNA expression and PGE2 synthesis in Caco-2 human colon carcinoma cells. Oncogene 19: 5517-5524.
15. Krishnamachari, V., Levine, L. H., & Pare, P. W. (2002) Flavonoid oxidation by the radical generator AIBN: a unified mechanism for quercetin radical scavenging. J. Agric. Food Chem. 50: 4357-4363.
16. Day, A. J., Bao, Y. P., Morgan, M. R. & Williamson, G. (2000) Conjugation position of quercetin glucuronides and effect on biological activity. Free Radic. Biol. Med. 29:1234-1243.
17. Wurm, G., Baumann, J. & Geres, U. (1982) Beeinflussung des arachidonsaurestoffweshsels durch flavonides. Dtsch. Apoth. Ztg. 122: 2062-2068.
18. Baumann, J., Bruchhausen, F. V. & Wurm, G. (1982) Flavonoids and related compounds as inhibitors of arachidonic acid peroxidation. Prostaglandins 20:627-639.
19. Banerjee, T., Van der Vliet, A. & Ziboh, V. A. (2002) Downregulation of COX-2 and iNOS by amentoflavone and quercetin in A549 human lung adenocarcinoma cell line. Prostaglandins Leukot. Essent. Fatty Acids 66: 485-492.
20. Mutoh, M., Takashahi, M., Fukuda, K., Komatsu, H., Erija, T., Matsushima-Hibiya, Y., Mutoh, H., Sugimurs, T. & Wakabayashi, K. (2000) Suppression by the flavonoids of cyclooygenase-2 promoter-dependent transcriptional activity in colon cancer cells: structure activity relationship. Jpn. J. Cancer Res. 91: 686-691.
21. Day, A. J., Mellon, F., Barron, D., Sarrazin, G., Morgan, M. R. & Williamson, G. (2001) Human metabolism of dietary flavonoids: identification of plasma metabolites of quercetin. Free Radic. Res. 35: 941-952.
22. Graefe, E. U., Derendorf, H. & Veit, M. (1999) Pharmacokinetics and bioavailability of the flavonol quercetin in humans. Int. J. Clin. Pharmacol. Ther. 37:219-233.
23. O'Leary, K. A., Day, A. J., Needs, P. W., Mellon, F. A., O'Brien, N. M. & Williamson, G. (2003) Metabolism of quercetin-7- and quercetin-3-glucuronides by an in vitro hepatic model: the role of human beta-glucuronidase, sulfotransferase, catechol-O-methyltransferase and multi-resistant protein 2 (MRP2) in flavonoid metabolism. Biochem. Pharmacol. 65: 479-491.
24. Rice-Evans, C. A., Miller, N. J. & Paganga, G. (1996) Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic. Biol. Med. 20: 933-956.
25. Price, K. R., Colquhoun, I. J., Barnes, K. A. & Rhodes, M. J. C. (1998) Composition and content of flavonol glycosides in green beans and their fate during processing. J. Agric. Food Chem. 46: 4898-4903.
26. Jurd, L. (1962) The selective alkylation of polyphenols, II. Methylation of 7-, 4′-, and 3′-hydroxyl groups in flavonols. J. Org. Chem. 27: 1294-1297.
27. Brown, R. T., Scheinmann, F. & Stachulski, A. V. (1997) Intermediates for glucuronide synthesis: 7-hydroxycoumarin glucuronide. J. Chem. Res. (suppl.): 370-371.
28. Needs P. W. & Williamson G. (2001) Syntheses of daidzein-7-yl/β -D-glucopyranosiduronic acid and daidzein-4′, 7-yl di-β -D-glucopyranosiduronic acid. Carbohydr. Res. 330: 511-515.
29. Sullivan, D. M. and Carpenter, D. E. (1993) Methods of Analysis for Nutrition Labeling, AOAC International, Arlington, VA.
30. Ministerio de Agricultura, P. y. A. (1994) Metodos Oficiales de Analisis, Servicio de Publicaciones del Ministerio Agricultura, Pesca y Alimentacion, Madrid, Spain.
31. Petri, N., Tannergren, C., Holst, B., Mellon, F. A., Bao, Y., Plumb, G. W., Bacon, J., O'Leary, K. A., Kroon, P. A., Knutson, L., Forsell, P., Eriksson, T., Lennernas, H. & Williamson, G. (2003) Absorption/metabolism of sulforaphane and quercetin, and regulation of phase II enzymes, in human jejunum in vivo. Drug Metab. Dispos. 31: 805-813.
32. Graefe, E. U., Wittig, J., Mueller, S., Riethling, A. K., Uehleke, B., Drewelow, B., Pforte, H., Jacobasch, G., Derendorf, H. & Veit, M. (2001) Pharmacokinetics and bioavailability of quercetin glycosides in humans. J. Clin. Pharmacol. 41: 492-499.
33. Belton, O., Byrne, D., Kearney, D., Leahy, A. & Fitzgerald, D. J. (2000) Cyclooxygenase-1 and -2-dependent prostacyclin formation in patients with atherosclerosis. Circulation 102: 840-845.
34. Schonbeck, U., Sukhova, G. K., Graber, P., Coulter, S. & Libby, P. (1999) Augmented expression of cyclooxygenase-2 in human atherosclerotic lesions. Am. J. Pathol. 155: 1281-1291.
35. Nasir, A., Fernandez, P. M., Chughtai, O. R. & Kaiser, H. E. (2002) COX-2, NSAIDs and human neoplasia. Part I: Colorectal neoplasms. In Vivo 16: 501-509.
36. Dooper, M. M., Wassink, L., M'Rabet, L. & Graus, Y. M. (2002) The modulatory effects of prostaglandin-E on cytokine production by human peripheral blood mononuclear cells are independent of the prostaglandin subtype. Immunology 107: 152-159.
37. de Vries, J. H., Hollman, P. C., Meyboom, S., Buysman, M. N., Zock, P. L., van Staveren, W. A. & Katan, M.B. (1998) Plasma concentrations and urinary excretion of the antioxidant flavonols quercetin and kaempferol as biomarkers for dietary intake. Am. J. Clin. Nutr. 68: 60-65.
38. Erlund, I., Kosonen, T., Alfthan, G., Maenpaa, J., Perttunen, K., Kenraali, J., Parantainen, J. & Aro, A. (2000) Pharmacokinetics of quercetin from quercetin aglycone and rutin in healthy volunteers. Eur. J. Clin. Pharmacol. 56: 545-553.
39. Hollman, P. C., van Trijp, J. M., Buysman, M. N., van der Gaga, M. S., Mengelers, M. J., de Vries, J. H. & Katan, M.B. (1997) Relative bioavailability of the antioxidant flavonoid quercetin from various foods in man. FEBS Lett. 418: 152-156.
40. Meydani, S. N., Barklund, M. P., Liu, S., Meydani, M., Millar, R. A., Cannon, J. G., Morrow, F. D., Rocklin, R. & Blumberg, J. B. (1990) Vitamin E supplementation enhances cell-mediated immunity in healthy elderly subjects. Am. J. Clin. Nutr. 52: 557-563.
41. Wu, D., Hayek, M. G., & Meydani, S. (2001) Vitamin E and macrophage cyclooxygenase regulation in the aged. J. Nutr. 131: 382S-388S.
42. Guerrero, M. F., Puebla, P., Carron, R., Martin, M. L. & San Roman, L. (2002) Quercetin 3, 7-dimethyl ether: a vasorelaxant flavonoid isolated from Croton schiedeanus Schlecht. J. Pharm. Pharmacol. 54:1373-1378.
43. Calkin, A. C., Sudhir, K., Honisett, S., Williams, M. R., Dawood, T. & Komesaroff, P. A. (2002) Rapid potentiation of endothelium-dependent vasodilation by estradiol in postmenopausal women is mediated via cyclooxygenase 2. J. Clin. Endocrinol. Metab. 87: 5072-5075.
44. de Santi, C., Pietrabissa, A., Mosca, F. & Pacifici, G. M. (2002) Methylation of quercetin and fisetin, flavonoids widely distributed in edible vegetables, fruits and wine, by human liver. Int. J. Clin. Pharmacol. Ther. 40: 207-212.
45. Manach, C., Morand, C., Texier, O., Favier, M. L., Agullo, G., Demigné, C., Regerat, F. & Rémésy, C. (1995) Quercetin metabolites in plasma of rats fed diets containing rutin or quercetin. J. Nutr. 125: 1911-1922.
46. Schultz, E. (1991) Catechol-O-methyltransferase and aromatic L-amino acid decarboxylase activities in human gastrointestinal tissues. Life Sci. 49: 721-725.