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Volumn 91, Issue 6, 2004, Pages 1213-1219

Characterisation of metabolites of the putative cancer chemopreventive agent quercetin and their effect on cyclo-oxygenase activity

Author keywords

Cancer chemoprevention; Cyclo oxygenase; Metabolism; Quercetin

Indexed keywords

CYCLOOXYGENASE 2; GLUTATHIONE; ISORHAMNETIN; PROSTAGLANDIN E2; PROSTAGLANDIN SYNTHASE; QUERCETIN; QUERCETIN 3 O SULFATE; QUERCETIN 7 O SULFATE; QUERCETIN DERIVATIVE; RUTOSIDE; TAMARIXETIN; UNCLASSIFIED DRUG;

EID: 5044232069     PISSN: 00070920     EISSN: None     Source Type: Journal    
DOI: 10.1038/sj.bjc.6602091     Document Type: Article
Times cited : (51)

References (48)
  • 1
    • 0034108013 scopus 로고    scopus 로고
    • Unavailability and metabolism of the flavonol quercetin in the pig
    • Ader P, Wessmann A, Wolffram S (2000) Unavailability and metabolism of the flavonol quercetin in the pig. Free Radic Biol Med 28: 1056-1067
    • (2000) Free Radic Biol Med , vol.28 , pp. 1056-1067
    • Ader, P.1    Wessmann, A.2    Wolffram, S.3
  • 3
    • 0034660208 scopus 로고    scopus 로고
    • Peroxidase-catalyzed formation of quercetin quinone methide - Glutathione adducts
    • Awad HM, Boersma MG, Vervoort J, Rietjens IMCM (2000) Peroxidase-catalyzed formation of quercetin quinone methide - glutathione adducts. Arch Biochem Biophys 378: 224-233
    • (2000) Arch Biochem Biophys , vol.378 , pp. 224-233
    • Awad, H.M.1    Boersma, M.G.2    Vervoort, J.3    Rietjens, I.M.C.M.4
  • 5
    • 0000823220 scopus 로고
    • Metabolic fate of rutin and quercetin in the animal body
    • Booth AN, Murray CW, Jones FT, DeEds F (1956) Metabolic fate of rutin and quercetin in the animal body. J Biol Chem 233: 251-257
    • (1956) J Biol Chem , vol.233 , pp. 251-257
    • Booth, A.N.1    Murray, C.W.2    Jones, F.T.3    DeEds, F.4
  • 6
    • 0031417558 scopus 로고    scopus 로고
    • Formation of catechol estrogen glutathione conjugates and gamma-glutamyl transpeptidase-dependent nephrotoxicity of 17 beta-estradiol in the golden Syrian hamster
    • Butterworth M, Lau SS, Monks TJ (1997) Formation of catechol estrogen glutathione conjugates and gamma-glutamyl transpeptidase-dependent nephrotoxicity of 17 beta-estradiol in the golden Syrian hamster. Carcinogenesis 18: 561-567
    • (1997) Carcinogenesis , vol.18 , pp. 561-567
    • Butterworth, M.1    Lau, S.S.2    Monks, T.J.3
  • 8
    • 1442278713 scopus 로고    scopus 로고
    • Hepatotoxicity of 3,4-methylenedioxyamphetamine and alpha-methyldopamine in isolated rat hepatocytes: Formation of glutathione conjugates
    • Carvalho M, Milhazes N, Remiao F, Borges F, Fernandes E, Amado F, Monks TJ, Carvalho F, Bastos ML (2004) Hepatotoxicity of 3,4-methylenedioxyamphetamine and alpha-methyldopamine in isolated rat hepatocytes: formation of glutathione conjugates. Arch Toxicol 78: 16-24
    • (2004) Arch Toxicol , vol.78 , pp. 16-24
    • Carvalho, M.1    Milhazes, N.2    Remiao, F.3    Borges, F.4    Fernandes, E.5    Amado, F.6    Monks, T.J.7    Carvalho, F.8    Bastos, M.L.9
  • 9
    • 0032479204 scopus 로고    scopus 로고
    • Quercetin metabolites inhibit copper ion-induced lipid peroxidation in rat plasma
    • Da Silva EL, Piskula MK, Yamamoto N, Moon JH, Terao J (1998) Quercetin metabolites inhibit copper ion-induced lipid peroxidation in rat plasma. FEBS Let 430: 405-408
    • (1998) FEBS Let , vol.430 , pp. 405-408
    • Da Silva, E.L.1    Piskula, M.K.2    Yamamoto, N.3    Moon, J.H.4    Terao, J.5
  • 10
    • 0034672514 scopus 로고    scopus 로고
    • Conjugation position of quercetin glucuronides and effect on biological activity
    • Day AJ, Bao, YP, Morgan MRA, Williamson G (2000) Conjugation position of quercetin glucuronides and effect on biological activity. Free Radic Biol Med 29: 1234-1243
    • (2000) Free Radic Biol Med , vol.29 , pp. 1234-1243
    • Day, A.J.1    Bao, Y.P.2    Morgan, M.R.A.3    Williamson, G.4
  • 12
    • 5044231153 scopus 로고
    • Formation of protocatechuic acid from quercetin by rat kidney in vitro
    • Douglass CD, Hogan R (1958) Formation of protocatechuic acid from quercetin by rat kidney in vitro. J Biol Chem 230: 625-629
    • (1958) J Biol Chem , vol.230 , pp. 625-629
    • Douglass, C.D.1    Hogan, R.2
  • 13
    • 77957178533 scopus 로고
    • Toxicity and carcinogenicity studies of quercetin, a natural component of foods
    • Dunnick JK, Hailey JR (1992) Toxicity and carcinogenicity studies of quercetin, a natural component of foods. Fund Appl Toxicol 19: 423-431
    • (1992) Fund Appl Toxicol , vol.19 , pp. 423-431
    • Dunnick, J.K.1    Hailey, J.R.2
  • 14
    • 0014939358 scopus 로고
    • Physiochemical and kinetic properties of mushroom tyrosinase
    • Duckworth HW, Coleman JE (1970) Physiochemical and kinetic properties of mushroom tyrosinase. J Biol Chem 245: 1613-1625
    • (1970) J Biol Chem , vol.245 , pp. 1613-1625
    • Duckworth, H.W.1    Coleman, J.E.2
  • 16
    • 0029610477 scopus 로고
    • Review of the biology of quercetin and related bioflavonoids
    • Formica JV, Regelson W (1995) Review of the biology of quercetin and related bioflavonoids. Food Chem Toxicol 33: 1061-1080
    • (1995) Food Chem Toxicol , vol.33 , pp. 1061-1080
    • Formica, J.V.1    Regelson, W.2
  • 17
    • 0013909023 scopus 로고
    • Quantitative comparison of toxicity of anticancer agents in mouse, rat, hamster, dog, monkey, and man
    • Freireich EJ, Gehan EA, Rall DP, Schmidt LH, Skipper HE (1966) Quantitative comparison of toxicity of anticancer agents in mouse, rat, hamster, dog, monkey, and man. Cancer Chemother Rep 50: 219-244
    • (1966) Cancer Chemother Rep , vol.50 , pp. 219-244
    • Freireich, E.J.1    Gehan, E.A.2    Rall, D.P.3    Schmidt, L.H.4    Skipper, H.E.5
  • 18
    • 0035865879 scopus 로고    scopus 로고
    • Peroxidative metabolism of apigenin and naringenin vs luteplin and quercetin: Glutathione oxidation and conjugation
    • Galati G, Moridani MY, Chan TS, O'Brien PJ (2001) Peroxidative metabolism of apigenin and naringenin vs luteplin and quercetin: glutathione oxidation and conjugation. Free Radic Biol Med 30: 370-382
    • (2001) Free Radic Biol Med , vol.30 , pp. 370-382
    • Galati, G.1    Moridani, M.Y.2    Chan, T.S.3    O'Brien, P.J.4
  • 19
    • 0142243190 scopus 로고    scopus 로고
    • Commentary: Relationship between mechanisms, bioavailibility and preclinical chemopreventive efficacy of resveratrol: A conundrum
    • Gescher AJ, Steward WP (2003) Commentary: relationship between mechanisms, bioavailibility and preclinical chemopreventive efficacy of resveratrol: a conundrum. Cancer Epidemiol Biomarkers Prev 12: 953-957
    • (2003) Cancer Epidemiol Biomarkers Prev , vol.12 , pp. 953-957
    • Gescher, A.J.1    Steward, W.P.2
  • 20
    • 0016811010 scopus 로고
    • Disposition of quercetin in man after single oral and intravenous doses
    • Gugler R, Leschik M, Dengler HJ (1975) Disposition of quercetin in man after single oral and intravenous doses. Eur J Clin Pharmacol 9: 229-234
    • (1975) Eur J Clin Pharmacol , vol.9 , pp. 229-234
    • Gugler, R.1    Leschik, M.2    Dengler, H.J.3
  • 21
    • 33751391867 scopus 로고
    • Content of potentially anticarcinogenic flavonoids of 28 vegetables and 19 fruits commonly consumed in the Netherlands
    • Hertog MGL, Hollman PCH, Katan MB (1992) Content of potentially anticarcinogenic flavonoids of 28 vegetables and 19 fruits commonly consumed in the Netherlands. J Agr Food Chem 40: 2379 -2383
    • (1992) J Agr Food Chem , vol.40 , pp. 2379-2383
    • Hertog, M.G.L.1    Hollman, P.C.H.2    Katan, M.B.3
  • 22
    • 0027504187 scopus 로고
    • Dietary antioxidant flavonoids and risk of coronary heart disease - The Zutphen elderly study
    • Hertog MGL, Feskens EJM, Hollman PCH, Katan MB, Kromhout D (1993) Dietary antioxidant flavonoids and risk of coronary heart disease - the Zutphen elderly study. Lancet 342: 1007-1011
    • (1993) Lancet , vol.342 , pp. 1007-1011
    • Hertog, M.G.L.1    Feskens, E.J.M.2    Hollman, P.C.H.3    Katan, M.B.4    Kromhout, D.5
  • 25
    • 0030021661 scopus 로고    scopus 로고
    • Potential health-effects of the dietary flavonol quercetin
    • Hertog MGL, Hollman PCH (1996) Potential health-effects of the dietary flavonol quercetin. Eur J Clin Nutr 50: 63-71
    • (1996) Eur J Clin Nutr , vol.50 , pp. 63-71
    • Hertog, M.G.L.1    Hollman, P.C.H.2
  • 26
    • 0030775534 scopus 로고    scopus 로고
    • Absorption, metabolism and health effects of dietary flavonoids in man
    • Hollman PCH, Katan MB (1997) Absorption, metabolism and health effects of dietary flavonoids in man. Biomed Pharmacother 51: 305-310
    • (1997) Biomed Pharmacother , vol.51 , pp. 305-310
    • Hollman, P.C.H.1    Katan, M.B.2
  • 27
    • 0029924611 scopus 로고    scopus 로고
    • Bioactivation of estrone and its catechol metabolites to quinoid-glutathione conjugates in rat liver microsomes
    • Iverson SL, Shen L, Anlar N, Bolton JL (1996) Bioactivation of estrone and its catechol metabolites to quinoid-glutathione conjugates in rat liver microsomes. Chem Res Toxicol 9: 492-499
    • (1996) Chem Res Toxicol , vol.9 , pp. 492-499
    • Iverson, S.L.1    Shen, L.2    Anlar, N.3    Bolton, J.L.4
  • 28
    • 0031806472 scopus 로고    scopus 로고
    • Determination of quercetin in human plasma by HPLC with spectrophotometric or electrochemical detection
    • Jones DJL, Lim CK, Ferry DR, Gescher A (1998) Determination of quercetin in human plasma by HPLC with spectrophotometric or electrochemical detection. Biomed Chromatogr 12: 232-235
    • (1998) Biomed Chromatogr , vol.12 , pp. 232-235
    • Jones, D.J.L.1    Lim, C.K.2    Ferry, D.R.3    Gescher, A.4
  • 29
    • 0029868401 scopus 로고    scopus 로고
    • Dietary flavonoids, antioxidant vitamins, and incidence of stroke - The Zutphen study
    • Keli SO, Hertog MGL, Feskens EJM, Kromhout D (1996) Dietary flavonoids, antioxidant vitamins, and incidence of stroke - the Zutphen study. Arch Intern Med 156: 637-642
    • (1996) Arch Intern Med , vol.156 , pp. 637-642
    • Keli, S.O.1    Hertog, M.G.L.2    Feskens, E.J.M.3    Kromhout, D.4
  • 31
    • 0018079525 scopus 로고
    • Mutagenicity of plant flavonoids: Structural requirements for mutagenic activity in Salmonella typhimurium
    • MacGregor JT, Jurd L (1978) Mutagenicity of plant flavonoids: Structural requirements for mutagenic activity in Salmonella typhimurium. Mutat Res 54: 297-309
    • (1978) Mutat Res , vol.54 , pp. 297-309
    • MacGregor, J.T.1    Jurd, L.2
  • 33
    • 0032562766 scopus 로고    scopus 로고
    • Quercetin is recovered in human plasma as conjugated derivatives which retain antioxidant properties
    • Manach C, Morand C, Crespy V, Demigne C, Texier O, Regerat F, Remesy C (1998) Quercetin is recovered in human plasma as conjugated derivatives which retain antioxidant properties. FEBS Lett 426: 331-336
    • (1998) FEBS Lett , vol.426 , pp. 331-336
    • Manach, C.1    Morand, C.2    Crespy, V.3    Demigne, C.4    Texier, O.5    Regerat, F.6    Remesy, C.7
  • 35
    • 0029742815 scopus 로고    scopus 로고
    • Radical scavenger activity of 3 flavonoid metabolites studied by inhibition of chemiluminescence in human PMNs
    • Merfort I, Heilmann J, Weiss M, Pietta P, Gardana C (1996) Radical scavenger activity of 3 flavonoid metabolites studied by inhibition of chemiluminescence in human PMNs. Planta Med 62: 289-292
    • (1996) Planta Med , vol.62 , pp. 289-292
    • Merfort, I.1    Heilmann, J.2    Weiss, M.3    Pietta, P.4    Gardana, C.5
  • 37
    • 0033867003 scopus 로고    scopus 로고
    • Suppression by flavonoids of cyclooxygenase-2 promoter-dependent transcriptional activity in colon cancer cells: Structure - Activity relationship
    • Mutoh H, Takahashi M, Fukuda K, Komatsu H, Enya T, Matsushima-Hibiya Y, Sugimura T, Wakabayashi K (2000) Suppression by flavonoids of cyclooxygenase-2 promoter-dependent transcriptional activity in colon cancer cells: structure - activity relationship. Jpn J Cancer Res 91: 686-691
    • (2000) Jpn J Cancer Res , vol.91 , pp. 686-691
    • Mutoh, H.1    Takahashi, M.2    Fukuda, K.3    Komatsu, H.4    Enya, T.5    Matsushima-Hibiya, Y.6    Sugimura, T.7    Wakabayashi, K.8
  • 38
    • 0027433751 scopus 로고
    • Induction of rat hepatic and intestinal glutathione S-transferases and glutathione by dietary naturally-occurring anticarcinogens
    • Nijhoff W, Groen AGM, Peters WHM (1993) Induction of rat hepatic and intestinal glutathione S-transferases and glutathione by dietary naturally-occurring anticarcinogens. Int J Oncol 3: 1131-1139
    • (1993) Int J Oncol , vol.3 , pp. 1131-1139
    • Nijhoff, W.1    Groen, A.G.M.2    Peters, W.H.M.3
  • 40
    • 0031427713 scopus 로고    scopus 로고
    • Cytotoxicity and cell-proliferation induced by the nephrocarcinogen hydroquinone and its nephrotoxic metabolite 2,3,5-(tris-glutathion-S-yl) hydroquinone
    • Peters MMCG, Jones TW, Monks TJ, Lau SS (1997) Cytotoxicity and cell-proliferation induced by the nephrocarcinogen hydroquinone and its nephrotoxic metabolite 2,3,5-(tris-glutathion-S-yl)hydroquinone. Carcinogenesis 18: 2393-2401
    • (1997) Carcinogenesis , vol.18 , pp. 2393-2401
    • Peters, M.M.C.G.1    Jones, T.W.2    Monks, T.J.3    Lau, S.S.4
  • 42
    • 0000756228 scopus 로고    scopus 로고
    • Quercetin's solubility affects its accumulation in rat plasma after oral administration
    • Piskula MK, Terao J (1998) Quercetin's solubility affects its accumulation in rat plasma after oral administration. J Agric Food Chem 46: 4313-4317
    • (1998) J Agric Food Chem , vol.46 , pp. 4313-4317
    • Piskula, M.K.1    Terao, J.2
  • 43
    • 0035846885 scopus 로고    scopus 로고
    • Inhibition of inducible nitric oxide synthase and cyclooxygenase-2 expression by flavonoids in macrophage J774A.1
    • Raso GM, MeIi R, Di Carlo G, Pacilio M, Di Carlo R (2001) Inhibition of inducible nitric oxide synthase and cyclooxygenase-2 expression by flavonoids in macrophage J774A.1. Life Sci 68: 921-931
    • (2001) Life Sci , vol.68 , pp. 921-931
    • Raso, G.M.1    MeIi, R.2    Di Carlo, G.3    Pacilio, M.4    Di Carlo, R.5
  • 44
    • 0030010582 scopus 로고    scopus 로고
    • Prooxidant activity of flavonoids - Effects on glutathione and glutathione-S-transferase in isolated rat-liver nuclei
    • Sahu SC, Gray GC (1996) Prooxidant activity of flavonoids - effects on glutathione and glutathione-S-transferase in isolated rat-liver nuclei. Cancer Lett 104: 193-196
    • (1996) Cancer Lett , vol.104 , pp. 193-196
    • Sahu, S.C.1    Gray, G.C.2
  • 45
    • 0025874444 scopus 로고
    • Sulphation of the flavonoids quercetin and catechin by rat-liver
    • Shali NA, Curtis CG, Powell GM, Roy AB (1991) Sulphation of the flavonoids quercetin and catechin by rat-liver. Xenobiotica 21: 881 -893
    • (1991) Xenobiotica , vol.21 , pp. 881-893
    • Shali, N.A.1    Curtis, C.G.2    Powell, G.M.3    Roy, A.B.4
  • 47
    • 0020644145 scopus 로고
    • Metabolic-fate of [C-14] quercetin in the ACl rat
    • Ueno I, Nakano N, Hirono I (1983) Metabolic-fate of [C-14] quercetin in the ACl rat. Jpn J Exp Med 53: 41-50
    • (1983) Jpn J Exp Med , vol.53 , pp. 41-50
    • Ueno, I.1    Nakano, N.2    Hirono, I.3


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