메뉴 건너뛰기




Volumn 36, Issue 4, 2006, Pages 269-285

Effect of natural analogues of trans-resveratrol on cytochromes P4501A2 and 2E1 catalytic activities

Author keywords

Chemoprevention; CYP1A2; CYP2E1; Stilbene derivatives; Trans resveratrol

Indexed keywords

3,4' DIHYDROXY 5 METHOXYSTILBENE; 3,5 DIHYDROXY 4' METHOXYSTILBENE; 4 NITROPHENOL; 4 NITROPHENOL HYDROXYLASE; CYTOCHROME P450 1A2; CYTOCHROME P450 2E1; ETHOXYRESORUFIN DEETHYLASE; FUNCTIONAL GROUP; HYDROXYL GROUP; METHOXY GROUP; OXYGENASE; PICEATANNOL; PTEROSTILBENE; RESVERATROL; RESVERATROL DERIVATIVE; RESVERATROL TRIMETHYL ETHER; STILBENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33646767096     PISSN: 00498254     EISSN: 13665928     Source Type: Journal    
DOI: 10.1080/00498250500485057     Document Type: Article
Times cited : (34)

References (54)
  • 1
    • 0031687374 scopus 로고    scopus 로고
    • Inhibition of murine hepatic cytochrome P450 activities by natural and synthetic phenolic compounds
    • Baer-Dubowska W, Szaefer H, Krajka-Kuźniak V. 1998. Inhibition of murine hepatic cytochrome P450 activities by natural and synthetic phenolic compounds. Xenobiotica 28:735-743.
    • (1998) Xenobiotica , vol.28 , pp. 735-743
    • Baer-Dubowska, W.1    Szaefer, H.2    Krajka-Kuźniak, V.3
  • 2
    • 0022357068 scopus 로고
    • Ethoxy-, pentoxy- and benzyloxyphenoxazones and homologues: A series of substrates to distinguish between different induced cytochromes P-450
    • Burke MD, Thompson S, Elcombe CR, Halpert J, Haaparanta T, Mayer RT. 1985. Ethoxy-, pentoxy- and benzyloxyphenoxazones and homologues: A series of substrates to distinguish between different induced cytochromes P-450. Biochemistry and Pharmacology 34:3337-3345.
    • (1985) Biochemistry and Pharmacology , vol.34 , pp. 3337-3345
    • Burke, M.D.1    Thompson, S.2    Elcombe, C.R.3    Halpert, J.4    Haaparanta, T.5    Mayer, R.T.6
  • 3
    • 0035192944 scopus 로고    scopus 로고
    • Differential inhibition and inactivation of human CYP1 enzymes by trans-resveratrol: Evidence for mechanism-based inactivation of CYP1A2
    • Chang TKH, Chen J, Lee WBK. 2001. Differential inhibition and inactivation of human CYP1 enzymes by trans-resveratrol: Evidence for mechanism-based inactivation of CYP1A2. Journal of Pharmacology and Experimental Therapy 299:874-882.
    • (2001) Journal of Pharmacology and Experimental Therapy , vol.299 , pp. 874-882
    • Chang, T.K.H.1    Chen, J.2    Lee, W.B.K.3
  • 4
    • 0033679373 scopus 로고    scopus 로고
    • Trans-resveratrol modulates the catalytic activity and m-RNA expression of the procarcinogen-activating human cytochrome P450 1B1
    • Chang TKH, Lee WBK, Ko HH. 2000. Trans-resveratrol modulates the catalytic activity and m-RNA expression of the procarcinogen-activating human cytochrome P450 1B1. Canadian Journal of Physiology and Pharmacology 78:874-881.
    • (2000) Canadian Journal of Physiology and Pharmacology , vol.78 , pp. 874-881
    • Chang, T.K.H.1    Lee, W.B.K.2    Ko, H.H.3
  • 5
    • 0035076024 scopus 로고    scopus 로고
    • Effect of trans-resveratrol on 7-benzyloxy-4-trifluoromethylcoumarin O-dealkylation catalysed by human recombinant CYP3A4 and CYP3A5
    • Chang TKH, Yeung RKY. 2001. Effect of trans-resveratrol on 7-benzyloxy-4-trifluoromethylcoumarin O-dealkylation catalysed by human recombinant CYP3A4 and CYP3A5. Canadian Journal of Physiology and Pharmacology 79:220-226.
    • (2001) Canadian Journal of Physiology and Pharmacology , vol.79 , pp. 220-226
    • Chang, T.K.H.1    Yeung, R.K.Y.2
  • 8
    • 0001954884 scopus 로고
    • Inhibition of chemical carcinogenesis
    • Cooper CS, Grover PL, editors. Berlin: Springer
    • DiGiovanni J. 1990. Inhibition of chemical carcinogenesis. In: Cooper CS, Grover PL, editors. Handbook of experimental pharmacology. Berlin: Springer. pp 159-223.
    • (1990) Handbook of Experimental Pharmacology , pp. 159-223
    • DiGiovanni, J.1
  • 9
    • 0028820801 scopus 로고
    • Role of cytochrome P4501A2 in chemical carcinogenesis: Implication for human variability in expression and enzyme activity
    • Eaton DL, Gallagher EP, Bammler TK, Kunze KL. 1995. Role of cytochrome P4501A2 in chemical carcinogenesis: Implication for human variability in expression and enzyme activity. Pharmacogenetics 5:259-274.
    • (1995) Pharmacogenetics , vol.5 , pp. 259-274
    • Eaton, D.L.1    Gallagher, E.P.2    Bammler, T.K.3    Kunze, K.L.4
  • 10
    • 0034645693 scopus 로고    scopus 로고
    • Biological effects of resveratrol
    • Fremont L. 2000. Biological effects of resveratrol. Life Sciences 66:663-673.
    • (2000) Life Sciences , vol.66 , pp. 663-673
    • Fremont, L.1
  • 12
    • 0142243190 scopus 로고    scopus 로고
    • Relationship between mechanisms, bioavailibility, and preclinical chemopreventive efficacy of resveratrol: A conundrum
    • Gescher AJ, Steward WP. 2003. Relationship between mechanisms, bioavailibility, and preclinical chemopreventive efficacy of resveratrol: A conundrum. Cancer Epidemiology and Biomarkers 12:953-957.
    • (2003) Cancer Epidemiology and Biomarkers , vol.12 , pp. 953-957
    • Gescher, A.J.1    Steward, W.P.2
  • 13
    • 0002254766 scopus 로고
    • Analysis and characterization of enzymes
    • Hayes AW, editor. New York, NY: Raven
    • Guengerich FP. 1994. Analysis and characterization of enzymes. In: Hayes AW, editor. Principles and methods of toxicology. New York, NY: Raven. pp 1259-1313.
    • (1994) Principles and Methods of Toxicology , pp. 1259-1313
    • Guengerich, F.P.1
  • 14
  • 15
    • 0027934462 scopus 로고
    • Inhibition of p-nitrophenol hydroxylase in rat liver microsomes by small aromatic and heterocyclic molecules
    • Hargreaves MB, Jones BC, Smith DA, Gescher A. 1994. Inhibition of p-nitrophenol hydroxylase in rat liver microsomes by small aromatic and heterocyclic molecules. Drug Metabolism and Disposition 22:806-810.
    • (1994) Drug Metabolism and Disposition , vol.22 , pp. 806-810
    • Hargreaves, M.B.1    Jones, B.C.2    Smith, D.A.3    Gescher, A.4
  • 16
    • 0035689866 scopus 로고    scopus 로고
    • Resveratrol, a natural chemopreventive agent against degenerative diseases
    • Ignatowicz E, Baer-Dubowska W. 2001. Resveratrol, a natural chemopreventive agent against degenerative diseases. Polish Journal of Pharmacology 53:557-569.
    • (2001) Polish Journal of Pharmacology , vol.53 , pp. 557-569
    • Ignatowicz, E.1    Baer-Dubowska, W.2
  • 17
    • 0033559420 scopus 로고    scopus 로고
    • Inhibitory effects of resveratrol analogs on unopsonized zymosan-induced oxygen radical production
    • Jang DS, Kang BS, Ryu SY, Chang IM, Min KR, Kim Y. 1999. Inhibitory effects of resveratrol analogs on unopsonized zymosan-induced oxygen radical production. Biochemistry and Pharmacology 57:705-712.
    • (1999) Biochemistry and Pharmacology , vol.57 , pp. 705-712
    • Jang, D.S.1    Kang, B.S.2    Ryu, S.Y.3    Chang, I.M.4    Min, K.R.5    Kim, Y.6
  • 19
    • 0141566405 scopus 로고    scopus 로고
    • Resveratrol and two monomethylated stilbenes from Israeli Rumex bucephalophorus and their antioxidant potential
    • Kerem Z, Regev-Shoshani G, Flaishman MA, Sivan L. 2003. Resveratrol and two monomethylated stilbenes from Israeli Rumex bucephalophorus and their antioxidant potential. Journal of Natural Products 66:1270-1272.
    • (2003) Journal of Natural Products , vol.66 , pp. 1270-1272
    • Kerem, Z.1    Regev-Shoshani, G.2    Flaishman, M.A.3    Sivan, L.4
  • 20
    • 0037011901 scopus 로고    scopus 로고
    • Design, synthesis and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors
    • Kim S, Ko H, Park JE, Jung S, Lee SK, Chun YJ. 2002. Design, synthesis and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors. Journal of Medicinal Chemistry 45:160-164.
    • (2002) Journal of Medicinal Chemistry , vol.45 , pp. 160-164
    • Kim, S.1    Ko, H.2    Park, J.E.3    Jung, S.4    Lee, S.K.5    Chun, Y.J.6
  • 22
    • 0036497073 scopus 로고    scopus 로고
    • Substrate specificity for rat cytochrome P450 (CYP) isoforms: Screening with cDNA-expressed systems of the rat
    • Kobayashi K, Urishima K, Shimada N, Chiba K. 2002. Substrate specificity for rat cytochrome P450 (CYP) isoforms: Screening with cDNA-expressed systems of the rat. Biochemistry and Pharmacology 63:889-896.
    • (2002) Biochemistry and Pharmacology , vol.63 , pp. 889-896
    • Kobayashi, K.1    Urishima, K.2    Shimada, N.3    Chiba, K.4
  • 23
    • 0022494453 scopus 로고
    • Hydroxylation of p-nitrophenol by rabbit ethanol-inducible cytochrome P-450 isozyme 3a
    • Koop DR. 1986. Hydroxylation of p-nitrophenol by rabbit ethanol-inducible cytochrome P-450 isozyme 3a. Molecular Pharmacology 29:399-404.
    • (1986) Molecular Pharmacology , vol.29 , pp. 399-404
    • Koop, D.R.1
  • 24
    • 0038394282 scopus 로고    scopus 로고
    • The effects of tannic acid on cytochrome P450 and phase II enzyme in mouse liver and kidney
    • Krajka-Kuźniak V, Baer-Dubowska W. 2003. The effects of tannic acid on cytochrome P450 and phase II enzyme in mouse liver and kidney. Toxicology Letters 143:209-216.
    • (2003) Toxicology Letters , vol.143 , pp. 209-216
    • Krajka-Kuźniak, V.1    Baer-Dubowska, W.2
  • 25
    • 0027999623 scopus 로고
    • Rapid metabolic phenotypes for acetyltransferase and cytochrome P4501A2 and putative exposure to food-borne heterocyclic amines increase the risk for colorectal cancer or polyps
    • Lang NP, Butler MA, Mussengill J, Lawson M, Stotts RC, Hauer-Jensen M, Kadlubar FF. 1994. Rapid metabolic phenotypes for acetyltransferase and cytochrome P4501A2 and putative exposure to food-borne heterocyclic amines increase the risk for colorectal cancer or polyps. Cancer Epidemiology and Biomarkers 3:675-682.
    • (1994) Cancer Epidemiology and Biomarkers , vol.3 , pp. 675-682
    • Lang, N.P.1    Butler, M.A.2    Mussengill, J.3    Lawson, M.4    Stotts, R.C.5    Hauer-Jensen, M.6    Kadlubar, F.F.7
  • 28
    • 0036182290 scopus 로고    scopus 로고
    • Induction of apoptosis by 3,4′-dimethoxy-5-hydroxystilbene in human promyeloid leukemic HL-60 cells
    • Lee SH, Ryu SY, Kim HB, Kim MY, Chun YJ. 2002. Induction of apoptosis by 3,4′-dimethoxy-5-hydroxystilbene in human promyeloid leukemic HL-60 cells. Planta Medica 68:123-127.
    • (2002) Planta Medica , vol.68 , pp. 123-127
    • Lee, S.H.1    Ryu, S.Y.2    Kim, H.B.3    Kim, M.Y.4    Chun, Y.J.5
  • 29
    • 3242808209 scopus 로고    scopus 로고
    • Quantitative structure-activity relationships within a homologous series of 7-alkoxyresorufins exhibiting activity towards CYP1A and CYP2B enzymes: Molecular modeling studies on key members of the resorufin series with CYP2C5-derived models of human CYP1A1, CYP1A2, CYP2B6 and CYP3A4
    • Lewis DFV, Lake BG, Dickins M. 2004. Quantitative structure-activity relationships within a homologous series of 7-alkoxyresorufins exhibiting activity towards CYP1A and CYP2B enzymes: Molecular modeling studies on key members of the resorufin series with CYP2C5-derived models of human CYP1A1, CYP1A2, CYP2B6 and CYP3A4. Xenobiotica 34:501-513.
    • (2004) Xenobiotica , vol.34 , pp. 501-513
    • Lewis, D.F.V.1    Lake, B.G.2    Dickins, M.3
  • 30
    • 0036749125 scopus 로고    scopus 로고
    • Flavonoids and stilbenoids with COX-1 and COX-2 inhibitory activity from Dracena loureiri
    • Likhitwitayawuid K, Sawasdee K, Kirtikara K. 2002. Flavonoids and stilbenoids with COX-1 and COX-2 inhibitory activity from Dracena loureiri. Planta Medica 68:841-843.
    • (2002) Planta Medica , vol.68 , pp. 841-843
    • Likhitwitayawuid, K.1    Sawasdee, K.2    Kirtikara, K.3
  • 32
    • 4444335573 scopus 로고    scopus 로고
    • Anti-allergic activity of stilbenes from Korean rhubarb (Rheum undulatum L.): Structure requirements for inhibition of antigen-induced degranulation and their effects on the release of TNF-α and IL-4 in RBL-2H3 cells
    • Matsuda H, Tewtrakul S, Morikawa T, Yoshikawa M. 2004. Anti-allergic activity of stilbenes from Korean rhubarb (Rheum undulatum L.): Structure requirements for inhibition of antigen-induced degranulation and their effects on the release of TNF-α and IL-4 in RBL-2H3 cells. Bioorganic and Medicinal Chemistry 12:4871-4876.
    • (2004) Bioorganic and Medicinal Chemistry , vol.12 , pp. 4871-4876
    • Matsuda, H.1    Tewtrakul, S.2    Morikawa, T.3    Yoshikawa, M.4
  • 33
  • 34
    • 0038085651 scopus 로고    scopus 로고
    • Effect of natural phenols on the catalytic activity of cytochrome P450 2E1
    • Mikstacka R, Gnojkowski J, Baer-Dubowska W. 2002. Effect of natural phenols on the catalytic activity of cytochrome P450 2E1. Acta Biochimica Polonica 49:917-925.
    • (2002) Acta Biochimica Polonica , vol.49 , pp. 917-925
    • Mikstacka, R.1    Gnojkowski, J.2    Baer-Dubowska, W.3
  • 35
    • 0023907450 scopus 로고
    • Isolation, structure, synthesis, and antimitotic properties of combrestatins B-3 and B-4 from Combretum caffrum
    • Pettit GR, Singh SB, Schmidt JM, Niven ML, Hamel E, Lin CH. 1988. Isolation, structure, synthesis, and antimitotic properties of combrestatins B-3 and B-4 from Combretum caffrum. Journal of Natural Products 51:517-527.
    • (1988) Journal of Natural Products , vol.51 , pp. 517-527
    • Pettit, G.R.1    Singh, S.B.2    Schmidt, J.M.3    Niven, M.L.4    Hamel, E.5    Lin, C.H.6
  • 36
    • 0035976379 scopus 로고    scopus 로고
    • Inhibition of CYP3A, CYP1A and CYP2E1 activities by resveratrol and other non volatile red wine components
    • Piver B, Berthou F, Dreano Y, Lucas D. 2001. Inhibition of CYP3A, CYP1A and CYP2E1 activities by resveratrol and other non volatile red wine components. Toxicology Letters 125:83-91.
    • (2001) Toxicology Letters , vol.125 , pp. 83-91
    • Piver, B.1    Berthou, F.2    Dreano, Y.3    Lucas, D.4
  • 41
    • 0022117289 scopus 로고
    • p-Nitrophenol hydroxylation - A microsomal oxidation which is highly inducible by ethanol
    • Reinke LA, Moyer MJ. 1985. p-Nitrophenol hydroxylation - a microsomal oxidation which is highly inducible by ethanol. Drug Metabolism and Disposition 13:548-552.
    • (1985) Drug Metabolism and Disposition , vol.13 , pp. 548-552
    • Reinke, L.A.1    Moyer, M.J.2
  • 43
    • 0027965141 scopus 로고
    • Revision of the NMR assignments of pterostilbene and of dihydrodehydroconiferyl alcohol: Cytotoxic constituents from Anogeissus acuminata
    • Rimando AM, Pezzuto JM, Farnsworth NR, Santisuk T, Reutraul V. 1994. Revision of the NMR assignments of pterostilbene and of dihydrodehydroconiferyl alcohol: Cytotoxic constituents from Anogeissus acuminata. Natural Product Letters 4:267-272.
    • (1994) Natural Product Letters , vol.4 , pp. 267-272
    • Rimando, A.M.1    Pezzuto, J.M.2    Farnsworth, N.R.3    Santisuk, T.4    Reutraul, V.5
  • 45
    • 10744229260 scopus 로고    scopus 로고
    • Pharmacokinetics in mice and growth-inhibitory properties of the putative cancer chemopreventive agent resveratrol and the synthetic analogue trans-3,4,5,4′-tetramethoxystilbene
    • Sale S, Verschoyle RD, Boocock D, Jones DJL, Wilsher N, Ruparelia KC, Potter GA, Farmer PB, Steward WP, Gescher AJ. 2004. Pharmacokinetics in mice and growth-inhibitory properties of the putative cancer chemopreventive agent resveratrol and the synthetic analogue trans-3,4,5,4′- tetramethoxystilbene. British Journal of Cancer 90:736-744.
    • (2004) British Journal of Cancer , vol.90 , pp. 736-744
    • Sale, S.1    Verschoyle, R.D.2    Boocock, D.3    Djl, J.4    Wilsher, N.5    Ruparelia, K.C.6    Potter, G.A.7    Farmer, P.B.8    Steward, W.P.9    Gescher, A.J.10
  • 46
    • 0032444641 scopus 로고    scopus 로고
    • Human cytochrome P450s: Selectivity and measurement in vivo
    • Smith DA, Abel SM, Hyland R, Jones BC. 1998a. Human cytochrome P450s: Selectivity and measurement in vivo. Xenobiotica 28:1095-1128.
    • (1998) Xenobiotica , vol.28 , pp. 1095-1128
    • Smith, D.A.1    Abel, S.M.2    Hyland, R.3    Jones, B.C.4
  • 47
    • 0032414615 scopus 로고    scopus 로고
    • Molecular genetics of the human cytochrome P450 monooxygenase superfamily
    • Smith G, Stubbins MJ, Harries W, Wolf CR. 1998b. Molecular genetics of the human cytochrome P450 monooxygenase superfamily. Xenobiotica 28:1129-1165.
    • (1998) Xenobiotica , vol.28 , pp. 1129-1165
    • Smith, G.1    Stubbins, M.J.2    Harries, W.3    Wolf, C.R.4
  • 51
    • 0032813348 scopus 로고    scopus 로고
    • Molecular mechanisms of chemopreventive effects of selected dietary and medicinal phenolic substances
    • Surh YJ. 1999. Molecular mechanisms of chemopreventive effects of selected dietary and medicinal phenolic substances. Mutation Research 428:305-327.
    • (1999) Mutation Research , vol.428 , pp. 305-327
    • Surh, Y.J.1
  • 52
    • 3042641988 scopus 로고    scopus 로고
    • Alteration in phase I and II enzyme activities and polycyclic aromatic hydrocarbons-DNA adduct formation by plant phenolics in mouse epidermis
    • Szaefer H, Cichocki M, Brauze D, Baer-Dubowska W. 2004. Alteration in phase I and II enzyme activities and polycyclic aromatic hydrocarbons-DNA adduct formation by plant phenolics in mouse epidermis. Nutrition and Cancer 48:70-77.
    • (2004) Nutrition and Cancer , vol.48 , pp. 70-77
    • Szaefer, H.1    Cichocki, M.2    Brauze, D.3    Baer-Dubowska, W.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.