Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 36, 2006 - Issue 4
152
Views
29
CrossRef citations to date
0
Altmetric
Research Article

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

, , , &
Pages 269-285 | Received 19 Jan 2006, Published online: 22 Sep 2008

References

  • Baer-Dubowska W, Szaefer H, Krajka-Kuźniak V. Inhibition of murine hepatic cytochrome P450 activities by natural and synthetic phenolic compounds. Xenobiotica 1998; 28: 735–743
  • Burke MD, Thompson S, Elcombe CR, Halpert J, Haaparanta T, Mayer RT. Ethoxy-, pentoxy- and benzyloxyphenoxazones and homologues: A series of substrates to distinguish between different induced cytochromes P-450. Biochemistry and Pharmacology 1985; 34: 3337–3345
  • Chang TKH, Chen J, Lee WBK. Differential inhibition and inactivation of human CYP1 enzymes by trans-resveratrol: Evidence for mechanism-based inactivation of CYP1A2. Journal of Pharmacology and Experimental Therapy 2001; 299: 874–882
  • Chang TKH, Lee WBK, Ko HH. Trans-resveratrol modulates the catalytic activity and m-RNA expression of the procarcinogen-activating human cytochrome P450 1B1. Canadian Journal of Physiology and Pharmacology 2000; 78: 874–881
  • Chang TKH, Yeung RKY. Effect of trans-resveratrol on 7-benzyloxy-4-trifluoromethylcoumarin O-dealkylation catalysed by human recombinant CYP3A4 and CYP3A5. Canadian Journal of Physiology and Pharmacology 2001; 79: 220–226
  • Chun YJ, Kim MY, Guengerich FP. Resveratrol is a selective human cytochrome P450 1A1 inhibitor. Biochemical and Biophysical Research Communications 1999; 268: 20–24
  • Chun YJ, Ryu SY, Jeong TC, Kim MY. Mechanism-based inhibition of human cytochrome P450 1A1 by rhapontigenin. Drug Metabolism and Disposition 2001; 29: 389–393
  • DiGiovanni J. Inhibition of chemical carcinogenesis. Handbook of experimental pharmacology, CS Cooper, PL Grover. Springer, Berlin 1990; 159–223
  • Eaton DL, Gallagher EP, Bammler TK, Kunze KL. Role of cytochrome P4501A2 in chemical carcinogenesis: Implication for human variability in expression and enzyme activity. Pharmacogenetics 1995; 5: 259–274
  • Fremont L. Biological effects of resveratrol. Life Sciences 2000; 66: 663–673
  • Gerhäuser C, Klimo K, Heiss E, Neumann I, Gamal-Eldeen A, Knauft J, Liu G-Y, Sitthimonchai S, Frank N. Mechanism-based in vitro screening of potential cancer chemopreventive agents. Mutation Research 2003; 523–524: 163–172
  • Gescher AJ, Steward WP. Relationship between mechanisms, bioavailibility, and preclinical chemopreventive efficacy of resveratrol: A conundrum. Cancer Epidemiology and Biomarkers 2003; 12: 953–957
  • Guengerich FP. Analysis and characterization of enzymes. Principles and methods of toxicology, AW Hayes. Raven, New York, NY 1994; 1259–1313
  • Guengerich FP, Chun Y-J, Kim D, Gillam EMJ, Shimada T. Cytochrome P450 1B1: A target for inhibition in anticarcinogenesis strategies. Mutation Research 2003; 523–524: 173–182
  • Hargreaves MB, Jones BC, Smith DA, Gescher A. Inhibition of p-nitrophenol hydroxylase in rat liver microsomes by small aromatic and heterocyclic molecules. Drug Metabolism and Disposition 1994; 22: 806–810
  • Ignatowicz E, Baer-Dubowska W. Resveratrol, a natural chemopreventive agent against degenerative diseases. Polish Journal of Pharmacology 2001; 53: 557–569
  • Jang DS, Kang BS, Ryu SY, Chang IM, Min KR, Kim Y. Inhibitory effects of resveratrol analogs on unopsonized zymosan-induced oxygen radical production. Biochemistry and Pharmacology 1999; 57: 705–712
  • Kadlubar FF, Butler MA, Kaderlik KR, Chou HC, Lang NP. Polymorphisms for aromatic amine metabolism in humans: Relevance for human carcinogenesis. Environmental Health Perspectives 1992; 98: 69–74
  • Kerem Z, Regev-Shoshani G, Flaishman MA, Sivan L. Resveratrol and two monomethylated stilbenes from Israeli Rumex bucephalophorus and their antioxidant potential. Journal of Natural Products 2003; 66: 1270–1272
  • Kim S, Ko H, Park JE, Jung S, Lee SK, Chun YJ. Design, synthesis and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors. Journal of Medicinal Chemistry 2002; 45: 160–164
  • Ko SK, Lee CR, Lee HS, Kim H, Baek KH, Tokuoka K, Chung SH. Inhibitory effects of stilbene derivatives from Rheum undulatum on cyclooxygenase activity. Saengyak Hakhoechi 2003; 34: 25–27
  • Kobayashi K, Urishima K, Shimada N, Chiba K. Substrate specificity for rat cytochrome P450 (CYP) isoforms: Screening with cDNA-expressed systems of the rat. Biochemistry and Pharmacology 2002; 63: 889–896
  • Koop DR. Hydroxylation of p-nitrophenol by rabbit ethanol-inducible cytochrome P-450 isozyme 3a. Molecular Pharmacology 1986; 29: 399–404
  • Krajka-Kuźniak V, Baer-Dubowska W. The effects of tannic acid on cytochrome P450 and phase II enzyme in mouse liver and kidney. Toxicology Letters 2003; 143: 209–216
  • Lang NP, Butler MA, Mussengill J, Lawson M, Stotts RC, Hauer-Jensen M, Kadlubar FF. 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 1994; 3: 675–682
  • Latruffe N, Delmas D, Jannin B, Cherkaoui-Malki M, Passilly-Degrace P, Berlot JP. Molecular analysis on the chemopreventive properties of resveratrol a plant polyphenol microcomponent. International Journal of Molecular Medicine 2002; 10: 755–760
  • Le Marchand L, Hankin JH, Wilkens LR, Pierce LM, Franke A, Kolonel LN, Seifried A, Custer LJ, Chang W, Lum-Jones A, Donlon T. Combined effects of well-done red meat, smoking, and rapid N-acetyltransferase 2 and CYP1A2 phenotypes in increasing colorectal cancer risk. Cancer Epidemiology and Biomarkers 2001; 10: 1259–1266
  • Lee SH, Ryu SY, Kim HB, Kim MY, Chun YJ. Induction of apoptosis by 3,4′-dimethoxy-5-hydroxystilbene in human promyeloid leukemic HL-60 cells. Planta Medica 2002; 68: 123–127
  • Lewis DFV, Lake BG, Dickins M. 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 2004; 34: 501–513
  • Likhitwitayawuid K, Sawasdee K, Kirtikara K. Flavonoids and stilbenoids with COX-1 and COX-2 inhibitory activity from Dracena loureiri. Planta Medica 2002; 68: 841–843
  • Lowry OH, Rosebrough NJ, Farr AL, Randall RJ. Protein measurement with the Folin phenol reagent. Journal of Biological Chemistry 1951; 193: 230–265
  • Matsuda H, Tewtrakul S, Morikawa T, Yoshikawa M. 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 2004; 12: 4871–4876
  • Matsuoka A, Takeshita K, Furuta A, Ozaki M, Fukuhara K, Miyata N. The 4′-hydroxy group is responsible for the in vitro cytogenetic activity of resveratrol. Mutation Research 2002; 521: 29–35
  • Mikstacka R, Gnojkowski J, Baer-Dubowska W. Effect of natural phenols on the catalytic activity of cytochrome P450 2E1. Acta Biochimica Polonica 2002; 49: 917–925
  • Pettit GR, Singh SB, Schmidt JM, Niven ML, Hamel E, Lin CH. Isolation, structure, synthesis, and antimitotic properties of combrestatins B-3 and B-4 from Combretum caffrum. Journal of Natural Products 1988; 51: 517–527
  • Piver B, Berthou F, Dreano Y, Lucas D. Inhibition of CYP3A, CYP1A and CYP2E1 activities by resveratrol and other non volatile red wine components. Toxicology Letters 2001; 125: 83–91
  • Piver B, Fer M, Vitrac X, Merillon J-M, Dreano Y, Berthou F, Lucas D. Involvement of cytochrome P450 1A2 in the biotransformation of trans-resveratrol in human liver microsomes. Biochemistry and Pharmacology 2004; 68: 773–782
  • Potter GA, Patterson LH, Wanogho E, Perry PJ, Butler PC, Ijaz T, Ruparelia KC, Lamb JH, Farmer PB, Stanley LA, Burke MD. The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYP1B1. British Journal of Cancer 2002; 86: 774–778
  • Regev-Shoshani G, Shoseyov O, Bilkis I, Kerem Z. Glycosylation of resveratrol protects it from enzymatic oxidation. Biochemistry Journal 2003; 374: 157–163
  • Regev-Shoshani G, Shoseyov O, Kerem Z. Influence of lipophilicity on the interactions of hydroxyl stilbenes with cytochrome P450 3A4. Biochemical and Biophysical Research Communications 2004; 323: 668–673
  • Reinke LA, Moyer MJ. p-Nitrophenol hydroxylation—a microsomal oxidation which is highly inducible by ethanol. Drug Metabolism and Disposition 1985; 13: 548–552
  • Rimando AM, Cuendet M, Desmarchelier C, Mehta RG, Pezzuto JM, Duke OD. Cancer chemopreventive and antioxidant activities of pterostilbene, a naturally occurring analogue of resveratrol. Journal of Agriculture and Food Chemistry 2002; 50: 3453–3457
  • Rimando AM, Pezzuto JM, Farnsworth NR, Santisuk T, Reutraul V. Revision of the NMR assignments of pterostilbene and of dihydrodehydroconiferyl alcohol: Cytotoxic constituents from Anogeissus acuminata. Natural Product Letters 1994; 4: 267–272
  • Ryu SY, Choi SU, Lee CO, Lee SH, Ahn JW, Zee OP. Antitumor activity of some phenolic components in plants. Archives in Pharmacology Research 1994; 17: 42–44
  • Sale S, Verschoyle RD, Boocock D, Jones DJL, Wilsher N, Ruparelia KC, Potter GA, Farmer PB, Steward WP, Gescher AJ. 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 2004; 90: 736–744
  • Smith DA, Abel SM, Hyland R, Jones BC. Human cytochrome P450s: Selectivity and measurement in vivo. Xenobiotica 1998a; 28: 1095–1128
  • Smith G, Stubbins MJ, Harries W, Wolf CR. Molecular genetics of the human cytochrome P450 monooxygenase superfamily. Xenobiotica 1998b; 28: 1129–1165
  • Solus JF, Arietta BJ, Harris JR, Sexton DP, Steward JQ, McMunn C, Ihrie P, Mehall JM, Edwards TL, Dawson EP. Genetic variation in eleven phase I drug metabolizm genes in an ethnically diverse population. Pharmacogenomics 2004; 5: 895–931
  • Stivala LA, Savio M, Carafoli F, Perucca P, Bianchi L, Maga G, Forti L, Pagnoni UM, Albini A, Prosperi E, Vannini V. Specific structural determinants are responsible for the antioxidant activity and the cell cycle effects of resveratrol. Journal of Biological Chemistry 2001; 276: 22586–22594
  • Sumner SC, Fennell TR, Moore TA, Chanas B, Gonzales F, Ghanayem BI. Role of cytochrome P4502E1 in the metabolism of acrylamide and acrylonitrile in mice. Chemical Research in Toxicology 2005; 12: 1110–1116
  • Surh YJ. Molecular mechanisms of chemopreventive effects of selected dietary and medicinal phenolic substances. Mutation Research 1999; 428: 305–327
  • Szaefer H, Cichocki M, Brauze D, Baer-Dubowska W. Alteration in phase I and II enzyme activities and polycyclic aromatic hydrocarbons–DNA adduct formation by plant phenolics in mouse epidermis. Nutrition and Cancer 2004; 48: 70–77
  • Yin Q, Shi Y-M, Liu H-M, Li C-B, Zhang W-Q. (E)-3,5,4′-Trimethoxystilbene. Acta Crystallographica 2002; 58: 1180–1181
  • Yu C, Shin YG, Chow A, Li Y, Kosmeder JW, Lee YS, Hirschelman WH, Pezzuto JM, Mehta RG, Van RB. Human, rat, and mouse metabolism of resveratrol. Pharmacology Research 2002; 19: 1907–1914

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.