The inhibitory effect of tannic acid on cytochrome P450 enzymes and NADPH-CYP reductase in rat and human liver microsomes

Food and Chemical Toxicology

Volumn 46, Issue 2, 2008, Pages 645-653

  Yao, Hsien Tsung ^a   Chang, Yi Wei ^a   Lan, Shih Jung ^a   Yeh, Teng Kuang ^a  

^a NATIONAL HEALTH RESEARCH INSTITUTES   (Taiwan)

Author keywords

CYP; Inhibition; Microsomes; NADPH CYP reductase; Tannic acid

Indexed keywords

4 NITROPHENOL; CHLORZOXAZONE; CYTOCHROME P450; CYTOCHROME P450 1A1; CYTOCHROME P450 1A2; CYTOCHROME P450 3A4; DEXTROMETHORPHAN; DICLOFENAC; ETHOXYRESORUFIN DEETHYLASE; OXYGENASE; PHENACETIN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE FERRIHEMOPROTEIN REDUCTASE; TANNIN; TESTOSTERONE; TOLBUTAMIDE;

ARTICLE; BACULOVIRUS EXPRESSION SYSTEM; CATALYSIS; COMPETITIVE INHIBITION; CONTROLLED STUDY; DEMETHYLATION; DRUG EFFECT; DRUG HYDROXYLATION; DRUG SELECTIVITY; ENZYME ACTIVITY; ENZYME INHIBITION; HYDROXYLATION; IC 50; INSECT CELL; LIVER MICROSOME; MALE; NONHUMAN; OXIDATION; RAT;

ANIMALS; CYTOCHROME P-450 ENZYME SYSTEM; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; HUMANS; ISOENZYMES; MALE; MICROSOMES, LIVER; NADPH-FERRIHEMOPROTEIN REDUCTASE; RATS; RATS, SPRAGUE-DAWLEY; SPECIES SPECIFICITY; TANNINS;

HEXAPODA; RATTUS; RODENTIA;

EID: 37449027358     PISSN: 02786915     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.fct.2007.09.073     Document Type: Article

References (36)

1. Athar M., Khan W.A., and Mukhtar H. Effect of dietary tannic acid on epidermal, lung, and forestomach polycyclic aromatic hydrocarbon metabolism and tumorigenicity in Sencar mice. Cancer Res. 49 (1989) 5784-5788
2. Badawy A.A., White A.E., and Lathe G.H. The effect of tannic acid on the synthesis of protein and nucleic acid by rat liver. Biochem. J. 113 (1969) 307-313
3. Baer-Dubowska W., Szaefer H., and Krajka-Kuzniak V. Inhibition of murine hepatic cytochrome P450 activities by natural and synthetic phenolic compounds. Xenobiotica 28 (1998) 735-743
4. Burke M.D., Thompson S., Weaver R.J., Wolf C.R., and Mayer R.T. Cytochrome P450 specificities of alkoxyresorufin O-dealkylation in human and rat liver microsomes. Biochem. Pharmacol. 48 (1994) 923-936
5. Capdevila J., Chacos N., Werringloer J., Prough R.A., and Estabrook R.W. Liver microsomal cytochrome P-450 and the oxidative metabolism of arachidonic acid. Proc. Natl. Acad. Sci. USA 78 (1981) 5362-5366
6. Chen S.C., and Chung K.T. Mutagenicity and antimutagenicity studies of tannic acid and its related compounds. Food Chem. Toxicol. 38 (2000) 1-5
7. Chung K.T., Wong T.Y., Wei C.I., Huang Y.W., and Lin Y. Tannins and human health: a review. Crit. Rev. Food Sci. Nutr. 38 (1998) 421-464
8. Funae Y., and Imaoka S. Cytochrome P450 in rodents. In: Schenkman J.B., and Greim H. (Eds). Handbook of Experimental Pharmacocology. Cytochrome P450 vol. 105 (1993), Springer-Verlag, Berlin and Heidelberg 221-238
9. Guengerich F.P. Human cytochrome P450 enzymes. In: Ortiz de Montellano P.R. (Ed). Cytochrome P450: Structure, Mechanism, and Biochemistry (1995), Springer, Berlin 473-535
10. Huang M.T., Chang R.L., Fortner J.G., and Conney A.H. Studies on the mechanism of activation of microsomal benzo[a]pyrene hydroxylation by flavonoids. J. Biol. Chem. 256 (1981) 6829-6836
11. Krajka-Kuzniak V., and Baer-Dubowska W. The effects of tannic acid on cytochrome P450 and phase II enzymes in mouse liver and kidney. Toxicol. Lett. 143 (2003) 209-216
12. Lee C.A., Manyike P.T., Thummel K.E., Nelson S.D., and Slattery J.T. Mechanism of cytochrome P450 activation by caffeine and 7,8-benzoflavone in rat liver microsomes. Drug Metab. Dispos. 25 (1997) 1150-1156
13. Maiani G., Serafini M., Salucci M., Azzini E., and Ferro-Luzzi A. Application of a new high-performance liquid chromatographic method for measuring selected polyphenols in human plasma. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 692 (1997) 311-317
14. Miwa G.T., West S.B., and Lu A.Y. Studies on the rate limiting enzyme component in the microsomal monooxygenase system. Incorporation of purified NADPH-cytochrome c reductase and cytochrome P-450 into rat liver microsomes. J. Biol. Chem. 253 (1978) 1921-1929
15. Moon Y.J., Wang X., and Morris M.E. Dietary flavonoids: effects on xenobiotic and carcinogen metabolism. Toxicol In Vitro. 20 (2006) 187-210
16. Muto S., Fujita K., Yamazaki Y., and Kamataki T. Inhibition by green tea catechins of metabolic activation of procarcinogens by human cytochrome P450. Mutat. Res. 479 (2001) 197-206
17. Nakagawa K., Okuda S., and Miyazawa T. Dose-dependent incorporation of tea catechins, (2)-epigallocatechin-3-gallate and (2)-epigallocatechin, into human plasma. Biosci. Biotechnol. Biochem. 61 (1997) 1981-1985
18. Nepka C., Asprodini E., and Kouretas D. Tannins, xenobiotic metabolism and cancer chemoprevention in experimental animals. Eur. J. Drug Metab. Pharmacokinet. 24 (1999) 183-189
19. Newmark H.L. Plant phenolics as inhibitors of mutational and precarcinogenic events. Can. J. Physiol. Pharmacol. 65 (1987) 461-466
20. Omura T., and Sato R. The carbon monoxide-binding pigment of liver microsomes. l. Evidence for its hemeprotein nature. J. Biol. Chem. 239 (1964) 2370-2379
21. Peterson S., Lampe J.W., Bammler T.K., Gross-Steinmeyer K., and Eaton D.L. Apiaceous vegetable constituents inhibit human cytochrome P-450 1A2 (hCYP1A2) activity and hCYP1A2-mediated mutagenicity of aflatoxin B(1). Food Chem. Toxicol. 44 (2006) 1474-1484
22. Phillips A.H., and Langdon R.G. Hepatic triphosphopyridine nucleotide-cytochrome c reductase: isolation, characterization, and kinetic studies. J. Biol. Chem. 237 (1962) 2652-2660
23. Sanyal R., Darroudi F., Parzefall W., Nagao M., and Knasmuller S. Inhibition of the genotoxic effects of heterocyclic amines in human derived hepatoma cells by dietary bioantimutagens. Mutagenesis 12 (1997) 297-303
24. Scalbert A., and Williamson G. Dietary intake and bioavailability of polyphenols. J. Nutr. 130 (2000) 2073S-2085S
25. Sesardic D., Boobis A.R., Murray B.P., Murray S., Segura J., de la Torre R., and Davies D.S. Furafylline is a potent and selective inhibitor of cytochrome P4501A2 in man. Br. J. Clin. Pharmacol. 29 (1990) 651-663
26. Shou M., Korzekwa K.R., Crespi C.L., Gonzalez F.J., and Gelboin H.V. The role of 12 cDNA-expressed human, rodent, and rabbit cytochromes P450 in the metabolism of benzo[a]pyrene and benzo[a]pyrene trans-7,8-dihydrodiol. Mol. Carcinog. 10 (1994) 159-1568
27. Sinclair P.R., Gorman N., Tsyrlov I.B., Fuhr U., Walton H.S., and Sinclair J.H. Uroporphyrinogen oxidation catalyzed by human cytochromes P450. Drug Metab. Dispos. 26 (1998) 1019-1025
28. Stresser D.M., Broudy M.I., Ho T., Cargill C.E., Blanchard A.P., Sharma R., Dandeneau A.A., Goodwin J.J., Turner S.D., Erve J.C., Patten C.J., Dehal S.S., and Crespi C.L. Highly selective inhibition of human CYP3Aa in vitro by azamulin and evidence that inhibition is irreversible. Drug Metab. Dispos. 32 (2004) 105-112
29. Sugiyama T., Kubota Y., Shinozuka K., Yamada S., Wu J., and Umegaki K. Ginkgo biloba extract modifies hypoglycemic action of tolbutamide via hepatic cytochrome P450 mediated mechanism in aged rats. Life Sci. 75 (2004) 1113-1122
30. Szaefer H., Jodynis-Liebert J., Cichocki M., Matuszewska A., and Baer-Dubowska W. Effect of naturally occurring plant phenolics on the induction of drug metabolizing enzymes by o-toluidine. Toxicology 186 (2003) 67-77
31. Teel R.W., and Huynh H. Modulation by phytochemicals of cytochrome P450-linked enzyme activity. Cancer Lett. 133 (1998) 135-141
32. von Moltke L.L., Greenblatt D.J., Duan S.X., Schmider J., Kudchadker L., Fogelman S.M., Harmatz J.S., and Shader R.I. Phenacetin O-deethylation by human liver microsomes in vitro: inhibition by chemical probes, SSRI antidepressants, nefazodone and venlafaxine. Psychopharmacology 128 (1996) 398-407
33. Walsky R.L., and Obach R.S. Validated assays for human cytochrome P450 activities. Drug Metab. Dispos. 32 (2004) 647-660
34. Weaver R., Graham K.S., Beattie I.G., and Riley R.J. Cytochrome P450 inhibition using recombinant proteins and mass spectrometry/multiple reaction monitoring technology in a cassette incubation. Drug Metab. Dispos. 31 (2003) 955-966
35. Yao H.T., Chang Y.W., Lan S.J., Chen C.T., Hsu J.T., and Yeh T.K. The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes. Life Sci. 79 (2006) 2432-2440
36. Zhu J., Filippich L.J., and Ng J. Rumen involvement in sheep tannic acid metabolism. Vet. Hum. Toxicol. 37 (1995) 436-440