Effects of food natural products on the biotransformation of PCBs

Environmental Toxicology and Pharmacology

Volumn 25, Issue 2, 2008, Pages 211-217

  James, Margaret O ^a   Sacco, James C ^a   Faux, Laura R ^a  

^a UNIVERSITY OF FLORIDA   (United States)

Author keywords

Hydroxylated PCBs; Induction of PCB metabolism; Inhibition of phase II metabolism; Quercetin

Indexed keywords

ADENOSINE 3' PHOSPHATE 5' PHOSPHOSULFATE; CYTOCHROME P450; CYTOCHROME P450 1A1; CYTOCHROME P450 1A2; GLUCURONOSYLTRANSFERASE; ISOENZYME; NATURAL PRODUCT; POLYCHLORINATED BIPHENYL DERIVATIVE; QUERCETIN;

ARTICLE; BIOAVAILABILITY; BIOTRANSFORMATION; DETOXIFICATION; ENZYME INDUCTION; ENZYME INHIBITION; FOOD; FOOD INDUSTRY; FRUIT; GLUCURONIDATION; HYDROXYLATION; METABOLISM; OXYGENATION; PRIORITY JOURNAL; SULFONATION; UPREGULATION; VEGETABLE;

EID: 38349112254     PISSN: 13826689     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.etap.2007.10.024     Document Type: Article

References (41)

1. Ariyoshi N., Koga N., Oguri K., and Yoshimura H. Metabolism of 2,4,5,2′,4′,5′-hexachlorobiphenyl with liver microsomes of phenobarbital-treated dog; the possible formation of PCB 2,3-arene oxide intermediate. Xenobiotica 22 (1992) 1275-1290
2. Arulmozhiraja S., Shiraishi F., Okumura T., Iida M., Takigami H., Edmonds J.S., and Morita M. Structural requirements for the interaction of 91 hydroxylated polychlorinated biphenyls with estrogen and thyroid hormone receptors. Toxicol. Sci. 84 (2005) 49-62
3. Bergman A., Klasson-Wehler E., and Kuroki H. Selective retention of hydroxylated PCB metabolites in blood. Environ. Health Perspect. 102 (1994) 464-469
4. Culm-Merdek K.E., von Moltke L.L., Gan L., Horan K.A., Reynolds R., Harmatz J.S., Court M.H., and Greenblatt D.J. Effect of extended exposure to grapefruit juice on cytochrome P450 3A activity in humans: comparison with ritonavir. Clin. Pharmacol. Ther. 79 (2006) 243-254
5. Dahan A., and Altman H. Food-drug interaction: grapefruit juice augments drug bioavailability-mechanism, extent and relevance. Eur. J. Clin. Nutr. 58 (2004) 1-9
6. Daidoji T., Gozu K., Iwano H., Inoue H., and Yokota H. UDP-glucuronosyltransferase isoforms catalyzing glucuronidation of hydroxy-polychlorinated biphenyls in rat. Drug Metab. Dispos. 33 (2005) 1466-1476
7. Doi A.M., Lou Z., Holmes E., Li C., Venugopal C.S., James M.O., and Kleinow K.M. Effect of micelle fatty acid composition and 3,4,3′,4′-tetrachlorobiphenyl (TCB) exposure on intestinal [(14)C]-TCB bioavailability and biotransformation in channel catfish in situ preparations. Toxicol. Sci. 55 (2000) 85-96
8. Duignan D.B., Sipes I.G., Leonard T.B., and Halpert J.R. Purification and characterization of the dog hepatic cytochrome P-450 isozyme responsible for the metabolism of 2,2′,4,4′,5,5′-hexachlorobiphenyl. Arch. Biochem. Biophys. 255 (1987) 290-303
9. Emoto C., Yamazaki H., Iketaki H., Yamasaki S., Satoh T., Shimizu R., Suzuki S., Shimada N., Nakajima M., and Yokoi T. Cooperativity of alpha-naphthoflavone in cytochrome P450 3A-dependent drug oxidation activities in hepatic and intestinal microsomes from mouse and human. Xenobiotica 31 (2001) 265-275
10. Galijatovic A., Walle U.K., and Walle T. Induction of UDP-glucuronosyltransferase by the flavonoids chrysin and quercetin in Caco-2 cells. Pharm. Res. 17 (2000) 21-26
11. Goon D., and Klaassen CD. Effects of microsomal enzyme inducers upon UDP-glucuronic acid concentration and UDP-glucuronosyltransferase activity in the rat intestine and liver. Toxicol. Appl. Pharmacol. 115 (1992) 253-260
12. Gross-Steinmeyer K., Stapleton P.L., Liu F., Tracy J.H., Bammler T.K., Quigley S.D., Farin F.M., Buhler D.R., Safe S.H., Strom S.C., and Eaton D.L. Phytochemical-induced changes in gene expression of carcinogen-metabolizing enzymes in cultured human primary hepatocytes. Xenobiotica 34 (2004) 619-632
13. Hertog M.G.L., Hollman P.C.H., and Katan M.B. Content of potentially anticarcinogenic flavonoids of 28 vegetables and 9 fruits commonly consumed in the Netherlands. J. Agric. Food Chem. 40 (1992) 2379-2383
14. James M.O. Polychlorinated biphenyls: metabolism and metabolites. In: Robertson L.W., and Hansen L.G. (Eds). PCBs-Recent Advances in Environmental Toxicology and Health Effects (2001), University of Kentucky Press, Lexington 35-46
15. James M.O., Altman A.H., Morris K., Kleinow K.M., and Tong Z. Dietary modulation of phase 1 and phase 2 activities with benzo(α)pyrene and related compounds in the intestine but not the liver of the channel catfish, Ictalurus punctatus. Drug Metab. Dispos. 25 (1997) 346-354
16. Kaminsky L.S., Kennedy M.W., Adams S.M., and Guengerich F.P. Metabolism of dichlorobiphenyls by highly purified isozymes of rat liver cytochrome P-450. Biochemistry 20 (1981) 7379-7384
17. Kester M.H., Bulduk S., Tibboel D., Meinl W., Glatt H., Falany C.N., Coughtrie M.W., Bergman A., Safe S.H., Kuiper G.G., Schuur A.G., Brouwer A., and Visser T.J. Potent inhibition of estrogen sulfotransferase by hydroxylated PCB metabolites: a novel pathway explaining the estrogenic activity of PCBs. Endocrinology 141 (2000) 1897-1900
18. Komoroski B.J., Zhang S., Cai H., Hutzler J.M., Frye R., Tracy T.S., Strom S.C., Lehmann T., Ang C.Y., Cui Y.Y., and Venkataramanan R. Induction and inhibition of cytochromes P450 by the St. John's wort constituent hyperforin in human hepatocyte cultures. Drug Metab. Dispos. 32 (2004) 512-518
19. Letcher R.J., Wehler E.K., and Bergman A. Methyl sulfone and hydroxylated metabolites of polychlorinated biphenyls. In: Paasiverta J. (Ed). New Types of Persistent Halogenated Compounds (2000), Springer-Verlag, Berlin 157-317
20. Liu Y., Apak T.I., Lehmler H.J., Robertson L.W., and Duffel M.W. Hydroxylated polychlorinated biphenyls are substrates and inhibitors of human hydroxysteroid sulfotransferase SULT2A1. Chem. Res. Toxicol. 19 (2006) 1420-1425
21. Machala M., Blaha L., Lehmler H.J., Pliskova M., Majkova Z., Kapplova P., Sovadinova I., Vondracek J., Malmberg T., and Robertson L.W. Toxicity of hydroxylated and quinoid PCB metabolites: inhibition of gap junctional intercellular communication and activation of aryl hydrocarbon and estrogen receptors in hepatic and mammary cells. Chem. Res. Toxicol. 17 (2004) 340-347
22. Manach C., Williamson G., Morand C., Scalbert A., and Remesy C. Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. Am. J. Clin. Nutr. 81 (2005) 230S-242S
23. Mathews H.B., and Anderson M.W. Effect of chlorination on the distribution and excretion of polychlorinated biphenyls. Drug Metab. Dispos. 3 (1975) 371-380
24. Mizuma T., and Awazu S. Dietary polyphenols (-)-epicatechin and chrysin inhibit intestinal glucuronidation metabolism to increase drug absorption. J. Pharm. Sci. 93 (2004) 2407-2410
25. Moon Y.J., Wang X., and Morris M.E. Dietary flavonoids: effects on xenobiotic and carcinogen metabolism. Toxicol. In Vitro 20 (2006) 187-210
26. Naganuma M., Saruwatari A., Okamura S., and Tamura H. Turmeric and curcumin modulate the conjugation of 1-naphthol in Caco-2 cells. Biol. Pharm. Bull. 29 (2006) 1476-1479
27. Nakajima M., Yoshida R., Shimada N., Yamazaki H., and Yokoi T. Inhibition and inactivation of human cytochrome P450 isoforms by phenethyl isothiocyanate. Drug Metab. Dispos. 29 (2001) 1110-1113
28. NRC. Nutrient Requirements of Warm-water Fishes and Shellfishes (1983), National Research Council, National Academy Press, Washington, DC
29. Sacco J.C. Phase II biotransformation of xenobiotics in polar bear (Ursus maritimus) and channel catfish (Ictalurus punctatus) (2006), University of Florida, FL, United States
30. Sandau C.D., Ayotte P., Dewailly E., Duffe J., and Norstrom R.J. Analysis of hydroxylated metabolites of PCBs (OH-PCBs) and other chlorinated phenolic compounds in whole blood from Canadian inuit. Environ. Health Perspect. 108 (2000) 611-616
31. Schuur A.G., Brouwer A., Bergman A., Coughtrie M.W., and Visser T.J. Inhibition of thyroid hormone sulfation by hydroxylated metabolites of polychlorinated biphenyls. Chem. Biol. Interact. 109 (1998) 293-297
32. Slaga T.J., Thompson S., Berry D.L., Digiovanni J., Juchau M.R., and Viaje A. The effects of benzoflavones on polycyclic hydrocarbon metabolism and skin tumor initiation. Chem. Biol. Interact. 17 (1977) 297-312
33. Tampal N., Lehmler H.J., Espandiari P., Malmberg T., and Robertson L.W. Glucuronidation of hydroxylated polychlorinated biphenyls (PCBs). Chem. Res. Toxicol. 15 (2002) 1259-1266
34. Thapliyal R., and Maru G.B. Inhibition of cytochrome P450 isozymes by curcumins in vitro and in vivo. Food Chem. Toxicol. 39 (2001) 541-547
35. van den Hurk P., Kubiczak G.A., Lehmler H.J., and James M.O. Hydroxylated polychlorinated biphenyls as inhibitors of the sulfation and glucuronidation of 3-hydroxy-benzo[a]pyrene. Environ. Health Perspect. 110 (2002) 343-348
36. Walle T. Absorption and metabolism of flavonoids. Free Radic. Biol. Med. 36 (2004) 829-837
37. Wang L.Q., and James M.O. Inhibition of sulfotransferases by xenobiotics. Curr. Drug Metab. 7 (2006) 83-104
38. Wang L.Q., Lehmler H.J., Robertson L.W., Falany C.N., and James M.O. In vitro inhibition of human hepatic and cDNA-expressed sulfotransferase activity with 3-hydroxybenzo[a]pyrene by polychlorobiphenylols. Environ. Health Perspect. 113 (2005) 680-687
39. Wang L.Q., Lehmler H.J., Robertson L.W., and James M.O. Polychlorobiphenylols are selective inhibitors of human phenol sulfotransferase 1A1 with 4-nitrophenol as a substrate. Chem. Biol. Interact. 159 (2006) 235-246
40. Yoshimura H., Yonemoto Y., Yamada H., Koga N., Oguri K., and Saeki S. Metabolism in vivo of 3,4,3′,4′-tetrachlorobiphenyl and toxicological assessment of the metabolites in rats. Xenobiotica 17 (1987) 897-910
41. Zhu B.T., Taneja N., Loder D.P., Balentine D.A., and Conney A.H. Effects of tea polyphenols and flavonoids on liver microsomal glucuronidation of estradiol and estrone. J. Steroid Biochem. Mol. Biol. 64 (1998) 207-215