Involvement of UDP-glucuronosyltranferases and sulfotransferases in the liver and intestinal first-pass metabolism of seven flavones in C57 mice and humans in vitro

Food and Chemical Toxicology

Volumn 50, Issue 5, 2012, Pages 1460-1467

  Tang, Lan ^a   Feng, Qian ^a   Zhao, Jie ^a   Dong, Lingna ^a   Liu, Wei ^a   Yang, Caihua ^a   Liu, Zhongqiu ^a  

^a SOUTHERN MEDICAL UNIVERSITY   (China)

Author keywords

Flavones; Glucuronidation; Intestine; Liver S9; Sulfation

Indexed keywords

3 MONOHYDROXYFLAVONE; 3,4' DIHYDROXYFLAVONE; 3,5 DIHYDROXYFLAVONE; 3,7 DIHYDROXYFLAVONE; 4' MONOHYDROXYFLAVONE; 5 MONOHYDROXYFLAVONE; 7 MONOHYDROXYFLAVONE; FLAVONE DERIVATIVE; GLUCURONOSYLTRANSFERASE; HYDROXYL GROUP; SULFOTRANSFERASE; UNCLASSIFIED DRUG;

ACCURACY; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BIOLOGICAL MODEL; CONTROLLED STUDY; CORRELATION ANALYSIS; DRUG GLUCURONIDATION; DRUG STRUCTURE; DRUG SULFATION; FIRST PASS EFFECT; HUMAN; IN VITRO STUDY; INTESTINAL FIRST PASS METABOLISM; LIVER METABOLISM; MALE; MOUSE; NONHUMAN; SPECIES DIFFERENCE;

ANIMALS; BIOTRANSFORMATION; CHROMATOGRAPHY, LIQUID; FLAVONES; GLUCURONOSYLTRANSFERASE; HUMANS; INTESTINES; LIVER; MALE; MICE; MICE, INBRED C57BL; SULFOTRANSFERASES; TANDEM MASS SPECTROMETRY;

MUS;

EID: 84862811626     PISSN: 02786915     EISSN: 18736351     Source Type: Journal    
DOI: 10.1016/j.fct.2012.01.018     Document Type: Article

References (38)

1. Akao T., Kawabata K., Yanagisawa E., Ishihara K., Mizuhara Y., Wakui Y., Sakashita Y., Kobashi K. Baicalin, the predominant flavone glucuronide of scutellariae radix, is absorbed from the rat gastrointestinal tract as the aglycone and restored to its original form. J. Pharm. Pharmacol. 2000, 52:1563-1568.
2. Benavente-Garcia O., Castillo J. Update on uses and properties of citrus flavonoids: new findings in anticancer, cardiovascular, and anti-inflammatory activity. J. Agric. Food. Chem. 2008, 56:6185-6205.
3. Birt D.F., Hendrich S., Wang W. Dietary agents in cancer prevention: flavonoids and isoflavonoids. Pharmacol. Ther. 2001, 90:157-177.
4. Brand W., Schutte M.E., Williamson G., van Zanden J.J., Cnubben N.H., Groten J.P., van Bladeren P.J., Rietjens I.M. Flavonoid-mediated inhibition of intestinal ABC transporters may affect the oral bioavailability of drugs, food-borne toxic compounds and bioactive ingredients. Biomed. Pharmacother. 2006, 60:508-519.
5. Chen J., Halls S.C., Alfaro J.F., Zhou Z., Hu M. Potential beneficial metabolic interactions between tamoxifen and isoflavones via cytochrome P450-mediated pathways in female rat liver microsomes. Pharm. Res. 2004, 21:2095-2104.
6. Chen J., Lin H., Hu M. Metabolism of flavonoids via enteric recycling: role of intestinal disposition. J. Pharmacol. Exp. Ther. 2003, 304:1228-1235.
7. Chi Y.S., Kim H.P. Suppression of cyclooxygenase-2 expression of skin fibroblasts by wogonin, a plant flavone from Scutellaria radix. Prostaglandins Leukot. Essent. Fatty Acids 2005, 72:59-66.
8. Crespy V., Morand C., Besson C., Manach C., Demigne C., Remesy C. Comparison of the intestinal absorption of quercetin, phloretin and their glucosides in rats. J. Nutr. 2001, 131:2109-2114.
9. Day A.J., Mellon F., Barron D., Sarrazin G., Morgan M.R., Williamson G. Human metabolism of dietary flavonoids: identification of plasma metabolites of quercetin. Free Radic. Res. 2001, 35:941-952.
10. de Vries J.H., Hollman P.C., Meyboom S., Buysman M.N., Zock P.L., van Staveren W.A., Katan M.B. Plasma concentrations and urinary excretion of the antioxidant flavonols quercetin and kaempferol as biomarkers for dietary intake. Am. J. Clin. Nutr. 1998, 68:60-65.
11. DuPont M.S., Day A.J., Bennett R.N., Mellon F.A., Kroon P.A. Absorption of kaempferol from endive, a source of kaempferol-3-glucuronide, in humans. Eur. J. Clin. Nutr. 2004, 58:947-954.
12. Galijatovic A., Walle U.K., Walle T. Induction of UDP-glucuronosyltransferase by the flavonoids chrysin and quercetin in Caco-2 cells. Pharm. Res. 2000, 17:21-26.
13. Hu M., Chen J., Lin H. Metabolism of flavonoids via enteric recycling: mechanistic studies of disposition of apigenin in the Caco-2 cell culture model. J. Pharmacol. Exp. Ther. 2003, 307:314-321.
14. Hu M., Roland K., Ge L., Chen J., Li Y., Tyle P., Roy S. Determination of absorption characteristics of AG337, a novel thymidylate synthase inhibitor, using a perfused rat intestinal model. J. Pharm. Sci. 1998, 87:886-890.
15. Hu M., Sinko P.J., deMeere A.L., Johnson D.A., Amidon G.L. Membrane permeability parameters for some amino acids and beta-lactam antibiotics: application of the boundary layer approach. J. Theor. Biol. 1988, 131:107-114.
16. Janisch K.M., Williamson G., Needs P., Plumb G.W. Properties of quercetin conjugates: modulation of LDL oxidation and binding to human serum albumin. Free Radic. Res. 2004, 38:877-884.
17. Jeong E.J., Jia X., Hu M. Disposition of formononetin via enteric recycling: metabolism and excretion in mouse intestinal perfusion and Caco-2 cell models. Mol. Pharm. 2005, 2:319-328.
18. Jia X., Chen J., Lin H., Hu M. Disposition of flavonoids via enteric recycling: enzyme-transporter coupling affects metabolism of biochanin A and formononetin and excretion of their phase II conjugates. J. Pharmacol. Exp. Ther. 2004, 310:1103-1113.
19. Joseph T.B., Wang S.W., Liu X., Kulkarni K.H., Wang J., Xu H., Hu M. Disposition of flavonoids via enteric recycling: enzyme stability affects characterization of prunetin glucuronidation across species, organs, and UGT isoforms. Mol. Pharm. 2007, 4:883-894.
20. Kroon P.A., Clifford M.N., Crozier A., Day A.J., Donovan J.L., Manach C., Williamson G. How should we assess the effects of exposure to dietary polyphenols in vitro?. Am. J. Clin. Nutr. 2004, 80:15-21.
21. Liu X., Tam V.H., Hu M. Disposition of flavonoids via enteric recycling: determination of the UDP-glucuronosyltransferase isoforms responsible for the metabolism of flavonoids in intact Caco-2 TC7 cells using siRNA. Mol. Pharm. 2007, 4:873-882.
22. Manach C., Donovan J.L. Pharmacokinetics and metabolism of dietary flavonoids in humans. Free Radic. Res. 2004, 38:771-785.
23. Moon J.H., Nakata R., Oshima S., Inakuma T., Terao J. Accumulation of quercetin conjugates in blood plasma after the short-term ingestion of onion by women. Am. J. Physiol. Regul. Integr. Comp. Physiol. 2000, 279:R461-467.
24. Okita J.R., Castle P.J., Okita R.T. Characterization of cytochromes P450 in liver and kidney of rats treated with di-(2-ethylhexyl)phthalate. J. Biochem. Toxicol. 1993, 8:135-144.
25. Ronis M.J., Little J.M., Barone G.W., Chen G., Radominska-Pandya A., Badger T.M. Sulfation of the isoflavones genistein and daidzein in human and rat liver and gastrointestinal tract. J. Med. Food 2006, 9:348-355.
26. Setchell K.D., Brown N.M., Desai P., Zimmer-Nechemias L., Wolfe B.E., Brashear W.T., Kirschner A.S., Cassidy A., Heubi J.E. Bioavailability of pure isoflavones in healthy humans and analysis of commercial soy isoflavone supplements. J. Nutr. 2001, 131:1362S-1375S.
27. Shia C.S., Tsai S.Y., Kuo S.C., Hou Y.C., Chao P.D. Metabolism and pharmacokinetics of 3,3',4',7-tetrahydroxyflavone (fisetin), 5-hydroxyflavone, and 7-hydroxyflavone and antihemolysis effects of fisetin and its serum metabolites. J. Agric. Food. Chem. 2009, 57:83-89.
28. Singh R., Wu B., Tang L., Liu Z., Hu M. Identification of the position of mono-O-glucuronide of flavones and flavonols by analyzing shift in online UV spectrum (lambdamax) generated from an online diode array detector. J. Agric. Food. Chem. 2010, 58:9384-9395.
29. Tang L., Singh R., Liu Z., Hu M. Structure and concentration changes affect characterization of UGT isoform-specific metabolism of isoflavones. Mol. Pharm. 2009, 6:1466-1482.
30. Tang L., Ye L., Singh R., Wu B., Lv C., Zhao J., Liu Z., Hu M. Use of glucuronidation fingerprinting to describe and predict mono- and dihydroxyflavone metabolism by recombinant UGT isoforms and human intestinal and liver microsomes. Mol. Pharm. 2010, 7:664-679.
31. Thomasset S.C., Berry D.P., Garcea G., Marczylo T., Steward W.P., Gescher A.J. Dietary polyphenolic phytochemicals-promising cancer chemopreventive agents in humans? A review of their clinical properties. Int. J. Cancer 2007, 120:451-458.
32. van der Woude H., Boersma M.G., Vervoort J., Rietjens I.M. Identification of 14 quercetin phase II mono- and mixed conjugates and their formation by rat and human phase II in vitro model systems. Chem. Res. Toxicol. 2004, 17:1520-1530.
33. Vietri M., Pietrabissa A., Spisni R., Mosca F., Pacifici G.M. 7-OH-flavone is sulfated in the human liver and duodenum, whereas 5-OH-flavone and 3-OH-flavone are potent inhibitors of SULT1A1 activity and 7-OH-flavone sulfation rate. Xenobiotica 2002, 32:563-571.
34. Wang Q., Jia R., Ye C., Garcia M., Li J., Hidalgo I.J. Glucuronidation and sulfation of 7-hydroxycoumarin in liver matrices from human, dog, monkey, rat, and mouse. In Vitro Cell. Dev. Biol. Anim. 2005, 41:97-103.
35. Wang S.W., Chen J., Jia X., Tam V.H., Hu M. Disposition of flavonoids via enteric recycling: structural effects and lack of correlations between in vitro and in situ metabolic properties. Drug Metab. Dispos. 2006, 34:1837-1848.
36. Wang S.W., Kulkarni K.H., Tang L., Wang J., Yin T., Daidoji T., Yokota H., Hu M. Disposition of flavonoids via enteric recycling: UGT1As deficiency in gunn rats is compensated by increases in UGT2Bs activities. J. Pharmacol. Exp. Ther. 2009, 329:1023-1031.
37. Zhang L., Lin G., Zuo Z. Position preference on glucuronidation of mono-hydroxylflavones in human intestine. Life Sci. 2006, 78:2772-2780.
38. Zhang L., Lin G., Zuo Z. Involvement of UDP-glucuronosyltransferases in the extensive liver and intestinal first-pass metabolism of flavonoid baicalein. Pharm. Res. 2007, 24:81-89.