Use of glucuronidation fingerprinting to describe and predict mono- and dihydroxyflavone metabolism by recombinant UGT isoforms and human intestinal and liver microsomes

Molecular Pharmaceutics

Volumn 7, Issue 3, 2010, Pages 664-679

  Tang, Lan ^a   Ye, Ling ^a   Singh, Rashim ^b   Wu, Baojian ^b   Lv, Chang ^a   Zhao, Jie ^a   Liu, Zhongqiu ^a,b   Hu, Ming ^a,b  

^a SOUTHERN MEDICAL UNIVERSITY   (China)

^b UNIVERSITY OF HOUSTON   (United States)

Author keywords

Dihydroxyflavones; Fingerprint; Microsomes; Monohydroxyflavones; UGT

Indexed keywords

2' HYDROXYFLAVONE; 3 HYDROXYFLAVONE; 3' HYDROXYFLAVONE; 3,4' DIHYDROXYFLAVONE; 3,5 DIHYDROXYFLAVONE; 3,7 DIHYDROXYFLAVONE; 4' HYDROXYFLAVONE; 6 HYDROXYFLAVONE; 7 HYDROXYFLAVONE; FLAVONE DERIVATIVE; GLUCURONOSYLTRANSFERASE; GLUCURONOSYLTRANSFERASE 1A1; GLUCURONOSYLTRANSFERASE 1A10; GLUCURONOSYLTRANSFERASE 1A7; GLUCURONOSYLTRANSFERASE 1A8; GLUCURONOSYLTRANSFERASE 1A9; GLUCURONOSYLTRANSFERASE 2B7; HYDROXYL GROUP; PRIMULETIN; UNCLASSIFIED DRUG;

ARTICLE; DRUG METABOLISM; DRUG STRUCTURE; ENZYME ACTIVITY; GLUCURONIDATION; HUMAN; HUMAN CELL; HUMAN TISSUE; HYDROGEN BOND; INTESTINE; LIQUID CHROMATOGRAPHY; LIVER MICROSOME; MASS SPECTROMETRY; PRIORITY JOURNAL; ULTRAVIOLET SPECTROSCOPY;

CHROMATOGRAPHY, LIQUID; FLAVONES; GLUCURONOSYLTRANSFERASE; HUMANS; INTESTINES; ISOENZYMES; MICROSOMES; MICROSOMES, LIVER; RECOMBINANT PROTEINS; TANDEM MASS SPECTROMETRY;

EID: 77953245569     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp900223c     Document Type: Article

References (27)

1. 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, 451-8
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, 6185-205
3. Wang, X.; Morris, M. E. Pharmacokinetics and bioavailability of the flavonoid 7,8-benzoflavone in rats J. Pharm. Sci. 2008, 97, 4546-56
4. Walle, T.; Otake, Y.; Brubaker, J. A.; Walle, U. K.; Halushka, P. V. Disposition and metabolism of the flavonoid chrysin in normal volunteers Br. J. Clin. Pharmacol. 2001, 51, 143-6
5. 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. Pharmaceutics 2007, 4, 873-82
6. Boutin, J. A.; Meunier, F.; Lambert, P. H.; Hennig, P.; Bertin, D.; Serkiz, B.; Volland, J. P. In vivo and in vitro glucuronidation of the flavonoid diosmetin in rats Drug Metab. Dispos. 1993, 21, 1157-66
7. Ross, J. A.; Kasum, C. M. Dietary flavonoids: bioavailability, metabolic effects, and safety Annu. Rev. Nutr. 2002, 22, 19-34
8. 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, 60-5
9. 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, R461-7
10. Liu, Y.; Dai, Y.; Xun, L.; Hu, M. Enteric disposition and recycling of flavonoids and ginkgo flavonoids J. Altern. Complementary Med. 2003, 9, 631-40
11. Wong, Y. C.; Zhang, L.; Lin, G.; Zuo, Z. Intestinal first-pass glucuronidation activities of selected dihydroxyflavones Int. J. Pharm. 2009, 366, 14-20
12. Zhang, L.; Lin, G.; Zuo, Z. Position preference on glucuronidation of mono-hydroxylflavones in human intestine Life Sci. 2006, 78, 2772-80
13. Tang, L.; Singh, R.; Liu, Z.; Hu, M. Structure and Concentration Changes Affect Characterization of UGT Isoform-Specific Metabolism of Isoflavones Mol. Pharmaceutics 2009, 6, 1466-82
14. Lee, H. S.; Ji, H. Y.; Park, E. J.; Kim, S. Y. In vitro metabolism of eupatilin by multiple cytochrome P450 and UDP-glucuronosyltransferase enzymes Xenobiotica 2007, 37, 803-17
15. 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. Pharmaceutics 2007, 4, 883-94
16. Liu, Y.; Hu, M. Absorption and metabolism of flavonoids in the caco-2 cell culture model and a perused rat intestinal model Drug Metab. Dispos. 2002, 30, 370-7
17. Hu, M.; Chen, J.; Tran, D.; Zhu, Y.; Leonardo, G. The Caco-2 cell monolayers as an intestinal metabolism model: metabolism of dipeptide Phe-Pro J. Drug Targeting 1994, 2, 79-89
18. 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, 1837-48
19. Gibson, D. T.; Hensley, M.; Yoshioka, H.; Mabry, T. J. Formation of (+)-cis-2,3-dihydroxy-1-methylcyclohexa-4,6-diene from toluene by Pseudomonas putida Biochemistry 1970, 9, 1626-30
20. Ohno, S.; Nakajin, S. Determination of mRNA expression of human UDP-glucuronosyltransferases and application for localization in various human tissues by real-time reverse transcriptase-polymerase chain reaction Drug Metab. Dispos. 2009, 37, 32-40
21. Mackenzie, P. I.; Rogers, A.; Treloar, J.; Jorgensen, B. R.; Miners, J. O.; Meech, R. Identification of UDP glycosyltransferase 3A1 as a UDP N-acetylglucosaminyltransferase J. Biol. Chem. 2008, 283, 36205-10
22. Fallon, J. K.; Harbourt, D. E.; Maleki, S. H.; Kessler, F. K.; Ritter, J. K.; Smith, P. C. Absolute quantification of human uridine-diphosphate glucuronosyl transferase (UGT) enzyme isoforms 1A1 and 1A6 by tandem LC-MS Drug Metab. Lett. 2008, 2, 210-22
23. Zhang, L.; Zuo, Z.; Lin, G. Intestinal and hepatic glucuronidation of flavonoids Mol. Pharmaceutics 2007, 4, 833-45
24. 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, 81-9
25. Boersma, M. G.; van der Woude, H.; Bogaards, J.; Boeren, S.; Vervoort, J.; Cnubben, N. H.; van Iersel, M. L.; van Bladeren, P. J.; Rietjens, I. M. Regioselectivity of phase II metabolism of luteolin and quercetin by UDP-glucuronosyl transferases Chem. Res. Toxicol. 2002, 15, 662-70
26. 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 Radical Res. 2001, 35, 941-52
27. de Pascual-Teresa, S.; Johnston, K. L.; DuPont, M. S.; O'Leary, K. A.; Needs, P. W.; Morgan, L. M.; Clifford, M. N.; Bao, Y.; Williamson, G. Quercetin metabolites downregulate cyclooxygenase-2 transcription in human lymphocytes ex vivo but not in vivo J. Nutr. 2004, 134, 552-7