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Xenobiotica
the fate of foreign compounds in biological systems
Volume 48, 2018 - Issue 4
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General Xenobiochemistry

Glucuronidation of icaritin by human liver microsomes, human intestine microsomes and expressed UDP-glucuronosyltransferase enzymes: identification of UGT1A3, 1A9 and 2B7 as the main contributing enzymes

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Pages 357-367 | Received 22 Mar 2017, Accepted 21 Apr 2017, Published online: 15 May 2017

References

  • Bhasker CR, McKinnon W, Stone A, et al. (2010). Genetic polymorphism of UDP-glucuronosyltransferase 2B7 (UGT2B7) at amino acid 268: ethnic diversity of alleles and potential clinical significance. Pharmacogenetics 10:679–85
  • Chang Q, Wang GN, Li Y, et al. (2012). Oral absorption and excretion of icaritin, an aglycone and also active metabolite of prenylflavonoids from the Chinese medicine Herba Epimedii in rats. Phytomedicine 19:1024–8
  • Chen SH, Lei M, Xie XH, et al. (2013). PLGA/TCP composite scaffold incorporating bioactive phytomolecule icaritin for enhancement of bone defect repair in rabbits. Acta Biomater 9:6711–22
  • Chen Y, Zhao YH, Jia XB, et al. (2008). Intestinal absorption mechanisms of prenylated flavonoids present in the heat-processed Epimedium koreanum Nakai (Yin Yanghuo). Pharm Res-Dordr 25:2190–9
  • Cui L, Xu F, Jiang J, et al. (2014). Identification of metabolites of epimedin A in rats using UPLC/Q–TOF–MS. Chromatographia 77:1223–34
  • Evans WE, Relling MV. (1999). Pharmacogenomics: translating functional genomics into rational therapeutics. Science 5439:487–91
  • Hutzler JM, Tracy TS. (2002). Atypical kinetic profiles in drug metabolism reactions. Drug Metab Dispos 30:355–62
  • Jiang MC, Chen XH, Zhao X, et al. (2016). Involvement of IGF-1 receptor signaling pathway in the neuroprotective effects of Icaritin against MPP(+)-induced toxicity in MES23.5 cells. Eur J Pharmacol 786:53–9
  • Jiang W, Xu B, Wu B, et al. (2012). UDP-glucuronosyltransferase (UGT) 1A9-overexpressing HeLa cells is an appropriate tool to delineate the kinetic interplay between breast cancer resistance protein (BRCP) and UGT and to rapidly identify the glucuronide substrates of BCRP. Drug Metab Dispos 40:336–45
  • Jin Y, Wu CS, Zhang JL, et al. (2013). A new strategy for the discovery of epimedium metabolites using high-performance liquid chromatography with high resolution mass spectrometry. Anal Chim Acta 768:111–17
  • Knights KM, Rowland A, Miners JO. (2013). Renal drug metabolism in humans: the potential for drug–endobiotic interactions involving cytochrome P450 (CYP) and UDPglucuronosyltransferase (UGT). Br J Clin Pharmacol 76:587–602
  • Liao J, Liu Y, Wu H, et al. (2016). The role of icaritin in regulating Foxp3/IL17a balance in systemic lupus erythematosus and its effects on the treatment of MRL/lpr mice. Clin Immunol 162:74–83
  • Li F, Wang S, Lu D, et al. (2016). Identification of UDP-glucuronosyltransferases 1A1, 1A3 and 2B15 as the main contributors to glucuronidation of bakuchiol, a natural biologically active compound. Xenobiotica 47:365–79
  • Li J, Liu P, Zhang R, et al. (2011). Icaritin induces cell death in activated hepatic stellate cells through mitochondrial activated apoptosis and ameliorates the development of liver fibrosis in rats. J Ethnopharmacol 137:714–23
  • Liu H, Wu Z, Ma Z, et al. (2014). Glucuronidation of macelignan by human liver microsomes and expressed UGT enzymes: identification of UGT1A1 and 2B7 as the main contributing enzymes. Biopharm Drug Dispos 35:513–24
  • Lu D, Ma Z, Zhang T, et al. (2016). Metabolism of the anthelmintic drug niclosamide by cytochrome P450 enzymes and UDP-glucuronosyltransferases: metabolite elucidation and main contributions from CYP1A2 and UGT1A1. Xenobiotica 46:1–13
  • Lu D, Liu H, Ye W, et al. (2016). Structure- and isoform-specific glucuronidation of six curcumin analogs. Xenobiotica 47:304–13
  • Mackenzie PI, Bock KW, Burchell B, et al. (2005). Nomenclature update for the mammalian UDP glycosyltransferase (UGT) gene superfamily. Pharmacogenet Genomics 15:677–85
  • Ma H, He X, Yang Y, et al. (2011). The genus Epimedium: an ethnopharmacological and phytochemical review. J Ethnopharmacol 134:519–41
  • Nagar S, Blanchard RL. (2006). Pharmacogenetics of uridine diphosphoglucuronosyltransferase (UGT) 1A family members and its role in patient response to irinotecan. Drug Metab Rev 38:393–409
  • Nakamura A, Nakajima M, Yamanaka H, et al. (2008). Expression of UGT1A and UGT2B mRNA in human normal tissues and various cell lines. Drug Metab Dispos 36:1461–4
  • Ohno S, Nakajin S. (2009). 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 37:32–40
  • Peng S, Zhang G, Zhang BT, et al. (2013). The beneficial effect of icaritin on osteoporotic bone is dependent on the treatment initiation timing in adult ovariectomized rats. Bone 55:230–40
  • Qian Q, Li SL, Sun E, et al. (2012). Metabolite profiles of icariin in rat plasma by ultra-fast liquid chromatography coupled to triple-quadrupole/time-of-flight mass spectrometry. J Pharm Biomed Anal 66:392–8
  • Ritter JK. (2000). Roles of glucuronidation and UDP-glucuronosyltransferases in xenobiotic bioactivation reactions. Chem Biol Interact 129:171–93
  • Sun F, Indran IR, Zhang ZW, et al. (2015). A novel prostate cancer therapeutic strategy using icaritin-activated arylhydrocarbon-receptor to co-target androgen receptor and its splice variants. Carcinogenesis 36:757–68
  • Sun H, Wang H, Liu H, et al. (2014). Glucuronidation of capsaicin by liver microsomes and expressed UGT enzymes: reaction kinetics, contribution of individual enzymes and marked species differences. Expert Opin Drug Metab Toxicol 10:1325–36
  • Sun H, Zhou X, Zhang X, et al. (2015). Decreased expression of multidrug resistance-associated protein 4 (MRP4/ABCC4) leads to reduced glucuronidation of flavonoids in UGT1A1-overexpressing HeLa cells: the role of futile recycling. J Agric Food Chem 63:6001–8
  • Troberg J, Jarvinen E, Ge GB, et al. (2016). UGT1A10 is a high activity and important extrahepatic enzyme: why has its role in intestinal glucuronidation been frequently underestimated? Mol Pharm. [Epub ahead of Print]. DOI: 10.1021/acs.molpharmaceut.6b00852
  • Wang C, Wu C, Zhang J, et al. (2015). Systematic considerations for a multicomponent pharmacokinetic study of Epimedii wushanensis herba: From method establishment to pharmacokinetic marker selection. Phytomedicine 22:487–97
  • Wu B, Kulkarni K, Basu S, et al. (2011). First-pass metabolism via UDPglucuronosyl transferase: a barrier to oral bioavailability of phenolics. J Pharm Sci 100:3655–81
  • Wu B, et al. (2013). Quantitative prediction of glucuronidation in humans using the in vitro- in vivo extrapolation approach. Curr Top Med Chem 13:1343–52
  • Zhao H, Fan M, Fan L, et al. (2010). Liquid chromatography-tandem mass spectrometry analysis of metabolites in rats after administration of prenylflavonoids from Epimediums. J Chromatogr B Analyt Technol Biomed Life Sci 878:1113–24
  • Zhou J, Ma YH, Zhou Z, et al. (2015). Intestinal absorption and metabolism of epimedium flavonoids in osteoporosis rats. Drug Metab Dispos 43:1590–600

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