In vitro inhibition of UGT1A3, UGT1A4 by ursolic acid and oleanolic acid and drug–drug interaction risk prediction

References

• Alvarado HL, Abrego G, Garduño-Ramirez ML, et al. (2015). Design and optimization of oleanolic/ursolic acid-loaded nanoplatforms for ocular anti-inflammatory applications. Nanomedicine 11:521–30
   PubMed Web of Science ®Google Scholar
• Evans WE, Relling MV. (1999). Pharmacogenomics: translating functional genomics into rational therapeutics. Science 286:487–91
   PubMed Web of Science ®Google Scholar
• Fang ZZ, Zhang YY, Wang XL, et al. (2011). Bioactivation of herbal constituents: simple alerts in the complex system. Expert Opin Drug Metab Toxicol 7:989–1007
   PubMed Web of Science ®Google Scholar
• Gao D, Tang S, Tong Q. (2012). Oleanolic acid liposomes with polyethylene glycol modification: promising antitumor drug delivery. Int J Nanomedicine 7:3517–26
   PubMed Web of Science ®Google Scholar
• Green MD, Tephly TR. (1996). Glucuronidation of amines and hydroxylated xenobiotics and endobiotics catalyzed by expressed human UGT1.4 protein. Drug Metab Dispos 24:356–63
   PubMed Web of Science ®Google Scholar
• Hao YM. (2013). Hollow fiber solvent bar microextraction coupled with high performance liquid chromatography for research on binding between OA and UA and protein. Shanxi: Shanxi Medical University, 45–61
   Google Scholar
• Jiang LP, Zhao J, Cao YF, et al. (2014). The inhibition of the components from shengmai injection towards UDP-glucuronosyltransferase. Evid Based Complement Alternat Med 2014:594354
   PubMed Web of Science ®Google Scholar
• Jin IJ, Ko YI, Kim YM, Han SK. (1997). Solubilization of oleanolic acid and ursolic acid by cosolvency. Arch Pharm Res 20:269–74
   PubMed Web of Science ®Google Scholar
• Kaivosaari S, Finel M, Koskinen M. (2011). N-Glucuronidation of drugs and other xenobiotics by human and animal UDP-glucuronosyltransferases. Xenobiotica 41:652–69
   PubMed Web of Science ®Google Scholar
• Kiang TK, Ensom MH, Chang TK. (2005). UDP-glucuronosyltransferases and clinical drug–drug interactions. Pharmacol Ther 106:97–132
   PubMed Web of Science ®Google Scholar
• Kim KA, Lee JS, Park HJ, et al. (2004). Inhibition of cytochrome P450 activities by oleanolic acid and ursolic acid in human liver microsomes. Life Sci 74:2769–79
   PubMed Web of Science ®Google Scholar
• Lankisch TO, Gillman TC, Erichsen TJ, et al. (2008). Aryl hydrocarbon receptor-mediated regulation of the human estrogen and bile acid UDP-glucuronosyltransferase 1A3 gene. Arch Toxicol 82:573–82
   PubMed Web of Science ®Google Scholar
• Lee SY, Kim YJ, Chung SO, Park SU. (2016). Recent studies on ursolic acid and its biological and pharmacological activity. EXCLI J 15:221–8
   PubMed Web of Science ®Google Scholar
• Lee SJ, Park JB, Kim D, et al. (2015). In vitro selective inhibition of human UDP-glucuronosyltransferase (UGT) 1A4 by finasteride, and prediction of in vivo drug–drug interactions. Toxicol Lett 232:458–65
   PubMed Web of Science ®Google Scholar
• Li S, Liao X, Meng F, et al. (2014). Therapeutic role of ursolic acid on ameliorating hepatic steatosis and improving metabolic disorders in high-fat diet-induced non-alcoholic fatty liver disease rats. PLoS One 9:e86724
   PubMed Web of Science ®Google Scholar
• Liu J. (1995). Pharmacology of oleanolic acid and ursolic acid. J Ethnopharmacol 49:57–68
   PubMed Web of Science ®Google Scholar
• Liu J. (2005). Oleanolic acid and ursolic acid: Research perspectives. J Ethnopharmacol 100:92–4
   PubMed Web of Science ®Google Scholar
• Liu X, Cao YF, Ran RX, et al. (2016). New insights into the risk of phthalates: inhibition of UDP-glucuronosyltransferases. Chemosphere 144:1966–72
   PubMed Web of Science ®Google Scholar
• López-García S, Castañeda-Sanchez JI, Jiménez-Arellanes A, et al. (2015). Macrophage activation by ursolic and oleanolic acids during mycobacterial infection. Molecules 20:14348–64
   PubMed Web of Science ®Google Scholar
• Luo Y, Liu Z, Zhang X, et al. (2016). Effect of a controlled-release drug delivery system made of oleanolic acid formulated into multivesicular liposomes on hepatocellular carcinoma in vitro and in vivo. Int J Nanomedicine 11:3111–29
   PubMed Web of Science ®Google Scholar
• Meza-Junco J, Chu QS, Christensen O, et al. (2009). UGT1A1 polymorphism and hyperbilirubinemia in a patient who received sorafenib. Cancer Chemother Pharmacol 65:1–4
   PubMed Web of Science ®Google Scholar
• Obach RS, Walsky RL, Venkatakrishnan K. (2007). Mechanism-based inactivation of human cytochrome p450 enzymes and the prediction of drug–drug interactions. Drug Metab Dispos 35:246–55
   PubMed Web of Science ®Google Scholar
• Rada M, Castellano JM, Perona JS, Guinda A. (2015). GC-FID determination and pharmacokinetic studies of oleanolic acid in human serum. Biomed Chromatogr 29:1687–92
   PubMed Web of Science ®Google Scholar
• Shanmugam MK, Dai X, Kumar AP, et al. (2014). Oleanolic acid and its synthetic derivatives for the prevention and therapy of cancer: preclinical and clinical evidence. Cancer Lett 346:206–16
   PubMed Web of Science ®Google Scholar
• Tukey RH, Strassburg CP. (2000). Human UDP-glucuronosyltransferases: metabolism, expression, and disease. Annu Rev Pharmacol Toxicol 40:581–616
   PubMed Web of Science ®Google Scholar
• Uchaipichat V, Mackenzie PI, Elliot DJ, Miners JO. (2006). Selectivity of substrate (trifluoperazine) and inhibitor (amitriptyline, androsterone, canrenoic acid, hecogenin, phenylbutazone, quinidine, quinine, and sulfinpyrazone) “probes” for human UDP-glucuronosyltransferases. Drug Metab Dispos 34:449–56
   PubMed Web of Science ®Google Scholar
• Uchaipichat V, Mackenzie PI, Guo XH, et al. (2004). Human UDP-glucuronosyltransferases: isoform selectivity and kinetics of 4-methylumbelliferone and 1-naphthol glucuronidation, effects of organic solvents, and inhibition by diclofenac and probenecid. Drug Metab Dispos 32:413–23
   PubMed Web of Science ®Google Scholar
• Wang XH, Zhou SY, Qian ZZ, et al. (2013). Evaluation of toxicity and single-dose pharmacokinetics of intravenous ursolic acid liposomes in healthy adult volunteers and patients with advanced solid tumors. Expert Opin Drug Metab Toxicol 9:117–25
   PubMed Web of Science ®Google Scholar
• Williams JA, Hyland R, Jones BC, et al. (2004). Drug–drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos 32:1201–8
   PubMed Web of Science ®Google Scholar
• Xi J, Chang Q, Chan CK, et al. (2009). Formulation development and bioavailability evaluation of a self-nanoemulsified drug delivery system of oleanolic acid. AAPS PharmSciTech 10:172–82
   PubMed Web of Science ®Google Scholar
• Zhang H, Zhang HF, Chang HC, et al. (2011). Determination of protein binding rate of oleanolic acid in human plasma and serum albumin. Yao Xue Xue Bao 46:243–6
   PubMedGoogle Scholar
• Zhou J, Tracy TS, Remmel RP. (2010). Glucuronidation of dihydrotestosterone and trans-androsterone by recombinant UDP-glucuronosyltransferase (UGT) 1A4: evidence for multiple UGT1A4 aglycone binding sites. Drug Metab Dispos 38:431–40
   PubMed Web of Science ®Google Scholar
• Zhu L, Ge G, Liu Y, et al. (2012). Potent and selective inhibition of magnolol on catalytic activities of UGT1A7 and 1A9. Xenobiotica 42:1001–8
   PubMed Web of Science ®Google Scholar
• Zucker SD, Qin X, Rouster SD, et al. (2001). Mechanism of indinavir-induced hyperbilirubinemia. Proc Natl Acad Sci USA 98:12671–6
   PubMed Web of Science ®Google Scholar