Identification of UGTs and BCRP as potential pharmacokinetic determinants of the natural flavonoid alpinetin

References

• Boersma MG, van der Woude H, Bogaards J, et al. (2002). Regioselectivity of phase II metabolism of luteolin and quercetin by UDP-glucuronosyl transferases. Chem Res Toxicol 15:662
   PubMed Web of Science ®Google Scholar
• Brand W, Boersma MG, Bik H, et al. (2010). Phase II metabolism of hesperetin by individual UDP-glucuronosyltransferases and sulfotransferases and rat and human tissue samples. Drug Metab Dispos 38:617–25.
   PubMed Web of Science ®Google Scholar
• Chen H, Mo X, Yu J, Huang Z. (2013). Alpinetin attenuates inflammatory responses by interfering toll-like receptor 4/nuclear factor kappa B signaling pathway in lipopolysaccharide-induced mastitis in mice. Int Immunopharmacol 17:26–32.
   PubMed Web of Science ®Google Scholar
• Costa A, Sarmento B, Seabra V. (2014). An evaluation of the latest in vitro tools for drug metabolism studies. Expert Opin Drug Metab Toxicol 10:103–19.
   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
• Galijatovic A, Otake Y, Walle UK, Walle T. (1999). Extensive metabolism of the flavonoid chrysin by human Caco-2 and Hep G2 cells. Xenobiotica 29:1241
   PubMed Web of Science ®Google Scholar
• Ge S, Gao S, Yin T, Hu M. (2015). Determination of pharmacokinetics of chrysin and its conjugates in wild-type FVB and Bcrp1 knockout mice using a validated LC-MS/MS method. J Agric Food Chem 63:2902–10.
   PubMed Web of Science ®Google Scholar
• Guan S, Fang B, Song B, et al. (2014). Immunosuppressive activity of alpinetin on activation and cytokines secretion of murine T lymphocytes. Immunopharmacol Immunotoxicol 36:290–6.
   PubMed Web of Science ®Google Scholar
• He X, Wei Z, Wang J, et al. (2016). Alpinetin attenuates inflammatory responses by suppressing TLR4 and NLRP3 signaling pathways in DSS-induced acute colitis. Sci Rep 6:28370
   PubMed Web of Science ®Google Scholar
• Homolya L, Váradi A, Sarkadi B. (2003). Multidrug resistance-associated proteins: export pumps for conjugates with glutathione, glucuronate or sulfate. Biofactors 17:103–14.
   PubMed Web of Science ®Google Scholar
• Hsiu SL, Tsao CW, Tsai YC, et al. (2001). Determinations of morin, quercetin and their conjugate metabolites in serum. Biol Pharm Bull 24:967–9.
   PubMed Web of Science ®Google Scholar
• Ingle JN, Buzdar AU, Schaid DJ, et al. (2010). Variation in anastrozole metabolism and pharmacodynamics in women with early breast cancer. Cancer Res 70:3278–86.
   PubMed Web of Science ®Google Scholar
• Janisch KM, Williamson G, Needs P, Plumb GW. (2004). Properties of quercetin conjugates: modulation of LDL oxidation and binding to human serum albumin. Free Radic Res 38:877–84.
   PubMed Web of Science ®Google Scholar
• Jiang W, Hu M. (2012). Mutual interactions between flavonoids and enzymatic and transporter elements responsible for flavonoid disposition via phase II metabolic pathways. RSC Adv 2:7948–63.
   PubMed Web of Science ®Google Scholar
• Jiang Z, Sang H, Fu X, et al. (2015). Alpinetin enhances cholesterol efflux and inhibits lipid accumulation in oxidized low-density lipoprotein-loaded human macrophages. Biotechnol Appl Biochem 62:840–7.
   PubMed Web of Science ®Google Scholar
• Kimura Y, Takahashi S, Yoshida I. (1968). Studies on the constituents of Alpinia. XII. On the constituents of the seeds of Alpiniakatsumadaihayata. I. The structure of cardamomin. YakugakuZasshi 88:239–41.
   PubMedGoogle Scholar
• Lee HS, Ji HY, Park EJ, Kim SY. (2007). In vitro metabolism of eupatilin by multiple cytochrome P450 and UDP-glucuronosyltransferase enzymes. Xenobiotica 37:803
   PubMed Web of Science ®Google Scholar
• Liu ZQ, Jiang ZH, Liu L, Hu M. (2006). Mechanisms responsible for poor oral bioavailability of paeoniflorin: role of intestinal disposition and interactions with sinomenine. Pharm Res 23:2768–80.
   PubMed Web of Science ®Google Scholar
• Mackenzie PI, Bock KW, Burchell B, et al. (2005). Nomenclature update for the mammalian UDP glycosyltransferase (UGT) gene superfamily. Pharmacogenet Genomics 15:677–85.
   PubMed Web of Science ®Google Scholar
• Manach C, Williamson G, Morand C, et al. (2005). Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. Am J Clin Nutr 81:230S–42S.
   PubMed Web of Science ®Google Scholar
• Oda S, Fukami T, Yokoi T, Nakajima M. (2014). Epigenetic regulation of the tissue-specific expression of human UDP-glucuronosyltransferase (UGT) 1A10. Biochem Pharmacol 87:660–7.
   PubMed Web of Science ®Google Scholar
• Quan E, Wang H, Dong D, et al. (2015). Characterization of chrysin glucuronidation in UGT1A1-overexpressing HeLa cells: elucidating the transporters responsible for efflux of glucuronide. Drug Metab Dispos 43:433–43.
   PubMed Web of Science ®Google Scholar
• Reinhardt D, Berdel D, Heimann G, et al. (1987). Steady state pharmacokinetics, metabolism and pharmacodynamics of theophylline in children after unequal twice-daily dosing of a new sustained-release formulation. Chronobiol Int 4:369–80.
   PubMed Web of Science ®Google Scholar
• Siissalo S, Laine L, Tolonen A, et al. (2010). Caco-2 cell monolayers as a tool to study simultaneous phase II metabolism and metabolite efflux of indomethacin, paracetamol and 1-naphthol. Int J Pharm 383:24–9.
   PubMed Web of Science ®Google Scholar
• Sun H, Zhou X, Zhang X, Wu B. (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.
   PubMed Web of Science ®Google Scholar
• Tang B, Du J, Wang J, et al. (2012). Alpinetin suppresses proliferation of human hepatoma cells by the activation of MKK7 and elevates sensitization to cis-diammined dichloridoplatium. Oncol Rep 27:1090–6.
   PubMed Web of Science ®Google Scholar
• Tang L, Singh R, Liu Z, Hu M. (2009). Structure and concentration changes affect characterization of UGT isoform-specific metabolism of isoflavones. Mol Pharm 6:1466
   PubMed Web of Science ®Google Scholar
• Turgeon D, Carrier JS, Chouinard S, Belanger A. (2003). Glucuronidation activity of the UGT2B17 enzyme toward xenobiotics. Drug Metab Dispos 31:670
   PubMed Web of Science ®Google Scholar
• Wang S, Zhou L, He W, Hu Z. (2007). Separation and determination of alpinetin and cardamonin by reverse micelle electrokinetic capillary chromatography. J Pharm Biomed Anal 43:1557–61.
   PubMed Web of Science ®Google Scholar
• Wang Z, Lu W, Li Y, Tang B. (2013). Alpinetin promotes Bax translocation, induces apoptosis through the mitochondrial pathway and arrests human gastric cancer cells at the G2/M phase. Mol Med Rep 7:915–20.
   PubMed Web of Science ®Google Scholar
• Williamson G, Aeberli I, Miguet L, et al. (2007). Interaction of positional isomers of quercetin glucuronides with the transporter ABCC2 (cMOAT, MRP2). Drug Metab Dispos 35:1262
   PubMed Web of Science ®Google Scholar
• Wu B, Morrow JK, Singh R, et al. (2011). Three-dimensional quantitative structure-activity relationship studies on UGT1A9-mediated 3-O-glucuronidation of natural flavonols using a pharmacophore-based comparative molecular field analysis model. J Pharmacol Exp Ther 336:403–13.
   PubMed Web of Science ®Google Scholar
• Wu L, Yang W, Zhang SN, Lu JB. (2015). Alpinetin inhibits lung cancer progression and elevates sensitization drug-resistant lung cancer cells to cis-diammined dichloridoplatium. Drug Des Devel Ther 9:6119–27.
   PubMed Web of Science ®Google Scholar
• Xu H, Kulkarni KH, Singh R, et al. (2009). Disposition of naringenin via glucuronidation pathway is affected by compensating efflux transporters of hydrophilic glucuronides. Mol Pharm 6:1703–15.
   PubMed Web of Science ®Google Scholar
• Zhang X, Dong D, Wang H, et al. (2015). Stable knock-down of efflux transporters leads to reduced glucuronidation in UGT1A1-overexpressing HeLa cells: the evidence for glucuronidation-transport interplay. Mol Pharm 12:1268–78.
   PubMed Web of Science ®Google Scholar
• Zhou GY, Wu D, Snyder B, et al. (2011). Development of indole compounds as small molecule fusion inhibitors targeting HIV-1 glycoprotein-41. J Med Chem 54:7220–31.
   PubMed Web of Science ®Google Scholar