Structure- and isoform-specific glucuronidation of six curcumin analogs

References

• Al Saabi A, Allorge D, Sauvage FL, et al. (2013). Involvement of UDP-glucuronosyltransferases UGT1A9 and UGT2B7 in ethanol glucuronidation, and interactions with common drugs of abuse. Drug Metab Dispos 41:568–74.
   PubMed Web of Science ®Google Scholar
• Anand P, Kunnumakkara AB, Newman RA, Aggarwal BB. (2007). Bioavailability of curcumin: Problems and promises. Mol Pharm 4:807–18.
   PubMed Web of Science ®Google Scholar
• Asai A, Miyazawa T. (2000). Occurrence of orally administered curcuminoid as glucuronide and glucuronide/sulfate conjugates in rat plasma. Life Sci 67:2785–93.
   PubMed Web of Science ®Google Scholar
• Barbier O, Turgeon D, Girard C, et al. (2000). 3′-azido-3′-deoxythimidine (AZT) is glucuronidated by human UDP-glucuronosyltransferase 2B7 (UGT2B7). Drug Metab Dispos 28:497–502.
   PubMed Web of Science ®Google Scholar
• Chen SD, Gao JT, Liu JG, et al. (2015). Five new diarylheptanoids from the rhizomes of Curcuma kwangsiensis and their antiproliferative activity. Fitoterapia 102:67–73.
   PubMed Web of Science ®Google Scholar
• Court MH, Duan SX, Guillemette C, et al. (2002). Stereoselective conjugation of oxazepam by human UDP-glucuronosyltransferases (UGTS): S-oxazepam is glucuronidated by UGT2B15, while R-oxazepam is glucuronidated by UGT2B7 and UGT1A9. Drug Metab Dispos 30:1257–65.
   PubMed Web of Science ®Google Scholar
• Diaz-Cruz MS, de Alda MJL, Lopez R, Barcelo D. (2003). Determination of estrogens and progestogens by mass spectrometric techniques (GC/MS, LC/MS and LC/MS/MS). J Mass Spectrom 38:917–23.
   PubMed Web of Science ®Google Scholar
• Du J, You T, Chen X, Zhong D. (2013). Stereoselective glucuronidation of ornidazole in humans: predominant contribution of UDP-glucuronosyltransferases 1A9 and 2B7. Drug Metab Dispos 41:1306–18.
   PubMed Web of Science ®Google Scholar
• Epstein J, Sanderson IR, Macdonald TT. (2010). Curcumin as a therapeutic agent: the evidence from in vitro, animal and human studies. Br J Nutr 103:1545–57.
   PubMed Web of Science ®Google Scholar
• Fallon JK, Neubert H, Goosen TC, Smith PC. (2013a). Targeted precise quantification of 12 human recombinant uridine-diphosphate glucuronosyl transferase 1A and 2B isoforms using nano-ultra-high-performance liquid chromatography/tandem mass spectrometry with selected reaction monitoring. Drug Metab Dispos 41:2076–80.
   PubMed Web of Science ®Google Scholar
• Fallon JK, Neubert H, Hyland R, et al. (2013b). Targeted quantitative proteomics for the analysis of 14 UGT1As and-2Bs in human liver using nanoUPLC-MS/MS with selected reaction monitoring. J Proteome Res 12:4402–13.
   PubMed Web of Science ®Google Scholar
• Gaiser BK, Lockley DJ, Staines AG, et al. (2003). Almokalant glucuronidation in human liver and kidney microsomes: evidence for the involvement of UGT1A9 and 2B7. Xenobiotica 33:1073–83.
   PubMed Web of Science ®Google Scholar
• Grosse L, Campeau AS, Caron S, et al. (2013). Enantiomer selective glucuronidation of the non-steroidal pure anti-androgen bicalutamide by human liver and kidney: role of the human UDP-glucuronosyltransferase (UGT)1A9 enzyme. Basic Clin Pharmacol Toxicol 113:92–102.
   PubMed Web of Science ®Google Scholar
• Hoehle SI, Pfeiffer E, Metzler M. (2007). Glucuronidation of curcuminoids by human microsomal and recombinant UDP-glucuronosyltransferases. Mol Nutr Food Res 51:932–8.
   PubMed Web of Science ®Google Scholar
• Hutzler JM, Tracy TS. (2002). Atypical kinetic profiles in drug metabolism reactions. Drug Metab Dispos 30:355–62.
   PubMed Web of Science ®Google Scholar
• Ilett KF, Ethell BT, Maggs JL, et al. (2002). Glucuronidation of dihydroartemisinin in vivo and by human liver microsomes and expressed UDP-glucuronosyltransferases. Drug Metab Dispos 30:1005–12.
   PubMed Web of Science ®Google Scholar
• Iyer LV, Ho MN, Shinn WM, et al. (2003). Glucuronidation of 1′-hydroxyestragole (1'-HE) by human UDP-glucuronosyltransferases UGT2B7 and UGT1A9. Toxicol Sci 73:36–43.
   PubMed Web of Science ®Google Scholar
• Karlsson ES, Johnson CH, Sarda S, et al. (2010). High-performance liquid chromatography/mass spectrometric and proton nuclear magnetic resonance spectroscopic studies of the transacylation and hydrolysis of the acyl glucuronides of a series of phenylacetic acids in buffer and human plasma. Rapid Commun Mass Spectrom 24:3043–51.
   PubMed Web of Science ®Google Scholar
• Kose LP, Gulcin I, Goren AC, et al. (2015). LC-MS/MS analysis, antioxidant and anticholinergic properties of galanga (Alpinia officinarum Hance) rhizomes. Ind Crop Prod 74:712–21.
   Web of Science ®Google Scholar
• Lee CS, Jang ER, Kim YJ, et al. (2012). Diarylheptanoid hirsutenone enhances apoptotic effect of TRAIL on epithelial ovarian carcinoma cell lines via activation of death receptor and mitochondrial pathway. Invest New Drugs 30:548–57.
   PubMed Web of Science ®Google Scholar
• Li J, Liao CR, Wei JQ, et al. (2011). Diarylheptanoids from Curcuma kwangsiensis and their inhibitory activity on nitric oxide production in lipopolysaccharide-activated macrophages. Bioorg Med Chem Lett 21:5363–9.
   PubMed Web of Science ®Google Scholar
• Liu ZF, Chiu M, Wang J, et al. (2012). Enhancement of curcumin oral absorption and pharmacokinetics of curcuminoids and curcumin metabolites in mice. Cancer Chemother Pharmacol 69:679–89.
   PubMed Web of Science ®Google Scholar
• Lu DY, Ma ZG, Zhang TP, 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.
   PubMed Web of Science ®Google Scholar
• Lu XY, Jiang KY, Han L, et al. (2015). Sulfonation of curcuminoids: characterization and contribution of individual SULT enzymes. Mol Nutr Food Res 59:634–45.
   PubMed Web of Science ®Google Scholar
• Lv HN, She GM. (2010). Naturally occurring diarylheptanoids. Nat Prod Commun 5:1687–708.
   PubMed Web of Science ®Google Scholar
• Matsuda H, Ando S, Kato T, et al. (2006). Inhibitors from the rhizomes of Alpinia officinarum on production of nitric oxide in lipopolysaccharide-activated macrophages and the structural requirements of diarylheptanoids for the activity. Bioorg Med Chem 14:138–42.
   PubMed Web of Science ®Google Scholar
• Matsuda H, Nakashima S, Oda Y, et al. (2009). Melanogenesis inhibitors from the rhizomes of Alpinia officinarum in B16 melanoma cells. Bioorg Med Chem 17:6048–53.
   PubMed Web of Science ®Google Scholar
• Metzler M, Pfeiffer E, Schulz SI, Dempe JS. (2013). Curcumin uptake and metabolism. Biofactors 39:14–20.
   PubMed Web of Science ®Google Scholar
• Nobilis M, Holcapek M, Kolarova L, et al. (2004). Identification and determination of phase II nabumetone metabolites by high-performance liquid chromatography with photodiode array and mass spectrometric detection. J Chromatogr A 1031:229–36.
   PubMed Web of Science ®Google Scholar
• Pfeiffer E, Hoehle SI, Walch SG, et al. (2007). Curcuminoids form reactive glucuronides in vitro. J Agric Food Chem 55:538–44.
   PubMed Web of Science ®Google Scholar
• Ren Q, Murphy SE, Zheng Z, Lazarus P. (2000). O-Glucuronidation of the lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) by human UDP-glucuronosyltransferases 2B7 and 1A9. Drug Metab Dispos 28:1352–60.
   PubMed Web of Science ®Google Scholar
• Riethmuller E, Toth G, Alberti A, et al. (2015). First characterisation of flavonoid- and diarylheptanoid-type antioxidant phenolics in Corylus maxima by HPLC-DAD-ESI-MS. J Pharm Biomed Anal 107:159–67.
   PubMed Web of Science ®Google Scholar
• Samokyszyn VM, Gall WE, Zawada G, et al. (2000). 4-Hydroxyretinoic acid, a novel substrate for human liver microsomal UDP-glucuronosyltransferase(s) and recombinant UGT2B7. J Biol Chem 275:6908–14.
   PubMed Web of Science ®Google Scholar
• Sato Y, Nagata M, Tetsuka K, et al. (2014). Optimized methods for targeted peptide-based quantification of human uridine 5′-diphosphate-glucuronosyltransferases in biological specimens using liquid chromatography-tandem mass spectrometry. Drug Metab Dispos 42:885–9.
   PubMed Web of Science ®Google Scholar
• Schwab N, Skopp G. (2014). Identification and preliminary characterization of UDP-glucuronosyltransferases catalyzing formation of ethyl glucuronide. Anal Bioanal Chem 406:2325–32.
   PubMed Web of Science ®Google Scholar
• Shin D, Kinoshita K, Koyama K, Takahashi K. (2002). Antiemetic principles of Alpinia officinarum. J Nat Prod 65:1315–18.
   PubMed Web of Science ®Google Scholar
• Sun H, Ma ZG, Lu DY, Wu BJ. (2015). Regio- and isoform-specific glucuronidation of psoralidin: evaluation of 3-o-glucuronidation as a functional marker for UGT1A9. J Pharma Sci 104:2369–77.
   PubMed Web of Science ®Google Scholar
• Tang G, Dong X, Huang X, et al. (2015). A natural diarylheptanoid promotes neuronal differentiation via activating Erk and Pi3k-Akt dependent pathways. Neuroscience 303:389–401.
   PubMed Web of Science ®Google Scholar
• Vareed SK, Kakarala M, Ruffin MT, et al. (2008). Pharmacokinetics of curcumin conjugate metabolites in healthy human subjects. Cancer Epidemiol Biomarkers Prev 17:1411–17.
   PubMed Web of Science ®Google Scholar
• Wu ZF, Liu HM, Wu BJ. (2015). Regioselective glucuronidation of gingerols by human liver microsomes and expressed UDP-glucuronosyltransferase enzymes: reaction kinetics and activity correlation analyses for UGT1A9 and UGT2B7. J Pharm Pharmacol 67:583–96.
   PubMed Web of Science ®Google Scholar
• Xie SG, Zeng S. (2010). Stereoselective glucuronidation of propafenone and its analogues by human recombinant UGT1A9. Chem Pharm Bull 58:879–83.
   PubMed Web of Science ®Google Scholar
• Yang Y, Kinoshita K, Koyama K, et al. (2002). Structure-antiemetic-activity of some diarylheptanoids and their analogues. Phytomedicine 9:146–52.
   PubMed Web of Science ®Google Scholar
• Yu L, Qian M, Liu Y, et al. (2010). Stereoselective metabolism of propranolol glucuronidation by human UDP-glucuronosyltransferases 2B7 and 1A9. Chirality 22:456–61.
   PubMed Web of Science ®Google Scholar