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Xenobiotica
the fate of foreign compounds in biological systems
Volume 50, 2020 - Issue 10
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General Xenobiochemistry

Inhibition of UDP-glucuronosyltransferases by different furoquinoline alkaloids

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Pages 1170-1179 | Received 06 Mar 2020, Accepted 21 Apr 2020, Published online: 05 May 2020

References

  • An FF, Liu YC, Zhang WW, et al. (2013). Dihydroartemisinine enhances dictamnine-induced apoptosis via a caspase dependent pathway in human lung adenocarcinoma A549 cells. Asian Pac J Cancer Prev 14:5895–900.
  • Barrett KG, Fang H, Cukovic D, et al. (2015). Upregulation of UGT2B4 expression by 3’-phosphoadenosine-5’-phosphosulfate synthase knockdown: implications for coordinated control of bile acid conjugation. Drug Metabol Disposition: Biol Fate of Chem 43:1061–70.
  • Basco LK, Mitaku S, Skaltsounis AL, et al. (1994). In vitro activities of furoquinoline and acridone alkaloids against Plasmodium falciparum. Antimicrob Agents Chemother 38:1169–71.
  • Cao YF, Du Z, Zhu ZT, et al. (2017). Inhibitory effects of fifteen phthalate esters in human cDNA-expressed UDP-glucuronosyltransferase supersomes. Chemosphere 185:983–90.
  • Chen DW, Du Z, Zhang CZ, et al. (2018). The inhibition of UDP-glucuronosyltransferases (UGTs) by tetraiodothyronine (T4) and triiodothyronine (T3). Xenobiotica 48:250–7.
  • Court MH, Hao Q, Krishnaswamy S, et al. (2004). Interindividual variability in acetaminophen glucuronidation by human liver microsomes: identification of relevant acetaminophen UDP-glucuronosyltransferase isoforms. J Pharmacol Experimental Therap 310:656–1006.
  • Cui K, Sun S, Wang P, et al. (2017). A novel UPLC-MS/MS method for simultaneous determination of 10 effective constituents in the Jixingshizhen preparation. Biomed Chromatogr 31:e3854.
  • Dergal JM, Gold JL, Laxer DA, et al. (2002). Potential interactions between herbal medicines and conventional drug therapies used by older adults attending a memory clinic. Drugs & Aging 19:879–86.
  • Douros A, Bronder E, Andersohn F, et al. (2016). Herb-induced liver injury in the Berlin Case-Control Surveillance Study. Int J Mol Sci 17:114.
  • Gao WF, Li YX, Zhang WH, et al. (2019). Comparison of the inhibition potential of parthenolide (PTL) and micheliolide (MCL) on various UDP-Glucuronosyltransferase (UGT) Isoforms. Xenobiotica 49:1158–21.
  • Gurley BJ, Swain A, Hubbard MA, et al. (2008). Clinical assessment of CYP2D6-mediated herb-drug interactions in humans: effects of milk thistle, black cohosh, goldenseal, kava kava, St. John’s wort, and Echinacea. Molecular Nutrition & Food Research 52:755–63.
  • House L, Ramirez J, Seminerio M, et al. (2015). In vitro glucuronidation of aprepitant: a moderate inhibitor of UGT2B7. Xenobiotica 45:990–8.
  • Huang A, Xu H, Zhan R, et al. (2017). Metabolic profile of skimmianine in rats determined by ultra-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry. Molecules 22:489.
  • Ilett KF, Ethell BT, Maggs JL, et al. (2002). Glucuronidation of dihydroartemisinin in vivo and by human liver microsomes and expressed UDP-glucuronosyltransferases. Drug Metabol Disposition: Biol Fate Chem 30:1005–12.
  • Jansen O, Akhmedjanova V, Angenot L, et al. (2006). Screening of 14 alkaloids isolated from Haplophyllum A. Juss. for their cytotoxic properties. J Ethnopharmacol 105:241–5.
  • Kiang TK, Ensom MH, Chang TK. (2005). UDP-glucuronosyltransferases and clinical drug-drug interactions. Pharmacol Ther 106:97–132.
  • Knights KM, Rowland A, Miners JO. (2013). Renal drug metabolism in humans: the potential for drug-endobiotic interactions involving cytochrome P450 (CYP) and UDP-glucuronosyltransferase (UGT). Br J Clin Pharmacol 76:587–602.
  • Knights KM, Spencer SM, Fallon JK, et al. (2016). Scaling factors for the in vitro-in vivo extrapolation (IV-IVE) of renal drug and xenobiotic glucuronidation clearance. Br J Clin Pharmacol 81:1153–64.
  • Kouam ADK, Bissoue AN, Tcho AT, et al. (2017). Antimicrobial furoquinoline alkaloids from Vepris lecomteana (Pierre) Cheek & T. Heller (Rutaceae). Molecules 23:13.
  • Krishnaswamy S, Duan SX, Von Moltke LL, et al. (2003). Validation of serotonin (5-hydroxtryptamine) as an in vitro substrate probe for human UDP-glucuronosyltransferase (UGT) 1A6. Drug Metabol Disposition: Biol Fate Chem 31:133–9.
  • Li S, Yu Y, Jin Z, et al. (2019). Prediction of pharmacokinetic drug-drug interactions causing atorvastatin-induced rhabdomyolysis using physiologically based pharmacokinetic modelling. Biomed Pharmacother 119:109416.
  • Li S-N, Cao Y-F, Sun X-Y, et al. (2018). Hydroxy metabolites of polychlorinated biphenyls (OH-PCBs) exhibit inhibitory effects on UDP-glucuronosyltransferases (UGTs). Chemosphere 212:513–22.
  • Li ZQ, Jiang LL, Zhao DS, et al. (2018). The modulatory role of CYP3A4 in dictamnine-induced hepatotoxicity. Front Pharmacol 9:1033.
  • Lin JH, Lu AY. (1997). Role of pharmacokinetics and metabolism in drug discovery and development. Pharmacol Rev 49:403–49.
  • Lin YJ, Liang WM, Chen CJ, et al. (2019). Network analysis and mechanisms of action of Chinese herb-related natural compounds in lung cancer cells. Phytomedicine 58:152893.
  • Liu Y, Ramirez J, Ratain MJ. (2011). Inhibition of paracetamol glucuronidation by tyrosine kinase inhibitors. Br J Clin Pharmacol 71:917–20.
  • Liu Y, Wei K, Yang J. (2011). 4,8-Dimeth-oxy-furo[2,3-b]quinoline (γ-fagarine). Acta Crystallographica. Section E, Struct Rep Online 67:o1907.
  • Liu YQ, Yuan LM, Gao ZZ, et al. (2016). Dimerization of human uridine diphosphate glucuronosyltransferase allozymes 1A1 and 1A9 alters their quercetin glucuronidation activities. Sci Rep 6:23763.
  • Lu Y, Zhu J, Chen X, et al. (2009). Identification of human UDP-glucuronosyltransferase isoforms responsible for the glucuronidation of glycyrrhetinic acid. Drug Metab Pharmacokinet 24:523–8.
  • Martignoni E, Cosentino M, Ferrari M, et al. (2005). Two patients with COMT inhibitor-induced hepatic dysfunction and UGT1A9 genetic polymorphism. Neurology 65:1820–2.
  • Meng Q, Liu K. (2015). Pharmacokinetic interactions between herbal medicines and prescribed drugs: focus on drug metabolic enzymes and transporters. Curr Drug Metab 15:791–807.
  • Michael JP. (2004). Quinoline, quinazoline and acridone alkaloids. Cheminform 35:650–68.
  • Nam KW, Je KH, Shin YJ, et al. (2005). Inhibitory effects of furoquinoline alkaloids from Melicope confusa and Dictamnus albus against human phosphodiesterase 5 (hPDE5A) in vitro. Arch Pharm Res 28:675–9.
  • Peer CJ, Sissung TM, Kim A, et al. (2012). Sorafenib is an inhibitor of UGT1A1 but is metabolized by UGT1A9: implications of genetic variants on pharmacokinetics and hyperbilirubinemia. Clin Cancer Res 18:2099–107.
  • Posadzki P, Watson LK, Ernst E. (2013). Adverse effects of herbal medicines: an overview of systematic reviews. Clin Med 13:7–12.
  • Rasamison VE, Brodie PJ, Merino EF, et al. (2016). Furoquinoline alkaloids and methoxyflavones from the stem bark of Melicope madagascariensis (Baker) T.G. Hartley. Nat Prod Bioprospect 6:261–5.
  • Shi F, Pan H, Cui B, et al. (2019). Dictamnine-induced hepatotoxicity in mice: the role of metabolic activation of furan. Toxicol Appl Pharmacol 364:68–76.
  • Sun Z, Wu Y, Liu S, et al. (2018). Effects of panax notoginseng saponins on esterases responsible for aspirin hydrolysis in vitro. Int J Mol Sci 19:3144.
  • Tang KSC, Konczak I, Zhao J. (2017). Phenolic compounds of the Australian native herb Prostanthera rotundifolia and their biological activities. Food Chem 233:530–9.
  • van den Berg JP, Vereecke HEM, Proost JH, et al. (2017). Pharmacokinetic and pharmacodynamic interactions in anaesthesia. A review of current knowledge and how it can be used to optimize anaesthetic drug administration. Br J Anaesth 118:44–57.
  • Wang L, Kong W, Yang M, et al. (2015). Safety issues and new rapid detection methods in traditional Chinese medicinal materials. Acta Pharmaceutica Sinica. B 5:38–46.
  • Wang P, Zhao Y, Zhu Y, et al. (2016). Metabolism of dictamnine in liver microsomes from mouse, rat, dog, monkey, and human. J Pharma Biomed Anal 119:166–74.
  • Wu L, Chen Y, Liu H, et al. (2018). Emodin-induced hepatotoxicity was exacerbated by probenecid through inhibiting UGTs and MRP2. Toxicol Appl Pharmacol 359:91–101.
  • Wu T-S, Li C-Y, Leu Y-L, et al. (1999). ChemInform abstract: limonoids and alkaloids of the root bark of Dictamnus angustifolius. Phytochemistry 50:509–12.
  • Yang B, Lee HB, Kim S, et al. (2017). Decoction of Dictamnus Dasycarpus Turcz. Root bark ameliorates skin lesions and inhibits inflammatory reactions in mice with contact dermatitis. Pharmacogn Mag 13:483–7.
  • Zhang H, Zhao Z, Wang T, et al. (2016). Inhibition of UDP-glucuronosyltransferase (UGT) isoforms by arctiin and arctigenin. Phytother Res 30:1189–96.
  • Zhang M, Long Y, Sun Y, et al. (2011). Evidence for the complementary and synergistic effects of the three-alkaloid combination regimen containing berberine, hypaconitine and skimmianine on the ulcerative colitis rats induced by trinitrobenzene-sulfonic acid. Euro J Pharmacol 651:187–96.
  • Zhang M, Wang J, Zhu L, et al. (2017). Zanthoxylum bungeanum Maxim. (Rutaceae): a systematic review of its traditional uses, botany, phytochemistry, pharmacology, pharmacokinetics, and toxicology. Int J Mol Sci 18:2172.
  • Zhang N, Liu Y, Jeong H. (2015). Drug-drug interaction potentials of tyrosine kinase inhibitors via inhibition of UDP-glucuronosyltransferases. Sci Rep 5:17778.
  • Zhang Y, Hou J, Feng F, et al. (2017). Genetic polymorphisms in human UDP-glucuronosyltransferases 1A7 and the risk of gastrointestinal carcinomas: a systematic review and network meta-analysis. Oncotarget 8:66371–81.
  • Zhang Z, Ma G, Xue C, et al. (2019). Establishment of rat liver microsome-hydrogel system for in vitro phase II metabolism and its application to study pharmacological effects of UGT substrates. Drug Metab Pharmacokinet 34:141–7.
  • Zheng SY, Shen W, Peng YM, et al. (2018). Treatment of severe rash caused by crizotinib with both traditional Chinese medicine and Western medicine: two case reports and literature review. Medicine 97:e13088.
  • Zhou SF, Zhou ZW, Li CG, et al. (2007). Identification of drugs that interact with herbs in drug development. Drug Discov Today 12:664–73.

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