Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 50, 2020 - Issue 8
752
Views
7
CrossRef citations to date
0
Altmetric
Xenobiotic Transporters

Metabolism and disposition of corylifol A from Psoralea corylifolia: metabolite mapping, isozyme contribution, species differences and identification of efflux transporters for corylifol A-O-glucuronide in HeLa1A1 cells

, , , , , , , & show all
Pages 997-1008 | Received 30 Dec 2019, Accepted 17 Feb 2020, Published online: 01 Apr 2020

References

  • Beutler E, Gelbart T, Demina A. (1998). Racial variability in the UDP-glucuronosyltransferase 1 (UGT1A1) promoter: a balanced polymorphism for regulation of bilirubin metabolism? Proc Natl Acad Sci USA 95:8170–4.
  • Cheung WI, Tse ML, Ngan T, et al. (2009). Liver injury associated with the use of Fructus Psoraleae (Bol-gol-zhee or Bu-gu-zhi) and its related proprietary medicine. Clin Toxicol (Phila) 47:683–5.
  • Cui Y, Taniguchi S, Kuroda T, Hatano T. (2015). Constituents of Psoralea corylifolia fruits and their effects on methicillin-resistant Staphylococcus aureus. Molecules 20:12500–11.
  • Gao Q, Xu Z, Zhao G, et al. (2016). Simultaneous quantification of 5 main components of Psoralea corylifolia L. in rats’ plasma by utilizing ultra high pressure liquid chromatography tandem mass spectrometry. J Chromatogr B 1011:128–35.
  • García-Martín E, Martínez C, Ladero JM, Agúndez J. (2006). Interethnic and intraethnic variability of CYP2C8 and CYP2C9 polymorphisms in healthy individuals. Mol Diagn Ther 10:29–40.
  • Geng JL, Dai Y, Yao ZH, et al. (2014). Metabolites profile of Xian-Ling-Gu-Bao capsule, a traditional Chinese medicine prescription, in rats by ultra performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry analysis. J Pharm Biomed Anal 96:90–103.
  • Gu X, Huang J, Zhang L, et al. (2017). Efficient discovery and capture of new neuronal nitric oxide synthase-postsynaptic density protein-95 uncouplers from herbal medicines using magnetic molecularly imprinted polymers as artificial antibodies. J Sep Sci 40:3522–34.
  • Hong X, Zheng Y, Qin Z, et al. (2017). In vitro glucuronidation of wushanicaritin by liver microsomes, intestine microsomes and expressed human UDP-glucuronosyltransferase enzymes. Int J Mol Sci 18:1983.
  • Jeong EJ, Liu X, Jia X, et al. (2005). Coupling of conjugating enzymes and efflux transporters: impact on bioavailability and drug interactions. Curr Drug Metab 6:455–68.
  • Kim DW, Seo KH, Curtis-Long MJ, et al. (2014). Phenolic phytochemical displaying SARS-CoV papain-like protease inhibition from the seeds of Psoralea corylifolia. J Enzyme Inhib Med Chem 29:59–63.
  • Klampfer L. (2006). Signal transducers and activators of transcription (STATs): novel targets of chemopreventive and chemotherapeutic drugs. Curr Cancer Drug Targets 6:561–71.
  • Lam W, Bussom S, Guan F, et al. (2010). The four-herb Chinese medicine PHY906 reduces chemotherapy-induced gastrointestinal toxicity. Sci Transl Med 2:45ra59.
  • Lee SW, Yun BR, Kim MH, et al. (2012). Phenolic compounds isolated from Psoralea corylifolia inhibit IL-6-induced STAT3 activation. Planta Med 78:903–6.
  • Li YG, Hou J, Li SY, et al. (2015). Fructus Psoraleae contains natural compounds with potent inhibitory effects towards human carboxylesterase 2. Fitoterapia 101:99–106.
  • Liu Y, Flynn TJ. (2015). CYP3A4 inhibition by Psoralea corylifolia and its major components in human recombinant enzyme, differentiated human hepatoma HuH-7 and HepaRG cells. Toxicol Rep 2:530–4.
  • Liu Z, Hu M. (2007). Natural polyphenol disposition via coupled metabolic pathways. Expert Opin Drug Metab Toxicol 3:389–406.
  • Lu D, Dong D, Liu Z, et al. (2015). Metabolism elucidation of BJ-B11 (a heat shock protein 90 inhibitor) by human liver microsomes: identification of main contributing enzymes. Expert Opin Drug Metab Toxicol 11:1029–40.
  • Lv X, Xia Y, Finel M, et al. (2019). Recent progress and challenges in screening and characterization of UGT1A1 inhibitors. Acta Pharm Sin B 9:258–78.
  • Ma S, Huang Y, Zhao Y, et al. (2016). Prenylflavone derivatives from the seeds of Psoralea corylifolia exhibited PPAR-γ agonist activity. Phytochem Lett 16:213–8.
  • Nagar S, Blanchard RL. (2006). Pharmacogenetics of uridine diphospho-glucuronosyltransferase (UGT) 1A family members and its role in patient response to irinotecan. Drug Metab Rev 38:393–409.
  • Obach RS, Reed-Hagen AE. (2002). Measurement of Michaelis constants for cytochrome P450-mediated biotransformation reactions using a substrate depletion approach. Drug Metab Dispos 30:831–7.
  • Qi C, Fu J, Zhao H, et al. (2019). Identification of UGTs and BCRP as potential pharmacokinetic determinants of the natural flavonoid alpinetin. Xenobiotica 49:276–83.
  • Qin Z, Li S, Yao Z, et al. (2018a). Chemical inhibition and stable knock-down of efflux transporters leads to reduced glucuronidation of wushanicaritin in UGT1A1-overexpressing HeLa cells: the role of breast cancer resistance protein (BCRP) and multidrug resistance-associated proteins (MRPs) in the excretion of glucuronides. Food Funct 9:1410–23.
  • Qin Z, Li S, Yao Z, et al. (2018). Metabolic profiling of corylin in vivo and in vitro. J Pharm Biomed Anal 155:157–68.
  • Qin Z, Zhang B, Yang J, et al. (2019). The efflux mechanism of fraxetin-O-glucuronides in UGT1A9-transfected HeLa cells: identification of multidrug resistance-associated proteins 3 and 4 (MRP3/4) as the important contributors. Front Pharmacol 10:496.
  • Ritter JK, Yeatman MT, Ferreira P, Owens IS. (1992). Identification of a genetic alteration in the code for bilirubin UDP-glucuronosyltransferase in the UGT1 gene complex of a Crigler-Najjar type I patient. J Clin Investig 90:150–5.
  • Song P, Yang X-Z, Yuan J-Q. (2013). Cytotoxic constituents from Psoralea corylifolia. J Asian Nat Prod Res 15:624–30.
  • Teschke R, Bahre R. (2009). Severe hepatotoxicity by Indian Ayurvedic herbal products: a structured causality assessment. Ann Hepatol 8:258–66.
  • Wang J, Jiang Z, Ji J, et al. (2012). Evaluation of hepatotoxicity and cholestasis in rats treated with EtOH extract of Fructus Psoraleae. J Ethnopharmacol 144:73–81.
  • Wang L, Hai Y, Huang N, et al. (2018). Human cytochrome P450 enzyme inhibition profile of three flavonoids isolated from Psoralea corylifolia: in silico predictions and experimental validation. New J Chem 42:10922–34.
  • Wang L, Hong X, Yao Z, et al. (2018). 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. Xenobiotica 48:357–67.
  • Wang PL, Yao ZH, Zhang FX, Shen XY, et al. (2015). Identification of metabolites of PSORALEAE FRUCTUS in rats by ultra performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry analysis. J Pharm Biomed Anal 112:23–35.
  • Wang XX, Lv X, Li SY, et al. (2015). Identification and characterization of naturally occurring inhibitors against UDP-glucuronosyltransferase 1A1 in Fructus Psoraleae (Bu-gu-zhi). Toxicol Appl Pharmacol 289:70–8.
  • Wu B, Kulkarni K, Basu S, et al. (2011). First-pass metabolism via UDP-glucuronosyltransferase: a barrier to oral bioavailability of phenolics. J Pharm Sci 100:3655–81.
  • Wu B, Dong D, Hu M, Zhang S. (2013). Quantitative prediction of glucuronidation in humans using the in vitro–in vivo extrapolation approach. Curr Top Med Chem 13:1343–52.
  • Xu J, Li M, Yao Z, et al. (2018). In vitro metabolic mapping of neobavaisoflavone in human cytochromes P450 and UDP-glucuronosyltransferase enzymes by ultra high-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry. J Pharm Biomed Anal 158:351–60.
  • Yang J, Zhang B, Qin Z, et al. (2018). Efflux excretion of bisdemethoxycurcumin‐O‐glucuronide in UGT1A1‐overexpressing HeLa cells: identification of breast cancer resistance protein (BCRP) and multidrug resistance-associated proteins 1 (MRP1) as the glucuronide transporters. BioFactors 44:558–69.
  • Yang YF, Zhang YB, Chen ZJ, et al. (2018). Plasma pharmacokinetics and cerebral nuclei distribution of major constituents of Psoraleae fructus in rats after oral administration. Phytomedicine 38:166–74.
  • Zhang B, Yang J, Qin Z, et al. (2019). Mechanism of the efflux transport of demethoxycurcumin-O-glucuronides in HeLa cells stably transfected with UDP-glucuronosyltransferase 1A1. PLoS One 14:e0217695.
  • 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.
  • Zhang Y, Chen Z, Xu X, et al. (2017). Rapid separation and simultaneous quantitative determination of 13 constituents in Psoraleae Fructus by a single marker using high-performance liquid chromatography with diode array detection. J Sep Sci 40:4191–202.
  • Zhao F, Wang J, Yang Y, et al. (2008). Effect of CYP2C19 genetic polymorphisms on the efficacy of H. pylori eradication proton pump inhibitor-based triple therapy for Helicobacter pylori eradication: a meta-analysis. Helicobacter 13:532–41.
  • Zhou QH, Zhu Y-D, Zhang F, et al. (2019). Interactions of drug-metabolizing enzymes with the Chinese herb Psoraleae Fructus. Chin J Nat Med 17:858–70.
  • Zhu L, Ge G, Liu Y, et al. (2012). Characterization of UDP-glucuronosyltransferases involved in glucuronidation of diethylstilbestrol in human liver and intestine. Chem Res Toxicol 25:2663–9.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.