Evaluation of MTBH, a novel hesperetin derivative, on the activity of hepatic cytochrome P450 isoform in vitro and in vivo using a cocktail method by HPLC-MS/MS

References

• Arendse LB, Blackburn JM. 2018. Effects of polymorphic variation on the thermostability of heterogenous populations of CYP3A4 and CYP2C9 enzymes in solution. Sci Rep. 8(1):11876.
   PubMedGoogle Scholar
• Bedada W, de Andrés F, Engidawork E, Hussein J, LLerena A, Aklillu E. 2018. Effects of Khat (Catha edulis) use on catalytic activities of major drug-metabolizing cytochrome P450 enzymes and implication of pharmacogenetic variations. Sci Rep. 8(1):12726.
   PubMedGoogle Scholar
• Brantley SJ, Argikar AA, Lin YS, Nagar S, Paine MF. 2014. Herb-drug interactions: challenges and opportunities for improved predictions. Drug Metab Dispos. 42(3):301–317.
   PubMed Web of Science ®Google Scholar
• Cao M, Feng Y, Zhang Y, Kang W, Lian K, Ai L. 2018. Studies on the metabolism and degradation of vancomycin in simulated in vitro and aquatic environment by UHPLC-Triple-TOF-MS/MS. Sci Rep. 8(1):15471.
   PubMedGoogle Scholar
• Carballo-Villalobos AI, Gonzalez-Trujano ME, Pellicer F, Lopez-Munoz FJ. 2016. Antihyperalgesic effect of hesperidin improves with diosmin in experimental neuropathic pain. Biomed Res Int. 2016:8263463.
   PubMed Web of Science ®Google Scholar
• Castiblanco LF, Triplett LR, Sundin GW. 2018. Regulation of effector delivery by type III secretion chaperone proteins in Erwinia amylovora. Front Microbiol. 9:146.
   PubMed Web of Science ®Google Scholar
• Chen J-J, Zhang J-X, Zhang X-Q, Qi M-J, Shi M-Z, Yang J, Zhang K-Z, Guo C, Han Y-L. 2017a. Effects of diosmetin on nine cytochrome P450 isoforms, UGTs and three drug transporters in vitro. Toxicol Appl Pharmacol. 334:1–7.
   PubMed Web of Science ®Google Scholar
• Chen R, Li L, Shen C, Huang C, Ma T, Meng X, Qian Z, Li Y, Li J. 2017b. Intestinal transport of HDND-7, a novel hesperetin derivative, in in vitro MDCK cell and in situ single-pass intestinal perfusion models. Xenobiotica. 47(8):719–730.
   PubMed Web of Science ®Google Scholar
• Chinni S, Dubala A, Kosaraju J, Khatwal RB, Satish Kumar MN, Kannan E. 2014. Effect of crude extract of Eugenia jambolana Lam. on human cytochrome P450 enzymes. Phytother Res. 28(11):1731–1734.
   PubMed Web of Science ®Google Scholar
• Choi YH. 2020. Interpretation of drug interaction using systemic and local tissue exposure changes. Pharmaceutics. 12(5):417.
   Web of Science ®Google Scholar
• Ding H-W, Huang A-L, Zhang Y-L, Li B, Huang C, Ma T-T, Meng X-M, Li J. 2017. Design, synthesis and biological evaluation of hesperetin derivatives as potent anti-inflammatory agent. Fitoterapia. 121:212–222.
   PubMed Web of Science ®Google Scholar
• Dong Z, Zhuang Q, Ning M, Wu S, Lu L, Wan X. 2020. Palmitic acid stimulates NLRP3 inflammasome activation through TLR4-NF-κB signal pathway in hepatic stellate cells. Ann Transl Med. 8(5):168.
   PubMed Web of Science ®Google Scholar
• Ferraz CR, Carvalho TT, Manchope MF, Artero NA, Rasquel-Oliveira FS, Fattori V, Casagrande R, Verri WA. 2020. Therapeutic potential of flavonoids in pain and inflammation: mechanisms of action, pre-clinical and clinical data, and pharmaceutical development. Molecules. 25(3):762.
   PubMed Web of Science ®Google Scholar
• Frye RF. 2004. Probing the world of cytochrome P450 enzymes. Mol Interv. 4(3):157–162.
   PubMed Web of Science ®Google Scholar
• Guengerich FP. 2019. Cytochrome P450 research and The Journal of Biological Chemistry. J Biol Chem. 294(5):1671–1680.
   PubMed Web of Science ®Google Scholar
• Hermann R, Karlsson MO, Novakovic AM, Terranova N, Fluck M, Munafo A. 2019. The clinical pharmacology of cladribine tablets for the treatment of relapsing multiple sclerosis. Clin Pharmacokinet. 58(3):283–297.
   PubMed Web of Science ®Google Scholar
• Jaeger BN, Parylak SL, Gage FH. 2018. Mechanisms of dietary flavonoid action in neuronal function and neuroinflammation. Mol Aspects Med. 61:50–62.
   PubMed Web of Science ®Google Scholar
• Lang J, Li W, Zhao J, Wang K, Chen D. 2017. Inhibitory effects of curculigoside on human liver cytochrome P450 enzymes. Xenobiotica. 47(10):849–855.
   PubMed Web of Science ®Google Scholar
• Lu H. 2016. Crosstalk of HNF4α with extracellular and intracellular signaling pathways in the regulation of hepatic metabolism of drugs and lipids. Acta Pharm Sin B. 6(5):393–408.
   PubMed Web of Science ®Google Scholar
• Ma Y-L, Zhao F, Yin J-T, Liang C-J, Niu X-L, Qiu Z-H, Zhang L-T. 2019. Two approaches for evaluating the effects of galangin on the activities and mRNA expression of seven CYP450. Molecules. 24(6):1171.
   Web of Science ®Google Scholar
• Peng HM, Auchus RJ. 2014. Two surfaces of cytochrome b5 with major and minor contributions to CYP3A4-catalyzed steroid and nifedipine oxygenation chemistries. Arch Biochem Biophys. 541:53–60.
   PubMed Web of Science ®Google Scholar
• Perez-Vizcaino F, Fraga CG. 2018. Research trends in flavonoids and health. Arch Biochem Biophys. 646:107–112.
   PubMed Web of Science ®Google Scholar
• Qin S, Eugene AR, Liu D, Zhang L, Neavin D, Biernacka JM, Yu J, Weinshilboum RM, Wang L. 2020. Dual roles for the TSPYL family in mediating serotonin transport and the metabolism of selective serotonin reuptake inhibitors in patients with major depressive disorder. Clin Pharmacol Ther. 107(3):662–670.
   PubMed Web of Science ®Google Scholar
• Quintieri L, Bortolozzo S, Stragliotto S, Moro S, Pavanetto M, Nassi A, Palatini P, Floreani M. 2010. Flavonoids diosmetin and hesperetin are potent inhibitors of cytochrome P450 2C9-mediated drug metabolism in vitro. Drug Metab Pharmacokinet. 25(5):466–476.
   PubMed Web of Science ®Google Scholar
• Rajnarayana K, Venkatesham A, Krishna DR. 2007. Bioavailability of diclofenac sodium after pretreatment with diosmin in healthy volunteers. Drug Metabol Drug Interact. 22(2–3):165–174.
   PubMedGoogle Scholar
• Shen C, Qian Z, Chen R, Meng X, Hu T, Chen Z, Li Y, Huang C, Hu C, Li J, et al. 2016. Single dose oral and intravenous pharmacokinetics and tissue distribution of a novel hesperetin derivative MTBH in rats. Eur J Drug Metab Pharmacokinet. 41(6):675–688.
   PubMed Web of Science ®Google Scholar
• Slamova K, Kapesova J, Valentova K. 2018. “Sweet flavonoids”: glycosidase-catalyzed modifications. Int J Mol Sci. 19(7):1–19.
   Web of Science ®Google Scholar
• Volkova M, Forstova-Krizova V, Skalova L, Trejtnar F. 2013. Modulatory effects of quercetin and rutin on the activity, expression and inducibility of CYP1A1 in intestinal HCT-8 cells. Phytother Res. 27(12):1889–1893.
   PubMed Web of Science ®Google Scholar
• Wang Q-Q, Shi J-B, Chen C, Huang C, Tang W-J, Li J. 2016. Hesperetin derivatives: synthesis and anti-inflammatory activity. Bioorg Med Chem Lett. 26(5):1460–1465.
   PubMed Web of Science ®Google Scholar
• Wu R, Xiao Z, Zhang X, Liu F, Zhou W, Zhang Y. 2018. The cytochrome P450-mediated metabolism alternation of four effective lignans from Schisandra chinensis in carbon tetrachloride-intoxicated rats and patients with advanced hepatocellular carcinoma. Front Pharmacol. 9:229.
   PubMed Web of Science ®Google Scholar
• Xu P, Marsafari M, Zha J, Koffas M. 2020a. Microbial coculture for flavonoid synthesis. Trends Biotechnol. 38(7):686–688.
   PubMed Web of Science ®Google Scholar
• Xu S, Zhang F, Chen D, Su K, Zhang L, Jiang R. 2020b. In vitro inhibitory effects of ganoderic acid A on human liver cytochrome P450 enzymes. Pharm Biol. 58(1):308–313.
   PubMed Web of Science ®Google Scholar
• Yang F, Liu L, Chen L, Liu M, Liu F, Xiong Y, Hu X, Xia C. 2018. OATP1B3 (699G > A) and CYP2C9*2, *3 significantly influenced the transport and metabolism of glibenclamide and glipizide. Sci Rep. 8(1):18063.
   PubMedGoogle Scholar
• Yao Y-M, Cao W, Cao Y-J, Cheng Z-N, Ou-Yang D-S, Liu Z-Q, Zhou H-H. 2007. Effect of sinomenine on human cytochrome P450 activity. Clin Chim Acta. 379(1–2):113–118.
   PubMed Web of Science ®Google Scholar
• Zhang H, Ya G, Rui H. 2017. Inhibitory effects of triptolide on human liver cytochrome P450 enzymes and P-glycoprotein. Eur J Drug Metab Pharmacokinet. 42(1):89–98.
   PubMed Web of Science ®Google Scholar
• Zhu LJ, Sun SS, Hu YX, Liu YF. 2018. Metabolism studies of paeoniflorin in rat liver microsomes by ultra-performance liquid chromatography coupled with hybrid quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF-MS/MS). R Soc Open Sci. 5(10):180759.
   PubMed Web of Science ®Google Scholar