Selective inhibitory effects of suberosin on CYP1A2 in human liver microsomes.
CYP1A2
competitive inhibition
human liver microsomes
reversible inhibitor
suberosin
Journal
Biopharmaceutics & drug disposition
ISSN: 1099-081X
Titre abrégé: Biopharm Drug Dispos
Pays: England
ID NLM: 7911226
Informations de publication
Date de publication:
Oct 2023
Oct 2023
Historique:
revised:
15
06
2023
received:
02
03
2023
accepted:
22
06
2023
medline:
5
10
2023
pubmed:
14
7
2023
entrez:
14
7
2023
Statut:
ppublish
Résumé
Suberosin is a natural phytoconstituent isolated from Citropsis articulata, especially employed for its anticoagulant properties. Although metabolic studies assessing suberosin have been conducted, it is possible interactions with drugs and food have not yet been investigated. In the present study, we analyzed the selective inhibitory effects of suberosin on cytochrome P450 (CYP) enzymes using a cocktail probe assay. Various concentrations of suberosin (0-50 μM) were incubated with isoform-specific CYP probes in human liver microsomes (HLMs). We found that suberosin significantly inhibited CYP1A2-catalyzed phenacetin O-deethylation, exhibiting IC
Substances chimiques
Cytochrome P-450 CYP1A2
EC 1.14.14.1
suberosin
0
Cytochrome P-450 Enzyme Inhibitors
0
Phenacetin
ER0CTH01H9
Cytochrome P-450 Enzyme System
9035-51-2
CYP1A2 protein, human
EC 1.14.14.1
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
365-371Subventions
Organisme : National Research Foundation of Korea
ID : 2020R1A5A2017323
Informations de copyright
© 2023 John Wiley & Sons Ltd.
Références
Abd El-Aty, A. M., Shah, S. S., Kim, B. M., Choi, J. H., Cho, H. J., Hee, Y., Chang, B. J., Shin, H. C., Lee, K. B., Shimoda, M., & Shim, J. H. (2008). In vitro inhibitory potential of decursin and decursinol angelate on the catalytic activity of cytochrome P-450 1A1/2, 2D15, and 3A12 isoforms in canine hepatic microsomes. Archives of Pharmacal Research, 31(11), 1425-1435. https://doi.org/10.1007/s12272-001-2127-9
Beltrán-Ramírez, O., Alemán-Lazarini, L., Salcido-Neyoy, M., Hernández-García, S., Fattel-Fazenda, S., Arce-Popoca, E., Arellanes-Robledo, J., García-Román, R., Vázquez-Vázquez, P., Villa-Treviño, S., & Sierra-Santoyo, A. (2008). Evidence that the anticarcinogenic effect of caffeic acid phenethyl ester in the resistant hepatocyte model involves modifications of cytochrome P450. Toxicological Sciences, 104(1), 100-106. https://doi.org/10.1093/toxsci/kfn071
Chae, J. W., Baek, I. H., & Kwon, K. I. (2012). Effect of decursin on the pharmacokinetics of theophylline and its metabolites in rats. Journal of Ethnopharmacology, 144(2), 248-254. https://doi.org/10.1016/j.jep.2012.08.046
Chen, Y., Suzuki, A., Tortorici, M. A., Garrett, M., LaBadie, R. R., Umeyama, Y., & Pithavala, Y. K. (2015). Axitinib plasma pharmacokinetics and ethnic differences. Investigational New Drugs, 33(2), 521-532. https://doi.org/10.1007/s10637-015-0214-x
Corrigan, B. W., Nicholls, B., Thakrar, B., Lam, R., Grosse, C., Alianti, J., & Palmer, J. L. (1999). Heterogeneity in systemic availability of ondansetron and granisetron following oral administration. Drug Metabolism and Disposition, 27(1), 110-112.
Di, Y. M., Li, C. G., Xue, C. C., & Zhou, S.-F. (2008). Clinical drugs that interact with St. John's Wort and implication in drug development. Current Pharmaceutical Design, 14(17), 1723-1742. https://doi.org/10.2174/138161208784746798
Fowler, S., & Zhang, H. (2008). In vitro evaluation of reversible and irreversible cytochrome P450 inhibition: Current status on methodologies and their utility for predicting drug-drug interactions. The AAPS Journal, 10(2), 410-424. https://doi.org/10.1208/s12248-008-9042-7
Gaudineau, C., Beckerman, R., Welbourn, S., & Auclair, K. (2004). Inhibition of human P450 enzymes by multiple constituents of the Ginkgo biloba extract. Biochemical and Biophysical Research Communications, 318(4), 1072-1078. https://doi.org/10.1016/j.bbrc.2004.04.139
Geissler, P. W., Nokes, K., Prince, R. J., Achieng'Odhiambo, R., Aagaard-Hansen, J., & Ouma, J. H. (2000). Children and medicines: Self-treatment of common illnesses among Luo schoolchildren in Western Kenya. Social Science and Medicine, 50(12), 1771-1783. https://doi.org/10.1016/s0277-9536(99)00428-1
Golfakhrabadi, F., Abdollahi, M., Ardakani, M. R. S., Saeidnia, S., Akbarzadeh, T., Ahmadabadi, A. N., Ebrahimi, A., Yousefbeyk, F., Hassanzadeh, A., & Khanavi, M. (2014). Anticoagulant activity of isolated coumarins (suberosin and suberenol) and toxicity evaluation of Ferulago carduchorum in rats. Pharmaceutical Biology, 52(10), 1335-1340. https://doi.org/10.3109/13880209.2014.892140
Guo, J., Zhu, X., Badawy, S., Ihsan, A., Liu, Z., Xie, C., & Wang, X. (2021). Metabolism and mechanism of human cytochrome P450 enzyme 1A2. Current Drug Metabolism, 22(1), 40-49. https://doi.org/10.2174/1389200221999210101233135
Gurley, B. J., Fifer, E. K., & Gardner, Z. (2012). Pharmacokinetic herb-drug interactions (part 2): Drug interactions involving popular botanical dietary supplements and their clinical relevance. Planta Medica, 78(13), 1490-1514. https://doi.org/10.1055/s-0031-1298331
Hanley, M. J., Cancalon, P., Widmer, W. W., & Greenblatt, D. J. (2011). The effect of grapefruit juice on drug disposition. Expert Opinion on Drug Metabolism and Toxicology, 7(3), 267-286. https://doi.org/10.1517/17425255.2011.553189
Hewitt, N. J., Gómez Lechón, M. J., Houston, J. B., Hallifax, D., Brown, H. S., Maurel, P., Kenna, J. G., Gustavsson, L., Lohmann, C., Guillouzo, A., Tuschl, G., LeCluyse, E., Groothuis, G. M. M., Hengstler, J. G., & Skonberg, C. (2007). Primary hepatocytes: Current understanding of the regulation of metabolic enzymes and transporter proteins, and pharmaceutical practice for the use of hepatocytes in metabolism, enzyme induction, transporter, clearance, and hepatotoxicity studies. Drug Metabolism Reviews, 39(1), 159-234. https://doi.org/10.1080/03602530601093489
Javidnia, E., Bahadori, M. B., Abbas-Mohammadi, M., & Pourjafar, H. (2020). Volatile and non-volatile phytochemicals from roots and leaves of Heracleum lasiopetalum and their radical scavenging ability. Biointerface Research in Applied Chemistry, 11(3), 10729-10738.
Khare, C. P. (2004). Indian herbal remedies: Rational western therapy, ayurvedic, and other traditional usage. Springer Science & Business Media.
Lang, D., Radtke, M., & Bairlein, M. (2019). Highly variable expression of CYP1A1 in human liver and impact on pharmacokinetics of riociguat and granisetron in humans. Chemical Research in Toxicology, 32(6), 1115-1122. https://doi.org/10.1021/acs.chemrestox.8b00413
Langhammer, A. J., & Nilsen, O. G. (2014). In vitro inhibition of human CYP1A2, CYP2D6, and CYP3A4 by six herbs commonly used in pregnancy. Phytotherapy Research, 28(4), 603-610. https://doi.org/10.1002/ptr.5037
Lautraite, S., Musonda, A. C., Doehmer, J., Edwards, G. O., & Chipman, J. K. (2002). Flavonoids inhibit genetic toxicity produced by carcinogens in cells expressing CYP1A2 and CYP1A1. Mutagenesis, 17(1), 45-53. https://doi.org/10.1093/mutage/17.1.45
Ma, B.-L., & Ma, Y.-M. (2016). Pharmacokinetic herb-drug interactions with traditional Chinese medicine: Progress, causes of conflicting results and suggestions for future research. Drug Metabolism Reviews, 48(1), 1-26. https://doi.org/10.3109/03602532.2015.1124888
Mali, R. S., Joshi, P. P., Sandhu, P. K., & Manekar-Tilve, A. (2002). Efficient syntheses of 6-prenylcoumarins and linear pyranocoumarins: Total synthesis of suberosin, toddaculin, O-methylapigravin (O-methylbrosiperin), O-methylbalsamiferone, dihydroxanthyletin, xanthyletin and luvangetin. Journal of the Chemical Society, Perkin Transactions, 1(3), 371-376. https://doi.org/10.1039/b109597h
Meng, Q., & Liu, K. (2014). Pharmacokinetic interactions between herbal medicines and prescribed drugs: Focus on drug metabolic enzymes and transporters. Current Drug Metabolism, 15(8), 791-807. https://doi.org/10.2174/1389200216666150223152348
Milutinović, M. G., Maksimović, V. M., Cvetković, D. M., Nikodijević, D. D., Stanković, M. S., Pešić, M., & Marković, S. D. (2019). Potential of Teucrium chamaedrys L. to modulate apoptosis and biotransformation in colorectal carcinoma cells. Journal of Ethnopharmacology, 240, 111951. https://doi.org/10.1016/j.jep.2019.111951
Oliveira-Freitas, V. L., Dalla Costa, T., Manfro, R. C., Cruz, L. B., & Schwartsmann, G. (2010). Influence of purple grape juice in cyclosporine bioavailability. Journal of Renal Nutrition, 20(5), 309-313. https://doi.org/10.1053/j.jrn.2010.01.007
Palatini, P., & De Martin, S. (2016). Pharmacokinetic drug interactions in liver disease: An update. World Journal of Gastroenterology, 22(3), 1260. https://doi.org/10.3748/wjg.v22.i3.1260
Patel, J., & Mitra, A. K. (2001). Strategies to overcome simultaneous P-glycoprotein mediated efflux and CYP3A4 mediated metabolism of drugs. Pharmacogenomics, 2(4), 401-415. https://doi.org/10.1517/14622416.2.4.401
Paudel, S., Kim, Y., Choi, S. M., Kim, J. H., Bae, J. S., Lee, T., & Lee, S. (2021). Identification of suberosin metabolites in human liver microsomes by high-performance liquid chromatography combined with high-resolution quadrupole-orbitrap mass spectrometer. Journal of Mass Spectrometry, 56(4), e4623. https://doi.org/10.1002/jms.4623
Rannug, U., Agurell, E., Rannug, A., & Cederberg, H. (1992). Certain tryptophan photoproducts are inhibitors of cytochrome p450-dependent mtuagenicity. Environmental and Molecular Mutagenesis, 20(4), 289-296. https://doi.org/10.1002/em.2850200407
Rastogi, H., & Jana, S. (2014). Evaluation of inhibitory effects of caffeic acid and quercetin on human liver cytochrome p450 activities. Phytotherapy Research, 28(12), 1873-1878. https://doi.org/10.1002/ptr.5220
Shrestha, R., Kim, J.-H., Nam, W., Lee, H. S., Lee, J.-M., & Lee, S. (2018). Selective inhibition of CYP2C8 by fisetin and its methylated metabolite, geraldol, in human liver microsomes. Drug Metabolism and Pharmacokinetics, 33(2), 111-117. https://doi.org/10.1016/j.dmpk.2017.12.006
Song, M., Hwang, J. Y., Lee, M. Y., Jee, J.-G., Lee, Y. M., Bae, J.-S., Kim, J. A., & Lee, S. (2014). In vitro inhibitory effect of piperlonguminine isolated from Piper longum on human cytochrome P450 1A2. Archives of Pharmacal Research, 37(8), 1063-1068. https://doi.org/10.1007/s12272-013-0281-5
Srivastava, A. K., Kumar, D., Singh, D., & Singh, R. K. (2022). Xenobiotics in chemical carcinogenesis: Translational aspects in toxicology. Academic Press.
Strapazzon, N. C. T. (2011). Time course effect of dietary exposure from cruciferous and apiaceous vegetables on rat hepatic CYP1A1, CYP1A2, and SULT1A1 enzymes.
Tabanca, N., Tsikolia, M., Özek, G., Özek, T., Ali, A., Bernier, U. R., & Khan, I. A. (2016). The identification of suberosin from Prangos pabularia essential oil and its mosquito activity against Aedes aegypti.
Ueng, Y.-F., Jan, W.-C., Lin, L.-C., Chen, T.-L., Guengerich, F. P., & Chen, C.-F. (2002). The alkaloid rutaecarpine is a selective inhibitor of cytochrome P450 1A in mouse and human liver microsomes. Drug Metabolism and Disposition, 30(3), 349-353. https://doi.org/10.1124/dmd.30.3.349
Uno, T., Kaji, S., Goto, T., Imaishi, H., Nakamura, M., Kanamaru, K., Yamagata, H., Kaminishi, Y., & Itakura, T. (2011). Metabolism of the herbicides chlorotoluron, diuron, linuron, simazine, and atrazine by CYP1A9 and CYP1C1 from Japanese eel (Anguilla japonica). Pesticide Biochemistry and Physiology, 101(2), 93-102. https://doi.org/10.1016/j.pestbp.2011.08.005
VandenBrink, B. M., Foti, R. S., Rock, D. A., Wienkers, L. C., & Wahlstrom, J. L. (2011). Evaluation of CYP2C8 inhibition in vitro: Utility of montelukast as a selective CYP2C8 probe substrate. Drug Metabolism and Disposition, 39(9), 1546-1554. https://doi.org/10.1124/dmd.111.039065
Wang, K., Gao, Q., Zhang, T., Rao, J., Ding, L., & Qiu, F. (2020). Inhibition of CYP2C9 by natural products: Insight into the potential risk of herb-drug interactions. Drug Metabolism Reviews, 52(2), 235-257. https://doi.org/10.1080/03602532.2020.1758714
Wilkinson, G. R. (2005). Drug metabolism and variability among patients in drug response. New England Journal of Medicine, 352(21), 2211-2221. https://doi.org/10.1056/NEJMra032424
Xie, Q., Li, S.-X., Liao, D.-F., Wang, W., Tekwani, B., Huang, H.-Y., Ali, A., Rehman, J., Schrader, K. K., Duke, S. O., Cantrell, C. L., & Wedge, D. E. (2016). Bio-pesticidal and antimicrobial coumarins from angelica dahurica (Fisch. Ex Hoffm). Records of Natural Products, 10(3).
Yadav, J., Korzekwa, K., & Nagar, S. (2018). Improved predictions of drug-drug interactions mediated by time-dependent inhibition of CYP3A. Molecular Pharmaceutics, 15(5), 1979-1995. https://doi.org/10.1021/acs.molpharmaceut.8b00129
Yu, A., & Haining, R. L. (2001). Comparative contribution to dextromethorphan metabolism by cytochrome P450 isoforms in vitro: Can dextromethorphan be used as a dual probe for both CYP2D6 and CYP3A activities? Drug Metabolism and Disposition, 29(11), 1514-1520.
Zhao, M., Ma, J., Li, M., Zhang, Y., Jiang, B., Zhao, X., Huai, C., Shen, L., Zhang, N., Qin, S., & He, L. (2021). Cytochrome P450 enzymes and drug metabolism in humans. International Journal of Molecular Sciences, 22(23), 12808. https://doi.org/10.3390/ijms222312808
Zhou, S., Chan, E., Li, S. C., Huang, M., Chen, X., Li, X., Zhang, Q., & Paxton, J. W. (2004). Predicting pharmacokinetic herb-drug interactions. Drug Metabolism and Drug Interactions, 20(3), 143-158. https://doi.org/10.1515/dmdi.2004.20.3.143