Comprehensive assessment of Cucurbitacin E related hepatotoxicity and drug-drug interactions involving CYP3A and P-glycoprotein

Phytomedicine

Volumn 26, Issue , 2017, Pages 1-10

  Lu, Jian ^a   Zhang, Yuanjin ^a   Sun, Min ^a   Liu, Mingyao ^a,b   Wang, Xin ^a  

^a EAST CHINA NORMAL UNIVERSITY   (China)

^b TEXAS A AND M HEALTH SCIENCE CENTER   (United States)

Author keywords

Cucurbitacin E; CYP3A; Drug drug interactions; Hepatotoxicity; P glycoprotein

Indexed keywords

CARBAMAZEPINE; CUCURBITACIN; CUCURBITACIN E; CYTOCHROME P450 3A; DIGOXIN; INDINAVIR; KETOCONAZOLE; MULTIDRUG RESISTANCE PROTEIN; NEUTRAL RED; SULFORHODAMINE B; UNCLASSIFIED DRUG; TRITERPENE;

ANIMAL CELL; ANIMAL EXPERIMENT; APOPTOSIS; ARTICLE; CACO-2 CELL LINE; CELL VIABILITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOPLASM; CYTOTOXICITY ASSAY; DRUG BLOOD LEVEL; DRUG PENETRATION; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC50; IN VITRO STUDY; INTESTINE; LIVER; LIVER CELL CARCINOMA; LIVER MICROSOME; LIVER TOXICITY; MALE; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN INTERACTION; RAT; ANIMAL; DRUG EFFECTS; DRUG INTERACTION; METABOLISM; PATHOPHYSIOLOGY; SPRAGUE DAWLEY RAT; TOXIC HEPATITIS;

ANIMALS; CACO-2 CELLS; CHEMICAL AND DRUG INDUCED LIVER INJURY; CYTOCHROME P-450 CYP3A; DRUG INTERACTIONS; HUMANS; LIVER; MALE; MICROSOMES, LIVER; P-GLYCOPROTEINS; RATS; RATS, SPRAGUE-DAWLEY; TRITERPENES;

EID: 85009775172     PISSN: 09447113     EISSN: 1618095X     Source Type: Journal    
DOI: 10.1016/j.phymed.2017.01.004     Document Type: Article

References (35)

1. Arel-Dubeau, A.M., Longpre, F., Bournival, J., Tremblay, C., Demers-Lamarche, J., Haskova, P., Attard, E., Germain, M., Martinoli, M.G., Cucurbitacin E has neuroprotective properties and autophagic modulating activities on dopaminergic neurons. Oxid. Med. Cell Longev. 2014 (2014), 425496–425510.
2. Attard, E., Brincat, M.P., Cuschieri, A., Immunomodulatory activity of cucurbitacin E isolated from Ecballium elaterium. Fitoterapia 76 (2005), 439–441.
3. Balimane, P.V., Marino, A., Chong, S., P-gp inhibition potential in cell-based models: which “calculation” method is the most accurate?. AAPS J 10 (2008), 577–586.
4. Bartalis, J., Halaweish, F.T., In vitro and QSAR studies of cucurbitacins on HepG2 and HSC-T6 liver cell lines. Bioorg. Med. Chem. 19 (2011), 2757–2766.
5. Chen, A., Qin, X., Tang, Y., Liu, M., Wang, X., Evaluation of enzyme inhibition kinetics in drug-drug interactions. Chem. Biol. Interact. 222 (2014), 133–134.
6. Chen, J.C., Chiu, M.H., Nie, R.L., Cordell, G.A., Qiu, S.X., Cucurbitacins and cucurbitane glycosides: structures and biological activities. Nat. Prod. Rep. 22 (2005), 386–399.
7. China Pharmacopoeia Commission. Pharmacopoeia of the People's Republic of China (Part One). 2015, Chemical Industry Press, Beijing.
8. Ding, T., Zhang, Y., Chen, A., Tang, Y., Liu, M., Wang, X., Effects of cucurbitacin e, a tetracyclic triterpene compound from Cucurbitaceae, on the pharmacokinetics and pharmacodynamics of warfarin in rats. Basic Clin. Pharmacol. Toxicol. 116 (2015), 385–389.
9. Dong, Y., Lu, B., Zhang, X., Zhang, J., Lai, L., Li, D., Wu, Y., Song, Y., Luo, J., Pang, X., Yi, Z., Liu, M., Cucurbitacin E, a tetracyclic triterpenes compound from Chinese medicine, inhibits tumor angiogenesis through VEGFR2-mediated Jak2-STAT3 signaling pathway. Carcinogenesis 31 (2010), 2097–2104.
10. Eichhorn, T., Efferth, T., P-glycoprotein and its inhibition in tumors by phytochemicals derived from Chinese herbs. J. Ethnopharmacol. 141 (2012), 557–570.
11. Guengerich, F.P., Cytochrome p450 and chemical toxicology. Chem. Res. Toxicol. 21 (2008), 70–83.
12. Jennen, D.G., Magkoufopoulou, C., Ketelslegers, H.B., van Herwijnen, M.H., Kleinjans, J.C., van Delft, J.H., Comparison of HepG2 and HepaRG by whole-genome gene expression analysis for the purpose of chemical hazard identification. Toxicol. Sci. 115 (2010), 66–79.
13. Kim, E.A., Jang, J.H., Lee, Y.H., Sung, E.G., Song, I.H., Kim, J.Y., Kim, S., Sohn, H.Y., Lee, T.J., Dioscin induces caspase-independent apoptosis through activation of apoptosis-inducing factor in breast cancer cells. Apoptosis 19 (2014), 1165–1175.
14. Li, Y.H., Kan, W.L., Li, N., Lin, G., Assessment of pyrrolizidine alkaloid-induced toxicity in an in vitro screening model. J. Ethnopharmacol. 150 (2013), 560–567.
15. Lu, J., Ding, T.G., Qin, X., Liu, M.Y., Wang, X., In vitro and in vivo evaluation of cucurbitacin E on rat hepatic CYP2C11 expression and activity using LC-MS/MS. Sci. China Life. Sci., 2015, 1–10.
16. Matuo, M.C.S., de Oliveira Takamoto, R.T., Kikuchi, I.S., de Jesus Andreoli Pinto, T., Effect of bixin and norbixin on the expression of cytochrome P450 in HepG2 cell line. Cell Biol. Int. 37 (2013), 843–848.
17. Qiao, J., Xu, L.H., He, J., Ouyang, D.Y., He, X.H., Cucurbitacin E exhibits anti-inflammatory effect in RAW 264.7 cells via suppression of NF-kappaB nuclear translocation. Inflamm. Res. 62 (2013), 461–469.
18. Qin, X.L., Chen, X., Zhong, G.P., Fan, X.M., Wang, Y., Xue, X.P., Wang, Y., Huang, M., Bi, H.C., Effect of tacrolimus on the pharmacokinetics of bioactive lignans of Wuzhi tablet (Schisandra sphenanthera extract) and the potential roles of CYP3A and P-gp. Phytomedicine 21 (2014), 766–772.
19. Rahimi, R., Abdollahi, M., An update on the ability of St. John's wort to affect the metabolism of other drugs. Expert Opin. Drug Metab. Toxicol. 8 (2012), 691–708.
20. Sun, C., Zhang, M., Shan, X., Zhou, X., Yang, J., Wang, Y., Li-Ling, J., Deng, Y., Inhibitory effect of cucurbitacin E on pancreatic cancer cells growth via STAT3 signaling. J. Cancer Res. Clin. Oncol. 136 (2010), 603–610.
21. Sun, M., Tang, Y., Ding, T., Liu, M., Wang, X., Investigation of cytochrome P450 inhibitory properties of maslinic acid, a bioactive compound from Olea europaea L., and its structure-activity relationship. Phytomedicine 22 (2015), 56–65.
22. Ueng, Y.-F., Chen, C.-C., Yamazaki, H., Kiyotani, K., Chang, Y.-P., Lo, W.-S., Li, D.-T., Tsai, P.-L., Mechanism-based Inhibition of CYP1A1 and CYP3A4 by the furanocoumarin chalepensin. Drug Metab. Pharmacokinet 28 (2013), 229–238.
23. van Waterschoot, R.A., Lagas, J.S., Wagenaar, E., van der Kruijssen, C.M., van Herwaarden, A.E., Song, J.Y., Rooswinkel, R.W., van Tellingen, O., Rosing, H., Beijnen, J.H., Schinkel, A.H., Absence of both cytochrome P450 3A and P-glycoprotein dramatically increases docetaxel oral bioavailability and risk of intestinal toxicity. Cancer Res. 69 (2009), 8996–9002.
24. van Waterschoot, R.A., Schinkel, A.H., A critical analysis of the interplay between cytochrome P450 3A and P-glycoprotein: recent insights from knockout and transgenic mice. Pharmacol. Rev. 63 (2011), 390–410.
25. Wang, X., Cheung, C.M., Lee, W.Y., Or, P.M., Yeung, J.H., Major tanshinones of Danshen (Salvia miltiorrhiza) exhibit different modes of inhibition on human CYP1A2, CYP2C9, CYP2E1 and CYP3A4 activities in vitro. Phytomedicine 17 (2010), 868–875.
26. Wang, Z., Lin, Y.S., Dickmann, L.J., Poulton, E.J., Eaton, D.L., Lampe, J.W., Shen, D.D., Davis, C.L., Shuhart, M.C., Thummel, K.E., Enhancement of hepatic 4-hydroxylation of 25-hydroxyvitamin D3 through CYP3A4 induction in vitro and in vivo: implications for drug-induced osteomalacia. J. Bone Miner. Res. 28 (2013), 1101–1116.
27. Wen, T., Liu, Y.C., Yang, H.W., Liu, H.Y., Liu, X.D., Wang, G.J., Xie, L., Effect of 21-day exposure of phenobarbital, carbamazepine and phenytoin on P-glycoprotein expression and activity in the rat brain. J. Neurol. Sci. 270 (2008), 99–106.
28. Yang, J.M., Ip, S.P., Xian, Y., Zhao, M., Lin, Z.X., Yeung, J.H., Chan, R.C., Lee, S.S., Che, C.T., Impact of the herbal medicine Sophora flavescens on the oral pharmacokinetics of indinavir in rats: the involvement of CYP3A and P-glycoprotein. PLoS One, 7, 2012, e31312.
29. Yu, J., Xie, J., Mao, X.J., Wang, M.J., Li, N., Wang, J., Zhaori, G.T., Zhao, R.H., Hepatoxicity of major constituents and extractions of radix polygoni multiflori and radix polygoni multiflori praeparata. J. Ethnopharmacol. 137 (2011), 1291–1299.
30. Zhang, T., Li, J., Dong, Y., Zhai, D., Lai, L., Dai, F., Deng, H., Chen, Y., Liu, M., Yi, Z., Cucurbitacin E inhibits breast tumor metastasis by suppressing cell migration and invasion. Breast Cancer Res. Treat 135 (2012), 445–458.
31. Zhang, Y., Zeng, Z., Zhao, J., Li, D., Liu, M., Wang, X., Measurement of rhodamine 123 in three-dimensional organoids: a novel model for p-glycoprotein inhibitor screening. Basic Clin. Pharmacol. Toxicol. 119 (2016), 349–352.
32. Zhao, J., Zeng, Z., Sun, J., Zhang, Y., Li, D., Zhang, X., Liu, M., Wang, X., A novel model of p-glycoprotein inhibitor screening using human small intestinal organoids. Basic Clin. Pharmacol. Toxicol., 2016, 10.1111/bcpt.12680.
33. Zhou, S.F., Structure, function and regulation of P-glycoprotein and its clinical relevance in drug disposition. Xenobiotica 38 (2008), 802–832.
34. Zhou, Y., He, P., Liu, A., Zhang, L., Liu, Y., Dai, R., Drug-drug interactions between ketoconazole and berberine in rats: pharmacokinetic effects benefit pharmacodynamic synergism. Phytother. Res. 26 (2012), 772–777.
35. Zhuang, X.M., Shen, G.L., Xiao, W.B., Tan, Y., Lu, C., Li, H., Assessment of the roles of P-glycoprotein and cytochrome P450 in triptolide-induced liver toxicity in sandwich-cultured rat hepatocyte model. Drug Metab. Dispos. 41 (2013), 2158–2165.