Identification of quinone methide metabolites of dauricine in human liver microsomes and in rat bile

Chemical Research in Toxicology

Volumn 22, Issue 5, 2009, Pages 824-834

  Wang, Yuya ^a   Zhong, Dafang ^a   Chen, Xiaoyan ^a   Zheng, Jiang ^b  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^b UNIVERSITY OF WASHINGTON SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450; DAURICINE; GLUTATHIONE; KETOCONAZOLE; PHENOL; QUINONE DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE;

ARTICLE; BILE; CATALYSIS; CHEMICAL STRUCTURE; CONJUGATION; CONTROLLED STUDY; HUMAN; HUMAN CELL; ION TRAP MASS SPECTROMETRY; LIQUID CHROMATOGRAPHY; LIVER MICROSOME; NONHUMAN; RAT; SYNTHESIS;

ADMINISTRATION, ORAL; ANIMALS; BENZYLISOQUINOLINES; BILE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME P-450 CYP3A; GLUTATHIONE; HUMANS; INDOLEQUINONES; KETOCONAZOLE; MICROSOMES, LIVER; RATS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TETRAHYDROISOQUINOLINES;

ANIMALIA; RATTUS;

EID: 67650002130     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx800397e     Document Type: Article

References (28)

1. Angerhofer, C. K., Guinaudeau, H., Wongpanich, V., Pezzuto, J. M., and Cordell, G. A. (1999) Antiplasmodial and cytotoxic activity of natural bisbenzylisoquinoline alkaloids. J. Nat. Prod. 62, 59-66.
2. Marshall, S. J., Russell, P. F., Wright, C. W., Anderson, M. M., Phillipson, J. D., Kirby, G. C., Warhurst, D. C., and Schiff, P. L., Jr. (1994) In vitro antiplasmodial, antiamoebic, and cytotoxic activities of a series of bisbenzylisoquinoline alkaloids. Antimicrob. Agents Chemother. 38, 96-103.
3. He, Q. Y., Meng, F. H., and Zhang, H. Q. (1996) Reduction of doxorubicin resistance by tetrandrine and dauricine in harringtonine-resistant human leukemia (HL60) cells. Acta Pharmacol. Sin. 17, 179-181.
4. Lohombo-Ekomba, M. L., Okusa, P. N., Penge, O., Kabongo, C., Choudhary, M. I., and Kasende, O. E. (2004) Antibacterial, antifungal, antiplasmodial, and cytotoxic activities of Albertisia Villosa. J. Ethnopharmacol. 93, 331-335.
5. Zhao, X., Cui, X. Y., Chen, B. Q., Chu, Q. P., Yao, H. Y., Ku, B. S., and Zhang, Y. H. (2004) Tetrandrine, a bisbenzylisoquinoline alkaloid from Chinese herb Radix, augmented the hypnotic effect of pentobarbital through serotonergic system. Eur. J. Pharmacol. 506, 101-105.
6. Li, Y. H., and Gong, P. L. (2007) Neuroprotective effect of dauricine in cortical neuron culture exposed to hypoxia and hypoglycemia: involvement of correcting perturbed calcium homeostasis. Can. J. Physiol. Pharmacol. 85, 621-627.
7. Li, Y. H., and Gong, P. L. (2007) Neuroprotective effects of dauricine against apoptosis induced by transient focal cerebral ischaemia in rats via a mitochondrial pathway. Clin. Exp. Pharmacol. Physiol. 34, 177-184.
8. Lin, H., Wang, Y., Xiong, Z., Tang, Y., and Liu, W. (2007) Effect of antenatal tetrandrine administration on endothelin-1 and epidermal growth factor levels in the lungs of rats with experimental diaphragmatic hernia. J. Pediatr. Surg. 42, 1644-1651.
9. Yang, X. Y., Jiang, S. Q., Zhang, L., Liu, Q. N., and Gong, P. L. (2007) Inhibitory effect of dauricine on inflammatory process following focal cerebral ischemia/reperfusion in rats. Am. J. Chin. Med. 35, 477-486.
10. Du, Z. H., Liu, H. G., Chai, C. Y., Luo, L. Y., and Hu, C. J. (1986) Anti-inflammatory effect of dauricine. Zhongguo Yao Li Xue Bao 7, 419-422.
11. Qian, J. Q. (2002) Cardiovascular pharmacological effects of bisbenzylisoquinoline alkaloid derivatives. Acta Pharmacol. Sin. 23, 1086-1092.
12. Xia, J. S., Guo, D. L., Zhang, Y., Zhou, Z. N., Zeng, F. D., and Hu, C. J. (2000) Inhibitory effects of dauricine on potassium currents in guinea pig ventricular myocytes. Acta Pharmacol. Sin. 21, 60-64.
13. Xia, J. S., Li, Z., Dong, J. W., Tu, H., and Zeng, F. D. (2002) Dauricine-induced changes in monophasic action potentials and effective refractory period of rabbit left ventricle in situ. Acta Pharmacol. Sin. 23, 371-375.
14. Chen, S., Liu, L., Yang, Y., Dai, Z., and Zeng, F. (2000) Metabolism of dauricine and identification of its main metabolites. J. Tongji. Med. Univ. 20, 253-256.
15. Han, F. M., Peng, Z. H., Song, W., Zhang, H. M., Zhu, M. M., and Chen, Y. (2007) Identification of dauricine and its metabolites in rat urine by liquid chromatography-tandem mass spectrometry. J.Chromatogr., B 854, 1-7.
16. Becker, H. D., and Gustafsson, K. (1976) Preparation and reactions of 2,6-di-tert-butyl-4-(9-fluorenylidene)-1,4-benzoquinone. J. Org. Chem. 41, 214-221.
17. U.S. Department of Health and Human Service, Food and Drug Administration. (2006) Guidance for Industry on Drug Interaction Studies. http://www.fda.gov/cder/guidelines.htm (accessed September 2006).
18. Ma, S. G. and Chowdhury, S. K. (2007) Application of liquid chromatography/mass spectrometry for metabolite identification. In Drug Metabolism in Drug Design and Development (Zhang, D. L., Zhu, M. S., and Humphreys, W. G., Eds.) pp 354-357.
19. Yao, M., Ma, L., Humphreys, W. G., and Zhu, M. (2008) Rapid screening and characterization of drug metabolites using a multiple ion monitoring-dependent MS/MS acquisition method on a hybrid triple quadrupole-linear ion trap mass spectrometer. J. Mass. Spectrom. 80, 1788-1799.
20. Gan, J., Hsueh, M. M., Qu, Q., Harper, T. W., and Humphreys, W. G. (2005) Dansyl glutathione as a trapping agent for the quantitative estimation and identification of reactive metabolites. Chem. Res. Toxicol. 18, 896-903.
21. Korfmacher, W. (2005) Using Mass Spectrometry for Drug Metabolism Studies, Chapter 8, CRC Press, Boca Raton, FL.
22. Bolton, J. L., Trush, M. A., Penning, T. M., Dryhurst, G., and Monks, T. J. (2000) Role of quinones in toxicology. Chem. Res. Toxicol. 13, 135-160.
23. Monks, T. J., and Jones, D. C. (2002) The metabolism and toxicity of quinones, quinonimines, quinone methides and quinone-thioethers. Curr. Drug. Metab. 3, 425-438.
24. Baillie, T. A. (2008) Metabolism and toxicity of drugs. Two decades of progress in industrial drug metabolism. Chem. Res. Toxicol. 21, 129-137.
25. Reilly, C. A., and Yost, G. S. (2006) Metabolism of capsaicinoids by P450 enzymes: a review of recent findings on reaction mechanisms, bio-activation, and detoxification processes. Drug Metab. Rev. 38, 685-706.
26. Bender, R. P., Lindsey, R. H. J., Burden, D. A., and Osheroff, N. (2004) N-Aceyl-p-benzoquinone imine, the toxic metabolite of acetaminophen, is a topoisomerase II poison. Biochemistry 43, 3731-3739.
27. Lindsey, R. H. J., Bender, R. P., and Osheroff, N. (2005) Effect of benzene metabolites on DNA cleavage mediated by human topoisomerase IIR: 1, 4-hydroquinone is a topoisomerase II poison. Chem. Res. Toxicol. 18, 761-770.
28. Thompson, D. C., Perera, K., Krol, E. S., and Bolton, J. L. (1995) o-Methoxy-4-alkylphenols that form quinone methides of intermediate reactivity are the most toxic in rat liver slices. Chem. Res. Toxicol. 8, 323-327.