The effect of spironolactone treatment on the cytochrome p450-mediated metabolism of the pyrrolizidine alkaloid senecionine by hepatic microsomes from rats and guinea pigs

Toxicology and Applied Pharmacology

Volumn 127, Issue 2, 1994, Pages 314-319

  Chung, Woon Gye ^a   Buhler, Donald R ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0028142608     PISSN: 0041008X     EISSN: None     Source Type: Journal    
DOI: 10.1006/taap.1994.1167     Document Type: Article

References (24)

1. Chesncy, C., and Alien, J. R. (1973). Resistance of the guinea pig to pyrrolizidine alkaloid intoxication. Toxicol. Appl. Pharmacol. 26, 385-392.
2. Decker, C., Sugiyama, K., Underwood, M., and Correia, M. A. (1986). Inactivation of rat hepatic cytochrome P450 by spironolactone. Bio-chem. Biophys. Res. Commun. 136, 1162-1169.
3. Delaforge, M., Jaouen, M., and Mansuy, D. (1983). Dual effects of macro-lide antibiotics on rat liver cytochrome P450: A structure-activity relationship. Biochem. Pharmacol. 32, 2309-2318.
4. Fujita, S., Uesugi, T., Ohta, M., and Kitani, K. (1982). Effect of spironolactone on hepatic microsomal monooxygenase and azoreductase activities. Res Commun. Chem. Pathol. Pharmacol. 36, 87-103.
5. Heuman, D. M., Gallagher, E. J., Barwick, J. L., Elshourbagy, N. A., and Guzelian, P. S. (1982). Immunochemical evidence for induction of a common form of hepatic cytochrome P450 in rats treated with pregnenolone- 16«-carbonitrile or other steroidal or non-steroidal agents. Mol Pharmacol. 21, 753-760.
6. Kedzierski, B., and Buhler, D. R. (1986). Method for determination of pyrrolizidine alkaloids and their metabolites by high-performance liquid chromatography. Anal. Biochem. 152, 59-65.
7. Lowry, O. H., Rosebrough, N. J., Farr, A. I., and Randall, R. J. (1951). Protein measurement with the folin phenol reagent. J. Biol Chem. 193, 265-275.
8. Mattocks, A. R. (1971). Hepatotoxic effects due to pyrrolizidine alkaloid N-oxides. Xenohiolica 1, 563-565.
9. Mattocks, A. R. (1986). Chemistry and Toxicology of Pyrrolizidine Alkaloids. Academic Press. New York.
10. Mattocks, A. R., and White, I. N. H. (1971). The conversion of pyrrolizidine alkaloids to N-oxides and to dihydropyrrolizine derivatives by rat-liver microsomes in vitro. Chem. Biol. Interact. 3, 383-396.
11. McLean, F. K. (1970). The toxic actions of pyrrolizidine (Senecio) alkaloids. Pharmacol. Rev 22, 429-483.
12. Menard, R. H., Guenthener, T. M., Kon, H., and Gillette, J. R. (1979). Studies on the destruction of adrenal and testicular cytochrome P450 by spironolactone: Requirement for the 7α-thio group and evidence for the loss of the heme and apoproteins of cytochrome P-450. J. Biol Chem. 254, 1726-1733.
13. Miranda, C. L., Chung, W. G., Reed, R. L., Zhao, X., Henderson, M. C, Wang, J. L., Williams, D. E., and Buhler, D. R. (1991 a). Flavin-containing monooxygenase: A major detoxifying enzyme for the pyrrolizidine alkaloid senecionine in guinea pig tissues. Biochem. Biophys. Res. Commun. 178, 546-552.
14. Miranda, C. L., Reed, R. L., Guengcrich, F. P., and Buhler, D. R. (1991 b). Role of cytochrome P450 IIIA4 in the metabolism of the pyrrolizidine alkaloid senecionine in human liver. Carcinogenesis 12, 515-519.
15. Miranda, C. L., Reed, R. L., and Buhler, D. R. (1992). Characterization of P450 enzymes involved in senecionine bioactivation in guinea pig liver microsomes. Toxicologist 12, 243.
16. Omura, T., and Sato, R. (1964). The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J. Biol. Chem. 239, 2370-2378.
17. Sherry, J. H., O’Donnell, J. P., Flowers, L., Lacagnin, L. B., and Colby, H. D. (1986). Metabolism of spironolactone by adrenocortical and hepatic microsomes: Relationship to cytochrome P450 destruction. J. Pharmacol. Exp. Titer. 236, 675-680.
18. Waxman, D. J. (1988). Interactions of hepatic cytochrome P450 with steroid hormones: Regioselectivity and stereospecificity of steroid metabolism and hormonal regulation of rat P-450 enzyme expression. Biochem. Pharmacol. 37, 71-84.
19. White, I. N. H., Mattocks, A. R., and Butler, W. H. (1973). The conversion of the pyrrolizidine alkaloid retrorsine to pyrrolic derivatives in vivo and in vitro and its acute toxicity to various animal species. Chem. Biol. Interact. 6, 207-218.
20. Williams, D. E., Reed, R. L., Kedzierski, B., Dannan, G. A., Guengerich, F. P., and Buhler, D. R. (1989a). Bioactivation and detoxication of the pyrrolizidine alkaloid senecionine by cytochrome P-450 enzymes in rat liver. DrugMelab. Dispos. 17, 387-392.
21. Williams, D. E., Reed, R. L., Kedzierski, B., Ziegler, D. M., and Buhler, D. R. (1989b). The role of flavin-containing monooxygenase in the N-oxidation of the pyrrolizidine alkaloid senecionine. Drug Melab. Dispos. 17, 380-386.
22. Wood, A. W., Ryan, D. E., Thomas, P. E., and Levin, W. (1983). Regio-and stereoselective metabolism of two C, steroids by five highly purified and reconstituted rat hepatic cytochrome P-450 isozymes. J Biol. Chem. 258, 8839-8847.
23. Wrighton, S. A., Maurel, P., Schuetz, E. G., Watkins, P. B., Young, B., and Guzelian, P. S. (1985). Identification of the cytochrome P-450 induced by macrolide antibiotics in rat liver as the glucocorticoid responsive cytochrome P450p. Biochemistry 24, 2171-2178.
24. Yeowell, H. N., Waxman, D. J., Wadhera, A., and Goldstein, J. A. (1987). Suppression of the constitutive male-specific rat hepatic P450 2C and its mRNA by 3, 4, 5, 3’, 4’, 5’-hexachlorobiphenyl and 3-methylcholanthrene. Mol. Pharmacol. 32, 340-347.