Induction of xenobiotic metabolising enzymes in the common brushtail possum, Trichosurus vulpecula, by Eucalyptus terpenes

Comparative Biochemistry and Physiology - C Pharmacology Toxicology and Endocrinology

Volumn 124, Issue 3, 1999, Pages 239-246

  Pass, Georgia J ^a   McLean, Stuart ^a   Stupans, Ieva ^b  

^a UNIVERSITY OF TASMANIA   (Australia)

^b UNIVERSITY OF SOUTH AUSTRALIA   (Australia)

Author keywords

Common brushtail possum; Cytochrome P450; Eucalyptus; Induction; Terpenes

Indexed keywords

4 CYMENE; AMINOPYRINE N DEMETHYLASE; CINEOLE; CYTOCHROME P450; CYTOCHROME P450 ISOENZYME; LIMONENE; MIXED FUNCTION OXIDASE; OXYGENASE; PINENE; TERPENE DERIVATIVE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DIET SUPPLEMENTATION; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME INDUCTION; EUCALYPTUS; MALE; NONHUMAN; OPOSSUM; ORAL DRUG ADMINISTRATION; PRIORITY JOURNAL; TREATMENT OUTCOME; XENOBIOTIC METABOLISM;

ANIMALS; ARYL HYDROCARBON HYDROXYLASES; CYTOCHROME P-450 ENZYME SYSTEM; DIET; ENZYME INDUCTION; EUCALYPTUS; HUMANS; MIXED FUNCTION OXYGENASES; OPOSSUMS; PLANTS, MEDICINAL; RATS; STEROID 16-ALPHA-HYDROXYLASE; STEROID 21-HYDROXYLASE; TERPENES; XENOBIOTICS;

EID: 0032735534     PISSN: 07428413     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0742-8413(99)00085-7     Document Type: Article

References (43)

1. Amato G., Longo V., Mazzaccaro A., Giovanni Gervasi P. Chlorzoxazone 6-hydroxylase and p-nitrophenol hydroxylase as the most suitable activities for assaying cytochrome P450 2E1 in cynomolgus monkey liver. Drug Metab. Dispos. 26:1998;483-489.
2. Boland D.J., Brophy J.J. Eucalyptus leaf oils. Use, chemistry, distillation and marketing. 1st ed:1991;Melbourne, Inkata.
3. Bolton R.M., Ahokas J.T. Mixed function oxidases in an Australian marsupial, the Brushtail possum (Trichosurus vulpecula). Arch. Environ. Contam. Toxicol. 33:1997;83-89.
4. Boobis A.R., McKillop D., Robinson D.T., Adams D.A., McCormick D.J. Interlaboratory comparison of the assessment of P450 activities in human hepatic microsomal samples. Xenobiotica. 28:1998;493-506.
5. Bull S.D., Carman R.M., Carrick F.N., Klika K.D. 7-Hydroxy-1,8-cineole and 7-cineolic acid. Two new possum urinary metabolites. Aust. J. Chem. 46:1993;441-447.
6. Cantrill E., Murray M., Mehta I., Farrell G.C. Downregulation of the male-specific hepatic microsomal steroid 16 alpha-hydroxylase, cytochrome P-450UT-A, in rats with portal bypass. Relevance to estradiol accumulation and impaired drug metabolism in hepatic cirrhosis. J. Clin. Invest. 83:1989;1211-1216.
7. Carman R.M., Garner A.C. 7,9-Dihydroxy-1,8-cineole and 2α,7-dihydroxy-1,8-cineole: two new possum urinary metabolites. Aust. J. Chem. 49:1996;741-749.
8. Carman R.M., Klika K.D. Partially racemic compounds as brushtail possum urinary metabolites. Aust. J. Chem. 45:1992;651-657.
9. De-Oliveira A.C.A.X., Ribeiro-Pinto L.F., Otto S.S., Goncalves A., Paumgartten F.J.R. Induction of liver monoxygenases by β-myrcene. Toxicology. 124:1997;135-140.
10. Flynn T.M., Southwell I.A. 1,3-Dimethyl-2-oxabicyclo[2,2,2]-octane-3-methanol and 1,3-dimethyl-2-oxa-bicyclo[2,2,2]octane-3-carboxylic acid, urinary metabolites of 1,8-cineole. Aust. J. Chem. 32:1979;2093-2095.
11. Foley W.J., Lassak E.V., Brophy J. Digestion and absorption of Eucalyptus essential oils in greater glider (Petauroides volans) and the brushtail possum (Trichosurus vulpecula). J. Chem. Ecol. 13:1987;2115-2130.
12. Foley W.J., McLean S., Cork S.J. Consequences of biotransformation of plant secondary metabolites on acid-base metabolism in mammals - a final common pathway? J. Chem. Ecol. 21:1995;721-743.
13. Freeland W.J., Janzen H. Strategies in herbivory by mammals: the role of plant secondary compounds. Am. Nat. 108:1974;269-287.
14. Guengerich F.P. Comparisons of catalytic selectivity of cytochrome P450 subfamily enzymes from different species. Chem.-Biol. Interact. 106:1997;161-182.
15. Gustafsson J.A., Ingelman-Sunberg M. Regulation and substrate specificity of a steroid sulfate-specific hydroxylase system in female rat liver microsomes. J. Biol. Chem. 250:1975;3451-3458.
16. Hiroi T., Miyazaki Y., Kobayashi Y., Imaoka S., Funae Y. Induction of hepatic P450s in rat by essential wood and leaf oils. Xenobiotica. 25:1995;457-467.
17. Ho P.-C., Luo X.-X., Macauley J.S., Murray R.G., Wanwimolruk S. In vitro hepatic metabolism of CYP3A-mediated drugs quinine and midazolam in the common brushtail possum (Trichosurus vulpecula). Environ. Toxicol. Chem. 17:1998;317-324.
18. Ishida T., Asakawa Y., Takemoto T., Aratani T. Terpenoid biotransformation in mammals. III: Biotransformation of α-pinene, β-pinene, pinane, 3-carene, carane, myrcene, and p-cymene in rabbits. J. Pharm. Sci. 70:1981;406-415.
19. Ko I.-Y., Park S.S., Song B.J., Patten C., Tan Y., Hah Y.C. et al. Monoclonal antibodies to ethanol-induced rat liver cytochrome P-450 that metabolises aniline and nitrosamines. Cancer Res. 47:1987;3101-3109.
20. Kodama R., Yano T., Furukawa K., Noda K., Ide H. Studies on the metabolism of D-limonene (p-mentha-1,8-diene). IV isolation and characterization of new metabolites and species differences in metabolism. Xenobiotica. 6:1976;377-389.
21. Koop D. Hydroxylation of p-nitrophenol by rabbit ethanol-inducible cytochrome P450 isozyme 3a. Mol. Pharm. 29:1986;399-404.
22. Laemmli U.K. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature. 227:1970;680-685.
23. Lewis D.F.V. The CYP2 family: models, mutants and interactions. Xenobiotica. 28:1998;617-661.
24. Lowry O.H., Rosenbrough N.J., Farr A.L., Randall R.J. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193:1951;265-275.
25. Madhava Madyastha K., Srivatsan V. Metabolism of β-myrcene in vivo and in vitro: its effects on rat-liver microsomal enzymes. Xenobiotica. 17:1987;539-549.
26. McClure M.T., Stupans I. Investigation of the mechanism by which cyclophosphamide alters cytochrome P450 in male rats. Biochem. Pharmacol. 43:1992;2655-2658.
27. McLean S., Foley W.J., Davies N.W., Brandon S., Duo L., Blackman A.J. Metabolic fate of dietary terpenes from Eucalyptus radiata in common ringtail possums (Pseudocheirus peregrinus). J. Chem. Ecol. 19:1993;1625-1643.
28. McManus M.E., Ilett K.F. Mixed function oxidase activity in a marsupial, the quokka (Setonix brachyurus). Drug Metab. Dispos. 4:1976;199-202.
29. McManus M.E., Ilett K.F. Microsomal xenobiotic metabolism in marsupials. Drug Metab. Dispos. 5:1977;503-510.
30. McManus M.E., McGeachie J.K., Ilett K.F. Development of the hepatic mixed function oxidase system in a marsupial, the quokka (Setonix brachyurus). Toxicol. Appl. Pharmacol. 46:1978;117-124.
31. Miyazawa M., Wada T., Kameoka H. Biotransformation of (+)- and ((-)-limonene by the larvae of common cutworm (Spodoptera litura). J. Agric. Food Chem. 46:1998;300-303.
32. Nash T. The colorimetric estimation of formaldehyde by means of the Hontzsch reaction. Biochem. J. 55:1953;416-421.
33. Olkowski A., Gooneratne R., Eason C. Cytochrome P450 enzyme activities in the Australian brushtail possum, Trichosurus vulpecula: a comparison with the rat, rabbit, sheep and chicken. Vet. Hum. Toxicol. 40:1998;70-76.
34. Rendic S., Di Carlo F.J. Human cytochrome P450 enzymes: a status report summarizing their reactions, substrates, inducers, and inhibitors. Drug Metab. Rev. 29:1997;413-580.
35. Song B.-J., Veech R.L., Park S.S., Gelboin H.V., Gonzalez F.J. Induction of rat hepatic N-nitrosodimethylamine demethylase by acetone is due to protein stabilisation. J. Biol. Chem. 264:1989;3568-3572.
36. Southwell I.A., Flynn T.M., Degabriele R. Metabolism of α- and β-pinene, p-cymene and 1,8-cineole in the brushtail possum, Trichosurus vulpecula. Xenobiotica. 10:1980;17-23.
37. Stupans I., Sansom L.N. The inhibition of drug oxidation by anhydroerythromycin, an acid degradation product of erythromycin. Biochem. Pharmacol. 42:1991;2085-2090.
38. Stupans I, Kong S, Kirlich A, Murray M, Bailey EL, Jones BR, McKinnon RA. Hepatic microsomal enzyme activity in the koala and tammar wallaby: high 17β-hydroxysteroid oxidoreductase activity in koala liver microsomes, Comp Biochem Physiol 1999;123(C):67-73.
39. Stupans I., Richards D.A., McClure M.T. Effects of 5-fluorouracil treatment on rat liver microsomal enzymes. Xenobiotica. 25:1995;1-8.
40. Tassaneeyakul W., Veronese M.E., Birkett D.J., Gonzalez F.J., Miners J.O. Validation of 4-nitrophenol as an in vitro substrate probe for human liver CYP2E1 using cDNA expression and microsomal kinetic techniques. Biochem. Pharmacol. 46:1993;1975-1981.
41. Walde A., Ve B., Scheline R.R., Monge P. p-Cymene metabolism in rats and guinea-pigs. Xenobiotica. 13:1983;503-512.
42. Waxman D.J., Dannan G.A., Guengerich F.P. Regulation of rat hepatic cytochrome P450: age dependent expression, hormonal imprinting, and xenobiotic inducibility of sex-specific isoenzymes. Biochemistry. 24:1985;4409-4417.
43. Woodcroft K.J., Novak R.F. Xenobiotic-enhanced expression of cytochromes P450 2E1 and 2B in primary cultured rat hepatocytes. Drug Metab. Dispos. 26:1998;372-378.