Oxidation of xenobiotics by plant microsomes, a reconstituted cytochrome P450 system and peroxidase: A comparative study

Phytochemistry

Volumn 54, Issue 4, 2000, Pages 353-362

  Stiborova M ^a   Schmeiser, H H ^b   Frei, E ^b  

^a CHARLES UNIVERSITY   (Czech Republic)

^b GERMAN CANCER RESEARCH CENTER DKFZ   (Germany)

Author keywords

Cytochrome P450; Peroxidase; Tulipa fosteria; Xenobiotics

Indexed keywords

AMINOPHENAZONE; CYTOCHROME P450; DIMETHYLNITROSAMINE; HYDROGEN PEROXIDE; ISOENZYME; N METHYL N NITROSOANILINE; PEROXIDASE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SUDAN I; XENOBIOTIC AGENT;

ARTICLE; COMPARATIVE STUDY; ENZYME ISOLATION; ENZYME KINETICS; ENZYME METABOLISM; ENZYME SUBSTRATE; MICROSOME; NONHUMAN; OXIDATION; OXIDATION REDUCTION REACTION; PLANT; RESPIRATORY CHAIN;

CYTOCHROME P-450 ENZYME SYSTEM; MICROSOMES; OXIDATION-REDUCTION; PEROXIDASES; PLANTS; XENOBIOTICS;

TULIPA; TULIPA FOSTERIANA;

EID: 0034733608     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(00)00123-0     Document Type: Article

References (53)

1. Batard Y., LeRet M., Schalk M., Robineau T., Durst F., Werck-Reichhart D. Molecular cloning and functional expression in yeast of CYP76B1, a xenobiotic-inducible 7-ethoxycoumarin O-de-ethylase from Helianthus tuberosus. Plant J. 14:1998;111-120.
2. Bolwell G.P., Bozak K.R., Zimmerlin A. Plant cytochrome P450. Phytochemistry. 37:1994;1491-1506.
3. Bozak K.R., O'Keefe D.P., Christoffersen R.E. Expression of a ripening-related avocado (Persea americana) cytochrome P450 in yeast. Plant Physiol. 100:1992;1976-1981.
4. Bradford M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72:1976;248-254.
5. Chapple C. Molecular-genetic analysis of plant cytochrome P450-dependent monooxygenases. Annu. Rev. Plant Physiol. Plant Mol. Biol. 49:1998;311-343.
6. Chiapella C., Ysern P., Riera J., Llagostera M. A plant metabolic activation system from Persea americana with cytochrome P450-dependent and peroxidase activities. Mutat. Res. 329:1995;11-18.
7. Cleland W.W. Statistical analysis of enzyme kinetic data. Methods Enzymol. 63:1983;103-138.
8. Dohn D.R., Krieger R.I. Oxidative metabolism of foreign compounds by higher plants. Drug Metab. Rev. 12:1981;119-158.
9. Durst F., Benveniste I. Cytochrome P450 in plants. Handbook Exp. Pharmacol. 105:1993;293-310.
10. Durst F., Benveniste I., Schalk M., Werck-Reichhart D. Cinnamic acid hydroxylase activity in plant microsomes. Methods Enzymol. 272:1996;259-268.
11. Durst F., O'Keefe D.P. Plant cytochromes P450: an overview. Drug Metabol. Drug Interact. 12:1995;171-187.
12. Fonné-Pfister R., Simon A., Salaun J.-P., Durst F. Xenobiotic metabolism in higher plants. Involvement of microsomal cytochrome P450 in aminopyrine N-demethylation. Plant Sci. 55:1988;9-20.
13. Frear D.S. Wheat microsomal cytochrome P450 monooxygenases: characterization and importance in the metabolic detoxication and selectivity of wheat herbicides. Drug Metabol. Drug Interact. 12:1995;329-357.
14. Frear D.S., Swanson H.R., Tanaka F.S. Metabolism of flumetasulam (De 498) in wheat, corn, and barley. Pestic. Biochem. Physiol. 45:1993;178-192.
15. Frear D.S., Swanson H.R., Thalacker F.W. Induced microsomal oxidation of diclofop, triasulfuron, chlorsulfuron, and linuron in wheat. Pestic. Biochem. Physiol. 41:1991;274-287.
16. Gichner T., Cabrera López, G., Wagner E.D., Plewa M.J. Induction of somatic mutations in Tradescantia clone 4430 by three phenylene isomers and the antimutagenic mechanisms of diethyldithiocarbamate and ammonium metavanadate. Mutat. Res. 306:1994;165-172.
17. Gichner T., Stavreva D.A., Čeřovská N., Wagner E.D., Plewa M.J. Metabolic activation of m-phenylenediamine to products mutagenic in Salmonella typhimurium by medium isolated from tobacco suspension cell cultures. Mutat. Res. 331:1995;127-132.
18. Hallahan D.L., West J.M. Cytochrome P-450 in plant/insect interactions: geraniol 10-hydroxylase and the biosynthesis of iridoid monoterpenoids. Drug Metabol. Drug Interact. 12:1995;369-382.
19. Hansíková H., Frei E., Anzenbacher P., Stiborová M. Isolation of plant cytochrome P-450 and NADPH: cytochrome P-450 reductase from tulip bulbs (Tulipa fosteriana L.) oxidizing xenobiotics. Gen. Physiol. Biophys. 13:1994;149-169.
20. Hansíková H., Frei E., Schmeiser H.H., Anzenbacher P., Stiborová M. A reconstituted cytochrome P450 system from tulip bulbs (Tulipa fosteriana L.) oxidizes xenobiotics. Plant Sci. 110:1995;53-61.
21. Higashi K. Metabolic activation of environmental chemicals by microsomal enzymes of higher plants. Mutat. Res. 197:1988;273-288.
22. Moreland D.E., Corbin F.T., McFarland J.E. Effects of safeners on the oxidation of multiple susbtrates by grain sorghum microsomes. Pestic. Biochem. Physiol. 45:1993;43-53.
23. Moreland D.E., Corbin F.T., McFarland J.E. Oxidation of multiple substrates by corn shoot microsomes. Pestic. Biochem. Physiol. 47:1993;206-214.
24. Nash T. The colorimetric estimation of formaldehyde by means of the Hantsch reaction. J. Biochem. 55:1953;416-421.
25. O'Keefe D.P., Leto K.J. Cytochrome P450 from the mesocarp of avocado (Persea americana). Plant Physiol. 89:1989;1141-1149.
26. Omura T., Sato R. The carbon monoxide-binding pigment of liver microsomes. Part I: Evidence for its hemoprotein nature. J. Biol. Chem. 239:1964;2370-2378.
27. Pflugmacher S., Sandermann H. Jr. Cytochrome P450 monooxygenases for fatty acids and xenobiotics in marine macroalgae. Plant Physiol. 117:1998;123-128.
28. Pierrel M.A., Batard Y., Kazmaier M., Mignotte-Vieux C., Durst F., Werck-Reichhart D. Catalytic properties of the plant cytochrome P450 CYP73 expressed in yeast. Substrate specificity of a cinnamate hydroxylase. Eur. J. Biochem. 224:1994;835-844.
29. Plewa M.J., Wagner E.D. Activation of promutagens by green plants. Annu. Rev. Genet. 27:1993;93-113.
30. Plewa M.J., Wagner E.D., Stavreva D.A., Gichner T. Plant activation and its role in environmental mutagenesis and antimutagenesis. Mutat. Res. 350:1996;163-171.
31. Riviére J.-L., Cabanne F. Animal and plant cytochrome P-450 systems. Biochimie. 69:1987;743-752.
32. Robineau T., Batard Y., Nedelkina S., Cabello-Hurtado F., LeRet M., Sorokine O., Didierjean L., Werck-Reichhart D. The chemically inducible plant cytochrome P450 CYP76B1 actively metabolizes phenylureas and other xenobiotics. Plant Physiol. 118:1998;1049-1056.
33. Sandermann H. Jr. Pesticide residues in food plants: the role of plant metabolism. Naturwissenschaften. 74:1987;573-578.
34. Sandermann H. Jr. Mutagenic activation of xenobiotics by plant enzymes. Mutat. Res. 197:1988;183-194.
35. Sandermann H. Jr. Plant metabolism of xenobiotics. Trends Biochem. Sci. 17:1992;82-84.
36. Sandermann H. Jr. Higher plant metabolism of xenobiotics: the "green liver" concept. Pharmacogenetics. 4:1994;225-241.
37. Schalk M., Batard Y., Sever A., Nedelkina S., Durst F., Werck-Reichhart D. Design of fluorescent substrates and potent inhibitors of CYP73As P450s that catalyze 4-hydroxylation of cinnamic acid in higher plants. Biochemistry. 36:1997;15253-15261.
38. Schuler M. Plant cytochrome P450 monooxygenases. Crit. Rev. Plant Sci. 15:1996;235-284.
39. Shannon L.M., Kay E., Lew J.Y. Peroxidase isozymes from horseradish roots. Part I: Isolation and physical properties. J. Biol. Chem. 241:1966;2166-2172.
40. Siminszky B., Corbin F.T., Ward E.R., Fleischmann T.J., Dewey R.E. Expression of a soyabean cytochrome P450 monooxygenase cDNA in yeast and tobacco enhances the metabolism of phenylurea herbicides. Proc. Natl. Acad. Sci. USA. 96:1999;1750-1755.
41. Sottocasa G.L., Kuylenstierna B., Ernster I., Bergstrand A. An electron transport system associated with the outer membrane of liver mitochrondria. J. Cell Biol. 32:1967;415-438.
42. Stavreva D.A., Wagner E.D., Plewa M.J., Gichner T. Characterization of a macromolecular matrix isolated from tobacco suspension cell cultures and its role in the activation of promutagenic m-phenylenediamine. Mutat. Res. 379:1997;191-199.
43. Stiborová M., Anzenbacher P. What are the principal enzymes oxidizing the xenobiotics in plants: cytochrome P-450 or peroxidases? (A hypothesis). Gen. Physiol. Biophys. 10:1991;209-216.
44. Stiborová M., Asfaw B., Anzenbacher P. Activation of carcinogens by peroxidase. Horseradish peroxidase-mediated formation of benzenediazonium ion from a non-aminoazo dye, 1-phenylazo-2-hydroxynaphthalene (Sudan I) and its binding to DNA. FEBS Lett. 232:1988;387-390.
45. Stiborová M., Asfaw B., Anzenbacher P., Leŝeticky L., Hodek P. The first identification of the benzenediazonium ion formation from a non-aminoazo dye, 1-phenylazo-2-hydroxynaphthalene (Sudan I) by microsomal enzymes of rat livers. Cancer Lett. 40:1988;319-326.
46. Stiborová M., Asfaw B., Frei E., Schmeiser H.H., Wiessler M. Benzenediazonium ion derived from Sudan I forms an 8-(phenylazo)guanine adduct in DNA. Chem. Res. Toxicol. 8:1995;489-498.
47. 32P-postlabelling of DNA adducts derived from peroxidative activation of carcinogenic non-aminoazo dye 1-phenylazo-2-hydroxynaphthalene (Sudan I). Carcinogenesis. 11:1990;1843-1848.
48. Stiborová M., Frei E., Schmeiser H.H., Wiessler M., Anzenbacher P. Peroxidase oxidizes N-nitrosomethylaniline to ultimate carcinogen(s) binding to DNA and transfer RNA in vitro. Cancer Lett. 63:1992;53-59.
49. Stiborová M., Hansíková H. Peroxidases from tulip bulbs (Tulipa fosteriana L.) oxidize xenobiotics N-nitrosodimethylamine and N-nitroso-N-methylaniline in vitro. Collect. Czech. Chem. Commun. 62:1997;1804-1814.
50. Thies F., Backhaus T., Bossmann B., Grimme L.H. Xenobiotic biotransformation in unicellular green algae. Involvement of cytochrome P450 in the activation and selectivity of the pyridazinone pro-herbicide metflurazon. Plant Physiol. 112:1996;361-370.
51. Tijet N., Helvig C., Pinot F., Le Bouquin R., Lesot A., Durst F., Salaun J.P., Benveniste I. Functional expression in yeast and characterization of a clofibrate-inducible plant cytochrome P-450 (CYP94A1) involved in cutin monomers synthesis. Biochem. J. 332:1998;583-589.
52. Urban P., Werck-Reichhart D., Teutsch H.G., Durst F., Regnier S., Kazmaier M., Pompon D. Characterization of recombinant plant cinnamate 4-hydroxylase produced in yeast. Kinetic and spectral properties of the major plant P450 of the phenylpropanoid pathways. Eur. J. Biochem. 222:1994;843-850.
53. Vermilion J.L., Coon M.J. Identification of the high and low potential flavins of liver microsomal NADPH-cytochrome P-450 reductase. J. Biol. Chem. 253:1978;8812-8819.