Identification of essential amino acid residues in a sterol 8,7-isomerase from Zea mays reveals functional homology and diversity with the isomerases of animal and fungal origin

Biochemical Journal

Volumn 414, Issue 2, 2008, Pages 247-259

  Rahier, Alain ^a   Pierre, Sylvain ^a   Riveill, Geneviève ^b   Karst, Francis ^b  

^a CNRS   (France)

^b UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Inhibition; Mutagenesis; Plant sterol; Sterol 8,7 isomerase

Indexed keywords

ALCOHOLS; AMINES; AMINO ACIDS; ORGANIC ACIDS; YEAST;

INHIBITION; MUTAGENESIS; PLANT STEROL; STEROL 8,7-ISOMERASE; ZEA MAYS;

LOUDSPEAKERS;

AMMONIA; ASPARTIC ACID; ERGOSTEROL; ESSENTIAL AMINO ACID; GLUTAMINE; HISTIDINE; ISOMERASE; METHYL GROUP; RECOMBINANT ENZYME; STEROL 8,7 ISOMERASE; TRYPTOPHAN;

ARTICLE; CATALYSIS; COMPARATIVE GENE MAPPING; CONTROLLED STUDY; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME KINETICS; ENZYME SPECIFICITY; ENZYME STRUCTURE; ENZYME SUBSTRATE COMPLEX; EXPRESSED SEQUENCE TAG; GENETIC VARIABILITY; HUMAN; IN VITRO STUDY; IN VIVO STUDY; LIPOPHILICITY; MAIZE; MICROSOME; MOLECULAR CLONING; MOLECULAR LIBRARY; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; SACCHAROMYCES CEREVISIAE; SEQUENCE ALIGNMENT; SEQUENCE HOMOLOGY; STEROL ANALYSIS; STEROL SYNTHESIS;

AMINO ACID SEQUENCE; AMINO ACIDS; ANIMALS; BLOTTING, WESTERN; FUNGI; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; MUTAGENESIS, SITE-DIRECTED; MUTATION; PLANT PROTEINS; RECOMBINANT PROTEINS; SEQUENCE HOMOLOGY, AMINO ACID; STEROID ISOMERASES; STEROLS; SUBSTRATE SPECIFICITY; TRANSITION TEMPERATURE; VARIATION (GENETICS); ZEA MAYS;

ANIMALIA; FUNGI; SACCHAROMYCES CEREVISIAE; ZEA MAYS;

EID: 50949103202     PISSN: 02646021     EISSN: None     Source Type: Journal    
DOI: 10.1042/BJ20080292     Document Type: Article

References (41)

1. Benveniste, P. (2004) Biosynthesis and accumulation of sterols. Annu. Rev. Plant Physiol. Plant Mol. Biol. 55, 429-457
2. Bouvier, F., Rahier, A. and Camara, B. (2005) Biogenesis, molecular regulation and function of plant isoprenoids. Prog. Lipid Res. 44, 357-429
3. Lees, N. D., Skaggs, B., Kirsch, D. R. and Bard, M. (1995) Cloning of the late genes in the ergosterol biosynthetic pathway of Saccharomyces cerevisiae. Lipids 30, 221-226
4. Wilton, D. C., Rahimtula, A. D. and Akhtar, M. (1969) The reversibility of the A8-cholestenol-Δ7-cholestenol isomerase reaction in cholesterol biosynthesis. Biochem. J. 114, 71-73
5. Akhtar, M., Rahimtula, A. D. and Wilton, D. C. (1970) The stereochemistry of hydrogen elimination from C7 in cholesterol and ergosterol biosynthesis. Biochem. J. 117, 539-542
6. Caspi, E. and Ramm. P. J. (1969) Stereochemical differences in the biosynthesis of C27-Δ7-steroidal intermediates. Tetrahedron Lett. 10, 181-185
7. Bimpson, T., Goad, L. J. and Goodwin, T. W. (1969) The stereochemistry of hydrogen elimination at C-7,C-22 and C-23 during the conversion of cholesterol (cholest-5-en-3 beta-ol) into cholesta-5,7,22-trien-3 beta-ol by Tetrahymena pyriformis. Biochem. J. 115, 857-858
8. 7 isomerization and methyl transfer of sterols in ergosterol biosynthesis of yeast. J. Biochem. (Tokyo) 85, 1531-1537
9. Soustre, I., Dupuy, P. H., Silve, S., Karst, F. and Loison, G. (2000) Sterol metabolism and ERG2 gene regulation in the yeast Saccharomyces cerevisiae. FEBS Lett, 470, 102-106
10. Rahier, A. and Taton, M. (1997) Fungicides as tools in studying postsqualene sterol synthesis in plants. Pest. Biochem. Physiol. 57, 1-27
11. 3H]ifenprodil. Mol. Pharmacol. 54, 591-598
12. 14-reductase by tenpropimorph, tridemorph and fenpropidin in cell-free enzyme systems from Saccharomyces cerevisiae. Phytochemistry 26, 663-668
13. Konig, K. H., Pommer, E. H. and Sanne, W. (1965) N-substituted tetrahydro-1,4-oxazines: a new class of fungicidal compounds, Angew. Chem. Int. Ed. 4, 336-341
14. Himmerle, W. and Pommer, E. H. (1980) 3-phenylpropylamines, a new class of systemic fungicides. Angew. Chem. Int. Ed. 19, 184-189
15. 7-sterol isomerase and of cydoeucalenol-obtusifoliol isomerase by N-benzyl-B-aza-4α, 10-dimethyl-trans-decal-3β-ol, an analogue of a carbocationic high energy intermediate. Phytochemistry 24, 1223-1232
16. Silve, S., Leplatois, P., Josse, A., Dupuy, P. H., Lanau, C., Kaghad, M., Dhers, C., Picard, C., Rahier, A., Talon, M. et al. (1996) The immunosuppressant SR 31747 blocks cell proliferation by inhibiting a steroid isomerase in Saccharomyces cerevisiae. Mol. Cell. Biol. 16, 2719-2727
17. Silve, S., Dupuy, P. H., Labit-Lebouteiller, C., Kaghad, M., Chalon, P., Rainier, A., Taton, M., Lupkev, J., Shire, D. and Loison, G. (1996) Emopamil-binding protein a mammalian protein that binds a series of structurally diverse neuroprotective agents, exhibits Δ8-Δ7 sterol isomerase activity in yeast. J. Biol. Chem. 271, 22434-22440
18. Grebenok, R. J., Ohnmeiss, T. E., Yamamoto, A., Huntley, E. D., Galbraith, W. and Delia Penna, D. (1998) Isolation and characterization of an Arabidopsis thaliana C-8,7 sterol isomerase; functional and structural similarities to mammalian C8,7 sterol isomerase/ emopamil-binding protein. Plant Mol. Biol. 38, 807-815
19. Ashman, W. H., Barbuch, R. J., Ulbright, C. E., Jarrett, H. W. and Bard, M. (1991) Cloning and disruption of the yeast C-8 sterol isomerase gene. Lipids 26, 628-432
20. 1+ antagonist binding protein. Molecular cloning, tissue distribution, and heterologous expression. J. Biol. Chem. 270, 7551-7557
21. Braverman, N., Lin, P. Moebius, F. F., Obie, C., Moser, A., Glossmann, H., Wilcox, W. R., Rimoin, D. L., Smith, M., Kratz, L. et al. (1999) Mutations in the gene encoding 3 β-hydroxysteroid-Δ8, Δ7-isomerase cause x-linked dominant Conradi-Hünermann syndrome. Nat. Genet. 22, 291-294
22. Derry, J. M., Gormally, E., Means, G. D., Zhao, W., Meindl, A., Kelley, R. I., Boyd, Y. and Heiman, G. E. (1999) Mutations in a ΔB-Δ7 sterol isomerase in the tattered mouse and x-linked dominant chondrodysplasia punctata. Nat. Genet. 22, 286-290
23. Grange, D. K., Kratz, L. E., Braverman, N. E. and Kelley, R. I. (2000) Child syndrome caused by deficiency of 3,6-hydroxysteroid-ΔB, Δ7-isomerase, Am. J. Med. Genet. 90, 328-335
24. Moebius, F. F., Soellner, K. E. M., Fiechtner, B., Huck, C. W., Bonn, G. and Glossmann, H. (1999) Histidine77, glutamic acid81, threonine126, asparagine194, and tryptophan197 of the human emopamil binding protein are required for in vivo sterol Δ8-Δ7 isomerization, Biochemistry 38, 1119-1127
25. 1-binding sites for sterol isomerization inhibitors: evidence for a pharmacological relationship with the yeast sterol C8-C7 isomerase, Br. J. Pharmacol. 121, 1-6
26. Souter, M, Topping, J., Pullen, M., Frimi, J., Palme, K., Hackett, R., Grierson, D. and Lindsey, K. (2002) Hydra mutants of Arabidopsis are defective in sterol profiles and auxin and ethylene signaling. Plant Cell 14, 1017-1031
27. Taton, M., Benveniste, P. and Rahier, A.(1986) IV-[(1,5,9)-trimethyldecyl]-4α, 10- dimethyl-8-aza-trans-decal-3β-ol, a novel potent inhibitor of 2,3-oxidosqualene cycloartenol and lanosterol cyclases. Biochem. Biophys. Res. Commun. 138, 764-770
28. Vernet, T., Dignard, D. and Thomas, D. Y. (1987) A family of yeast expression vectors containing the phage f1 intergenic region. Gene 52, 225-233
29. Gietz, D., St Jean, A., Woods, R. A. and Schiestl, R. H. (1992) Improved method for high efficiency transformation of intact yeast cells. Nucleic Acid Res. 20, 1425-1432
30. Rahier, A. and Benveniste, P. (1989) Mass spectral identification of phytosterols. In Analysis of Sterols and Other Significant Steroids (Nes, W. D. and Parish, E., eds.), pp. 223-250, Academic Press, New York
31. Schmitt, P. and Benveniste, P. (1979) Effect of AY-9944 on sterol biosynthesis in suspension cultures of bramble cells. Phytochemistry 18, 445-450
32. Darnet, S. and Rahier, A. (2003) Enzymological properties of sterol-C4-methyl-oxidase of yeast sterol biosynthesis. Biochem. Biophys. Acta 1633, 106-117
33. Talon, M. and Rahier, A., (1991) Properties and structural requirements for substrate specificity of cytochrome P-450-dependent obtusifoliol 14α-demethylase from maize (Zea mays) seedlings. Biochem. J. 277, 483-492
34. 14-reductase in higher plants. Characterization and inhibition by analogues of a presumptive carbocationic intermediate of the reduction reaction. Eur. J. Biochem. 185, 607-614
35. Ouggleby, R. G. (1984) Regression analysis of nonlinear Arrhenius plots: an empirical model and a computer program. Comput. Biol. Med. 14, 447-455
36. Rahier, A, Taton, M. and Benveniste, P. (1990) Inhibition of sterol biosynthesis enzymes in vitro by analogues of high-energy carbocationic intermediates. Biochem. Soc. Trans. 18, 48-52
37. Bradford, M. (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72, 248-254
38. Nes, W. D., Zhou, W., Dennis, A. L., Li. H., Jia, Z., Keith, R. A., Piser, T. M. and Furlong, S. T. (2002) Purification, characterization and catalytic properties of human sterol 8-isomerase. Biochem. J. 367, 587-599
39. Dvornik, D., Kraml, M., Dubuc, J., Givner, M. and Gaudry, R. (1963) A novel mode of inhibition of cholesterol biosynthesis. J. Am. Chem. Soc. 85, 3309
40. Derocq, J. M., Bourrie, B., Segui, M., Le Fur, G. and Casellas. P. (1995) In vivo inhibition of endotoxin-induced pro-inflammatory cytokines production by the sigma ligand SR 31747. J. Pharmacol. Exp. Ther. 272, 224-230
41. Jordan, V. C. (2003) Tamoxifen: a most unlikely pioneering medicine. Nat. Rev. Drug Discov. 2, 205-213