Redundancy or flexibility: Molecular diversity of the electron transfer components for P450 monooxygenases in higher plants

Frontiers in Bioscience

Volumn 9, Issue , 2004, Pages 1587-1597

  Ohta, Daisaku ^a   Mizutani, Masaharu ^b  

^a Osaka Prefecture University   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Arabidopsis; Cytochrome; Cytochrome b5; Ferredoxin; Metabolic engineering; P450; Reductase; Review

Indexed keywords

CYTOCHROME B5; CYTOCHROME B5 REDUCTASE; FERREDOXIN; FLAVOPROTEIN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE FERRIHEMOPROTEIN REDUCTASE; STEROID 11BETA MONOOXYGENASE; UNSPECIFIC MONOOXYGENASE; CYTOCHROME C; CYTOCHROME C5; CYTOCHROME P450; FERREDOXIN NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE REDUCTASE; MITOCHONDRIAL PROTEIN; MULTIENZYME COMPLEX; VEGETABLE PROTEIN;

ARABIDOPSIS; BIOCHEMISTRY; ENZYME REGULATION; ENZYME SPECIFICITY; GEL BLOT ANALYSIS; GENE INDUCTION; MOLECULAR BIOLOGY; NONHUMAN; PLANT; REVIEW; SIGNAL TRANSDUCTION; AMINO ACID SEQUENCE; CHEMISTRY; CHLOROPLAST; ENZYMOLOGY; GENE EXPRESSION REGULATION; GENETICS; METABOLISM; MOLECULAR GENETICS; PHYSIOLOGY;

ARABIDOPSIS; EMBRYOPHYTA;

AMINO ACID SEQUENCE; CHLOROPLASTS; CYTOCHROME C GROUP; CYTOCHROME P-450 ENZYME SYSTEM; ELECTRON TRANSPORT CHAIN COMPLEX PROTEINS; FERREDOXIN-NADP REDUCTASE; FERREDOXINS; GENE EXPRESSION REGULATION, PLANT; MITOCHONDRIAL PROTEINS; MOLECULAR SEQUENCE DATA; NADPH-FERRIHEMOPROTEIN REDUCTASE; PLANT PROTEINS; PLANTS;

EID: 2442664418     PISSN: 27686701     EISSN: 27686698     Source Type: Journal    
DOI: 10.2741/1356     Document Type: Review

References (70)

1. Morant, M., S. Bak, B.L. Moller & D. Werck-Reichhart: Plant cytochromes P450: tools for pharmacology, plant protection and phytoremediation. Curr Opin Biotechnol 14, 151-162 (2003)
2. Schuler, M.A. & D. Werck-Reichhart: Functional genomics of P450s. Annu Rev Plant Biol 54, 629-667 (2003)
3. Mizutani, M., D. Ohta & R. Sato: Purification and characterization of a cytochrome-P450 (trans-cinnamic acid 4-hydroxylase) from ethiolated mung bean seedlings. Plant Cell Physiol 34, 481-488 (1993)
4. Bolwell, G.P., K. Bozak & A. Zimmerlin: Plant cytochrome P450. Phytochemistry 37, 1491-1506 (1994)
5. Ponnamperuma, K. & R. Croteau: Purification and characterization of an NADPH-cytochrome P450 (cytochrome c) reductase from spearmint (Mentha spicata) glandular trichomes. Arch Biochem Biophys 329, 9-16 (1996)
6. Kahn, R.A., S. Bak, I. Svendsen, B.A. Halkier & B.L. Moller: Isolation and reconstitution of cytochrome P450ox and in vitro reconstitution of the entire biosynthetic pathway of the cyanogenic glucoside dhurrin from sorghum. Plant Physiol 115, 1661-1670 (1997)
7. Mizutani, M., D. Ohta & R. Sato: Isolation of a cDNA and a genomic clone encoding cinnamate 4-hydroxylase from Arabidopsis and its expression manner in planta. Plant Physiol 113, 755-763 (1997)
8. Mizutani, M. & D. Ohta: Two isoforms of NADPH:cytochrome P450 reductase in Arabidopsis thaliana. Gene structure, heterologous expression in insect cells and differential regulation. Plant Physiol 116, 357-367 (1998)
9. 5 is required for full activity of flavonoid 3′, 5′-hydroxylase, a cytochrome P450 involved in the formation of blue flower colors. Proc Natl Acad Sci USA 96, 778-783 (1999)
10. Benveniste, I., A. Lesot, M.P. Hasenfratz, G. Kochs & F. Durst: Multiple forms of NADPH-cytochrome P450 reductase in higher plants. Biochem Biophys Res Commun 177, 105-112 (1991)
11. Menting, J.G., E. Cornish & R.K. Scopes: Purification and partial characterization of NADPH-cytochrome c reductase from Petunia hybrida flowers. Plant Physiol 106, 643-650 (1994)
12. Shet, M.S., K. Sathasivan, M.A. Arlotto, M.C. Mehdy & R.W. Estabrook: Purification, characterization, and cDNA cloning of an NADPH-cytochrome P450 reductase from mung bean. Proc Natl Acad Sci USA 90, 2890-2894 (1993)
13. Meijer, A.H., M.I.L. Cardoso, J.T. Voskuilen, A. de Waal, R. Verpoorte & J.H.C. Hoge: Isolation and characterization of a cDNA clone from Catharanthus roseus encoding NADPH-cytochrome P450 reductase, an enzyme essential for reactions catalyzed by cytochrome P450 monooxygenases in plants. Plant J 4, 47-60 (1993)
14. Yamada, T., H. Imaishi, A. Oka & H. Ohkawa: Molecular cloning and expression in Saccharomyces cerevisiae of tobacco NADPH-cytochrome P450 oxidoreductase cDNA. Biosci Biotechnol Biochem 62, 1403-1411 (1998)
15. Koopmann, E. & K. Hahlbrock: Differentially regulated NADPH:cytochrome P450 oxidoreductases in parsley. Proc Natl Acad Sci USA 94, 14954-14959 (1997)
16. Rosco, A., H.H. Pauli, W. Priesner & T.M. Kutchan: Cloning and heterologous expression of NADPH-cytochrome P450 reductases from the Papaveraceae. Arch Biochem Biophys 348, 369-377 (1997)
17. Urban, P., C. Mignotte, M. Kazmaier, F. Delorme & D. Pompon: Cloning, yeast expression, and characterization of the coupling of two distantly related Arabidopsis thaliana NADPH-cytochrome P450 reductases with P450 CYP73A5. J Biol Chem 272, 19176-19186 (1997)
18. Ro, D.K., J. Ehlting & C.J. Douglas: Cloning, functional expression, and subcellular localization of multiple NADPH-cytochrome P450 reductases from hybrid poplar. Plant Physiol 130, 1837-1851 (2002)
19. Cardoso, M.I., A.H. Meijer, F. Rueb, J.A. Machado, J. Memelink & J.H. Hoge: A promoter region that controls basal and elicitor-inducible expression levels of the NADPH:cytochrome P450 reductase gene (Cpr) from Catharanthus roseus binds nuclear factor GT-1. Mol Gen Genet 256, 674-681 (1997)
20. Ryals, J.A., U.H. Neuenschwander, M.G. Willits, A. Molina, H.-Y. Steiner & M.D. Hunt: Systemic Acquired Resistance. Plant Cell 8, 1809-1819 (1996)
21. Kunkel, B.N., A.F. Bent, D. Dahlbeck, R.W. Innes & B.J. Staskawicz: RPS2, an Arabidopsis disease resistance locus specifying recognition of Pseudomonas syringae strains expressing the avirulence gene avrRpt2. Plant Cell 5, 865-875 (1993)
22. Zhou, N., T.L. Tootle & J. Glazebrook: Arabidopsis PAD3, a gene required for camalexin biosynthesis, encodes a putative cytochrome P450 monooxygenase. Plant Cell 11, 2419-2428 (1999)
23. Irmler, S., G. Schroder, B. St-Pierre, N.P. Crouch, M. Hotze, J. Schmidt, D. Strack, U. Matern & J. Schroder: Indole alkaloid biosynthesis in Catharanthus roseus: new enzyme activities and identification of cytochrome P450 CYP72A1 as secologanin synthase. Plant J 24, 797-804 (2000)
24. Maleck, K., A. Levine, T. Eulgem, A. Morgan, J. Schmid, K.A. Lawton, J.L. Dangl & R.A. Dietrich: The transcriptome of Arabidopsis thaliana during systemic acquired resistance. Nat Genet 26, 403-410 (2000)
25. Chandok, M.R., A.J. Ytterberg, K.J. van Wijk & D.F. Klessig: The pathogen-inducible nitric oxide synthase (iNOS) in plants is a variant of the P protein of the glycine decarboxylase complex. Cell 113, 469-482 (2003)
26. Guo, F.Q., M. Okamoto & N.M. Crawford: Identification of a plant nitric oxide synthase gene involved in hormonal signaling. Science 302, 100-103 (2003)
27. Paine, M.J., A.P. Garner, D. Powell, J. Sibbald, M. Sales, N. Pratt, T. Smith, D.G. Tew & C.R. Wolf: Cloning and characterization of a novel human dual flavin reductase. J Biol Chem 275, 1471-1478 (2000)
28. Kwasnicka, D.A., A. Krakowiak, C. Thacker, C. Brenner & S.R. Vincent: Coordinate expression of NADPH-dependent flavin reductase, Fre-1, and Hint-related 7meGMP-directed hydrolase, DCS-1. J Biol Chem 278, 39051-39058 (2003)
29. Olteanu, H. & R. Banerjee: Redundancy in the pathway for redox regulation of mammalian methionine synthase: reductive activation by the dual flavoprotein, novel reductase 1. J Biol Chem 278, 38310-38314 (2003)
30. Ranocha, P., F. Bourgis, M.J. Ziemak, D. Rhodes, D.A. Gage & A.D. Hanson: Characterization and functional expression of cDNAs encoding methionine-sensitive and-insensitive homocysteine S-methyltransferases from Arabidopsis. J Biol Chem 275, 15962-15968 (2000)
31. Azpiroz-Leehan, R & K.A. Feldmann: T-DNA insertion mutagenesis in Arabidopsis: going back and forth. Trends Genet 13:152-156 (1997)
32. Krysan, P.J., J.C. Young, P.J. Jester, S. Monson, G. Copenhaver, D. Preuss & M.R. Sussman: Characterization of T-DNA insertion sites in Arabidopsis thaliana and the implications for saturation mutagenesis. OMICS 6, 163-174 (2002)
33. Grinberg, A.V., F. Hannemann, B. Schiffler, J. Müller, U. Heinemann & R. Bernhardt: Adrenodoxin: structure, stability, and electron transfer properties. Proteins 40, 590-612 (2000)
34. Vickery, L.E: Molecular recognition and electron transfer in the mitochondrial steroid hydroxylase system. Steroids 62, 124-127 (1997)
35. Barros, M.H. & F.G. Nobrega: YAH1 of Saccharomyces cerevisiae: a new essential gene that codes for a protein homologous to human adrenodoxin. Gene 233, 197-203 (1991)
36. Manzella, L., M.H. Barros & F.G. Nobrega: ARH1 of Saccharomyces cerevisiae: a new essential gene that codes for a protein homologous to the human adrenodoxin reductase. Yeast 14, 839-846 (1998)
37. Lange, H., A. Kaut, G. Kispal & R. Lill: A mitochondrial ferredoxin is essential for biogenesis of cellular iron-sulfur proteins. Proc Natl Acad Sci USA 97, 1050-1055 (2000)
38. Li, J., S. Saxena, D. Pain & A. Dancis: Adrenodoxin reductase homolog (Arh1p) of yeast mitochondria required for iron homeostasis. J Biol Chem 276, 1503-1509 (2001)
39. Takahashi, Y. & M. Nakamura: Functional assignment of the OKF2-iscS-iscU-iscA-hscB-hscA-fdx-ORF3 gene cluster involved in the assembly of Fe-S clusters in Escherichia coli. J Biochem 126, 917-926 (1999)
40. Lill, R. & G. Kispal: Maturation of cellular Fe-S proteins: an essential function of mitochondria. Trends Biochem Sci 25, 352-356 (2000)
41. Takubo, K., T. Morikawa, Y. Nonaka, M. Mizutani, S. Takenaka, K. Takabe, M.A. Takahashi & D. Ohta: Identification and molecular characterization of mitochondrial ferredoxins and ferredoxin reductase from Arabidopsis. Plant Mol Biol 52, 817-830 (2003)
42. + reductases: a basal structural framework and a multiplicity of functions. FASEB J 11, 133-140 (1997)
43. Mizutani, M., E. Ward & D. Ohta: Cytochrome P450 superfamily in Arabidopsis thaliana: isolation of cDNAs, differential expression, and RFLP mapping of multiple cytochromes P450. Plant Mol Biol 37, 39-52 (1998)
44. Xu, W., S. Bak, A. Decker, S.M. Paquette, R. Feyereisen & D.W. Galbraith: Microarray-based analysis of gene expression in very large gene families: the cytochrome P450 gene superfamily of Arabidopsis thaliana. Gene 272, 61-74 (2001)
45. Lindemann, P. & M. Luckner: Biosynthesis of pregnan derivatives in somatic embryos of Digitalis lantana. Photochemistry 46, 507-513 (1997)
46. Mühlenhoff, U. & R. Lill: Biogenesis of iron-sulfur proteins in eukaryotes: a novel task of mitochondria that is inherited from bacteria. Biochim Biophys Acta 1459, 370-382 (2000)
47. Tong, W.H. & T. Rounalt: Distinct iron-sulfur cluster assembly complexes exist in the cytosol and mitochondria of human cells. EMBO J 21, 5592-5700 (2000)
48. Kushnir, S., E. Babiychuk, S. Storozhenko, M. Davey, J. Papenbrock, R.R. De Rycke, G. Engler, U. Stephan, H. Lange, G. Kispal, R. Lill & M.M. van Montagu: A Mutation of the mitochondrial ABC transporter Sta1 leads to dwarfism and chlorosis in the Arabidopsis mutant starik. Plant Cell 13, 89-100 (2001)
49. Kruft, V., H. Eubel, L. Jänsch, W. Werhahn & H.-P. Braun: Proteomic approach to identify novel mitochondrial proteins in Arabidopsis. Plant Physiol 127, 1694-1710 (2001)
50. Millar, A.H., L.J. Sweetlove, P. Giegé & C.J. Leaver: Analysis of the Arabidopsis mitochondrial proteome. Plant Physiol 127, 1711-1727 (2001)
51. Song, W.C., C.D. Funk & A.R. Brash: Molecular cloning of an allene oxide synthase: a cytochrome P450 specialized for the metabolism of fatty acid hydroperoxides. Proc Natl Acad Sci USA 90, 8519-8523 (1993)
52. Matsui, K., M. Shibutani, T. Hase & T. Kajiwara: Bell pepper fruit fatty acid hydroperoxide lyase is a cytochrome P450 (CYP74B). FEBS Lett 394, 21-24 (1996)
53. Laudert, D., U. Pfannschmidt, F. Lottspeich, H. Hollander-Czytko & E.W. Weiler: Cloning, molecular and functional characterization of Arabidopsis thaliana allene oxide synthase (CYP74), the first enzyme of the octadecanoid pathway to jasmonates. Plant Mol Biol 31, 323-335 (1994)
54. Helliwell, C.A., J.A. Sullivan, R.M. Mould, J.C. Gray, W.J. Peacock & E.S. Dennis: A plastid envelope location of Arabidopsis ent-kaurene oxidase links the plastid and endoplasmic reticulum steps of the gibberellin biosynthesis pathway. Plant J 28, 201-208 (2001)
55. Watson, C.J., J.E. Froehlich, C.A. Josefsson, C. Chapple, F. Durst, I. Benveniste & R.C. Coolbaugh: Localization of CYP86B1 in the outer envelope of chloroplasts. Plant Cell Physiol 42, 873-878 (2001)
56. Lacour, T. & H. Ohkawa: Engineering and biochemical characterization of the rat microsomal cytochrome P4501A1 fused to ferredoxin and ferredoxin-NADP (+) reductase from plant chloroplasts. Biochim Biophys Acta 1433, 87-102 (1999)
57. Smith, M.A., A.R. Cross, O.T.G. Jones, W.T. Griffiths, S. Stymne & K. Stobart: Electron-transport components of the 1acyl-2-oleoyl-sn-glycero-3- phosphocholine delta 12-desaturase (delta 12-desaturase) in microsomal preparations from developing safflower (Carthamus tinctorius L.) cotyledons. Biochem J 272, 23-29 (1990)
58. 5 in delta 12-desaturation of oleic acid by microsomes of safflower (Carthamus tinctorius L.). Arch Biochem Biophys 284, 431-436 (1991)
59. 5 in 4alpha-methyl-oxidation and C5(6) desaturation of plant sterol precursors. Biochem Biophys Res Commun 236, 434-437 (1997)
60. 5 are necessary for its targeting to the endoplasmic reticulum. EMBO J 11, 4197-203 (1992)
61. 5 reductase from Arabidopsis. Plant Physiol 119, 353-362 (1999)
62. 5 reductases. Plant J 24, 645-654 (2001)
63. 5 reductase requires myristic acid for association with outer mitochondrial but not ER membranes. J Cell Biol 135, 1501-1513 (1996)
64. 5 reductase. J Cell Biol 117, 975-986 (1992)
65. Srere, P.A: Complexes of sequential metabolic enzymes. Annu Rev Biochem 56, 89-124 (1987)
66. Srivastava, D.K. & S.A. Bernhard: Biophysical chemistry of metabolic reaction sequences in concentrated enzyme solution and in the cell. Annu Rev Biophys Biophys Chem 116, 175-204 (1987)
67. Ovadi, J. & P.A. Srere: Metabolic consequences of enzyme interactions. Cell Biochem Funct 14, 249-258 (1996)
68. Chappell, J: The Biochemistry and Molecular Biology of Isoprenoid Metabolism. Plant Physiol 107, 1-6 (1995)
69. Winkel-Shirley, B: Evidence for enzyme complexes in the phenylpropanoid and flavonoid pathways. Physiol Plant 107, 142-149 (1999)
70. Liu, C.J. & R.A. Dixon: Elicitor-induced association of isoflavone O-methyltransferase with endomembranes prevents the formation and 7-O-methylation of daidzein during isoflavonoid phytoalexin biosynthesis. Plant Cell 13, 2643-2458 (2003)