Cytochrome P450 CYP710A encodes the sterol C-22 desaturase in Arabidopsis and tomato

Plant Cell

Volumn 18, Issue 4, 2006, Pages 1008-1022

  Morikawa, Tomomi ^a   Mizutani, Masaharu ^b   Aoki, Nozomu ^b   Watanabe, Bunta ^b   Saga, Hirohisa ^a   Saito, Shigeki ^b   Oikawa, Akira ^a   Suzuki, Hideyuki ^c   Sakurai, Nozomu ^c   Shibata, Daisuke ^c   Wadano, Akira ^a   Sakata, Kanzo ^b   Ohta, Daisaku ^a  

^a Osaka Prefecture University   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c KAZUSA DNA RESEARCH INSTITUTE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DNA; GENES; PLANTS (BOTANY);

BRASSICASTEROL; CAMPESTEROL; GLUCURONIDASE; STIGMASTEROL;

PROTEINS;

GENES; NUCLEIC ACIDS; PLANTS; PROTEINS;

ARABIDOPSIS; ARABIDOPSIS THALIANA; FUNGI; LYCOPERSICON ESCULENTUM;

EID: 33745437728     PISSN: 10404651     EISSN: None     Source Type: Journal    
DOI: 10.1105/tpc.105.036012     Document Type: Article

References (49)

1. Alonso, J.M., et al. (2003). Genome-wide insertional mutagenesis of Arabidopsis thaliana. Science 301, 653-657.
2. Anastasia, M., Allevi, P., Ciuffreda, P., and Fiecchi, A. (1983). Stereoselective synthesis of crinosterol [(22E,24S)-ergosta-5,22-dien-3β- ol]. J. Chem. Soc. Perkin Trans. 1, 2365-2367.
3. Benveniste, P. (2004). Biosynthesis and accumulation of sterols. Annu. Rev. Plant Biol. 55, 429-457.
4. Borner, G.H., Sherrier, D.J., Weimar, T., Michaelson, L.V., Hawkins, N.D., Macaskill, A., Napier, J.A., Beale, M.H., Lilley, K.S., and Dupree, P. (2005). Analysis of detergent-resistant membranes in Arabidopsis. Evidence for plasma membrane lipid rafts. Plant Physiol. 137, 104-116.
5. Carland, F.M., Fujioka, S., Takatsuto, S., Yoshida, S., and Nelson, T. (2002). The Identification of CVP1 reveals a role for sterols in vascular patterning. Plant Cell 14, 2045-2058.
6. Clough, S.J., and Bent, A.F. (1998). Floral dip: A simplified method for Agrobacterium-mediated transformation of Arabidopsis thaliana. Plant J. 16, 735-743.
7. Clouse, S.D. (2000). Plant development: A role for sterols in embryogenesis. Curr. Biol. 10, 601-604.
8. Clouse, S.D. (2002). Brassinosteroid signal transduction: Clarifying the pathway from ligand perception to gene expression. Mol. Cell 10, 973-982.
9. Diener, A.C., Li, H., Zhou, W., Whoriskey, W.J., Nes, W.D., and Fink, G.R. (2000). Sterol methyltransferase 1 controls the level of cholesterol in plants. Plant Cell 12, 853-870.
10. Dyer, R.G., Metherington, C.S., Alberti, K.G.M.M., and Laker, M.F. (1995). Simultaneous measurement of phytosterols (campesterol and β-sitosterol) and 7-ketocholesterol in human lipoproteins by capillary column gas chromatography. J. Chromatogr. B 663, 1-7.
11. Gotoh, O. (1992). Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences. J. Biol. Chem. 267, 83-90.
12. Hakomori, S., Yamamura, S., and Handa, A.K. (1998). Signal transduction through glyco(sphingo)lipids. Introduction and recent studies on glyco(sphingo)lipid-enriched microdomains. Ann. N. Y. Acad. Sci. 845, 1-10.
13. Harder, T., and Simons, K. (1997). Caveolae, DIGs, and the dynamics of sphingolipid-cholesterol microdomains. Curr. Opin. Cell Biol. 9, 534-542.
14. He, J.X., Fujioka, S., Li, T.C., Kang, S.G., Seto, H., Takatsuto, S., Yoshida, S., and Jang, J.C. (2003). Sterols regulate development and gene expression in Arabidopsis. Plant Physiol. 131, 1258-1269.
15. Jang, J.C., Fujioka, S., Tasaka, M., Seto, H., Takatsuto, S., Ishii, A., Aida, M., Yoshida, S., and Sheen, J. (2000). A critical role of sterols in embryonic patterning and meristem programming revealed by the fackel mutants of Arabidopsis thaliana. Genes Dev. 14, 1485-1497.
16. Jefferson, R. (1987). Assaying chimeric genes in plants: The GUS gene fusion system. Plant Mol. Biol. Rep. 5, 387-405.
17. Kelly, S.L., Lamb, D.C., Baldwin, B.C., Corran, A.J., and Kelly, D.E. (1997). Characterization of Saccharomyces cerevisiae CYP61, sterol delta22-desaturase, and inhibition by azole antifungal agents. J. Biol. Chem. 272, 9986-9988.
18. 25-crinosterol side chain construction. Steroids 67, 597-603.
19. Kim, H.B., Schaller, H., Goh, C.-H., Kwon, M., Choe, S., An, C.S., Durst, F., Feldmann, A., and Feyereisen, R. (2005). Arabidopsis cyp57 mutant shows postembryonic seedling lethality associated with lack of membrane integrity. Plant Physiol. 138, 2033-2047.
20. Kimura, M. (1983). The Neutral Theory of Molecular Evolution. (Cambridge, UK: Cambridge University Press).
21. Lang, R.W., and Djerassi, C. (1982). Stereochemical aspects of acid-catalyzed cyclopropane ring-opening reactions. A stereospecific pathway to crinosterol and brassicasterol. Helv. Chim. Acta 65, 407-418.
22. Lindsey, K., Pullen, M.L., and Topping, J.F. (2003). Importance of plant sterols in pattern formation and hormone signalling. Trends Plant Sci. 8, 521-525.
23. Matsumoto, T., Shimizu, N., Shigemoto, T., Itoh, T., Iida, T., and Nishioka, A. (1983). Isolation of 22-dehydrocampesterol from the seeds of Brassica juncea. Phytochemistry 22, 789-790.
24. Meunier, B., de Visser, S.P., and Shaik, S. (2004). Mechanism of oxidation reactions catalyzed by cytochrome P450 enzymes. Chem. Rev. 104, 3947-3980.
25. Mizutani, M., and Ohta, D. (1998). 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.
26. Mizutani, M., Ohta, D., and Sato, R. (1997). 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.
27. Mongrand, S., Morel, J., Laroche, J., Claverol, S., Carde, J.P., Hartmann, M.A., Bonneu, M., Simon-Plas, F., Lessire, R., and Bessoule, J.J. (2004). Lipid rafts in higher plant cells: Purification and characterization of Triton X-100-insoluble microdomains from tobacco plasma membrane. J. Biol. Chem. 279, 36277-36286.
28. Nairn, C.J., Winsett, L., and Ferl, R.J. (1988). Nucleotide sequence of an actin gene from Arabidopsis thaliana. Gene 65, 247-257.
29. Nelson, D.R., Schuler, M.A., Paquette, S.M., Werck-Reichhart, D., and Bak, S. (2004). Comparative genomics of rice and Arabidopsis. Analysis of 727 cytochrome P450 genes and pseudogenes from a monocot and a dicot. Plant Physiol. 135, 756-772.
30. Nemhauser, J.L., and Chory, J. (2004). BRing it on: New insights into the mechanism of brassinosteroid action. J. Exp. Bot. 55, 265-270.
31. Nes, W.D., Norton, R.A., Crumley, F.G., Madigan, S.J., and Katz, E.R. (1990). Sterol phylogenesis and algal evolution. Proc. Natl. Acad. Sci. USA 87, 7565-7569.
32. Noguchi, T., Fujioka, S., Takatsuto, S., Sakurai, A., Yoshida, S., Li, J., and Chory, J. (1999). Arabidopsis det2 is defective in the conversion of (24fi)-24-methylcholest-4-en-3-one to (24fi)-24-methyl-5α-cholestan-3-one in brassinosteroid biosynthesis. Plant Physiol. 120, 833-840.
33. Parry-Smith, D.J., Payne, A.W.R., Michie, A.D., and Attwood, T.K. (1998). CINEMA - A novel colour INteractive editor for multiple alignments. Gene 221, GC57-GC63.
34. Saito, S., Hirai, N., Matsumoto, C., Ohigashi, H., Ohta, D., Sakata, K., and Mizutani, M. (2004). Arabidopsis CYP707AS encode (+)-abscisic acid 8′-hydroxylase, a key enzyme in the oxidative catabolism of abscisic acid. Plant Physiol. 134, 1439-1449.
35. Saitou, N., and Nei, M. (1987). The neighbor-joining method: A new method for reconstructing phylogenetic trees. Mol. Biol. Evol. 4, 406-425.
36. Salimova, E., Boschetti, A., Eichenberger, W., and Lutova, L. (1999). Sterol mutants of Chlamydomonas reinhardtii: Characterisation of three strains deficient in C24(28) reductase. Plant Physiol. Biochem. 37, 241-249.
37. Sambrook, J., Fritsch, E.F., and Maniatis, T. (1989). Molecular Cloning: A Laboratory Manual. (Cold Spring Harbor, NY: Cold Spring Harbor Laboratory Press).
38. Schaeffer, A., Bronner, R., Benveniste, P., and Schaller, H. (2001). The ratio of campesterol to sitosterol that modulates growth in Arabidopsis is controlled by STEROL METHYLTRANSFERASE 2;1. Plant J. 25, 605-615.
39. Schaller, H. (2003). The role of sterols in plant growth and development. Prog. Lipid Res. 42, 163-175.
40. Schrick, K., Fujioka, S., Takatsuto, S., Stierhof, Y.D., Stransky, H., Yoshida, S., and Jurgens, G. (2004). A link between sterol biosynthesis, the cell wall, and cellulose in Arabidopsis. Plant J. 38, 227-243.
41. Schrick, K., Mayer, U., Horrichs, A., Kuhnt, C., Bellini, C., Dangl, J., Schmidt, J., and Jurgens, G. (2000). FACKEL is a sterol C-14 reductase required for organized cell division and expansion in Arabidopsis embryogenesis. Genes Dev. 14, 1471-1484.
42. Schrick, K., Mayer, U., Martin, G., Bellini, C., Kuhnt, C., Schmidt, J., and Jurgens, G. (2002). Interactions between sterol biosynthesis genes in embryonic development of Arabidopsis. Plant J. 31, 61-73.
43. Schuler, M.A., and Werck-Reichhart, D. (2003). Functional genomics of P450S. Annu. Rev. Plant Biol. 54, 629-667.
44. Skaggs, B.A., Alexander, J.F., Pierson, C.A., Schweitzer, K.S., Chun, K.T., Koegel, C., Barbuch, R., and Bard, M. (1996). Cloning and characterization of the Saccharomyces cerevisiae C-22 sterol desaturase gene, encoding a second cytochrome P-450 involved in ergosterol biosynthesis. Gene 169, 105-109.
45. Souter, M., Topping, J., Pullen, M., Friml, 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.
46. Takatsuto, S., Watanabe, T., Fujioka, S., and Sakurai, A. (1997). Synthesis of new naturally occurring 6-deoxo brassinosteroids. J. Chem. Res. Synop. 134-135, Miniprint 901-924.
47. Thompson, J.D., Higgins, D.G., and Gibson, T.J. (1994). CLUSTAL W: Improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res. 22, 4673-4680.
48. Valvekens, D., Montagu, M.V., and Lusebettens, M.V. (1998). Agrobacterium tumefaciens-mediated transformation of Arabidopsis thaliana root expiants by using kanamycin selection. Proc. Natl. Acad. Sci. USA 85, 5536-5540.
49. Willemsen, V., Friml, J., Grebe, M., van den Toorn, A., Palme, K., and Scheres, B. (2003). Cell polarity and PIN protein positioning in Arabidopsis require STEROL METHYLTRANSFERASE1 function. Plant Cell 15, 612-625.