Brz220 interacts with DWF4, a cytochrome P450 monooxygenase in brassinosteroid biosynthesis, and exerts biological activity

Bioscience, Biotechnology and Biochemistry

Volumn 72, Issue 1, 2008, Pages 7-12

  Sekimata, Katsuhiko ^a   Ohnishi, Toshiyuki ^b   Mizutani, Masaharu ^b   Todoroki, Yasushi ^c   Han, Sun Young ^a   Uzawa, Jun ^a   Fujioka, Shozo ^a   Yoneyama, Koichi ^d   Takeuchi, Yasutomo ^c   Takatsuto, Suguru ^e   Sakata, Kanzo ^b   Yoshida, Shigeo ^a   Asami, Tadao ^a,f  

^a Japan Science and Technology Agency   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c SHIZUOKA UNIVERSITY   (Japan)

^d UTSUNOMIYA UNIVERSITY   (Japan)

^e JOETSU UNIVERSITY OF EDUCATION   (Japan)

^f UNIVERSITY OF TOKYO   (Japan)

Author keywords

Azole; Brassinosteroid; P450 inhibitor

Indexed keywords

BINDING AFFINITY; BRASSINOSTEROID (BR); HYPOCOTYL GROWTH; STEREOISOMERS;

BIOACTIVITY; BIOSYNTHESIS; ESCHERICHIA COLI; HYDROXYLATION; PROTEINS;

ENZYME ACTIVITY;

1 (2 (4 TRIFLUOROMETHYLPHENYL) 4 N PROPYL 1,3 DIOXOLAN 2 YLMETHYL) 1H 1,2,4 TRIAZOLE; 1,3 DIOXOLANE DERIVATIVE; 1-(2-(4-TRIFLUOROMETHYLPHENYL)-4-N-PROPYL-1,3-DIOXOLAN-2-YLMETHYL)-1H-1,2,4-TRIAZOLE; ARABIDOPSIS PROTEIN; BRASSINOLIDE; CHOLESTANOL; CYTOCHROME P450; DWF4 PROTEIN, ARABIDOPSIS; HETEROCYCLIC STEROID; PHYTOHORMONE; PHYTOSTEROL; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARABIDOPSIS; ARTICLE; DRUG EFFECT; ENZYMOLOGY; GROWTH, DEVELOPMENT AND AGING; METABOLISM; PLANT GROWTH;

ARABIDOPSIS; ARABIDOPSIS PROTEINS; CHOLESTANOLS; CYTOCHROME P-450 ENZYME SYSTEM; DIOXOLES; HYPOCOTYL; PHYTOSTEROLS; PLANT GROWTH REGULATORS; STEROIDS, HETEROCYCLIC; TRIAZOLES;

ARABIDOPSIS; ARABIDOPSIS THALIANA; ESCHERICHIA COLI;

EID: 38549105443     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.70141     Document Type: Article

References (20)

1. Verras, A., Kuntz, I. D., and Ortiz de Montellano, P. R., Computer-assisted design of selective imidazole inhibitor for cytochrome p450 enzyme. J. Med. Chem., 47, 3572-3579 (2004).
2. Burden, R. S., Cooke, D. T., and Carter, G. A., Inhibitors of sterol biosynthesis and growth in plants and fungi. Phytochemistry, 28, 1791-1804 (1989).
3. Cupp-Vickery, J. R., Garcia, C., Hofacre, A., and McGee-Estrada, K., Ketoconazole-induced conformational changes in the active site of cytochrome P450eryF. J. Mol. Biol., 311, 101-110 (2001).
4. Narasimhulu, S., Interactions of substrate and product with cytochrome P450 2B4. Biochemistry, 35, 1840-1847 (1996).
5. Asami, T., Mizutani, M., Fujioka, S., Goda, H., Min, Y. K., Shimada, Y., Nakano, T., Takatsuto, S., Matsuyama, T., Nagata, N., Sakata, K., and Yoshida, S., Selective interaction of triazole derivatives with DWF4, a cytochrome P450 monooxygenase of the brassinosteroid biosynthetic pathway, correlates with brassinosteroid deficiency in planta. J. Biol. Chem., 276, 25687-25691 (2001).
6. Sasse, J. M., Physiological actions of brassinosteroids. In "Brassinosteroids: Steroidal Plant Hormones," eds. Sakurai, A., Yokota, T., and Clouse, S. D., Springer, Tokyo, pp. 137-161 (1999).
7. Asami, T., and Yoshida, S., Brassinosteroid biosynthesis inhibitor. Trends Plant Sci., 4, 348-353 (1999).
8. Fujioka, S., and Yokota, T., Biosynthesis and metabolism of brassinosteroids. Annu. Rev. Plant Biol., 54, 137-164 (2003).
9. Ohnishi, T., Szatmari, A. M., Watanabe, B., Fujita, S., Bancos, S., Koncz, C., Lafos, M., Shibata, K., Yokota, T., Sakata, K., Szekeres, M., and Mizutani, M., C-23 hydroxylation by Arabidopsis CYP90C1 and CYP90D1 reveals a novel shortcut in brassinosteroid biosynthesis. Plant Cell, 18, 3275-3288 (2006).
10. Bancos, S., Nomura, T., Sato, T., Molnar, G., Bishop, G. J., Koncz, C., Yokota, T., Nagy, F., and Szekeres, M., Regulation of transcript levels of the Arabidopsis cytochrome P450 genes involved in brassinosteroid biosynthesis. Plant Physiol., 130, 504-513 (2002).
11. Goda, H., Shimada, Y., Asami, T., Fujioka, S., and Yoshida, S., Microarray analysis of brassinosteroid-regulated genes in Arabidopsis. Plant Physiol., 130, 1319-1334 (2002).
12. Tanaka, K., Asami, T., Yoshida, S., Nakamura, Y., Matsuo, T., and Okamoto, S., Brassinosteroid homeostasis in Arabidopsis is ensured by feedback expressions of multiple genes involved in its metabolism. Plant Physiol., 138, 1117-1125 (2005).
13. Sekimata, K., Han, S.-Y., Yoneyama, K., Takeuchi, Y., Yoshida, S., and Asami, T., A specific and potent inhibitor of brassinosteroid biosynthesis possessing a dioxolane ring. J. Agric. Food Chem., 50, 3486-3490 (2002).
14. Sekiamta, K., Uzawa, J., Han, S.-Y., Yoneyama, K., Takeuchi, Y., Yoshida, S., and Asami, T., Brz220 a novel brassinosteroid biosynthesis inhibitor: stereochemical structure-activity relationship. Tetrahedron: Asymmetry, 13, 1875-1878 (2002).
15. Fujita, S., Ohnishi, T., Watanabe, B., Yokota, T., Takatsuto, S., Fujioka, S., Yoshida, S., Sakata, K., and Mizutani, M., Arabidopsis CYP90B1 catalyses the early C-22 hydroxylation of C27, C28 and C29 sterols. Plant J., 45, 765-774 (2006).
16. CAChe, 3.11, Oxford Molecular Ltd., London, 1998.
17. Gaussian 03 Revision D.01, Gaussian, Inc., Wallingford CT, 2004.
18. Sekimata, K., Kimura, T., Kaneko, I., Nakano, T., Yoneyama, K., Takeuchi, Y., Yoshida, S., and Asami, T., A specific brassinosteroid biosynthesis inhibitor, Brz2001: evaluation of its effects on Arabidopsis, cress, tobacco, and rice. Planta, 213, 716-721 (2001).
19. Kushiro, M., Nakano, T., Sato, K., Yamagishi, K., Asami, T., Nakano, A., Takatsuto, S., Fujioka, S., Ebizuka, Y., and Yoshida, S., Obtusifoliol 14α-demethylase (CYP51) antisense Arabidopsis shows slow growth and long life. Biochem. Biophys. Res. Commun., 285, 98-104 (2001).
20. Fujioka, S., Li, J., Choi, Y.-H., Seto, H., Takatsuto, S., Noguchi, T., Watanabe, T., Kuriyama, H., Yokota, T., Chory, J., and Sakurai, A., Identification of castasterone, 6-deoxocastasterone, typhasterol and 6-deoxotyphasterol from the shoots of Arabidopsis thaliana. Plant Cell, 9, 1951-1962 (1997).