Dual positional substrate specificity of rice allene oxide synthase-1: insight into mechanism of inhibition by type II ligand imidazole
2
조회
0
다운로드
1
인용
0
참고문헌
키워드
초록
Phylogenetic and amino acid sequence analysis indicated that rice allene oxide synthase-1 (OsAOS1) is CYP74, and is clearly distinct from CYP74B, C and D subfamilies. Regio- and stereo-chemical analysis revealed the dual substrate specificity of OsAOS1 for (cis,trans)-configurational isomers of 13(S)- and 9(S)-hydroperoxyoctadecadienoic acid. GC-MS analysis showed that OsAOS1 converts 13(S)- and 9(S)-hydroperoxyoctadecadi(tri)enoic acid into their corresponding allene oxide. UV-Visible spectral analysis of native OsAOS1 revealed a Soret maximum at 393 nm, which shifted to 424 nm with several clean isobestic points upon binding of OsAOS1 to imidazole. The spectral shift induced by imidazole correlated with inhibition of OsAOS1 activity, implying that imidazole may coordinate to ferric heme iron, triggering a heme-iron transition from high spin state to low spin state. The implications and significance of a putative type II ligand-induced spin state transition in OsAOS1 are discussed.
Abstract
Phylogenetic and amino acid sequence analysis indicated that rice allene oxide synthase-1 (OsAOS1) is CYP74, and is clearly distinct from CYP74B, C and D subfamilies. Regio- and stereo-chemical analysis revealed the dual substrate specificity of OsAOS1 for (cis,trans)-configurational isomers of 13(S)- and 9(S)-hydroperoxyoctadecadienoic acid. GC-MS analysis showed that OsAOS1 converts 13(S)- and 9(S)-hydroperoxyoctadecadi(tri)enoic acid into their corresponding allene oxide. UV-Visible spectral analysis of native OsAOS1 revealed a Soret maximum at 393 nm, which shifted to 424 nm with several clean isobestic points upon binding of OsAOS1 to imidazole. The spectral shift induced by imidazole correlated with inhibition of OsAOS1 activity, implying that imidazole may coordinate to ferric heme iron, triggering a heme-iron transition from high spin state to low spin state. The implications and significance of a putative type II ligand-induced spin state transition in OsAOS1 are discussed.
참고문헌 (30)
- Brash, A. R., "Lipoxygenases: occurrence, functions, catalysis, and acquisition of substrate", J. Biol. Chem, 274, pp.23679~23682 (1999)
- Siedow, J. N., "Plant lipoxygenases: structure and function", Annu. Rev. Plant. Physiol. Plant. Mol. Biol, 42, pp.145~188 (1991)
- Veldink, G. A., "The enzymatic conversion of linoleic acid hydroperoxide by flax-seed hydroperoxide isomerase", Biochem. J, 120, pp.55~60 (1970)
- Hamberg, M, "Oxylipin pathway to jasmonates: biochemistry and biological significance", Biochim. Biophys. Acta, 1165, pp.1~18 (1992)
- Grechkin, A., "Recent development in biochemistry of the plant lipoxygenase pathway", Prog. Lipid Res, 37, pp.317~352 (1998)
- Grechkin, A. N., "Tomato CYP74C3 is a multifunctional enzyme not only synthesizing allene oxide but also catalyzing its hydrolysis and cyclization", Chembiochem, 9, pp.2498~2505 (2008)
- Hughes, R. K., "Plant cytochrome CYP74 family: biochemical features, endocellular localization, activation mechanism in plant defense and improvements for industrial applications", Chembiochem, 10, pp.1122~1133 (2009)
- Mueller, M. J., "Enzymes involved in jasmonic acid biosynthesis", Physiol. Plant, 100, pp.653~663 (1997)
- Beale, M. H., "Jasmonates: key players in the plant defense", Nat. Prod. Rep, 15, pp.533~548 (1998)
- Schaller, F., "Enzymes of the biosynthesis of octadecanoid- derived signaling molecules", J. Exp. Bot, 52, pp.11~23 (2001)
- Lee, D. S., "Structural insights into the evolutionary paths of oxylipin biosynthetic enzymes", Nature, 455, pp.363~368 (2008)
- Song, W. C., "Molecular cloning of an allene oxide synthase: A cytochrome P450 specialized for the metabolism of fatty acid hydroperoxides", Proc. Natl. Acad. Sci. U.S.A, 90, pp.8519~8523 (1993)
- Howe, G. A., "Cytochrome P450-dependent metabolism of oxylipins in tomato: cloning and expression of allene oxide synthase and fatty acid hydroperoxide lyase", Plant Physiol, 123, pp.711~724 (2000)
- Hughes, R. K., "Allene oxide synthase from Arabidopsis thaliana (CYP74A1) exhibits dual specificity that is regulated by monomer- micelle association", FEBS Letters, 580, pp.4188~4194 (2006)
- Itoh, A., "Identification of a jasmonate-regulated allene oxide synthase that metabolizes 9-hydroperoxides of linoleic and linolenic acids", J. Biol. Chem, 277, pp.46051~46058 (2002)
- Maucher, H., "Allene oxide synthases of barley (Hordeum vulgare cv. Salome): tissue specific regulation in seedling development", Plant J, 21, pp.199~213 (2000)
- Brash, A. R., "Mechanistic aspects of CYP74 allene oxide synthases and related P450 enzymes", Phytochem Rev, 70, pp.1522~1531 (2009)
- Jefoate, C. R. E., "Ligand interactions with hemoprotein P-450. II. Influence of phenobarbital and methylcholanthrene induction processes on P-450 spectra", Biochemistry, 8, pp.3464~3472 (1969)
- Song, W. C., "Purification of an allene oxide synthase and identification of the enzyme as a cytochrome P-450", Science, 253, pp.781~784 (1991)
- Locuson, C. W., "Visible spectra of type II cytochrome P450-drug complexes: evidence that “incomplete” heme coordination is common", Drug. Metab. Dispos, 35, pp.614~622 (2007)
- Agrawal, G. K., "Rice octadecanoid pathway", Biochem. Biophys. Res. Commun, 317, pp.1~15 (2004)
- Agrawal, G. K., "Molecular cloning and mRNA expression analysis of the first rice jasmonate biosynthetic pathway gene allene oxide synthase", Plant Physiol. Biochem, 40, pp.771~782 (2002)
- Ha, S. B., "Molecular characterization of the gene encoding rice allene oxide synthase and its expression", Biosci. Biotechnol. Biochem, 66, pp.2719~2722 (2002)
- Kim, E. S., "Dual positional specificity and expression of non-traditional lipoxygenase induced by wounding and methyl jasmonate in maize seedlings", Plant Mol. Biol, 52, pp.1203~1213 (2003)
- Jang, S., "Regiochemical and stereochemical evidence for enzyme- initiated catalysis in dual positional specific maize lipoxygenase-1", Org. Lett, 9, pp.3113~3116 (2007)
- Oh, K., "Design and synthesis of novel imidazole derivatives as potent inhibitors of allene oxide synthse (CYP74)", Bioorg. Med. Chem, 10, pp.3707~3711 (2002)
- Wasternack, C, "Jasmonates : Structural requirements for lipid-derived signals active in plant stress responses and development", ACS Chem. Biol, 5, pp.63~77 (2010)
- Hoa, G. H. B., "The formation of cytochrome P-450 from chtochrome P-420 is promoted by spermine", Biochemistry, 29, pp.6810~6815 (1990)
- Vick, B. A., "A spectrophotometric assay for hydroperoxide lyase", Lipids, 26, pp.315~320 (1991)
- Cho, K. B., "The reaction mechanism of allene oxide synthase: Interplay of theoretical QM", MM calculations and experimental investigations, 2011, pp.507, 14~25