Allene oxide synthase from Arabidopsis thaliana (CYP74A1) exhibits dual specificity that is regulated by monomer-micelle association

FEBS Letters

Volumn 580, Issue 17, 2006, Pages 4188-4194

  Hughes, Richard K ^a   Belfield, Eric J ^a   Ashton, Ruth ^a   Fairhurst, Shirley A ^a   Göbel, Cornelia ^b   Stumpe, Michael ^b   Feussner, Ivo ^b   Casey, Rod ^a  

^a JOHN INNES CENTRE   (United Kingdom)

^b UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Detergent; Hydroperoxide; Metabolism; Micelle; Oxylipin; P450

Indexed keywords

ALLENE OXIDE SYNTHASE; CYTOCHROME P450 4A1; DETERGENT; HEME; MONOMER; SYNTHETASE; UNCLASSIFIED DRUG;

ARABIDOPSIS; ARTICLE; DENSITY GRADIENT CENTRIFUGATION; ENZYME ACTIVITY; ENZYME SPECIFICITY; IN VITRO STUDY; IRON BINDING CAPACITY; MICELLE; NONHUMAN; PRIORITY JOURNAL; PROTEIN BINDING;

ARABIDOPSIS; ARABIDOPSIS PROTEINS; CYTOCHROME P-450 ENZYME SYSTEM; DETERGENTS; INTRAMOLECULAR OXIDOREDUCTASES; KINETICS; MICELLES; SUBSTRATE SPECIFICITY;

ARABIDOPSIS THALIANA;

EID: 33745835735     PISSN: 00145793     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.febslet.2006.06.075     Document Type: Article

References (28)

1. Laudert D.L., Pfannschmidt U., Lottspeich F., Hollander-Czytko H., and Weiler E.W. Cloning, molecular and functional characterisation of Arabidopsis thaliana allene oxide synthase (CYP74), the first enzyme of the octadecanoid pathway to jasmonates. Plant Mol. Biol. 31 (1996) 323-335
2. Feussner I., and Wasternack C. The lipoxygenase pathway. Ann. Rev. Plant Physiol. Plant Mol. Biol. 53 (2002) 275-297
3. Song W.-C., Funk C.D., and Brash A.R. Molecular cloning of an allene oxide synthase: a cytochrome P450 specialised for the metabolism of fatty acid hydroperoxides. Proc. Natl. Acad. Sci. USA 90 (1993) 8519-8523
4. Veldink G.A., Vliegenthart J.F.G., and Boldingh J. The enzymic conversion of linoleic acid hydroperoxide by flax-seed hydroperoxide isomerase. Biochem. J. 120 (1970) 55-60
5. Pan Z., Camara B., Gardner H.W., and Backhaus R.A. Aspirin inhibition and acetylation of the plant cytochrome P450, allene oxide synthase, resembles that of animal prostaglandin endoperoxide H synthase. J. Biol. Chem. 273 (1998) 18139-18145
6. Song W.-C., and Brash A.R. Purification of an allene oxide synthase and identification of the enzyme as a cytochrome P-450. Science 253 (1991) 781-784
7. Pan Z., Durst F., Werck-Reichhart D., Gardner H.W., Camara B., Cornish K., and Backhaus R.A. The major protein of guayule rubber particles is a cytochrome P450. J. Biol. Chem. 270 (1995) 8487-8494
8. Utsunomiya Y., Nakayama T., Oohira H., Hirota R., Mori T., Kawai F., and Ueda T. Purification and inactivation by substrate of an allene oxide synthase (CYP74) from corn (Zea mays L.) seeds. Phytochem. 53 (2000) 319-323
9. Maucher H., Hause B., Feussner I., Ziegler J., and Wasternack C. Allene oxide synthases of barley (Hordeum vulgare cv. Salome): tissue specific regulation in seedling development. Plant J. 21 (2000) 199-213
10. Howe G.A., Lee G.I., Itoh A., Li L., and DeRocher A.E. Cytochrome P450-dependent metabolism of oxylipins in tomato: cloning and expression of allene oxide synthase and fatty acid hydroperoxide lyase. Plant Physiol. 123 (2000) 711-724
11. Itoh A., Schilmiller A.L., McCaig B.C., and Howe G.A. Identification of a jasmonate-regulated allene oxide synthase that metabolises 9-hydroperoxides of linoleic and linolenic acids. J. Biol. Chem. 277 (2002) 46051-46058
12. Oldham M.L., Brash A.R., and Newcomer M.E. The structure of coral allene oxide synthase reveals a catalase adapted for metabolism of a fatty acid hydroperoxide. Proc. Natl. Acad. Sci. USA 102 (2005) 297-302
13. Koljak R., Boutaud O., Shieh B.-H., Samel N., and Brash A.R. Identification of a naturally occurring peroxidase-lipoxygenase fusion protein. Science 277 (1997) 1994-1996
14. Froehlich J.E., Itoh A., and Howe G.A. Tomato allene oxide synthase and fatty acid hydroperoxide lyase, two cytochrome P450s involved in oxylipin metabolism, are targeted to different membranes of chloroplast envelope. Plant Physiol. 125 (2001) 306-317
15. Hughes R.K., Belfield E.J., Muthusamay M., Khan A., Rowe A., Harding S.E., Fairhurst S.A., Bornemann S., Ashton R., Thorneley R.N.F., and Casey R. Characterisation of Medicago truncatula hydroperoxide lyase (CYP74C3), a water-soluble detergent-free cytochrome P450 monomer whose biological activity is defined by monomer-micelle association. Biochem. J. 395 (2006) 641-652
16. Emanuelsson O., Nielsen H., and von Heijne G. ChloroP, a neural network-based method for predicting chloroplast transit peptides and their cleavage sites. Prot. Sci. 8 (1999) 978-984
17. Vick B.A. A spectrophotometric assay for hydroperoxide lyase. Lipids 26 (1991) 315-320
18. Aasa R., and Vanngard T. EPR signal intensity and powder shapes - re-examination. J. Magn. Res. 19 (1975) 308-315
19. Berry E.A., and Trumpower B. Simultaneous determination of haems a, b, and c from pyridine haemochrome spectra. Anal. Biochem. 161 (1987) 1-15
20. Bradford M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72 (1976) 248-254
21. Helenius A., and Simons K. Solubilisation of membranes by detergents. Biochem. Biophys. Acta 415 (1975) 29-79
22. Stumpe, M., Göbel, C., Demchenko, K., Hoffmann, M., Klösgen, R.B., Pawlowski, K. and Feussner, I. (2006) Identification of an allene oxide synthase (CYP74C) that leads to formation of α-ketols from 9-hydroperoxides of linoleic and linolenic acid in below ground organs of potato. Plant J. (in press).
23. Oh K., and Murofushi N. Design and synthesis of novel imidazole derivatives as potent inhibitors of allene oxide synthase (CYP74). Bioorg. Med. Chem. 10 (2002) 3707-3711
24. Boutaud O., and Brash A.R. Purification and catalytic activities of the two domains of the allene oxide synthase-lipoxygenase fusion protein of the coral Plexaura homomalla. J. Biol. Chem. 274 (1999) 33764-33770
25. Wang C.X., Avdiushko S., and Hildebrand D.F. Over-expression of a cytoplasm-localised allene oxide synthase promotes the wound-induced accumulation of jasmonic acid in transgenic tobacco. Plant Mol. Biol. 40 (1999) 783-793
26. Joyard J., Teyssier E., Miege C., Berny-Seigneurin D., Marechal E., Block M.A., Dorne A.J., Rolland N., Ajlani G., and Douce R. The biochemical machinery of plastid envelope membranes. Plant Physiol. 118 (1998) 715-723
27. Smolka M.B., Martins D., Winck F.V., Santoro C.E., Castellari R.R., Ferrari F., Brum I.J., Galembeck E., Coletta H.D., Machado M.A., Marangoni S., and Novello J.C. Proteome analysis of the plant pathogen Xylella fastidiosa reveals major cellular and extracellular proteins and a peculiar codon bias distribution. Proteomics 2 (2003) 224-237
28. Setubal J.C., Moreira L.M., and da Silva A.C.R. Bacterial phytopathogens and genome science. Curr. Opin. Microbiol. 8 (2005) 595-600