Fatty acid hydroperoxide lyase in tomato fruits: Cloning and properties of a recombinant enzyme expressed in escherichia coli

Bioscience, Biotechnology and Biochemistry

Volumn 64, Issue 6, 2000, Pages 1189-1196

  Matsui, Kenji ^a   Miyahara, Chinatsu ^a   Wilkinson, Jack ^b   Hiatt, Bill ^b   Knauf, Vic ^b   Kajiwara, Tadahiko ^a  

^a YAMAGUCHI UNIVERSITY   (Japan)

^b Calgene LLC   (United States)

Author keywords

Cytochrome P450; Fatty acid hydroperoxide lyase; Tomato (Lycopersicon esculentum)

Indexed keywords

COMPLEMENTARY DNA; CYTOCHROME P450; HEME; HYDROPEROXIDE LYASE; LYASE; PLANT DNA; PRIMER DNA; RECOMBINANT PROTEIN;

AMINO ACID SEQUENCE; ARTICLE; CHEMISTRY; DRUG ANTAGONISM; ENZYME SPECIFICITY; ENZYMOLOGY; ESCHERICHIA COLI; GENETICS; ISOLATION AND PURIFICATION; METABOLISM; MOLECULAR CLONING; MOLECULAR GENETICS; NUCLEOTIDE SEQUENCE; TOMATO;

ALDEHYDE-LYASES; AMINO ACID SEQUENCE; BASE SEQUENCE; CLONING, MOLECULAR; CYTOCHROME P-450 ENZYME SYSTEM; DNA PRIMERS; DNA, COMPLEMENTARY; DNA, PLANT; ESCHERICHIA COLI; HEME; LYCOPERSICON ESCULENTUM; MOLECULAR SEQUENCE DATA; RECOMBINANT PROTEINS; SUBSTRATE SPECIFICITY;

EID: 0034203126     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.64.1189     Document Type: Article

References (40)

1. Blee, E., Phytooxylipins and plant defense reactions. Prog. Lipid Res., 37, 33-72 (1998).
2. leaves inoculated with Pseudomonas syringae pv phaseolicola. Plant Physiol, 101, 13-24 (1993).
3. Bate, N. J. and Rothstein, S. J., C6-volatiles derived from the lipoxygenase pathway induce a subset of defense-related genes. Plant J., 16, 561-569 (1998).
4. Song, W. C. and Brash, A. R., Purification of an al-lene oxide synthase and identification of the enzyme as a cytochrome P-450. Science, 253, 781-784 (1991).
5. Song, W. C., Funk, C. D., and Brash, A. R., 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).
6. Shibata, Y., Matsui, K., Kajiwara, T., and Hatana-ka, A., Purification and properties of fatty acid hydroperoxide lyase from green bell pepper fruits. Plant Cell Physiol, 36, 147-156 (1995).
7. Matsui, K., Shibutani, M., Hase, T., and Kajiwara, T., Bell pepper fatty acid hydroperoxide lyase is a cytochrome P450. FEBS Lett., 394, 21-24 (1996).
8. Matsui, K., Wilkinson, J., Hiatt, B., Knauf, V., and Kajiwara, T., Molecular cloning and expression of Arabidopsis fatty acid hydroperoxide lyase. Plant Cell Physiol., 40, 477-481 (1999).
9. Bate, N. J., Sivasankar, S., Moxon, C., Riley, J. M. C., Thompson, J. E., and Rothstein, S. J., Molecular characterization of an Arabidopsis gene encoding hydroperoxide lyase, a cytochrome P-450 that is wound inducible. Plant Physiol, 117, 1393-1400 (1998).
10. Laudert, D., Pfannschmidt, U., Lottspeich, F., Hollander-Czytko, H., and Weiler, E. W., Cloning, molecular and functional characterization of Arabidopsis thaliana allene oxide synthase (CYP74), the first enzyme of the octadecanoid pathway to jas-monates. Plant Mol. Biol., 31, 323-335 (1996).
11. Porter, T. D. and Coon, M. J., Cytochrome P-450. Multiplicity of isoforms, substrates, and catalytic and regulatory mechanisms. J. Biol. Chem., 266, 13469-13472 (1991).
12. Roberts, E. S., Vaz, A. D. N., and Coon, M. J., Catalysis by cytochrome P-450 of an oxidative reaction in xenobiotic aldehyde metabolism: deformyla-tion with olefin formation. Proc. Natl. Acad. Sci. USA, 88, 8963-8966 (1991).
13. Swinney, D. C. and Mak, A. Y., Androgen formation by cytochrome P450 CYP17. Solvent isotope effect and pL studies suggest a role for protons in the regulation of oxene versus peroxide chemistry. Biochemistry, 33, 2185-2190 (1994).
14. 2 biosynthesis. J. Biol. Chem., 264, 141-150 (1989).
15. Gardner, H. W. and Plattner, R. D., Linoleate hydroperoxides are cleaved heterolytically into aldehydes by a Lewis acid in aprotic solvent. Lipids, 19, 294-299 (1984).
16. lsO-laveled 13-hydroperoxylinoleyl alcohol into 12-hydroxy-(3Z)-dodecenal in tea chloroplasts. Z. Naturforsch., 41c, 359-362 (1986).
17. Buttery, R. G., Teranishi, R., Flath, R. A., and Ling, L. C., Fresh tomato volatiles. In “Flavor Chemistry”, eds. Teranishi, R., Buttery, R. G., and Shahidi, F., American Chemical Society, Washington, D. C., pp. 213-222 (1989).
18. Konrad, L., Andreas, M., and Natasha, S., European patent application, EP 0 801 133 A2 (1997).
19. Altschul, S. F., Gish, W., Miller, W., Myers, E. W., and Lipman, D. J., Basic local alignment search tool. J. Mol. Biol., 215, 403-410 (1990).
20. Dulley, J. R. and Grieve, P. A., Simple technique for eliminating interference by detergents in the Lowry method of protein determination. Anal. Biochem., 64, 136-141 (1975).
21. 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, 8487-8494 (1995).
22. Vaz, A. D. N., McGinnity, D. F., and Coon, M. J., Epoxidation of olefins by cytochrome P450: evidence from site-specific mutagenesis for hydroperoxo-iron as an electrophilic oxidant. Proc. Natl. Acad. Sci. USA, 95, 3555-3560 (1998).
23. Schalk, M., Nedelkina, S., Schoch, G., Batard, Y., and Werck-Reichhart, D., Role of unusual amino acid residues in the proximal and distal heme regions of a plant P450, CYP73A1. Biochemistry, 38, 6093-6103 (1999).
24. Blee, E. and Joyard, J., Envelope membranes from spinach chloroplasts are a site of metabolism of fatty acid hydroperoxides. Plant Physiol., 110, 445-454 (1996).
25. Donaldson, R. P. and Luster, D. G., Multiple forms of plant cytochromes P-450. Plant Physiol., 96, 669-674 (1991).
26. Matsui, K., Toyota, H., Kajiwara, T., Kakuno, T., and Hatanaka, A., Fatty acid hydroperoxide cleaving enzyme, hydroperoxide lyase, from tea leaves. Phytochemistry, 30, 2109-2113 (1991).
27. Wang, C., Chin, C. K., Ho, C. T., Hwang, C. F., Polashock, J. J., and Martin, C. E., Changes of fatty acids and fatty acid-derived flavor compounds by expressing the yeast A-9 desaturase gene in tomato. J. Agric. Food Chem., 44, 3399-3402 (1996).
28. Hatanaka, A., Kajiwara, T., Matsui, K., and Kitamura, A., Expression of lipoxygenase and hydroperoxide lyase activities in tomato fruits. Z. Naturforsch., 47c, 369-374 (1992).
29. Haugen, D. A. and Coon, M. J., Properties of elec-trophoretically homogeneous phenobarbital-induci-ble and /Lnaphthoflavone-inducible forms of liver microsomal cytochrome P-450. J. Biol. Chem., 251, 7929-7939 (1976).
30. Itoh, A. and Vick, B. A., The purification and characterization of fatty acid hydroperoxide lyase in sunflower. Biochim. Biophys. Acta, 1436, 531-540 (1999).
31. Lau, S. M. C., Harder, P. A., and O’Keefe, D. P., Low carbon monoxide affinity allene oxide synthase is the predominant cytochrome P450 in many plant tissues. Biochemistry, 32, 1945-1950 (1993).
32. Shibata, Y., Matsui, K., Kajiwara, T., and Hatanaka, A., Fatty acid hydroperoxide lyase is a heme protein. Biochem. Biophys. Res. Commun., 207, 438-443 (1995).
33. Kemal, C., Louis-Flamberg, P., Krupinski-Olsen, R., and Shorter, A. L., Reductive inactivation of soybean lipoxygenase 1: a possible mechanism for regulation of lipoxygenase activity. Biochemistry, 26, 7064-7072 (1987).
34. Barr, D. P., Martin, M. V., Guengerich, F. P., and Mason, R. P., Reaction of cytochrome P450 with cumene hydroperoxide: ESR spin-trapping evidence for the homolytic scission of the peroxide 0-0 bond by ferric cytochrome P450 1A2. Chem. Res. Toxicol., 9, 318-325 (1996).
35. Gerwick, W. H., Epoxy ally lie carbocations as conceptual intermediates in the biogenesis of diverse marine oxylipinds. Lipids, 31, 1215-1231 (1996).
36. Pan, Z., Camara, B., Gardner, H. W., and Backhaus, R. A., Aspirin inhibition and acétylation of the plant cytochrome P450, allene oxide synthase, resembles that of animal prostaglandin endoperoxide H synthase. J. Biol. Chem., 273, 18139-18145 (1998).
37. Marnet, L. J., Rowlinson, S. W., Goodwin, D. C., Kalgutkar, A. S., and Lanzo, C. A., Arachidonic acid oxygenation by COX-1 and COX-2. J. Biol. Chem., 274, 22903-22906 (1999).
38. Vidakovic, M., Sligar, S. G., Li, H., and Poulos, T. L., Understanding the role of the essential Asp251 in cytochrome P450cam using site-directed mutagenesis, crystallography, and kinetic solvent isotope effect. Biochemistry, 37, 9211-9219 (1998).
39. Matsui, K., Kajiwara, T., and Hatanaka, A., Inactivation of tea leaf hydroperoxide lyase by fatty acid hydroperoxide. J. Agric. Food Chem., 40, 175-178 (1992).
40. Yao, K., Falick, A. M., Patel, N., and Correia, M. A., Cumene hydroperoxide-mediated inactivation of cytochrome P450 2B1. J. Biol. Chem., 268, 59-65 (1993).