Peroxygenase-catalyzed fatty acid epoxidation in cereal seeds: Sequential oxidation of linoleic acid into 9(S),12(S),13(S)-trihydroxy-10(E)-octadecenoic acid

Plant Physiology

Volumn 110, Issue 3, 1996, Pages 807-815

  Hamberg, Mats ^a   Hamberg, Gunvor ^a  

^a KAROLINSKA INSTITUTE   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

AVENA SATIVA; HORDEUM; HORDEUM DISTICHUM; HORDEUM VULGARE; HORDEUM VULGARE SUBSP. VULGARE; SECALE CEREALE; TRITICUM AESTIVUM;

EID: 0030067147     PISSN: 00320889     EISSN: None     Source Type: Journal    
DOI: 10.1104/pp.110.3.807     Document Type: Article

References (34)

1. Blée E, Durst F (1987) Hydroperoxide-dependent sulfoxidation catalyzed by soybean microsomes. Arch Biochem Biophys 254: 43-52
2. Blée E, Schuber F (1990) Efficient epoxidation of unsaturated fatty acids by a hydroperoxide-dependent oxygenase. J Biol Chem 265: 12887-12894
3. Blée E, Wilcox AL, Marnett LJ, Schuber F (1993) Mechanism of reaction of fatty acid hydroperoxides with soybean peroxygenase. J Biol Chem 268: 1708-1715
4. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72: 248-254
5. Croteau R, Kolattukudy PE (1975) Enzymatic epoxidation of 18-hydroxyoleic acid to 18-hydroxy-cis-9,10-epoxystearic acid by a particulate preparation from spinach (Spinacia oleracea). Arch Biochem Biophys 170: 61-72
6. Esterbauer H, Schauenstein E (1977) Isomeric trihydroxy-octadecenoic acids formed upon enzymic oxidation of linoleic acid by barley flour. Monatshefte für Chemie 108: 963-972
7. Fahlstadius P, Hamberg M (1989) A gas-liquid chromatographic method for steric analysis of epoxy acids. Chem Phys Lipids 51: 15-22
8. Gardner HW (1988) Lipoxygenase pathway in cereals. In Y Pomeranz, ed, Advances in Cereal Science and Technology, Vol 9. American Association of Cereal Chemists, St. Paul, MN, pp 161-215
9. Gardner HW (1991) Recent investigations into the lipoxygenase pathway of plants. Biochim Biophys Acta 1084: 221-239
10. Gardner HW, Hamberg M (1993) Oxygenation of (3Z)-nonenal to (2E)-4-hydroxy-2-nonenal in the broad bean (Vicia faba L.). J Biol Chem 268: 6971-6977
11. Graveland A (1970) Enzymatic oxidations of linoleic acid and glycerol-1-monolinoleate in doughs and flour-water suspendons. J Am Oil Chem Soc 47: 352-361
12. Hamberg M (1971) Steric analysis of hydroperoxides formed by lipoxygenase oxygenation of linoleic acid. Anal Biochem 43: 515-526
13. Hamberg M (1989) Fatty acid hydroperoxide isomerase in Saprolegnia parasitica: structural studies of epoxy alcohols formed from isomeric hydroperoxyoctadecadienoates. Lipids 24: 249-255
14. Hamberg M (1991a) Regio- and stereochemical analysis of trihy-droxyoctadecenoic acids derived from linoleic acid 9- and 13-hydroperoxides. Lipids 26: 407-415
15. Hamberg M (1991b) Trihydroxyoctadecenoic acids in beer: qualitative and quantitative analysis. J Agric Food Chem 39: 1568-1572
16. Hamberg M (1995) Hydroperoxide isomerases. J Lipid Mediators Cell Signalling 12: 283-292
17. Hamberg M, Fahlstadius P (1992) On the specificity of a fatty acid epoxygenase in broad bean (Vicia faba L.). Plant Physiol 99: 987-995
18. Hamberg M, Gotthammar B (1973) A new reaction of unsaturated fatty acid hydroperoxides: formation of 11-hydroxy-12,13-epoxy-9-octadecenoic acid from 13-hydroperoxy-9,11-octadecadienoic acid. Lipids 8: 737-744
19. Hamberg M, Hamberg G (1990) Hydroperoxide-dependent epoxidation of unsaturated fatty acids in the broad bean (Vicia faba L.). Arch Biochem Biophys 283: 409-416
20. s-hydroperoxy-5,8,11,13-eicosatetraenoic acid. Biochim Biophys Acta 877: 447-457
21. Heimann W, Dresen P (1973) Enzymatic hydroperoxide degradation in cereals, enzyme characterization and reaction products. Helv Chim Acta 56: 463-469
22. Heimann W, Dresen P, Schreier P (1973) The lipoxygenase"lipoperoxidase"-system in cereals. Isolation of two protein complexes with lipoxygenase and linoleic acid hydroperoxide activity from oats and soybeans. Z Lebensm Unters-Forsch 152: 147-151
23. Heimann W, Klaiber V (1977) Hydroperoxide degradation by oat isomerase. Investigation of the reaction mechanism. Z Lebensm Unters-Forsch 165: 140-143
24. Heimann W, Schreier P (1970) The formation of 9-hydroxy-10,12-and 13-hydroxy-9,11-octadecadienoic acid through "lipoperoxidase" of cereals. Helv Chim Acta 53: 2296-2297
25. 2-reducible hemoprotein" in microsomes of pea seeds. J Biol Chem 252: 6118-6124
26. 18 fatty acids in rice plant suffering from rice blast disease. Tetrahedron Lett 26: 2357-2360
27. Kato T, Yamaguchi Y, Hirukawa T, Hoshino N (1991) Structural elucidation of naturally occurring 9,12,13-trihydroxy fatty acids by a synthetic study. Agric Biol Chem 55: 1349-1357
28. Kato T, Yamaguchi Y, Uyehara T, Yokoyama T, Namai T, Yamanaka S (1983) Defense mechanism of the rice plant against rice blast disease. Naturwissenschaften 70: 200-201
29. Masui H, Kondo T, Kojima M (1989) An antifungal compound, 9,12,13-trihydroxy-(E)-10-octadecenoic acid, from Colocasia antiquorum inoculated with Ceratocystis fimbriata. Phytochemistry 28: 2613-2615
30. Matthew JA, Chan HW-S, Galliard T (1977) A simple method for the preparation of pure 9-D-hydroperoxide of linoleic acid and methyl linoleate based on the positional specificity of lipoxygenase in tomato fruit. Lipids 12: 324-326
31. Namai T, Kato T, Yamaguchi Y, Hirukawa T (1993) Anti-rice blast activity and resistance induction of C-18 oxygenated fatty acids. Biosci Biotechnol Biochem 57: 611-613
32. Ohta H, Shida K, Peng Y-L, Furusawa I, Shishiyama J, Aibara S, Monta Y (1991) A lipoxygenase pathway is activated in rice after infection with the rice blast fungus Magnaporthe grisea. Plant Physiol 97: 94-98
33. Salaün J-P, Weissbart D, Helvig C, Durst F, Mioskowski C (1993) Regioselective hydroxylation and epoxidation of lauric acid and unsaturated analogues by cytochrome P450 in Jerusalem artichoke microsomes. Plant Physiol Biochem 31: 285-293
34. Yamamoto H, Tani T (1986) Possible involvement of lipoxygenase in the mechanism of resistance of oats to Puccinia coronata avenae. J Phytopathol 116: 329-337