Properties and structures of fatty acid hydroperoxide lyase

Belgian Journal of Botany

Volumn 131, Issue 1, 1998, Pages 50-62

  Matsui, Kenji ^a  

^a YAMAGUCHI UNIVERSITY   (Japan)

Author keywords

Fatty acid hydroperoxide lyase; Lipoxygenase; Phytooxylipin; Short chain aldehydes

Indexed keywords

EID: 0032220321     PISSN: 07784031     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (69)

1. ANDRIANARISON R., BENEYTOUT J. & TIXIER M., 1989. - An enzymatic conversion of lipoxygenase products by a hydroperoxide lyase in blue-green algae (Oscillatoria sp.). Plant Physiol. 91 : 1280-1287.
2. AVDIUSHKO S., CROFT K. P. C., BROWN G. C., JACKSON D. M., HAMILTON-KEMP T. R. & HILDEBRAND D., 1995. - Effect of volatile methyl jasmonate on the oxylipin pathway in tabacco, cucumber, and Arabidopsis. Plant Physiol. 109 : 1227-1230.
3. BANAS A., JOHANSSON, I. & STYMNE S., 1992. - Plant microsomal phospholipases exhibit preference for phosphatidylcholine with oxygenated acyl groups. Plant Sci. 84 : 137-144.
4. BELL E. & MULLET J. E., 1993. - Characterization of an Arabidopsis lipoxygenase gene responsive to methyl jasmonate and wounding. Plant Physiol. 103 : 1133-1138.
5. BERGER R. G., KLER A. & DRAWERT F., 1986. - The C6-aldehyde-forming system in Agropyron repens. Biochim. Biophys. Acta, 198 : 12-19.
6. BLEE E., 1996. - Phytooxylipins : The peroxygenase pathway : 138-175. In PIAZZA G. J. (ed.), Lipoxygenase and lipoxygenase pathway enzymes. AOCS Press.
7. BLEE E. & JOYARD J., 1996. - Envelope membranes from spinach chloroplasts are a site of metabolism of fatty acid hydroperoxides. Plant Physiol. 110 : 445-454.
8. CROFT K. P. C., JÜTTNER F. & SLUSARENKO A. J., 1993. - Volatile products of the lipoxygenase pathway evolved from Phaseolus vulgaris (L.) leaves inoculated with Pseudomonas syringae pv phaseolicola. Plant Physiol. 101 : 13-24.
9. FARMER E. E. & RYAN C. A., 1992. - Octadecanoid precursors of jasmonic acid activate the synthesis of wound-inducible proteinase inhibitors. Plant Cell 4: 129-134.
10. GALLIARD T., & PHILLIPS D. R., 1976. - The enzymic cleavage of linoleic acid to C9 carbonyl fragments in extracts of cucumber (Cucumis sativus) fruit and the possible role of lipoxygenase. Biochim. Biophys. Acta 431 : 278-287.
11. GARDNER H. W., 1979. - Lipid hydroperoxide reactivity with proteins and amino acids : A review. J. Agric. Food Chem. 27 : 220-229.
12. GARDNER H. W., 1985. - Flavors and bitter tastes from oxidation of lipids by enzymes : 189-206. In MIN D. B. & SMOUSE T. H. (eds.), Flavor chemistry of fats and oils. AOCS Press.
13. GARDNER H. W., 1991. - Recent investigation into the lipoxygenase pathway of plants. Biochim. Biophys. Acta 1084 : 221-239.
14. GARDNER H. W., DORNBOS D. L. & DESJARDINS A. E., 1990. - Hexanal, trans-2-hexenal, and trans-2-nonecal inhibit soybean, Glycine max, seed germination. J. Agric. Food Chem. 38: 1316-1320.
15. GARDNER H. W. & PLATTNER R. D., 1984. - Linoleate hydroperoxides are cleaved heterolytically into aldehydes by a Lewis acid in aprotic solvent. Lipids 19 : 289-293.
16. GARDNER H. W., WEISLEDER D. & PLATTNER R. D., 1991. - Hydroperoxide lyase and other hydroperoxide-metabolizing activity in tissues of soybean, Glycine max. Plant Physiol. 97 : 1059-1072.
17. GLASGOW W. C., HARRIS T. M. & BRASH A. R., 1986. - A short-chain aldehyde is a major lipoxygenase product in arachidonic acid-stimulated porcine leukocytes. J. Biol. Chem. 261 : 200-204.
18. GLOVER S., DE CARVALHO M. S., BAYBURT T., JONAS M., CHI E., LESLIE C. C., & GELD M. H., 1995. - Translocation of the 85-kda phospholipase a from cytosol to the nuclear envelope in rat basophilic leukemia cells stimulated with calcium ionophore or ige/antigen. J. Biol. Chem. 270 : 15359-15367.
19. GOLLNICK K., & KUHN H. J., 1979. - In WASSERMAN H. H. & MURRAY R. W. (eds), Singlet oxygen : 287-427. Academic Press Inc., New York.
20. HATANAKA A., 1996. - The fresh green odor emitted by plants. Food Rev. Int. 12 : 303-350.
21. HATANAKA A., KAJIWARA T. & MATSUI K., 1988. -Concentration of hydroperoxide lyase activities in root of cucumber seedlings. Z. Naturforsch. 43c : 308-310.
22. HATANAKA A., KAJIWARA T., MATSUI K. & TOYOTA H., 1992. - Substrate specificity of tea leaf hydroperoxide lyase. Z. Naturforsch. 47c : 677-679.
23. HATANAKA A., KAJIWARA T., & SEKIYA J., 1976. -Seasonal variations in trans-2-hexenal and linolenic acid in homogenates of Thea sinensis leaves. Phytochemistry 15 : 1889-1891.
24. HATANAKA A., KAJIWARA T., SEKIYA J. & TOYOTA H., 1986. - Oxygen incorporation in cleavage of 18O-laveled 13-hydroperoxylinoleyl alcohol into 12-hydroxy-(3Z)-dodecenal in tea chloroplasts. Z. Naturforsch. 41c : 359-362.
25. KAJIWARA T, SEKIYA J., ASANO M. & HATANAKA A., 1982. - Enantioselectivitiy of enzymatic cleavage reaction of 13-hydroperoxylinolenic acid to c6-aldehyde and C12-oxo acids in tea chloroplasts. Agric. Biol. Chem. 46 : 3087-3088.
26. KAZENIAC S. J. & HALL R. M., 1970. - J. Food Sci. 35 : 519-.
27. KEMAL C., LOUIS-FLAMBERG P., KRUPINSKI-OLSEN R. & SHORTER A. L., 1987. - Reductive inactivation of soybean lipoxygenase 1 by catechols : a possible mechanism for regulation of lipoxygenase activity. Biochemistry 26 : 7064-7072.
28. KIM I. & GROSCH W., 1981. - Partial purification and properties of a hydroperoxide lyase from fruits of pear. J. Agric. Food Chem. 29 : 1220-1225.
29. KONDO Y., HASHIDOKO Y., MIZUTANI J., 1995. - An enzymatic formation of 13-oxo-trideca-9,11-dienoic acid from 13-hydroperoxylinolenic acid by a homolytic hydroperoxide lyase in elicitor-treated soybean cotyldeons. Biochim. Biophys. Acta 1255 : 9-15.
30. LAUDERT D., PFANNSCHMIDT U., LOTTSPEICH F., HOLLÄNDER-CZYTKO, H. & WEILER E. W., 1996. - Cloning, molecular and functional characterization of Arabidopsis thaliana allene oxide synthase (CYP74), the first enzyme of the octadecanoid pathway to jasmonates. Plant Mol. Biol. 31 : 323-335.
31. MAJOR R. T., MARCHINI P. & SPROSTON T., 1960. - Isolation from Ginkgo biloba L. of an inhibitor of fungus growth. J. Biol. Chem. 235 : 3298-3299.
32. MATSUI K., SHIBATA Y., KAJIWARA T. & HATANAKA A., 1989. - Separation of 13-and 9-hydroperoxide lyase activities in cotyledons of cucumber seedlings. Z. Naturforsch. 44c : 883-885.
33. MATSUI K., TOYOTA H., KAJIWARA T., KAKUNO T. & HATANAKA A., 1991. - Fatty acid hydroperoxide cleaving enzyme, hydroperoxide lyase, from tea leaves. Phytochemistry, 30 : 2109-2113.
34. MATSUI K., KAJIWARA T. & HATANAKA A., 1992. -Inactivation of tea leaf hydroperoxide lyase by fatty acid hydroperoxide. J. Agric. Food Chem. 40 : 175-178.
35. MATSUI K., KAJI Y., KAJIWARA T. & HATANAKA A., 1995. - Developmental changes of lipoxygenase and fatty acid hydroperoxide lyase activities in cultured cells of Marchantia polymorpha. Phytochemistry 41 : 177-182.
36. MATSUI K., SHIBUTANI M., HASE T. & KAJIWARA T., 1996. - Bell pepper fruit fatty acid hydroperoxide lyase is a cytochrome P450. FEBS Lett. 394 : 21-24.
37. MATSUI K., SHIBATA Y., TATEBA H., HATANAKA A. & KAJIWARA T., 1997. - Changes of lipoxygenase and fatty acid hydroperoxide lyase activities in bell pepper fruits during maturation. Biosci. Biotech. Biochem. 61 : 199-201.
38. MATTHEW J. A. & GALLIARD T., 1978. - Enzymic formation of carbonyls from linoeic acid in leaves of Phaseolus vulgaris. Phytochemistry 17 : 1043-1044.
39. MAU J., BEELMAN R. B. & ZIEGLER G. R., 1992. -Effect of 10-oxo-trans-8-decenoic acid on growth of Agaricus bisporus. Phytochemistry 31 : 4059-4064.
40. OLÎAS M. J., RIOS J., VALLE M., ZAMORA R., SANZ L. C. & AXELROD B., 1990. - Fatty acid hydropeoxide lyase in germinating soybean seedlings. J. Agric. Food Chem. 38 : 624-630.
41. PENG Y., SHIRANO Y., OHTA H., HIBINO T., TANAKA K. & SHIBATA D., 1994. - A novel lipoxygenase from rice. J. Biol. Chem. 269 : 3755-3761.
42. RÖSE U. S. R., MANUKIAN A., HEATH R. R. & TUMLINSON J. H., 1996. - Volatile semiochemicals released from undamaged cotton leaves. Plant Physiol. 111 : 487-495.
43. SAKAKI T., SAITO K., KAWAGUCHI A., KONDO N. & YAMADA M., 1990. - Conversion of monogalactosyldiacylglycerols to triacylglycerols in ozone-fumigated spinach leaves. Plant Physiol. 94 : 766-772.
44. SALCH Y. P., GROVE M. J., TAKAMURA H. & GARDNER H. W., 1995. - Characterization of a C-5,13-cleaving enzyme of 13(S)-hydroperoxide of linolenic acid by soybean seed. Plant Physiol. 108: 1211-1218.
45. SEKIYA J., KAJIWARA T. & HATANAKA A., 1978. -Effects of inhibitors on the enzyme system producing C6-aldehydes from C18-unsaturated fatty acids in chloroplasts of Japanese silver (Farfugium japonicum) leaves. Plant Cell Physiol. 19 : 553-559.
46. SEKIYA J., KAMIUCHI H. & HATANAKA A., 1982. -Lipoxygenase, hydroperoxide lyase and volatile C6-aldehyde formation from C18-fatty acids during development of Phaseolus vulgaris L. Plant Cell Physiol. 23 : 631-638.
47. SHIBATA D., 1996. - Plant lipoxygenase genes : 39-55. In PIAZZA G. J. (ed.), Lipoxygenase and lipoxygenase pathway enzymes. AOCS Press.
48. SHIBATA Y., MATSUI K., KAJIWARA T. & HATANAKA A., 1995a. - Purification and properties of fatty acid hydroperoxide lyase from green bell pepper fruits. Plant Cell Physiol. 36 : 147-156.
49. SHIBATA Y., MATSUI K., KAJIWARA T. & HATANAKA A., 1995b. - Fatty acid hydroperoxide lyase is a heme protein. Biochem. Biophys. Res. Commun. 207 : 438-443.
50. SIEDOW J. N., 1991. - Plant lipoxygenase : Structure and function. Ann. Rev. Plant Physiol. Plant Mol. Biol. 42 : 145-188.
51. SLOANE D. L., 1996. - Exploring the structure and function of mammalian lipoxygenases by site-directed mutagenesis : 57-79. In PIAZZA G. J. (ed.), Lipoxygenase and lipoxygenase pathway enzymes. AOCS Press.
52. SLUSARENKO A. J., 1996. - The role of lipoxygenase in plant resistance to infection : 176-197. In PIAZZA G. J. (ed.), Lipoxygenase and lipoxygenase pathway enzymes. AOCS Press.
53. SONG W., FUNK C. D. & BRASH A., 1993. - 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.
54. STRONG F. E. & KRUITWAGEN E., 1967. - Traumatic acid : an accelerator of abscission in cotton explants. Nature 215 : 1380-1381.
55. TAKABAYASHI J. & DICKE M., 1996. - Plant-carnivore mutualism through herbivore-induced carnivore attractants. Trend Plant Sci. 1: 109-113.
56. TRESHOW M., 1955. - Physiology and anatomical development of tomate fruit tumore. Am. J. Bot. 42 : 198-202.
57. TURLINGS T. C. J., TUMILNSON J. H. & LEWIS W. J., 1990. - Exploitation of herbivore-induced plant odors by host-seeking parasitic wasps. Science 250: 1251-1253.
58. VAZ A. D. N. & COON M. J., 1987. - Hydrocarbon formation in the reductive cleavage of hydroperoxides by cytochrome P-450. Proc. Natl. Acad. Sci. USA 84 : 1172-1176.
59. VICK B. A. & ZIMMERMAN D. C., 1976. - Lipoxygenase and hydroperoxide lyase in germinating watermelon seedlings. Plant Physiol. 57 : 780-788.
60. VICK B. A. & ZIMMERMAN D. C., 1987. - Pathways of fatty acid hydroperoxide metabolism in spinach leaf chloroplasts. Plant Physiol. 85 : 1073-1078.
61. VICK B. A. & ZIMMERMAN D. C., 1989. - Metabolism of fatty acid hydroperoxides by Chlorella pyrenoidosa. Plant Physiol. 90 : 125-132.
62. WARDALE D. A., LAMBERT E. A. & GALLIARD T., 1978. - Localization of fatty acid hydroperoxide cleavage activity in membranes of cucumber fruit. Phytochemistry 17 : 205-212.
63. WURZENBERGER M. & GROSCH W., 1984a. - Origin of the oxygen in the products of the enzymatic cleavage reaction of linoleic acid to 1-octen-3-ol and 10-oxo-trans-8-decenoic acid in mushrooms (Psalliota bispora). Biochim. Biophys. Acta 794 : 18-24.
64. WURZENBERGER M. & GROSCH W., 1984b. - The formation of 1-octene-3-ol from the 10-hydroperoxide isomer of linoleic acid by a hydroperoxide lyase in mushrooms (Psalliota bispora). Biochim. Biophys. Acta 794 : 25-30.
65. WURZENBERGER M. & GROSCH W., 1986. - Enzymic oxidation of linolenic acid to 1,Z-5-octadien-3-ol, Z-2,Z-5-octadien-1-ol and 10-oxo-E-8-decenoic acid by a protein fraction from mushrooms (Psalliota bispora). Lipids 21 : 262-266.
66. YANO M., OKADA K., KUBOTA K. & KOBAYASHI A., 1990. - Studies on the precursors of monoterpene alcohols in tea leaves. Agric. Biol. Chem. 54 : 1023-1028.
67. ZERINGUE H. J., 1992. - Effects of C6-C10 alkenals and alkanals on eliciting a defence response in the developing cotton boll. Phytochemistry 31 : 2305-2308.
68. ZHUANG H., HAMILTON-KEMP T. R., ANDERSE R. A. & HILDEBRAND D. F., 1992. - Developmental change in C6-aldehyde formation by soybean leaves. Plant Physiol. 100 : 80-87.
69. ZIMMERMAN D. C. & COUDRON C. A., 1979. -Identification of traumatin, a wound hormone, as 12-oxo-trans-10-dodecenoic acid. Plant Physiol. 63 : 536-541.