Intermediates and products formed during fatty acid α-oxidation in cucumber (Cucumis sativus)

Lipids

Volumn 34, Issue 7, 1999, Pages 661-673

  Andersen Borge, Grethe I ^a,b   Vogt, Gjermund ^a   Nilsson, Astrid ^a  

^a NORWEGIAN FOOD RESEARCH INSTITUTE   (Norway)

^b NORWEGIAN UNIVERSITY OF LIFE SCIENCES   (Norway)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXOGLUTARIC ACID; ASCORBIC ACID; FATTY ACID; FORMIC ACID; HYDROGEN PEROXIDE; PALMITIC ACID DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE;

ARTICLE; CELL FRACTIONATION; CENTRIFUGATION; CONCENTRATION RESPONSE; CUCUMBER; ENZYME ACTIVITY; ENZYME PURIFICATION; FATTY ACID OXIDATION; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN;

ACYL COENZYME A; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CUCUMIS SATIVUS; FATTY ACIDS; HYDROGEN PEROXIDE; OXIDATION-REDUCTION; SUBCELLULAR FRACTIONS;

CUCUMIS SATIVUS; MAMMALIA;

EID: 13044285438     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11745-999-0411-7     Document Type: Article

References (49)

1. Laties, G.G., and Hoelle, C. (1967) The α-Oxidation of Long-Chain Fatty Acids as a Possible Component of the Basal Respiration of Potato Slices, Phytochemistry 6, 49-57.
2. Fleming, H.P., Cobb, W.Y., Etchells, J.L., and Bell, T.A. (1968) The Formation of Carbonyl Compounds in Cucumbers, J. Food Sci. 33, 527-576.
3. Laties, G.G., Hoelle, C., and Jacobson, B.S. (1972) α-Oxidation of Endogenous Fatty Acids in Fresh Potato Slices, Phytochemistry 11, 3403-3411.
4. Galliard, T. (1980) Degradation of Acyl Lipids: Hydrolytic and Oxidative Enzymes, in Lipids: Structure and Function (Stumpf, P.K., ed.) pp. 85-116, Academic Press, New York.
5. Baardseth, P., Slinde, E., and Thomassen, M.S. (1987) Studies on Fatty Acid α-Oxidation in Cucumber, Biochim. Biophys. Acta 922, 170-176.
6. Borge, G.I.A., Slinde, E., and Nilsson, A. (1997) Long-Chain Saturated Fatty Acids Can Be α-Oxidised by a Purified Enzyme (M(r) 240,000) in Cucumber (Cucumis sativus), Biochim. Biophys. Acta 1344, 47-58.
7. Gerhardt, B. (1992) Fatty Acid Degradation in Plants, Prog. Lipid Res. 31, 417-446.
8. Newcomb, E.H., and Stumpf, P.K. (1952) Fatty Acid Synthesis and Oxidation in Peanut Cotyledons, in Phosphorus Metabolism (McElroy, W.D., and Glass, B., eds.) pp. 291-300, The Johns Hopkins Press, Baltimore.
9. Martin, R.O., and Stumpf, P.K. (1959) Fat Metabolism in Higher Plants, α-Oxidation of Long Chain Fatty Acids, J. Biol. Chem. 234, 2548-2554.
10. Hitchcock, C., and James, A.T. (1966) The Mechanism of α-Oxidation in Leaves, Biochim. Biophys. Acta 116, 413-424.
11. Hitchcock, C., and James, A.T. (1964) Oxidation of Unsaturated Fatty Acids by Leaf Tissue, J. Lipid Res. 5, 593-599.
12. Hitchcock, C., and Rose, A. (1971) The Stereochemistry of α-Oxidation of Fatty Acids in Plants: The Configuration of Biosynthetic Long-Chain 2-Hydroxy Acids, Biochem. J. 125, 1155-1156.
13. Shine, W.E., and Stumpf, P.K. (1974) Fat Metabolism in Higher Plants. Recent Studies on Plant α-Oxidation Systems, Arch. Biochem. Biophys. 162, 147-157.
14. Galliard, T., and Matthew, J.A. (1976) The Enzymic Formation of Long-Chain Aldehydes and Alcohols by α-Oxidation of Fatty Acids in Extracts of Cucumber Fruit (Cucumis sativus), Biochim. Biophys. Acta 424, 26-35.
15. Kajiwara, T., Yoshikawa, H., Saruwatari, T., Hatanaka, A., Kawai, T., Ishihara, M., and Tsuneya, Y. (1988) Enzymatic Formation of Unsaturated Long-Chain Fatty Aldehydes in Ulva pertusa, Phytochemistry 27, 1643-1645.
16. Kajiwara, T., Matsui, K., and Akakabe, Y. (1996) Biogeneration of Volatile Compounds via Oxylipins in Edible Seaweeds, in Biotechnology for Improved Foods and Flavors (Takeoka, G.R., Teranishi, R., Williams, P.J., and Kobayashi, A., eds.) pp. 146-166, American Chemical Society, Washington, DC.
17. Matsunaga, I., Yamada, M., Kusunose, E., Nishiuchi, Y., Yano, L, and Ichihara, K. (1996) Direct Involvement of Hydrogen Peroxide in Bacterial α-Hydroxylation of Fatty Acid, FEBS Lett. 386, 252-254.
18. Matsunaga, I., Yokotani, N., Gotoh, O., Kusunose, E., Yamada, M., and Ichihara, K. (1997) Molecular Cloning and Expression of Fatty Acid α-Hydroxylase from Sphingomonas paucimobilis, J. Biol. Chem. 272, 23592-23596.
19. Steinberg, D. (1989) Refsum Disease, in The Metabolic Basis of Inherited Disease (Scriver, C.R., Beaudet, A.L., Sly, W.S., and Valle, D., eds.) pp. 1533-1550, McGraw-Hill, New York.
20. Watkins, P.A., Howard, A.E., and Mihalik, S.J. (1994) Phytanic Acid Must Be Activated to Phytanoyl-CoA Prior to Its α-Oxidation in Rat Liver Peroxisomes, Biochim. Biophys. Acta 1214, 288-294.
21. Mihalik, S.J., Rainville, A.M., and Watkins, P.A. (1995) Phytanic Acid α-Oxidation in Rat Liver Peroxisomes. Production of α-Hydroxyphytanoyl-CoA and Formate Is Enhanced by Dioxygenase Cofactors, Eur. J. Biochem. 232, 545-551.
22. 2, Cofactor Requirements, Subcellular Localization and Formation of a 2-Hydroxy-3-methylacyl-CoA Intermediate, Eur. J. Biochem. 240, 674-683.
23. Jansen, G.A., Mihalik, S.J., Watkins, P.A., Moser, H.W., Jakobs, C. Denis, S., and Wanders, R.J. (1996) Phytanoyl-CoA Hydroxylase Is Present in Human Liver, Located in Peroxisomes, and Deficient in Zellweger Syndrome: Direct, Unequivocal Evidence for the New, Revised Pathway of Phytanic Acid α-Oxidation in Humans, Biochem. Biophys. Res. Commun. 229, 205-210.
24. Casteels, M., Croes, K., Van Veldhoven, P.P., and Mannaerts, G.P. (1997) Peroxisomal Localization of α-Oxidation in Human Liver, J. Inherit. Metab. Dis. 20, 665-673.
25. Mihalik, S.J., Morrell, J.C., Kim, D., Sacksteder, K.A., Watkins, P.A., and Gould, S.J. (1997) Identification of PAHX, a Refsum Disease Gene, Nature Genet. 17, 185-189.
26. Jansen, G.A., Ofman, R., Ferdinandusse, S., Ijlst, L., Muijsers, A.O., Skjeldal, O.H., Stokke, O., Jakobs, C., Besley, G.T., Wraith, J.E., and Wanders, R.J. (1997) Refsum Disease Is Caused by Mutations in the Phytanoyl-CoA Hydroxylase Gene, Nature Genet. 17, 190-193.
27. Poulos, A., Sharp, P., Singh, H., Johnson, D.W., Carey, W.F., and Easton, C. (1993) Formic Acid Is a Product of the α-Oxidation of Fatty Acids by Human Skin Fibroblasts: Deficiency of Formic Acid Production in Peroxisome-Deficient Fibroblasts, Biochem. J. 292, 457-461.
28. Casteels, M., Croes, K., Van Veldhoven, P.P., and Mannaerts, G.P. (1994) Aminotriazole Is a Potent Inhibitor of α-Oxidation of 3-Methyl-Substituted Fatty Acids in Rat Liver, Biochem. Pharmacol. 48, 1973-1975.
29. Croes, K., Van Veldhoven, P.P., Mannaerts, G.P., and Casteels, M. (1997) Production of Formyl-CoA During Peroxisomal α-Oxidation of 3-Methyl-Branched Fatty Acids, FEBS Lett. 407, 197-200.
30. Verhoeven, N.M., Schor, D.S., ten Brink, H.J., Wanders, R.J., and Jakobs, C. (1997) Resolution of the Phytanic Acid α-Oxidation Pathway: Identification of Pristanal as Product of the Decarboxylation of 2-Hydroxyphytanoyl-CoA, Biochem. Biophys. Res. Commun. 237, 33-36.
31. Croes, K., Casteels, M., Asselberghs, S., Herdewijn, P., Mannaerts, G.P., and Van Veldhoven, P.P. (1997) Formation of a 2-Methyl-Branched Fatty Aldehyde During Peroxisomal α-Oxidation, FEBS Lett. 412, 643-645.
32. Harwood, L.M., and Moody, C.F. (1989) Experimental Organic Chemistry. Principles and Practice, pp. 520-522, Blackwell Scientific Publications, Great Britain.
33. Smith, P.K., Krohn, R.I., Hermanson, G.T., Mallia, A.K., Gartner, F.H., Provenzano, M.D., Fujimoto, E.K., Goeke, N.M., OLson, B.J., and Klenk, D.C. (1985) Measurement of Protein Using Bicinchoninic Acid, Anal. Biochem. 150, 76-85.
34. 14C-Formic Acid, Anal. Biochem. 32, 519-520.
35. 3+ and Phosphate, Lipids 29, 671-678.
36. Wanders, R.J., van Roermund, C.W., Schor, D.S., ten Brink, H.J., and Jakobs, C. (1994) 2-Hydroxyphytanic Acid Oxidase Activity in Rat and Human Liver and Its Deficiency in the Zellweger Syndrome, Biochim. Biophys. Acta 1227, 177-182.
37. Castelfranco, P., Stumpf, P.K., and Contopoulou, R. (1955) Fat Metabolism in Higher Plants. A Soluble Palmitate Oxidase Requiring Glycolic Acid as Activator, J. Biol. Chem. 214, 567-577.
38. Salim-Hanna, M., Campa, A., and Cilento, G. (1989) α-Oxidation of α-Hydroxyfatty Acids in Rat Brain. Possible Involvement of an α-Peroxylactone, Lipids 24, 750-752.
39. Adam, W., Boland, W., Hartmann-Schreier, J., Humpf, H.-U., Lazarus, M., Saffert, A., Saha-Möller, C.R., and Schreier, P. (1998) α-Hydroxylation of Carboxylic Acids with Molecular Oxygen Catalyzed by the α-Oxidase of Peas (Pisum sativum): A Novel Biocatalytic Synthesis of Enantiomerically Pure (R)-2-Hydroxy Acids, J. Am. Chem. Soc. 120, 11044-11048.
40. Akakabe, Y., Matsui, K., and Kajiwara, T. (1999) Enantioselective α-Hydroperoxylation of Long-Chain Fatty Acids with Grade Enzyme of Marine Green Alga Ulva pertusa, Tetrahedron Lett. 40, 137-1140.
41. Tsai, S.C., Herndon, J.H., Jr., Uhlendorf, B.W., Fales, H.M., and Mize, C.E. (1967) The Formation of α-Hydroxy Phytanic Acid from Phytanic Acid in Mammalian Tissues, Biochem. Biophys. Res. Commun. 28, 571-577.
42. Skjeldal, O.H., and Stokke, O. (1988) Evidence Against Alpha-Hydroxyphytanic Acid as an Intermediate in the Metabolism of Phytanic Acid, Scand. J. Clin. Lab. Invest. 48, 97-102.
43. Verhoeven, N.M., Schor, D.S., Previs, S.F., Brunengraber, H., and Jakobs, C. (1997) Stable Isotope Studies of Phytanic Acid α-Oxidation: In Vivo Production of Formic Acid, Eur. J. Pediatr. 156 Suppl. 1, S83-87.
44. Mize, C.E., Steinberg, D., Avigan, J., and Fales, H.M. (1966) A Pathway for Oxidative Degradation of Phytanic Acid in Mammals, Biochem. Biophys. Res. Commun. 25, 359-365.
45. Hutton, D., and Steinberg, D. (1973) Identification of Propionate as a Degradation Product of Phytanic Acid Oxidation in Rat and Human Tissues, J. Biol. Chem. 248, 6871-6875.
46. Muralidharan, F.N., and Muralidharan, V.B. (1987) Phytanic Acid Alpha Oxidation in Rat Liver: Studies on Alpha Hydroxylation, Int. J. Biochem. 19, 663-670.
47. Huang, S., Van Veldhoven, P.P., Vanhoutte, F., Parmentier, G., Eyssen, H.J., and Mannaerts, G.P. (1992) α-Oxidation of 3-Methyl-Substituted Fatty Acids in Rat Liver, Arch. Biochem. Biophys. 296, 214-223.
48. Pahan, K., Khan, M., Smith, B.T., and Singh, I. (1995) Ketoconazole and Other Imidazole Derivatives Are Potent Inhibitors of Peroxisomal Phytanic Acid α-Oxidation, FEBS Lett. 377, 213-216.
49. Egomond, M.R., Finazzi-Agro, A., Fasella, P.M., Veldink, G.A., and Vliegenthart, J.F. (1975) Changes in the Fluorescence and Absorbance of Lipoxygenase-1 Induced by 13-Ls-Hydroperoxylinoleic Acid and Linoleic Acid, Biochim. Biophys. Acta 397, 43-49.