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. 1974 Jan;138(1):23–31. doi: 10.1042/bj1380023

The enzymic and non-enzymic degradation of colneleic acid, an unsaturated fatty acid ether intermediate in the lipoxygenase pathway of linoleic acid oxidation in potato (Solanum tuberosum) tubers

T Galliard 1, D A Wardale 1, J A Matthew 1
PMCID: PMC1166171  PMID: 4209994

Abstract

Colneleic acid is an unsaturated ether fatty acid derived from linoleic acid via a lipoxygenase-mediated enzyme pathway. It is degraded (a) by an enzyme in potato tubers which is heat-labile and non-dialysable and (b) by a model system containing catalytic amounts of Fe2+ ions. Both enzyme- and Fe2+-catalysed systems have similar properties with respect to pH optima (pH5.0–5.5), oxygen requirement (0.6–0.7 mol of O2 consumed/mol of ether degraded), inhibitors and reaction products. An unstable product breaks down to C8 and C9 carbonyl fragments. Both systems are inhibited by low concentrations of antioxidants (e.g. 5μm-butylated hydroxytoluene) and some chelating agents (e.g. 5μm-diethyldithio-carbamate). The model system is strongly inhibited by metal ions, particularly Cu2+ and Fe3+, at 20μm. Hydrogen peroxide and haemoproteins do not substitute for the enzyme or Fe2+ ions but the non-haem iron protein, ferredoxin, does catalyse the degradation.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. ANSELL G. B., SPANNER S. THE MAGNESIUM-ION-DEPENDENT CLEAVAGE OF THE VINYL ETHER LINKAGE OF BRAIN ETHANOLAMINE PLASMALOGEN. Biochem J. 1965 Jan;94:252–258. doi: 10.1042/bj0940252. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Chan H. W. Soya-bean lipoxygenase: an iron-containing dioxygenase. Biochim Biophys Acta. 1973 Nov 15;327(1):32–35. doi: 10.1016/0005-2744(73)90100-9. [DOI] [PubMed] [Google Scholar]
  3. DOEG K. A., ZIEGLER D. M. Simplified methods for the estimation of iron in mitochondria and submitochondrial fractions. Arch Biochem Biophys. 1962 Apr;97:37–40. doi: 10.1016/0003-9861(62)90041-3. [DOI] [PubMed] [Google Scholar]
  4. Eriksson C. J., Olsson P. A., Svensson S. G. Oxidation of fatty acids by heat treated hemoproteins. Lipids. 1970 Mar;5(3):365–366. doi: 10.1007/BF02531471. [DOI] [PubMed] [Google Scholar]
  5. Galliard T. Enzymic deacylation of lipids in plants. The effects of free fatty acids on the hydrolysis of phospholipids by the lipolytic acyl hydrolase of potato tubers. Eur J Biochem. 1971 Jul 15;21(1):90–98. doi: 10.1111/j.1432-1033.1971.tb01444.x. [DOI] [PubMed] [Google Scholar]
  6. Galliard T., Matthew J. A. Lipids of potato tubers. II. Lipid-degrading enzymes in different varieties of potato tuber. J Sci Food Agric. 1973 May;24(5):623–627. doi: 10.1002/jsfa.2740240516. [DOI] [PubMed] [Google Scholar]
  7. Galliard T., Phillips D. R. Lipoxygenase from potato tubers. Partial purification and properties of an enzyme that specifically oxygenates the 9-position of linoleic acid. Biochem J. 1971 Sep;124(2):431–438. doi: 10.1042/bj1240431. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Galliard T., Phillips D. R. The enzymic conversion of linoleic acid into 9-(nona-1',3'-dienoxy)non-8-enoic acid, a novel unsaturated ether derivative isolated from homogenates of Solanum tuberosum tubers. Biochem J. 1972 Sep;129(3):743–753. doi: 10.1042/bj1290743. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Galliard T. The enzymic deacylation of phospholipids and galactolipids in plants. Purification and properties of a lipolytic acyl-hydrolase from potato tubers. Biochem J. 1971 Feb;121(3):379–390. doi: 10.1042/bj1210379. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Roza M., Francke A. Soyabean lipoxygenase: an iron-containing enzyme. Biochim Biophys Acta. 1973 Nov 15;327(1):24–31. doi: 10.1016/0005-2744(73)90099-5. [DOI] [PubMed] [Google Scholar]
  11. THIELE O. W. [Biocatalytic release of plasmal from plasmalogen. II. Existence and properties of a catalyst in crude phosphatides]. Hoppe Seylers Z Physiol Chem. 1959 Oct 30;316:137–145. doi: 10.1515/bchm2.1959.316.1.137. [DOI] [PubMed] [Google Scholar]
  12. WARNER H. R., LANDS W. E. The metabolism of plasmalogen: enzymatic hydrolysis of the vinyl ether. J Biol Chem. 1961 Sep;236:2404–2409. [PubMed] [Google Scholar]
  13. Yavin E., Gatt S. Oxygen-dependent cleavage of the vinyl -ether linkage of plasmalogens. 2. Identification of the low-molecular-weight active component and the reaction mechanism. Eur J Biochem. 1972 Feb;25(3):437–446. doi: 10.1111/j.1432-1033.1972.tb01713.x. [DOI] [PubMed] [Google Scholar]
  14. Yavin E., Gatt S. Oxygen-dependent cleavage of the vinyl-ether linkage of plasmologens. 1. Cleavage by rat-brain supernatant. Eur J Biochem. 1972 Feb;25(3):431–436. doi: 10.1111/j.1432-1033.1972.tb01712.x. [DOI] [PubMed] [Google Scholar]

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