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Part of the book series: Advances in Experimental Medicine and Biology ((AEMB,volume 433))

Abstract

Several oxylipins, including hydroxyoctadecadienoic acids, epoxyoctadecenoic acids, epoxyhydroxyoctadecenoic acids, and trihydroxyoctadecenoic acids, are formed from linoleic acid upon incubation with preparations of cereal seeds. Lipoxygenases1 peroxygenase2, 3 as well as cytochrome P-450’s4 are responsible for these transformations. A pathway in oat seeds for catalytic oxidation of linoleic acid into an anti-fungal trihydroxy acid, 9(S),12(S),13(S)-trihydroxy-10(E)-octadecenoic acid, was recently described5. During this study, the presence in oat seeds of a new hydroxylated derivative of linoleic acid was discovered6. The present paper is a brief account of the structure determination of the new hydroxy acid, for which the trivial name “avenoleic acid” is proposed. In addition, recent data showing that avenoleic acid is mainly localized in the galactolipid fraction of oat seed lipids, and structural studies of the major molecular species of galactolipid containing avenoleic acid, will be described.

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References

  1. H.W. Gardner, Lipoxygenase pathway in cereals, in: Advances in Cereal Science and Technology, Y. Pomeranz, ed., Vol. 9, pp. 161–215. American Association of Cereal Chemists, St. Paul, MN (1988).

    Google Scholar 

  2. M. Hamberg and G. Hamberg, Hydroperoxide-dependent epoxidation of unsaturated fatty acids in the broad bean, Arch. Biochem. Biophys. 283: 409 (1990).

    Article  PubMed  CAS  Google Scholar 

  3. E. Blée and F. Schuber, Efficient epoxidation of unsaturated fatty acids by a hydroperoxide-dependent oxygenase, J. Biol. Chem. 265: 12887 (1990).

    PubMed  Google Scholar 

  4. G.P. Bolwell, K. Bozak, and A. Zimmerlin, Plant cytochrome P450, Phytochemistry 37: 1491 (1994).

    Article  PubMed  CAS  Google Scholar 

  5. M. Hamberg and G. Hamberg, Peroxygenase-catalyzed fatty acid epoxidation in cereal seeds, Plant Physiol. 110: 807 (1996).

    PubMed  CAS  Google Scholar 

  6. M. Hamberg and G. Hamberg, 15(R)-Hydroxylinoleic acid, an oxylipin from oat seeds, Phytochemistry 42: 729 (1996).

    Article  CAS  Google Scholar 

  7. L.-Y. Zhang and M. Hamberg, A gas-liquid chromatographic method for steric analysis of 2-hydroxy, 3-hydroxy, and 2,3-dihydroxy acids, Chem. Phys. Lipids 74: 151 (1994).

    Article  CAS  Google Scholar 

  8. F.D. Gunstone, M. Kates, and J.L. Harwood, Separation and isolation procedures, in: The Lipid Handbook, F.D. Gunstone, J.L. Harwood, and F.B. Padley, eds., 2nd ed., pp. 225–248. Chapman & Hall, London (1994).

    Google Scholar 

  9. W. Fischer, E. Heinz, and M. Zeus, The suitability of lipase from Rhizopus arrhizus delemar for analysis of fatty acid distribution in dihexosyl diglycerides, phospholipids and plant sulfolipids, Hoppe-Seyler’s Z. Physiol. Chem. 354: 1115 (1973).

    Article  PubMed  CAS  Google Scholar 

  10. M. Hamberg, G. Otting, E. Liepinsh, and W. Griffiths, manuscript in preparation.

    Google Scholar 

  11. F.J. van de Loo, P. Broun, S. Turner, and C. Somerville, An oleate 12-hydroxylase from Ricinus communis L. is a fatty acyl desaturase homolog, Proc. Natl. Acad. Sci. USA 92: 6743 (1995).

    Article  PubMed  Google Scholar 

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© 1997 Springer Science+Business Media New York

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Hamberg, M. (1997). Avenoleic Acid: A New Oxylipin from Oat Seeds. In: Sinzinger, H., Samuelsson, B., Vane, J.R., Paoletti, R., Ramwell, P., Wong, P.YK. (eds) Recent Advances in Prostaglandin, Thromboxane, and Leukotriene Research. Advances in Experimental Medicine and Biology, vol 433. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-1810-9_13

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  • DOI: https://doi.org/10.1007/978-1-4899-1810-9_13

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4899-1812-3

  • Online ISBN: 978-1-4899-1810-9

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