Avenoleic acid: a new oxylipin from oat seeds.

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.