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J Biol Chem, Vol. 273, Issue 49, 32650-32655, December 4, 1998

Evidence for the Formation of Dinor Isoprostanes E₁ from -Linolenic Acid in Plants

From the Institute of Pharmaceutical Biology, University of Munich, Karlstrae 29, D-80333 Munich, Germany

The free radical oxidation of arachidonic acid is known to generate complex metabolites, termed isoprostanes, that share structural features of prostaglandins and exert potent receptor-mediated biological activities. In the present study, we show that -linolenic acid can undergo a similar oxidation process, resulting in a series of isomeric dinor isoprostanes E₁. E-ring dinor isoprostane formation from linolenate was found to be catalyzed by soybean lipoxygenase. The main enzymatic products were 13- and 9-hydroperoxylinolenate but in addition, two dinor isoprostane E₁ regioisomers were formed with a yield of 0.31%.

Identification and quantification of two dinor isoprostane E₁ regioisomers in plant cell cultures was achieved by a negative chemical ionization gas chromatography-mass spectrometry method using [¹⁸O]dinor isoprostanes E₁ as internal standards. Endogenous levels of these compounds were determined in four taxonomically distant plant species and found to be in the range of 4.5 to 60.9 ng/g of dry weight.

Thus analogous pathways in animals and plants exist, each leading to a family of prostaglandin-like compounds derived from polyunsaturated fatty acids. It remains to be shown whether the dinor isoprostanes exert biological activities in plants as has been demonstrated for their C20 congeners in mammals.

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