Abstract
Incubation of linoleic acid with an enzyme preparation from leaves of flax ( Linum usitatissimum L.) led to the formation of a divinyl ether fatty acid, i.e. (9 Z,11 E,1′ Z)-12-(1′-hexenyloxy)-9,11-dodecadienoic [(ω5 Z)-etheroleic] acid, as well as smaller amounts of 13-hydroxy-9( Z),11( E)-octadecadienoic acid. The 13-hydroperoxide of linoleic acid afforded the same set of products, whereas incubations of α-linolenic acid and its 13-hydroperoxide afforded the divinyl ether (9 Z,11 E,1′ Z,3′ Z)-12-(1′,3′-hexadienyloxy)-9,11-dodecadienoic [(ω5 Z)-etherolenic] as the main product. Identification of both divinyl ethers was substantiated by their UV, mass-, 1H NMR and COSY spectral data. In addition to the 13-lipoxygenase and divinyl ether synthase activities demonstrated by these results, flax leaves also contained allene oxide synthase activity as judged by the presence of endogenously formed (15 Z)- cis-12-oxo-10,15-phytodienoic acid in all incubations.
Published Version
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