Abstract
The potato tuber lipoxygenase preparations convert α-linolenic acid not only to 9(S)-HPOTE, but also to some more polar metabolites. Two of these polar products, I and II, with ultraviolet absorbance maxima at 267 nm were purified by HPLC. It was found that metabolites I and II have, respectively, one and two hydroperoxy groups. Products of NaBH 4 reduction of both I and II were identified by their chemical ionization and electron impact mass spectra and by 1H-NMR spectra as 9,16-dihydroxy-10( E), 12( Z), 14( E)-octadecatrienoic acid. The obtained results suggest that compound II is 9,16-dihydroperoxy-10( E), 12( Z), 14( E)-octadecatrienoic acid and product I is a mixture of two positional isomers, 9-hydroxy-16-hydroperoxy-10( E),12( Z),14( E)-octadecatrienoic and 9-hydroperoxy-16-hydroxy-10( E),12( Z), 14( E)-octadecatrienoic acids. Lipoxygenase converts efficiently [ 14C]9-HOTE into product I. Also, both metabolites I and II are the products of double dioxygenation. The second oxygenation at C-16 position as well as the first one at C-9 is controlled by lipoxygenase.
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