Hexadecanoid pathway in plants: Lipoxygenase dioxygenation of (7<Emphasis Type="Italic">Z</Emphasis>,10<Emphasis Type="Italic">Z</Emphasis>,13<Emphasis Type="Italic">Z</Emphasis>)-hexadecatrienoic acid |
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Authors: | E V Osipova N V Lantsova I R Chechetkin F K Mukhitova M Hamberg A N Grechkin |
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Institution: | (1) Kazan Institute of Biochemistry and Biophysics, Kazan Research Center, Russian Academy of Sciences, ul. Lobachevskogo 2/31, 420111 Kazan, Russia;(2) Department of Medical Biochemistry and Biophysics, Division of Physiological Chemistry II, Karolinska Institutet, SE 171 77 Stockholm, Sweden; |
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Abstract: | 7,10,13-Hexadecatrienoic acid (16:3) is abundant in many plant species. However, its metabolism through the lipoxygenase pathway
is not sufficiently understood. The goal of present work was to investigate the oxygenation of 16:3 by different plant lipoxygenases
and to study the occurrence of oxygenated derivatives of 16:3 in plant seedlings. The recombinant maize 9-lipoxygenase specifically
converted 16:3 into (7S)-hydroperoxide. Identification of this novel oxylipin was substantiated by data of GC-MS, LC-MS/MS, 1H-NMR, and 2D-COSY as well as by deuterium labeling from 2H6]16:3. Soybean lipoxygenase 1 produced 91% (11S)-hydroperoxide and 6% racemic 14-hydroperoxide. Recombinant soybean lipoxygenase 2 (specifically oxidizing linoleate into
13-hydroperoxide) lacked any specificity towards 16:3. Lipoxygenase 2 produced 7-, 8-, 10-, 11-, 13-, and 14-hydroperoxides
of 16:3, as well as a significant amount of bis-allylic 9-hydroperoxide. Seedlings of several examined plant species possessed
free hydroxy derivatives of 16:3 (HHTs), as well as their ethyl esters. Interestingly, HHTs occur not only in “16:3 plants”,
but also in typical “18:3 plants” like pea and soybean seedlings. |
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