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- Title
Hexadecanoid pathway in plants: Lipoxygenase dioxygenation of (7 Z,10 Z,13 Z)-hexadecatrienoic acid.
- Authors
Osipova, E. V.; Lantsova, N. V.; Chechetkin, I. R.; Mukhitova, F. K.; Hamberg, M.; Grechkin, A. N.
- 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 (7 S)-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% (11 S)-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.
- Subjects
LIPOXYGENASES; HYPERBARIC oxygenation; SUPEROXIDES; PEA seeds; SOYBEAN
- Publication
Biochemistry (00062979), 2010, Vol 75, Issue 6, p708
- ISSN
0006-2979
- Publication type
Academic Journal
- DOI
10.1134/S0006297910060052