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Hexadecanoid pathway in plants: Lipoxygenase dioxygenation of (7Z,10Z,13Z)-hexadecatrienoic acid

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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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Abbreviations

CP-HPLC:

chiral phase HPLC

GC-MS:

gas chromatography-mass spectrometry

GmLOX-1:

soybean lipoxygenase-1

GmLOX-2:

soybean lipoxygenase-2

7-H(P)HT:

(8E,10Z,13Z)-7-hydro(pero)xy-8,10,13-hexadecatrienoic acid

H(P)HT:

hydro(pero)xyhexadecatrienoic acid

H(P)OD:

hydro(pero)xide of linoleic acid

H(P)OT:

hydro(pero)xide of α-linolenic acid

NP-HPLC:

normal phase HPLC

ZmLOX:

maize 9-lipoxygenase

16:3:

(7Z,10Z,13Z)-7,10,13-hexadecatrienoic acid

18:3:

α-linolenic acid

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Authors and Affiliations

  1. Kazan Institute of Biochemistry and Biophysics, Kazan Research Center, Russian Academy of Sciences, ul. Lobachevskogo 2/31, 420111, Kazan, Russia

    E. V. Osipova, N. V. Lantsova, I. R. Chechetkin, F. K. Mukhitova & A. N. Grechkin

  2. Department of Medical Biochemistry and Biophysics, Division of Physiological Chemistry II, Karolinska Institutet, SE 171 77, Stockholm, Sweden

    M. Hamberg

Authors
  1. E. V. Osipova
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  2. N. V. Lantsova
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  3. I. R. Chechetkin
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  4. F. K. Mukhitova
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  5. M. Hamberg
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  6. A. N. Grechkin
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Corresponding author

Correspondence to A. N. Grechkin.

Additional information

Published in Russian in Biokhimiya, 2010, Vol. 75, No. 6, pp. 796–806.

Originally published in Biochemistry (Moscow) On-Line Papers in Press, as Manuscript BM09-370, March 28, 2010.

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Osipova, E.V., Lantsova, N.V., Chechetkin, I.R. et al. Hexadecanoid pathway in plants: Lipoxygenase dioxygenation of (7Z,10Z,13Z)-hexadecatrienoic acid. Biochemistry Moscow 75, 708–716 (2010). https://doi.org/10.1134/S0006297910060052

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  • DOI: https://doi.org/10.1134/S0006297910060052

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