Discovery of α-Linolenic Acid 16( S )-Lipoxygenase: Cucumber ( Cucumis sativus L.) Vegetative Lipoxygenase 3.

Autor: Gorina SS; Kazan Institute of Biochemistry and Biophysics, FRC Kazan Scientific Center of RAS, P.O. Box 261, 420111 Kazan, Russia., Egorova AM; Kazan Institute of Biochemistry and Biophysics, FRC Kazan Scientific Center of RAS, P.O. Box 261, 420111 Kazan, Russia., Lantsova NV; Kazan Institute of Biochemistry and Biophysics, FRC Kazan Scientific Center of RAS, P.O. Box 261, 420111 Kazan, Russia., Toporkova YY; Kazan Institute of Biochemistry and Biophysics, FRC Kazan Scientific Center of RAS, P.O. Box 261, 420111 Kazan, Russia., Grechkin AN; Kazan Institute of Biochemistry and Biophysics, FRC Kazan Scientific Center of RAS, P.O. Box 261, 420111 Kazan, Russia.
Jazyk: angličtina
Zdroj: International journal of molecular sciences [Int J Mol Sci] 2023 Aug 19; Vol. 24 (16). Date of Electronic Publication: 2023 Aug 19.
DOI: 10.3390/ijms241612977
Abstrakt: The GC-MS profiling of the endogenous oxylipins (Me/TMS) from cucumber ( Cucumis sativus L.) leaves, flowers, and fruit peels revealed a remarkable abundance of 16-hydroxy-9,12,14-octadecatrienoic acid (16-HOT). Incubations of homogenates from these organs with α-linolenic acid yielded 16( S )-hydroperoxide (16-HPOT) as a predominant product. Targeted proteomic analyses of these tissues revealed the presence of several highly homologous isoforms of the putative "9 S -lipoxygenase type 6". One of these isoenzymes (CsLOX3, an 877 amino acid polypeptide) was prepared by heterologous expression in E. coli and exhibited 16( S )- and 13( S )-lipoxygenase activity toward α-linolenic and linoleic acids, respectively. Furthermore, α-linolenate was a preferred substrate. The molecular structures of 16( S )-HOT and 16( S )-HPOT (Me or Me/TMS) were unequivocally confirmed by the mass spectral data, 1 H-NMR, 2D 1 H- 1 H-COSY, TOCSY, HMBC, and HSQC spectra, as well as enantiomeric HPLC analyses. Thus, the vegetative CsLOX3, biosynthesizing 16( S )-HPOT, is the first 16( S )-LOX and ω3-LOX ever discovered. Eicosapentaenoic and hexadecatrienoic acids were also specifically transformed to the corresponding ω3( S )-hydroperoxides by CsLOX3.
Databáze: MEDLINE
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