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

Gorina, Svetlana S.; Egorova, Alevtina M.; Lantsova, Natalia V.; Toporkova, Yana Y.; Grechkin, Alexander N.

doi:10.3390/ijms241612977

Open AccessArticle

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

by

Svetlana S. Gorina

^*,

Alevtina M. Egorova

,

Natalia V. Lantsova

,

Yana Y. Toporkova

and

Alexander N. Grechkin

^*

Kazan Institute of Biochemistry and Biophysics, FRC Kazan Scientific Center of RAS, P.O. Box 261, 420111 Kazan, Russia

^*

Authors to whom correspondence should be addressed.

Int. J. Mol. Sci. 2023, 24(16), 12977; https://doi.org/10.3390/ijms241612977

Submission received: 19 July 2023 / Revised: 14 August 2023 / Accepted: 16 August 2023 / Published: 19 August 2023

(This article belongs to the Section Biochemistry)

Download

Browse Figures

Versions Notes

Abstract

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 “9S-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, ¹H-NMR, 2D ¹H-¹H-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.

Keywords: lipoxygenase; molecular cloning; ω3 fatty acids; ω3(S) dioxygenation; fatty acid hydroperoxides; cucumber (Cucumis sativus L.)

Share and Cite

MDPI and ACS Style

Gorina, S.S.; Egorova, A.M.; Lantsova, N.V.; Toporkova, Y.Y.; Grechkin, A.N. Discovery of α-Linolenic Acid 16(S)-Lipoxygenase: Cucumber (Cucumis sativus L.) Vegetative Lipoxygenase 3. Int. J. Mol. Sci. 2023, 24, 12977. https://doi.org/10.3390/ijms241612977

AMA Style

Gorina SS, Egorova AM, Lantsova NV, Toporkova YY, Grechkin AN. Discovery of α-Linolenic Acid 16(S)-Lipoxygenase: Cucumber (Cucumis sativus L.) Vegetative Lipoxygenase 3. International Journal of Molecular Sciences. 2023; 24(16):12977. https://doi.org/10.3390/ijms241612977

Chicago/Turabian Style

Gorina, Svetlana S., Alevtina M. Egorova, Natalia V. Lantsova, Yana Y. Toporkova, and Alexander N. Grechkin. 2023. "Discovery of α-Linolenic Acid 16(S)-Lipoxygenase: Cucumber (Cucumis sativus L.) Vegetative Lipoxygenase 3" International Journal of Molecular Sciences 24, no. 16: 12977. https://doi.org/10.3390/ijms241612977

APA Style

Gorina, S. S., Egorova, A. M., Lantsova, N. V., Toporkova, Y. Y., & Grechkin, A. N. (2023). Discovery of α-Linolenic Acid 16(S)-Lipoxygenase: Cucumber (Cucumis sativus L.) Vegetative Lipoxygenase 3. International Journal of Molecular Sciences, 24(16), 12977. https://doi.org/10.3390/ijms241612977

Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here.

Article Menu

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

Abstract

Share and Cite

Article Metrics

Article Access Statistics

Further Information

Guidelines

MDPI Initiatives

Follow MDPI