Academic Journal
The competitive interplay of 12-oxophytodienoic acid (OPDA), protein thiols, and glutathione.
| Τίτλος: | The competitive interplay of 12-oxophytodienoic acid (OPDA), protein thiols, and glutathione. |
|---|---|
| Συγγραφείς: | Knieper M; Biochemistry and Physiology of Plants, Faculty of Biology, Bielefeld University, Germany., Schwarz R; Biochemistry and Physiology of Plants, Faculty of Biology, Bielefeld University, Germany., Vogelsang L; Biochemistry and Physiology of Plants, Faculty of Biology, Bielefeld University, Germany., Sproß J; Industrial Organic Chemistry and Biotechnology, Faculty of Chemistry, Bielefeld University, Germany., Kaya A; Biochemistry and Physiology of Plants, Faculty of Biology, Bielefeld University, Germany.; Department of Engineering Basic Sciences, Faculty of Engineering, Alanya Alaaddin Keykubat University, Turkey., Bittmann M; Industrial Organic Chemistry and Biotechnology, Faculty of Chemistry, Bielefeld University, Germany., Gröger H; Industrial Organic Chemistry and Biotechnology, Faculty of Chemistry, Bielefeld University, Germany., Viehhauser A; Biochemistry and Physiology of Plants, Faculty of Biology, Bielefeld University, Germany., Dietz KJ; Biochemistry and Physiology of Plants, Faculty of Biology, Bielefeld University, Germany. |
| Πηγή: | The FEBS journal [FEBS J] 2026 Jun; Vol. 293 (12), pp. 3683-3705. Date of Electronic Publication: 2026 Feb 05. |
| Τύπος έκδοσης: | Journal Article |
| Γλώσσα: | English |
| Στοιχεία περιοδικού: | Publisher: Published by Blackwell Pub. on behalf of the Federation of European Biochemical Societies Country of Publication: England NLM ID: 101229646 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1742-4658 (Electronic) Linking ISSN: 1742464X NLM ISO Abbreviation: FEBS J Subsets: MEDLINE |
| Imprint Name(s): | Original Publication: Oxford, UK : Published by Blackwell Pub. on behalf of the Federation of European Biochemical Societies, c2005- |
| Ιατρικοί όροι (MeSH): | Glutathione*/metabolism , Glutathione*/chemistry , Sulfhydryl Compounds*/metabolism , Sulfhydryl Compounds*/chemistry , Fatty Acids, Unsaturated*/metabolism , Fatty Acids, Unsaturated*/chemistry , Thioredoxins*/metabolism , Thioredoxins*/chemistry, Oxidation-Reduction ; Kinetics |
| Περίληψη: | Cis-(+)-12-oxophytodienoic acid (OPDA) is a bioactive oxylipin and phytohormone participating in regulation of plant stress responses, growth, and development. Due to its α, β-unsaturated carbonyl moiety, OPDA covalently binds to free thiol groups by Michael addition. This binding, termed OPDAylation, alters the activity of target proteins, such as cyclophilin 20-3 (EC:5.2.1.8) and thioredoxins, that are essential components of the cellular redox regulatory network. To function as a reversible redox regulatory mechanism, OPDAylation should be complemented by a process of de-OPDAylation allowing for fine-tuning of OPDA-dependent regulation. This study explored OPDAylation and de-OPDAylation in vitro with emphasis on the involvement of glutathione. OPDA can be transferred from protein to glutathione (GSH) and vice versa. In a competition experiment, OPDAylation of thioredoxins (TRX) occurred rapidly in the presence of GSH, while over extended incubation times, de-OPDAylation of TRX occurred due to the stoichiometric excess of GSH. These results support the hypothesis that the initial TRX-based OPDAylation is proceeding under kinetic control due to the higher reactivity of the more nucleophilic cysteine moiety in TRX compared to the one of GSH, while the OPDAylation of GSH observed at prolonged incubation time is then the result of a thermodynamically controlled process. De-OPDAylation depends on the protein's sensitivity towards OPDA, the pH and the concentration of excess thiol groups. This likely allows for precise modulation of OPDA amounts, as the rapid modification of protein activity enables subsequent induction of OPDA signaling, whereas de-OPDAylation, triggered by increasing glutathione, increasing cellular reduction or presumably enzymatically, reverses this effect. (© 2026 The Author(s). The FEBS Journal published by John Wiley & Sons Ltd on behalf of Federation of European Biochemical Societies.) |
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| Grant Information: | DI 346/22-1 Deutsche Forschungsgemeinschaft; DI 346/23-1 Deutsche Forschungsgemeinschaft; GR 3461/11-1 Deutsche Forschungsgemeinschaft |
| Contributed Indexing: | Keywords: 12‐oxophytodienoic acid; cyclophilin 20–3; retro‐Michael addition; thiol‐disulfide exchange; thioredoxin |
| Substance Nomenclature: | 67204-66-4 (12-oxophytodienoic acid) GAN16C9B8O (Glutathione) 0 (Sulfhydryl Compounds) 0 (Fatty Acids, Unsaturated) 52500-60-4 (Thioredoxins) |
| Entry Date(s): | Date Created: 20260205 Date Completed: 20260618 Latest Revision: 20260726 |
| Update Code: | 20260726 |
| PubMed Central ID: | PMC13278354 |
| DOI: | 10.1111/febs.70436 |
| PMID: | 41645029 |
| Βάση Δεδομένων: | MEDLINE |
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