The In Vitro Interaction of 12-Oxophytodienoic Acid and Related Conjugated Carbonyl Compounds with Thiol Antioxidants

Maynard D, Viehhauser A, Knieper M, Dreyer A, Manea G, Telman W, Butter F, Chibani K, Scheibe R, Dietz K-J (2021)
Biomolecules 11(3): 457.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
α,β-unsaturated carbonyls interfere with numerous plant physiological processes. One mechanism of action is their reactivity toward thiols of metabolites like cysteine and glutathione (GSH). This work aimed at better understanding these interactions. Both 12-oxophytodienoic acid (12-OPDA) and abscisic acid (ABA) conjugated with cysteine. It was found that the reactivity of α,β-unsaturated carbonyls with GSH followed the sequence trans-2-hexenal < 12-OPDA ≈ 12-OPDA-ethylester < 2-cyclopentenone << methyl vinylketone (MVK). Interestingly, GSH, but not ascorbate (vitamin C), supplementation ameliorated the phytotoxic potential of MVK. In addition, 12-OPDA and 12-OPDA-related conjugated carbonyl compounds interacted with proteins, e.g., with members of the thioredoxin (TRX)-fold family. 12-OPDA modified two cysteinyl residues of chloroplast TRX-f1. The OPDAylated TRX-f1 lost its activity to activate the Calvin–Benson-cycle enzyme fructose-1,6-bisphosphatase (FBPase). Finally, we show that 12-OPDA interacts with cyclophilin 20-3 (Cyp20-3) non-covalently and affects its peptidyl-prolyl-cis/trans isomerase activity. The results demonstrate the high potential of 12-OPDA as a diverse interactor and cellular regulator and suggest that OPDAylation may occur in plant cells and should be investigated as novel regulatory mechanism.
Stichworte
Arabidopsis thaliana; cysteine covalent modification; phytohormones; protein–ligand interaction; peroxiredoxin; cyclophilin; thiol antioxidants; thioredoxin
Erscheinungsjahr
2021
Zeitschriftentitel
Biomolecules
Band
11
Ausgabe
3
Art.-Nr.
457
eISSN
2218-273X
Finanzierungs-Informationen
Open-Access-Publikationskosten wurden durch die Universität Bielefeld gefördert.
Page URI
https://pub.uni-bielefeld.de/record/2952924

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Maynard D, Viehhauser A, Knieper M, et al. The In Vitro Interaction of 12-Oxophytodienoic Acid and Related Conjugated Carbonyl Compounds with Thiol Antioxidants. Biomolecules. 2021;11(3): 457.
Maynard, D., Viehhauser, A., Knieper, M., Dreyer, A., Manea, G., Telman, W., Butter, F., et al. (2021). The In Vitro Interaction of 12-Oxophytodienoic Acid and Related Conjugated Carbonyl Compounds with Thiol Antioxidants. Biomolecules, 11(3), 457. https://doi.org/10.3390/biom11030457
Maynard, D., Viehhauser, A., Knieper, M., Dreyer, A., Manea, G., Telman, W., Butter, F., Chibani, K., Scheibe, R., and Dietz, K. - J. (2021). The In Vitro Interaction of 12-Oxophytodienoic Acid and Related Conjugated Carbonyl Compounds with Thiol Antioxidants. Biomolecules 11:457.
Maynard, D., et al., 2021. The In Vitro Interaction of 12-Oxophytodienoic Acid and Related Conjugated Carbonyl Compounds with Thiol Antioxidants. Biomolecules, 11(3): 457.
D. Maynard, et al., “The In Vitro Interaction of 12-Oxophytodienoic Acid and Related Conjugated Carbonyl Compounds with Thiol Antioxidants”, Biomolecules, vol. 11, 2021, : 457.
Maynard, D., Viehhauser, A., Knieper, M., Dreyer, A., Manea, G., Telman, W., Butter, F., Chibani, K., Scheibe, R., Dietz, K.-J.: The In Vitro Interaction of 12-Oxophytodienoic Acid and Related Conjugated Carbonyl Compounds with Thiol Antioxidants. Biomolecules. 11, : 457 (2021).
Maynard, Daniel, Viehhauser, Andrea, Knieper, Madita, Dreyer, Anna, Manea, Ghamdan, Telman, Wilena, Butter, Falk, Chibani, Kamel, Scheibe, Renate, and Dietz, Karl-Josef. “The In Vitro Interaction of 12-Oxophytodienoic Acid and Related Conjugated Carbonyl Compounds with Thiol Antioxidants”. Biomolecules 11.3 (2021): 457.
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2021-03-22T09:20:53Z
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