Reactivities of Hydroxycinnamic Acid Derivatives Involving Caffeic Acid toward Electrogenerated Superoxide in N,N-Dimethylformamide
Abstract
:1. Introduction
2. Materials and Methods
2.1. Chemicals
2.2. Cyclic Voltammetry and In Situ Electrolytic ESR/UV–Vis Spectrum Measurements
2.3. Theoretical Calculations
3. Results and Discussion
3.1. Cyclic Voltammetry of O2/O2•− in the Presence of HCAs
3.2. In Situ Electrolytic ESR/UV–Vis Spectral Analyses of O2/O2•− in the Presence of HCAs
3.3. DFT Optimization of the Stable Structure of CafH2(COOH) and Its Deprotonated Anion
3.4. Change in HOMO-LUMO Energies during PCET between CafH2(COOH) and O2•−
3.5. Change in Free Energies during PCET between CafH2(COOH) and O2•−
3.6. Potential-Energy Surfaces of the PCET between CafH2(COOH) and O2•−
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
- Boerjan, W.; Ralph, J.; Baucher, M. Lignin Biosynthesis. Annu. Rev. Plant Biol. 2003, 54, 519–546. [Google Scholar] [CrossRef] [PubMed]
- Gülçin, I. Antioxidant activity of caffeic acid (3,4-dihydroxycinnamic acid). Toxicology 2006, 217, 213–220. [Google Scholar] [CrossRef]
- Hong Chen, J.; Ho, C.-T. Antioxidant Activities of Caffeic Acid and Its Related Hydroxycinnamic Acid Compounds. J. Agric. Food Chem. 1997, 45, 2374–2378. [Google Scholar] [CrossRef]
- Zielińska, D.; Zieliński, H.; Laparra-Llopis, J.M.; Szawara-Nowak, D.; Honke, J.; Giménez-Bastida, J.A. Caffeic acid modulates processes associated with intestinal inflammation. Nutrients 2021, 13, 554. [Google Scholar] [CrossRef] [PubMed]
- Sato, Y.; Itagaki, S.; Kurokawa, T.; Ogura, J.; Kobayashi, M.; Hirano, T.; Sugawara, M.; Iseki, K. In vitro and in vivo antioxidant properties of chlorogenic acid and caffeic acid. Int. J. Pharm. 2011, 403, 136–138. [Google Scholar] [CrossRef]
- Nasr Bouzaiene, N.; Kilani Jaziri, S.; Kovacic, H.; Chekir-Ghedira, L.; Ghedira, K.; Luis, J. The effects of caffeic, coumaric and ferulic acids on proliferation, superoxide production, adhesion and migration of human tumor cells in vitro. Eur. J. Pharmacol. 2015, 766, 99–105. [Google Scholar] [CrossRef]
- Simić, A.; Manojlović, D.; Šegan, D.; Todorović, M. Electrochemical behavior and antioxidant and prooxidant activity of natural phenolics. Molecules 2007, 12, 2327–2340. [Google Scholar] [CrossRef] [Green Version]
- Masek, A.; Chrzescijanska, E.; Latos, M. Determination of antioxidant activity of caffeic acid and p-coumaric acid by using electrochemical and spectrophotometric assays. Int. J. Electrochem. Sci. 2016, 11, 10644–10658. [Google Scholar] [CrossRef]
- Hotta, H.; Ueda, M.; Nagano, S.; Tsujino, Y.; Koyama, J.; Osakai, T. Mechanistic study of the oxidation of caffeic acid by digital simulation of cyclic voltammograms. Anal. Biochem. 2002, 303, 66–72. [Google Scholar] [CrossRef]
- VanBesiena, E.; Marques, M.P.M. Ab initio conformational study of caffeic acid. J. Mol. Struct. THEOCHEM 2003, 625, 265–275. [Google Scholar] [CrossRef] [Green Version]
- Giacomelli, C.; da Silva Miranda, F.; Gonçalves, N.S.; Spinelli, A. Antioxidant activity of phenolic and related compounds: A density functional theory study on the O-H bond dissociation enthalpy. Redox Rep. 2004, 9, 263–269. [Google Scholar] [CrossRef] [PubMed]
- Mazzone, G.; Russo, N.; Toscano, M. Antioxidant properties comparative study of natural hydroxycinnamic acids and structurally modified derivatives: Computational insights. Comput. Theor. Chem. 2016, 1077, 39–47. [Google Scholar] [CrossRef]
- Amić, A.; Marković, Z.; Klein, E.; Dimitrić Marković, J.M.; Milenković, D. Theoretical study of the thermodynamics of the mechanisms underlying antiradical activity of cinnamic acid derivatives. Food Chem. 2018, 246, 481–489. [Google Scholar] [CrossRef] [PubMed]
- Nsangou, M.; Fifen, J.J.; Dhaouadi, Z.; Lahmar, S. Hydrogen atom transfer in the reaction of hydroxycinnamic acids with {radical dot}OH and {radical dot}HO2 radicals: DFT study. J. Mol. Struct. THEOCHEM 2008, 862, 53–59. [Google Scholar] [CrossRef]
- Singh, P.S.; Evans, D.H. Study of the electrochemical reduction of dioxygen in acetonitrile in the presence of weak acids. J. Phys. Chem. B 2006, 110, 637–644. [Google Scholar] [CrossRef]
- Nakayama, T.; Uno, B. Concerted two-proton-coupled electron transfer from catechols to superoxide via hydrogen bonds. Electrochim. Acta 2016, 208, 304–309. [Google Scholar] [CrossRef]
- Nakayama, T.; Uno, B. Quinone-hydroquinone π-conjugated redox reaction involving proton-coupled electron transfer plays an important role in scavenging superoxide by polyphenolic antioxidants. Chem. Lett. 2010, 39, 162–164. [Google Scholar] [CrossRef]
- Nakayama, T.; Uno, B. Importance of proton-coupled electron transfer from natural phenolic compounds in superoxide scavenging. Chem. Pharm. Bull. 2015, 63, 967–973. [Google Scholar] [CrossRef] [Green Version]
- Nakayama, T.; Uno, B. Structural properties of 4-substituted phenols capable of proton-coupled electron transfer to superoxide. Int. J. Adv. Res. Chem. Sci. 2016, 3, 11–19. [Google Scholar] [CrossRef]
- Biela, M.; Rimarčík, J.; Senajová, E.; Kleinová, A.; Klein, E. Antioxidant action of deprotonated flavonoids: Thermodynamics of sequential proton-loss electron-transfer. Phytochemistry 2020, 180, 112528. [Google Scholar] [CrossRef]
- Nanni, E.J.; Birge, R.R.; Hubbard, L.M.; Morrison, M.M.; Sawyer, D.T. Oxidation and dismutation of superoxide ion solutions to molecular oxygen. singlet vs. triplet state. Inorg. Chem. 1981, 20, 737–741. [Google Scholar] [CrossRef]
- Nanni, E.J.; Stallings, M.D.; Sawyer, D.T. Does superoxide ion oxidize catechol, α-tocopherol, and ascorbic acid by direct electron transfer? J. Am. Chem. Soc. 1980, 102, 4481–4485. [Google Scholar] [CrossRef]
- Song, C.; Zhang, J. Electrocatalytic oxygen reduction reaction. In PEM Fuel Cell Electrocatalysts and Catalyst Layers: Fundamentals and Applications; Springer: Berlin, Germany, 2008; pp. 89–134. ISBN 9781848009356. [Google Scholar]
- Fridovich, I. Superoxide dismutase. In Encyclopedia of Biological Chemistry, 2nd ed.; Elsevier Inc.: Amsterdam, The Netherlands, 2013; pp. 352–354. ISBN 9780123786319. [Google Scholar]
- Nakayama, T.; Honda, R. Electrochemical and Mechanistic Study of Superoxide Elimination by Mesalazine through Proton-Coupled Electron Transfer. Pharmaceuticals 2021, 14, 120. [Google Scholar] [CrossRef]
- Nakayama, T.; Honda, R.; Kuwata, K.; Usui, S.; Uno, B. Electrochemical and mechanistic study of reactivities of α-, β-, γ-, and δ-tocopherol toward electrogenerated superoxide in N,N-dimethylformamide through proton-coupled electron transfer. Antioxidants 2022, 11, 9. [Google Scholar] [CrossRef] [PubMed]
- Okumura, N.; Uno, B. Electronic spectra of the electrogenerated 1,4-benzoquinone π-dianion and the strongly hydrogen-bonded charge-transfer complex with methanol. Bull. Chem. Soc. Jpn. 1999, 72, 1213–1217. [Google Scholar] [CrossRef]
- Frisch, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Scalmani, G.; Barone, V.; Petersson, G.A.; Nakatsuji, H.; Li, X.; et al. Gaussian 16, Rev. B.01; Gaussian, Inc.: Wallingford, CT, USA, 2016; ISBN 9781935522027. [Google Scholar]
- Quintero-Saumeth, J.; Rincón, D.A.; Doerr, M.; Daza, M.C. Concerted double proton-transfer electron-transfer between catechol and superoxide radical anion. Phys. Chem. Chem. Phys. 2017, 19, 26179–26190. [Google Scholar] [CrossRef]
- Reed, A.E.; Weinstock, R.B.; Weinhold, F. Natural population analysis. J. Chem. Phys. 1985, 83, 735–746. [Google Scholar] [CrossRef]
- Meng, Q.; Lin, X.; Zhai, Y.; Zhang, L.; Zhang, P.; Sheng, L. A theoretical investigation on Bell-Evans-Polanyi correlations for hydrogen abstraction reactions of large biodiesel molecules by H and OH radicals. Combust. Flame 2020, 214, 394–406. [Google Scholar] [CrossRef]
Compounds | PT1 | PT2 | PT3 | PT4 | ET1 | ET2 | ET3 | Concerted 1 | Total 2 |
---|---|---|---|---|---|---|---|---|---|
CafH2(COOH) | −8.9 | −279.7 | 302.9 | −177.3 | 406.8 | 136.0 | −344.2 | −41.3 | −50.2 |
Ferulic acid | 6.2 | −476.9 | 313.1 | −79.6 | 532.2 | 49.0 | −343.6 | −30.5 | −24.3 |
Isoferulic acid | 4.5 | −471.2 | 298.2 | −77.1 | 517.0 | 41.2 | −334.1 | −35.9 | −31.4 |
Et-CafH2 | −5.4 | −365.8 | 371.3 | −85.9 | 402.9 | 42.5 | −414.6 | −43.3 | −48.7 |
p-Coumaric acid | 7.7 | −353.7 | 301.9 | −79.4 | 420.1 | 58.6 | −322.8 | −20.8 | −13.1 |
Reactants 1 | FR | TS (Ea) | PC | FP |
---|---|---|---|---|
CafH2(COOH) (+O2•−) | 39.8 | 53.8 | −19.9 | −10.4 |
CafH2(COO)− (+O2•−) | 30.1 | 50.0 | −27.6 | −10.8 |
Et-CafH2 (+O2•−) | 38.7 | 53.2 | −20.3 | −10.0 |
CatH2 (+O2•−) | 71.6 | 52.5 | −20.9 | 45.3 |
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Nakayama, T.; Uno, B. Reactivities of Hydroxycinnamic Acid Derivatives Involving Caffeic Acid toward Electrogenerated Superoxide in N,N-Dimethylformamide. Electrochem 2022, 3, 347-360. https://doi.org/10.3390/electrochem3030024
Nakayama T, Uno B. Reactivities of Hydroxycinnamic Acid Derivatives Involving Caffeic Acid toward Electrogenerated Superoxide in N,N-Dimethylformamide. Electrochem. 2022; 3(3):347-360. https://doi.org/10.3390/electrochem3030024
Chicago/Turabian StyleNakayama, Tatsushi, and Bunji Uno. 2022. "Reactivities of Hydroxycinnamic Acid Derivatives Involving Caffeic Acid toward Electrogenerated Superoxide in N,N-Dimethylformamide" Electrochem 3, no. 3: 347-360. https://doi.org/10.3390/electrochem3030024