European Journal of Chemistry 2018, 9(4), 386-393 | doi: https://doi.org/10.5155/eurjchem.9.4.386-393.1794 | Get rights and content






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Spectroscopic characterization of thiol adducts formed in the reaction of 4-methylcatechol with DPPH in the presence of N-acetylcysteine


Masaki Ichitani (1) orcid , Hisako Okumura (2) orcid , Yugo Nakashima (3) orcid , Hitoshi Kinugasa (4) orcid , Mitsunori Honda (5,*) orcid , Ko-Ki Kunimoto (6) orcid

(1) Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-Machi, Kanazawa 920-1192, Japan
(2) Department of Materials Engineering, National Institute of Technology, Nagaoka College, 888 Nishikatakai-Machi, Nagaoka 940-8532, Japan
(3) Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-Machi, Kanazawa 920-1192, Japan
(4) Central Research Institute, Ito En. Ltd., Shizuoka 421-0516, Japan
(5) Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-Machi, Kanazawa 920-1192, Japan
(6) Institute of Liberal Arts and Science, Kanazawa University, Kakuma-Machi, Kanazawa 920-1192, Japan
(*) Corresponding Author

Received: 04 Oct 2018 | Revised: 29 Oct 2018 | Accepted: 30 Oct 2018 | Published: 31 Dec 2018 | Issue Date: December 2018

Abstract


Nucleophiles such as thiol compounds have enhancing effects on the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activities of polyphenols. Several authors have suggested that regeneration of the catechol structure from o-quinone plays a key role in enhanced radical scavenging activity. We therefore explored the reaction of 4-methyl catechol (MC) with DPPH in the presence of N-acetylcysteine (NACys) to clarify the mechanism underlying activity enhancement. Four types of NACys adducts were isolated and purified by preparative HPLC after the reactions reached equilibrium and their structures were characterized spectroscopically using UV-Vis absorption, NMR, and LC-MS. Oxidation of MC using a periodate resin and subsequent reaction with NACys were also studied. LC-MS analyses revealed that a mono-NACys adduct is produced as the major product in the reaction of MC quinone with NACys, and direct reduction by NACys occurs in reactions with NACys MC quinones.


Keywords


Quinones; Oxidation; Thiol adduct; 4-Methylcatechol; N-Acetylcysteine; 2,2-Diphenyl-1-picrylhydrazyl (DPPH)

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DOI: 10.5155/eurjchem.9.4.386-393.1794

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Funding information


Kanazawa University, SAKIGAKE project, Kanazawa 920-1192, Japan

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How to cite


Ichitani, M.; Okumura, H.; Nakashima, Y.; Kinugasa, H.; Honda, M.; Kunimoto, K. Eur. J. Chem. 2018, 9(4), 386-393. doi:10.5155/eurjchem.9.4.386-393.1794
Ichitani, M.; Okumura, H.; Nakashima, Y.; Kinugasa, H.; Honda, M.; Kunimoto, K. Spectroscopic characterization of thiol adducts formed in the reaction of 4-methylcatechol with DPPH in the presence of N-acetylcysteine. Eur. J. Chem. 2018, 9(4), 386-393. doi:10.5155/eurjchem.9.4.386-393.1794
Ichitani, M., Okumura, H., Nakashima, Y., Kinugasa, H., Honda, M., & Kunimoto, K. (2018). Spectroscopic characterization of thiol adducts formed in the reaction of 4-methylcatechol with DPPH in the presence of N-acetylcysteine. European Journal of Chemistry, 9(4), 386-393. doi:10.5155/eurjchem.9.4.386-393.1794
Ichitani, Masaki, Hisako Okumura, Yugo Nakashima, Hitoshi Kinugasa, Mitsunori Honda, & Ko-Ki Kunimoto. "Spectroscopic characterization of thiol adducts formed in the reaction of 4-methylcatechol with DPPH in the presence of N-acetylcysteine." European Journal of Chemistry [Online], 9.4 (2018): 386-393. Web. 9 Jul. 2020
Ichitani, Masaki, Okumura, Hisako, Nakashima, Yugo, Kinugasa, Hitoshi, Honda, Mitsunori, AND Kunimoto, Ko-Ki. "Spectroscopic characterization of thiol adducts formed in the reaction of 4-methylcatechol with DPPH in the presence of N-acetylcysteine" European Journal of Chemistry [Online], Volume 9 Number 4 (31 December 2018)

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