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

Masaki Ichitani; Hisako Okumura; Yugo Nakashima; Hitoshi Kinugasa; Mitsunori Honda; Ko-Ki Kunimoto

doi:10.5155/eurjchem.9.4.386-393.1794

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Published: Dec 31, 2018

DOI: https://doi.org/10.5155/eurjchem.9.4.386-393.1794

Keywords:

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

Section

Research Article

Issue

Vol. 9 No. 4 (2018): December 2018

Dates

Received 2018-10-04
Accepted 2018-10-30
Published 2018-12-31

Masaki Ichitani

Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-Machi, Kanazawa 920-1192, Japan

http://orcid.org/0000-0002-6562-2295

Hisako Okumura

Department of Materials Engineering, National Institute of Technology, Nagaoka College, 888 Nishikatakai-Machi, Nagaoka 940-8532, Japan

http://orcid.org/0000-0002-6586-0410

Yugo Nakashima

Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-Machi, Kanazawa 920-1192, Japan

http://orcid.org/0000-0002-2070-1205

Hitoshi Kinugasa

Central Research Institute, Ito En. Ltd., Shizuoka 421-0516, Japan

http://orcid.org/0000-0002-2825-2619

Mitsunori Honda

Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-Machi, Kanazawa 920-1192, Japan

http://orcid.org/0000-0001-5866-6508

Ko-Ki Kunimoto

Institute of Liberal Arts and Science, Kanazawa University, Kakuma-Machi, Kanazawa 920-1192, Japan

http://orcid.org/0000-0003-4055-0720

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.

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Ichitani, M.; Okumura, H.; Nakashima, Y.; Kinugasa, H.; Honda, M.; Kunimoto, K.-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, 386-393.

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

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