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<p>The synergistic antioxidant effect and underlying chemical interactions between cysteine and catechol derivatives (4-methylcatechol, caffeic acid, and catechin) were investigated under the Ferric Reducing Antioxidant Power (FRAP) assay. The presence of cysteine was observed to cause a significant synergistic increase in FRAP activity for all tested phenolics. To elucidate the molecular basis for this synergy, the reaction products of the 4-methylcatechol (MC) model were examined by UPLC-ESI-QTOF-MS/MS. The analysis clarified the formation of mono-cysteinyl-MC adducts as the primary reaction products, alongside self-interaction reaction products including MC dimers and cystine. Time-course monitoring of those reaction products revealed that cysteine intercepts the reactive MC quinone, resulting in a significant suppression of MC dimer formation accompanied by the rapid formation of mono-cysteinyl adduct. These results indicate that the synergistic effect is predominantly caused by the rapid formation of thiol adducts, a pathway that outcompetes the oxidative polymerization of the parent phenolic.</p>

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Mechanistic insights into the synergistic role of cysteine in enhancing the ferric reducing antioxidant power of catechol derivatives

  • 期刊论文

  • 发表日期：

    2026年3月3日

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  • Haoran Xing,
  • Yuman Jiao,
  • Yingjie Qiao,
  • Tianshuo Feng,
  • Yunfeng Hu,
  • Varoujan Yaylayan

摘要

The synergistic antioxidant effect and underlying chemical interactions between cysteine and catechol derivatives (4-methylcatechol, caffeic acid, and catechin) were investigated under the Ferric Reducing Antioxidant Power (FRAP) assay. The presence of cysteine was observed to cause a significant synergistic increase in FRAP activity for all tested phenolics. To elucidate the molecular basis for this synergy, the reaction products of the 4-methylcatechol (MC) model were examined by UPLC-ESI-QTOF-MS/MS. The analysis clarified the formation of mono-cysteinyl-MC adducts as the primary reaction products, alongside self-interaction reaction products including MC dimers and cystine. Time-course monitoring of those reaction products revealed that cysteine intercepts the reactive MC quinone, resulting in a significant suppression of MC dimer formation accompanied by the rapid formation of mono-cysteinyl adduct. These results indicate that the synergistic effect is predominantly caused by the rapid formation of thiol adducts, a pathway that outcompetes the oxidative polymerization of the parent phenolic.