School of Food Science and Biotechnology, Zhejiang Gongshang University, Hangzhou 310018, China.
Department of Chemistry, Cape Breton University, Sydney, Nova Scotia B1P 6L2, Canada.
J Agric Food Chem. 2023 Aug 23;71(33):12587-12596. doi: 10.1021/acs.jafc.3c03284. Epub 2023 Aug 10.
Gallic acid (GA, 3,4,5-trihydroxybenzoic acid) is a widely used natural food additive of interest to food chemistry researchers, especially regarding its effects on myofibrillar protein (MP) oxidation. However, existing studies regarding MP oxidation by GA-combined with Fenton reagents are inconsistent, and the detailed mechanisms have not been fully elucidated. This work validated hydroxyl radical (HO) as the primary oxidant for MP carbonylation; in addition, it revealed three functions of GA in the Fenton oxidation of MP. By coordination with Fe(III), GA reduces Fe(III) to generate Fe(II), which is the critical reagent for HO generation; meanwhile, the coordination improves the availability and reactivity of Fe(III) under weakly acidic and near-neutral pH, i.e., pH 4-6. Second, the intermediates formed during GA oxidation, including semiquinone and quinone, promoted Fenton reactivity by accelerating Fe catalytic cycling. Finally, GA can scavenge HO radicals, thus exhibiting a certain degree of antioxidant property. All three functions contribute to MP oxidation as observed in GA-containing meat.
没食子酸(GA,3,4,5-三羟基苯甲酸)是一种广泛应用于食品化学研究的天然食品添加剂,尤其因其对肌原纤维蛋白(MP)氧化的影响而受到关注。然而,关于 GA 与 Fenton 试剂联合作用下 MP 氧化的现有研究结果并不一致,其详细机制尚未完全阐明。本研究证实羟基自由基(HO)是 MP 羰基化的主要氧化剂;此外,还揭示了 GA 在 MP 的 Fenton 氧化中的三种作用。GA 通过与 Fe(III)配位,将 Fe(III)还原为 Fe(II),后者是 HO 生成的关键试剂;同时,这种配位作用提高了 Fe(III)在弱酸性和近中性 pH(即 4-6)条件下的可用性和反应活性。其次,GA 氧化过程中形成的中间体,包括半醌和醌,通过加速 Fe 催化循环来促进 Fenton 反应性。最后,GA 可以清除 HO 自由基,因此表现出一定程度的抗氧化性能。这三种作用都有助于含 GA 的肉中观察到的 MP 氧化。