Department of Analytical Chemistry, Faculty of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan.
Toxicol In Vitro. 2011 Oct;25(7):1320-7. doi: 10.1016/j.tiv.2011.04.024. Epub 2011 May 10.
Phenolic compounds are widely used in food and cosmetics to prevent undesirable oxidation. On the other hand, phenolic compounds are also strong reducing agents and under in vitro conditions and in the presence of copper ion, they can act as pro-oxidants. In this study, we conducted electron spin resonance (ESR) measurements for the increase in reactive oxygen species (ROS) in relation to their structure and interaction with transition metals. Moreover, the antioxidant activity was assessed with the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay, and the pro-oxidant effect of phenolic compounds on DNA damage was assessed by measuring 8-hydroxy-2'-deoxyguanosine (8-OHdG), which is effectively formed during oxidative damage. In conclusion, ortho-dihydroxyl groups that can chelate with Cu(2+) induce the greatest pro-oxidant activity. Moreover, the interaction between phenolic compounds and copper induced to H(2)O(2). The obtained results indicated that ROS participated in oxidative DNA damage induced by phenolic compounds in the presence of Cu(2+).
酚类化合物广泛应用于食品和化妆品中，以防止不良氧化。另一方面，酚类化合物也是很强的还原剂，在体外条件下和存在铜离子的情况下，它们可以作为促氧化剂。在这项研究中，我们进行了电子自旋共振（ESR）测量，以增加与结构和与过渡金属相互作用有关的活性氧物种（ROS）。此外，还通过 1,1-二苯基-2-苦基肼（DPPH）测定法评估了抗氧化活性，通过测量 8-羟基-2'-脱氧鸟苷（8-OHdG）评估了酚类化合物对 DNA 损伤的促氧化剂作用，该物质在氧化损伤过程中有效形成。总之，能够螯合 Cu(2+)的邻二羟基基团诱导出最大的促氧化剂活性。此外，酚类化合物与铜之间的相互作用诱导了 H(2)O(2)的形成。所得结果表明，在 Cu(2+)存在下，ROS 参与了由酚类化合物引起的氧化 DNA 损伤。
