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Antioxidant Activity of Caffeic Acid against Iron-Induced Free Radical Generation—A Chemical Approach

机译：咖啡酸对铁诱导的自由基生成的抗氧化活性—化学方法

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摘要

Caffeic acid (CA) is a phenolic compound widely found in coffee beans with known beneficial effects in vivo. Many studies showed that CA has anti-inflammatory, anti-mutagenic, antibacterial and anti-carcinogenic properties, which could be linked to its antioxidant activity. Taking in consideration the reported in vitro antioxidant mechanism of other polyphenols, our working hypothesis was that the CA antioxidant activity could be related to its metal-chelating property. With that in mind, we sought to investigate the chemical antioxidant mechanism of CA against in vitro iron-induced oxidative damage under different assay conditions. CA was able to prevent hydroxyl radical formation promoted by the classical Fenton reaction, as determined by 2-deoxyribose (2-DR) oxidative degradation and DMPO hydroxylation. In addition to its ability to prevent hydroxyl radical formation, CA had a great inhibition of membrane lipid peroxidation. In the lipid peroxidation assays CA acted as both metal-chelator and as hydrogen donor, preventing the deleterious action promoted by lipid-derived peroxyl and alkoxyl radicals. Our results indicate that the observed antioxidant effects were mostly due to the formation of iron-CA complexes, which are able to prevent 2-DR oxidation and DMPO hydroxylation. Noteworthy, the formation of iron-CA complexes and prevention of oxidative damage was directly related to the pH of the medium, showing better antioxidant activity at higher pH values. Moreover, in the presence of lipid membranes the antioxidant potency of CA was much higher, indicating its enhanced effectiveness in a hydrophobic environment. Overall, our results show that CA acts as an antioxidant through an iron chelating mechanism, preventing the formation of free hydroxyl radicals and, therefore, inhibiting Fenton-induced oxidative damage. The chemical properties of CA described here—in association with its reported signaling effects—could be an explanation to its beneficial effects observed in vivo.
机译：咖啡酸（CA）是一种广泛存在于咖啡豆中的酚类化合物，具有体内已知的有益作用。许多研究表明，CA具有抗炎，抗诱变，抗菌和抗癌的特性，这可能与其抗氧化活性有关。考虑到已报道的其他多酚的体外抗氧化机理，我们的工作假设是CA抗氧化活性可能与其金属螯合性能有关。考虑到这一点，我们试图研究CA在不同测定条件下对体外铁诱导的氧化损伤的化学抗氧化机理。通过2-脱氧核糖（2-DR）氧化降解和DMPO羟基化确定，CA能够阻止经典芬顿反应促进的羟基自由基形成。除了具有防止羟基自由基形成的能力外，CA还具有很大的膜脂过氧化抑制作用。在脂质过氧化测定中，CA既充当金属螯合剂又充当氢供体，从而防止了脂质衍生的过氧和烷氧基所促进的有害作用。我们的结果表明，观察到的抗氧化作用主要归因于铁-CA复合物的形成，该复合物能够防止2-DR氧化和DMPO羟基化。值得注意的是，铁-CA复合物的形成和氧化损伤的预防与介质的pH直接相关，在较高的pH值下显示出更好的抗氧化活性。此外，在脂质膜的存在下，CA的抗氧化能力要高得多，表明其在疏水环境中的效力增强。总体而言，我们的结果表明，CA通过铁螯合机制作为抗氧化剂，可防止游离羟基的形成，因此可抑制Fenton诱导的氧化损伤。此处描述的CA的化学性质及其报告的信号传导作用，可以解释其在体内观察到的有益作用。

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