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首页> 美国卫生研究院文献>PLoS Clinical Trials >An Essential Difference between the Flavonoids MonoHER and Quercetin in Their Interplay with the Endogenous Antioxidant Network
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An Essential Difference between the Flavonoids MonoHER and Quercetin in Their Interplay with the Endogenous Antioxidant Network

机译：类黄酮MonoHER和槲皮素与内源性抗氧化剂网络相互作用的本质区别

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Antioxidants can scavenge highly reactive radicals. As a result the antioxidants are converted into oxidation products that might cause damage to vital cellular components. To prevent this damage, the human body possesses an intricate network of antioxidants that pass over the reactivity from one antioxidant to another in a controlled way. The aim of the present study was to investigate how the semi-synthetic flavonoid 7-mono-O-(β-hydroxyethyl)-rutoside (monoHER), a potential protective agent against doxorubicin-induced cardiotoxicity, fits into this antioxidant network. This position was compared with that of the well-known flavonoid quercetin. The present study shows that the oxidation products of both monoHER and quercetin are reactive towards thiol groups of both GSH and proteins. However, in human blood plasma, oxidized quercetin easily reacts with protein thiols, whereas oxidized monoHER does not react with plasma protein thiols. Our results indicate that this can be explained by the presence of ascorbate in plasma; ascorbate is able to reduce oxidized monoHER to the parent compound monoHER before oxidized monoHER can react with thiols. This is a major difference with oxidized quercetin that preferentially reacts with thiols rather than ascorbate. The difference in selectivity between monoHER and quercetin originates from an intrinsic difference in the chemical nature of their oxidation products, which was corroborated by molecular quantum chemical calculations. These findings point towards an essential difference between structurally closely related flavonoids in their interplay with the endogenous antioxidant network. The advantage of monoHER is that it can safely channel the reactivity of radicals into the antioxidant network where the reactivity is completely neutralized.
机译：抗氧化剂可以清除高反应性自由基。结果，抗氧化剂被转化为氧化产物，可能会损害重要的细胞成分。为了防止这种损害，人体拥有复杂的抗氧化剂网络，该网络以可控方式将一种抗氧化剂的反应性传递给另一种抗氧化剂。本研究的目的是研究半合成的类黄酮7-单-O-（β-羟乙基）-芸苔苷（monoHER），一种潜在的抗阿霉素诱导的心脏毒性的保护剂，如何适应该抗氧化剂网络。将该位置与众所周知的类黄酮槲皮素进行了比较。本研究表明，monoHER和槲皮素的氧化产物均对GSH和蛋白质的巯基具有反应性。但是，在人血浆中，氧化槲皮素容易与蛋白质硫醇反应，而氧化的monoHER不与血浆蛋白质硫醇反应。我们的结果表明，这可以用血浆中抗坏血酸的存在来解释。抗坏血酸酯能够在被氧化的单HERH能与硫醇反应之前将被氧化的单HER还原为母体化合物单HER。这是与氧化槲皮素的主要区别，其优先与硫醇而不是抗坏血酸反应。 monoHER和槲皮素之间的选择性差异源自其氧化产物的化学性质的内在差异，这一差异已通过分子量子化学计算得到了证实。这些发现表明，结构上密切相关的类黄酮与内源性抗氧化剂网络之间的相互作用存在本质区别。 monoHER的优点在于，它可以安全地将自由基的反应性引导到抗氧化剂网络中，从而完全中和反应性。

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