Abstract：
This study aimed to explore the antioxidant and prooxidative activity of two natural furanocoumarin derivatives, Bergaptol (4-Hydroxy-7H-furo [3,2-g] [1]benzopyran-7-one, BER) and Xanthotoxol (9-Hydroxy-7H-furo [3,2-g] [1]benzopyran-7-one, XAN). The collected thermodynamic and kinetic data demonstrate that both compounds possess substantial antiradical activity against HO• and CCl3OO• radicals in physiological conditions. BER exhibited better antiradical activity in comparison to XAN, which can be attributed to the enhanced deprotonation caused by the positioning of the -OH group on the psoralen ring. In contrast to highly reactive radical species, newly formed radical species BER• and XAN• exhibited negligible reactivity towards the chosen constitutive elements of macromolecules (fatty acids, amino acids, nucleobases). Furthermore, in the presence of O2•─, the ability to regenerate newly formed radicals BER• and XAN• was observed. Conversely, in physiological conditions in the presence of Cu(II) ions, both compounds exhibit prooxidative activity. Nevertheless, the prooxidative activity of both compounds is less prominent than their antioxidant activity. Furthermore, it has been demonstrated that anionic species can engage in the creation of a chelate complex, which restricts the reduction of metal ions when reducing agents are present (O2•─ and Asc─). Moreover, studies have demonstrated that these chelating complexes can be coupled with other radical species, hence enhancing their ability to inactivate radicals. Both compounds exhibited substantial inhibitory effects against enzymes involved in the direct or indirect generation of ROS: Xanthine Oxidase (XOD), Lipoxygenase (LOX), Myeloperoxidase (MPO), NADPH oxidase (NOX).
摘要：
本研究旨在探索两种天然呋喃香豆素衍生物的抗氧化和促氧化活性,Bergaptol(4-羟基-7H-呋喃[3,2-g][1]苯并吡喃-7-酮，BER）和黄原酚（9-羟基-7H-呋喃[3,2-g][1]苯并吡喃-7-酮，XAN).收集的热力学和动力学数据表明，两种化合物在生理条件下对HO•和CCl3OO•自由基都具有明显的抗自由基活性。与XAN相比，BER表现出更好的抗自由基活性，这可以归因于由-OH基团在补骨脂素环上的定位引起的增强的去质子化。与高反应性自由基相反，新形成的自由基物种BER•和XAN•对所选择的大分子组成元素(脂肪酸，氨基酸,核碱基）。此外，在O2·存在的情况下─，观察到再生新形成的自由基BER·和XAN·的能力。相反，在存在Cu（II）离子的生理条件下，这两种化合物都表现出促氧化活性。然而，两种化合物的促氧化活性不如它们的抗氧化活性突出。此外，已经证明阴离子物种可以参与螯合物的产生，当存在还原剂(O2·──和Asc─)时，这限制了金属离子的还原。此外，研究表明，这些螯合络合物可以与其他自由基物种偶联，从而增强它们使自由基失活的能力。两种化合物都对直接或间接产生ROS的酶表现出实质性的抑制作用：黄嘌呤氧化酶（XOD），脂氧合酶(LOX),髓过氧化物酶(MPO),NADPH氧化酶(NOX)。
