Matos Maria J, Mura Francisco, Vazquez-Rodriguez Saleta, Borges Fernanda, Santana Lourdes, Uriarte Eugenio, Olea-Azar Claudio
CIQUP/Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, 4169-007 Porto, Portugal.
Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain.
Molecules. 2015 Feb 16;20(2):3290-308. doi: 10.3390/molecules20023290.
In the present work we synthesized a selected series of hydroxylated 3-phenylcoumarins 5-8, with the aim of evaluating in detail their antioxidant properties. From an in depth study of the antioxidant capacity data (ORAC-FL, ESR, CV and ROS inhibition) it was concluded that these derivatives are very good antioxidants, with very interesting profiles in all the performed assays. The study of the effect of the number and position of the hydroxyl groups on the antioxidant activity was the principal aim of this study. In particular, 7-hydroxy-3-(3'-hydroxy)phenylcoumarin (8) proved to be the most active and effective antioxidant of the selected series in four of the performed assays (ORAC-FL = 11.8, capacity of scavenging hydroxyl radicals = 54%, Trolox index = 2.33 and AI30 index = 0.18). However, the presence of two hydroxyl groups on this molecule did not increase greatly the activity profile. Theoretical evaluation of ADME properties of all the derivatives was also carried out. All the compounds can act as potential candidates for preventing or minimizing the free radical overproduction in oxidative-stress related diseases. These preliminary findings encourage us to perform a future structural optimization of this family of compounds.
在本研究中，我们合成了一系列选定的羟基化3-苯基香豆素5-8，旨在详细评估它们的抗氧化性能。通过对抗氧化能力数据（ORAC-FL、ESR、CV和ROS抑制）的深入研究得出结论，这些衍生物是非常好的抗氧化剂，在所有进行的测定中都具有非常有趣的特性。研究羟基的数量和位置对抗氧化活性的影响是本研究的主要目的。特别是，7-羟基-3-(3'-羟基)苯基香豆素（8）在进行的四项测定中（ORAC-FL = 11.8，清除羟基自由基的能力 = 54%，Trolox指数 = 2.33，AI30指数 = 0.18）被证明是所选系列中最具活性和最有效的抗氧化剂。然而，该分子上两个羟基的存在并没有显著提高其活性。还对所有衍生物的ADME性质进行了理论评估。所有这些化合物都可以作为预防或最小化氧化应激相关疾病中自由基过量产生的潜在候选物。这些初步发现鼓励我们在未来对该类化合物进行结构优化。
