Department of Bioanalytical Chemistry, Faculty of Pharmacy, University of Debrecen, Debrecen H-4032, Hungary.
Department of Biophysics and Cell Biology, Faculty of Medicine, University of Debrecen, Debrecen H-4032, Hungary.
Molecules. 2018 Nov 30;23(12):3161. doi: 10.3390/molecules23123161.
Six new flavonols (⁻) were synthesized with Claisen⁻Schmidt and Suzuki reactions and they were fully characterized by spectroscopic methods. In order to evaluate their antioxidant activities, their oxygen radical absorption capacity and ferric reducing antioxidant power were measured, along with their free radical scavenging activity against 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) and 2,2-diphenyl-1-picrylhydrazylradicals. In addition, their cytotoxicity on H9c2 cardiomyoblast cells was also assessed by a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. Compounds bearing the phenyl--dimethylamino group (, , and ) exhibited promising antioxidant potency and did not have any cytotoxic effect. After a consideration of these data, the oxidative transformation of the compound was investigated in vitro with a chemical Fenton reaction and the identification of the formed oxidation products was performed by mass spectrometry. Two potential metabolites were detected. Based on these results, compound can be a model compound for future developments. Overall, this work has proved the involvement of the phenyl--dimethylamino group in the antioxidant activity of flavonols.
六位新的类黄酮（⁻）通过 Claisen-Schmidt 和 Suzuki 反应合成，并通过光谱方法进行了全面表征。为了评估它们的抗氧化活性，测量了它们的氧自由基吸收能力和铁还原抗氧化能力，以及它们对 2,2'-偶氮-双（3-乙基苯并噻唑啉-6-磺酸）和 2,2-二苯基-1-苦基肼自由基的清除活性。此外，还通过 3-(4,5-二甲基噻唑-2-基)-2,5-二苯基四氮唑溴化物测定法评估了它们对 H9c2 心肌细胞的细胞毒性。带有苯基--二甲氨基的化合物（、、和）表现出有希望的抗氧化效力，并且没有任何细胞毒性作用。在考虑了这些数据之后，通过化学芬顿反应在体外研究了化合物的氧化转化，并通过质谱法对形成的氧化产物进行了鉴定。检测到两种潜在的代谢产物。基于这些结果，化合物可以成为未来开发的模型化合物。总的来说，这项工作证明了苯基--二甲氨基在类黄酮的抗氧化活性中的参与。
