Dutta Madhu Sudan, Mahapatra Prithwish, Ghosh Ashutosh, Basu Soumalee
Department of Microbiology, University of Calcutta, 35, Ballygunge Circular Road, Kolkata, 700019, India.
Department of Chemistry, University of Calcutta, 92, A.P.C. Road, Kolkata, 700009, India.
Mol Divers. 2022 Apr;26(2):1101-1113. doi: 10.1007/s11030-021-10232-4. Epub 2021 May 16.
Oxidative stress that damages cellular components affects various organs including the brain. It is thus believed to play an active role in neurodegenerative diseases, wherein the intrinsic antioxidant enzymes metabolize toxic intermediates. For therapeutic purpose, instead of antioxidant enzymes, small organic compounds as antioxidants may be more effective. Here, reducing power and electrochemical behavior of some flavanols, flavanonols, flavones, flavonols and O-methylated flavonols have been estimated and confirmed by the calculated bond dissociation energy. Compared to other classes, flavonols exhibited increased reducing power that decreased with methylation of the oxygen atom in the B-ring. Gossypetin emerged as the most effective of these flavonols. Generally, compounds with two hydroxyl groups in two consecutive positions of the phenyl ring and an enolic group in the C-ring with more preference for the hydroxyl group in the ortho position with respect to each other in the catechol moiety showed major activity. 5 position of the A-ring showed the least effect on the activity. The present understanding therefore may be applied for identifying compounds to be used as scaffold for designing potent antioxidants.
损害细胞成分的氧化应激会影响包括大脑在内的各种器官。因此,人们认为氧化应激在神经退行性疾病中起积极作用,在这类疾病中,内源性抗氧化酶会代谢有毒中间体。出于治疗目的,作为抗氧化剂的小有机化合物可能比抗氧化酶更有效。在此,通过计算键离解能估算并确认了一些黄烷醇、黄烷酮醇、黄酮、黄酮醇和O-甲基化黄酮醇的还原能力和电化学行为。与其他类别相比,黄酮醇表现出增强的还原能力,这种能力会随着B环中氧原子的甲基化而降低。棉皮素是这些黄酮醇中最有效的。一般来说,在苯环的两个连续位置带有两个羟基且在C环带有一个烯醇基的化合物,在儿茶酚部分中彼此邻位的羟基更受青睐,这些化合物表现出主要活性。A环的5位对活性的影响最小。因此,目前的认识可用于鉴定用作设计强效抗氧化剂支架的化合物。