Athira E, Darsan S Akhila, Davis Shinta, Rajan Vijisha K
Department of Nanoscience and Technology, University of Calicut, Malappuram, 673635, India.
Plant Mol Biol. 2025 Mar 24;115(2):50. doi: 10.1007/s11103-025-01567-9.
Seven flavanones underwent computational evaluation to determine their effectiveness in filtering UV radiation and scavenging free radicals. The investigated flavanones exhibited enhanced radical scavenging capabilities relative to the parent flavanone, with Hesperidin demonstrating the highest EA and Qmax values, consistent with its antireductant activity. The remaining flavanones displayed lower IE values, suggesting their antioxidant efficacy. Spectroscopic analysis revealed that the HOMO-LUMO and HOMO-1-LUMO transitions are the primary electronic transitions in the UV-Visible spectra of the studied flavanones. Their absorption within the UV-A and UV-B range (260-345 nm) indicates potential utility as UV filters. Theoretical calculations demonstrate that the reactivity of flavanones is concentrated in ring [B], with a reactivity order of 3' > 4' > 2' > 6 > 7 > 5. The BDE values reveal that the 3'-OH group has the lowest value, followed by the 4' position, while hydrogen bonding is responsible for the increased BDE value at position 5. The values of ΔBDE and ΔAIP, relative to phenol, provide a framework for elucidating the preferred mechanism, HAT or SET, underlying the antioxidant behavior. Molecular docking simulations identified hesperetin, 2'-Hydroxyflavanone, 4'-Hydroxyflavanone, Eriodictyol, and Naringenin as potential MAO-B inhibitors, outperforming their synthetic counterparts in this regard.
对七种黄烷酮进行了计算评估，以确定它们在过滤紫外线辐射和清除自由基方面的有效性。与母体黄烷酮相比，所研究的黄烷酮表现出增强的自由基清除能力，橙皮苷的电子亲和力（EA）和最大清除量（Qmax）值最高，与其抗氧化活性一致。其余的黄烷酮显示出较低的电离能（IE）值，表明了它们的抗氧化功效。光谱分析表明，最高占据分子轨道-最低未占据分子轨道（HOMO-LUMO）和最高占据分子轨道-1-最低未占据分子轨道（HOMO-1-LUMO）跃迁是所研究黄烷酮紫外可见光谱中的主要电子跃迁。它们在紫外-A和紫外-B范围（260-345纳米）内的吸收表明其作为紫外线滤光剂的潜在用途。理论计算表明，黄烷酮的反应活性集中在环[B]上，反应活性顺序为3′＞4′＞2′＞6＞7＞5。键解离能（BDE）值表明，3′-羟基的BDE值最低，其次是4′位，而氢键导致5位的BDE值增加。相对于苯酚的ΔBDE和ΔAIP值为阐明抗氧化行为背后的首选机制——氢原子转移（HAT）或单电子转移（SET）提供了框架。分子对接模拟确定橙皮素、2′-羟基黄烷酮、4′-羟基黄烷酮、圣草酚和柚皮素为潜在的单胺氧化酶-B（MAO-B）抑制剂，在这方面优于它们的合成类似物。
