Ko Sangwon, Lim Hyun Min, Song Yeonho, Hwang Hyonseok, Lee Jeong Tae
Transportation Environmental Research Department, Korea Railroad Research Institute, Uiwang 16105, Republic of Korea.
Department of Chemistry and Institute of Applied Chemistry, Hallym University, Chuncheon 24252, Republic of Korea.
Int J Mol Sci. 2025 Jun 19;26(12):5872. doi: 10.3390/ijms26125872.
Naturally occurring antioxidants have attracted significant research interest, owing to their radical scavenging ability that can be improved via structural modifications. In this study, aromaticity-extended resveratrol analogues (-) containing chalcogens were designed and synthesized using ring closure and Horner-Wadsworth-Emmons reactions. The antioxidant activities of the derivatives were evaluated using 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABST) assay. All resveratrol derivatives (-) exhibited higher radical scavenging activities than resveratrol and analogue , with benzoselenophene-conjugated derivative demonstrating the highest activity. The improved antioxidant performance of the resveratrol derivatives was attributed to the extended π conjugation resulting from the incorporation of fused rings, benzoheteroles. Additionally, the integration of benzoheteroles into resveratrol contributed to an efficient reduction in HOMO-LUMO gaps. This study demonstrates that aromaticity extension by introducing benzofuran, benzothiophene, and benzoselenophene is a feasible strategy for improving the antioxidant activity of naturally occurring oxidants.
天然存在的抗氧化剂因其自由基清除能力而引起了广泛的研究兴趣，这种能力可通过结构修饰得到提高。在本研究中，使用闭环反应和霍纳-沃兹沃思-埃蒙斯反应设计并合成了含硫族元素的芳香性扩展白藜芦醇类似物（-）。使用2,2'-偶氮双（3-乙基苯并噻唑啉-6-磺酸）（ABST）测定法评估了衍生物的抗氧化活性。所有白藜芦醇衍生物（-）均表现出比白藜芦醇和类似物更高的自由基清除活性，其中苯并硒吩共轭衍生物表现出最高活性。白藜芦醇衍生物抗氧化性能的提高归因于稠环、苯并杂环的引入导致π共轭扩展。此外，将苯并杂环整合到白藜芦醇中有助于有效降低HOMO-LUMO能隙。本研究表明，引入苯并呋喃、苯并噻吩和苯并硒吩来扩展芳香性是提高天然抗氧化剂抗氧化活性的可行策略。
