The design, synthesis, antioxidant, and antihypoxia activities of two new hydroxydaidzein derivatives

Journal of Chemical Research-s Pub Date : 2022-09-01 DOI:10.1177/17475198221131528

Qingyue Da, Jin Shao, Pengpeng Zhang, J. Zhang, Huiping Ma, Linlin Jing

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引用次数: 0

Abstract

7,8,3’,4’,5’-Pentahydroxyisoflavone (8,3’,5’-trihydroxydaidzein) and 6,7,8,3’,4’,5’-hexahydroxyisoflavone (6,8,3’,5’-tetrahydroxydaidzein) are synthesized via a simple and effective method using commercially available daidzein as a raw material. Their structures are confirmed using spectroscopic analyses (infrared, nuclear magnetic resonance, and mass spectrometry), and their purities are determined by high-performance liquid chromatography. The antioxidant capacities are investigated by utilizing 1,1-diphenyl-2-picryl-hydrazyl radical scavenging, superoxide radical scavenging, nitric oxide radical scavenging, reducing power, and phosphomolybdenum assays. The antihypoxia activity is examined using a hypoxia-induced PC12 cell injury model. The antioxidant and antihypoxia abilities of 8,3’,5’-trihydroxydaidzein and 6,8,3’,5’-tetrahydroxydaidzein are greatly improved in comparison with daidzein. These results indicate that 8,3’,5’-trihydroxydaidzein and 6,8,3’,5’-tetrahydroxydaidzein are excellent antioxidant agents and can be used for alleviating injury induced by hypoxia.

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两种新的羟基大豆苷元衍生物的设计、合成及其抗氧化和抗缺氧活性

以市售大豆黄酮为原料，采用简单有效的方法合成了7,8,3 '，4 '，5 ' -五羟基异黄酮(8,3 '，5 ' -三羟基大豆黄酮)和6,7,8,3 '，4 '，5 ' -六羟基异黄酮(6,8,3 '，5 ' -四羟基大豆黄酮)。它们的结构用光谱分析(红外、核磁共振和质谱)确认，它们的纯度用高效液相色谱法测定。通过1,1-二苯基-2-苦基-肼基自由基清除、超氧自由基清除、一氧化氮自由基清除、还原能力和磷钼测定来研究其抗氧化能力。采用缺氧诱导的PC12细胞损伤模型检测其抗缺氧活性。与大豆苷元相比，8,3 '，5 ' -三羟基大豆苷元和6,8,3 '，5 ' -四羟基大豆苷元的抗氧化和抗缺氧能力显著提高。上述结果表明，8,3 '，5 ' -三羟基大豆苷元和6,8,3 '，5 ' -四羟基大豆苷元是优良的抗氧化剂，可用于减轻缺氧损伤。

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来源期刊

Journal of Chemical Research-s 化学科学, 有机化学, 有机合成

自引率

0.00%

发文量

审稿时长

1 months

期刊介绍： The Journal of Chemical Research is a peer reviewed journal that publishes full-length review and research papers in all branches of experimental chemistry. The journal fills a niche by also publishing short papers, a format which favours particular types of work, e.g. the scope of new reagents or methodology, and the elucidation of the structure of novel compounds. Though welcome, short papers should not result in fragmentation of publication, they should describe a completed piece of work. The Journal is not intended as a vehicle for preliminary publications. The work must meet all the normal criteria for acceptance as regards scientific standards. Papers that contain extensive biological results or material relating to other areas of science may be diverted to more appropriate specialist journals. Areas of coverage include: Organic Chemistry; Inorganic Chemistry; Materials Chemistry; Crystallography; Computational Chemistry.