食品与发酵工业 >

2023 , Vol. 49 >Issue 19: 152 - 159

DOI: https://doi.org/10.13995/j.cnki.11-1802/ts.033022

研究报告

氧化白藜芦醇的合成工艺改进及其抗氧化活性

  • 陈莹 ,
  • 周华 ,
  • 晏日安
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  • (暨南大学 理工学院,广东 广州,510632)
第一作者:硕士研究生(晏日安教授为通信作者,E-mail:yanrian813@163.com)

收稿日期: 2022-07-19

  修回日期: 2022-08-10

  网络出版日期: 2023-11-01

基金资助

广州市科技计划项目(201903010070)

收起

Improved synthesis and antioxidant activity of oxyresveratrol

  • CHEN Ying ,
  • ZHOU Hua ,
  • YAN Ri'an
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  • (College of Science and Engineering, Jinan University, Guangzhou 510632, China)

Received date: 2022-07-19

  Revised date: 2022-08-10

  Online published: 2023-11-01

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摘要

将用于制备E型烯烃的Wittig-Horner反应法应用于氧化白藜芦醇的全合成中。以价廉易得的3,5-二甲氧基苄醇、2,4-二甲氧基苯甲醛为原料,经溴代、Arbuzov重排反应及Wittig-Horner反应得到2,3′,4,5′-四甲氧基二苯乙烯中间体,最后该中间体在AlCl3作用下进行脱甲基反应,成功制备了目标产物氧化白藜芦醇。改进后的合成工艺步骤短、反应条件温和、操作便捷、产率较高。所合成的化合物通过熔点、红外光谱、质谱以及核磁共振仪确认结构。以维生素C、2,6-二丁基对甲酚(butylated hydroxytoluene, BHT)和特丁基对苯二酚(tert-butyl hydroquinone, TBHQ)为参照,通过ABTS阳离子自由基清除能力、DPPH自由基清除能力和铁离子还原能力讨论了氧化白藜芦醇的抗氧化活性,并与白皮杉醇、白藜芦醇、茶多酚作比较。结果表明,氧化白藜芦醇的ABTS阳离子自由基清除能力远大于维生素C、BHT、TBHQ,其DPPH自由基清除能力以及铁离子还原能力均强于白藜芦醇和BHT,抗氧化性良好。研究结果可促进氧化白藜芦醇在食品添加剂中的应用。

关键词： 氧化白藜芦醇; Wittig-Horner反应; 合成; 脱甲基; 抗氧化活性

本文引用格式

陈莹 , 周华 , 晏日安 . 氧化白藜芦醇的合成工艺改进及其抗氧化活性[J]. 食品与发酵工业, 2023 , 49(19) : 152 -159 . DOI: 10.13995/j.cnki.11-1802/ts.033022

Abstract

The Wittig-Horner method used to prepare E-type olefins was applied in the total synthesis of oxyresveratrol. 2,3′,4,5′-tetramethoxystilbene intermediate was synthesized with cheap and easily available 3,5-dimethoxybenzyl alcohol and 2,4-dimethoxybenzaldehyde via bromination, Arbuzov rearrangement reaction, and Wittig-Horner reaction. Finally, the intermediate was demethylated with the help of aluminium trichloride, and then the target product oxyresveratrol was successfully prepared. The improved synthesis process had short synthetic steps, mild reaction conditions, easy operating processes, and a high yield. The structure of the final product was identified by melting point, infrared spectroscopy, mass spectrometry and nuclear magnetic resonance. The antioxidant activity of oxyresveratrol was discussed by ABTS radical scavenging activity,DPPH free radical, and ferric reducing antioxidant power with reference to vitamin C, butylated hydroxytoluene (BHT), and tert-butyl hydroquinone (TBHQ), and compared with piceatannol, resveratrol, and tea polyphenols for comparison. Results showed that oxyresveratrol had higher ABTS cation radical scavenging rate than that of vitamin C, BHT, and TBHQ, while its DPPH radical scavenging rate and ferric reducing antioxidant power were higher than that of resveratrol and BHT, showing excellent antioxidant power. These results will promote their application in food additives.

Key words： oxyresveratrol; Wittig-Horner reaction; synthesis; demethylation; antioxidant activity

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