食品科学 ›› 2018, Vol. 39 ›› Issue (2): 240-246.doi: 10.7506/spkx1002-6630-201802038

• 工艺技术 • 上一篇    下一篇

去甲基化法制备黄豆苷元和染料木黄酮及抗氧化性分析

张晓松,金花,闫惠丽,张永忠,许晶*   

  1. (东北农业大学理学院,黑龙江?哈尔滨 150030)
  • 出版日期:2018-01-25 发布日期:2018-01-05
  • 作者简介:张晓松,金花,闫惠丽,张永忠,许晶
  • 基金资助:
    国家自然科学基金青年科学基金项目(31301600);中国博士后特别资助项目(2014T70306); 黑龙江省博士后启动基金项目(LBH-Q16012)

Preparation of Daidzein and Genistein by Demethylation Reaction and Their Antioxidant Activity

ZHANG Xiaosong, JIN Hua, YAN Huili, ZHANG Yongzhong, XU Jing*   

  1. (College of Science, Northeast Agricultural University, Harbin 150030, China)
  • Online:2018-01-25 Published:2018-01-05

摘要: 以KBr-H3PO4或KI-H3PO4为反应介质,对芒柄花黄素和鸡豆黄素进行去甲基化反应转化成黄豆苷元和染料木黄酮,并对产物的抗氧化性进行分析。结果表明:以KBr-H3PO4为反应介质,制备黄豆苷元最佳条件为反应时间5?h、反应温度120?℃、料液比1∶45(g/mL)、最佳饱和度75%,产率为89.42%;制备染料木黄酮最佳条件为反应时间5?h、反应温度120?℃、料液比1∶45(g/mL)、最佳饱和度100%,产率为85.98%;以KI-H3PO4为反应介质,制备黄豆苷元最佳条件为反应时间4?h、反应温度100?℃、料液比1∶15(g/mL)、最佳饱和度75%,产率可达87.03%;制备染料木黄酮最佳条件分别为反应时间5?h、反应温度100?℃和料液比1∶45(g/mL)、最佳饱和度75%,产率可达88.51%。与已有合成方法相比,本实验方法具有反应过程简单、反应条件温和、反应时间较短、产率较高等优点。所制备黄豆苷元和染料木黄酮具有一定的1,1-二苯基-2-三硝基苯肼自由基和羟自由基清除能力,以及较强的抗亚油酸氧化能力,表现出较好的抗氧化性。

关键词: 去甲基化, 黄豆苷元, 染料木黄酮, 芒柄花黄素, 鸡豆黄素

Abstract: Daidzein and genistein were derived from the demethylation of formononetin and biochanin A in KBr-H3PO4 or KI-H3PO4 solution, respectively. The antioxidant activities of daidzein and genistein were also evaluated. The optimal conditions for preparing daidzein in KBr-H3PO4 solution were determined as follows: reaction time 5 h, reaction temperature 120 ℃, ratio of solid to solvent 1:45 (g/mL), and degree of saturation 75%, providing maximum reaction yield of 89.42%, while those for preparing genistein were 5 h, 120 ℃, 1:45 (g/mL), and 100%, providing maximum reaction yield of 85.98%; the optimal conditions for preparing daidzein in KI-H3PO4 solution were determined as 4 h, 100 ℃, 1:15 (g/mL) and 75% for reaction time, temperature, ratio of solid to solvent and degree of saturation, respectively, providing maximum reaction yield of 87.03%, while those for preparing genistein were 5 h, 100 ℃, 1:45 (g/mL) and 75%, respectively, providing maximum reaction yield of 88.51%. Compared with the traditional synthesis methods, the proposed method in this study had many advantages such as simpler reaction process, milder reaction conditions, shorter reaction time and higher yield. The daidzein and genistein had 1,1-diphenyl-2-picryl-hydrazyl and hydroxyl radical scavenging ability and a potent inhibitory effect on linoleic acid oxidation suggesting good antioxidant activity.

Key words: demethylation, daidzein, genistein, formononetin, biochanin A

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