食品科学

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酰基稳态化花色苷及其热降解特性和抗氧化活性

滕慧1,米亚妮2,何远菊3,邓宏挺3,艾超4,陈雷3   

  1. 1. 广东海洋大学
    2. 福建农林大学
    3. 广东海洋大学食品科技学院
    4. 华南理工大学食品科学与工程学院
  • 收稿日期:2022-07-05 修回日期:2022-09-06 出版日期:2022-09-27 发布日期:2022-09-27
  • 通讯作者: 陈雷
  • 基金资助:
    广东省自科学基金

Acylation of anthocyanins: their thermal degradation characteristics and antioxidant activity

Hui TENGMI Yani2, 2, 2,Chao AI2,   

  • Received:2022-07-05 Revised:2022-09-06 Online:2022-09-27 Published:2022-09-27

摘要: 花色苷是植物中存在最广泛的天然色素,具有优良的抗氧化性,但其稳定性较差且生物利用度不高,酰基化修饰有利于提高其稳定性和生物利用度并扩展应用范围。食品级的肉桂酸甲酯为酰基供体,运用减压酶法,催化其与矢车菊素-3-O-葡萄糖苷(C3G)发生酰化反应,具有绿色安全,高效且酰化产物单一等优点。再对酰基化产物进行分离,并进行热稳定性和抗氧化性等性质的测定;结果表明,酰化转化率为80%,利用半制备高效液相仪对酰化后的产物进行分离纯化,得到纯化后的酰化C3G纯度达98.3%,经由MS分析可知酰化后产物为矢车菊素-3-(6-肉桂酰)-葡萄糖苷(C3(6C)G)。酰基化修饰使花色苷的脂溶性、热稳定性得到了很大的改善。用DPPH、ABTS、FRAP、羟自由基体外抗氧化实验测定不同浓度下C3G、C3(6C)G和维生素C的自由基清除能力。与同浓度的维生素C相比,除了在ABTS自由基清除实验中抗氧化表现不佳,C3G和C3(6C)G在其余三种抗氧化实验中表现良好。与C3G相比,酰基化产物C3(6C)G的羟自由基清除能力显著增强(p<0.05),在DPPH、ABTS、FRAP实验中,抗氧化能力差异不显著(p>0.05),这表明花色苷被肉桂酰修饰后并没有牺牲其抗氧化性能,而在对羟自由基的还原能力上显著提高。

关键词: 酰基化, 花色苷, 矢车菊素-3-O-葡萄糖苷, 肉桂酸甲酯, 脂肪酶

Abstract: Anthocyanins are the most widespread natural pigments in plants, with excellent antioxidant properties, but the poor stability and low bioavailability limit their applications. Acylation modification is beneficial to improve the stability and bioavailability of anthocyanins. The present study employed methyl cinnamate of food-grade to react with centainin-3-O-glucoside (C3G) by the decompression enzyme method, which has the advantages of green safety, high efficiency and single acylation product. Then the acylated products were separated and their thermal stability and antioxidant properties were determined. The results showed that conversion rate for the acylation was 80%. The semi-preparative HPLC was used to separate and purify the acylation product, and the purity of acylated product reached 98.3%. By MS analysis, the acylation product was found to be centathrin-3 - (6-cinnamyl) -glucoside (C3(6C)G). The lipid solubility and thermal stability of anthocyanins were improved by acylation. The free radical scavenging abilities of C3G, C3(6C)G and vitamin C were determined by DPPH, ABTS, FRAP and hydroxyl radical antioxidant experiments in vitro. Compared with vitamin C at the same concentration, C3G and C3(6C)G performed well in the other three antioxidant tests except for ABTS free radical scavenging test. Compared with C3G, the hydroxyl radical scavenging ability of the acylated product C3(6C)G was significantly enhanced (P < 0.05), and there was no significant difference in antioxidant ability in DPPH, ABTS and FRAP experiments (P > 0.05), suggesting that the antioxidant ability of anthocyanins was not sacrificed after modification with cinnamyl, but the reduction ability of hydroxyl radical was significantly improved.

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