食品科学 ›› 2023, Vol. 44 ›› Issue (6): 49-56.doi: 10.7506/spkx1002-6630-20220705-044

• 食品化学 • 上一篇    下一篇

酰基稳态化花色苷的制备及其热降解特性和抗氧化活性

滕慧,米亚妮,何远菊,邓宏挺,艾超,陈雷   

  1. (1.广东海洋大学食品科技学院,广东省水产品加工与安全重点实验室,广东省海洋生物制品工程实验室,广东省海洋食品工程技术研究中心,水产品深加工广东普通高等学校重点实验室,广东 湛江 534088;2.大连工业大学 海洋食品精深加工关键技术省部共建协同创新中心,辽宁 大连 116034;3.福建农林大学食品科学学院,福建 福州 350002)
  • 出版日期:2023-03-27 发布日期:2023-03-27
  • 基金资助:
    广东省自然科学基金面上项目(2022A1515010694);广东海洋大学科研启动经费资助项目(101202/060302042103); 中国博士后面上基金项目(2020M682073)

Preparation of Acylated Anthocyanin and Its Thermal Degradation Properties and Antioxidant Activity

TENG Hui, MI Yani, HE Yuanju, DENG Hongting, AI Chao, CHEN Lei   

  1. (1. Guangdong Provincial Key Laboratory of Aquatic Product Processing and Safety, Guangdong Province Engineering Laboratory for marine Biological Products, Guangdong Provincial Engineering Technology Research Center of Seafood, Key Laboratory of Advanced Processing of Aquatic Product of Guangdong Higher Education Institution, College of Food Science and Technology, Guangdong Ocean University, Zhanjiang 524088, China; 2. Collaborative Innovation Center of Seafood Deep Processing, Dalian Polytechnic University, Dalian 116034, China; 3. College of Food Science, Fujian Agriculture and Forestry University, Fuzhou 350002, China)
  • Online:2023-03-27 Published:2023-03-27

摘要: 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。对酰化产物进行分离,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色谱仪对酰化后的产物进行分离纯化,纯化后的酰化C3G纯度达98.3%;经质谱分析可知,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、热稳定性得到了明显改善。采用1,1-二苯基-2-三硝基苯肼(1,1-diphenyl-2-picrylhydrazyl,DPPH)自由基清除、2,2-氨基-二(3-乙基-苯并噻唑啉-6-磺酸)(2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid,ABTS)阳离子自由基清除、铁离子还原/抗氧化能力法(ferric reducing and antioxidant power,FRAP)、羟自由基清除体外实验测定不同浓度下C3G、C3(6C)G和VC的抗氧化能力。与相同浓度的VC相比,除了在ABTS阳离子自由基清除实验中抗氧化表现不佳,C3G和C3(6C)G在其余3 种抗氧化实验中表现良好。浓度为200 μmol/L时,与C3G相比,酰化产物C3(6C)G的羟自由基和DPPH自由基清除能力显著增强(P<0.05);此浓度下,C3G和C3(6C)G的ABTS阳离子自由基清除和FRAP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减弱其抗氧化性能,而对羟自由基的清除能力上显著提高。

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: Food-grade methyl cinnamate as an acyl donor was used to enzymatically acylate cyanidin-3-O-glucoside (C3G) under reduced pressure, which has the advantages of safety, high efficiency and single acylation product. After being purified by semi-preparative high-performance liquid chromatography (SP-HPLC), the acylation product was evaluated for its thermal stability and antioxidant activity. The results showed that the acylation rate was 80%, and the purity of the purified acylated C3G was as high as 98.3%. Mass spectral analysis showed that the acylated product was cyanidin-3-(6-cinnamoyl)-glucoside (C3(6C)G). Acylation modification significantly improved the lipid solubility and thermal stability of C3G. C3G and C3(6C)G had weaker scavenging capacity against 2,2-amino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical cation but similar 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging capacity, ferric reducing and antioxidant power (FRAP) and hydroxyl radical scavenging capacity compared with vitamin C (VC) at the same concentration. At 200 μmol/L, the hydroxyl and DPPH radical scavenging capacity of C3(6C)G was significantly enhanced compared with C3G (P < 0.05), while there was no significant difference in ABTS radical cation scavenging or FRAP between C3G and C3(6C)G (P > 0.05), which showed that cinnamyl modification did not impair the antioxidant capacity of anthocyanins, but instead improved the scavenging capacity against hydroxyl radicals.

Key words: acylation; anthocyanin; centaulin-3-O-glucoside; methyl cinnamate; lipase

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