新型水溶性没食子酸衍生物的合成及其对冷藏南美白对虾的抗氧化保鲜性能  

Synthesis and Antioxidant Activity of a Novel Water-Soluble Gallic Acid Derivative and Its Effect on Preserving Refrigerated Litopenaeus vannamei

作　　者：焦龙 冯慧珍 赵淑怡 倪继龙 张晓晔 张宾 JIAO Long;FENG Huizhen;ZHAO Shuyi;NI Jilong;ZHANG Xiaoye;ZHANG Bin(Key Laboratory of Health Risk Factors for Seafood of Zhejiang Province,College of Food Science and Pharmacy,Zhejiang Ocean University,Zhoushan 316022,China;Pisa Marine Graduate School,Zhejiang Ocean University,Zhoushan 316022,China;School of Naval Architecture and Maritime,Zhejiang Ocean University,Zhoushan 316022,China)

机构地区：[1]浙江海洋大学食品与药学学院,浙江省海产品健康危害因素关键技术研究重点实验室,浙江舟山316022 [2]浙江海洋大学比萨海洋研究生学院,浙江舟山316022 [3]浙江海洋大学船舶与海运学院,浙江舟山316022

出　　处：《食品科学》2024年第18期197-206,共10页Food Science

基　　金：浙江省基础公益研究计划项目(LQ22C200011);“十四五”国家重点研发计划重点专项(2021YFD2100504)。

摘　　要：为解决没食子酸(gallic acid,GA)因水溶性差而导致其对水产品抗氧化保鲜效果差的难题,本研究合成一种新型水溶性GA衍生物GA-CONH-SO_(3)H,通过高分辨质谱、核磁和光谱表征证实衍生物成功合成。非共价相互作用理论计算表明,GA-CONH-SO_(3)H与水分子间存在丰富的氢键作用,并与水分子的结合能强于GA。经测量,GA-CONH-SO_(3)H常温水中饱和溶解度为290.02 mg/mL,是GA的26倍。并且,GA-CONH-SO_(3)H对1,1-二苯基-2-苦肼基自由基、羟自由基和O_(2)^(-)·的清除率分别高达92.80%(58.78μmol/L GA仅为89.77%)、98.09%(1.76 mmol/L GA仅为49.56%)、99.74%(23.51 mmol/L GA仅为29.89%)。最后,在南美白对虾(Litopenaeus vannamei)4℃冷藏保鲜实验中,冷藏8 d后GA-CONH-SO_(3)H浸泡处理组虾肉pH值为7.44(GA组7.71),冷藏6 d后总挥发性盐基氮含量为27.07 mg/100 g(GA组35.47 mg/100 g)、硫代巴比妥酸反应物值为0.87 mg/kg(GA组0.94 mg/kg)、菌落总数为(5.09±0.02)(lg(CFU/g))(GA组(5.66±0.03)(lg(CFU/g))),GA-CONH-SO_(3)H保鲜效果显著,可延长其货架期2 d。此外,与商品化鲜虾保鲜剂4-己基间苯二酚(4-hexylresorcinol,4-HR)的对比实验结果表明,GA-CONH-SO_(3)H在抑制TVB-N、TBARS和TVC值增长方面效果均显著优于4-HR。同时,GA-CONH-SO_(3)H具有较低的细胞毒性。因此,GA-CONH-SO_(3)H是一种极具开发潜力的水产品抗氧化保鲜剂。To address the issue of the poor antioxidant and preservative effects of gallic acid(GA)on the quality of aquatic products due to its poor water solubility,a novel water-soluble GA derivative GA-CONH-SO_(3)H was successfully synthesized and confirmed by high resolution mass spectrometry(HRMS),nuclear magnetic resonance(NMR),and spectroscopy.Theoretical calculations of non-covalent interactions(NCI)revealed that GA-CONH-SO_(3)H exhibited abundant hydrogen bonding to water molecules,with binding energy stronger that than of GA.Moreover,the measured saturation solubility of GA-CONH-SO_(3)H in water at room temperature was 290.02 mg/mL,which was 26-fold higher than that of GA.Meanwhile,the 1,1-diphenyl-2-picrylhydrazyl(DPPH),hydroxy,and superoxide anion radical scavenging capacities of GA-CONH-SO_(3)H were 92.80%,98.09%and 99.74%,while those of GA at 58.78μmol/L,1.76 mmol/L and 23.51 mmol/L were only 89.77%,49.56%and 29.89%,respectively.After 8 days of storage at 4℃,the pH of shrimp(Litopenaeus vannamei)soaked in GA-CONH-SO_(3)H solution was 7.44 compared to 7.71 with GA,and after 6 days,the total volatile basic nitrogen(TVB-N)content,thiobarbituric acid reactive substances(TBARS)value were total viable count(TVC)were 27.07 mg/100 g,0.87 mg/kg and(5.09±0.02)(lg(CFU/g))as opposed to 35.47 mg/100 g,0.94 mg/kg and(5.66±0.03)(lg(CFU/g))with GA,which indicated that the preservative effect of GA-CONH-SO_(3)H was significant.It extended the shelf life by 2 days.Additionally,GA-CONH-SO_(3)H was significantly superior to 4-hexylresorcinol(4-HR)as a commercial fresh shrimp preservative in inhibiting the increase of TVB-N,TBARS and TVC values.Furthermore,GA-CONH-SO_(3)H exhibited very low cytotoxicity.Therefore,GA-CONH-SO_(3)H has great potential as an antioxidant preservative for aquatic products.

关 键 词：没食子酸衍生物 水溶性 抗氧化活性 南美白对虾 冷藏保鲜 

分 类 号：TS254.4[轻工技术与工程—水产品加工及贮藏工程]