海藻酸钠没食子酸衍生物的制备及性能分析
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摘要
以抗坏血酸和过氧化氢为自由基引发剂,使没食子酸与海藻酸钠接枝,赋予海藻酸钠抗氧化性、抑菌性等新的特性。结果表明:当添加过氧化氢和抗坏血酸5.54mmol(摩尔比3.51.0)时,接枝度最高为4.260mg/g。衍生物的红外和拉曼光谱证实了没食子酸成功接枝到海藻酸钠上;差示扫描量热分析发现衍生物的热稳定性改变,扫描电子显微镜分析显示该衍生物表面变得粗糙。当海藻酸钠—没食子酸衍生物浓度为4mg/mL时,对1,1-二苯基-2-三硝基苯肼自由基的清除率达到92.0%,远高于海藻酸钠的清除率,表明衍生物的抗氧化活性显著提高。相比海藻酸钠,该衍生物对车厘子的涂膜保鲜效果更好。
Ascorbic acid and hydrogen peroxide were used as free radical initiators to induce the grafting of gallic acid onto sodium alginate,in order to enhance new properties of sodium alginate such as antioxidation and bacteriostasis,so that it could have potential in food preservation application.Folin-Ciocalteu method was used for determining the grafting degree of sodium alginategallic acid derivative.The results showed that the highest grafting degree was 4.260 mg/g when 5.54 mmol of hydrogen peroxide and ascorbic acid(molar ratio 3.51.0)was added.Infrared and Raman analysis showed that new peaks were appeared in the spectra of the derivative,indicating that gallic acid was successfully grafted onto sodium alginate.Differential scanning calorimetry showed that the thermal stability of the grafted sodium alginate was changed,and scanning electron microscopy showed that the surface of the derivative became rough.When sodium alginate-gallic acid derivative concentration was 4 mg/mL,the scavenging rate of scavenging 1,1-diphenyl-2-trinitrophenylhydrazine radical was 92.0%,which was close to that of gallic acid,far higher than that of sodium alginate.The results showed that the antioxidant activity of the sodium alginate-gallic acid derivative increased significantly.Better preservation of cherries was obtained by the coating of sodium alginate-gallic acid derivative than by the coating of sodium alginate.
Ascorbic acid and hydrogen peroxide were used as free radical initiators to induce the grafting of gallic acid onto sodium alginate,in order to enhance new properties of sodium alginate such as antioxidation and bacteriostasis,so that it could have potential in food preservation application.Folin-Ciocalteu method was used for determining the grafting degree of sodium alginategallic acid derivative.The results showed that the highest grafting degree was 4.260 mg/g when 5.54 mmol of hydrogen peroxide and ascorbic acid(molar ratio 3.51.0)was added.Infrared and Raman analysis showed that new peaks were appeared in the spectra of the derivative,indicating that gallic acid was successfully grafted onto sodium alginate.Differential scanning calorimetry showed that the thermal stability of the grafted sodium alginate was changed,and scanning electron microscopy showed that the surface of the derivative became rough.When sodium alginate-gallic acid derivative concentration was 4 mg/mL,the scavenging rate of scavenging 1,1-diphenyl-2-trinitrophenylhydrazine radical was 92.0%,which was close to that of gallic acid,far higher than that of sodium alginate.The results showed that the antioxidant activity of the sodium alginate-gallic acid derivative increased significantly.Better preservation of cherries was obtained by the coating of sodium alginate-gallic acid derivative than by the coating of sodium alginate.
引文
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[28]吴昊,王艺颖,甄天元,等.壳聚糖没食子酸衍生物酶法催化条件优化及抗氧化活性和细胞毒性[J].食品科学,2017,38(2):227-232.
[29]赵珊,贡汉生,田亚晨,等.苯乳酸-海藻酸钠涂膜保鲜剂的制备及其在甜樱桃保鲜中的应用[J].食品科学,2018,39(11):221-226.
[2]OMS-OLIU G,SOLIVA-FORTUNY R,MARTIN-BEL-LOSO O.Using polysaccharide-based edible coatings to enhance quality and antioxidant properties of fresh-cut melon[J].LWT-Food Science and Technology,2008,41(10):1 862-1 870.
[3]KUMAR J N,PANG V Y T,AIK S X L.Calcium triggered self-assembly of alginate-graft-POEGMA via RAFT for the encapsulation of lipophillic actives[J].Journal of Materials Chemistry B,2017,5:8 254-8 263.
[4]OROIAN M,ESCRICHE I.Antioxidants:characterization,natural sources,extraction and analysis[J].Food Research International,2015,74:10-36.
[5]KRISHNAMOORTHY G,SELVAKUMAR R,SASTRY TP,et al.Experimental and theoretical studies on gallic acid assisted EDC/NHS initiated crosslinked collagen scaffolds[J].Materials Science&Engineering C,2014,43:164-171.
[6]HU Qiao-bin,LUO Yang-chao.Polyphenol-chitosan conjugates:synthesis,characterization,and applications[J].Carbohydrate Polymers,2016,151:624-639.
[7]ASGAR M A.Anti-diabetic potential of phenolic compounds:a review[J].International Journal of Food Properties,2013,16(1):91-103.
[8]ROLEIRA F M,TAVARES-DA-SILVA E J,VARELA CL,et al.Plant derived and dietary phenolic antioxidants:anticancer properties[J].Food Chemistry,2015,183:235-258.
[9]AYTEKIN A O,MORIMURA S,KIDA K.Synthesis of chitosan-caffeic acid derivatives and evaluation of their antioxidant activities[J].Journal of Bioscience&Bioengineering,2011,111(2):212-216.
[10]WORANUCH S,YOKSAN R.Preparation,characterization and antioxidant property of water-soluble ferulic acid grafted chitosan[J].Carbohydrate Polymers,2013,96(2):495-502.
[11]SPIZZIRRI U G,PARISI O I,IEMMA F,et al.Antioxidant-polysaccharide conjugates for food application by ecofriendly grafting procedure[J].Carbohydrate Polymers,2010,79(2):333-340.
[12]吴昊,甄天元,陈存坤,等.壳聚糖没食子酸衍生物酶法制备及对鲜切苹果的保鲜效果[J].农业工程学报,2017,33(4):285-292.
[13]吴春华.壳聚糖衍生物分子修饰机理及其在银鲳鱼保鲜中的应用研究[D].杭州:浙江大学,2017:54-71.
[14]HU Qiao-bin,WANG Tao-ran,ZHOU Ming-yong,et al.In vitro antioxidant-activity evaluation of gallic acid grafted chitosan conjugate synthesized by free radical induced grafting method[J].J Agric Food Chem,2016,64(29):5 893-5 900.
[15]GUO Ping,ANDERSSON J D,BOZELL J J,et al.The effect of solvent composition on grafting gallic acid onto chitosan via carbodiimide[J].Carbohydrate Polymers,2016,140:171-180.
[16]XIE Min-hao,HU Bing,WANG Yan,et al.Grafting of gallic acid onto chitosan enhances antioxidant activities and alters rheological properties of the copolymer[J].Journal of Agricultural&Food Chemistry,2014,62(37):9 128-9 136.
[17]ARIZMENDICOTERO D,GOMEZESPINOSA R M,DU-BLAN G O,et al.Electron paramagnetic resonance study of hydrogen peroxide/ascorbic acid ratio as initiator redox pair in the inulin-gallic acid molecular grafting reaction[J].Carbohydrate Polymers,2016,136:350-357.
[18]LIU Jun,LU Jian-feng,KAN Juan,et al.Synthesis of chitosan-gallic acid conjugate:structure characterization and in vitro anti-diabetic potential[J].International Journal of Biological Macromolecules,2013,62(11):321-329.
[19]LIU Jun,MENG Cheng-guang,YAN Ye-hua,et al.Protocatechuic acid grafted onto chitosan:characterization and antioxidant activity[J].International Journal of Biological Macromolecules,2016,89(1):518-526.
[20]ARIZMENDICOTERO D,VILANUEVA-CARVAJAL A,GOMEZESPINOSA R M,et al.Radical scavenging activity of an inulin-gallic acid graft and its prebiotic effect on Lactobacillus acidophilus in vitro growth[J].Journal of Functional Foods,2017,29:135-142.
[21]LI Jing-lei,SU Y K,CHEN Xi-guang,et al.Calcium-alginate beads loaded with gallic acid:preparation and characterization[J].LWT-Food Science and Technology,2016,68(132):667-673.
[22]CHENG Yi,LUO Xiao-long,BETZ J,et al.Mechanism of anodic electrodeposition of calcium alginate[J].Soft Matter,2011,7(12):5 677-5 684.
[23]CAMPOS-VALLETTE M M,CHANDIA N P,CLABIJIOE,et al.Characterization of sodium alginate and its block fractions by surface-enhanced Raman spectroscopy[J].Journal of Raman Spectroscopy,2010,41(7):758-763.
[24]POMPEU D R,LARONDELLE Y,ROGEZ H,et al.Characterization and discrimination of phenolic compounds using Fourier transform Raman spectroscopy and chemometric tools[J].Biotechnology Agronomy&Society&Environment,2018,22(1):13-28.
[25]CADILLA C L,HARP J,FLANAGAN J M,et al.Preparation and characterization of microcapsules of Pterodon pubescens Benth.By using natural polymers[J].Brazilian Journal of Pharmaceutical Science,2014,50(4):919-930.
[26]GONIL P,SAJOMSANG W,RUKTANONCHAI U R,et al.Novel quaternized chitosan containingβ-cyclodextrin moiety:synthesis,characterization and antimicrobial activity[J].Carbohydrate Polymers,2011,83(2):905-913.
[27]PASANPHAN W,BUETTNER G R,CHIRACHANCH-AI S.Chitosan gallate as a novel potential polysaccharide antioxidant:an EPR study[J].Carbohydrate Research,2010,345(1):132-140.
[28]吴昊,王艺颖,甄天元,等.壳聚糖没食子酸衍生物酶法催化条件优化及抗氧化活性和细胞毒性[J].食品科学,2017,38(2):227-232.
[29]赵珊,贡汉生,田亚晨,等.苯乳酸-海藻酸钠涂膜保鲜剂的制备及其在甜樱桃保鲜中的应用[J].食品科学,2018,39(11):221-226.