壳寡糖的制备及应用的研究进展Research Progress of Preparation and Application of Chitooligosaccharides
张沛尧,赵宁,席军,单艳琴,何旭东,于海
摘要(Abstract):
甲壳质是自然界中分布广泛、产量很高的一种多糖,但是其内外氢键之间存在相互作用力,进而组成了有序的大分子结构,导致其在常用的溶剂中的溶解性受到抑制。它的脱乙酰基产物为壳聚糖,壳聚糖的水溶性仍然没有得到很好的改善。而壳寡糖是壳聚糖糖苷键经改性断裂后降解得到的寡糖产品,在改善难溶的物理特性的同时,也使其拥有了多种更高的生物活性,如抗氧化、抑菌、抗炎、抗肿瘤、促进作物生长等功能。文章综述了制备壳寡糖的几种方法并且比较了它们的优缺点,讨论了它们在食品等领域中的具体应用,最后尝试对不同相对分子质量、具有不同特性的壳寡糖在各个领域的应用进行了总结。
关键词(KeyWords): 壳寡糖;制备方法;应用;相对分子质量;抗氧化
基金项目(Foundation): 江苏省科技厅重点研发项目(BE2022333)
作者(Author): 张沛尧,赵宁,席军,单艳琴,何旭东,于海
参考文献(References):
- [1]RINAUDO M.Chitin and chitosan:properties and applications[J].Progress in Polymer Science,2006,31(7):603-632.
- [2]NAVEED M,PHIL L,SOHAIL M,et al.Chitosan oligosaccharide (COS):an overview[J].International Journal of Biological Macromolecules,2019,129:827-843.
- [3]VONGCHAN P,WUTTIIN Y,SAJOMSANG W,et al.N,N,N-Trimethyl chitosan nanoparticles for the delivery of monoclonal antibodies against hepatocellular carcinoma cells[J].Carbohydrate Polymers,2011,85(1):215-220.
- [4]汤薇,董静,赵金荣,等.壳聚糖改性及改性壳聚糖应用研究进展[J].济南大学学报(自然科学版),2023,37(1):84-93.
- [5]DANG Y B,LI S,WANG W X,et al.The effects of chitosan oligosaccharide on the activation of murine spleen CD11c+ dendritic cells via Toll-like receptor 4[J].Carbohydrate Polymers,2011,83(3):1075-1081.
- [6]杨靖亚,郑雯静,李诗怡.壳寡糖的制备及生物活性研究进展[J].国际药学研究杂志,2020,47(7):502-507.
- [7]GUAN Z W,FENG Q.Chitosan and chitooligosaccharide:the promising non-plant-derived prebiotics with multiple biological activities[J].International Journal of Molecular Sciences,2022,23(12):6761.
- [8]BARKER S A,FOSTER A B,STACEY M,et al.451.Amino-sugars and related compounds.Part Ⅳ.Isolation and properties of oligosaccharides obtained by controlled fragmentation of chitin[J].Journal of the Chemical Society (Resumed),1958:2218-2227.
- [9]刘晓,石瑛,白雪芳,等.甲壳低聚糖的酸水解[J].中国水产科学,2003(1):69-72.
- [10]GONCALVES C,FERREIRA N,LOURENCO L.Production of low molecular weight chitosan and chitooligosaccharides (COS):a review[J].Polymers,2021,13(15):2466.
- [11]吴丽华,周萌,郑必胜,等.壳聚糖氧化降解制备聚合度6以下的壳寡糖[J].现代食品科技,2017,33(9):140-146,55.
- [12]邵健,杨宇民,姚成.低聚氨基葡萄糖的吸湿、保湿和抑菌性质[J].中国海洋药物,2000(4):25-27.
- [13]董岸杰,张晓丽,李军,等.超声波在壳聚糖降解反应中的作用[J].高分子材料科学与工程,2002(6):187-189.
- [14]李大鹏,王莹,刘伟,等.超声波降解法制备低聚壳聚糖工艺及其抗菌作用研究[J].农产品加工(学刊),2013(13):10-12.
- [15]周苗苗.微波辅助降解壳聚糖的研究[D].青岛:中国科学院研究生院(海洋研究所),2015.
- [16]张金豫.不同原料壳寡糖的制备及抑菌活性研究[D].天津:天津科技大学,2018.
- [17]HAI L,DIEP T B,NAGASAWA N,et al.Radiation depolymerization of chitosan to prepare oligomers[J].Nuclear Instruments and Methods in Physics Research Section B:Beam Interactions with Materials and Atoms,2003,208(1):466-470.
- [18]TABASSUM N,AHMED S,ALI M A.Chitooligosaccharides and their structural-functional effect on hydrogels:a review[J].Carbohydrate Polymers,2021,261(5):117882.
- [19]CHOI W S,AHN K J,LEE D W,et al.Preparation of chitosan oligomers by irradiation[J].Polymer Degradation and Stability,2002,78(3):533-538.
- [20]李振达.壳寡糖的制备及其在水产养殖上的应用研究[D].舟山:浙江海洋大学,2011.
- [21]梁慧培,覃小丽,钟金锋.壳寡糖制备和生理活性的研究进展[J].食品工业科技,2016,37(3):384-388.
- [22]赵华,樊龙星,张朝正.响应面法优化组成型壳聚糖酶酶解条件[J].中国酿造,2020,39(1):165-169.
- [23]CHEN Y L,LING Z M,MAMTIMIN T,et al.Chitooligosaccharides production from shrimp chaff in chitosanase cell surface display system[J].Carbohydrate Polymers,2022,277:118894.
- [24]季珂,李恒,龚劲松,等.酶法制备壳寡糖及其抗肿瘤活性评价[J].食品与生物技术学报,2021,40(6):93-99.
- [25]黄晓月,毕思远,区家豪,等.木瓜蛋白酶法制备抗氧化活性壳寡糖的工艺优化[J].生物学杂志,2022,39(1):104-109.
- [26]汪金秀,李丹丹,柏韵,等.微波-酶法制备壳寡糖工艺优化[J].饲料研究,2018(2):62-64,70.
- [27]GUAN F F,HAN Y S,YAN K,et al.Highly efficient production of chitooligosaccharides by enzymes mined directly from the marine metagenome[J].Carbohydrate Polymers,2020,234(2):115909.
- [28]EL-SAYED W N,ALKABLI J,ALOQBI A,et al.Optimization enzymatic degradation of chitosan into amphiphilic chitooligosaccharides for application in mitigating liver steatosis and cholesterol regulation[J].European Polymer Journal,2021,153(7):110507.
- [29]朱玉霞.壳寡糖的制备、分离分析及抑菌活性研究[D].无锡:江南大学,2013.
- [30]王鲁霞,吴延立,马文平.壳寡糖的制备方法及其在食品中的应用现状[J].安徽农业科学,2014,42(32):11485-11487.
- [31]MITTAL A,SINGH A,BUATONG J,et al.Chitooligosaccharide and its derivatives:potential candidates as food additives and bioactive components[J].Foods,2023,12(20):3854.
- [32]SINGH A,BENJAKUL S,ZHOU P,et al.Effect of squid pen chitooligosaccharide and epigallocatechin gallate on discoloration and shelf-life of yellow fin tuna slices during refrigerated storage[J].Food Chemistry,2021,351(10):129296.
- [33]孟紫强,秦国华,张波,等.吸入二氧化硫对小鼠脑细胞DNA的损伤作用[J].中华预防医学杂志,2002(6):11-14.
- [34]郝振铭,孙珍.壳寡糖对葡萄酒的抗氧化和抑菌作用[J].现代食品科技,2019,35(12):216-224,60.
- [35]RU L,JIANG L,WILLS R B H,et al.Chitosan oligosaccharides induced chilling resistance in cucumber fruit and associated stimulation of antioxidant and HSP gene expression[J].Scientia Horticulturae,2020,264:109187.
- [36]朱玥.壳寡糖对饼干和蛋糕品质的影响[D].武汉:武汉轻工大学,2021.
- [37]ANIL S.Potential medical applications of chitooligosaccharides[J].Polymers,2022,14(17):3558.
- [38]NGO D N,LEE S H,KIM M M,et al.Production of chitin oligosaccharides with different molecular weights and their antioxidant effect in RAW 264.7 cells[J].Journal of Functional Foods,2009,1(2):188-198.
- [39]YANG Y M,SHU R G,SHAO J,et al.Radical scavenging activity of chitooligosaccharide with different molecular weights[J].European Food Research and Technology,2006,222(1):36-40.
- [40]MENDIS E,KIM M M,RAJAPAKSE N,et al.An in vitro cellular analysis of the radical scavenging efficacy of chitooligosaccharides[J].Life Sciences,2007,80(23):2118-2127.
- [41]龚魁杰,陈利容,祁国栋,等.ClO2杀菌复合壳寡糖涂膜对鲜食糯玉米的保鲜效果[J].食品科学,2018,39(21):279-284.
- [42]谷新晰,王晨笑,于宏伟,等.壳寡糖对泡菜品质、微生物多样及演替规律的影响[J].中国食品学报,2021,21(10):125-132.
- [43]MENG L Y,MA J Q,LIU C H,et al.The microbial stress responses of Escherichia coli and Staphylococcus aureus induced by chitooligosaccharide[J].Carbohydrate Polymers,2022,287(5):119325.
- [44]NO H K,PARK N Y,LEE S H,et al.Antibacterial activity of chitosans and chitosan oligomers with different molecular weights[J].International Journal of Food Microbiology,2002,74(1-2):65-72.
- [45]XIA W S,LIU P,ZHANG J L,et al.Biological activities of chitosan and chitooligosaccharides[J].Food Hydrocolloids,2011,25(2):170-179.
- [46]LIU Y L,XING R G,LIU S,et al.Effects of chitooligosaccharides supplementation with different dosages,molecular weights and degrees of deacetylation on growth performance,innate immunity and hepatopancreas morphology in Pacific white shrimp (Litopenaeus vannamei)[J].Carbohydrate Polymers,2019,226:115254.
- [47]XU Q,AZZAM M M M,ZOU X,et al.Effects of chitooligosaccharide supplementation on laying performance,egg quality,blood biochemistry,antioxidant capacity and immunity of laying hens during the late laying period[J].Italian Journal of Animal Science,2020,19(1):1180-1187.
- [48]THONGSONG B,SUTHONGSA S,PICHYANGKURA R,et al.Effects of chito-oligosaccharide supplementation with low or medium molecular weight and high degree of deacetylation on growth performance,nutrient digestibility and small intestinal morphology in weaned pigs[J].Livestock Science,2018,209:60-66.
- [49]MENG X,WANG J T,WAN W J,et al.Influence of low molecular weight chitooligosaccharides on growth performance and non-specific immune response in Nile tilapia Oreochromis niloticus[J].Aquaculture International,2017,25(3):1265-1277.
- [50]WALSH A M,SWEENEY T,BAHAR B,et al.The effect of chitooligosaccharide supplementation on intestinal morphology,selected microbial populations,volatile fatty acid concentrations and immune gene expression in the weaned pig[J].Animal,2012,6(10):1620-1626.
- [51]MAEDA Y,KIMURA Y.Antitumor effects of various low-molecular-weight chitosans are due to increased natural killer activity of intestinal intraepithelial lymphocytes in sarcoma 180-bearing mice[J].The Journal of Nutrition,2004,134(4):945-950.
- [52]SALAH R,MICHAUD P,MATI F,et al.Anticancer activity of chemically prepared shrimp low molecular weight chitin evaluation with the human monocyte leukaemia cell line,THP-1[J].International Journal of Biological Macromolecules,2013,52:333-339.
- [53]PARK J K,CHUNG M J,CHOI H A,et al.Effects of the molecular weight and the degree of deacetylation of chitosan oligosaccharides on antitumor activity[J].International Journal of Molecular Sciences,2011,12(1):266-277.
- [54]郭平强.酶法制备壳寡糖及其保健食品的功能研究[D].福州:福建师范大学,2018.
- [55]LU B S,CHEN X J,OUYANG X,et al.The roles of novel chitooligosaccharide-peanut oligopeptide carbon dots in improving the flavor quality of Chinese cabbage[J].Food Chemistry:X,2023,20(43):100963.
- [56]WANG H X,HU L D,DU J,et al.Development of rheologically stable high internal phase emulsions by gelatin/chitooligosaccharide mixtures and food application[J].Food Hydrocolloids,2021,121(12):107050.
- [57]郭蔓,赵华,张朝正.壳寡糖的制备及应用研究[J].中国食品添加剂,2022,33(10):267-271.
- [58]李雨新,李尚勇,陈雪红.壳寡糖的分析方法及其在种植业领域的应用[J].农村经济与科技,2020,31(8):78-80.
- [59]聂青玉.壳寡糖涂被纸包装对西兰花采后保鲜的影响[J].食品科技,2014,39(6):63-66.
- [60]魏夕雅,张丽丽,顾超珩,等.壳寡糖对番茄和韭菜中有机磷类农药降解的生理调控作用[J].植物生理学报,2020,56(2):285-293.
- [61]ZHANG X Q,LI K C,LIU S,et al.Size effects of chitooligomers on the growth and photosynthetic characteristics of wheat seedlings[J].Carbohydrate Polymers,2016,138:27-33.
- [62]王鲁霞,马文平,朱辉,等.壳寡糖的性能及其在化妆品中的应用[J].科技创新与应用,2014(27):16-17.
- [63]耿懂懂.酶解法制备壳寡糖工艺及其抑菌活性的研究[D].上海:上海应用技术大学,2020.