Research Progress on the Preparation, Purification and Application of Chitooligosaccharides

GUO Hanzhong; LI Yongsha; LI Yongcheng; XIA Guanghua; ZHANG Xueying

doi:10.13386/j.issn1002-0306.2023070123

Volume 45 Issue 10

May 2024

Turn off MathJax

Article Contents

Abstract

References

Supplements

Science and Technology of Food Industry > 2024 > 45(10): 412-422. > DOI: 10.13386/j.issn1002-0306.2023070123

GUO Hanzhong, LI Yongsha, LI Yongcheng, et al. Research Progress on the Preparation, Purification and Application of Chitooligosaccharides[J]. Science and Technology of Food Industry, 2024, 45(10): 412−422. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2023070123.

Citation:

PDF (1650 KB)

Research Progress on the Preparation, Purification and Application of Chitooligosaccharides

GUO Hanzhong^1,,
LI Yongsha¹,
LI Yongcheng^{1, 2},
XIA Guanghua^{1, 2},
ZHANG Xueying^{1, 2, ,}

1.
Hainan Engineering Research Center of Aquatic Resources Efficient Utilization in South China Sea, Key Laboratory of Seafood Processing of Haikou, National R&D Branch Center for Prawn Processing Technology (Haikou), College of Food Science and Technology, Hainan University, Haikou 570228, China
2.
Collaborative Innovation Center of Provincial and Ministerial Co-Construction for Marine Food Deep Processing,Dalian Polytechnic University, Dalian 116034, China

More Information

Received Date: July 16, 2023
Available Online: March 21, 2024

Graphical Abstract

Abstract

Abstract

Chitooligosaccharides (COS) is homo- or heterooligomers of N-acetylglucosamine and D-glucosamine obtained via degradation of chitin or chitosan. COS is useful for remarkably wide spectrum of applications in the pharmaceutical, food, and agricultural industries due in part to their antimicrobial, antioxidant, antitumor, and immunomodulatory activities. Enzymatic, physical, and chemical methods for the preparation of COS has been reported. At present, the preparation of COS by any single method faces limitations, including difficulty in obtaining target products with specific degrees of polymerization and acetylation. Therefore, COS preparation protocols have shifted from single method strategies to explorations of cooperative catalytic systems. COS purity can also be improved by incorporating separation and purification techniques including ultrafiltration, activated carbon adsorption, and chromatography. In this paper, progress in COS preparation and purification methods and COS applications are reviewed, with the objective of providing a theoretical basis for improved production and expansion of applications for high quality COS.
- chitin,
- chitosan,
- chitooligosaccharides,
- preparation,
- separation and purification,
- application

FullText(HTML)

References (110)

References

[1]	SCHMITZ C, AUZA L G, KOBERIDZE D, et al. Conversion of chitin to defined chitosan oligomers:Current status and future prospects[J]. Marine Drugs,2019,17(8):452. doi: 10.3390/md17080452
[2]	NOVIKOV V Y, RYSAKOVA K S, SHUMSKAYA N V, et al. King crab gills as a new source of chitin/chitosan and protein hydrolysates[J]. International Journal of Biological Macromolecules,2023,232:123346. doi: 10.1016/j.ijbiomac.2023.123346
[3]	KOU S G, PETERS L M, MUCALO M R. Chitosan:A review of sources and preparation methods[J]. International Journal of Biological Macromolecules,2021,169:85−94. doi: 10.1016/j.ijbiomac.2020.12.005
[4]	KUMAR M, BRAR A, VIVEKANAND V, et al. Bioconversion of chitin to bioactive chitooligosaccharides:Amelioration and coastal pollution reduction by microbial resources[J]. Marine Biotechnology,2018,20(3):269−281. doi: 10.1007/s10126-018-9812-x
[5]	刘梦琪, 吕瑞, 陈菊, 等. 壳聚糖的抗菌作用及在抑菌活性包装中的应用进展[J]. 食品科学,2024,45(1):261−271. [LIU M Q, LÜ R, CHEN J, et al. Antibacterial action of chitosan and its application in antibacterial active packaging[J]. Food Science,2024,45(1):261−271.] doi: 10.7506/spkx1002-6630-20230119-146 LIU M Q, LÜ R, CHEN J, et al. Antibacterial action of chitosan and its application in antibacterial active packaging[J]. Food Science, 2024, 45（1）: 261−271. doi: 10.7506/spkx1002-6630-20230119-146
[6]	周勇. 酶法脱乙酰化制备壳寡糖的研究进展[J]. 安徽农学通报, 2021, 27(11):27-31, 118. [ZHOU Y. Research progress of enzymatic deacetylation to make chitosan oligosaccharides[J]. Anhui Agricultural Science Bulletin, 2021, 27(11):27-31, 118.] ZHOU Y. Research progress of enzymatic deacetylation to make chitosan oligosaccharides[J]. Anhui Agricultural Science Bulletin, 2021, 27（11）: 27-31, 118.
[7]	KUMAR M, MADHUPRAKASH J, BALAN V, et al. Chemoenzymatic production of chitooligosaccharides employing ionic liquids and Thermomyces lanuginosus chitinase[J]. Bioresource Technology,2021,337:125399. doi: 10.1016/j.biortech.2021.125399
[8]	WANG Y Y, ZHAO K, LI L, et al. A review of the immune activity of chitooligosaccharides[J]. Food Science and Technology,2023,43:e97822. doi: 10.1590/fst.97822
[9]	LÜ J R, LÜ X H, MA M H, et al. Chitin and chitin-based biomaterials:A review of advances in processing and food applications[J]. Carbohydrate Polymers,2023,299:120142. doi: 10.1016/j.carbpol.2022.120142
[10]	KASPRZAK D, GALIŃSKI M. Chitin and chitin-cellulose composite hydrogels prepared by ionic liquid-based process as the novel electrolytes for electrochemical capacitors[J]. Journal of Solid State Electrochemistry,2021,25(10-11):2549−2563. doi: 10.1007/s10008-021-05036-3
[11]	TAOKAEW S, KRIANGKRAI W. Chitinase-assisted bioconversion of chitinous waste for development of value-added chito-oligosaccharides products[J]. Biology,2023,12(1):87. doi: 10.3390/biology12010087
[12]	LE B, YANG S H. Microbial chitinases:Properties, current state and biotechnological applications[J]. World Journal of Microbiology and Biotechnology,2019,35(9):144. doi: 10.1007/s11274-019-2721-y
[13]	CHAVAN S B, DESHPANDE M V. Chitinolytic enzymes:an appraisal as a product of commercial potential[J]. Biotechnology Progress,2013,29(4):833−846. doi: 10.1002/btpr.1732
[14]	COURTADE G, AACHMANN F L. Chitin-active lytic polysaccharide monooxygenases[J]. Advances in Experimental Medicine and Biology,2019,1142:115−129.
[15]	LE B, YANG S H. Characterization of a chitinase from Salinivibrio sp. BAO-1801 as an antifungal activity and a biocatalyst for producing chitobiose[J]. Journal of Basic Microbiology,2018,58(10):848−856. doi: 10.1002/jobm.201800256
[16]	WANG J R, ZHU M J, WANG P, et al. Biochemical properties of a cold-active chitinase from marine Trichoderma gamsii R1 and its application to preparation of chitin oligosaccharides[J]. Marine Drugs,2023,21(6):332. doi: 10.3390/md21060332
[17]	FU X, GUO X X, JIN Y G, et al. Bioconversion of chitin waste using a cold-adapted chitinase to produce chitin oligosaccharides[J]. LWT-Food Science and Technology,2020,133:109863. doi: 10.1016/j.lwt.2020.109863
[18]	THOMAS R, FUKAMIZO T, SUGINTA W. Bioeconomic production of high-quality chitobiose from chitin food wastes using an in-house chitinase from Vibrio campbellii[J]. Bioresources and Bioprocessing,2022,9(1):86. doi: 10.1186/s40643-022-00574-8
[19]	GAO L, SUN J A, SECUNDO F, et al. Cloning, characterization and substrate degradation mode of a novel chitinase from Streptomyces albolongus ATCC 27414[J]. Food Chemistry,2018,261:329−336. doi: 10.1016/j.foodchem.2018.04.068
[20]	DAHIYA N, TEWARI R, HOONDAL G S. Biotechnological aspects of chitinolytic enzymes:A review[J]. Applied Microbiology and Biotechnology,2006,71(6):773−782. doi: 10.1007/s00253-005-0183-7
[21]	SUZUKI K, SUGAWARA N, SUZUKI M, et al. Chitinases A, B, and C1 of Serratia marcescens 2170 produced by recombinant Escherichia coli:enzymatic properties and synergism on chitin degradation[J]. Bioscience, Biotechnology, and Biochemistry,2002,66(5):1075−1083. doi: 10.1271/bbb.66.1075
[22]	ZHANG Q, ZHANG X Y, HE Y C, et al. The synergistic action of two chitinases from Vibrio harveyi on chitin degradation[J]. Carbohydrate Polymers,2023,307:120640. doi: 10.1016/j.carbpol.2023.120640
[23]	XU P, WU X L, GUO X X, et al. Double-chitinase hydrolysis of crab shell chitin pretreated by ionic liquid to generate chito-oligosaccharide[J]. ACS Sustainable Chemistry and Engineering,2019,7(1):1683−1691. doi: 10.1021/acssuschemeng.8b05447
[24]	MUKHERJEE S, BEHERA P K, MADHUPRAKASH J. Efficient conversion of crystalline chitin to N-acetylglucosamine and N, N’-diacetylchitobiose by the enzyme cocktail produced by Paenibacillus sp. LS1[J]. Carbohydrate Polymers,2020,250:116889. doi: 10.1016/j.carbpol.2020.116889
[25]	谢杰, 李玉斌, 刘京伟, 等. 壳聚糖酶结构与功能的研究进展[J]. 生物工程学报,2023,39(3):912−929. [XIE J, LI Y B, LIU J W, et al. Advances in the structure and function of chitosanase[J]. Chinese Journal of Biotechnology,2023,39(3):912−929.] XIE J, LI Y B, LIU J W, et al. Advances in the structure and function of chitosanase[J]. Chinese Journal of Biotechnology, 2023, 39（3）: 912−929.
[26]	SUN H H, ZHAO L, MAO X Z, et al. Identification of a key loop for tuning transglycosylation activity in the substrate-binding region of a chitosanase[J]. Journal of Agricultural and Food Chemistry,2023,71(14):5585−5591. doi: 10.1021/acs.jafc.3c00110
[27]	曹世宁. 草酸青霉壳聚糖酶的酶学性质研究、分子克隆及食品级表达[D]. 无锡:江南大学, 2022. [CAO S N. Study on enzymatic properties, molecular cloning and food-grade expression of chitosanase from penicillium oxalicum[D]. Wuxi:Jiangnan University, 2022.] CAO S N. Study on enzymatic properties, molecular cloning and food-grade expression of chitosanase from penicillium oxalicum[D]. Wuxi: Jiangnan University, 2022.
[28]	PATANTIS G, ZILDA D S, FAWZYA Y N, et al. Purification of chitosanase from Stenotrophomonas maltophilia KPU 2123 and Micromonospora sp. T5a1 for chitooligosacharide production[J]. Iop Conference Series:Earth and Environmental Science,2020,404(1):12078. doi: 10.1088/1755-1315/404/1/012078
[29]	DOAN C T, TRAN T N, NGUYEN V B, et al. Bioprocessing of squid pens waste into chitosanase by Paenibacillus sp. TKU047 and its application in low-molecular weight chitosan oligosaccharides production[J]. Ploymers,2020,12(5):1163. doi: 10.3390/polym12051163
[30]	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. [ZHAO H, FAN L X, ZHANG C Z. Optimization of enzymatic hydrolysis conditions of compositional chitosanase by response surface methodology[J]. China Brewing,2020,39(1):165−169.] doi: 10.11882/j.issn.0254-5071.2020.01.032 ZHAO H, FAN L X, ZHANG C Z. Optimization of enzymatic hydrolysis conditions of compositional chitosanase by response surface methodology[J]. China Brewing, 2020, 39（1）: 165−169. doi: 10.11882/j.issn.0254-5071.2020.01.032
[31]	罗洒. 新型壳聚糖酶的髙效表达及壳寡糖制备工艺研究[D]. 上海:华东理工大学, 2019. [LUO S. High-level expression of novel chitosanase and preparation of chitooligosaccharides[D]. Shanghai:East China University of Science and Technology, 2019.] LUO S. High-level expression of novel chitosanase and preparation of chitooligosaccharides[D]. Shanghai: East China University of Science and Technology, 2019.
[32]	GUO X, AN Y J, JIANG L Y, et al. The discovery and enzymatic characterization of a novel AA10 LPMO from Bacillus amyloliquefaciens with dual substrate specificity[J]. International Journal of Biological Macromolecules,2022,203:457−465. doi: 10.1016/j.ijbiomac.2022.01.110
[33]	KUMAR M, RAJPUT M, SONI T, et al. Chemoenzymatic production and engineering of chitooligosaccharides and N-acetyl glucosamine for refining biological activities[J]. Frontiers in Chemistry,2020,8:469. doi: 10.3389/fchem.2020.00469
[34]	CIANO L, DAVIES G J, TOLMAN W B, et al. Bracing copper for the catalytic oxidation of C-H bonds[J]. Nature Catalysis,2018,1(8):571−577. doi: 10.1038/s41929-018-0110-9
[35]	ZHANG H Y, ZHOU H C, ZHAO Y, et al. Comparative studies of two AA10 family lytic polysaccharide monooxygenases from Bacillus thuringiensis[J]. Peer J,2023,11:e14670. doi: 10.7717/peerj.14670
[36]	VAAJE-KOLSTAD G, BUNAES A C, MATHIESEN G, et al. The chitinolytic system of Lactococcus lactis ssp. lactis comprises a nonprocessive chitinase and a chitin-binding protein that promotes the degradation of α- and β-chitin[J]. The FEBS Journal,2009,276(8):2402−2415. doi: 10.1111/j.1742-4658.2009.06972.x
[37]	VAAJE-KOLSTAD G, BOHLE L A, GASEIDNES S, et al. Characterization of the chitinolytic machinery of Enterococcus faecalis V583 and high-resolution structure of its oxidative CBM33 enzyme[J]. Journal of Molecular Biology,2012,416(2):239−254. doi: 10.1016/j.jmb.2011.12.033
[38]	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. [HUANG X Y, BI S Y, OU J H, et al. Process optimization of preparation of antioxidant chitooligosaccharides by papain[J]. Journal of Biology,2022,39(1):104−109.] doi: 10.3969/j.issn.2095-1736.2022.01.104 HUANG X Y, BI S Y, OU J H, et al. Process optimization of preparation of antioxidant chitooligosaccharides by papain[J]. Journal of Biology, 2022, 39（1）: 104−109. doi: 10.3969/j.issn.2095-1736.2022.01.104
[39]	DONG H Z, WANG Y S, ZHAO L M, et al. Key technologies of enzymatic preparation for DP 6-8 chitooligosaccharides[J]. Journal of Food Process Engineering,2015,38(4):336−344. doi: 10.1111/jfpe.12159
[40]	QIAN J Q, SHI B B, MO L Y et al. Preparation of chitooligosaccharides by α-amylase from chitosan with oxidative pretreatment[J]. Journal of Chemical Technology and Biotechnology,2021,96(12):3408−3413. doi: 10.1002/jctb.6901
[41]	XING R, LIU Y L, LI K C, et al. Monomer composition of chitooligosaccharides obtained by different degradation methods and their effects on immunomodulatory activities[J]. Carbohydrate Polymers,2017,157:1288−1297. doi: 10.1016/j.carbpol.2016.11.001
[42]	WU Y, HUANG Y C, ZHOU Y, et al. Degradation of chitosan by swirling cavitation[J]. Innovative Food Science and Emerging Technologies,2014,23:188−193. doi: 10.1016/j.ifset.2014.02.001
[43]	MARGOUTIDIS G, PARSONS V H, BOTTARO C S, et al. Mechanochemical amorphization of α-chitin and conversion into oligomers of N-acetyl-D-glucosamine[J]. ACS Sustainable Chemistry and Engineering,2018,6(2):1662−1669. doi: 10.1021/acssuschemeng.7b02870
[44]	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. [GUO M, ZHAO H, ZHANG C Z. Preparation and application of chitosan oligosaccharides[J]. China Food Additives,2022,33(10):267−271.] GUO M, ZHAO H, ZHANG C Z. Preparation and application of chitosan oligosaccharides[J]. China Food Additives, 2022, 33（10）: 267−271.
[45]	LIANG S, SUN Y X, DAI X L. A review of the preparation, analysis and biological functions of chitooligosaccharide[J]. International Journal of Molecular Sciences,2018,19(8):2197. doi: 10.3390/ijms19082197
[46]	BENCHAMAS G, HUANG G L, HUANG S Y, et al. Preparation and biological activities of chitosan oligosaccharides[J]. Trends in Food Science and Technology,2021,107:38−44. doi: 10.1016/j.jpgs.2020.11.027
[47]	卢春兰, 王蓓. 壳寡糖和几丁寡糖的制备方法及其在水产上的应用[J]. 广东农业科学,2023,50(2):136−146. [LU C L, WANG B. Preparation method of chitosan oligosaccharide and chitin oligosaccharide and their application in aquaculture[J]. Guangdong Agricultural Sciences,2023,50(2):136−146.] LU C L, WANG B. Preparation method of chitosan oligosaccharide and chitin oligosaccharide and their application in aquaculture[J]. Guangdong Agricultural Sciences, 2023, 50（2）: 136−146.
[48]	MITTAL A, SINGH A, HONG H, et al. Chitooligosaccharides from shrimp shell chitosan prepared using H₂O₂ or ascorbic acid/H₂O₂ redox pair hydrolysis:Characteristics, antioxidant and antimicrobial activities[J]. International Journal of Food Science and Technology,2023,58(5):2645−2660. doi: 10.1111/ijfs.15696
[49]	ALJBOUR N D, BEG M D H, GIMBUN, J. Acid hydrolysis of chitosan to oligomers using hydrochloric acid[J]. Chemical Engineering and Technology,2019,42(9):1741−1746. doi: 10.1002/ceat.201800527
[50]	原佳琪, 梁爽, 孙雅煊, 等. 壳寡糖的制备及生物学活性研究进展[J]. 生命的化学,2019,39(4):759−765. [YUAN J Q, LIANG S, SUN Y X, et al. Research progresses on the preparation and biological activities of chitooligosaccharides[J]. Chemistry of Life,2019,39(4):759−765.] YUAN J Q, LIANG S, SUN Y X, et al. Research progresses on the preparation and biological activities of chitooligosaccharides[J]. Chemistry of Life, 2019, 39（4）: 759−765.
[51]	季者, 蒋霞云, 李小倩, 等. 盐酸法降解壳聚糖制备特定聚合度壳寡糖(DP=5~7)的研究[J]. 上海海洋大学学报,2013,22(4):634−640. [JI Z, JIANG X Y, LI X Q, et al. Preparation of pentamer-to-heptamer chitooligosaccharides by hydrochloric acidic degradation of chitosan[J]. Journal of Shanghai Ocean University,2013,22(4):634−640.] JI Z, JIANG X Y, LI X Q, et al. Preparation of pentamer-to-heptamer chitooligosaccharides by hydrochloric acidic degradation of chitosan[J]. Journal of Shanghai Ocean University, 2013, 22（4）: 634−640.
[52]	焦富颖. 黄粉虫蜕制备壳寡糖及其应用[D]. 重庆:重庆工商大学, 2018. [JIAO F Y. Preparation of chito oligosaccharide from Tenebrio molitor slough and its application[D]. Chongqing:Chongqing Technology and Business University, 2018.] JIAO F Y. Preparation of chito oligosaccharide from Tenebrio molitor slough and its application[D]. Chongqing: Chongqing Technology and Business University, 2018.
[53]	OKORO O V, NIE L, GUNDUZ O, et al. Technoeconomic assessment of biopolymer production from crustacean waste with the UK as a case study[J]. Sustainability,2023,15(3):2280. doi: 10.3390/su15032280
[54]	GU Z M, CAI Q Y, LIU Y, et al. Electrochemical degradation of chitosan using Ti/Sb-SnO₂ electrode[J]. Journal of Polymers and the Environment,2013,21(2):479−486. doi: 10.1007/s10924-012-0532-4
[55]	CAI Q Y, GU Z M, CHEN Y, et al. Degradation of chitosan by an electrochemical process[J]. Carbohydrate Polymers,2010,79(3):783−785. doi: 10.1016/j.carbpol.2009.08.022
[56]	郑必胜, 周萌. 壳聚糖氧化降解制备壳寡糖的研究[J]. 现代食品科技,2012,28(8):959−963. [ZHENG B S, ZHOU M. Oxidation degradation of chitosan for preparation of oligochitosan[J]. Modern Food Science and Technology,2012,28(8):959−963.] ZHENG B S, ZHOU M. Oxidation degradation of chitosan for preparation of oligochitosan[J]. Modern Food Science and Technology, 2012, 28（8）: 959−963.
[57]	SIVARAMAKRISHNA D, BHUVANACHANDRA B, MALLAKUNTLA M K, et al. Pretreatment with KOH and KOH-urea enhanced hydrolysis of α-chitin by an endo-chitinase from Enterobacter cloacae subsp. cloacae[J]. Carbohydrate Polymers,2020,235:115952. doi: 10.1016/j.carbpol.2020.115952
[58]	SIVARAMAKRISHNA D, BHUVANACHANDRA B, NADENDLA S R, et al. Efficient conversion of α-chitin by multi-modular chitinase from Chitiniphilus shinanonensis with KOH and KOH-urea pretreatment[J]. Carbohydrate Polymers,2020,250:116923. doi: 10.1016/j.carbpol.2020.116923
[59]	SULTHAN R, REGHUNADHAN A, SAMBHUDEVAN S. A new era of chitin synthesis and dissolution using deep eutectic solvents-comparison with ionic liquids[J]. Journal of Molecular Liquids,2023,380:121794. doi: 10.1016/j.molliq.2023.121794
[60]	GAO X L, LIU H, SHUAI J B, et al. Rapid transesterification of cellulose in a novel DBU-derived ionic liquid:Efficient synthesis of highly substituted cellulose acetate[J]. International Journal of Biological Macromolecules,2023,242:125133. doi: 10.1016/j.ijbiomac.2023.125133
[61]	HUSSON E, HADAD C, HUET G, et al. Effect of room temperature ionic liquids on selective biocatalytic hydrolysis of chitin via sequential or simultaneous strategies[J]. Green Chemistry,2017,19(17):4122−4131. doi: 10.1039/C7GC01471F
[62]	STEUDTE S. Investigations on the stability and ecotoxicity of selected ionic liquid cations and anions[D]. Bremen:Universitaet Bremen, 2014:10698870.
[63]	LI J, HUANG W C, GAO L, et al. Efficient enzymatic hydrolysis of ionic liquid pretreated chitin and its dissolution mechanism[J]. Carbohydrate Polymers,2019,211:329−335. doi: 10.1016/j.carbpol.2019.02.027
[64]	BERTON P, SHAMSHINA J L, OSTADJOO S, et al. Enzymatic hydrolysis of ionic liquid-extracted chitin[J]. Carbohydrate Polymers,2018,199:228−235. doi: 10.1016/j.carbpol.2018.07.014
[65]	SINHA S, CHAND S, TRIPATHI P. Recent progress in chitosanase production of monomer-free chitooligosaccharides:Bioprocess strategies and future applications[J]. Applied Biochemistry and Biotechnology,2016,180(5):883−899. doi: 10.1007/s12010-016-2140-6
[66]	YU W L, HSIAO Y C, CHIANG B. Production of high degree polymerized chitooligosaccharides in a membrane reactor using purified chitosanase from Bacillus cereus[J]. Food Research International,2009,42(9):1355−1361. doi: 10.1016/j.foodres.2009.06.008
[67]	AIDER M, BRUNET S, BAZINET L. Effect of pH and cell configuration on the selective and specific electrodialytic separation of chitosan oligomers[J]. Separation and Purification Technology,2008,63:612−619. doi: 10.1016/j.seppur.2008.07.018
[68]	仲伟伟. 壳寡糖的分离纯化及稳定性研究[D]. 无锡:江南大学, 2018. [ZHONG W W. Study on isolation, purification and stability of chitooligosaccharides[D]. Wuxi:Jiangnan University, 2018.] ZHONG W W. Study on isolation, purification and stability of chitooligosaccharides[D]. Wuxi: Jiangnan University, 2018.
[69]	吴健锋. 专一酶水解壳聚糖高效制备壳寡糖的研究[D]. 广东:华南理工大学, 2018. [WU J F. Study on efficient preparation of chitosan oligosaccharide by specific enzyme hydrolysis[D]. Guangdong:South China University of Technology, 2018.] WU J F. Study on efficient preparation of chitosan oligosaccharide by specific enzyme hydrolysis[D]. Guangdong: South China University of Technology, 2018.
[70]	WEI X L, WANG Y F, XIAO J B, et al. Separation of chitooligosaccharides and the potent effects on gene expression of cell surface receptor CR3[J]. International Journal of Biological Macromolecules,2009,45(4):432−436. doi: 10.1016/j.ijbiomac.2009.07.003
[71]	LI K C, XING R G, LIU S, et al. Access to N-acetylated chitohexaose with well-defined degrees of acetylation[J]. Biomed Research International,2017,2017:2486515.
[72]	CHEN D, CHEN C C, ZHENG X H, et al. Chitosan oligosaccharide production potential of Mitsuaria sp. C4 and its whole-genome sequencing[J]. Frontiers in Microbiology,2021,12:695571. doi: 10.3389/fmicb.2021.695571
[73]	SEKI K, NISHIYAMA Y, MITSUTOMI M. Characterization of a novel exo-chitosanase, an exo-chitobiohydrolase, from Gongronella butleri[J]. Journal of Bioscience and Bioengineering,2019,127(4):425−429. doi: 10.1016/j.jbiosc.2018.09.009
[74]	XU Y X, WANG H, ZHU B W, et al. Purification and biochemical characterization of a novel chitosanase cloned from the gene of Kitasatospora setae KM-6054 and its application in the production of chitooligosaccharides[J]. World Journal of Microbiology and Biotechnology,2023,39(5):111. doi: 10.1007/s11274-023-03561-z
[75]	严佳佳, 尤田, 张雪梅, 等. 一种海洋几丁质酶产生菌的筛选及酶学性质研究[J]. 食品与发酵工业,2023,49(13):40−48. [YAN J J, YOU T, ZHANG X M, et al. Screening of a marine chitinase-producing bacterium and its enzymatic properties[J]. Food and Fermentation Industries,2023,49(13):40−48.] YAN J J, YOU T, ZHANG X M, et al. Screening of a marine chitinase-producing bacterium and its enzymatic properties[J]. Food and Fermentation Industries, 2023, 49（13）: 40−48.
[76]	YU Y, LI K C. Adsorption characteristics of chitooligosaccharides onto activated charcoal in aqueous solutions[J]. Journal of Oceanology and Limnology,2020,38(2):342−350. doi: 10.1007/s00343-019-8327-2
[77]	HATTORI T, SAKABE Y, OGATA M, et al. Enzymatic synthesis of an α-chitin-like substance via lysozyme-mediated transglycosylation[J]. Carbohydrate Research,2012,347(1):16−22. doi: 10.1016/j.carres.2011.09.025
[78]	LI K C, XING R E, LIU S, et al. Advances in preparation, analysis and biological activities of single chitooligosaccharides[J]. Carbohydrate Polymers,2016,139:178−190. doi: 10.1016/j.carbpol.2015.12.016
[79]	ALLAN C P, HADWIGEI L A. The fungicidal effect of chitosan on fungi of varying cell wall composition[J]. Experimental Mycology,1979,3:285−287. doi: 10.1016/S0147-5975(79)80054-7
[80]	JEON Y, PARK P, KIM S. Antimicrobial effect of chitooligosaccharides produced by bioreactor[J]. Carbohydrate Polymers,2001,44(1):71−76. doi: 10.1016/S0144-8617(00)00200-9
[81]	HAO Z M, ZHANG Y R, SUN Z, et al. Chitooligosaccharide as a possible replacement for sulfur dioxide in winemaking[J]. Applied Sciences,2020,10(2):578. doi: 10.3390/app10020578
[82]	TSAI G J, WU Z Y, SU W H. Antibacterial activity of a chitooligosaccharide mixture prepared by cellulase digestion of shrimp chitosan and its application to milk preservation[J]. Journal of Food Protection,2000,63(6):747−752. doi: 10.4315/0362-028X-63.6.747
[83]	RAKKHUMKAEW N, PENGSUK C. Chitosan and chitooligosaccharides from shrimp shell waste:Characterization, antimicrobial and shelf life extension in bread[J]. Food Science and Biotechnology,2018,27(4):1201−1208. doi: 10.1007/s10068-018-0332-2
[84]	陈颖, 刘程惠, 白雯睿, 等. 壳寡糖涂膜对鲜切苹果的保鲜作用[J]. 食品工业科技,2019,40(9):269−274. [CHEN Y, LIU C H, BAI W R, et al. Effects of chitosan oligosaccharide on preservation of fresh-cut apples[J]. Science and Technology of Food Industry,2019,40(9):269−274.] CHEN Y, LIU C H, BAI W R, et al. Effects of chitosan oligosaccharide on preservation of fresh-cut apples[J]. Science and Technology of Food Industry, 2019, 40（9）: 269−274.
[85]	陈丹, 王月慧, 朱玥, 等. 壳寡糖对面团、酥性饼干品质及抗氧化性的影响[J]. 食品工业科技,2023,44(18):84−90. [CHEN D, WANG Y H, ZHU Y, et al. Effect of chito-oligosaccharide on the quality and antioxidation of dough and crispy biscuits[J]. Science and Technology of Food Industry,2023,44(18):84−90.] CHEN D, WANG Y H, ZHU Y, et al. Effect of chito-oligosaccharide on the quality and antioxidation of dough and crispy biscuits[J]. Science and Technology of Food Industry, 2023, 44（18）: 84−90.
[86]	龚周亮, 赵良忠, 刘汁琪, 等. 壳寡糖在湘派休闲豆干保鲜中的应用研究[J]. 食品安全导刊,2023(10):62−65. [GONG Z L, ZHAO L Z, LIU Z Q, et al. Study on application of chito-oligosaccharide in preservation of leisure dried bean in hunan pie[J]. China Food Safety Magazine,2023(10):62−65.] GONG Z L, ZHAO L Z, LIU Z Q, et al. Study on application of chito-oligosaccharide in preservation of leisure dried bean in hunan pie[J]. China Food Safety Magazine, 2023（10）: 62−65.
[87]	SINGH A, BENJAKUL S. The combined effect of squid pen chitooligosaccharides and high voltage cold atmospheric plasma on the shelf-life extension of Asian sea bass slices stored at 4 ℃[J]. Innovative Food Science and Emerging Technologies,2020,64:102339. doi: 10.1016/j.ifset.2020.102339
[88]	刘丽丹, 王帅, 金臻岚. 壳寡糖处理对冷藏期间大五星枇杷贮藏品质的影响[J]. 保鲜与加工,2018,18(2):39−43,49. [LIU L D, WANG S, JIN Z L. Effects of chito-oligosaccharide treatment on storage quality of big five-pointed star loquat fruit during storage at low temperature[J]. Storage and Process,2018,18(2):39−43,49.] LIU L D, WANG S, JIN Z L. Effects of chito-oligosaccharide treatment on storage quality of big five-pointed star loquat fruit during storage at low temperature[J]. Storage and Process, 2018, 18（2）: 39−43,49.
[89]	赵韩栋, 秦畅, 郭风军, 等. 采后壳寡糖处理减轻皇冠梨果皮褐变的研究[J]. 中国食品学报,2022,22(4):276−284. [ZHAO H D, QIN C, GUO F J, et al. Study on chitosan oligosaccharides treatment alleviating peel browning of Huanggaun pear[J]. Journal of Chinese Institute of Food Science and Technology,2022,22(4):276−284.] ZHAO H D, QIN C, GUO F J, et al. Study on chitosan oligosaccharides treatment alleviating peel browning of Huanggaun pear[J]. Journal of Chinese Institute of Food Science and Technology, 2022, 22（4）: 276−284.
[90]	段树华, 罗皓, 兰林, 等. 壳寡糖处理对甜樱桃采后贮藏品质的影响[J]. 北方园艺,2023(6):87−95. [DUAN S H, LUO H, LAN L, et al. Effects of chitosan oligosaccharide treatment on the quality of sweet cherries after harvest storage[J]. Northern Horticulture,2023(6):87−95.] DUAN S H, LUO H, LAN L, et al. Effects of chitosan oligosaccharide treatment on the quality of sweet cherries after harvest storage[J]. Northern Horticulture, 2023（6）: 87−95.
[91]	吴会敏, 王月慧, 朱玥, 等. 壳寡糖对海绵蛋糕物理及感官特性的影响[J]. 食品科技,2022,47(6):270−277. [WU H M, WANG Y H, ZHU Y, et al. Effect of chitooligosaccharide on sponge cake batter properties and cake quality[J]. Food Science and Technology,2022,47(6):270−277.] WU H M, WANG Y H, ZHU Y, et al. Effect of chitooligosaccharide on sponge cake batter properties and cake quality[J]. Food Science and Technology, 2022, 47（6）: 270−277.
[92]	KE Y, DING B B, FU Y, et al. Effects of chitosan oligosaccharide and Hyriopsis cumingii polysaccharide on the quality of wheat flour and extruded flour products[J]. Food Science and Biotechnology,2021,30(7):911−919. doi: 10.1007/s10068-021-00933-9
[93]	NAVEED M, PHIL L, SOHAIL M, et al. Chitosan oligosaccharide (COS):An overview[J]. International Journal of Biological Macromolecules,2019,129:827−843. doi: 10.1016/j.ijbiomac.2019.01.192
[94]	王胜田, 姚乾元. 一种用于保肝护肝的壳寡糖胶囊:中国, 113304188A[P]. 2021-08-27. [WANG S T, YAO Q Y. A chitooligosaccharide capsule for liver protection:China, 113304188A[P]. 2021-08-27.] WANG S T, YAO Q Y. A chitooligosaccharide capsule for liver protection: China, 113304188A[P]. 2021-08-27.
[95]	郝桂娟, 张宾, 章样扬, 等. 壳寡糖锌配合物对氧化衰老模型小鼠的抗氧化作用[J]. 核农学报,2019,33(6):1156−1164. [HAO G J, ZHANG B, ZHANG Y Y, et al. Antioxidant effect of chitooligosaccharide-zinc complex on the oxidative aging mice model[J]. Journal of Nuclear Agricultural Sciences,2019,33(6):1156−1164.] HAO G J, ZHANG B, ZHANG Y Y, et al. Antioxidant effect of chitooligosaccharide-zinc complex on the oxidative aging mice model[J]. Journal of Nuclear Agricultural Sciences, 2019, 33（6）: 1156−1164.
[96]	苏政权, 曹华, 白研, 等. 一种壳寡糖肠溶胶囊及其制备方法和应用:中国, 114376982B[P]. 2023-06-30. [SU Z Q, CAO H, BAI Y, et al. A chitooligosaccharide enteric-soluble capsule and its preparation process and application:China, 114376982B[P]. 2023-06-30.] SU Z Q, CAO H, BAI Y, et al. A chitooligosaccharide enteric-soluble capsule and its preparation process and application: China, 114376982B[P]. 2023-06-30.
[97]	罗雷, 祁一鸣, 任琼赭, 等. 壳寡糖在提升肠道通透性和作为BCSⅢ类药物口服吸收促进剂方面的应用:中国, 113813390B[P]. 2023-03-31. [LUO L, QI Y M, REN Q Z, et al. Application of chitooligosaccharide in enhancing intestinal permeability and serving as oral absorption promoter for BCSIII drugs:China, 113813390B[P]. 2023-03-31.] LUO L, QI Y M, REN Q Z, et al. Application of chitooligosaccharide in enhancing intestinal permeability and serving as oral absorption promoter for BCSIII drugs: China, 113813390B[P]. 2023-03-31.
[98]	徐然, 左华江, 唐春怡, 等. 壳聚糖类吸附材料的制备及应用研究进展[J]. 现代化工,2020,40(9):25−29. [XU R, ZUO H J, TANG C Y, et al. Advances in preparation and application of chitosan-based adsorption materials[J]. Modern Chemical Industry,2020,40(9):25−29.] XU R, ZUO H J, TANG C Y, et al. Advances in preparation and application of chitosan-based adsorption materials[J]. Modern Chemical Industry, 2020, 40（9）: 25−29.
[99]	庄林, 操俊, 李月婵, 等. 壳寡糖复合固体饮料对高尿酸血症小鼠肠道微生态的调节作用研究[J]. 食品研究与开发,2022,43(11):56−62. [ZHUANG L, CAO J, LI Y C, et al. Effect of chitooligosaccharide compound solid beverage on the intestinal microecology of hyperuricemia mice[J]. Food Research and Development,2022,43(11):56−62.] ZHUANG L, CAO J, LI Y C, et al. Effect of chitooligosaccharide compound solid beverage on the intestinal microecology of hyperuricemia mice[J]. Food Research and Development, 2022, 43（11）: 56−62.
[100]	姜雅杰, 王畅, 席茂盛, 等. 壳寡糖复合固体饮料对Ⅱ型糖尿病小鼠肠道菌群结构的影响[J]. 食品工业科技,2020,41(8):301−306. [JIANG Y J, WANG C, XI M S, et al. Effect of chitooligosaccharide compound solid beverage on intestinal flora of type II diabetic mice[J]. Science and Technology of Food Industry,2020,41(8):301−306.] JIANG Y J, WANG C, XI M S, et al. Effect of chitooligosaccharide compound solid beverage on intestinal flora of type II diabetic mice[J]. Science and Technology of Food Industry, 2020, 41（8）: 301−306.
[101]	喻凯. 一种增强肠胃功能及免疫力几丁寡糖食品及其制备方法:中国, 115428851A[P]. 2022-12-06. [YU K. A chitin oligosaccharide food that enhances gastrointestinal function and immunity and its preparation process:China, 115428851A[P]. 2022-12-06.] YU K. A chitin oligosaccharide food that enhances gastrointestinal function and immunity and its preparation process: China, 115428851A[P]. 2022-12-06.
[102]	王孝文, 台文静, 王海华, 等. 一种具有增强免疫功能的浒苔多糖保健食品及制备方法:中国, 114376233A[P]. 2022-04-22. [WANG X W, TAI W J, WANG H H, et al. A health food containing polysaccharides from Enteromorpha prolifera with enhanced immune function and its preparation process:China, 114376233A[P]. 2022-04-22.] WANG X W, TAI W J, WANG H H, et al. A health food containing polysaccharides from Enteromorpha prolifera with enhanced immune function and its preparation process: China, 114376233A[P]. 2022-04-22.
[103]	孙翠红, 徐翠莲, 赵铭钦, 等. 壳寡糖及其衍生物抗烟草花叶病毒机理的初步研究[J]. 中国烟草科学,2015,36(2):87−92. [SUN C H, XU C L, ZHAO M Q, et al. The inhibitory effects of chitooligosaccharides and its derivatives on Tobacco Mosaic Virus (TMV)[J]. Chinese Tobacco Science,2015,36(2):87−92.] SUN C H, XU C L, ZHAO M Q, et al. The inhibitory effects of chitooligosaccharides and its derivatives on Tobacco Mosaic Virus （TMV）[J]. Chinese Tobacco Science, 2015, 36（2）: 87−92.
[104]	高雨萌, 费昭雪, 史健飞, 等. 壳寡糖对花椒干腐病菌的抑菌活性研究[J]. 中国森林病虫,2021,40(3):1−8. [GAO Y M, FEI Z X, SHI J F, et al. Antifungal activities of oligochitosan against the pathogen of stem canker of Zanthoxylum bungeanum[J]. Forest Pest and Disease,2021,40(3):1−8.] GAO Y M, FEI Z X, SHI J F, et al. Antifungal activities of oligochitosan against the pathogen of stem canker of Zanthoxylum bungeanum[J]. Forest Pest and Disease, 2021, 40（3）: 1−8.
[105]	尹雅洁, 张宗杰, 夏险, 等. 壳寡糖对水稻幼苗生长及抗逆性影响[J]. 生物学杂志,2021,38(1):77−80. [YI Y J, ZHANG Z J, XIA X, et al. Effects of oligochitosan on the growth and stress resistance of rice seedlings under abiotic stress[J]. Journal of Biology,2021,38(1):77−80.] YI Y J, ZHANG Z J, XIA X, et al. Effects of oligochitosan on the growth and stress resistance of rice seedlings under abiotic stress[J]. Journal of Biology, 2021, 38（1）: 77−80.
[106]	金国强, 李永杰, 高恒锦, 等. 壳寡糖对早熟温州蜜柑果实品质的影响[J]. 浙江柑橘,2020,37(2):20−24. [JIN G Q, LI Y J, GAO H J, et al. Effect of chitooligosaccharides on the quality of early maturing wenzhou honey citrus fruit[J]. Zhejiang Ganju,2020,37(2):20−24.] JIN G Q, LI Y J, GAO H J, et al. Effect of chitooligosaccharides on the quality of early maturing wenzhou honey citrus fruit[J]. Zhejiang Ganju, 2020, 37（2）: 20−24.
[107]	黄雪燕, 金伟, 赵灵云. 壳寡糖对温岭高橙果实膨大和品质的影响[J]. 农业科技通讯,2018(12):186−188. [HUANG X Y, JIN W, ZHAO L Y. Effect of chitooligosaccharides on the expansion and quality of wenling high orange fruit[J]. Bulletin of Agricultural Science and Technology,2018(12):186−188.] HUANG X Y, JIN W, ZHAO L Y. Effect of chitooligosaccharides on the expansion and quality of wenling high orange fruit[J]. Bulletin of Agricultural Science and Technology, 2018（12）: 186−188.
[108]	BADAWY M E I, RABEA E I. Potential of the biopolymer chitosan with different molecular weights to control postharvest gray mold of tomato fruit[J]. Postharvest Biology and Technology,2009,51(1):110−117. doi: 10.1016/j.postharvbio.2008.05.018
[109]	DAS S N, MADHUPRAKASH J, SARMA P V, et al. Biotechnological approaches for field applications of chitooligosaccharides (COS) to induce innate immunity in plants[J]. Critical Reviews in Biotechnology,2015,35(1):29−43. doi: 10.3109/07388551.2013.798255
[110]	KATIYAR D, HEMANTARANJAN A, SINGH B. Chitosan as a promising natural compound to enhance potential physiological responses in plant:A review[J]. Indian Journal of Plant Physiology,2015,20(1):1−9. doi: 10.1007/s40502-015-0139-6

Supplements (1)

Supplements
Other Related Supplements

Cited By

Cited by

Periodical cited type(9)

1.	吴军林，徐梅珍，蒋桂丽，杨华. 食品微生物学课程教学创新性探索及思考. 食品工业. 2025(02): 142-146 .
2.	李向梅，朱月，柳春红，徐振林，雷红涛，钟青萍. 课程思政视域下“食品卫生学”案例教学改革与育人效果评价. 食品工业. 2025(02): 237-242 .
3.	王丽娜，罗志. 土壤环境监测课程思政元素的挖掘与教学实施探索. 现代商贸工业. 2024(12): 261-263 .
4.	隋晓楠，张妍，黄国，付昳丹，梁香玉，赵尚清，王思琦，杨爱峥，霍俊伟，江连洲. 省一流专业引领下“粮油加工副产物综合利用”课程创新创业元素的设计与实践. 食品工业科技. 2024(13): 308-314 . 本站查看
5.	关海宁，刁小琴，刘登勇，励建荣，李学鹏，仪淑敏，范金波，赵志南. “乡村振兴”背景下食品类专业型硕士“实践驱动、多维融合、创新引领”协同培养机制的探讨. 食品工业科技. 2024(14): 371-377 . 本站查看
6.	林鹏，宋姗姗，范金波，李学鹏，励建荣. 基于OBE教学理念对《食品免疫学》课程教学改革与实践. 食品工业科技. 2024(14): 361-370 . 本站查看
7.	张妍，杨景旭，隋晓楠. “园艺产品采后生理及贮运加工”课程建设与创新. 食品工业. 2024(07): 221-225 .
8.	张晶，施行健，郁舒兰. 交互设计类课程中的思政元素挖掘与融合路径探索. 设计. 2024(17): 74-77 .
9.	解文丽，郭俊南，王晖，温清苹. 课程思政的实践探索——以《海水利用技术》为例. 广东化工. 2023(19): 170-173+151 .