FAN Liping, LIU Zhiwei, JIAO Wenjuan, et al. Research Progress on Preparation and Efficacy of Chiooligosaccharide Complex[J]. Science and Technology of Food Industry, 2022, 43(9): 404−415. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2021040148.
Citation: FAN Liping, LIU Zhiwei, JIAO Wenjuan, et al. Research Progress on Preparation and Efficacy of Chiooligosaccharide Complex[J]. Science and Technology of Food Industry, 2022, 43(9): 404−415. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2021040148.

Research Progress on Preparation and Efficacy of Chiooligosaccharide Complex

More Information
  • Received Date: April 14, 2021
  • Available Online: February 28, 2022
  • Chitooligosaccharides are the only basic oligosaccharides in nature with -NH2 and -OH functional groups. They are easily soluble in water and have extremely high biological activities such as antibacterial, anti-inflammatory, anti-oxidant, and anti-cancer. Chitooligosaccharides can be combined with metal ions, proteins, polysaccharides, lipids, and flavonoids through coordination complexation, electrostatic interaction, transamination, Maillard reaction, amidation, esterification, and carboxylation of chitooligosaccharides. Chitooligosaccharide complex has good stability and high water solubility, and can have the biological activity characteristics of chitosan oligosaccharide and complex factor at the same time, which effectively broadens the application range of the complex and enhances the effect of function. In addition, studying on the new compound method and the safety of chitooligosaccharide complex, which will become an important research direction. This article summarizes the preparation methods and compound objects of chitooligosaccharide complexes, the efficacy and application research of chitooligosaccharide complexes in functional foods, agriculture, biomedicine and other fields in recent years in order to provide a reference for the further study of chitooligosaccharide complexes.
  • [1]
    LIANG S, SUN Y, DAI X. 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
    [2]
    MUANPRASAT C, CHATSUDTHIPONG V. Chitosan oligosaccharide: Biological activities and potential therapeutic applications[J]. Pharmacology & Therapeutics,2017,170:80−97.
    [3]
    SUN G, YANG Q, ZHANG A, et al. Synergistic effect of the combined bio-fungicides epsilon-poly-l-lysine and chitooligosaccharide in controlling grey mould (Botrytis cinerea) in tomatoes[J]. International Journal of Food Microbiology,2018,276:46−53. doi: 10.1016/j.ijfoodmicro.2018.04.006
    [4]
    BAI K, HONG B, HUANG W, et al. Selenium-nanoparticles-loaded chitosan/chitooligosaccharide microparticles and their antioxidant potential: A chemical and in vivo investigation[J]. Pharmaceutics,2020,12(1):43. doi: 10.3390/pharmaceutics12010043
    [5]
    SANTOS-MORIANO P, FERNANDEZ-ARROJO L, MENGIBAR M, et al. Enzymatic production of fully deacetylated chitooligosaccharides and their neuroprotective and anti-inflammatory properties[J]. Biocatalysis and Biotransformation: Biocatalysis in Spain: A Field of Success and Innovation,2018,36(1):57−67.
    [6]
    LUO Z, DONG X, KE Q, et al. Downregulation of CD147 by chitooligosaccharide inhibits MMP-2 expression and suppresses the metastatic potential of human gastric cancer[J]. Oncology Letters,2014,8(1):361−366. doi: 10.3892/ol.2014.2115
    [7]
    ZHANG P, LIU W, PENG Y, et al. Toll like receptor 4 (TLR4) mediates the stimulating activities of chitosan oligosaccharide on macrophages[J]. International Immunopharmacology,2014,23(1):254−261. doi: 10.1016/j.intimp.2014.09.007
    [8]
    YUAN X, ZHENG J, JIAO S, et al. A review on the preparation of chitosan oligosaccharides and application to human health, animal husbandry and agricultural production[J]. Carbohydrate Polymers,2019,220:60−70. doi: 10.1016/j.carbpol.2019.05.050
    [9]
    YANG S, LIN F, TSAI H, et al. Alginate-folic acid-modified chitosan nanoparticles for photodynamic detection of intestinal neoplasms[J]. Biomaterials,2011,32(8):2174−2182. doi: 10.1016/j.biomaterials.2010.11.039
    [10]
    杜昱光. 壳寡糖的功能研究及应用[M]. 北京: 化学工业出版社, 2009.

    DU Yuguang. The function research and application of chitosan oligosaccharide[M]. Beijing: Chemical Industry Press, 2009.
    [11]
    JUTHAMAS R, SORADA K, YASUHIKO T, et al. Modulation of in vitro Attachment, proliferation and osteogenic differentiation of rat bone-marrow-derived stem cells using different molecular mass chitosans and their blends with gelatin[J]. Journal of Biomaterials Science, Polymer Edition,2010,21(8-9):1301−1304.
    [12]
    LIU X, XIA W, JIANG Q, et al. Synthesis, characterization, and antimicrobial activity of kojic acid grafted chitosan oligosaccharide[J]. Journal of Agricultural and Food Chemistry,2013,62(1):297−303.
    [13]
    YUE L, LI J, CHEN W, et al. Geraniol grafted chitosan oligosaccharide as a potential antibacterial agent[J]. Carbohydrate Polymers,2017,176:356−364. doi: 10.1016/j.carbpol.2017.07.043
    [14]
    WANG Z, LI Y, XING L, et al. Effects of the anti-angiogenic carbohydrate-peptide conjugate, chitooligosaccharide-ES2 on endothelial cells and tumor-bearing mice[J]. Carbohydrate Polymers,2019,208:302−313. doi: 10.1016/j.carbpol.2018.12.089
    [15]
    YAN F, YAN F, YU X, et al. Optimized preparation, characterization, and antioxidant activity of chitooligosaccharide-glycine Maillard reaction products[J]. Journal of Food Science and Technology,2018,55(2):712−720. doi: 10.1007/s13197-017-2982-0
    [16]
    CAO R, ZHAO Y, ZHOU Z, et al. Enhancement of the water solubility and antioxidant activity of hesperidin by chitooligosaccharide[J]. Journal of the Science of Food and Agriculture,2018,98(6):2422−2427. doi: 10.1002/jsfa.8734
    [17]
    曾名勇. 甲壳质和甲壳胺的化学改性和应用[J]. 渔业机械仪器,1994(6):35−39. [ZENG Mingyong. Chemical modification and application of chitin and chitosan[J]. Fishery Machinery and Instruments,1994(6):35−39.
    [18]
    YIN H, DU Y, DONG Z. Chitin oligosaccharide and chitosan oligosaccharide: Two similar but different plant elicitors[J]. Frontiers in Plant Science,2016,7:522.
    [19]
    SAVINO S, JENSEN S, TERWISSCHA V S A, et al. Analysis of the structure and substrate scope of chitooligosaccharide oxidase reveals high affinity for C2-modified glucosamines[J]. FEBS Letters,2020,594(17):2819−2828. doi: 10.1002/1873-3468.13854
    [20]
    周天韡, 唐文琼, 沈青. 壳聚糖改性技术的新进展Ⅰ. 烷基化、酰化以及接枝化改性[J]. 高分子通报,2008(11):54−65. [ZHOU Tianwei, TANG Wenqiong, SHEN Qing. New progress on modifications of chitosan Ⅰ. Alkylation, acylation and grafting modification[J]. Polymer Bulletin,2008(11):54−65.
    [21]
    周天韡, 唐文琼, 沈青. 壳聚糖改性技术的新进展Ⅱ. 交联化、季铵盐化、羧基化改性及其低聚糖衍生物[J]. 高分子通报,2008(12):52−66. [ZHOU Tianwei, TANG Wenqiong, SHEN Qing. New progress on modifications of chitosan Ⅱ. Cross-linking, quaternary ammonium salting, carboxylation modification and its oligosaccharide derivatives[J]. Polymer Bulletin,2008(12):52−66.
    [22]
    胡雪芳, 田志清, 梁亮, 等. 6-羧基壳寡糖螯合钙制备工艺与络合性能研究[J]. 农业机械学报,2018,49(4):381−388. [HU Xuefang, TIAN Zhiqing, LIANG Liang, et al. Preparation technology and complexing properties of 6-Carboxy chitooligosaccharides chelate calcium(CCOS-Ca(Ⅱ)[J]. Journal of Agricultural Machinery,2018,49(4):381−388. doi: 10.6041/j.issn.1000-1298.2018.04.045
    [23]
    任群翔, 翟玉春, 白玉红, 等. 壳寡糖与硝酸钕配合物的合成和配位机理研究[J]. 分子科学学报,2008(5):316−319. [REN Qunxiang, ZHAI Yuchun, BAI Yuhong, et al. Synthesis and coordination mechanism of the coordination compound of chitooligosaccharide with Nd(NO)3[J]. Journal of Molecular Science,2008(5):316−319. doi: 10.3969/j.issn.1000-9035.2008.05.005
    [24]
    徐进云, 贾辉, 杨俊玲, 等. 壳寡糖铁(Ⅲ)配位产物的合成与表征[J]. 天津工业大学学报,2017,36(2):25−30. [XU Jinyun, JIA Hui, YANG Junling, et al. Synthesis and characterization of chitooligosaccharides-Fe(Ⅲ) complex[J]. Journal of Tianjin Polytechnic University,2017,36(2):25−30. doi: 10.3969/j.issn.1671-024x.2017.02.005
    [25]
    田金花, 杨华, 迟光伟, 等. 壳寡糖锌(Ⅱ)配合物的合成与结构表征[J]. 高分子通报,2011(1):71−74. [TIAN Jinhua, YANG Hua, CHI Guangwei, et al. Synthesis and characterization of chitooligosaccharides-zinc complex[J]. Polymer Bulletin,2011(1):71−74.
    [26]
    WANG Y, LIU T, ZHONG G. Synthesis, characterization and applications of copper(II) complexes with Schiff bases derived from chitooligosaccharide and iodosubstituted salicylaldehyde[J]. Carbohydrate Polymers,2019,224:115151. doi: 10.1016/j.carbpol.2019.115151
    [27]
    何昇鸿, 王一安, 曾令智, 等. 营养强化剂壳寡糖铜、锰螯合物的合成与表征及抗氧化活性[J]. 中国食品添加剂,2018(4):148−153. [HE Shenghong, WANG Yian, ZENG Lingzhi, et al. Synthesis, characterization and antioxidant activity of nutrition fortifiers chitooligosaccharide copper and manganese chelates[J]. China Food Additives,2018(4):148−153. doi: 10.3969/j.issn.1006-2513.2018.04.024
    [28]
    吕丹丹, 张宾, 房传栋, 等. 基于分子模拟的壳寡糖-金属配合物的结合模式分析[J]. 中国食品学报,2019,19(7):79−84. [LV Dandan, ZHANG Bin, FANG Chuandong, et al. Analysis of binding mechanism between chitooligosaccharides and metal ions based on molecular simulation[J]. Journal of Chinese Institute of Food Science and Technology,2019,19(7):79−84.
    [29]
    许牡丹, 王晓燕. 壳低聚糖Cr(Ⅲ)离子配合物的制备及其结构表征[J]. 现代食品科技,2007(12):15−18. [XU Mudan, WANG Xiaoyan. Preparation and structure characterization of oligo-chitosan Cr(Ⅲ) complex[J]. Modern Food Science and Technology,2007(12):15−18.
    [30]
    NASEEM K, FAROOQI Z H, BEGUM R, et al. Synthesis and characterization of poly(N-isopropylmethacrylamide-acrylic acid) smart polymer microgels for adsorptive extraction of copper(II) and cobalt(II) from aqueous medium: Kinetic and thermodynamic aspects[J]. Environmental Science and Pollution Research International,2020,27(22):28169−28182. doi: 10.1007/s11356-020-09145-w
    [31]
    JIANHUA L, QIAOMEI R, YUTING D. Glycation a promising method for food protein modification: Physicochemical properties and structure, a review[J]. Food Research International,2012,49(1):170−183. doi: 10.1016/j.foodres.2012.07.034
    [32]
    ZHANG H, ZHANG Y, BAO E, et al. Preparation, characterization and toxicology properties of α- and β-chitosan Maillard reaction products nanoparticles[J]. International Journal of Biological Macromolecules,2016,89:287−296. doi: 10.1016/j.ijbiomac.2016.04.079
    [33]
    YU X, JING Y, YAN F. Chitooligosaccharide-lysine Maillard reaction products: Preparation and potential application on fresh-cut kiwifruit[J]. Food and Bioprocess Technology,2019,12(7):1133−1143. doi: 10.1007/s11947-019-02284-0
    [34]
    DU Y, RYAN K S. Pyridoxal phosphate-dependent reactions in the biosynthesis of natural products[J]. Natural Product Reports,2019,36(3):430−457. doi: 10.1039/C8NP00049B
    [35]
    EIDEN C G, ALDRICH C C. Synthesis of a 3-amino-2, 3-dihydropyrid-4-one and related heterocyclic analogues as mechanism-based inhibitors of BioA, a pyridoxal phosphate-dependent enzyme[J]. The Journal of Organic Chemistry,2017,82(15):7806−7819. doi: 10.1021/acs.joc.7b00847
    [36]
    江文, 周桢, 石业新, 等. 壳寡糖-水解麦醇溶肽共聚物的制备和表征[J]. 应用化学,2016,33(3):284−292. [JIANG Wen, ZHOU Zhen, SHI Yexin, et al. Preparation and characterization of chitosan oligo-saccharide-hydrolyzed gliadin copolymer[J]. Chinese Journal of Applied Chemistry,2016,33(3):284−292. doi: 10.11944/j.issn.1000-0518.2016.03.150226
    [37]
    YANG R, ZUO P, ZHANG M, et al. Transglutaminase induced oligochitosan glycosylation of ferritin as a novel nanocarrier for food bioactive molecules[J]. Food Hydrocolloids,2019,94:500−509. doi: 10.1016/j.foodhyd.2019.03.049
    [38]
    郭晓晓, 农叶琳, 王平, 等. TGase催化丝胶-壳寡糖交联及其复合膜材料性能探究[J]. 丝绸,2020,57(7):071102. [GUO Xiaoxiao, NONG Yelin, WANG Ping, et al. TGase-catalyzed crosslinking reaction between sericin and chitooligosaccharide and properties of the composite membrane[J]. Journal of Silk,2020,57(7):071102.
    [39]
    AVTAR S, SOOTTAWAT B, THUMMANOON P. Effect of chitooligosaccharide from squid pen on gel properties of sardine surimi gel and its stability during refrigerated storage[J]. International Journal of Food Science and Technology,2019,54(10):2831−2838. doi: 10.1111/ijfs.14199
    [40]
    刘卅, 林欣欣, 陈立班. 聚电解质复合物研究进展[J]. 广州化学,1996(3):1−6. [LIU Sa, LIN Xinxin, CHEN Liban. Progress in polyelectrolyte complexes[J]. Guangzhou Chemistry,1996(3):1−6.
    [41]
    ADRIAN M, AXEL J, RENATO G, et al. A study on the molecular existing interactions in nanoherbicides: A chitooligosaccharide/tripolyphosphate loaded with paraquat case[J]. Colloids and Surfaces A: Physicochemical and Engineering Aspects,2019,562(2):220−228.
    [42]
    CHEN K, QIAN Y, WANG C, et al. Tumor microenvironment-responsive, high internal phase Pickering emulsions stabilized by lignin/chitosan oligosaccharide particles for synergistic cancer therapy[J]. Journal of Colloid and Interface Science,2021,591:352−362. doi: 10.1016/j.jcis.2021.02.012
    [43]
    曾尔曼, 杨雪慧, 陈丹梅, 等. 壳寡糖和聚丙烯酸的自组装行为[J]. 商丘师范学院学报,2008(9):1−4. [ZENG Erman, YANG Xuehui, CHEN Danmei, et al. The self-assembly conduct of chitooligosaccharide and polyacrylic acid[J]. Journal of Shangqiu Normal University,2008(9):1−4. doi: 10.3969/j.issn.1672-3600.2008.09.001
    [44]
    STOYANOVA N, IGNATOVA M, MANOLOVA N, et al. Nanoparticles based on complex of berberine chloride and polymethacrylic or polyacrylic acid with antioxidant and in vitro antitumor activities[J]. International Journal of Pharmaceutics,2020,584:119426. doi: 10.1016/j.ijpharm.2020.119426
    [45]
    CAO J, WANG Y, HE C, et al. Ionically crosslinked chitosan/poly(acrylic acid) hydrogels with high strength, toughness and antifreezing capability[J]. Carbohydrate Polymers,2020,242:116420. doi: 10.1016/j.carbpol.2020.116420
    [46]
    胡晓芬, 盛振华, 杨洁红, 等. (肝素/壳寡糖/Pluronic®)静电组装多层膜的构建[J]. 高分子学报,2015(6):650−656. [HU Xiaofen, SHENG Zhenhua, YANG Jiehong, et al. Fabrication of (heparin/chitosan oligosaccharides/Pluronic®) multilayer films via electrostatic layer-by-layer assembly[J]. Acta Polymerica Sinica,2015(6):650−656. doi: 10.11777/j.issn1000-3304.2015.14392
    [47]
    范丽萍. 壳寡糖/果胶静电自组装复合作用以及复合物负载BSA的研究[D]. 广州: 华南理工大学, 2019.

    FAN Liping. Studies on chitooligosaccharide/pectin electrostatic self-assembly and complex BSA loading[D]. Guangzhou: South China University of Technology, 2019.
    [48]
    CHEBL M, ABIAD M G, MOUSSA Z, et al. Two modes of associations of curcumin with pre- and nanoaggregated chitosan oligosaccharide lactate: Ionic strength and hydrophobic bile salt modulate partition of drug and self-assembly process[J]. The Journal of Physical Chemistry C,2016,120(20):11210−11224. doi: 10.1021/acs.jpcc.6b01486
    [49]
    YAN K, YANG H, HUANG S, et al. A sulfonated chitooligosaccharide modified silica material for hydrophilic interaction liquid chromatography and its chromatographic evaluation[J]. Analytical Methods,2018,10(10):1258−1265. doi: 10.1039/C8AY00070K
    [50]
    RBAA M, BENHIBA F, HSSISOU R, et al. Green synthesis of novel carbohydrate polymer chitosan oligosaccharide grafted on d-glucose derivative as bio-based corrosion inhibitor[J]. Journal of Molecular Liquids,2021,322:114549. doi: 10.1016/j.molliq.2020.114549
    [51]
    田金花, 杨华, 迟光伟, 等. 壳聚糖和壳寡糖的磷酸化研究[J]. 化学研究与应用,2010,22(5):554−558. [TIAN Jinhua, YANG Hua, CHI Guangwei, et al. Study on the phosphorylation of chitosan and chitooligosaccharides[J]. Chemical Research and Application,2010,22(5):554−558. doi: 10.3969/j.issn.1004-1656.2010.05.006
    [52]
    莫宇星, 卢瑞, 田金花, 等. 壳寡糖和磷酸化壳寡糖对Cu(Ⅱ)的络合和缓释性能[J]. 化学研究,2016,27(6):767−770. [MO Yuxing, LU Rui, TIAN Jinhua, et al. Complexation reaction and sustained release of chitooligosaccharides and phosphorylated chitooligosaccharides with copper ion[J]. Chemical Research,2016,27(6):767−770.
    [53]
    宋玥, 林强. 磷酸化壳寡糖制备工艺研究[J]. 安徽农业科学,2010,38(1):48−50. [SONG Yue, LIN Qiang. Study on the preparation of phosphorylated chitosan oligosaccharide[J]. Journal of Anhui Agricultural Sciences,2010,38(1):48−50. doi: 10.3969/j.issn.0517-6611.2010.01.019
    [54]
    VIKØREN MO I, FENG Y, ØKSNES DALHEIM M, et al. Activation of enzymatically produced chitooligosaccharides by dioxyamines and dihydrazides[J]. Carbohydrate Polymers,2020,232:115748. doi: 10.1016/j.carbpol.2019.115748
    [55]
    SCHATZ C, LECOMMANDOUX S. Polysaccharide-containing block copolymers: Synthesis, properties and applications of an emerging family of glycoconjugates[J]. Macromolecular Rapid Communications,2010,31(19):1664−1684. doi: 10.1002/marc.201000267
    [56]
    NOVOA-CARBALLAL R, MULLER A H E. Synthesis of polysaccharide-b-PEG block copolymers by oxime click[J]. Chemical Communications (Cambridge, England),2012,48(31):3781−3783. doi: 10.1039/c2cc30726j
    [57]
    蒋艳荣, 张振海, 叶羽苗, 等. 黄芩苷-壳寡糖复合物的制备及其表征[J]. 中国中药杂志,2014,39(4):648−652. [JIANG Yanrong, ZHANG Zhenhai, YE Yumiao, et al. Preparation of baicalin-chitooligosaccharide compound and its characterization[J]. Chinese Journal of Chinese Materia Medica,2014,39(4):648−652.
    [58]
    郑虎哲, CHOI Jihye, SEONG Giun, 等. 苹果多酚-壳寡糖微胶囊的制备表征及释放特性(英文)[J]. 农业工程学报, 2020, 36(14): 281−289.

    ZHENG Huzhe, CHOI Jihye, SEONG Giun, et al. Preparation, characterization and health benefit functions of unripe apple polyphenols-chitooligosaccharides microcapsule[J]. Trans-actions of the Chinese Society of Agricultural Engineering (Transactions of the CSAE), 2020, 36(14): 281−289.
    [59]
    何文, 刘贝, 郭咸希. 不同取代度的寡聚精氨酸壳聚糖的合成与鉴定[J]. 安徽医药,2014,18(5):826−829. [HE Wen, LIU Bei, GUO Xianxi. Synthesis and characterization of chitosan modified nonaarginine with different degrees of substitution[J]. Anhui Medical and Pharmaceutical Journal,2014,18(5):826−829. doi: 10.3969/j.issn.1009-6469.2014.05.010
    [60]
    杜金风, 郝红元, 张岐, 等. 壳聚糖钙/锌配位降解产物的GFC及清除O2-·研究[J]. 分子科学学报,2006,22(6):376−380. [DU Jinfeng, HAO Hongyuan, ZHANG Qi, et al. Formation of Ca(Ⅱ) and Zn(Ⅱ) with chitosan and the study on GFC spectra of oligosaccharides by oxidizing degradation and their reactivity of scavenging active oxygen[J]. Journal of Molecular Science,2006,22(6):376−380. doi: 10.3969/j.issn.1000-9035.2006.06.004
    [61]
    HYEON-HO P, SEOK-CHUN K, GUN-WOO O, et al. Characterization and biological activity of PVA hydrogel containing chitooligosaccharides conjugated with gallic acid[J]. Carbohydrate Polymers,2018,198:197−205. doi: 10.1016/j.carbpol.2018.06.070
    [62]
    童春义, 肖苏尧, 王贝, 等. 壳寡糖-硒纳米植物营养调节剂的研制与应用[J]. 湖南大学学报(自然科学版),2008(10):60−64. [TONG Chunyi, XIAO Suyao, WANG Bei, et al. Preparation and application of chitooligosaccharides-selenium nanoparticles for plant nutrition regulator[J]. Journal of Hunan University (Natural Sciences),2008(10):60−64.
    [63]
    BOBBILI K B, SINGN B, NARAHARI A, et al. Chitooligosaccharide binding to CIA17 (Coccinia indica agglutinin). Thermodynamic characterization and formation of higher order complexes[J]. International Journal of Biological Macromolecules,2019,137:774−782. doi: 10.1016/j.ijbiomac.2019.06.211
    [64]
    BOBBILI K B, DATTA D, MONDAL S, et al. Purification, chitooligosaccharide binding properties and thermal stability of CIA24, a new PP2-like phloem exudate lectin from ivy gourd (Coccinia indica)[J]. International Journal of Biological Macromolecules,2018,110:588−597. doi: 10.1016/j.ijbiomac.2018.01.001
    [65]
    NAREDDY P K, BOBBILI K B, SWAMY M J. Purification, physico-chemical characterization and thermodynamics of chitooligosaccharide binding to cucumber (Cucumis sativus) phloem lectin[J]. International Journal of Biological Macromolecules,2017,95:910−919. doi: 10.1016/j.ijbiomac.2016.10.078
    [66]
    NARAHARI A, SINGLA H, NAREDDY P K, et al. Isothermal titration calorimetric and computational studies on the binding of chitooligosaccharides to pumpkin (Cucurbita maxima) phloem exudate lectin[J]. The Journal of Physical Chemistry B,2011,115(14):4110−4117. doi: 10.1021/jp110468n
    [67]
    DONG Z, WANG Y, WANG C, et al. Cationic Peptidopolysaccharide with an intrinsic AIE effect for combating bacteria and multicolor imaging[J]. Advanced Healthcare Materials,2020:2000419.
    [68]
    LI C Y, HUANG Z L, DONG L, et al. Improvement of enzymological properties of pepsin by chemical modification with chitooligosaccharides[J]. International Journal of Biological Macromolecules,2018,118:216−227. doi: 10.1016/j.ijbiomac.2018.06.060
    [69]
    LI C. Effects of chemical modification by chitooligosaccharide on enzyme activity and stability of yeast beta-D-fructofuranosidase[J]. Enzyme Microb Technol,2014,64-65:24−32. doi: 10.1016/j.enzmictec.2014.06.005
    [70]
    ZHAO M, MA A, HE H, et al. Desalted duck egg white peptides-chitosan oligosaccharide copolymers as calcium delivery systems: Preparation, characterization and calcium release evaluation in vitro and vivo[J]. Food Research International,2020,131:108974. doi: 10.1016/j.foodres.2019.108974
    [71]
    ZHU B, HOU T, HE H. Calcium-binding casein phosphopeptides-loaded chitosan oligosaccharides core-shell microparticles for controlled calcium delivery: Fabrication, characterization, and in vivo release studies[J]. International Journal of Biological Macromolecules,2020,154:1347−1355. doi: 10.1016/j.ijbiomac.2019.11.014
    [72]
    陈胜杰. 壳寡糖—细菌纤维素的制备及体外生物相容性评价[D]. 海口: 海南大学, 2012.

    CHEN Shengjie. Preparation of chitosan oligosaccharides/bacterial cellulose and evaluation of its biocompatibility in vitro[D]. Haikou: Hainan University, 2012.
    [73]
    NAN Y, RENPENG D, FANGKUN Z, et al. Characterization of antibacterial bacterial cellulose composite membranes modified with chitosan or chitooligosaccharide[J]. Carbohydrate Polymers,2020,229:115520. doi: 10.1016/j.carbpol.2019.115520
    [74]
    周中凯, 李莹, 王俊轩, 等. 壳寡糖、抗性淀粉及其复合物对高脂饮食大鼠粪便中脂质成分的差异性[J]. 食品科技,2016,41(8):79−83. [ZHOU Zhongkai, LI Ying, WANG Junxuan, et al. Differences effect of lipid composition in the feces of high fat rat with chitosan oligosaccharides, resistant starch and its compound[J]. Food Science and Technology,2016,41(8):79−83.
    [75]
    李莹, 周中凯, 王俊轩. 壳寡糖、抗性淀粉及其复合物对高脂饮食大鼠脂代谢及肠道菌群的影响[J]. 中国食品添加剂,2016(11):94−101. [LI Ying, ZHUO Zhongkai, WANG Junxuan. Chitosan oligosaccharide, resistant starch and its compound on lipid metabolism and intestinal flora in high-diet rats[J]. China Food Additives,2016(11):94−101. doi: 10.3969/j.issn.1006-2513.2016.11.007
    [76]
    周中凯, 王俊轩, 李莹. 壳寡糖修饰抗性淀粉的物化与消化特性研究[J]. 粮食与油脂,2017,30(5):16−19. [ZHOU Zhongkai, WANG Junxuan, LI Ying. Study on physicochemical properties and digestion characteristics of resistant starch modified by chitosan oligosaccharide[J]. Food and Oils,2017,30(5):16−19. doi: 10.3969/j.issn.1008-9578.2017.05.005
    [77]
    ZHANG J, CHEN X G, HUANG L, et al. Self-assembled polymeric nanoparticles based on oleic acid-grafted chitosan oligosaccharide: Biocompatibility, protein adsorption and cellular uptake[J]. Journal of Materials Science-Materials in Medicine,2012,23(7):1775−1783. doi: 10.1007/s10856-012-4651-1
    [78]
    刘金虎. 磷酸壳寡糖脂质体的构建及用于骨肉瘤治疗的体内外研究[D]. 烟台: 烟台大学, 2019.

    LIU Jinhu. Construction of phosphate chitosan-oligosaccharide liposomes and in vitro and in vivo research for osteosarcoma treatment[D]. Yantai: Yantai University, 2019.
    [79]
    李樱红, 胡富强, 袁弘. 壳寡糖硬脂酸接枝物纳米粒的制备及其体外释放[J]. 中国药学杂志,2005,40(14):1083−1086. [LI Yinghong, HU Fuqiang, YUAN Hong. Preparation and release profiles of chitosan oligosaccharide grafted stearic acid nanoparticles in vitro[J]. Chinese Pharmaceutical Journal,2005,40(14):1083−1086. doi: 10.3321/j.issn:1001-2494.2005.14.014
    [80]
    CAO R, LI X, ZHOU Z, et al. Synthesis and biophysical analysis of naringin-chitooligosaccharide complex[J]. Natural Product Research,2019,6:1−7.
    [81]
    CAO R, MA Q, FU Y, et al. Preparation, evaluation and characterization of rutin-chitooligosaccharide complex[J]. Plant Foods for Human Nutrition,2019,74(3):328−333. doi: 10.1007/s11130-019-00740-y
    [82]
    XIN C, YAO X, DU B, et al. Stearic acid-grafted chitooligosaccharide nanomicelle system with biocleavable gadolinium chelates as a multifunctional agent for tumor imaging and drug delivery[J]. Pharmaceutical Research,2018,36(1):10. doi: 10.1007/s11095-018-2530-2
    [83]
    LUO Q, ZHAO J, ZHANG X, et al. Nanostructured lipid carrier (NLC) coated with chitosan oligosaccharides and its potential use in ocular drug delivery system[J]. International Journal of Pharmaceutics,2011,403(1-2):185−191. doi: 10.1016/j.ijpharm.2010.10.013
    [84]
    WANG D, LI S, TAN X, et al. Engineering of stepwise-targeting chitosan oligosaccharide conjugate for the treatment of acute kidney injury[J]. Carbohydrate Polymers,2021,256:117556. doi: 10.1016/j.carbpol.2020.117556
    [85]
    黄佩文, 陈苏萍, 魏晓红, 等. 壳寡糖/水杨酸接枝物纳米粒用于释放阿霉素的研究[J]. 中国现代应用药学,2014,31(1):61−66. [HUANG Peiwen, CHEN Suping, WEI Xiaohong, et al. Chitosan oligosaccharide/salicylic acid nanoparticles for doxorubicin delivery[J]. China Modern Applied Pharmacy,2014,31(1):61−66.
    [86]
    ZHANG J, HAN J, ZHANG X, et al. Polymeric nanoparticles based on chitooligosaccharide as drug carriers for co-delivery of all-trans-retinoic acid and paclitaxel.[J]. Carbohydrate Polymers,2015,129(9):25−34.
    [87]
    LIANG Z, GONG T, SUN X, et al. Chitosan oligomers as drug carriers for renal delivery of zidovudine[J]. Carbohydrate Polymers,2012,87(3):2284−2290. doi: 10.1016/j.carbpol.2011.10.060
    [88]
    YANG S, LIN F, TSAI K, et al. Folic acid-conjugated chitosan nanoparticles enhanced protoporphyrin IX accumulation in colorectal cancer cells[J]. Bioconjugate Chemistry,2010,21(4):679−689. doi: 10.1021/bc9004798
    [89]
    王荣民, 裴菲, 何玉凤, 等. 低聚壳聚糖负载金属卟啉配合物的制备及生物活性研究[J]. 化学研究与应用,2012,24(2):278−281. [WANG Rongmin, PEI Fei, HE Yufeng, et al. Preparation and biological activitiy of chitooligosaccharide supported porphyrins metallic complexes[J]. Chemical Research and Application,2012,24(2):278−281. doi: 10.3969/j.issn.1004-1656.2012.02.022
    [90]
    RONG M W, JING F S, YU F H, et al. Conjugation of chitooligosaccharide-5-fluorouracil with bovine serum albumin[J]. Chinese Chemical Letters,2006(11):1495−1498.
    [91]
    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. [LI Yuxin, LI Shangyong, CHEN Xuehong. The analysis method of oligochitosan and its application in crop industry[J]. Rural Economy and Technology,2020,31(8):78−80. doi: 10.3969/j.issn.1007-7103.2020.08.043
    [92]
    SCHLOFFEL M A, KASBAUER C, GUST A A. Interplay of plant glycan hydrolases and LysM proteins in plant—bacteria interactions[J]. International Journal of Medical Microbiology,2019,309(3-4):252−257. doi: 10.1016/j.ijmm.2019.04.004
    [93]
    CHEN W, YANG Q. Development of novel pesticides targeting insect chitinases: A minireview and perspective[J]. Journal of Agricultural and Food Chemistry,2020,68(16):4559−4565. doi: 10.1021/acs.jafc.0c00888
    [94]
    JUN Z, SONG L, YUKUN Q, et al. Preparation, characterization, and antifungal evaluation of a new type of aminourea chitooligosaccharide derivatives[J]. Journal of Oceanology and Limnology,2020(3):841−850.
    [95]
    高晓冉, 刘程惠, 陈立国, 等. 壳寡糖与茶多酚复合保鲜剂对冷鲜牛肉的保鲜效果[J]. 食品与发酵工业,2019,45(11):172−178. [GAO Xiaoran, LIU Chenghui, CHEN Liguo, et al. Preservative effects of chitosan oligosaccharide and tea polyphenol together on chilled beef[J]. Food and Fermentation Industries,2019,45(11):172−178.
    [96]
    CHANG Y, SUNG W, CHEN J. Effect of different molecular weight chitosans on the mitigation of acrylamide formation and the functional properties of the resultant Maillard reaction products[J]. Food Chemistry,2016,199(5):581−589.
    [97]
    SHYU Y S , HSIAO H I , FANG J Y, et al. Effects of dark brown sugar replacing sucrose and calcium carbonate, chitosan, and chitooligosaccharide addition on acrylamide and 5-hydroxymethylfurfural mitigation in brown sugar cookies[J]. Processes,2019,7(6):360. doi: 10.3390/pr7060360
    [98]
    SEONG J S, MID E Y, SOO N P. Surfactant-stable and pH-sensitive liposomes coated with N-succinyl-chitosan and chitooligosaccharide for delivery of quercetin[J]. Carbohydrate Polymers,2018,181:659−667. doi: 10.1016/j.carbpol.2017.11.098
    [99]
    王亚珍, 谢晶, 李立, 等. 壳寡糖对壳聚糖-明胶-壳寡糖三元复合膜的性能影响研究[J]. 食品工业科技,2015,36(8):134−137. [WANG Yazhen, XIE Jing, LI Li, et al. Effect of chitosan oligosaccharide on properties of chitosan-gelatin-chitosan oligosaccharide ternary composite films[J]. Science and Technology of Food Industry,2015,36(8):134−137.
    [100]
    CHEN S, LUO C, WEN W, et al. Fabrication, antibacterial activity and cytocompatibility of quaternary ammonium chitooligosaccharide functionalized polyurethane membrane via polydopamine adhesive layer[J]. Materials Science & Engineering C,2018,93:319−331.
    [101]
    BU X, PEI J, ZHANG F, et al. The hydration mechanism and hydrogen bonding structure of 6-carboxylate chitooligosaccharides superabsorbent material prepared by laccase/TEMPO oxidation system[J]. Carbohydrate Polymers,2018,188:151−158. doi: 10.1016/j.carbpol.2018.01.099
  • Cited by

    Periodical cited type(4)

    1. 张莉琼,皮阳雪,徐海芳,李彭,李新芳,杨原智,陈丽军. 聚乙烯醇包装薄膜的制备及其抗菌性能研究. 印刷与数字媒体技术研究. 2024(05): 156-163 .
    2. 汪明莹,窦西琳,丁兆阳,谢晶. 金属有机框架材料在食品包装中的应用. 食品科学. 2023(03): 341-349 .
    3. 徐群娜,李娇娇,丁杨,马建中,李鹏妮. 基于生物质模板制备ZIF-8及抗菌性能. 精细化工. 2023(07): 1470-1477+1496 .
    4. 孔文泉,魏凯,赵耀,闫宝林,张优. 金属有机框架材料及其涂层在生物抗菌领域的应用研究进展. 稀有金属材料与工程. 2023(07): 2623-2638 .

    Other cited types(3)

Catalog

    Article Metrics

    Article views (619) PDF downloads (94) Cited by(7)

    /

    DownLoad:  Full-Size Img  PowerPoint
    Return
    Return