Cite this paper:
ZHU Jun, LIU Song, QIN Yukun, XING Rong'e, YU Huahua, CHEN Xiaolin, LI Pengcheng. Preparation, characterization, and antifungal evaluation of a new type of aminourea chitooligosaccharide derivatives[J]. Journal of Oceanology and Limnology, 2020, 38(3): 841-850

Preparation, characterization, and antifungal evaluation of a new type of aminourea chitooligosaccharide derivatives

ZHU Jun1,3, LIU Song1,2, QIN Yukun1,2, XING Rong'e1,2, YU Huahua1,2, CHEN Xiaolin1,2, LI Pengcheng1,2
1 Key Laboratory of Experimental Marine Biology, Center for Ocean Mega-Science, Institute of Oceanology, Chinese Academy of Sciences, Qingdao 266071, China;
2 Laboratory for Marine Drugs and Bioproducts, Pilot National Laboratory for Marine Science and Technology(Qingdao), Qingdao 266237, China;
3 University of Chinese Academy of Sciences, Beijing 100049, China
Abstract:
Phytopathogenic fungi cause heavy negative impact on the agricultural economy, but most existing fungicides are toxic and pose a threat to both human health and environments. A green and efficient fungicide is urgently needed. Chitooligosaccharides (COSs), the degradation products of natural polysaccharide chitosan, are nontoxic and biodegradable antifungal substances. In this study, a novel type of aminourea chitooligosaccharide derivatives (AUCOS) was synthesized by successively grafting a hydrazine group and an amine-carbonyl group onto a chitooligosaccharide backbone to enhance the antifungal capability of COSs. The structures of the target compounds were identified by FTIR, 1H NMR, and 13C NMR, and the degree of substitution of each product was calculated from the results of the elemental analysis. The antifungal activities of the prepared chitooligosaccharide derivatives against Fusarium solani, Verticillium albo-atrum and Phytophthora capsici were tested in vitro. The AUCOSs had better inhibitory efficiencies against the three plant pathogen fungi than that of chitooligosaccharide, of which aminourea chitooligosaccharide 2 (AUCOS2) was the most promising antifungal compound, whose highest inhibition rates were 60.12%, 82.95%, and 85.23% against F. solani, V. albo-atrum and P. capsici, respectively. The synthesized derivatives have good application prospects in crop protection and deserve further research.
Key words:    chitooligosaccharide (COS)|aminourea|characterization|antifungal   
Received: 2019-04-10   Revised: 2019-08-22
Tools
PDF (908 KB) Free
Print this page
Add to favorites
Email this article to others
Authors
Articles by ZHU Jun
Articles by LIU Song
Articles by QIN Yukun
Articles by XING Rong'e
Articles by YU Huahua
Articles by CHEN Xiaolin
Articles by LI Pengcheng
References:
Badawy M E I, Rabea E I, Taktak N E M. 2014. Antimicrobial and inhibitory enzyme activity of N-(benzyl) and quaternary N-(benzyl) chitosan derivatives on plant pathogens. Carbohydrate Polymers, 111:670-682.
Badawy M E I, Rabea E I. 2011. A biopolymer chitosan and its derivatives as promising antimicrobial agents against plant pathogens and their applications in crop protection.International Journal of Carbohydrate Chemistry, 2011:460381.
Barchenger D W, Lamour K H, Bosland P W. 2018. Challenges and strategies for breeding resistance in Capsicum annuum to the multifarious pathogen, Phytophthora capsici. Frontiers in Plant Science, 9:628.
Benhabiles M S, Salah R, Lounici H, Drouiche N, Goosen M F A, Mameri N. 2012. Antibacterial activity of chitin, chitosan and its oligomers prepared from shrimp shell waste. Food Hydrocolloids, 29(1):48-56.
Coleman J J. 2016. The Fusarium solani species complex:ubiquitous pathogens of agricultural importance.Molecular Plant Pathology, 17(2):146-158.
Deketelaere S, Tyvaert L, Franca S C, Höfte M. 2017. Desirable traits of a good biocontrol agent against verticillium wilt.Frontiers in Microbiology, 8:1 186.
Fan Z Q, Qin Y K, Liu S, Xing R E, Yu H H, Chen X L, Li K C, Li P C. 2018. Synthesis, characterization, and antifungal evaluation of diethoxyphosphoryl polyaminoethyl chitosan derivatives. Carbohydrate Polymers, 190:1-11.
Guo Z Y, Xing R E, Liu S, Zhong Z M, Ji X, Wang L, Li P C. 2007. The influence of the cationic of quaternized chitosan on antifungal activity. International Journal of Food Microbiology, 118(2):214-217.
Hussain I, Singh T, Chittenden C. 2012. Preparation of chitosan oligomers and characterization:their antifungal activities and decay resistance. Holzforschung, 66(1):119-125.
Je J Y, Kim S K. 2006. Chitosan derivatives killed bacteria by disrupting the outer and inner membrane. Journal of Agricultural and Food Chemistry, 54(18):6 629-6 633.
Kim J Y, Lee J K, Lee T S, Park W H. 2003. Synthesis of chitooligosaccharide derivative with quaternary ammonium group and its antimicrobial activity against Streptococcus mutans. International Journal of Biological Macromolecules, 32(1-2):23-27.
Kong M, Chen X G, Xing K, Park H J. 2010. Antimicrobial properties of chitosan and mode of action:a state of the art review. International Journal of Food Microbiology, 144(1):51-63.
Li X F, Feng X Q, Yang S, Fu G Q, Wang T P, Su Z X. 2010.Chitosan kills Escherichia coli through damage to be of cell membrane mechanism. Carbohydrate Polymers, 79(3):493-499.
Li Y, Liu S, Qin Y K, Xing R E, Chen X L, Li K C, Li P C. 2016. Synthesis of novel pyrimethanil grafted chitosan derivatives with enhanced antifungal activity. Biomed Research International, 2016:8196960.
Liu B, Wang X Y, Pang C S, Luo J W, Luo Y Q, Sun R C. 2013.Preparation and antimicrobial property of chitosan oligosaccharide derivative/rectorite nanocomposite. Carbohydrate Polymers, 92(2):1 078-1 085.
Liu W X, Qin Y K, Liu S, Xing R E, Yu H H, Chen X L, Li K C, Li P C. 2017. Synthesis, characterization and antifungal efficacy of C-coordinated O-carboxymethyl chitosan Cu(II) complexes. Carbohydrate Polymers, 160:97-105.
Liu W X, Qin Y K, Liu S, Xing R E, Yu H H, Chen X L, Li K C, Li P C. 2018. Synthesis, characterization and antifungal efficacy of chitosan derivatives with triple quaternary ammonium groups. International Journal of Biological Macromolecules, 114:942-949.
Meng X T, Xing R E, Liu S, Yu H H, Li K C, Qin Y K, Li P C. 2012. Molecular weight and pH effects of aminoethyl modified chitosan on antibacterial activity in vitro.International Journal of Biological Macromolecules, 50(4):918-924.
Park P J, Je J Y, Byun H G, Moon S H, Kim S K. 2004.Antimicrobial activity of hetero-chitosans and their oligosaccharides with different molecular weights.Journal of Microbiology and Biotechnology, 14(2):317-323.
Qin Y K, Liu S, Xing R E, Yu H H, Li K C, Meng X T, Li R F, Li P C. 2012. Synthesis and characterization of dithiocarbamate chitosan derivatives with enhanced antifungal activity. Carbohydrate Polymers, 89(2):388-393.
Qin Y K, Xing R E, Liu S, Yu H H, Li K C, Hu L F, Li P C. 2014. Synthesis and antifungal properties of (4-tolyloxy)-pyrimidyl-α-aminophosphonates chitosan derivatives.International Journal of Biological Macromolecules, 63:83-91.
Rabea E I, Badawy M E T, Stevens C V, Smagghe G, Steurbaut W. 2003. Chitosan as antimicrobial agent:applications and mode of action. Biomacromolecules, 4(6):1 457-1 465.
Rahman H, Hjeljord L G, Aam B B, Sørlie M, Tronsmo A. 2015. Antifungal effect of chito-oligosaccharides with different degrees of polymerization. European Journal of Plant Pathology, 141(1):147-158.
Seyfarth F, Schliemann S, Elsner P, Hipler U C. 2008.Antifungal effect of high- and low-molecular-weight chitosan hydrochloride, carboxymethyl chitosan, chitosan oligosaccharide and N-acetyl-D-glucosamine against Candida albicans, Candida krusei and Candida glabrata.International Journal of Pharmaceutics, 353(1-2):139-148.
Song Y P, Miao F P, Liu X H, Ji N Y. 2019. Responses of marine-derived Trichoderma fungi to seawater and their potential antagonistic behaviour. Journal of Oceanology and Limnology, 37(2):525-534.
Song Y P, Shi Z Z, Miao F P, Fang S T, Yin X L, Ji N Y. 2018.TricholuminA, a highly transformed ergosterol derivative from the alga-endophytic fungus Trichoderma asperellum.Organic Letters, 20(19):6 306-6 309.
Sun S L, An Q Z, Li X, Qian L Y, He B H, Xiao H N. 2010.Synergistic effects of chitosan-guanidine complexes on enhancing antimicrobial activity and wet-strength of paper. Bioresource Technology, 101(14):5 693-5 700.
Tan W Q, Zhang J J, Luan F, Wei L J, Chen Y, Dong F, Li Q, Guo Z Y. 2017. Design, synthesis of novel chitosan derivatives bearing quaternary phosphonium salts and evaluation of antifungal activity. International Journal of Biological Macromolecules, 102:704-711.
Tripathi P, Dubey N K. 2004. Exploitation of natural products as an alternative strategy to control postharvest fungal rotting of fruit and vegetables. Postharvest Biology and Technology, 32(3):235-245.
Vinšová J, Vavříková E. 2011. Chitosan derivatives with antimicrobial, antitumour and antioxidant activities-a review. Current Pharmaceutical Design, 17(32):3 596-3 607.
Xia W S, Liu P, Zhang J L, Chen J. 2011. Biological activities of chitosan and chitooligosaccharides. Food Hydrocolloids, 25(2):170-179.
Yuan B, Xu P Y, Zhang Y J, Wang P P, Yu H, Jiang J H. 2014.Synthesis of biocontrol macromolecules by derivative of chitosan with surfactin and antifungal evaluation.International Journal of Biological Macromolecules, 66:7-14.
Yue L, Li J R, Chen W W, Liu X L, Jiang Q X, Xia W S. 2017.Geraniol grafted chitosan oligosaccharide as a potential antibacterial agent. Carbohydrate Polymers, 176:356-364.
Zhang Y B, Dang Q F, Liu C S, Yan J Q, Cha D S, Liang S N, Li X L, Fan B. 2017. Synthesis, characterization, and evaluation of poly(aminoethyl) modified chitosan and its hydrogel used as antibacterial wound dressing.International Journal of Biological Macromolecules, 102:457-467.
Zhao X, He J X, Zhan Y Z. 2009. Synthesis and characterization of chitosan biguanidine hydrochloride under microwave irradiation. Polymer Journal, 41(12):1 030-1 035.
Copyright © Haiyang Xuebao