Synthesis and Antifungal Activities of Chitosan Oligosaccharide Thiosemicarbazone Schiff Base Cu(Ⅱ) Complex

doi:10.11944/j.issn.1000-0518.2019.05.180284

Chinese Journal of Applied Chemistry ›› 2019, Vol. 36 ›› Issue (5): 500-508.DOI: 10.11944/j.issn.1000-0518.2019.05.180284

• Full Papers • Previous Articles Next Articles

Synthesis and Antifungal Activities of Chitosan Oligosaccharide Thiosemicarbazone Schiff Base Cu(Ⅱ) Complex

BAO Jinping,FAN Sufang,YANG Guoyu(),WANG Zhimin,WANG Ying,LIU Xiaohua,XU Cuilian()

College of Sciences,Henan Agricultural University,Zhengzhou 450002,China

Received:2018-09-03 Accepted:2019-01-03 Published:2019-05-01 Online:2019-05-06
Contact: YANG Guoyu,XU Cuilian
Supported by:
Supported by the Science and Technology Tackling Key Project of Henan Province(No.1521021100700, No.112101110200);Project of Subsidized Youth Backbone Teachers in Henan Higher Education Institutions(No.2014GGJS-083);National Undergraduate Training Program for Innovation and Entrepreneurship(No.201610466022)

Abstract

Abstract:

Chitosan oligosaccharide thiosemicarbazide was prepared in one-pot. Then chitosan oligosaccharide thiosemicarbazone was synthesized by the reaction of chitosan thiosemicarbazide with 2-pyridinecarboxaldehyde. Chitosan oligosaccharide thiosemicarbazone Cu(Ⅱ) complex was thus obtained by the reaction of chitosan thiosemicarbazide with Cu(Ⅱ) salt. The structure of the synthesized compounds was characterized by infrared(IR) spectroscopy, ultraviolet-visible(UV-Vis) spectroscopy, nuclear magnetic resonance(NMR), inductively coupled plasma(ICP), and thermogravimetry-differential thermal analysis(TG-DTA). The antifungal behaviors of chitosan oligosaccharide and its derivatives against three crop-threatening pathogenic fungi:Phytophthora capsici(P.capsici), Phytophthora nicotianae(P.nicotianae), Fusarium graminearum(F.graminearum) were investigated by mycelial growth rate method in vitro. The results show that the inhibitory index of chitosan thiosemicarbazone Cu(Ⅱ) complex against P.capsici, P.nicotianae, F.graminearum is 74.19%, 56.60%, 66.60%, respectively, and is higher than those observed with chitosan.

Key words: chitosan oligosaccharide, thiosemicarbazide, Cu(Ⅱ) complex, antifungal activity

BAO Jinping, FAN Sufang, YANG Guoyu, WANG Zhimin, WANG Ying, LIU Xiaohua, XU Cuilian. Synthesis and Antifungal Activities of Chitosan Oligosaccharide Thiosemicarbazone Schiff Base Cu(Ⅱ) Complex[J]. Chinese Journal of Applied Chemistry, 2019, 36(5): 500-508.

References

[1]	XUE Chunsheng,HE Ruihong,LI Xinghai,et al. Inhibition Effect of Cycloakylsulfonamide on Phytophthora capsici[J]. Plant Prot,2016,42(1):214-218(in Chinese). 薛春生,何瑞玒,李兴海,等. 环烷基磺酰胺类化合物对辣椒疫霉的抑制作用[J]. 植物保护,2016,42(1):214-218.
[2]	HE Wei,ZHANG Hui,WANG Ying.Rapid Identification of Resistance to Phytophthora capsici in Pepper[J]. Plant Prot,2018,44(2):145-148(in Chinese). 赫卫,张慧,王莹. 辣椒对疫霉抗性的快速鉴定[J]. 植物保护,2018,44(2):145-148.
[3]	CUI Linkai,ZHAO Shanshan,GAO Pengfei,et al. Genetic Structure Analysis of Phytophthora nicotianae Population in Henan Province by SSR Marker[J]. Acta Tabaca Sin,2018,24(5):51-56(in Chinese). 崔林开,赵珊珊,高鹏飞,等. 河南省烟草黑胫病菌群体遗传结构的SSR分析[J]. 中国烟草学报,2018,24(5):51-56.
[4]	ZONG Ying,HAO Yueju,LIU Yang,et al. Study on the Inhibitory Effect of Bacillus velezensis on Fusarium graminearum[J]. J Nucl Agric Sci,2018,32(2):310-317(in Chinese). 宗英,赵月菊,刘阳,等. 一株贝莱斯芽孢杆菌抑制禾谷镰刀菌的研究[J]. 核农学报,2018,32(2):310-317.
[5]	CHEN Zebin,XIA Zhenyuan,LEI Liping,et al. Screening of Endophytic Beneficial Bacteria to Tobacco black shank Control and Its Bacteriostasis[J]. Acta Tabaca Sin,2013,19(5):112-117(in Chinese). 陈泽斌,夏振远,雷丽萍,等. 防治烟草黑胫病有益内生细菌的筛选及其抑菌作用[J]. 中国烟草学报,2013,19(5):112-117.
[6]	CHENG Genwu,LIU Ying,QI Zhiqiu,et al. Activity of Azoxystrobin on Several Plant Pathogenic Fungi[J]. Chinese J Pestic,2005,44(4):190-191(in Chinese). 程根武,刘赢,祁之秋,等. 嘧菌酯对几种植物病原真菌的室内活性测定[J]. 农药,2005,44(4):190-191.
[7]	XU Liangzhong,LI Huijing,ZHANG Shusheng.Progress of 1,2,4-Triazole Fungicides[J]. J Qingdao Inst Chem Technol,2000,21(3):201-205(in Chinese). 许良忠,李惠静,张书圣. 含1,2,4-三氮唑类杀菌剂的研究进展[J]. 青岛化工学院学报,2000,21(3):201-205.
[8]	Chiena R C,Tsung Y D,Leun M J.Antimicrobial and Antitumor Activities of Chitosan from Shiitake Stipes, Compared to Commercial Chitosan from Crab Shells[J]. Carbohydr Polym,2016,138:259-264.
[9]	Yuan G F,Chen X,Li D.Chitosan Films and Coatings Containing Essential Oils:The Antioxidant and Antimicrobial Activity, and Application in Food Systems[J]. Food Res Int,2016,89:117-128.
[10]	Verlee A,Mincke V S,Stevens C.Recent Developments in Antibacterial and Antifungal Chitosan and Its Derivatives[J]. Carbohydr Polym,2017,164:268-283.
[11]	Li Q,Tan W Q,Zhang C L,et al. Novel Triazolyl-Functionalized Chitosan Derivatives with Different Chain Lengths of Aliphatic Alcohol Substituent: Design, Synthesis, and Antifungal Activity[J]. Carbohydr Res,2015,418(11):44-49.
[12]	Li Q,Tan W Q,Zhang C L,et al. Synthesis of Water Soluble Chitosan Derivatives with Halogeno-1,2,3-Triazole and Their Antifungal Activity[J]. Int J Biol Macromol,2016,91:623-629.
[13]	Jia R X,Duan Y F,Fang Q,et al. Pyridine-Grafted Chitosan Derivative as an Antifungal Agent[J]. Food Chem,2016,196:381-387.
[14]	Salama H E,Saad G R,Sabaa M W.Synthesis, Characterization and Biological Activity of Schiff Bases Based on Chitosan and Arylpyrazole Moiety[J]. Int J Biol Macromol,2015,79:996-1003.
[15]	Qin Y K,Xing R E,Liu S,et al. Synthesis and Antifungal Properties of (4-Tolyloxy)-Pyrimidyl-α-Aminophosphonates Chitosan Derivatives[J]. Int J Biol Macromol,2014,63:83-91.
[16]	LIU Haibin,LÜ Ping,PAN Ningning,et al. Synthesis and In vitro Anticancer Activity of Novel Quinazoline Derivatives Containing Thiosemicarbazone Structure[J]. Chem J Chinese Univ,2014,35(5):981-988(in Chinese). 刘海彬,吕萍,潘宁宁,等. 新型含缩氨基硫脲结构的喹唑啉衍生物的合成及体外抗癌活性[J]. 高等学校化学学报,2014,35(5):981-988.
[17]	WANG Zhen,DONG Wei,XU Yan,et al. Synthesis of Substituted Benzylidene Hydrazinecarbothioamide(Hydrazinecarboxamide, Nitrohydrazinecarboximidamide) and Their Inhibitory Activity on Tyrosinase of Diamondback Moth Plutella Xylostella(L.)[J]. Chinese J Pestic Sci,2010,12(3):264-268(in Chinese). 王振,董玮,徐焱,等. 取代苯甲醛缩氨基硫脲(脲、硝基胍)类化合物的合成及其对小菜蛾酪氨酸酶的抑制活性[J]. 农药学学报,2010,12(3):264-268.
[18]	MIN Rui,FAN Xiaorui,ZHOU Pan,et al. Synthesis, Crystal Structure, DNA Interaction and Antitumor Activity of Nickel Complex with Quinoline-2-Carboxaldehyde N4-Methyl-Thiosemicarbazone[J]. Chinese J Inorg Chem,2014,30(8):1771-1777(in Chinese). 闵睿,范晓瑞,周攀,等. 缩氨基硫脲Ni(Ⅱ)配合物的合成、晶体结构、DNA相互作用及抗肿瘤活性研究[J]. 无机化学学报,2014,30(8):1771-1777.
[19]	Kumar S,Hansda A,Chandra A,et al. Co(Ⅱ), Ni(Ⅱ), Cu(Ⅱ) and Zn(Ⅱ) Complexes of Acenaphthoquinone 3-(4-Benzylpiperidyl)thiosemicarbazone:Synthesis, Structural, Electrochemical and Antibacterial Studies[J]. Polyhedron,2017,134:11-21.
[20]	Khan S A,Asiri A M,Al-amry K,et al. Synthesis, Characterization, Electrochemical Studies, and In Vitro Antibacterial Activity of Novel Thiosemicarbazone and Its Cu(Ⅱ), Ni(Ⅱ), and Co(Ⅱ) Complexes[J]. Sci World J,2014,592375:1-9.
[21]	Qin Y K,Xing R G,Liu S,et al. Novel Thiosemicarbazone Chitosan Derivatives:Preparation, Characterization, and Antifungal Activity[J]. Carbohydr Polym,2012,87(4):2664-2670.
[22]	Yang G Y,Jin Q,Xu C L,et al. Synthesis, Characterization and Antifungal Activity of Coumarin- Functionalized Chitosan Derivatives[J]. Int J Biol Macromol,2018,106:179-184.
[23]	Qin Y K,Liu S,Xing R E,et al. Synthesis and Antifungal Evaluation of (1,2,3-triazol-4-yl)methyl Nicotinate Chitosan[J]. Int J Biol Macromol,2013,61:58-62.
[24]	Kittur F S,Prashanth K V H,Sankar K U,et al. Characterization of Chitin, Chitosan and Their Carboxymethyl Derivatives by Differential Scanning Calorimetry[J]. Carbohydr Polym,2002,49(2):185-193.

Synthesis and Antifungal Activities of Chitosan Oligosaccharide Thiosemicarbazone Schiff Base Cu(Ⅱ) Complex

RichHTML

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Mou-Cui LI, Yang-Ming DONG, Ying-Hui REN, Hai-Xia MA, Le QI. Synthesis， Antifungal Activity and Molecular Docking Study of 1，2，4-Triazole Bis-Schiff Base Derivatives [J]. Chinese Journal of Applied Chemistry, 2023, 40(1): 116-125.
[2]	JIANG Wen, ZHOU Zhen, SHI Yexin, TAO Renyou, ZHANG Guiluo, ZHOU Xiaohua, WANG Dan. Preparation and Characterization of Chitosan Oligo-Saccharide-Hydrolyzed Gliadin Copolymer [J]. Chinese Journal of Applied Chemistry, 2016, 33(3): 284-292.
[3]	JIANG Wen, ZHOU Zhen, SHI Yexin, TAO Renyou, ZHANG Guiluo, ZHOU Xiaohua, WANG Dan. Preparation and Characterization of Chitosan Oligo-Saccharide-Hydrolyzed Gliadin Copolymer [J]. Chinese Journal of Applied Chemistry, 2016, 33(3): 0-0.
[4]	CHEN Yong ,WU Hankui,LONG Junfei. Synthesis and Antifungal Activity of Novel Azole Derivatives with 2',4'-Dihalobiphenyl [J]. Chinese Journal of Applied Chemistry, 2015, 32(1): 43-52.
[5]	YANG Qingcui1,2, SUN Xiaohong1,3*, LIU Yuanfa4, CHEN Bang4, SHEN Shengqiang3. Synthesis and Antifungal Activity of Schiff Bases of 5-Ethoxycarbonylmethylsulfanyl-1,2,4-triazole [J]. Chinese Journal of Applied Chemistry, 2014, 31(07): 788-792.
[6]	WU Jawei1,2, TANG Rongping1, SUO Longning1, YANG Xingkai1, WEI Taibao2, ZHOU Yanqing1,2*. Synthesis of molecular Tweezers Based on thiosemi-Carbazide and their Anion Recognition Properties  [J]. Chinese Journal of Applied Chemistry, 2011, 28(11): 1274-1279.
[7]	Qi Chuanmin, Chen Wanyi, Wang Wenjun. Synthesis and Biological Activity of 2,2-Disubstituted 5-Benzal(fural) Cyclopentanones [J]. Chinese Journal of Applied Chemistry, 1998, 0(2): 32-35.
[8]	Si Zongxing, Sun Yaqiu, Wang Haitao. Synthesis and Biological Activity of Long chain Esters of Substituted Phenyl α-Furoic Acid [J]. Chinese Journal of Applied Chemistry, 1997, 0(2): 96-98.
[9]	Wang Yulu, Wang Hong, Li Jianping, Ma Donglan, Shan Yingfang, He Fangshu. Synthesis and Antibacterial Action of 1-Substituted Phenyl-4-Hydrocarbyl Thiosemicarbazides [J]. Chinese Journal of Applied Chemistry, 1995, 0(4): 62-65.
[10]	Tian Junlian, Bi Siwei, Gao Enqing, Li Yantuan, Li Guizhi, Liu Shuxiang. Study on Biologically Active Schiff Base Complexes of Formylformic Acid with Thiosemicarbazide [J]. Chinese Journal of Applied Chemistry, 1994, 0(5): 45-48.
[11]	Zhang Ziyi, Wei Xiuying, Shi Jihong. INHIBITING EFFECT OF RADICAL POLYMERIZATION OF VINYL MONOMERS ⅩⅦ.INHIBITING EFFECTS OF 1-ACYL FORMYL-4[4′-(2,2,6,6-TETRAMETHYL PIPERIDINE)]THIOSEMICARBAZIDES ON POLYMERIZATION OF MMA [J]. Chinese Journal of Applied Chemistry, 1993, 0(3): 66-67.
[12]	Feng Xiaoming, Chen Rong, Zhang Ziyi. SYNTHESIS OF 1-PHENYLACETYL-4-AROYLTHIOSEMICAR-BAZIDES AND THEIR CYCLIZATION [J]. Chinese Journal of Applied Chemistry, 1993, 0(1): 104-106.
[13]	Feng Xiaoming, Chen Rong, Huang Guangyan, Zhang Ziyi. SYNTHESIS OF 1-(α-NAPHTHYLACETYL)-4-AROYLTHIO-SEMICARBAZIDES AND 3-(α-NAPHTHYLMETHENE)-4-AROYL-1, 2, 4-TRIAZOLINE-5-THIONES [J]. Chinese Journal of Applied Chemistry, 1992, 0(2): 89-95.
[14]	Chen Limin, Zhang Ziyi, Wu Heping, Zheng Guoyu. STUDIES ON ACYLTHIOSEMICARBAZIDES AND RELATED HETEROCYCLIC DERIVATIVES ⅩⅤ.SYNTHESIS AND ANTIBACTERIAL ACTION OF 3-(5-(3-PYRIDYL)-2H-TETRAZOL-2-YLMETHYL)-4-ARYL-1,2,4-TRIAZOL-5-ALKYLSULFIDE [J]. Chinese Journal of Applied Chemistry, 1990, 0(5): 27-33.
[15]	Zhang Ziyi, Wei Xiuying, Yang Rong, Ge Shizhen. INHIBITING EFFECTS ON THE RADICAL POLYMERIZATION OF VINYL MONOMERS Ⅻ.THE INHIBITING EFFECT OF ACYL THIOSEMICARBAZIDES AND SOME HETEROCYCLES ON POLYMERIZATION OF VAc [J]. Chinese Journal of Applied Chemistry, 1990, 0(1): 94-97.