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Journal of Zhejiang University (Science Edition)  2023, Vol. 50 Issue (3): 346-350    DOI: 10.3785/j.issn.1008-9497.2023.03.012
Chemistry     
Conversion of anionic derivatives of fermented cellulose and evaluation of their antifungal effect
Yanli CUI1(),Shunyao LI2,Tianyu ZHANG3,Minyan ZHANG1,Xiangxiang BAO1,Yangyi MAO1
1.Department of Chemistry,Zhejiang University,Hangzhou 310058,China
2.Zhengzhou College of Finance and Economics,Zhengzhou 450044,China
3.Wuhan University,Wuhan 430072,China
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Abstract  

In this paper it is reported firstly that fermented cellulose was anionized by one pot method with sodium 3-chloro-2-hydroxypropane sulfonate in aqueous phase, and sodium hydroxide solution was used as reactant, solvent, and catalyst. The reaction conditions were mild, the degree of substitution was moderate, and the conversion rate was acceptable. The characterization of cellulose derivative was studied by means of elemental analysis, nuclear magnetic resonance,FTIR and so on. The antifungal biological evaluation of cellulose derivative was carried out, and the results showed that it had certain antifungal properties. The ecological compatibility of cellulose derivatives confirms that they can be applied in archaeology, agriculture and epidemic prevention, etc.



Key wordsfermented cellulose      anionic derivative      antifungal property      one pot method     
Received: 25 November 2022      Published: 19 May 2023
CLC:  O 65  
Cite this article:

Yanli CUI, Shunyao LI, Tianyu ZHANG, Minyan ZHANG, Xiangxiang BAO, Yangyi MAO. Conversion of anionic derivatives of fermented cellulose and evaluation of their antifungal effect. Journal of Zhejiang University (Science Edition), 2023, 50(3): 346-350.

URL:

https://www.zjujournals.com/sci/EN/Y2023/V50/I3/346


发酵纤维素阴离子衍生物的转化与抗菌应用评价

在水相条件下用阴离子醚化剂(3-氯-2-羟基丙磺酸钠)通过一锅法对经微生物改造的纤维素阴离子化,其中的氢氧化钠溶液既作为反应物、溶剂,又作为催化剂,反应条件温和、取代度适中、转化率较高。采用元素分析、核磁共振、傅里叶红外光谱等表征方法研究了纤维素衍生物的取代度和结构,结果表明,获得的纤维素产物已阴离子化。对纤维素衍生物进行了抑制真菌评估,证明其具其有一定的抑菌特性。纤维素衍生物的生态亲和性决定其可应用于文物保护、农业和防疫等领域。


关键词: 发酵纤维素,  阴离子衍生物,  抗菌作用,  一锅法 
Fig.1 Cellulose structure and its hydrogen bond distribution
Fig.2 Etherification of fermented cellulose with CHPASA
序号

CHPASA/

纤维素

NaOH/

CHPASA

温度/

取代度(DS)
171250.12
271550.23
371650.65
471750.43
Table 1 Effect of temperature on degree of substitution of anionic cellulose
序号

CHPASA/

纤维素

NaOH/

CHPASA

温度/

取代度(DS)
141650.02
251650.13
371650.65
491650.53
Table 2 Effect of CHPASA/cellulose molar ratio on degree of substitution of anion cellulose
序号

CHPASA/

纤维素

NaOH/

CHPASA

温度/

取代度(DS)
170.9650.46
271.0650.65
371.1650.51
471.2650.49
Table 3 Effect of NaOH/CHPASA molar ratio on degree of substitution of anion cellulose
Fig.3 2D 1H-13C NMR spectrum of cellulose derivative Y1
Fig.4 Comparison of infrared spectra between cellulose derivative Y1 and fermented cellulose
真菌嗜松青霉出芽短梗霉黑曲霉
抑菌圈直径/mm11.6011.9212.44
11.1812.8013.24
抑菌圈直径平均值/mm11.3912.3612.84
Table 4 Antifungal effect of cellulose derivative Y1
[1]   BETHKE K, PALANTÖKEN S, ANDREI V, et al. Functionalized cellulose for water purification, antimicrobial applications, and sensors[J]. Advanced Functional Materials, 2018, 28: 1800409. DOI:10. 1002/adfm.201800409
doi: 10. 1002/adfm.201800409
[2]   KAMEL S, ALI N, JAHANGIR K, et al. Pharmaceutical significance of cellulose: A review[J]. Express Polymer Letters, 2008, 2(11): 758-778. DOI:10.3144/expresspolymlett.2008.90
doi: 10.3144/expresspolymlett.2008.90
[3]   PERFECT J R.The antifungal pipeline: A reality check[J].Nature Reviews Drug Discovery, 2017,16(9): 603-616. DOI:10.1038/nrd.2017.46
doi: 10.1038/nrd.2017.46
[4]   RASHKI S, SHAKOUR N, YOUSEFI Z, et al. Cellulose-based nanofibril composite materials as a new approach to fight bacterial infections[J]. Frontiers in Bioengineering and Biotechnology, 2021, 9: 732461. DOI:10.3389/fbioe.2021.732461
doi: 10.3389/fbioe.2021.732461
[5]   DO M H, VAN THIKHUAB K, HUYNH P T, et al. Synthesis, characterization, and antibacterial activity of amino-functionalized microcrystalline cellulose derivatives from cotton fibers[J]. Biomass Conversion and Biorefinery, 2022(online). DOI:10. 1007/s13399-022-02391-7
doi: 10. 1007/s13399-022-02391-7
[6]   叶君, 赵星飞, 熊犍. 离子液体在纤维素研究中的应用[J]. 化学进展, 2007(4): 478-484. DOI:10.3321/j.issn:1005-281X.2007.04.005
YE J, ZHAO X F, XIONG Q. Application of ionic liquids in cellulose studies[J]. Chemical Advances, 2007(4): 478-484. DOI:10.3321/j.issn:1005-281X. 2007.04.005
doi: 10.3321/j.issn:1005-281X. 2007.04.005
[7]   FENG Y H, LIU G L, SUN H, et al. A novel strategy to intensify the dissolution of cellulose in deep eutectic solvents by partial chemical bonding[J]. BioResources, 2022, 17(3): 4167-4185. DOI:10. 15376/biores.17.3.4167-4185
doi: 10. 15376/biores.17.3.4167-4185
[8]   YANG Q L, QI H S, LUE A, et al. Role of sodium zincate on cellulose dissolution in NaOH/UREA aqueous solution at low temperature[J]. Carbohydrate Polymers, 2010, 83(3): 1185-1191. DOI:10.1016/j.carbpol.2010.09.020
doi: 10.1016/j.carbpol.2010.09.020
[9]   石纯, 杨海艳, 杨静, 等. 基于LiCL/DMSO全溶体系的巨龙竹组分分离及结构表征[J]. 扬州大学学报(自然科学版), 2017, 20(3): 63-68. DOI:10. 19411/j.1007-824X.2017.03.015
SHI C, YANG H Y, YANG J, et al. Separation and structural characterization of giant bamboo components based on the total solution system of LiCL/DMSO[J]. Journal of Yangzhou University (Natural Science Edition), 2017, 20(3): 63-68. DOI:10.19411/j.1007-824X.2017.03.015
doi: 10.19411/j.1007-824X.2017.03.015
[10]   吴文娟, 邹春阳, 黄丽菁, 等. 竹材在LiCl/DMSO溶剂体系中的溶解及再生性能[J]. 林业科学, 2020, 56(9): 201-206. DOI:10.11707/j.1001-7488. 20200922
WU W J, ZOU C Y, HUANG L J, et al. Dissolution and regeneration of bamboo in LiCl/DMSO solvent system[J]. Scientia Silvae Sinicae, 2020, 56(9): 201-206. DOI:10.11707/j.1001-7488.20200922
doi: 10.11707/j.1001-7488.20200922
[11]   KONO H, NUMATA J. Substituent distribution of propyl cellulose studied by nuclear magnetic resonance[J]. Carbohydrate Research, 2020, 495: 108067. DOI:10.1016/j.carres.108067
doi: 10.1016/j.carres.108067
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