基于点击反应的单宁衍生物的合成及其性能

doi:10.16085/j.issn.1000-6613.2019-0523

化工进展 ›› 2019, Vol. 38 ›› Issue (12): 5519-5524.DOI: 10.16085/j.issn.1000-6613.2019-0523

基于点击反应的单宁衍生物的合成及其性能

袁花(),钟鑫,廖若雪,阳思,邹金岑,彭志远()

吉首大学化学化工学院，湖南吉首 416000

收稿日期:2019-04-04 出版日期:2019-12-05 发布日期:2019-12-05
通讯作者: 彭志远
作者简介:袁花（1995—），女，硕士研究生，研究方向为环境催化与吸附材料。E-mail：787147050@qq.com。
基金资助:
国家自然科学基金(31760196);吉首大学研究生创新项目(JGY201849);吉首大学锰锌钒产业技术合作创新中心项目;吉首大学校级科研项目(Jdy19016)

Synthesis and properties of tannin derivatives based on click reaction

Hua YUAN(),Xin ZHONG,Ruoxue LIAO,Si YANG,Jincen ZOU,Zhiyuan PENG()

School of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, Hunan, China

Received:2019-04-04 Online:2019-12-05 Published:2019-12-05
Contact: Zhiyuan PENG

摘要/Abstract

摘要：

植物单宁与溴丙炔反应制备的炔化单宁与对十二烷基苯磺酰叠氮通过点击反应合成单宁衍生物。采用红外光谱仪和元素分析仪对单宁衍生物的结构进行表征，并研究其表面张力、抗氧化能力以及对细菌的抑制作用等性能。结果表明，在单宁分子的结构中引入长链烷基后，改善其亲脂性，制备出的单宁衍生物能显著降低水溶液的表面张力，当单宁衍生物质量浓度为0.8mg/mL时，可降低水溶液的表面张力至28.94mN/m；单宁衍生物对1,1-二苯基-2-苦基苯肼基自由基具有较强的清除能力，当单宁衍生物质量浓度为0.25mg/mL时，对1,1-二苯基-2-苦基苯肼基自由基的最大清除率可达97.08%；由于单宁脂溶性的增加及具有抗菌性能的三氮唑基团的引入，单宁衍生物对大肠杆菌和金黄色葡萄球菌的抑制作用明显增强。

关键词: 单宁, 点击反应, 单宁衍生物, 对十二烷基苯磺酰叠氮

Abstract:

Tannin derivatives were prepared by the click reaction of p-dodecylbenzene sulfonyl azide and alkynylated tannin synthesized by the substitute reaction of tannins with bromopropyne. The tannin derivatives structure was characterized by FTIR and elemental analyzer, and the surface tension, antioxidant ability and inhibitory functions on bacteria of tannin derivatives were studied. The experimental results showed that the tannin derivatives can significantly reduce the surface tension of water due to the introduction of the long-chain alkyl groups and the improvement of tannin lipophilicity. The lowest surface tension of the tannin derivatives can be up to 28.94mN/m at 0.8mg/mL， the tannin derivatives had strong scavenging ability to the 1,1-diphenyl-2-picrylphenylhydrazinyl radical which the maximum scavenging rate of 97.08% at 0.25mg/mL， the tannin derivatives exhibited stronger antibacterial activity against Escherichiacoli and Staphylococcusaureus because of the improvement of tannin liposolubility and the introduction of antibacterial triazol groups.

Key words: tannins, click reaction, tannin derivatives, p-dodecylbenzene sulfonyl azide

中图分类号:

O636

袁花,钟鑫,廖若雪,阳思,邹金岑,彭志远. 基于点击反应的单宁衍生物的合成及其性能[J]. 化工进展, 2019, 38(12): 5519-5524.

Hua YUAN,Xin ZHONG,Ruoxue LIAO,Si YANG,Jincen ZOU,Zhiyuan PENG. Synthesis and properties of tannin derivatives based on click reaction[J]. Chemical Industry and Engineering Progress, 2019, 38(12): 5519-5524.

图/表 8

图1 单宁衍生物的合成路线

表1 ·DPPH清除实验中样品加量表

组别	样品液/mL	·DPPH溶液/mL	乙醇/mL
空白组	0	4	2
样品组	2	4	0
对照组	2	0	4

图2 单宁、炔化单宁和单宁衍生物的红外光谱图

图3 单宁衍生物与单宁的表面张力

图4 单宁衍生物胶束的胶束示意图和胶束的光学显微镜照片

图5 单宁衍生物、单宁和BHT对·DPPH的清除能力

图6 单宁和单宁衍生物对大肠杆菌的抑菌性能

图7 单宁和单宁衍生物对金黄色葡萄球菌的抑菌性能

参考文献 20

1	孙达旺. 植物单宁化学[M]. 北京: 中国林业出版社, 1992: 411-429.
	SUN Dawang. Chemistry of vegetable tannins[M]. Beijing: China Forestry Press, 1992: 411-429.
2	TENG B, JIAN X, WANG Y, et al. Characterization of acacia mangium tannin fractions extracted with different organic solvents[J]. Asian Joumal of Chemistry, 2015, 27(5): 1847-1850.
3	冯健, 余杰, 周建, 等. 牛血清白蛋白纳米球接枝杨梅单宁的制备以及吸附去除水体中Pb²⁺的性能[J]. 化工进展, 2019, 38(2): 1075-1084.
	FENG Jian, YU Jie, ZHOU Jian, et al. Removal of Pb²⁺ from aqueous solution using bovine serum albumin nanospheres grafted with bayberry tannin[J]. Chemical Industry and Engineering Progress, 2019, 38(2): 1075-1084.
4	SHIRMOHAMMADLI Y, EFHAMISISI D, PIZZI A. Tannins as a sustainable raw material for green chemistry: a review[J]. Industrial Crops and Products, 2018, 126: 316-332.
5	段文贵, 耿哲, 张加研, 等. 改性松香-缩合单宁酯的制备及性质[J]. 林产化学与工业, 2009, 29(3): 6-12.
	DUAN Wengui, GENG Zhe, ZHANG Jiayan, et al. Preparation and properties of modified rosin-condensed tannins esters[J]. Chemistry and Industry of Forest Products, 2009, 29(3): 6-12.
6	李艳, 安丽萍, 郭禹辰, 等. 酚羟基保护法合成硬脂酰单宁酸酯及其抗氧化性能评价[J]. 林产化学与工业, 2016, 36(6): 49-55.
	LI Yan, AN Liping, GUO Yuchen, et al. Synthesis and antioxidant acticity of stearoyl tannic acid ester based on hydroxyl protection[J]. Chemistry and Industry of Forest Products, 2016, 36(6): 49-55.
7	SAYED G H, GHUIBA F M, ABDOU M I. Synthesis, surface and thermodynamic parameters of some biodegradable nonionic surfactants derived from tannic acid[J]. Colloid and Surfaces A: Physicochemical and Engineering Aspects, 2012, 393(1): 966-104.
8	NEGM N A, MOHAMMED D E, MOHAMADL H N. Environmentally friendly nonionic surfactants derived from tannic acid: synthesis, characterization and surface activity[J]. Journal of Surfactants and Detergents, 2012, 15(4): 433-443.
9	LI J, CHEN D H, ZHANG D Q, et al. Preparation of triazole compounds via click chemistry reaction and formation of the protective self-assembled membrane against copper corrosion[J]. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2018, 550: 145-154.
10	邹滔, 王若男, 彭开美, 等. 一种基于点击化学的高性能亲水抗菌聚氨酯合成与表征[J]. 化工进展, 2018, 37(7): 2704-2711.
	ZOU Tao, WANG Ruonan, PENG Kaimei, et al. Synthesis and characterization of a high-performance antibacterial waterbome ployurethane via click chemistry[J]. Chemical Industry and Engineering Progress, 2018, 37(7): 2704-2711.
11	熊福全, 韩雁明, 李改云, 等. 点击化学在木质纤维素化学修饰中的研究现状[J]. 林业科学, 2016, 52(3): 90-96.
	XIONG Fuquan, HAN Yanming, LI Gaiyun, et al. Research status of click chemistry in lignocellulosic chemical modification[J]. Forestry Science, 2016, 52(3): 90-96.
12	CHUNG H Y, Al-KHOUJA A, WASHBUM N R. Lignin-based graft copolymers via ATRP and click chemistry[J]. ACS Symposium, 2013, 1144: 373-391.
13	BRUSA C, OCHS M, REMOND C, et al. Chemoenzymatic synthesis of “Click” xylosides and xylobiosides from lignocellulosic biomass[J]. RSC Advances, 2014, 4(18): 9330-9338.
14	OLDHAM E D, SEELAM S, LEMA C, et al. Synthesis, surface, properties and biocompatibility of 1,2,3-triazole-containing alkyl β-D-xylopyranoside surfactants[J]. Carbohydrate Research, 2013, 379: 68-77.
15	ZHOU Z, HUANG Y, LIANG J, et al. Extraction, purification and antiradiation activity of persimmon tannin from diospyros kaki L.f.[J]. Journal of Environmental Radioactivity, 2016, 162: 182-188.
16	WANG R R, DING S H, ZHAO D D, et al. Effect of dehydration methods on antioxidant activities, phenolic contents, cyclic nucleotides and volatiles of jujube fruits[J]. Food Science Biotechnol, 2015, 24(6): 1-7.
17	马志红, 姚开, 石碧. 具有表面活性的酯化单宁酸的合成及其性质研究[J]. 林产化学与工业, 2003(1): 21-24.
	MA Zhihong, YAO Kai, SHI Bi. Synthesis of esterified tannic acidspossessing surface activities and studies on properties of the products[J]. Chemistry and Industry of Forest Products, 2003 (1): 21-24.
18	李翠勤, 郭苏月, 王鹏祥, 等. 树状聚酰胺-胺桥联受阻酚类抗氧化剂的合成及清除·DPPH活性研究[J]. 高分子通报, 2016(10): 68-77.
	LI Cuiqin, GUO Suyue, WANG Pengxiang, et al. Synthesis and activities of scavenging ·DPPH of dendritic pamam bridged hindered phenol antioxidants[J]. Polymer Bulletin, 2016(10): 68-77.
19	XIA Jiding, XIA Yongmei, NNANNA Ifendu A. Structure-function relationship of acyl amino acid surfactants: surface activity and antimicrobial properties[J]. Journal of Agricultural and Food Chemistry, 1995, 43(4): 867-871.
20	TAN W, LI Q, DONG F, et al. Novel 1,2,3-triazolium-functionalized starch derivatives: synthesis, characterization, and evaluation of antifungal property[J]. Carbohydrate polymers, 2017, 160: 163-171.

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基于点击反应的单宁衍生物的合成及其性能

Synthesis and properties of tannin derivatives based on click reaction

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