Synthesis, Characterization and Antimicrobial Activity of Konjac Glucomannan Derivative with Quaternary Ammonium Salts
LEI Wan-xue1,2,XU Xia3,LIN Fang1,YANG Qin-huan1,LI Zhen-jun1,ZHANG Ting-you1*
1. The Key Laboratory of Leather Chemistry and Engineering of Ministry of Education, Sichuan University, Chengdu 610065,China 2. Department of Chemistry, Henan Institute of Education, Zhengzhou 450001, China 3. College of Pharmacy, Zhengzhou University, Zhengzhou 450052, China
Abstract：Methacryloxylethyl tetradecyl dimethyl ammonium bromide was grafted onto konjac glucomannan using ceric ammonium nitrate as an initiator, and the konjac glucomannan derivative with quaternary ammonium salts was obtained. The konjac glucomannan derivative was investigated by hydrogen nuclear magnetic resonance spectroscopy (1H NMR), Fourier transform infrared spectroscopy (FTIR), differential scanning calorimeter (DSC), and Zeta sizer nano series. The antimicrobial properties of the konjac glucomannan derivative against selected microorganisms were tested by the quantitative suspension method. The results revealed that (1) methacryloxylethyl tetradecyl dimethyl ammonium bromide can be grafted onto the surface of the konjac glucomannan, and the percentage grafting increases with increasing the amount of methacryloxylethyl tetradecyl dimethyl ammonium bromide. (2) The Zeta potential showed that the isoelectric point of the konjac glucomannan and the modified konjac glucomannan is pH 4.5 and pH 9.9, respectively. The shift of the isoelectric point is due to the quaternary ammonium groups. (3) The obtained konjac glucomannan derivative has significant inhibition effect on the growth of microorganisms, and the bactericidal rates in 15 min for E.coil (8099), S. aureus (ATCC 6538) and C. albicans (ATCC10231) were 99.99％, 99.99％ and 98.13％, respectively.
[1] Kaname K, Kohsaku O, Kenichi H, et al. Carbohydrate Polymer, 2003, 53: 183. [2] Kato K, Matsuda K. Agricultural and Biological Chemistry, 1969, 33: 1446. [3] Maeda M, Shimahara M, Sugiyama N. Agric. Biol. Chem., 1980, 44: 245. [4] Cescutti P, Campa C, Delben F, et al. Carbohydrate Research, 2002, 337(24): 2505. [5] YANG Guang, XIONG Xiao-peng, ZHANG Li-na. Journal of Membrane Science, 2002, 201: 161. [6] PANG Jie, LIN Qiong, ZHANG Pu-sheng, et al（庞 杰, 林 琼, 张普生, 等）. Chinese Journal Structure Chemistry(结构化学), 2003，22(6): 633. [7] WANG Kang, HE Zhi-min. International Journal of Pharmaceutics, 2002, 244: 117. [8] CHEN Hsiao-Ling, Ph D. R. D. Nautrition, 2006, 22: 112. [9] Pathak C P, Barman S P, Philbrook M C, et al. US Patent, 6 639 014, 2003. [10] CHEN Li-gui, LIU Zhi-lan, ZHUO Ren-xi. Polymer, 2005, 46: 6274. [11] ZHANG Ying-qing, XIE Bi-jun, GAN Xin. Carbohydrate Polymer, 2005, 60: 27. [12] Nussinovitch A. US Patent, 6 680 184, 2004. [13] YU Hui-qun, HUANG Yi-hong, YING Hou, et al. Carbohydrate Polymers, 2007, 69: 29. [14] TANG R P, DU Y M, ZHENG H, et al. Journal of Applied Polymer Science, 2003, 88(5): 1095. [15] GAO S J, ZHANG L N, CAO J L. Journal of Applied Polymer Science, 2003, 90(8): 2224. [16] YANG G, HUANG Q L, ZHANG L N, et al. Journal of Applied Polymer Science, 2004, 92(1): 77. [17] YU Hui-qun, HUANG Yi-hong, YING Hou, et al. Carbohydrate Polymers, 2007, 69: 29. [18] XU Xia, YANG Qin-huan, LEI Wan-xue, et al（徐 霞, 杨秦欢, 雷万学, 等）. Spectroscopy and Spectral Analysis（光谱学与光谱分析），2006, 26(3): 444. [19] MA Guo-xin, WANG Cheng-long, FAN Duo-wang, et al(马国欣, 王成龙, 范多旺, 等). Spectroscopy and Spectral Analysis（光谱学与光谱分析），2006, 26(3): 434. [20] LU Dian-nan, ZHOU Xuan-rong, XING Xiao-dong, et al（卢滇楠, 周轩榕, 邢晓东, 等）. Acta Polymeric Sinica（高分子学报）, 2004, (1): 107.
