Wang Zhaoyu, Bi Yanhong, Yang Rongling, Zhao Xiangjie, Jiang Ling, Zhu Chun, Zhao Yuping, Jia Jianbo
School of Life Science and Food Engineering, Huaiyin Institute of Technology, Huai'an 223003, China.
College of Food Science and Light Industry, Nanjing Tech University, Nanjing 211816, China.
Biomed Res Int. 2016;2016:4357052. doi: 10.1155/2016/4357052. Epub 2016 Sep 7.
Efficient and highly regioselective synthesis of the potential 6''--sorboyl-polydatin prodrug in biomass-derived 2-methyltetrahydrofuran (2-MeTHF) was achieved using lipase B for the first time. Under the optimal conditions, the initial reaction rate, maximum substrate conversion, and 6''-regioselectivity were as high as 8.65 mM/h, 100%, and 100%, respectively. Kinetic and operational stability investigations evidently demonstrated excellent enzyme compatibility of the 2-MeTHF compared to the traditional organic solvents. With respect to the antioxidant properties, three unsaturated ester derivatives showed slightly lower DPPH radical scavenging activities than the parent agent. Interestingly, further studies also revealed that the antiradical capacities of the acylates decreased with the elongation of the unsaturated aliphatic chain length from C4 to C11. The reason might be attributed to the increased steric hindrance derived from the acyl residues in derivatives.
首次使用脂肪酶B在生物质衍生的2-甲基四氢呋喃（2-MeTHF）中高效且高度区域选择性地合成了潜在的6''-山梨酰基-虎杖苷前药。在最佳条件下，初始反应速率、最大底物转化率和6''-区域选择性分别高达8.65 mM/h、100%和100%。动力学和操作稳定性研究明显表明，与传统有机溶剂相比，2-MeTHF具有出色的酶兼容性。关于抗氧化性能，三种不饱和酯衍生物的DPPH自由基清除活性略低于母体药物。有趣的是，进一步研究还表明，随着不饱和脂肪链长度从C4延长至C11，酰化物的抗自由基能力降低。原因可能归因于衍生物中酰基残基产生的空间位阻增加。
