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目的为提高补骨脂定的水溶性和稳定性,用体外酶法糖基化反应对其进行结构修饰。方法通过UDP-糖基转移酶对补骨脂定进行糖基化修饰,合成一种新的葡萄糖苷化合物(1)。使用高分辨电喷雾电离质谱(HR-ESI-MS)和核磁共振(NMR)分析,鉴定化合物1的结构;利用高效液相色谱峰面积计算出样品溶液的浓度;MTT法检测化合物对3种肿瘤细胞(SMMC7721、MCF-7、SW480)增殖的影响。结果根据波谱分析,鉴定制备出的新型葡萄糖苷化合物为psoralidin-6’,7-di-O-β-Dglucopyranoside(1)。水溶性检测结果表明,化合物1的水溶性是底物(补骨脂定)水溶性的32.6倍。此外,化合物1在p H 8.8和高温条件下较补骨脂定更加稳定。在抗肿瘤细胞增殖实验中,只有补骨脂定对3种肿瘤细胞都显示出较强的抑制能力。结论体外酶法糖基化是进行结构修饰、改善水溶性和稳定性的强有力方法。
Objective To improve the water solubility and stability of psoralen, structural modification was carried out by in vitro enzymatic glycosylation. Methods Glycosylation of psoralen with UDP-glycosyltransferase was performed to synthesize a novel glucoside compound (1). The structure of compound 1 was identified using HR-ESI-MS and NMR analysis; the concentration of sample solution was calculated using peak area of high performance liquid chromatography; and the activity of the compound against 3 tumors Cells (SMMC7721, MCF-7, SW480). Results According to the spectral analysis, the novel glucoside compounds were identified as psoralidin-6 ’, 7-di-O-β-Dglucopyranoside (1). Water-soluble test results show that the water-solubility of compound 1 is 32.6 times that of the substrate (psoralen). In addition, Compound 1 is more stable than psoralen at pH 8.8 and high temperature. In antitumor cell proliferation experiments, only psoralen showed a strong inhibitory effect on all three kinds of tumor cells. Conclusion Enzymatic glycosylation in vitro is a powerful method for structural modification and improvement of water solubility and stability.