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-D-glucopyranoside（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pH 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 modify the structure of psoralidin using in vitro enzymatic glycosylation to improve its water solubility and stability. Methods A new psoralidin glucoside (1) was obtained by enzymatic glycosylation using a UDP-glycosyltransferase. The chemical structure of compound 1 was elucidated by HR-ESI-MS and nuclear magnetic resonance (NMR) analysis. The high- performance liquid chromatography (HPLC) peaks were integrated and sample solution concentrations were calculated. MTT assay was used to detect the cytotoxicity of the compounds against 3 cancer cell lines in vitro. Results Based on the spectroscopic data, the new psoralidin glucoside was identified as psoralidin-6',7-di-O-β-D-glucopyranoside (1), whose water solubility was 32.6-fold higher than that of the substrate. Analyses of pH and temperature stability demonstrated that compound 1 was more stable than psoralidin at pH 8.8 and at high temperatures. Only psoralidin exhibited a moderate cytotoxicity against 3 human cancer cell lines. Conclusion In vitro enzymatic glycosylation is a powerful approach for structural modification and improving water solubility and stability of compounds.
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