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目的:建立龙胆苦苷乙酰化结构修饰的技术工艺并考察其乙酰化产物的理化特性。方法:以反应时间、反应温度、乙酸酐与龙胆苦苷的摩尔比为考察因素,通过正交试验优选龙胆苦苷乙酰化结构修饰的技术工艺,并对显著影响因素进行单因素试验考察;通过表观油/水分配系数、稳定性试验及粉体学基本性质等的考察探讨龙胆苦苷乙酰化产物的理化特性。结果:最佳乙酰化工艺为以吡啶为催化剂,乙酸酐为乙酰化剂,乙酸酐-龙胆苦苷(10∶1),20℃反应12 h;乙酰化产物得率94.02%。纯化物经紫外光谱、质谱等鉴定为四乙酰化龙胆苦苷,其在水中的表观油/水分配系数(P)的lg P=1.40,P随p H增大而降低;乙酰化龙胆苦苷对高温和酸敏感、对高湿和强光不敏感、流动性欠佳。结论:龙胆苦苷的乙酰化结构修饰工艺稳定可控。其乙酰化产物体内吸收特性优于龙胆苦苷本身,可有效提高后者的生物利用度。
OBJECTIVE: To establish a technique for the acetylation of gentiopicroside and investigate its physical and chemical properties. Methods: Taking the reaction time, reaction temperature and the molar ratio of acetic anhydride and gentiopicroside as the investigation factors, the technological process of acetylation of gentiopicroside was optimized by orthogonal test, and single factor test was conducted on the significant influencing factors The physico-chemical properties of gentiopicroside acetylation products were investigated by means of apparent oil / water partition coefficient, stability test and basic properties of powder science. Results: The best acetylation process was pyridine as catalyst, acetic anhydride as acetylating agent, acetic anhydride - gentiopicroside (10:1) and reaction at 20 ℃ for 12 h. The yield of acetylated product was 94.02%. The purified compound was identified as tetraacetylated gentiopicroside by ultraviolet spectrum and mass spectrometry. Its apparent water / oil partition coefficient (P) in water was 1g P = 1.40, P decreased with increasing p H; Gall saponins are sensitive to high temperatures and acids, insensitive to high humidity and light, and poor fluidity. Conclusion: The acetylation structure of gentiopicroside is stable and controllable. The acetylated product in vivo absorption characteristics than gentiopicroside itself, which can effectively improve the latter bioavailability.