具有各种β(1→2)连接二糖的甘草次酸糖苷的制备及其对四氯化碳诱导的肝损伤的细胞保护作用。

Preparation of glycyrrhetic acid glycosides having various beta(1----2)-linked disaccharides and their cytoprotective effects on carbon tetrachloride-induced hepatic injury.

作者信息

Saito S, Kuroda K, Hayashi Y, Sasaki Y, Nagamura Y, Nishida K, Ishiguro I

机构信息

Faculty of Pharmaceutical Sciences, Josai University, Saitama, Japan.

出版信息

Chem Pharm Bull (Tokyo). 1991 Sep;39(9):2333-9. doi: 10.1248/cpb.39.2333.

DOI:10.1248/cpb.39.2333

PMID:1804547

Abstract

Glycyrrhetic acid glycosides (1-7) having beta(1----2)-linked disaccharides such as 2-O-beta-D-glucopyranosyl-beta-D-galactopyranose, 2-O-beta-D-galactopyranosyl-beta-D-galactopyranose, 2-O-beta-D-glucuronopyranosyl-beta-D-galactopyranose, 2-O-beta-D-glucopyranosyl-beta-D-glucuronopyranose, 2-O-beta-D-galactopyranosyl-beta-D-glucuronopyranose, 2-O-beta-D-galactopyranosyl-beta-D-glucopyranose, 2-O-beta-D-glucuronopyranosyl-beta-D-glucopyranose, respectively, were synthesized by stepwise construction; from glycyrrhetic acid monoglycosides to the diglycosides. The cytoprotective activities of the glycosides 1-7 and 2-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosyl-11-oxoolean-12-e n-30-oate (8) were compared with natural occurring glycyrrhizin (9). Among these glycosides 1-8, glycosides 3 and 7 having beta-D-glucuronopyranose (glcUA) as the only terminal sugar component were more effective materials against hepatic injury than glycyrrhizin 9.

摘要

分别具有β(1→2)连接的二糖如2 - O - β - D - 吡喃葡萄糖基 - β - D - 吡喃半乳糖、2 - O - β - D - 吡喃半乳糖基 - β - D - 吡喃半乳糖、2 - O - β - D - 吡喃葡萄糖醛酸基 - β - D - 吡喃半乳糖、2 - O - β - D - 吡喃葡萄糖基 - β - D - 吡喃葡萄糖醛酸、2 - O - β - D - 吡喃半乳糖基 - β - D - 吡喃葡萄糖醛酸、2 - O - β - D - 吡喃半乳糖基 - β - D - 吡喃葡萄糖、2 - O - β - D - 吡喃葡萄糖醛酸基 - β - D - 吡喃葡萄糖的甘草次酸糖苷（1 - 7）通过逐步构建法合成；从甘草次酸单糖苷到二糖苷。将糖苷1 - 7和2 - O - (β - D - 吡喃葡萄糖基) - β - D - 吡喃葡萄糖基 - 11 - 氧代齐墩果 - 12 - 烯 - 30 - 酸酯（8）的细胞保护活性与天然存在的甘草酸（9）进行比较。在这些糖苷1 - 8中，以β - D - 吡喃葡萄糖醛酸（glcUA）作为唯一末端糖成分的糖苷3和7是比甘草酸9更有效的抗肝损伤物质。