摘要
延龄草苷为薯蓣皂苷元-3-O-β-D-吡喃葡萄糖苷,来源于中药延龄草,为甾体皂苷类化合物,具有广泛的生物活性。通过两种方法合成延龄草苷:Koenigs-Knorr法,以溴代糖为糖基供体,以碳酸银作为催化剂,将薯蓣皂苷元与溴代-α-D-四乙酰葡萄糖成苷合成延龄草苷;三氟化硼-乙醚催化法,全乙酰葡萄糖作为糖供体,将薯蓣皂苷元与α-D-五乙酰葡萄糖成苷合成延龄草苷。合成产物和中间体的结构经^(1)H-NMR和^(13)C-NMR法确认。比较两种合成方法:Koenigs-Knorr法路线较长,步骤略为繁琐,收率较高,为74.7%;三氟化硼-乙醚催化法路线较短,反应迅速,成本更低,但收率较低,为34.9%。采用的两种方法均具有操作简单、反应条件温和的优点,可为延龄草苷的广泛应用提供物质保证,并为甾体皂苷类化合物的化学合成提供技术支持。
Trillin(diosgenin-3-O-β-d-glucopyranoside)is a kind of steroidal saponin,which is derived from the traditional Chinese medicine Trillium tschonoskii Maxim.In this paper,trillin was synthesized by two methods.In Koenigs-Knorr method,bromosaccharide was used as sugar donor and silver carbonate was used as catalyst,trillin was synthesized from diosgenin and bromo-α-D-tetraacetyl glucose into glycosides.In boron trifluoride ether catalysis method,total acetyl glucose was used as sugar donor,trillin was synthesized from diosgenin andα-D-pentaacetyl glucose into glycosides.The structures of the products and intermediates were confirmed by^(1)H-NMR and^(13)C-NMR.The two synthetic methods were compared:Koenigs-Knorr method had a longer route and a slightly more complicated step,with a higher yield of 74.7%;and the catalytic method of boron trifluoride ether had a shorter route and a faster reaction,the cost was lower,but the yield was lower(34.9%).Both methods had the advantages of simple operation and mild reaction conditions,which could provide material guarantee for the wide application of trillin glycosides and provide technical support for the chemical synthesis of steroidal saponins.
作者
钟婷
何贝桥
苏进
杨淑珍
张园园
ZHONG Ting;HE Bei-qiao;SU Jin;YANG Shu-zhen;ZHANG Yuan-yuan(School of Chinese Materia Medica,Beijing University of Chinese Medicine,Beijing 102488,China)
出处
《当代化工》
CAS
2021年第3期594-597,共4页
Contemporary Chemical Industry
基金
2018年度北京中医药大学基本科研业务费(在读研究生项目)资助项目(项目编号:2018-JYBZZ-XS068)。
