巴山重楼的甾体皂苷类化学成分的分离和鉴定  

Isolation and identification of steroidal saponins from Paris bashanensis

作　　者：田韵远 樊培 陆云阳 刘杨 陈文文 胡晋铭 曹宇 袁晓峰 李天怡 汤海峰 TIAN Yunyuan;FAN Pei;LU Yunyang;LIU Yang;CHEN Wenwen;HU Jinming;CAO Yu;YUAN Xiaofeng;LI Tianyi;TANG Haifeng(Department of Chinese Materia Medica and Natural Medicines,School of Pharmacy,Air Force Medical University,Xi'an 710032,China)

机构地区：[1]空军军医大学药学系,西安710032

出　　处：《环球中医药》2022年第11期1991-2000,共10页Global Traditional Chinese Medicine

基　　金：国家自然科学基金面上项目(81973192);陕西省重点研发计划(2020SF-311,2021ZDLSF04-07);陕西省中医药管理局“秦药”开发重点科学研究项目(2021-02-ZZ-003)。

摘　　要：目的 提取分离巴山重楼根茎中的甾体皂苷类成分,并对其进行结构鉴定。方法 用水饱和正丁醇对70%的乙醇提取物部分进行萃取得到重楼总皂苷,总皂苷通过硅胶柱色谱、反相ODS柱色谱、Sephadex LH-20凝胶柱色谱和半制备HPLC等多种色谱分离技术进行分离得到单体化合物,最后通过NMR、MS等波谱技术和酸水解等化学方法鉴定化合物结构。结果 分离得到10个甾体皂苷类化合物,分别鉴定为:重楼皂苷Ⅵ(1)、薯蓣皂苷元-3-O-α-L-吡喃鼠李糖基-(1→4)-α-L-吡喃鼠李糖基-(1→4)-β-D-吡喃葡萄糖苷(2)、3β,5α,6β-三羟基-(25R)-螺甾-3-O-α-L-吡喃鼠李糖基-(1→2)-β-D-吡喃葡萄糖苷(3)、3β,7β,12β-三羟基-(25R)-螺甾-5-烯-3-O-α-L-吡喃鼠李糖基-(1→4)-[α-L-吡喃鼠李糖基-(1→2)]-β-D-吡喃葡萄糖苷(4)、icogenin 1(5)、26-O-β-D-吡喃葡萄糖基-22-甲氧基-3β,26-二羟基-(25R)-呋甾-5-烯-3-O-β-D-吡喃葡萄糖基-(1→4)-[α-L-吡喃鼠李糖基-(1→3)-α-L-吡喃鼠李糖基-(1→3)]-α-L-吡喃鼠李糖苷(6)、cesdiurinⅡ(7)、zingiberenoside B(8)、26-O-β-D-吡喃葡萄糖基-15α-甲氧基-3β,26-二羟基-(25R)-呋甾-5,20-二烯-3-O-α-L-吡喃鼠李糖基-(1→4)-[α-L-吡喃鼠李糖基-(1→2)]-β-D-吡喃葡萄糖苷(9)和dioscoreside E(10)。结论 10个甾体皂苷包括4个异螺甾烷醇型和6个呋甾烷醇型;除化合物1外,其余化合物均首次从巴山重楼中分离得到。Objective To study the steroidal saponins from the rhizomes of Paris bashanensis and identify their chemical structures. Methods The total saponins from the n-butanol fraction of 70% ethanol extraction were isolated and purified by column chromatographies of silica gel, ODS, Sephadex LH-20 and semi-preparative HPLC to obtain monomeric compounds. The structures were identified by spectroscopic analysis and acid hydrolysis. Results Ten steroidal saponins were isolated and identified as polyphyllin Ⅵ(1), diosgenin-3-O-α-L-rhamnopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranoside(2),3β,5α,6β-trihydroxy-(25R)-spirost-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside(3), 3β,7α,12α-trihydroxy-(25R)-spirost-5-en-3-O-α-L-rhamnopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-O-β-D-glucopyranoside(4), icogenin 1(5), 26-O-β-D-glucopyranosyl-22-methoxy-3β,26-dihydroxy-(25R)-furost-5-en-3-O-β-D-glucopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→3)]-α-L-rhamnopyranoside(6), cesdiurin Ⅱ(7), zingiberenoside B(8), 26-O-β-D-glucopyranosyl-15α-methoxy-3β,26-dihydroxy-(25R)-furost-5,20-dien-3-O-α-L-rhamnopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside(9) and dioscoreside E(10), respectively. Conclusion The ten steroidal saponins, including four isospirostanol-type and six furostanol-type saponins, were isolated from P. bashanensis for the first time except polyphyllin Ⅵ.

关 键 词：重楼属 巴山重楼 化学成分 甾体皂苷 化学结构 结构鉴定 

分 类 号：R284.1[医药卫生—中药学]