拟红紫珠中1个新的木脂素葡萄糖苷化合物  

One new lignan glucoside from Callicarpa pseudorubella

作　　者：赵兴 刘翰飞 王欢[1,3] 林开琴 李金玉 潘卫东 娄华勇[1,2] 孙超 ZHAO Xing;LIU Han-fei;WANG Huan;LIN Kai-qin;LI Jin-yu;PAN Wei-dong;LOU Hua-yong;SUN Chao(State Key Laboratory of Functions and Applications of Medicinal Plants,Guizhou Medical University,Guiyang 550014,China;Natural Products Research Center of Guizhou Province,Guiyang 550014,China;School of Pharmaceutical Sciences,Guizhou Medical University,Guiyang 550025,China)

机构地区：[1]贵州医科大学,省部共建药用植物功效与利用国家重点实验室,贵州贵阳550014 [2]贵州省天然产物研究中心,贵州贵阳550014 [3]贵州医科大学药学院,贵州贵阳550025

出　　处：《中草药》2023年第21期6953-6960,共8页Chinese Traditional and Herbal Drugs

基　　金：国家自然科学基金资助项目(32060100);国家自然科学基金资助项目(32100322);贵州省科技计划项目(黔科合基础-ZK[2021]534,QKHZC[2021]411,QKHZC[2022]019);贵州省科技计划项目(黔科中引地[2022]4015)。

摘　　要：目的研究拟红紫珠Callicarpa pseudorubella的化学成分及其生物活性。方法利用多种色谱手段(硅胶、Sephadex LH-20、RP-18反相硅胶柱色谱和半制备型HPLC等)进行分离纯化,运用理化性质结合现代波谱学(紫外、红外、核磁、质谱等)技术进行结构鉴定。采用RSL3诱导的HT22小鼠海马神经元细胞模型铁死亡抑制活性进行筛选。结果从拟红紫珠中分离得到11个化合物,分别鉴定为(7S,7’R,8R,8’S,9S)-芝麻素-9-O-β-D-葡萄糖苷(1)、(+)-松脂素-4-O-β-D-葡萄糖苷(2)、(7R,7′R,7’’S,7’’’S,8S,8′S,8’’S,8’’’S)-4’’,4’’’-二羟基-3,3′,3’’,3’’’,5,5′-六甲氧基-7,9′;7′,9-二环氧-4,8’’;4′,8’’’-双氧-8,8′-双新木脂素-7’’,7’’’,9’’,9’’’-四醇(3)、(7R,7′R,7’’R,7’’’S,8S,8′S,8’’S,8’’’S)-4’’,4’’’-二羟基-3,3′,3’’,3’’’,5,5′-六甲氧基-7,9′;7′,9-二环氧-4,8’’;4′,8’’’-双氧-8,8′-双新木脂素-7’’,7’’’,9’’,9’’’-四醇(4)、泡桐素(5)、4-氧代芝麻素(6)、芝麻素(7)、β-谷甾醇(8)、熊果酸(9)、3β-羟基豆甾-5烯-7-酮(10)和3β-羟基豆甾-5,22-二烯-7-酮(11)。生物活性结果显示,化合物7、10和11对RSL3诱导的HT22细胞铁死亡较模型组有明显的抑制活性,其细胞存活率分别为30.37%、31.93%和36.57%(模型组为23.4%)。结论化合物1为新化合物,命名为拟红紫珠苷A。所有化合物均为首次从拟红紫珠中分离得到,且3个化合物显示出潜在的铁死亡抑制活性。objective To study the chemical constituents of Callicarpa pseudorubella and their biological activities.MethodssThe chemical constituents were isolated and purified by silica gel,Sephadex LH-20,RP-18 reversed phase silica gel column chromatography and semi-preparative high performance liquid chromatography(HPLC).Then their structures were elucidated by modern spectroscopic analyses(UV,IR,NMR,and HRESIMS)and physicochemical properties.All isolates were evaluated for their inhibitory effect on RSL3-induced ferroptosis in HT22 mouse hippocampal neuronal cells.Results A total of eleven compounds were isolated from C.pseudorubella and identified as(7S,7'R,8R,8'S,9S)-sesamin-9-O-β-D-glucopyranoside(1),(+)-pinoresinol-4-O-β-D-glucopyranoside(2),(7R,7'R,7''S,7'''S,8S,8'S,8''S,8'''S)-4'',4'''-dihydroxy-3,3',3''3''',5,5'-hexamethoxy-7,9',7',9-diepoxy-4,8",4',8"-bisoxy-8,8-dineolignan-7",7",9",9"-tetraol(3),(7R,7'R,7''R,7'''S,8S,8'S,8''S,8'''S)-4'',4'''-dihydroxy-3,3',3'',3''',5,5'-hexamethoxy-7',9',7',9-diepoxy-4,8'',4',8'''-bisoxy-8,8'-dineolignan-7'',7''',9'',9'''-tetraol(4),paulownin(5),4-oxosesamin(6),sesamin(7),β-sitosterol(8),ursolic acid(9),3β-hydroxystigmast-5-en-7-one(10),and 3β-hydroxystigmast-5,22-dien-7-one(11).Compared with the model group,compounds 7,10 and 11 exhibited obvious inhibitory activity on RSL3-induced HT22 cells ferroptosis,with the survival rate of 30.37%,31.93% and 36.57%,respectively(23.4% in model group).Conclusion Compound 1 is a new compound,named as callicoside A.And all compounds are isolated from C.pseudorubella for the first time.Moreover,compounds 7,10 and 11 exhibit obvious inhibitory activity against RSL3-induced HT22 cells ferroptosis.

关 键 词：拟红紫珠 木脂素糖苷 拟红紫珠苷A 芝麻素 熊果酸 3β-羟基豆甾-5烯-7-酮 铁死亡抑制 

分 类 号：R284.1[医药卫生—中药学]