睡菜醋酸乙酯部位化学成分及其神经保护作用研究  

Chemical constituents of ethyl acetate extract from Menyanthes trifoliate and their neuroprotective activity

作　　者：金冠 何芷芸 张志麒 刘呈雄 陈剑锋 邹坤 程凡 JIN Guan;HE Zhi-yun;ZHANG Zhi-qi;LIU Cheng-xiong;CHEN Jian-feng;ZOU Kun;CHENG Fan(Hubei Key Laboratory of Natural Products Research and Development,College of Biological and Pharmaceutical Sciences,China Three Gorges University,Yichang 443002,China;Shengnongjia National Park Administration,Shengnongjia Forestry District 442400,China)

机构地区：[1]三峡大学生物与制药学院天然产物研究与利用湖北省重点实验室(三峡大学),湖北宜昌443002 [2]神农架国家公园管理局,湖北神农架林区442400

出　　处：《中草药》2022年第4期985-992,共8页Chinese Traditional and Herbal Drugs

基　　金：国家自然科学基金资助项目(81773952);国家自然科学基金资助项目(81803383);湖北省神农架林区自然科学基金(SNJKJ2016029)。

摘　　要：目的研究神农架产睡菜Menyanthes trifoliate全草醋酸乙酯部位的化学成分及其神经保护作用。方法采用薄层色谱,正相硅胶、AB-8大孔树脂、Sephadex LH-20葡聚糖凝胶及制备型HPLC等柱色谱方法分离纯化,利用NMR、MS等波谱学方法鉴定化合物结构。采用体外建立皮质酮诱导PC12细胞损伤模型,就单体化合物对皮质酮诱导PC12细胞损伤的保护作用进行初步确认。结果从睡菜醋酸乙酯部位中得到了21个化合物,分别鉴定为4-O-咖啡酰奎尼酸甲酯(1)、绿原酸甲酯(2)、绿原酸(3)、异秦皮素(4)、异嗪皮啶(5)、7R,7'R,8S,8'S-(+)-新-橄榄脂素-4-O-β-D-吡喃葡萄糖苷(6)、肿柄雪莲苷(7)、丁香脂素(8)、苏式-(7R,8R)-愈创木基丙三醇-8-香草醛醚(9)、(7S,8R)-二氢去氢二松柏醇-4-O-β-D-吡喃葡萄糖苷(10)、(—)-落叶松脂素-4-O-β-D-吡喃葡萄糖苷(11)、山柰酚-3-O-芸香糖苷(12)、槲皮素-3-O-芸香糖苷(13)、去氢吐叶醇(14)、布卢门醇A(15)、黑麦草内酯(16)、(E)-6-羟基-2,6-二甲基辛-2,7-二烯酸甲酯(17)、3-甲氧基酚-1-O-α-L-吡喃鼠李糖基-(1→6)-O-β-D-吡喃葡萄糖苷(18)、2-羟基苯并咪唑(19)、丁香醛(20)、1-苯基-1,2-乙二醇(21)。皮质酮诱导PC12细胞损伤的神经保护作用研究显示,化合物1~3、7、9对皮质酮诱导PC12细胞损伤具有显著的保护作用,化合物4、5、10、11、15~17表现出中等的保护作用。结论化合物1~9、11~12、14~21为首次从该植物中分离得到;部分化合物对皮质酮诱导PC12细胞损伤具有保护作用。Objective To study the chemical constituents of the ethyl acetate extract from the whole herb of Menyanthes trifoliate of Gentianaceae.Methods various chromatographic techniques,including positive phase silica gel column chromatography,thin-layer chromatography,AB-8 macroporous resin column chromatography,Sephadex LH-20 and preparative HPLC were used to separate and purify the chemical constituents.In vitro cell model was used for preliminary confirmation of the neuroprotective ability of compounds on corticosterone(CORT)-induced neurotoxicity in differentiated PC12 cells.Results Their structures were determined by various spectral data.Finally,21 compounds were isolated from the acetic ether extract of M.trifoliate and the structures were identified as 4-O-caffeoylquinic acid methyl ester(1),methylchlorogenate(2),chlorogenic acid(3),isofraxetin(4),isofraxidin(5),7R,7'R,8S,8'S-(+)-neo-olivil-4-O-β-D-glucopyranoside(6),conicaoside(7),(−)-syringaresinol(8),threo-(7R,8R)-guaiacylglycerol 8-vanillin ether(9),(7S,8R)-dihydrodehydrodiconiferyl alcohol-4-O-β-D-glucopyranoside(10),(−)-lariciresinol-4-O-β-D-glucoyranoside(11),kaempferol-3-O-rutinoside(12),quercetin-3-O-rutinoside(13),dehydrovomifoliol(14),blumenol A(15),loliolide(16),(E)-6-hydroxy-2,6-dimethylocta-2,7-dienoicacidmethylester(17),3-methoxyphenol 1-O-α-L-rhamnopyranosyl-(1→6)-O-β-D-glucopyranoside(18),2-hydroxybenzimidazole(19),syringaldehyde(20),1-phenyl-1,2-ethanediol(21).The neuroprotective effects investigation of compounds on CORT-induced neurotoxicity in differentiated PC12 cells showed that compounds 1-3,7,9 had significant protective effects on PC12 cells,and compounds 4,5,10,11,15-17 showed moderate protective effects.Conclusion Compounds 1-9,11-12,14-21 are isolated from M.trifoliate for the first time.Some compounds exert neuroprotective activity to corticosterone-induced injury of PC12 cells.

关 键 词：睡菜 抗焦虑 PC12细胞 神经保护 4-O-咖啡酰奎尼酸甲酯 绿原酸 异秦皮素 苏式-(7R 8R)-愈创木基丙三醇-8-香草醛醚 

分 类 号：R284.1[医药卫生—中药学]