诸葛菜种子中1个新的酚苷类化合物及其肝保护活性研究  

Study on A New Phenolic Glycoside with Liver Protective Activity from Seeds of Orychophragmus Violaceus

作　　者：王柯莉 侯勇 马国需[2] 许旭东[2] 闵芳芳 宋玉清 林凤梅 WANG Ke-li;HOU Yong;MA Guo-xu;XU Xu-dong;MIN Fang-fang;SONG Yu-qing;LIN Feng-mei(The Affiliated Chuzhou Hospital of Anhui Medical University,Chuzhou 239000,China;Institute of Medical Plant Development,Chinese Academy of Medical Sciences&Peking Union Medical College,Beijing 100193,China)

机构地区：[1]安徽医科大学附属滁州医院,安徽滁州239000 [2]中国医学科学院北京协和医学院药用植物研究所,北京100193

出　　处：《食品与药品》2025年第2期142-147,共6页Food and Drug

摘　　要：目的 研究诸葛菜Orychophragmus violaceus种子水提取部位的主要化学成分并评价其肝保护活性。方法取诸葛菜种子20 kg,以10倍量纯水煎煮提取,所得水煎液浓缩后,采用大孔吸附树脂色谱、硅胶柱色谱、Sephadex LH-20凝胶柱色谱、ODS柱色谱、MCI柱色谱、半制备高效液相色谱(HPLC)、重结晶等进行分离纯化,并根据高分辨电喷雾质谱(HR-ESI-MS)、核磁共振氢谱(^(1)H NMR)、核磁共振碳谱(^(13)C NMR)、氢-氢相关谱(^(1)H-^(1)H COSY)、异核单量子相关谱(HSQC)、异核多键相关谱(HMBC)、核奥氏效应谱(NOESY)等波谱学方法进行结构鉴定。采用对乙酰氨基酚(APAP)诱导的人肝癌细胞(HepG2)损伤模型对新化合物进行肝细胞保护活性评价。结果 从诸葛菜种子水提取部位中分离得到10个化合物,鉴定结构为诸葛菜酚苷A (1),(-)-(7S,8R,7'E)-4,7,9,4',9'-pentahydroxy-3,5,3',5'-tetramethoxy-8,4'-oxyneolignan-7'-ene-4,9'-di-O-β-D-glucopyranoside (2),7S,8R,8'R-(-)-5-methoxylariciresinol-4,4'-bis-O-β-D-glucopyranoside(3),甲基-2-O-β-D-吡喃葡萄糖基苯甲酸(4),异它乔糖甙(5),对羟基苯丙酸(6),4-羟基间苯二甲酸(7),桂皮酸(8),原儿茶酸(9),水杨酸(10)。浓度为10μmol/L时,化合物1与阳性对照联苯双酯作用相当,在APAP诱导的HepG2细胞损伤模型中,具有显著的肝细胞保护作用。结论 化合物1为自然界未发现过的新酚苷类化合物,命名为诸葛菜酚苷A,其具有显著的肝细胞保护活性。化合物1~8为首次从诸葛菜属植物中分离得到。Objective To study the chemical constituents of aqueous extract from the seeds of Orychophragmus violaceus.Methods 20 kg of seeds of Orychophragmus violaceus were extracted with water and concentrated under reduced pressure.Then the extract was isolated and purified by macroporous adsorption resin chromatography,silica gel column chromatography,Sephadex LH-20 gel column chromatography,ODS column chromatography,MCI column chromatography,semi-preparative HPLC,recrystallization and so on.Their structures were identified and determined based on the spectroscopic methods,like HR-ESI-MS,~1H NMR,^(13)C NMR,~1H-~1H COSY,HSQC,HMBC and NOESY.The hepatoprotective activity of compound 1 was evaluated by APAP induced human liver cancer cell line(HepG2) injury model.Results Ten compounds were isolated from the aqueous extract of the seeds of Orychophragmus violaceus,and they were identified as orychophragvioside A(1),(-)-(7S,8R,7'E)-4,7,9,4',9'-pentahydroxy-3,5,3',5'-tetramethoxy-8,4'-oxyneolignan-7'-ene-4,9'-di-O-β-D-glucopyranoside(2),7S,8R,8 'R-(-)-5-metho xylariciresinol-4,4'-bis-O-β-D-glucopyrano side(3),methyl-2-O-β-D-glucopyrano sylbe nzoate(4),isotachioside(5),p-hydroxyphenylpropionic acid(6),4-hydroxy isophthalic acid(7),cinnamic acid(8),protocatechuic acid(9),salicylic acid(10),respectively.At the concentration of 10 μmol/L,compound 1 exhibited significant hepatoprotective effect in APAP-induced HepG2 cell injury model,which was comparable to the positive control bifendate.Conclusion Compound 1 is a new phenolic glycoside compound that has not been found in nature,and is named orychophragvioside A,which has significant hepatoprotective activity.Compounds 1-8 are isolated from the genus Orychophragmus for the first time.

关 键 词：诸葛菜 诸葛菜酚苷A 新化合物 结构鉴定 肝保护活性 

分 类 号：R284[医药卫生—中药学]