蝉翼藤根中木质素苷及蔗糖酯成分研究
2017-07-13王芷杨学东査海燕郭丽娜沈丹徐丽
王芷+杨学东+査海燕+郭丽娜+沈丹+徐丽珍+杨世林
[摘要] 运用硅胶、MPLC和制备HPLC等柱色谱方法对蝉翼藤根的化学成分进行分离,并通过理化性质和MS、NMR波谱数据进行结构鉴定。从蝉翼藤根的95%乙醇提取物中分离鉴定了9个化合物,包括5个木质素苷acernikol-4″-O-β-D-glucopyranoside (1), (7R, 8S )-dihydrodehydrodiconiferyl alcohol 9-O-β-D-glucopyranoside (2), (7R, 8S )-dihydrodehydrodiconiferyl alcohol 4-O-β-D-glucopyranoside (3), (7R, 8S)-dihydrodehydrodiconiferyl alcohol 9′-O-β-D-glucopyranoside (4), (7R, 8S)-5-methoxydihydrodehy drodiconiferyl alcohol 4-O-β-D-glucopyranoside (5); 3个蔗糖酯3, 6′-O-diferuloylsucrose (6), 3-O-feruloyl-6′-O-sinapoylsucrose (7), sibricose A5 (8); 1个有机酸酯mehyl ferulate(9)。化合物1~5,8, 9为首次从蝉翼藤属中分离得到。采用MTT法测定了化合物对肺癌细胞株A549、宫颈癌细胞株Hela和乳腺癌细胞株MCF-7的细胞毒活性。结果表明化合物2,3和7对所测试的人源肿瘤细胞具有较弱的抑制活性。
[关键词] 蝉翼藤属; 蝉翼藤; 木质素苷; 蔗糖酯; 细胞毒活性
[Abstract] Nine compounds, including five lignan glycosides (1-5), three sucrose esters (6-8), and one organic acid ester (9), were isolated from the ethanol extract of the roots of Securidaca inappendiculata by various chromatographic methods including silica gel, MPLC and preparative HPLC. Their structures were elucidated as acernikol-4″-O-β-D-glucopyranoside (1), (7R, 8S)-dihydrodehydrodiconiferyl alcohol 9-O-β-D-glucopyranoside (2), (7R, 8S)-dihydrodehydrodiconiferyl alcohol 4-O-β-D-glucopyranoside (3), (7R, 8S)-dihydrodehydrodiconiferyl alcohol 9′-O-β-D-glucopyranoside (4), (7R, 8S)-5-methoxydihydrodehy-drodiconiferyl alcohol 4-O-β-D-glucopyranoside (5), 3, 6′-O-diferuloylsucrose (6), 3-O-feruloyl-6′-O-sinapoylsucrose (7), sibricose A5 (8), and mehyl ferulate (9) on the basis of 1H-, 13C-NMR and MS experiments. Compounds 1-5, 8, and 9 were isolated from the Securidaca genus for the first time. Compounds 2, 3, and 7 exhibited weak cytotoxic activities against Hela and MCF-7 cell lines.
[Key words] Securidaca; Securidaca inappendiculata; lignan glycosides; sucrose esters; cytotoxic activity
蟬翼藤Securidaca inappendiculata Hassk,又名五味藤,为远志科Polygalaceae蝉翼藤属的一种攀援植物,主要分布于我国的云南、广西、广东、海南及东南亚、南亚的热带地区。蝉翼藤根茎味辛、甘、苦,性微寒,有活血化瘀、消肿止痛和清热利尿的功效[1]。将其作为主药之一的广西玉林牌正骨水被2015年版《中国药典》收载,应用于跌打损伤、骨折脱位及消除运动疲劳[2]。文献报道从蝉翼藤中已分离鉴定出酮[3-4]、寡糖酯[5]、皂苷[6-7]、二苯酮[8-9]、半萜酸苷[10]、甾苷[11]、有机酸[12]等化学成分。本文在前期抗肿瘤活性皂苷类成分研究的基础上,对蝉翼藤根的95%乙醇提取物开展进一步研究,从中分离并鉴定了5个木质素苷类化合物,3个蔗糖酯化合物及1个有机酸酯化合物。化合物1~5,8,9为首次从蝉翼藤属中分离得到。在此基础上,采用MTT法测定了化合物1~3,6,7对人源肿瘤细胞A549,Hela及MCF7的细胞毒活性。
1 材料
Bruker Avance Ⅲ核磁共振仪(600,400 MHz,瑞士Bruker公司);Agilent 6420 三重四级杆质谱仪(美国Agilent公司);……
