太白银莲花地上部分三萜皂苷类化学成分的研究

Triterpenoid saponins from aerial parts of Anemone taipaiensis

目的研究太白银莲花Anemone taipaiensis地上部分化学成分,并初步评估其肿瘤细胞增殖抑制活性。方法采用正相硅胶、Sephadex LH-20凝胶、ODS反相柱色谱以及半制备高效液相色谱等手段进行分离纯化;根据波谱数据(1D-NMR、2D-NMR及MS)和理化性质鉴定化合物结构;采用MTT法评估化合物对2种人源肿瘤细胞(人急性早幼粒白血病HL-60细胞和人肝癌HepG2细胞)的增殖抑制活性。结果从太白银莲花地上部分70%乙醇提取物的正丁醇萃取部位分离得到7个齐墩果烷型三萜皂苷类化合物,分别鉴定为常春藤皂苷元-3β-O-β-D-吡喃葡萄糖-(1→3)-α-L-吡喃鼠李糖-(1→2)-α-L-吡喃阿拉伯糖(1→4)-β-D-吡喃葡萄糖苷(1)、3β-O-β-D-吡喃木糖-(1→3)-α-L-吡喃鼠李糖-(1→2)-α-L-吡喃阿拉伯糖-齐墩果酸-28-O-β-D-吡喃葡萄糖酯苷(2)、cernusoide C(3)、medicago-saponin P1(4)、常春藤皂苷元-3β-O-β-D-吡喃木糖-(1→3)-α-L-吡喃鼠李糖-(1→2)-[β-D-吡喃葡萄糖-(1→4)]-α-L-吡喃阿拉伯糖苷(5)、hederacholichiside F(6)和3β-O-α-L-吡喃鼠李糖-(1→2)-α-L-吡喃阿拉伯糖-齐墩果酸-28-O-α-L-吡喃鼠李糖-(1→4)-β-D-吡喃葡萄糖-(1→6)-β-D-吡喃葡萄糖-(1→4)-α-L-吡喃鼠李糖-(1→4)-β-D-吡喃葡萄糖-(1→6)-β-D-吡喃葡萄糖酯苷(7);化合物1、2和5显示出不同程度的肿瘤细胞增殖抑制活性。结论化合物1为新化合物,命名为太白银莲花皂苷C;化合物4为首次从银莲花属植物中分离得到;化合物5对HL-60细胞和HepG2细胞有显著增殖抑制活性,半数抑制浓度(median inhibition concentration,IC_(50))值分别为5.79和3.42μmol/L。

Objective To study the chemical constituents from the aerial parts of Anemone taipaiensis and their preliminary antiproliferatory activity in tumor cells.Methods The n-butanol extract of 70%ethanol extract from the aerial parts of this plant was separated by normal silica gel,Sephadex LH-20 gel,reversed phase ODS column chromatography and semi-preparative high performance liquid chromatography.The structures of obtained compounds were identified by spectral analysis(1D-NMR,2D-NMR and MS)and physicochemical properties.The antiproliferatory activity against two human tumor cells(HL-60 and HepG2)was evaluated by MTT assay.Results Seven oleanane-type triterpenoid saponins were obtained and identified as hederagenin-3β-O-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→4)-β-D-glucopyranoside(1),3β-O-β-Dxylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl-oleanolic acid-28-O-β-D-glucopyranosyl ester(2),cernusoide C(3),medicago-saponin P1(4),hederagenin-3β-O-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranoside(5),hederacholichiside F(6)and 3β-O-α-L-rhamnopyranosyl-(1→2)-α-Larabinopyranosyl-oleanolic acid-28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl-(1→4)-α-Lrhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester(7).Compounds 1,2 and 5 displayed antiproliferation activities on tumor cells.Conclusion Compound 1 is a new compound named taipaienoside C.Compound 4 is isolated form the genus Anemone for the first time.Compound 5 displayed significant antiproliferation activity against HL-60 cells and HepG2 cells with IC_(50) values of 5.79 and 3.42μmol/L,respectively.