[关键词]
[摘要]
目的 研究灰毡毛忍冬Lonicera macranthoides花蕾中的化学成分。方法 采用正相硅胶、ODS、Sephadex LH-20、半制备高效液相色谱等方法对灰毡毛忍冬花蕾的水提取物进行分离纯化,采用NMR、MS等波谱方法进行鉴定结构,采用MTT法研究化合物的细胞毒活性。结果 从灰毡毛忍冬花蕾中分离得到了7个三萜类化合物,分别鉴定为3-O-β-D-吡喃葡萄糖基-(1→4)-α-L-吡喃阿拉伯糖基常春藤皂苷元28-O-β-D-吡喃葡萄糖酯苷(1)、3-O-α-L-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖基齐墩果酸28-O-α-L-吡喃鼠李糖基-(1→4)-O-β-D-吡喃葡萄糖基-(1→6)-β-D-吡喃葡萄糖基酯苷(2)、3-O-α-L-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖基常春藤皂苷元28-O-β-D-吡喃葡萄糖酯苷(3)、3-O-α-L-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖基常春藤皂苷元28-O-α-L-吡喃鼠李糖基-(1→4)-O-β-D-吡喃葡萄糖基-(1→6)-β-D-吡喃葡萄糖基酯苷(4)、3-O-α-L-吡喃阿拉伯糖基常春藤皂苷元28-O-α-L-吡喃鼠李糖基-(1→4)-β-D-吡喃葡萄糖基-(1→6)-β-D-吡喃葡萄糖基酯苷(5)、3-O-β-D-吡喃葡萄糖基-(1→4)-α-L-吡喃阿拉伯糖基常春藤皂苷元28-O-α-L-吡喃鼠李糖基-(1→4)-β-D-吡喃葡萄糖基-(1→6)-β-D-吡喃葡萄糖基酯苷(6)、3-O-β-D-吡喃葡萄糖基-(1→3)-α-L-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖基常春藤皂苷元28-O-α-L-吡喃鼠李糖基-(1→4)-β-D-吡喃葡萄糖基-(1→6)-β-D-吡喃葡萄糖基酯苷(7)。结论 化合物1为新化合物,命名为灰毡毛忍冬皂苷丙;化合物2~7为首次从该植物中分离得到。细胞毒活性结果显示,化合物1、4和5对人宫颈癌HeLa细胞均有一定的抑制作用,其IC50值分别为54.3、43.9、61.2 μmol/L。
[Key word]
[Abstract]
Objective To study the chemical constituents from the flower buds of Lonicera macranthoides and their antitumor activities. Methods The constituents were separated by chromatography of silica gel, ODS, Sephadex LH20, and semi-pre HPLC. Their structures were elucidated by spectral means. The in vitro cytotoxic activities of the isolated compounds were studied by MTT method. Results Seven compounds were isolated and identified as 3-O-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl-hederagenin 28-O-β-D-glucopyranosyl ester (1), 3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl-oleanolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (2), 3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl-hederagenin 28-O-β-D-glucopyranosyl ester (3), 3-O-α-L-rhamnnopyranosyl-(1→2)-α-L-arabinopyranosyl-hederagenin 28-O-α-L-rhamnopyransyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (4), 3-O-α-L-arabinopyranosyl-hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (5), 3-O-β-D-glucopyra-nosyl-(1→4)-α-L-arabinopyranosyl-hederagenin 28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside ester (6), and 3-O-β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl-hederagenin 28-O-α-L-rhamno-pyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (7). Conclusion Compound 1 is a new compound named macranthoidin C, and compounds 2-7 are isolated from L. macranthoides for the first time. Compounds 1, 4, and 5 show cytotoxicities against HeLa cells with IC50 of 54.3, 43.9 and 61.2 μmol/L, respectively.
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[基金项目]
湖北省自然科学基金青年项目(2018CFB318)