毛果南烛叶中的三萜皂苷化合物及其抗肿瘤活性
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摘要
利用柱层析和高效液相色谱等分离技术从毛果南烛Lyonia ovalifolia var.hebecarpa的叶中分离得到了3个三萜皂苷类化合物,借助HRESIMS和NMR等波谱手段以及化学方法鉴定其结构分别3β-O-ɑ-L-阿拉伯吡喃糖氧基-齐墩果-12-烯-23,25-二醇(1)、3β-O-α-L-阿拉伯吡喃糖氧基-齐墩果-12-烯-1β,23-二醇(2)和25-羟基-3β-O-β-D-葡萄糖吡喃糖氧基-24α-O-α-L-阿拉伯吡喃糖氧基-9,10-开环-羊毛脂烷-10-烯-30-酸(3).化合物1及其苷元是新化合物,已知化合物2和3均为首次从该植物中分离得到.首次对化合物2及其苷元进行了NMR数据归属.同时,筛选了所得3个三萜皂苷化合物1~3的体外抗肿瘤活性,结果显示化合物2对五种肿瘤细胞HL-60、MCF-7、SMMC-7221、A-549和SW480的增殖均有显著的抑制作用,其半数抑制浓度(IC50)分别为(16.35±0.25)、(17.05±0.52)、(17.66±0.21)、(15.87±0.26)和(12.30±0.36)μmol·L-1,而且对MCF-7、A-549和SW480细胞增殖的抑制活性均优于阳性对照药物顺铂.
Three triterpenoid glycosides were isolated from the leaves of Lyonia ovalifolia var. hebecarpa by separation techniques such as column chromatograph and HPLC, and their structures were determined to be 3β-O-α-L-arabinopyranosyloxy-olean-12-ene-23,25-diol(1), 3β-O-α-L-arabinopyranosyloxy-olean-12-ene-1β,23-diol(2), and 3α-[(β-D-glucopyranosyl)-oxy]-24α-[(α-L-arabinopyranosyl)-oxy]-25-hydroxy-9,10-seco-cycloaran-1(10)-en-30-oic acid(3), respectively, by HRESIMS and NMR data analysis, as well as chemical methods. Compound 1 and its aglycone are new compounds, and compounds 2 and 3 were isolated from Lyonia ovalifolia var. hebecarpa for the first time. This is the first report of the NMR data assignment of compound 2 and its aglycone. The in vitro anti-tumor activities of compounds 1~3 were evaluated, and compound 2 showed anti-proliferation activities against five cancer cell lines HL-60, MCF-7, SMMC-7221, A-549 and SW480 with IC50 values of(16.35±0.25),(17.05±0.52),(17.66±0.21),(15.87±0.26) and(12.30±0.36) μmol·L-1, respectively, and showed more potent anti-proliferation than the positive control, cis-platin, against MCF-7, A-549, and SW480 cell lines.
Three triterpenoid glycosides were isolated from the leaves of Lyonia ovalifolia var. hebecarpa by separation techniques such as column chromatograph and HPLC, and their structures were determined to be 3β-O-α-L-arabinopyranosyloxy-olean-12-ene-23,25-diol(1), 3β-O-α-L-arabinopyranosyloxy-olean-12-ene-1β,23-diol(2), and 3α-[(β-D-glucopyranosyl)-oxy]-24α-[(α-L-arabinopyranosyl)-oxy]-25-hydroxy-9,10-seco-cycloaran-1(10)-en-30-oic acid(3), respectively, by HRESIMS and NMR data analysis, as well as chemical methods. Compound 1 and its aglycone are new compounds, and compounds 2 and 3 were isolated from Lyonia ovalifolia var. hebecarpa for the first time. This is the first report of the NMR data assignment of compound 2 and its aglycone. The in vitro anti-tumor activities of compounds 1~3 were evaluated, and compound 2 showed anti-proliferation activities against five cancer cell lines HL-60, MCF-7, SMMC-7221, A-549 and SW480 with IC50 values of(16.35±0.25),(17.05±0.52),(17.66±0.21),(15.87±0.26) and(12.30±0.36) μmol·L-1, respectively, and showed more potent anti-proliferation than the positive control, cis-platin, against MCF-7, A-549, and SW480 cell lines.
引文
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