毛果南烛叶中的三萜皂苷化合物及其抗肿瘤活性

Triterpenoid Glycosides from the Leaves of Lyonia ovalifolia var. hebecarpa and Their Antitumor Activities

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.