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目的合成具有抗肿瘤活性的天然三萜皂苷giganteaside D。方法以齐墩果酸为起始原料,运用多种保护基策略,逐步构建二糖模块。结果经7步反应,首次完成giganteaside D的化学合成,总收率为29.2%,其结构经ESI-MS、1H-NMR和13C-NMR确证。结论体外MTT法活性筛选结果表明,giganteaside D对HeLa细胞株具有较强的抑制活性,IC50值为2.44μmol.L-1。与其差向异构体β-hederin相比,giganteaside D木糖C4的构型在一定程度上对生物活性产生了影响。
Objective To synthesize natural triterpenoid glycosides giganteaside D with antitumor activity. Methods oleanolic acid as starting material, the use of a variety of protective strategies, and gradually build the disaccharide module. Results The chemical synthesis of giganteaside D was completed for the first time in seven steps. The total yield was 29.2%. The structures of the compounds were confirmed by ESI-MS, 1H-NMR and 13C-NMR. Conclusion The results of in vitro MTT assay showed that giganteaside D had a strong inhibitory activity on HeLa cell line with IC50 value of 2.44μmol.L-1. The configuration of giganteaside D xylose C4, to a certain extent, has an impact on its biological activity compared to its epimer β-hederin.