title: Synthesis of stryphnoside A, a triterpene saponin isolated from the pericarps of Stryphnodendron fissuratum.
abstract: Stryphnoside A, α-l-rhamnopyranosyl 3β-O-[α-l-arabinopyranosyl-(1→4)-β-d-xylopyranosyl-(1→2)-β-d-glucopyranosyl]-2α-hydroxyolean-12-en-28-oate, has been synthesized in 11 steps in 15% overall yield starting from the naturally abundant oleanolic acid. Condensation of a partially protected glucopyranosyl donor and 2α,3β-dihydroxyolean-12-en-28-oic acid derivative using inverse glycosylation procedure has significantly simplified the target saponin synthesis. Stryphnoside A exhibited weak cytotoxic activities against tumor cells HeLa, A549, and HepG2 with IC(50) at mM level.
authors.affiliation: Chinese Academy of Sciences, Beijing 100085, China.
authors.forename: Xun
authors.initials: X
authors.lastname: Lv
authors.forename: Shouyi
authors.initials: S
authors.lastname: Yu
authors.forename: Jing
authors.initials: J
authors.lastname: Wang
authors.forename: Yuguo
authors.initials: Y
authors.lastname: Du
mesh_terms: D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D007887:Fabaceae / Q000737:chemistry*; D006367:HeLa Cells; D056945:Hep G2 Cells; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry*; D012503:Saponins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D010936:Plant Extracts; D012503:Saponins; D014315:Triterpenes