title: Synthesis and biological evaluation of Raddeanin A, a triterpene saponin isolated from Anemone raddeana.
abstract: First, Raddeanin A, a cytotoxic oleanane-type triterpenoid saponin isolated from Anemone raddeana REGEL, was synthesized. Stepwise glycosylation was adopted in the synthesis from oleanolic acid, employing arabinosyl, glucosyl and rhamnosyl trichloroacetimidate as donors. The chemical structure of Raddeanin A was confirmed by means of (1)H-NMR, (13)C-NMR, IR, MS and elemental analysis, which elucidated the structure to be 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside oleanolic acid. Biological activity tests showed that in the range of low concentrations, Raddeanin A displayed moderate inhibitory activity against histone deacetylases (HDACs), indicating that the HDACs' inhibitory activity of Raddeanin A may contribute to its cytotoxicity.
authors.affiliation: Bioengineering College, Xihua University.
authors.forename: Shan
authors.initials: S
authors.lastname: Qian
authors.forename: Quan Long
authors.initials: QL
authors.lastname: Chen
authors.forename: Jin Long
authors.initials: JL
authors.lastname: Guan
authors.forename: Yong
authors.initials: Y
authors.lastname: Wu
authors.forename: Zhou Yu
authors.initials: ZY
authors.lastname: Wang
mesh_terms: D031883:Anemone / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D006367:HeLa Cells; D056572:Histone Deacetylase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D006801:Humans; D012503:Saponins / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D056572:Histone Deacetylase Inhibitors; D012503:Saponins; C584473:raddeanin A