title: Synthesis and cytotoxicity of bidesmosidic betulin and betulinic acid saponins.
abstract: The naturally occurring cytotoxic saponin 28-O-beta-d-glucopyranosylbetulinic acid 3beta-O-alpha-l-arabinopyranoside (3) was easily synthesized along with seven bidesmosidic saponins starting from the lupane-type triterpenoids betulin (1) and betulinic acid (2). As highlighted by the preliminary cytotoxicity evaluation against A549, DLD-1, MCF7, and PC-3 human cancer cell lines, the bidesmosidic betulin saponin 22a, bearing alpha-l-rhamnopyranoside moieties at both C-3 and C-28 positions, was determined to be a potent cytotoxic agent (IC(50) 1.8-1.9 microM).
authors.affiliation: Laboratoire d'Analyse et de Separation des Essences Vegetales (LASEVE), Departement des Sciences Fondamentales, Universite du Quebec a Chicoutimi, Chicoutimi, Quebec, Canada, G7H 2B1.
authors.forename: Charles
authors.initials: C
authors.lastname: Gauthier
authors.forename: Jean
authors.initials: J
authors.lastname: Legault
authors.forename: Serge
authors.initials: S
authors.lastname: Lavoie
authors.forename: Simon
authors.initials: S
authors.lastname: Rondeau
authors.forename: Samuel
authors.initials: S
authors.lastname: Tremblay
authors.forename: André
authors.initials: A
authors.lastname: Pichette
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D015394:Molecular Structure; D053978:Pentacyclic Triterpenes; D012503:Saponins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000094062:Betulinic Acid
chemical_list: C534865:28-O-beta-D-glucopyranosylbetulinic acid 3beta-O-alpha-L-arabinopyranoside; D000972:Antineoplastic Agents, Phytogenic; D053978:Pentacyclic Triterpenes; D012503:Saponins; D014315:Triterpenes; C480546:lupane; C002503:betulin; D000094062:Betulinic Acid