Synthesis and cytotoxicity of bidesmosidic betulin and betulinic acid saponins.
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).
Gauthier
Charles
C
Laboratoire d'Analyse et de Separation des Essences Vegetales (LASEVE), Departement des Sciences Fondamentales, Universite du Quebec a Chicoutimi, Chicoutimi, Quebec, Canada, G7H 2B1.
Legault
Jean
J
Lavoie
Serge
S
Rondeau
Simon
S
Tremblay
Samuel
S
Pichette
André
A
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
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