Synthesis and cytotoxicity of lupane-type triterpenoid glyceryl esters.
A new series of betulinic acid and betulin derivatives were synthesized by introducing a D-glycerol moiety at the C-3 and/or C-28 positions of the lupane skeleton. The resulting glyceryl esters were evaluated in vitro for their cytotoxic activity against A549, DLD-1 and WS1 human cell lines. The structure-activity relationships study revealed that the incorporation of a glycerol unit at the C-3 or C-28 position of the lupane core resulted in compounds exhibiting potent cytotoxic activity together with decreased liposolubility.
Université du Québec à Chicoutimi, Laboratoire d'analyse et de séparation des essences végétales (LASEVE), Département des sciences fondamentales, 555 boul. de l'Université, Chicoutimi (Québec), Canada G7H 2B1.
Dominic
D
Thibeault
Charles
C
Gauthier
Jean
J
Legault
Jimmy
J
Bouchard
Louis
L
Gagné
André
A
Pichette
D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D004952:Esters / Q000138:chemical synthesis* / Q000378:metabolism; D005990:Glycerol / Q000737:chemistry*; D006801:Humans; D015394:Molecular Structure; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000737:chemistry*; D053978:Pentacyclic Triterpenes
D004952:Esters; D005990:Glycerol; D014315:Triterpenes; C480546:lupane; D053978:Pentacyclic Triterpenes