Anticancer activity of 3-O-acylated betulinic acid derivatives obtained by enzymatic synthesis.
An easy and efficient strategy to prepare betulinic acid esters with various anhydrides was used by the enzymatic synthesis method. It involves lipase-catalyzed acylation of betulinic acid with anhydrides as acylating agents in organic solvent. Lipase from Candida antarctica immobilized on an acrylic resin (Novozym 435) was employed as a biocatalyst. Several 3-O-acyl-betulinic acid derivatives were successfully obtained by this procedure. The anticancer activity of betulinic acid and its 3-O-acylated derivatives were then evaluated in vitro against human lung carcinoma (A549) and human ovarian (CAOV3) cancer cell lines. 3-O-glutaryl-betulinic acid, 3-O-acetyl-betulinic acid, and 3-O-succinyl-betulinic acid showed IC(50)<10 microg/ml against A549 cancer cell line tested and showed better cytotoxicity than betulinic acid. In an ovarian cancer cell line, all betulinic acid derivatives prepared showed weaker cytotoxicity than betulinic acid.
Ahmad
Faujan Bin H
FB
Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia. faujan@fsas.upm.edu.my
Ghaffari Moghaddam
Mansour
M
Basri
Mahiran
M
Abdul Rahman
Mohd Basyaruddin
MB
D000215:Acylation; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D055162:Biocatalysis; D002175:Candida / Q000201:enzymology; D045744:Cell Line, Tumor; D006801:Humans; D020128:Inhibitory Concentration 50; D008049:Lipase / Q000378:metabolism*; D053978:Pentacyclic Triterpenes; D012997:Solvents / Q000737:chemistry; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D000094062:Betulinic Acid
D000970:Antineoplastic Agents; D053978:Pentacyclic Triterpenes; D012997:Solvents; D014315:Triterpenes; D008049:Lipase; D000094062:Betulinic Acid