Anticancer Activity of 3-O-Acylated Betulinic Acid Derivatives Obtained by Enzymatic Synthesis | Zendy

Faujan Ahmad | Zendy; Mansour GhaffariMoghaddam | Zendy; Mahiran Basri | Zendy; Mohd Basyaruddin Abdul Rahman | Zendy

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Anticancer Activity of 3-O-Acylated Betulinic Acid Derivatives Obtained by Enzymatic Synthesis

Author(s) -

Faujan Ahmad,

Mansour GhaffariMoghaddam,

Mahiran Basri,

Mohd Basyaruddin Abdul Rahman

Publication year - 2010

Publication title -

bioscience biotechnology and biochemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.509

H-Index - 116

eISSN - 1347-6947

pISSN - 0916-8451

DOI - 10.1271/bbb.90917

Subject(s) - betulinic acid , chemistry , lipase , acylation , cytotoxicity , enzyme , organic chemistry , biochemistry , in vitro , catalysis , biology , genetics

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.

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