Lipase Catalyzed Betulinic Acid Derivatives and its Cytotoxic Activity

Abstract

Betulinic acid, a triterpenoid found in many plant species, has attracted attention due to its important pharmacological properties, such as anti-cancer and anti-HIV activities. In order to obtain derivatives potentially useful for detailed pharmacological studies, derivatives were synthesized through the reaction of betulinic acid with benzoyl chloride and acetic anhydride using a lipase catalyst. Enzyme-catalyzed reaction of betulinic acid with benzoyl chloride yielded 3β-benzoil-lup-20(29)-ene-28-oic acid ester (BCL), whereas the acetic anhydride reaction yielded 3β-acetoxy-lup-20(29)-ene-28-oic acid ester (BAA). The BAA underwent further reaction with 1-decanol to produce 3b-acetoxy-lup-20(29)-ene-28 decanoate (BAAD). The prepared betulinic acid derivatives were tested for cytotoxic activity on three cancer cell lines in vitro: all tested compounds showed greater activity than betulinic acid.