Semi-synthesis of nitrogen derivatives of oleanolic acid and effect on breast carcinoma MCF-7 cells

Abstract

Background: Oleanolic acid is a triterpenoid that has shown in vitro cytotoxic activity against human tumour cells and is known to be present in many higher plants.

Materials and methods: Oleanolic acid is known to have some biological potential including anticancer property. Oleanolic acid was isolated from the ethyl acetate fraction of Syzygium aromaticum seed with an aim of dervitatising the functional group and evaluating the biological activities of the semi-synthesised compounds. Acylation of the alcohol functional group of the oleanolic acid afforded the opportunity of hydrazine reaction to give 3-acetoleanolic hydrazide. Further reaction of 3-acetoleanolic hydrazide with benzyladehyde, glacial acetic acid and methanol resulted in the synthesis of the corresponding 3-acetoxyoleanolic hydrazone.

Results: The semi-synthetic oleanolic acid derivatives did not exhibit enhanced cytotoxic activity over oleanolic acid itself.

Conclusion: 3-acetoxyoleanolic hydrazide has a potent anticancer activity.

Keywords: 3-acetoxyoleanolic hydrazine; 3-acetoxyoleanolichydrazide; Syzygium aromaticum; breast cancer cells; oleanolic acid.