Synthesis, characterization and evaluation of 1-monoacylglycerols of unsaturated fatty acids as potential bioactive lipids

Abstract

The synthesis of 1-monoacylglycerols of selected unsaturated fatty acids and their antimicrobial and cytotoxicity activity is reported in the present study. The monoacylglycerols of fatty acids like undecenoic, oleic, linoleic and erucic acids were prepared by chemical esterification with solketal followed by deprotection. Fatty acids like alpha linolenic, gamma linolenic and ricinoleic acids were initially isolated from natural sources and further enriched in their respective methyl ester forms. The monoacylglycerols of ricinoleic and linolenic acid methyl esters were prepared by enzymatic transesterification with solketal using lipase from Candida antarctica followed by deprotection. The synthesized 1-monoacylglycerols were purified and characterized by spectral studies. The antimicrobial activity revealed that the monoacylglycerol of gamma linolenic acid was the most effective antibacterial followed by the monoacylglycerols of undecenoic and alpha linolenic acids. In the cytotoxicity assay against five cell lines, all the monoacylglycerols exhibited moderate activity but the activity was best against MCF7 Human Breast Adenocarcinoma cell lines.

Keywords

• 1-monoacylglycerols
• antimicrobial activity
• cytotoxicity
• fatty acids
• lipids
• synthesis