Synthesis and evaluation of dioleoyl glyceric acids showing antitrypsin activity

Previously, Lešová et al. reported the isolation and identification of metabolite OR-1, showing antitrypsin activity, produced during fermentation by Penicillium funiculosum. The structure of OR-1 was a mixture of glyceric acid (GA), esterified with C-C fatty acids, and oleic acid (C18:1) as the most predominant fatty acid (Folia Microbiol. 46, 21-23, 2001). In this study, dioleoyl D-GA and dioleoyl L-GA were synthesized via diesterification with oleoyl chloride, and their antitrypsin activities were evaluated using both a disk diffusion method and spectral absorption measurements. The results show that both compounds and their equivalent mixtures possess antitrypsin activities; however, their IC values (approximately 2 mM) are much higher than that of OR-1 (4.25 μM), suggesting that dioleoyl GA does not play a major role in the OR-1 antitrypsin activity. © 2011 by Japan Oil Chemists' Society.