Spectroscopic characterization of ozonides with biological activity

Ozonation reactions are very important in fatty acid chemistry since their ozonation products are involved in vital biological processes. When an unsa turated acid reacts with ozone in presence of an organic solvent, Criegee o zonides are produced according to the Criegee mechanism. These ozonides are relatively stable compounds, thus, in the organism they have biological ef fects at distant sites from the site they are formed. The antimicrobial act ivity of ozonized sunflower oil (Oleozon(R)) has been previously well docum ented. We have suggested that ozonides are involved in the antimicrobial ef fect of Oleozon(R). In this study we try to demonstrate this hypothesis. Oz onides were obtained by total reaction of ozone gas with a sample of methyl oleate in an organic solvent (hexane). Proton Nuclear Magnetic Resonance ( H-1 NMR) technique was used for identification of ozonides in ozonation pro ducts, whereas biological evaluation was done by determining Minimum Inhibi tory Concentration (MIC), Minimum Bactericidal Concentration (MBC) and Mini mum Fungicidal Concentration (MFC) of ozonation products of different micro organism. The ozonide signal was identified in the Oleozon(R) and ozonized methyl oleate while in sunflower oil was not. Ozonation products from methy l oleate, in our reaction conditions, were spectroscopically found to be on ly ozonides. MICs for ozonides from ozonized methyl oleate were from 2.3 to 28 mg/mL, whereas MBC and MFC were 460 mg/mL comparable with those from Ol eozon(R). These results demonstrate that ozonides are one of the active spe cies of Oleozon(R).