1H NMR Analysis of Oz o ne-Treated Grapeseed, Olive and Sunflower Seed Oils
E. Lynch1*, M. Grootveld2, J. Holm es 2, C. Silwood2, A. W.D. Claxson2, J. Prinz2, H. TOMS3, M. TURNER2. ( 1Oral Health Research Centre, QUB, N.I., 2 St. BTMW’s, the Ro yal London School of Medicine and Dentistry and 3Chemistry, QMU, London, UK)
Aim: Ozonated oils are being used for their antimicrobial actions as a pharmaceutical approach to manage a variety of medical problems. The aim of this study was to assess which compounds might be responsible for these therapeutic benefits within ozonated oils. Methods: Aliquots (40.0 ml.) of commercially available grapeseed, olive and sun flower seed oils (GO, OO and SO respectively) were divided into two equivalent portions. The first was treated with Ozone (O3)* for 10 minutes; the second group of portions served as controls. 0.25 ml of each sample was diluted to a volume of 0.75 ml with a 5.00 X10-3 mol.dm-3 solution of 1,3,5-trichlorobenzene (1H NMR standard) in deuterated chloroform (CDCl3), the latter serving as a field frequency lock. 1H NMR spectra of these samples were acquired on a Bruker AMX-600 spectrometer. Chemical shift values were referenced to the residual chloroform singlet resonance at 7.262 ppm.
Results: Treatment of each oil with O3 gave rise to the consumption of polyunsaturated fatty acids (PUFAs) (i.e. significant reductions in their monoand bisallylic-CH2 group resonances located at 2.06 and 2.76 pp m respectively, and also that of the vinylic protons at 5.38 ppm), consistent with their ozonylation. Indeed, signals present in the 5.10- 5.25 ppm regions of the ozonylated GO and SO spectra are assignable to ozonides. Further effect of O3 to the oils included the production of aldehydes, i.e. -CH2CHO aldehydic group triplet resonances at 9.65 (ozonylated GO and SO) and 9.74 ppm (all ozonylated oils). These aldehydic species arise from the decomposition of ozonides
Conclusion: Ozone treatment of commercially available grapeseed, olive and sunflower seed oils gives rise to ozonides and aldehydes, which can be partly responsible for antimicrobial properties of these ozonated oils. *(HealOzone Unit, CurOzone USA)