Elution factors of synthetic oxotriacylglycerols as an aid in identification of peroxidized natural triacylglycerols by reverse-phase high-performance liquid chromatography with electrospray mass spectrometry

Lipids. 1997 Nov;32(11):1211-8. doi: 10.1007/s11745-997-0155-4.

Abstract

Selected elution factors were determined for model oxotriacylglycerols as an aid in identification of the peroxidation products of natural triacylglycerols by reverse-phase high-performance liquid chromatography (HPLC) with electrospray mass spectrometry (LC/ES/MS). For this purpose synthetic triacylglycerols of known structure were converted to hydroperoxides, hydroxides, epoxides, and core aldehydes and their dinitrophenylhydrazones by published procedures. The oxotriacylglycerols were resolved by normal-phase thin-layer chromatography and reverse-phase HPLC, and the identities of the oxotriacylglycerols confirmed by LC/ES/MS. Elution factors of oxotriacylglycerols were determined in relation to a homologous series of saturated triacylglycerols, ranging from 24 to 54 acyl carbons, and analyzed by reverse-phase HPLC, using a gradient of 20-80% isopropanol in methanol as eluting solvent and an evaporative light-scattering detector. It was shown that the elution times varied with the nature of the functional group and its regiolocation in the triacylglycerol molecule. A total of 31 incremental elution factors were calculated from chromatography of 33 oxygenated and nonoxygenated triacylglycerol species, ranging in carbon number from 36 to 54 and in double-bond number from 0 to 6.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 2-Propanol
  • Chromatography, High Pressure Liquid*
  • Chromatography, Thin Layer
  • Hydrogen Peroxide / chemistry
  • Linoleic Acid / chemistry
  • Lipid Peroxidation*
  • Mass Spectrometry*
  • Methanol
  • Molecular Structure
  • Oleic Acid / chemistry
  • Ozone / chemistry
  • Triglycerides / analysis
  • Triglycerides / chemistry*
  • alpha-Linolenic Acid / chemistry

Substances

  • Triglycerides
  • alpha-Linolenic Acid
  • Oleic Acid
  • Ozone
  • Linoleic Acid
  • Hydrogen Peroxide
  • 2-Propanol
  • Methanol