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.
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.
Sjövall
O
O
Banting and Best Department of Medical Research, University of Toronto, Ontario, Canada.
Kuksis
A
A
Marai
L
L
Myher
J J
JJ
D019840:2-Propanol; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D006861:Hydrogen Peroxide / Q000737:chemistry; D019787:Linoleic Acid / Q000737:chemistry; D015227:Lipid Peroxidation; D013058:Mass Spectrometry; D000432:Methanol; D015394:Molecular Structure; D019301:Oleic Acid / Q000737:chemistry; D010126:Ozone / Q000737:chemistry; D014280:Triglycerides / Q000032:analysis / Q000737:chemistry*; D017962:alpha-Linolenic Acid / Q000737:chemistry
D014280:Triglycerides; D017962:alpha-Linolenic Acid; D019301:Oleic Acid; D010126:Ozone; D019787:Linoleic Acid; D006861:Hydrogen Peroxide; D019840:2-Propanol; D000432:Methanol