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Abstract
γ-Linolenic acid (GLA) has been reported as a potential anti-cancer and anti-inflammatory agent and has received substantial attention in cancer care research. One of the many proposed mechanisms for GLA biological activity is free radical-mediated lipid peroxidation. However, no direct evidence has been obtained for the formation of GLA-derived radicals. In this study, a combination of LC/ESR and LC/MS was used with α-[4-pyridyl-1-oxide]-N-tert-butyl nitrone (POBN) to profile the carbon-centred radicals that are generated in lipoxygenase-catalysed GLA peroxidation. A total of four classes of GLA-derived radicals were characterized including GLA-alkyl, epoxyallylic, dihydroxyallylic radicals and a variety of carbon-centred radicals stemming from the β-scissions of GLA-alkoxyl radicals. By means of an internal standard in LC/MS, one also quantified each radical adduct in all its redox forms, including an ESR-active form and two ESR-silent forms. The results provided a good starting point for ongoing research in defining the possible biological effects of radicals generated from GLA peroxidation.
| Abbreviations | ||
| ACN | = | acetonitrile |
| EIC | = | extracted ion chromatography |
| ESR | = | electron spin resonance |
| GLA | = | gamma linolenic acid (all-cis-6, 9, 12-octadecatrienoic acid) |
| HOAc | = | glacial acetic acid |
| HPLC (LC) | = | high performance liquid chromatography |
| I.S. | = | internal standard |
| LA | = | linoleic acid (cis, cis-9, 12-octadecadienoic acid) |
| LOX | = | lipoxygenase |
| L• | = | lipid alkyl radicals |
| •L(OH)2 | = | lipid dihydroxyallylic radicals |
| MRM | = | multiple reaction monitoring |
| OL• | = | lipid epoxyallylic radicals |
| POBN | = | α-[4-pyridyl-1-oxide]-N-tert-butyl nitrone |
| PUFAs | = | polyunsaturated fatty acids |
| TIC | = | total ion current |
| tR | = | retention time. |
| Abbreviations | ||
| ACN | = | acetonitrile |
| EIC | = | extracted ion chromatography |
| ESR | = | electron spin resonance |
| GLA | = | gamma linolenic acid (all-cis-6, 9, 12-octadecatrienoic acid) |
| HOAc | = | glacial acetic acid |
| HPLC (LC) | = | high performance liquid chromatography |
| I.S. | = | internal standard |
| LA | = | linoleic acid (cis, cis-9, 12-octadecadienoic acid) |
| LOX | = | lipoxygenase |
| L• | = | lipid alkyl radicals |
| •L(OH)2 | = | lipid dihydroxyallylic radicals |
| MRM | = | multiple reaction monitoring |
| OL• | = | lipid epoxyallylic radicals |
| POBN | = | α-[4-pyridyl-1-oxide]-N-tert-butyl nitrone |
| PUFAs | = | polyunsaturated fatty acids |
| TIC | = | total ion current |
| tR | = | retention time. |