Abstract
Extra virgin olive oil (EVOO) and olives, key sources of unsaturated fatty acids in the Mediterranean diet, provide health benefits to humans. Nitric oxide (•NO) and nitrite (NO2 −)-dependent reactions of unsaturated fatty acids yield electrophilic nitroalkene derivatives (NO2-FA) that manifest salutary pleiotropic cell signaling responses in mammals. Herein, the endogenous presence of NO2-FA in both EVOO and fresh olives was demonstrated by mass spectrometry. The electrophilic nature of these species was affirmed by the detection of significant levels of protein cysteine adducts of nitro-oleic acid (NO2-OA-cysteine) in fresh olives, especially in the peel. Further nitration of EVOO by NO2 − under acidic gastric digestive conditions revealed that human consumption of olive lipids will produce additional nitro-conjugated linoleic acid (NO2-cLA) and nitro-oleic acid (NO2-OA). The presence of free and protein-adducted NO2-FA in both mammalian and plant lipids further affirm a role for these species as signaling mediators. Since NO2-FA instigate adaptive anti-inflammatory gene expression and metabolic responses, these redox-derived metabolites may contribute to the cardiovascular benefits associated with the Mediterranean diet.
Highlights
Olive oil is the principal source of lipids in the Mediterranean diet, with ‘‘extra virgin’’ olive oil (EVOO) referring to an oil fraction produced via mechanical rather than chemical extraction of olives at temperatures that limit effects on intrinsic properties of the oil [1,2]
Considering that plants in general, and fresh olives in particular, are abundant in readily-nitrated unsaturated fatty acids, the present study evaluated whether electrophilic fatty acid nitroalkene derivatives (NO2-FA) are a) endogenously present in olives, b) extractable into the Extra virgin olive oil (EVOO) fraction and c) generated after consumption of olive lipids by the acidic conditions of digestion
Endogenous nitro-conjugated linoleic acid (NO2-cLA) and cLA in olive oil NO2-FA content was determined by high performance liquid chromatography- electrospray ionization- tandem mass spectrometry (HPLC-MS/MS) analysis of the free fatty acid fraction of lipase-digested EVOO [33]
Summary
Olive oil is the principal source of lipids in the Mediterranean diet, with ‘‘extra virgin’’ olive oil (EVOO) referring to an oil fraction produced via mechanical rather than chemical extraction of olives at temperatures that limit effects on intrinsic properties of the oil [1,2]. The Mediterranean diet is linked with the consumption of fruits and vegetables that are rich in the inorganic anions nitrite (NO22) and nitrate (NO32) [9,10]. These species are metastable nitric oxide (NO) oxidation products in vivo. Considering that plants in general, and fresh olives in particular, are abundant in readily-nitrated unsaturated fatty acids, the present study evaluated whether electrophilic fatty acid nitroalkene derivatives (NO2-FA) are a) endogenously present in olives, b) extractable into the EVOO fraction and c) generated after consumption of olive lipids by the acidic conditions of digestion
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