Olives and olive oil are sources of electrophilic fatty acid nitroalkenes.
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.
Department of Pharmacology and Chemical Biology, University of Pittsburgh School of Medicine, Pittsburgh, Pennsylvania, United States of America ; Fondazione Ri.MED, Palermo, Italy.
Marco
M
Fazzari
Departamento de Bioquímica and Center for Free Radical and Biomedical Research, Facultad de Medicina, Universidad de la República, Montevideo, Uruguay.
Andrés
A
Trostchansky
Department of Pharmacology and Chemical Biology, University of Pittsburgh School of Medicine, Pittsburgh, Pennsylvania, United States of America.
Francisco J
FJ
Schopfer
Department of Pharmacology and Chemical Biology, University of Pittsburgh School of Medicine, Pittsburgh, Pennsylvania, United States of America.
Sonia R
SR
Salvatore
Departamento de Biología Experimental, Universidad de Jaén, Jaén, Andalucía, Spain.
Beatriz
B
Sánchez-Calvo
Department of Pharmacology and Chemical Biology, University of Pittsburgh School of Medicine, Pittsburgh, Pennsylvania, United States of America.
Dario
D
Vitturi
Departamento de Biología Experimental, Universidad de Jaén, Jaén, Andalucía, Spain.
Raquel
R
Valderrama
Departamento de Biología Experimental, Universidad de Jaén, Jaén, Andalucía, Spain.
Juan B
JB
Barroso
Departamento de Bioquímica and Center for Free Radical and Biomedical Research, Facultad de Medicina, Universidad de la República, Montevideo, Uruguay.
Rafael
R
Radi
Department of Pharmacology and Chemical Biology, University of Pittsburgh School of Medicine, Pittsburgh, Pennsylvania, United States of America.
Bruce A
BA
Freeman
Departamento de Bioquímica and Center for Free Radical and Biomedical Research, Facultad de Medicina, Universidad de la República, Montevideo, Uruguay.
Homero
H
Rubbo
D000475:Alkenes / Q000737:chemistry*; D000893:Anti-Inflammatory Agents / Q000032:analysis / Q000737:chemistry; D032701:Biomimetics; D004041:Dietary Fats / Q000032:analysis; D004063:Digestion; D004583:Electrons; D005227:Fatty Acids / Q000032:analysis* / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D009574:Nitro Compounds / Q000737:chemistry*; D031658:Olea / Q000737:chemistry*; D000069463:Olive Oil; D010938:Plant Oils / Q000737:chemistry*; D010940:Plant Proteins / Q000737:chemistry; D013270:Stomach / Q000737:chemistry / Q000502:physiology
D000475:Alkenes; D000893:Anti-Inflammatory Agents; D004041:Dietary Fats; D005227:Fatty Acids; D009574:Nitro Compounds; D000069463:Olive Oil; D010938:Plant Oils; D010940:Plant Proteins