Nitrooleic

Nitrooleic refers to nitrooleic acid (NOA), a nitrated fatty acid formed by the addition of a nitro group to the double bond of oleic acid. The compound contains a conjugated system that makes it an electrophilic species capable of reacting with nucleophilic centers in proteins and nucleic acids. NOA is naturally generated during oxidative stress in tissues when nitric oxide species interact with polyunsaturated fatty acids, and it has been isolated from various animal and plant sources.

The synthesis of NOA can be achieved chemically by nitrating oleic acid with nitric acid or through enzymatic pathways involving peroxidases and nitrating enzymes such as nitric-oxide synthase. The final product is typically a fatty acid with an alpha,beta-unsaturated nitro group, conferring both lipophilicity and reactivity. Common analytical techniques for NOA include liquid chromatography–mass spectrometry and NMR spectroscopy to confirm the position of the nitro group and the degree of saturation.

Biologically, nitrooleic acid functions as a signaling molecule. It covalently modifies cysteine residues on Keap1, leading to activation of the Nrf2 antioxidant pathway and providing cytoprotection. NOA also exhibits anti-inflammatory activities by modulating NF‑κB signaling and reducing the production of pro‑inflammatory cytokines. Because of these properties, nitrooleic acid has been investigated as a potential therapeutic agent in models of neuroinflammation, atherosclerosis, and metabolic disorders.

In addition to its role in physiology, nitrooleic compounds serve as tools in chemical biology to study electrophilic signaling. Researchers employ modified derivatives such as nitrooleoyl phosphatidylethanolamine to probe membrane dynamics and protein modification. The ongoing research continues to uncover the mechanisms by which nitrooleic acids influence cellular homeostasis and their potential for drug development.