Abstract
Nitro-fatty acids are formed and detected in human plasma, cell membranes, and tissue, modulating metabolic as well as inflammatory signaling pathways. Here we discuss the mechanisms of nitro-fatty acid formation as well as their key chemical and biochemical properties. The electrophilic properties of nitro-fatty acids to activate anti-inflammatory signaling pathways are discussed in detail. A critical issue is the influence of nitroarachidonic acid on prostaglandin endoperoxide H synthases, redirecting arachidonic acid metabolism and signaling. We also analyze in vivo data supporting nitro-fatty acids as promising pharmacological tools to prevent inflammatory diseases.
Highlights
Nitric oxide (NNO)-derived species (NOx) react with unsaturated fatty acids to yield a variety of oxidized and nitrated products [1]
Peroxynitrite anion (ONOO–) and peroxynitrous acid (ONOOH) are potent one- and two-electron oxidants that can react with unsaturated fatty acids [4]
The formation of cholesteryl nitrolinoleate (NO2-cholesteryl linoleate (CL)) by activated macrophages is prevented by nitric oxide synthase (NOS) inhibitors, supporting the contribution of NNOderived species toward CL nitration
Summary
Nitric oxide (NNO)-derived species (NOx) react with unsaturated fatty acids to yield a variety of oxidized and nitrated products [1]. The mechanisms of fatty acid nitration in vivo remain unknown, with suggested pathways including reactions of unsaturated fatty acids with secondary products of NNO oxidation such as nitrogen dioxide (NNO2), nitrite (NO2–), and peroxynitrite (ONOO–; Figure 1). NO2-AA exerts a protective anti-inflammatory action, diminishing NOS-2 expression and secretion of proinflammatory cytokines [18].
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