Beyond Prostaglandins—Chemistry and Biology of Cyclic Oxygenated Metabolites Formed by Free‐Radical Pathways from Polyunsaturated Fatty Acids

Abstract

Polyunsaturated fatty acids (PUFAs) are important constituents in all organisms. They fulfil many functions, ranging from modulating the structure of membranes to acting as precursors of physiologically important molecules, such as the prostaglandins, which for a long time were the most prominent cyclic PUFA metabolites. However, since the beginning of the 1990s a large variety of cyclic metabolites have been discovered that form under autoxidative conditions in vivo to a much larger extent than do prostaglandins. These compounds--isoprostanes, neuroprostanes, phytoprostanes, and isofurans--proved subsequently to be ubiquitous in nature. They display a wide range of biological activities, and isoprostanes have become the currently most reliable indicators of oxidative stress in humans. In a relatively short time, the structural variety, properties, and applications of the autoxidatively formed cyclic PUFA derivatives have been uncovered.

Non enzymatic metabolites of polyunsaturated fatty acids: friend or foe

“…In this review we will focus on lipids and especially on radical induced peroxidation of PUFAs by ROS (Jahn et al, 2008). The hydroxide radical is able to abstract a hydrogen atom from a methylene group surrounded by the two-double bonds in PUFAs and thus to initiate the lipid peroxidation process.…”

“…The quantification processes were developed due to the availability of synthetic compounds provided by organic chemists who are able to produce large amount of pure compounds (Jahn et al, 2008 commercially available were studied and since then their biological roles were also uncovered . For example, Morrow et al (1990) showed that the 15-F 2t -IsoP injected in a rat kidney, in the peripheral vein or directly in the kidney, allowed the reduction of the blood pressure and the rate of filtration.…”

The Prostaglandin E2Type 4 Receptor Participates in the Response to Acute Oxidant Stress in Airway Epithelial Cells

“…Isoprostanes are generated when ROS react with the unsaturated bonds of polyunsaturated fatty acids in the cell membrane (Jahn et al, 2008). One example of such an isoprostane, 8-iso-PGE 2 , is capable of stimulating CFTR-mediated transepithelial anion secretion across Calu-3 cells (Cowley, 2003).…”

An Azido-Biotin Reagent for Use in the Isolation of Protein Adducts of Lipid-derived Electrophiles by Streptavidin Catch and Photorelease

“…Polyunsaturated lipids in biological membranes are particularly reactive targets for oxygen radicals (1)(2)(3). Lipid peroxidation, the chain reaction of peroxyl radicals that is a consequence of oxidative stress, is thought to be involved in human diseases such as cancer, atherosclerosis, and neurodegenerative disorders (4 -8).…”

“…Lipid peroxidation, the chain reaction of peroxyl radicals that is a consequence of oxidative stress, is thought to be involved in human diseases such as cancer, atherosclerosis, and neurodegenerative disorders (4 -8). A variety of electrophilic compounds are byproducts of lipid peroxidation, 4-hydroxynon-2-enal (HNE) 1 being a particularly toxic electrophile (9 -12) that forms mutagenic DNA adducts (13)(14)(15). HNE and other lipid-derived electrophiles also form protein modifications, and some of these adducts have been characterized on a limited number of proteins and peptides by mass spectrometry (MS) and in tissues by antibody-based methods (16).…”