By making research easy to access, and puts the academic needs of the researchers before the business interests of publishers. Ferroptosis can be induced by lipid peroxidation in various subcellular The exceptions are the enzymatic dismutation of O2- (1010 M-1 s-1, catalyzed by the antioxidant enzyme superoxide dismutase, SOD), the first order reaction of decomposition of ONOO-, and the relatively lower rate (105 M-1 s-1) of the homolysis of H2O2 catalyzed by Fe2+ (Boveris et al., 2008). The biological effects of excess levels of the spectrum of these species are quite similar, and that is the reason they are collectively called reactive oxygen species (ROS). This pathway is triggered by the binding of death ligands of the tumor necrosis factor (TNF) family to their appropriate death receptors (DRs) on the cell surface; best-characterized ligands and corresponding death receptors include FasL/FasR and TNF-/TNFR1 [351, 352]. We conclude here that, first, mercury and methylmercury do not promote direct lipid peroxidation, but that, second, a simultaneous exposure to high inorganic mercury, copper, and iron and low selenium concentrations can lead to a condition in which mercury promotes lipid peroxidations. 5) (Repetto et al., 2010a). It is expected that supplementation with adequate antioxidants, as for instance, -tocopherol, will keep sensitive cells and organs in healthy conditions and increase lifespan. Valko M, Morris H, Cronin MTD. Since polyunsaturated fatty acids are more sensitive than saturated ones, it is obvious that the activated methylene (RH) bridge represents a critical target site. The abstraction of an allylic hydrogen of their structure produce another radical intermediate that after oxygenation step forms the corresponding dihydroperoxyde derivative (unstable), which after Hock rearrangement and cleavage produces 4-hydroperoxy-2E-nonenal (4S-HPNE), immediate precursor of HNE; and (v) the oxidation products generated after reaction of linoleate-derived hydroperoxy epoxide (13-Hp-Epo-Acid) with Fe+2 yields an alkolxyl radical, which undergo to di-epoxy-carbinyl radical and after beta-scission yield different aldehydes compounds including 4-HNE (Figure 5). The hydroxyl radical generated as a consequence of the Fenton reaction, oxidizes the cellular components of biological membranes (Fig. For example, 4-HNE promotes the formation of protein adducts that accumulate in the endoplasmic reticulum (ER) and led to autophagy in rat aortic smooth muscle cells, through selective activation of the PKR-like ER kinase (PERK) pathway accompanied by JNK activation, the upregulation of the HO-1, increased microtubule-associated protein 1 light chain 3 (LC3) formation, and maintenance of cell viability under conditions of excessive 4-HNE-protein adducts accumulation [303]. Tanito M, Agbaga M-P, Anderson RE. Anti-oxidative stress regulator NF-E2-related factor 2 mediates the adaptive induction of antioxidant and detoxifying enzymes by lipid peroxidation metabolite 4-hydroxynonenal. Massey KA, Nicolaou A. Lipidomics of oxidized polyunsaturated fatty acids. In SK-N-BE human neuroblastoma cells, 4-HNE upregulated p53 family gene expression and p53 gene targets p21 and bax, and the consequent reduction in S-phase cells and the increased apoptotic cell proportion; 4-HNE also reduced cyclin D2 expression [332]. The acute toxicity of iron and copper: biomolecule oxidation and oxidative damage in rat liver. In kidney and heart, indeed, lipid peroxidation and oxidative damage preceded necrosis (Repetto et al., 2010b). 4-hydroxynonenal induces p53-mediated apoptosis in retinal pigment epithelial cells. Urinary prostaglandin F2. Major substrates for lipid peroxidation are polyunsaturated fatty acids (PUFAs) [31, 36, 37], which are a family of lipids with two or more double bounds, that can be classified in omega-3 (n-3) and omega-6 (n-6) fatty acids according to the location of the last double bond relative to the terminal methyl end of the molecule. and ROO.. 4-Hydroxynonenal inhibits telomerase activity and hTERT expression in human leukemic cell lines. Hong CO, Rhee CH, Won NH, Choi HD, Lee KW. Growth factors, cytokines, cellular stress, and many other stimuli activate AP-1 [244, 245]. Telomeres are considered a biological clock of the cell and are shortened by each cell division until a critical length is reached and dysfunction ensues. Lin MH, Yen JH, Weng CY, Wang L, Ha CL, Wu MJ. Wang G, Li H, Firoze Khan M. Differential oxidative modification of proteins in MRL+/+ and MRL/lpr mice: increased formation of lipid peroxidation-derived aldehyde-protein adducts may contribute to accelerated onset of autoimmune response. In conditions in which lipid peroxidation is continuously initiated it gives non-radical products destroying two radicals at a time. Elongation factor 2 diphthamide is critical for translation of two IRES-dependent protein targets, XIAP and FGF2, under oxidative stress conditions. In Initiation, prooxidants abstract the allylic hydrogen forming the carbon-centered lipid radical; the carbon radical tends to be stabilized by a molecular rearrangement to form a conjugated diene (step 1). On the existence of transition-metal, CH can be reduced to form an alkoxyl radical, which can attack adjacent fatty acid side-chains to produce lipid radical and cumyl alcohol. Kim J, Paik HD, Yoon YC, Park E. Whey protein inhibits iron overload-induced oxidative stress in rats. Singlet oxygen-mediated damage to proteins and its consequences. These participate in chain reaction initiation that in turn abstract hydrogen and perpetuate the chain reaction of lipid peroxidation. Wang X, Lei XG, Wang J. Malondialdehyde regulates glucose-stimulated insulin secretion in murine islets via TCF7L2-dependent Wnt signaling pathway. However, Co2+ and Ni2+ alone, do not induce lipid peroxidation. Choi J-H, Kim D-W, Yun N, et al. Reduced form of transition-metals (Mn) reacts trough the Fenton reaction with hydrogen peroxide (H2O2), leading to the generation of OH. Kanno T, Nakamura K, Ikai H, Kikuchi K, Sasaki K, Niwano Y. Recently it has been shown that a membrane associated protein called regulator of G-protein signaling 4 (RGS4) can be modified by 4-HNE. Simvastatin prevents oxygen and glucose deprivation/reoxygenation-induced death of cortical neurons by reducing the production and toxicity of 4-hydroxy-2E-nonenal. It has long been recognized that high levels of free radicals or reactive oxygen species (ROS) can inflict direct damage to lipids. The continued oxidation of fatty acid side-chains and released PUFAs, and the fragmentation of peroxides to produce aldehydes, eventually lead to loss of membrane integrity by alteration of its fluidity which finally triggers inactivation of membrane-bound proteins. Triglycerides (apolar), stored in various cells, but especially in adipose (fat) tissue, are usually the main form of energy storage in mammals [1, 2]. Lipid peroxidation is a chain reaction process characterized by repetitive hydrogen abstraction by HO. The main genes regulated by 4-HNE- induced Nrf2-ARE pathway are as follows: (i) HO-1, an antioxidant protein that catalyzes the degradation of heme to biliverdin, which is then degraded to bilirubin; both biliverdin and bilirubin have antioxidant properties [227]; 4-HNE can upregulate HO-1 [217, 220, 221, 228230]; (ii) thioredoxin (Trx) and thioredoxin reductase (TrxR); Trx is a small (13kDa) antioxidant ubiquitous protein with two redox-active cysteine residues (-Cys-Gly-Pro-Cys-) in its active center; oxidized Trx is reduced back to the active form of Trx by Trx reductase (TrxR) in the presence of NADPH [231]; 4-HNE can upregulate Trx/TrxR [220, 221, 232]; (iii) glutamate cystein ligase (GCL) is a major determinant enzyme in GSH synthesis [233, 234]. 4-Hydroxynonenal and regulation of cell cycle: effects on the pRb/E2F pathway. O2.-, superoxide radical; H2O2, hydrogen peroxide, HO , hydroxyl radical; NO, nitric oxide; ONOO., peroxinitrite; NO2, nitrogen dioxide; UQH2, ubiquinol; UQH , ubisemiquinone; R , alkyl radical; ROO , peroxyl radical; 1O2, singlet oxygen. Hurst JS, Slater TF, Lang J. This NO radical accounts for the properties of the called endothelial derived relaxing factor, is the endogenous stimulator of the soluble guanylate cyclase and is a potent vasodilator in vitro (Moncada et al., 1991). WebOf note, some highly active Treg cells still rely on glycolysis. In retinal pigment epithelial (RPE) cells, at lower concentrations 4-HNE triggered phosphorylation of epidermal growth factor receptor (EGFR) and activation of its downstream signaling components ERK1/2 and Akt; this led to protective mechanism against oxidative stress [288]. Forman HJ, Dickinson DA, Iles KE. Das SK, Vasudevan DM. However, the thiobarbituric acid reacting substances test (TBARS) is notoriously nonspecific which has led to substantial controversy over its use for quantification of MDA from in vivo samples. Biomarkers of oxidative stress study III. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Licensee IntechOpen. The predominant n-6 fatty acid is arachidonic acid (AA), which can be reduced (i) via enzymatic peroxidation to prostaglandins, leukotrienes, thromboxanes, and other cyclooxygenase, lipoxygenase or cytochrome P-450 derived products [4]; or (ii) via nonenzymatic peroxidation to MDA, 4-HNE, isoprostanes, and other lipid peroxidation end-products (more stables and toxic than hydroperoxides) through oxygen radical-dependent oxidative routes [49, 71]. The normal plasma levels of TBARS are 2-3 M (Junqueira et al., 2004). Lipid Peroxidation: Kinetics, Mechanisms, and Products. WebOf note, some highly active Treg cells still rely on glycolysis. The formation of peroxyl radicals leads to the production of organic hydroperoxides, which, in turn, can subtract hydrogen from another PUFA. About 32 aldehydes were identified as products of lipid peroxidation: a) saturated aldehydes (propanal, butanal, hexanal, octanal, being the decanal the most important); b) 2,3-trans-unsaturated-aldehydes (hexenal, octenal, nonenal, decenal and undecenal); c) a series of 4-hydroxylated,2,3-trans-unsaturated aldehydes: 4-hydroxyundecenal, being 4-hydroxinonenal (HNE) the most important quantitatively. Tert-butyl hydroperoxide initiated chemiluminescence is an example of sensitized chemiluminescence, and it has been used to enhance the chemiluminescence accompanying lipid peroxidation and the -tocopherol content of tissues. Braithwaite EK, Mattie MD, Freedman JH. Cristalli DO, Arnal N, Marra FA, De Alaniz MJT, Marra CA. Sharma R, Sharma A, Chaudhary P, et al. Franklin JL. Singlet-oxygen-mediated amino acid and protein oxidation: formation of tryptophan peroxides and decomposition products. DNA-repair pathways are then recruited and cells enter senescence, losing their capacity to proliferate. sharing sensitive information, make sure youre on a federal The preference for amino acid modification by 4-HNE is Cys His > Lys resulting in covalent adducts with the protein nucleophilic side chain [104, 131, 360, 361]. 4-HNE can induce apoptosis through the death receptor Fas (CD95-)mediated extrinsic pathway as well as through the p53-dependent intrinsic pathway. Maggiora M, Rossi MA. At moderate concentration, when the basal level of antioxidant enzymes cannot be sufficient to neutralize 4-HNE, cells can survive due to 4-HNE may regulate several transcription factors sensible to stress such as nuclear factor erythroid 2-related factor 2 (Nrf2), activating protein-1 (AP-1), NF-B, and peroxisome-proliferator-activated receptors (PPAR). However, this conclusion is limited in practice by several important consideration: a) MDA yield as a result of lipid peroxidation varies with the nature of the PUFA peroxidised (specially its degree of instauration) and the peroxidation stimulus, b) only certain lipid oxidation products decompose yield MDA, c) MDA is only one of several end product of fatty peroxide formation and decomposition, d) the peroxidation environment influences both the formation of lipid-derived precursors and their decomposition to MDA, e) MDA itself is a reactive substance which can be oxidative and metabolically degraded, f) oxidative injury to no lipid biomolecules has the potential to generate MDA. Shaulian E, Karin M. AP-1 as a regulator of cell life and death. Alcohol-induced oxidative stress. Human biochemistry of the isoprostane pathway. Lee R, Margaritis M, Channon KM, Antoniades C. Evaluating oxidative stress in human cardiovascular disease: methodological aspects and considerations. Oxidized lipids activate autophagy in a JNK-dependent manner by stimulating the endoplasmic reticulum stress response. Vlkel W, Alvarez-Snchez R, Weick I, Mally A, Dekant W, Phler A. Glutathione conjugates of 4-hydroxy-2(E)-nonenal as biomarkers of hepatic oxidative stress-induced lipid peroxidation in rats. This assay is useful to evaluate the integral level of the non-enzymatic antioxidant defenses of a tissue (Gonzalez-Flecha et al., 1991a, 1993). 4-hydroxynonenal induces mitochondrial-mediated apoptosis and oxidative stress in SH-SY5Y human neuronal cells. Books > Since polyunsaturated fatty acids are more sensitive than saturated ones, it is obvious that the activated methylene (RH) bridge represents a critical target site. Kim T, Yang Q. Peroxisome-proliferator-activated receptors regulate redox signaling in the cardiovascular system. Sanyal J, Bandyopadhyay SK, Banerjee TK, et al. Contrary to radicals that attack biomolecules located less than a few nanometres from its site of generation [22], the lipid peroxidation-derived aldehydes can easily diffuse across membranes and can covalently modify any protein in the cytoplasm and nucleus, far from their site of origin [72]. Quantitative evaluation showed that the majority of senescent hepatocytes (as measured by -H2A.X) were also positive for 4-HNE [310, 311]. Possible mutagens derived from lipids and lipid precursors. Rodrguez-Martnez E, Camacho A, Maldonado PD, et al. By disrupting the Gsta4 gene that encodes the alpha class glutathione s-transferase (GST) isozyme GSTA4-4 in mice showed that GSTA4-4 plays a major role in protecting cells from the toxic effects of oxidant chemicals by attenuating the accumulation of 4-HNE [214]. a heterogeneous group of organic compounds that are insoluble in water and soluble in non-polar organic solvents. The Fenton reaction occurs in vivo at a very low rate, and hence cannot account for any substantial production of OH. Evaluation of hepatotoxicity and oxidative stress in rats treated with tert-butyl hydroperoxide. Lipid Peroxidation A form of oxidation that influences lipids. Conceptually, these two facts indicate that MDA is an excellent index of lipid peroxidation. (Step 2). Membrane damage can lead to release of heme compounds from erythrocytes. Complement factor H binds malondialdehyde epitopes and protects from oxidative stress. ), nitric oxide (NO), peroxinitrite (ONOO-) and singlet oxygen (1O2). As a result of lipid peroxidation a great variety of aldehydes can be produced, including hexanal, malondialdehyde (MDA) and 4-hydroxynonenal (Catala, 2006). 4-hydroxy-2-nonenal mediates genotoxicity and bystander effects caused by enterococcus faecalis-infected macrophages. 4-HNE also enhances MMP-2 production in VSMC via mitochondrial ROS-mediated activation of the Akt/NF-kappaB signaling pathways [254]. 17 to 20): In pathological situations, macrophages and neutrophils, recruited to a site of injury, are activated to produce NO as part of the inflammatory response. Tang EHC, Libby P, Vanhoutte PM, Xu A. Anti-inflammation therapy by activation of prostaglandin EP4 receptor in cardiovascular and other inflammatory diseases. Balogh and Atkins described the cellular effects of 4-HNE, followed by a review of its GST-catalyzed detoxification, with an emphasis on the structural attributes that play an important role in the interactions with alpha-class GSTs. 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