Detection of lipid peroxidation products in lipids and tissues by gas chromatography-mass spectrometry.
TL;DR: The formation of oxygen radicals and lipid peroxidation have been suggested to play a key role in various types of tissue degeneration and pathology such as heart disease, aging, cancer, and retinal degeneration.
Abstract: Formation of oxygen radicals and lipid peroxidation have been suggested to play a key role in various types of tissue degeneration and pathology such as heart disease, aging, cancer, and retinal degeneration1,2 Membrane phospholipids and triglycerides contain the principal deposits of unsaturated fatty acids and are thought to be the primary sites of the lipid peroxidation process The oxidation of membrane phospholipids has been hypothesized to cause an increase in the permeability of cell membranes and/or to inhibit membrane ion pumps and to lead to cell death This loss of membrane barrier function is thought to lead to edema, disturbances in electrolyte balance, and elevation of intracellular calcium which contributes to the malfunctioning of cells
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TL;DR: In this article, the authors compared the mass spectra of different derivatives of LPO aldehydes for GC separation in order to demonstrate which ones are most useful to obtain maximum information on the structure of the original aldehyde.
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TL;DR: The concentrations of HNE produced in tissues taken from animals depleted of α-tocopherol were found to be up to 8 times higher than those take from animals supplemented with α-ocopherol.
Abstract: A method is presented for the determination of 4-hydroxy-nonenal (HNE) in tissue homogenates followingin vitro lipid peroxidation induced by iron (Fe++). NHE is measured as the pentafluorobenzyl oxime derivative using liquid chromatography thermospray mass spectrometry.In vitro metabolism of HNEvia the glutathione/glutathione-S-transferase pathway was inhibited using iodoacetic and iodobenzoic acids. The assay has been used as an indicator of the peroxidizability of tissue samples from animals both adequate in and depleted of α-tocopherol. The concentrations of HNE produced in tissues taken from animals depleted of α-tocopherol were found to be up to 8 times higher than those taken from animals supplemented with α-tocopherol.
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TL;DR: Malonaldehyde is of interest primarily as a product of lipid peroxidation in vivo and as an index of oxidative rancidity in foods and reacts with a variety of compounds to form derivatives, which can be estimated spectrophotometricaily.
Abstract: Publisher Summary Malonaldehyde (MA) is of interest primarily as a product of lipid peroxidation in vivo and as an index of oxidative rancidity in foods. In biological materials, it exists in its free form and as a complex with various tissue constituents. It reacts with a variety of compounds to form derivatives, which can be estimated spectrophotometricaily. It has also been identified among the products of the oxidative decomposition of amino acids, complex carbohydrates, pentoses, and hexoses formed in the presence of a metal catalyst, as a product of free radicals generated by ionizing radiation in vivo, and as a byproduct of prostaglandin biosynthesis. However, peroxidation of fatty acids with three or more double bonds (notably arachidonic acid) is believed to be its major source. Because of its interest as an indicator of lipid peroxidation, various methods have been proposed for its estimation. The most widely employed method for the determination of MA in biological materials is based on its reaction with thiobarbituric acid (TBA).
540 citations
TL;DR: In this paper, an acid-acetalation decomposition procedure was used to evaluate lipid oxidation products as sources of malonaldehyde and its biological effects due to crosslinking.
Abstract: This paper reviews our studies of fatty acid hydroperoxides, their secondary products and mechanisms for their formation in the context of some of their possible biological consequences. The uneven distribution of isomeric hydroperoxides in oxidized linolenate and photosensitized oxidized linoleate is related to the formation of hydroperoxy cyclic peroxides. Interest in the hydroperoxy mono-and bi-cycloendoperoxides from oxidized linolenate stems from their structural relationship to the prostaglandins. However, the biological activity of hydroperoxy cyclic peroxides formed by autoxidation has not yet been reported. Thermal decomposition studies of secondary lipid oxidation products show they are important precursors of volatile compounds. An acid-acetalation decomposition procedure establishes that 5-membered hydroperoxy cyclic peroxides and 1,3-dihydroperoxides are important precursors of malonaldehyde. This approach provides a more specific test than the thiobarbituric acid (TBA) color reaction to evaluate lipid oxidation products as sources of malonaldehyde and its biological effects due to crosslinking. A better understanding is needed of the biological effects of a multitude of lipid oxidation decomposition products other than malonaldehyde.
489 citations
TL;DR: Ultraviolet spectrophometric detection of conjugated dienes has been used for many years in the food industry for the detection of autoxidized lipids and for a variety of pathological processes, the question has been raised whether peroxidative decomposition of membrane lipids has occurred in vivo.
Abstract: Publisher Summary Like many other substances, naturally occurring lipids exhibit simple end absorption in ultraviolet light as the wavelength is lowered toward 200 nm. The spectra of a variety of organic molecules containing conjugated dienes, however, are characterized by intense absorption, the so-called K band, which may range, with respect to peak absorption, from 215 to 250 nm, depending on nearby substituent groups. Ultraviolet spectrophometric detection of conjugated dienes has been used for many years in the food industry for the detection of autoxidized lipids. The method appears to have been applied for the first time to the problem of liver cell lipid peroxidation of toxigenic origin in 1966 and has been widely used since. For a variety of pathological processes, the question has been raised whether peroxidative decomposition of membrane lipids has occurred in vivo. A second principle of the method recognizes that for whole-animal studies involving possible lipid peroxidation, the fraction of endogenous lipids actually peroxidized may not only be low, but the process of lipid peroxidation may be confined to a particular subcellular structure.
454 citations
TL;DR: This chapter discusses the methods used for studying lipid peroxidation and concentrates on such aspects of lipidperoxidation in relation to biomembrane disturbance.
Abstract: Publisher Summary Lipid peroxidation is a complex process whereby unsaturated lipid material undergoes reaction with molecular oxygen to yield lipid hydroperoxides; in most situations involving biological samples, the lipid hydroperoxides are degraded to a variety of products, including aikanals, alkenals, hydroxyalkenals, ketones, and alkanes. Although attack by singlet oxygen on unsaturated lipid has been shown to give lipid hydroperoxide by a nonradical, nonchain process, the vast majority of situations involving lipid peroxidation proceed through a free radical-mediated chain reaction initiated by the abstraction of a hydrogen atom from the unsaturated lipid by a reactive free radical, followed by a complex sequence of propagative reactions. The peroxidation of polyunsaturated fatty acids (PUFAs) can proceed through nonenzymic autoxidative pathways or through processes that are enzymically catalyzed. The importance of autoxidation in the deterioration of foods, and in the oil industry, has long been recognized, and authoritative reviews are available for such aspects. A relatively new growth point for studies on lipid peroxidation has been the realization that many toxic agents can be metabolically activated within cells to free-radical intermediates that can initiate lipid peroxidation and result in cell injury. A very large number of such studies on lipid peroxidation in biological systems have demonstrated the degradation of membrane PUFAs, with a subsequent disorganization of membrane structure and disturbance of membrane function. This chapter discusses the methods used for studying lipid peroxidation concentrates on such aspects of lipid peroxidation in relation to biomembrane disturbance.
440 citations
395 citations