Lipidomics of essential fatty acids and oxygenated metabolites

Lagarde, Michel; Calzada, Catherine; Véricel, Evelyne; Guichardant, Michel

doi:10.1002/mnfr.201200828

Cited by 24 publications

(24 citation statements)

References 114 publications

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“…COX converts DGLA to series 1 prostaglandins (PGD 1 , PGE 1 ) and TXA 1 [23, 24], which inhibit platelet function in vitro and in vivo [25]. These DGLA-derived COX prostanoids exerted their anti-platelet action by activating the Gα s -coupled GPCRs, prostaglandin (EP 2 and EP 4 ) or IP receptors.…”

Section: Cox-derived Metabolites and Their Regulatory Roles On Platelmentioning

confidence: 99%

The expansive role of oxylipins on platelet biology

2017

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In mammals, three major oxygenases, cyclooxygenases (COXs), lipoxygenases (LOXs), and cyto-chrome P450 (CYP450), generate an assortment of unique lipid mediators (oxylipins) from polyunsaturated fatty acids (PUFAs) which exhibit pro- or anti-thrombotic activity. Over the years, novel oxylipins generated from the interplay of theoxygenase activity in various cells, such as the specialized pro-resolving mediators (SPMs), have been identified and investigated in inflammatory disease models. Although platelets have been implicated in inflammation, the role and mechanism of these SPMs produced from immune cells on platelet function are still unclear. This review highlights the burgeoning classes of oxylipins that have been found to regulate platelet function; however, their mechanism of action still remains to be elucidated.

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Section: Cox-derived Metabolites and Their Regulatory Roles On Platelmentioning

confidence: 99%

The expansive role of oxylipins on platelet biology

2017

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“…The linoleic acid metabolism pathway is responsible for the production of two main oxylipin precursors, DGLA and AA (Lagarde et al, 2013). The first step in this pathway is the addition of a double bond to LA by Δ 6 desaturase which produces gamma-linolenic acid (GLA, 18:3).…”

Section: Oxylipin Biologymentioning

confidence: 99%

“…An elongase then facilitates the addition of two-carbons to GLA forming DGLA (20:3). DGLA is a substrate for oxygenases but can be further converted to AA (20:4), the most abundant oxylipin precursor, through the addition of a double bond by Δ 5 desaturase (Lagarde et al, 2013). The activity of Δ 5 desaturase in human platelets, monocytes and neutrophils is limited; therefore supplementation with either GLA or DGLA does not increase AA levels in these cells (de Bravo et al, 1985; Pullman-Mooar et al, 1990; Barre and Holub, 1992; Chilton et al, 1996).…”

Section: Oxylipin Biologymentioning

confidence: 99%

The emerging role of oxylipins in thrombosis and diabetes

2014

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The prevalence of cardiovascular disease (CVD), the leading cause of death in the US, is predicted to increase due to the shift in age of the general population and increase in CVD risk factors such as obesity and diabetes. New therapies are required to decrease the prevalence of CVD risk factors (obesity and diabetes) as well as reduce atherothrombosis, the major cause of CVD related mortality. Oxylipins, bioactive metabolites derived from the oxygenation of polyunsaturated fatty acids, play a role in the progression of CVD risk factors and thrombosis. Aspirin, a cyclooxygenase-1 inhibitor, decreases atherothrombotic associated mortality by 25%. These potent effects of aspirin have shown the utility of modulating oxylipin signaling pathways to decrease CVD mortality. The role of many oxylipins in the progression of CVD, however, is still uncertain or controversial. An increased understanding of the role oxylipins play in CVD risk factors and thrombosis could lead to new therapies to decrease the prevalence of CVD and its associated mortality.

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“…At the time, the relevance of lipid peroxidation to biological systems was not realized, but subsequently it was discovered that production of important lipid signalling mediators of the isoprostane family, such as prostaglandins and thromboxanes, involved enzymatically catalysed radical processes to peroxidize arachidonic acid [5,6]. This area of research has expanded hugely, as other PUFAs yield analogous products with a plethora of biological activities.…”

Section: Introductionmentioning

confidence: 99%

Chemistry and analysis of HNE and other prominent carbonyl-containing lipid oxidation compounds

Sousa

Pitt

Spickett

2017

Free Radical Biology and Medicine

145

105

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The process of lipid oxidation generates a diverse array of small aldehydes and carbonyl-containing compounds, which may occur in free form or esterified within phospholipids and cholesterol esters. These aldehydes mostly result from fragmentation of fatty acyl chains following radical oxidation, and the products can be subdivided into alkanals, alkenals (usually D,β-unsaturated), γ-substituted alkenals and bis-aldehydes.Isolevuglandins are non-fragmented di-carbonyl compounds derived from H 2 -isoprostanes, and oxidation of the ω-3-fatty acid docosahexenoic acid yield analogous 22 carbon neuroketals. Non-radical oxidation by hypochlorous acid can generate D-chlorofatty aldehydes from plasmenyl phospholipids. Most of these compounds are reactive and have generally been considered as toxic products of a deleterious process. The reactivity is especially high for the D,β-unsaturated alkenals, such as acrolein and crotonaldehyde, and for γ-substituted alkenals, of which 4-hydroxy-2-nonenal and 4-oxo-2-nonenal are best Page | 2 known. Nevertheless, in recent years several previously neglected aldehydes have been investigated and also found to have significant reactivity and biological effects; notable examples are 4-hydroxy-2-hexenal and 4-hydroxy-dodecadienal. This has led to substantial interest in the biological effects of all of these lipid oxidation products and their roles in disease, including proposals that HNE is a second messenger or signalling molecule.However, it is becoming clear that many of the effects elicited by these compounds relate to their propensity for forming adducts with nucleophilic groups on proteins, DNA and specific phospholipids. This emphasizes the need for good analytical methods, not just for free lipid oxidation products but also for the resulting adducts with biomolecules. The most informative methods are those utilizing HPLC separations and mass spectrometry, although analysis of the wide variety of possible adducts is very challenging. Nevertheless, evidence for the occurrence of lipid-derived aldehyde adducts in biological and clinical samples is building, and offers an exciting area of future research. AbbreviationsAcr-dG, 1,N2-propanodeoxyguanosine; AGEs, advanced glycation end-product; ALEs, advanced lipoxidation end product; ApoB100, apolipoprotein B100; ApoE, apolipoprotein E; ARP, aldehyde reactive probe; AspN, endoproteinase AspN (flavastacin); βLG, β-lactoglobulin; BHZ, biotin hydrazide; BN-PAGE, blue native polyacrylamide gel

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Lipidomics of essential fatty acids and oxygenated metabolites

Cited by 24 publications

References 114 publications

The expansive role of oxylipins on platelet biology

The expansive role of oxylipins on platelet biology

The emerging role of oxylipins in thrombosis and diabetes

Chemistry and analysis of HNE and other prominent carbonyl-containing lipid oxidation compounds

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