Characterization and biological effects of di-hydroxylated compounds deriving from the lipoxygenation of ALA

Liu, Miao; Chen, Ping; Véricel, Evelyne; Lelli, Moreno; Béguin, Laetitia; Lagarde, Michel; Guichardant, Michel

doi:10.1194/jlr.m035139

Cited by 45 publications

(36 citation statements)

References 50 publications

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“…These data confirm the role of ALOX12 in regulating platelet function and thrombosis and provide the basis for the development of innovative strategies for the therapy of thrombosis [270, 271]. Moreover, dihydroxylated metabolites derived from alpha-linoleic acid inhibit platelet function [272] and a geometric isomer of protectin D also prevented platelet aggregation at submicromolar concentrations when induced by either collagen, arachidonic acid or thromboxane [273]. …”

Section: Biological Function Of Mammalian Lox Isoformsmentioning

confidence: 54%

Mammalian lipoxygenases and their biological relevance

Kühn

Banthiya

Leyen

2015

Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biolog

502

431

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Lipoxygenases (LOXs) form a heterogeneous class of lipid peroxidizing enzymes, which have been implicated in cell proliferation and differentiation but also in the pathogenesis of various diseases with major public health relevance. As other fatty acid dioxygenases LOX oxidize polyunsaturated fatty acids to their corresponding hydroperoxy derivatives, which are further transformed to bioactive lipid mediators (eicosanoids and related substances). On the other hand, lipoxygenases are key players in regulation of the cellular redox homeostasis, which is an important element in gene expression regulation. Although the first mammalian lipoxygenases were discovered 40 years ago and although the enzymes have been well characterized with respect to their structural and functional properties the biological roles of the different lipoxygenase isoforms are not completely understood. This review is aimed at summarizing the current knowledge on the physiological roles of different mammalian LOX-isoforms and their patho-physiological function in inflammatory, metabolic, hyperproliferative, neurodegenerative and infectious disorders.

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Section: Biological Function Of Mammalian Lox Isoformsmentioning

confidence: 54%

Mammalian lipoxygenases and their biological relevance

Kühn

Banthiya

Leyen

2015

Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biolog

502

431

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“…18:3n-3 has not been described as a platelet dioxygenases substrate, although its position isomer 18:3n-6 (-linolenic acid) was historically used to suggest that human platelets have a lipoxygenase activity [41]. However, double lipoxygenation endproducts (via soybean 15-LOX) from 18:3n-3 have been described as inhibitors of platelet aggregation through COX inhibition [42], and named linotrins [43] as they belong to the poxytrin family based on the report of the same platelet inhibition by protectin DX, the double lipoxygenation end-product of DHA [44].…”

Section: Oxygenation Of Ara In Human Blood Plateletsmentioning

confidence: 99%

Oxygenation of polyunsaturated fatty acids and oxidative stress within blood platelets

Lagarde

Guichardant

Bernoud-Hubac

et al. 2018

Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biolog

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The oxygenation metabolism of arachidonic acid (ArA) has been early described in blood platelets, in particular with its conversion into the potent labile thromboxane A that induces platelet aggregation and vascular smooth muscle cells contraction. In addition, the primary prostaglandins D and E have been mainly reported as inhibitors of platelet function. The platelet 12-lipoxygenase (12-LOX) product, i.e. the hydroperoxide 12-HpETE, appears to stimulate platelet ArA metabolism at the level of its release from membrane phospholipids through phospholipase A (cPLA) and cyclooxygenase (COX-1) activities, the first enzymes in prostanoid production cascade. Also, 12-HpETE may regulate the oxygenation of other polyunsaturated fatty acids (PUFA) by platelets, especially that of eicosapentaenoic acid (EPA). On the other hand, the reduced product of 12-HpETE, 12-HETE, is able to antagonize TxA action. This is even more obvious for the 12-LOX end-products from docosahexaenoic acid (DHA), 11- and 14-HDoHE. In addition, 12-HpETE plays a key role in platelet oxidative stress as observed in pathophysiological conditions, but may be regulated by DHA with a bimodal way according to its concentration. Other oxygenated products of PUFA, especially omega-3 PUFA, produced outside platelets may affect platelet functions as well.

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“…Poxytrins inhibit blood platelet aggregation at the levels of COX-1 activity and the TxA 2 receptor [71]. More recent studies have shown that poxytrins may exhibit inhibitory effect of COX-2 and inflammation as well [88,89]. Finally, ALA may even be oxygenated into 12-HOTE through a COX-2 aborted cyclooxygenation process as stated above for 9-HODE [90].…”

Section: Oxygenation Of the Indispensable Precursorsmentioning

confidence: 99%

Lipidomics of essential fatty acids and oxygenated metabolites

Lagarde

Calzada

Véricel

et al. 2013

Molecular Nutrition Food Res

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Polyunsaturated fatty acids in mammals may be oxygenated into a myriad of bioactive products through di- and monooxygenases, products that are rapidly degraded to control their action. To evaluate the phenotypes of biological systems regarding this wide family of compounds, a lipidomics approach in function of time and compartments would be relevant. The current review takes into consideration most of the diverse oxygenated metabolites of essential fatty acids at large and their immediate degradation products. Their biological function and life span are considered. Overall, this is a fluxolipidomics approach that is emerging.

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Characterization and biological effects of di-hydroxylated compounds deriving from the lipoxygenation of ALA

Cited by 45 publications

References 50 publications

Mammalian lipoxygenases and their biological relevance

Mammalian lipoxygenases and their biological relevance

Oxygenation of polyunsaturated fatty acids and oxidative stress within blood platelets

Lipidomics of essential fatty acids and oxygenated metabolites

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