Literature DB >> 27713004

Biological and pathophysiological roles of end-products of DHA oxidation.

Valentin P Yakubenko1, Tatiana V Byzova2.   

Abstract

BACKGROUND: Polyunsaturated fatty acids (PUFA) are known to be present and/or enriched in vegetable and fish oils. Among fatty acids, n-3 PUFA are generally considered to be protective in inflammation-related diseases. The guidelines for substituting saturated fatty acids for PUFAs have been highly publicized for decades by numerous health organizations. Recently, however, the beneficial properties of n-3 PUFA are questioned by detailed analyses of multiple randomized controlled clinical trials. The reported heterogeneity of results is likely due not only to differential effects of PUFAs on various pathological processes in humans, but also to the wide spectrum of PUFA's derived products generated in vivo. SCOPE OF REVIEW: The goal of this review is to discuss the studies focused on well-defined end-products of PUFAs oxidation, their generation, presence in various pathological and physiological conditions, their biological activities and known receptors. Carboxyethylpyrrole (CEP), a DHA-derived oxidized product, is especially emphasized due to recent data demonstrating its pathophysiological significance in many inflammation-associated diseases, including atherosclerosis, hyperlipidemia, thrombosis, macular degeneration, and tumor progression. MAJOR
CONCLUSIONS: CEP is a product of radical-based oxidation of PUFA that forms adducts with proteins and lipids in blood and tissues, generating new powerful ligands for TLRs and scavenger receptors. The interaction of CEP with these receptors affects inflammatory response, angiogenesis, and wound healing. GENERAL SIGNIFICANCE: The detailed understanding of CEP-mediated cellular responses may provide a basis for the development of novel therapeutic strategies and dietary recommendations.
Copyright © 2016 Elsevier B.V. All rights reserved.

Entities:  

Keywords:  CD36; Carboxyethylpyrrole; Docosahexaenoic acid; Inflammation; Polyunsaturated fatty acids; Toll-like receptors

Mesh:

Substances:

Year:  2016        PMID: 27713004      PMCID: PMC5360178          DOI: 10.1016/j.bbalip.2016.09.022

Source DB:  PubMed          Journal:  Biochim Biophys Acta Mol Cell Biol Lipids        ISSN: 1388-1981            Impact factor:   4.698


  71 in total

1.  High-performance liquid chromatography/thermospray mass spectrometry of eicosanoids and novel oxygenated metabolites of docosahexaenoic acid.

Authors:  J A Yergey; H Y Kim; N Salem
Journal:  Anal Chem       Date:  1986-06       Impact factor: 6.986

2.  Stereochemical assignment and anti-inflammatory properties of the omega-3 lipid mediator resolvin E3.

Authors:  Yosuke Isobe; Makoto Arita; Ryo Iwamoto; Daisuke Urabe; Hidenori Todoroki; Koji Masuda; Masayuki Inoue; Hiroyuki Arai
Journal:  J Biochem       Date:  2013-01-03       Impact factor: 3.387

3.  TLR4, rather than TLR2, regulates wound healing through TGF-β and CCL5 expression.

Authors:  Hiraku Suga; Makoto Sugaya; Hideki Fujita; Yoshihide Asano; Yayoi Tada; Takafumi Kadono; Shinichi Sato
Journal:  J Dermatol Sci       Date:  2013-10-31       Impact factor: 4.563

4.  (Carboxyalkyl)pyrroles in human plasma and oxidized low-density lipoproteins.

Authors:  K Kaur; R G Salomon; J O'Neil; H F Hoff
Journal:  Chem Res Toxicol       Date:  1997-12       Impact factor: 3.739

5.  Fatty acid oxidation products in human atherosclerotic plaque: an analysis of clinical and histopathological correlates.

Authors:  Emma I Waddington; Kevin D Croft; Kishore Sienuarine; Bruce Latham; Ian B Puddey
Journal:  Atherosclerosis       Date:  2003-03       Impact factor: 5.162

6.  Oxidatively truncated docosahexaenoate phospholipids: total synthesis, generation, and Peptide adduction chemistry.

Authors:  Xiaorong Gu; Mingjiang Sun; Bogdan Gugiu; Stanley Hazen; John W Crabb; Robert G Salomon
Journal:  J Org Chem       Date:  2003-05-16       Impact factor: 4.354

7.  Engagement of platelet toll-like receptor 9 by novel endogenous ligands promotes platelet hyperreactivity and thrombosis.

Authors:  Soumya Panigrahi; Yi Ma; Li Hong; Detao Gao; Xiaoxia Z West; Robert G Salomon; Tatiana V Byzova; Eugene A Podrez
Journal:  Circ Res       Date:  2012-10-15       Impact factor: 17.367

Review 8.  Docosahexaenoic acid uptake and metabolism in photoreceptors: retinal conservation by an efficient retinal pigment epithelial cell-mediated recycling process.

Authors:  N G Bazan; W C Gordon; E B Rodriguez de Turco
Journal:  Adv Exp Med Biol       Date:  1992       Impact factor: 2.622

9.  Age-related macular degeneration.

Authors:  Hanna R Coleman; Chi-Chao Chan; Frederick L Ferris; Emily Y Chew
Journal:  Lancet       Date:  2008-11-22       Impact factor: 79.321

10.  Lack of involvement of CEP adducts in TLR activation and in angiogenesis.

Authors:  John Gounarides; Jennifer S Cobb; Jing Zhou; Frank Cook; Xuemei Yang; Hong Yin; Erik Meredith; Chang Rao; Qian Huang; YongYao Xu; Karen Anderson; Andrea De Erkenez; Sha-Mei Liao; Maura Crowley; Natasha Buchanan; Stephen Poor; Yubin Qiu; Elizabeth Fassbender; Siyuan Shen; Amber Woolfenden; Amy Jensen; Rosemarie Cepeda; Bijan Etemad-Gilbertson; Shelby Giza; Muneto Mogi; Bruce Jaffee; Sassan Azarian
Journal:  PLoS One       Date:  2014-10-24       Impact factor: 3.240

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  7 in total

1.  Lipid-derived and other oxidative modifications of retinal proteins in a rat model of Smith-Lemli-Opitz syndrome.

Authors:  Rebecca J Kapphahn; Michael J Richards; Deborah A Ferrington; Steven J Fliesler
Journal:  Exp Eye Res       Date:  2018-08-14       Impact factor: 3.467

Review 2.  Context-Dependent Role of Oxidized Lipids and Lipoproteins in Inflammation.

Authors:  Yury I Miller; John Y-J Shyy
Journal:  Trends Endocrinol Metab       Date:  2016-12-05       Impact factor: 12.015

3.  Modification of Extracellular Matrix by the Product of DHA Oxidation Switches Macrophage Adhesion Patterns and Promotes Retention of Macrophages During Chronic Inflammation.

Authors:  Jared L Casteel; Kasey R Keever; Christopher L Ardell; David L Williams; Detao Gao; Eugene A Podrez; Tatiana V Byzova; Valentin P Yakubenko
Journal:  Front Immunol       Date:  2022-05-26       Impact factor: 8.786

4.  Inflammation-dependent oxidative stress metabolites as a hallmark of amyotrophic lateral sclerosis.

Authors:  Luyang Xiong; Michael McCoy; Hitoshi Komuro; Xiaoxia Z West; Valentin Yakubenko; Detao Gao; Tejasvi Dudiki; Amanda Milo; Jacqueline Chen; Eugene A Podrez; Bruce Trapp; Tatiana V Byzova
Journal:  Free Radic Biol Med       Date:  2021-12-03       Impact factor: 8.101

Review 5.  Understanding AMD by analogy: systematic review of lipid-related common pathogenic mechanisms in AMD, AD, AS and GN.

Authors:  Qinyuan Xu; Sijia Cao; Sanjeeva Rajapakse; Joanne A Matsubara
Journal:  Lipids Health Dis       Date:  2018-01-04       Impact factor: 3.876

6.  Ossified blood vessels in primary familial brain calcification elicit a neurotoxic astrocyte response.

Authors:  Yvette Zarb; Ulrike Weber-Stadlbauer; Daniel Kirschenbaum; Diana Rita Kindler; Juliet Richetto; Daniel Keller; Rosa Rademakers; Dennis W Dickson; Andreas Pasch; Tatiana Byzova; Khayrun Nahar; Fabian F Voigt; Fritjof Helmchen; Andreas Boss; Adriano Aguzzi; Jan Klohs; Annika Keller
Journal:  Brain       Date:  2019-04-01       Impact factor: 13.501

7.  Lateral heterogeneity and domain formation in cellular membranes.

Authors:  Jacob J Kinnun; Dima Bolmatov; Maxim O Lavrentovich; John Katsaras
Journal:  Chem Phys Lipids       Date:  2020-09-15       Impact factor: 3.329

  7 in total

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