Literature DB >> 32827665

Cytochrome P450-derived linoleic acid metabolites EpOMEs and DiHOMEs: a review of recent studies.

Kelsey Hildreth1, Sean D Kodani2, Bruce D Hammock2, Ling Zhao3.   

Abstract

Linoleic acid (LA) is the most abundant polyunsaturated fatty acid found in the Western diet. Cytochrome P450-derived LA metabolites 9,10-epoxyoctadecenoic acid (9,10-EpOME), 12,13-epoxyoctadecenoic acid (12,13-EpOME), 9,10-dihydroxy-12Z-octadecenoic acid (9,10-DiHOME) and 12,13-dihydroxy-9Z-octadecenoic acid (12,13-DiHOME) have been studied for their association with various disease states and biological functions. Previous studies of the EpOMEs and DiHOMEs have focused on their roles in cytotoxic processes, primarily in the inhibition of the neutrophil respiratory burst. More recent research has suggested the DiHOMEs may be important lipid mediators in pain perception, altered immune response and brown adipose tissue activation by cold and exercise. The purpose of this review is to summarize the current understanding of the physiological and pathophysiological roles and modes of action of the EpOMEs and DiHOMEs in health and disease.
Copyright © 2020 Elsevier Inc. All rights reserved.

Entities:  

Keywords:  12,13-DiHOME; Cytochrome P450; Isoleukotoxin; Leukotoxin; Linoleic acid; Soluble epoxide hydrolase

Mesh:

Substances:

Year:  2020        PMID: 32827665      PMCID: PMC7606796          DOI: 10.1016/j.jnutbio.2020.108484

Source DB:  PubMed          Journal:  J Nutr Biochem        ISSN: 0955-2863            Impact factor:   6.048


  99 in total

1.  Soluble epoxide hydrolase regulates hematopoietic progenitor cell function via generation of fatty acid diols.

Authors:  Timo Frömel; Benno Jungblut; Jiong Hu; Caroline Trouvain; Eduardo Barbosa-Sicard; Rüdiger Popp; Stefan Liebner; Stefanie Dimmeler; Bruce D Hammock; Ingrid Fleming
Journal:  Proc Natl Acad Sci U S A       Date:  2012-06-04       Impact factor: 11.205

2.  The cold-induced lipokine 12,13-diHOME promotes fatty acid transport into brown adipose tissue.

Authors:  Matthew D Lynes; Luiz O Leiria; Morten Lundh; Alexander Bartelt; Farnaz Shamsi; Tian Lian Huang; Hirokazu Takahashi; Michael F Hirshman; Christian Schlein; Alexandra Lee; Lisa A Baer; Francis J May; Fei Gao; Niven R Narain; Emily Y Chen; Michael A Kiebish; Aaron M Cypess; Matthias Blüher; Laurie J Goodyear; Gökhan S Hotamisligil; Kristin I Stanford; Yu-Hua Tseng
Journal:  Nat Med       Date:  2017-03-27       Impact factor: 53.440

3.  Soluble epoxide hydrolase inhibition is antinociceptive in a mouse model of diabetic neuropathy.

Authors:  Karen Wagner; Jun Yang; Bora Inceoglu; Bruce D Hammock
Journal:  J Pain       Date:  2014-06-09       Impact factor: 5.820

4.  Inhibition of soluble epoxide hydrolase reduces LPS-induced thermal hyperalgesia and mechanical allodynia in a rat model of inflammatory pain.

Authors:  Bora Inceoglu; Steven L Jinks; Kara R Schmelzer; Troy Waite; In Hae Kim; Bruce D Hammock
Journal:  Life Sci       Date:  2006-08-02       Impact factor: 5.037

5.  Inhibition of soluble epoxide hydrolase modulates inflammation and autophagy in obese adipose tissue and liver: role for omega-3 epoxides.

Authors:  Cristina López-Vicario; José Alcaraz-Quiles; Verónica García-Alonso; Bibiana Rius; Sung H Hwang; Esther Titos; Aritz Lopategi; Bruce D Hammock; Vicente Arroyo; Joan Clària
Journal:  Proc Natl Acad Sci U S A       Date:  2014-12-30       Impact factor: 11.205

6.  Dihydroxyoctadecamonoenoate esters inhibit the neutrophil respiratory burst.

Authors:  David Alan Thompson; Bruce D Hammock
Journal:  J Biosci       Date:  2007-03       Impact factor: 1.826

7.  Biosynthesis of leukotoxin, 9,10-epoxy-12 octadecenoate, by leukocytes in lung lavages of rat after exposure to hyperoxia.

Authors:  T Ozawa; M Hayakawa; T Takamura; S Sugiyama; K Suzuki; M Iwata; F Taki; T Tomita
Journal:  Biochem Biophys Res Commun       Date:  1986-02-13       Impact factor: 3.575

8.  Differential effects of soluble epoxide hydrolase inhibition and CYP2J2 overexpression on postischemic cardiac function in aged mice.

Authors:  Ketul R Chaudhary; Beshay N M Zordoky; Matthew L Edin; Nasser Alsaleh; Ayman O S El-Kadi; Darryl C Zeldin; John M Seubert
Journal:  Prostaglandins Other Lipid Mediat       Date:  2012-08-16       Impact factor: 3.072

9.  A case series of the dynamics of lipid mediators in patients with sepsis.

Authors:  Mitsuhide Hamaguchi; Heng Ning Wu; Masahiro Tanaka; Noriko Tsuda; Ourlad Alzeus Gaddi Tantengco; Tomohide Matsushima; Takami Nakao; Takuya Ishibe; Ikuhiro Sakata; Itaru Yanagihara
Journal:  Acute Med Surg       Date:  2019-07-18

10.  Bioactivation of leukotoxins to their toxic diols by epoxide hydrolase.

Authors:  M F Moghaddam; D F Grant; J M Cheek; J F Greene; K C Williamson; B D Hammock
Journal:  Nat Med       Date:  1997-05       Impact factor: 53.440

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  23 in total

Review 1.  Linoleic acid and the regulation of glucose homeostasis: A review of the evidence.

Authors:  Jakob S Hamilton; Eric L Klett
Journal:  Prostaglandins Leukot Essent Fatty Acids       Date:  2021-10-29       Impact factor: 4.006

Review 2.  Heme-oxygenase and lipid mediators in obesity and associated cardiometabolic diseases: Therapeutic implications.

Authors:  John A McClung; Lior Levy; Victor Garcia; David E Stec; Stephen J Peterson; Nader G Abraham
Journal:  Pharmacol Ther       Date:  2021-09-06       Impact factor: 12.310

3.  Intestinal metabolomics of juvenile lenok (Brachymystax lenok) in response to heat stress.

Authors:  Yan Chen; Yang Liu; Yucen Bai; Shaogang Xu; Xiaofei Yang; Bo Cheng
Journal:  Fish Physiol Biochem       Date:  2022-09-28       Impact factor: 3.014

4.  Improved ELISA for linoleate-derived diols in human plasma utilizing a polyHRP-based secondary tracer.

Authors:  Nalin Singh; Dongyang Li; Cindy B McReynolds; Christophe Morisseau; Bruce D Hammock
Journal:  Anal Methods       Date:  2022-05-13       Impact factor: 3.532

Review 5.  Soluble Epoxide Hydrolase as a Therapeutic Target for Neuropsychiatric Disorders.

Authors:  Jiajing Shan; Kenji Hashimoto
Journal:  Int J Mol Sci       Date:  2022-04-29       Impact factor: 6.208

Review 6.  The Role of Epoxyeicosatrienoic Acids in Cardiac Remodeling.

Authors:  Jinsheng Lai; Chen Chen
Journal:  Front Physiol       Date:  2021-02-24       Impact factor: 4.566

Review 7.  Eicosanoid Signaling in Insect Immunology: New Genes and Unresolved Issues.

Authors:  Yonggyun Kim; David Stanley
Journal:  Genes (Basel)       Date:  2021-02-01       Impact factor: 4.096

8.  Plasma Linoleate Diols Are Potential Biomarkers for Severe COVID-19 Infections.

Authors:  Cindy B McReynolds; Irene Cortes-Puch; Resmi Ravindran; Imran H Khan; Bruce G Hammock; Pei-An Betty Shih; Bruce D Hammock; Jun Yang
Journal:  Front Physiol       Date:  2021-04-01       Impact factor: 4.566

9.  Untargeted Metabolomics Analysis of the Serum Metabolic Signature of Childhood Obesity.

Authors:  Lukasz Szczerbinski; Gladys Wojciechowska; Adam Olichwier; Mark A Taylor; Urszula Puchta; Paulina Konopka; Adam Paszko; Anna Citko; Joanna Goscik; Oliver Fiehn; Sili Fan; Anna Wasilewska; Katarzyna Taranta-Janusz; Adam Kretowski
Journal:  Nutrients       Date:  2022-01-04       Impact factor: 5.717

10.  Linoleic Acid-Derived Oxylipins Differentiate Early Stage Alcoholic Hepatitis From Mild Alcohol-Associated Liver Injury.

Authors:  Dennis Warner; Vatsalya Vatsalya; Kara H Zirnheld; Jeffrey B Warner; Josiah E Hardesty; John C Umhau; Craig J McClain; Krishnarao Maddipati; Irina A Kirpich
Journal:  Hepatol Commun       Date:  2021-02-09
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