Formation and signaling actions of electrophilic lipids

Schopfer, Francisco J.; Cipollina, Chiara; Freeman, Bruce A.

doi:10.1021/cr200131e

Cited by 299Genomics, phytochemicals, and oxidative stressEicosanoids and Hypertension PharmacologySphingolipid Metabolism and Signaling

Formation and signaling actions of electrophilic lipids

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Schopfer, Francisco J., Cipollina, Chiara, Freeman, Bruce A.·2011·Chemical Reviews

DOI 10.1021/cr200131ePMC PMC3294277

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Abstract

ADVERTISEMENT RETURN TO ISSUEPREVReviewNEXTFormation and Signaling Actions of Electrophilic LipidsFrancisco J. Schopfer†, Chiara Cipollina‡§, and Bruce A. Freeman*†View Author Information† Department of Pharmacology & Chemical Biology, University of Pittsburgh School of Medicine, Pittsburgh, Pennsylvania 15261, United States‡ Fondazione Ri.MED, Piazza Sett'Angeli 10, 90134 Palermo, Italy§ Institute of Biomedicine and Molecular Immunology, Italian National Research Council, Via U. La Malfa 153, 90146 Palermo, ItalyBruce A. Freeman, Ph.D., E1340 Biomedical Science Tower, 200 Lothrop Street, University of Pittsburgh School of Medicine, Pittsburgh, Pennsylvania 15261, United States. Phone: 412-648-9319. Fax: 412-648-2229. E-mail: [email protected]Cite this: Chem. Rev. 2011, 111, 10, 5997–6021Publication Date (Web):September 20, 2011Publication History Received18 April 2011Published online20 September 2011Published inissue 12 October 2011https://pubs.acs.org/doi/10.1021/cr200131ehttps://doi.org/10.1021/cr200131ereview-articleACS PublicationsCopyright © 2011 American Chemical SocietyRequest reuse permissionsArticle Views3642Altmetric-Citations252LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose SUBJECTS:Cell signaling,Electrophiles,Inflammation,Lipids,Peptides and proteins Get e-Alerts

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These reactions lead to generation of electrophilic nitro-fatty acid signaling mediators, including NO2-CLA and S-nitrosothiol derivatives, detected at increased concentrations in systemic circulation following oral consumption of nitrate.
“These reactions also lead to the generation of electrophilic nitro-fatty acid (NO2-FA) signaling mediators, including NO2-conjugated linoleic acid (NO2-CLA) and S-nitrosothiol derivatives, all of which can be detected at increased concentrations in the systemic circulation following oral consumption of nitrate[72,92–96].”
From Enterosalivary nitrate metabolism and the microbiome: Intersection of microbial metabolism, nitric oxide and diet in cardiac and pulmonary vascular health (2017) · cites this paper as [94]
NO2-FAs exert pleiotropic post-translational, anti-oxidant and anti-inflammatory effects that include inhibition of vascular smooth muscle proliferation and neointima formation after injury, cardioprotection, improved endothelial function, and activation of downstream NO signaling pathways.
“NO2-FAs exert pleiotropic post-translational, anti-oxidant and anti-inflammatory effects[105,321,385] that include inhibition of vascular smooth muscle proliferation and neointima formation after injury, cardioprotection, improved endothelial function[94,386–390], and activation of downstream NO signaling pathways[385,389,391–394].”
From Enterosalivary nitrate metabolism and the microbiome: Intersection of microbial metabolism, nitric oxide and diet in cardiac and pulmonary vascular health (2017) · cites this paper as [94]
The unique electrophilic character of fatty acid nitroalkenes promotes the reversible Michael addition of susceptible cysteines in a limited number of transcriptional regulatory factors and enzymes.
“The unique electrophilic character of fatty acid nitroalkenes promotes the reversible Michael addition of susceptible cysteines in a limited number of transcriptional regulatory factors and enzymes [11].”
From Nitrite and nitrate-dependent generation of anti-inflammatory fatty acid nitroalkenes (2015) · cites this paper as [11]
This post-translational modification of functionally-significant hyperreactive thiols induces pleiotropic responses that include the cGMP-independent activation of transcriptional programs regulated by Nrf2 and nuclear lipid receptors, as well as inhibition of pro-inflammatory signaling by NF-kβ.
“This post-translational modification of functionally-significant hyperreactive thiols induces pleiotropic responses that include the cGMP-independent activation of transcriptional programs regulated by nuclear factor (erythroid-derived-2)-like 2 (Nrf2) and nuclear lipid receptors, as well as inhibition of pro-inflammatory signaling by nuclear factor kappa-β (NF-kβ) [12–15].”
From Nitrite and nitrate-dependent generation of anti-inflammatory fatty acid nitroalkenes (2015) · cites this paper as [14]
Electrophilic nitroalkenes such as NO2-cLA induce kinetically rapid posttranslational modification of nucleophilic cysteines of key transcriptional regulatory proteins and inhibit the activity of functionally-significant electrophile-sensitive enzymes.
“Electrophilic nitroalkenes such as NO2-cLA induce kinetically rapid posttranslational modification of nucleophilic cysteines of key transcriptional regulatory proteins and inhibit the activity of functionally-significant electrophile-sensitive enzymes [11, 33, 34].”
From Nitrite and nitrate-dependent generation of anti-inflammatory fatty acid nitroalkenes (2015) · cites this paper as [11]

The oxidation and nitration of unsaturated fatty acids by oxides of nitrogen yield electrophilic derivatives that can modulate protein function via post-translational protein modifications.
“The oxidation and nitration of unsaturated fatty acids by oxides of nitrogen yield electrophilic derivatives that can modulate protein function via post-translational protein modifications.”
From Conjugated linoleic acid is a preferential substrate for fatty acid nitration (2012) · cites this paper as [2]
NO2-CLA mediates signaling actions analogous to those reported for NO2-LA and NO2-OA.
“To further confirm that NO 2 -CLA mediates signaling actions analogous to those reported for NO 2 -LA and NO 2 -OA (2, 15), HO-1 expression in RAW 264.7 macrophages was evaluated.”
From Conjugated linoleic acid is a preferential substrate for fatty acid nitration (2012) · cites this paper as [2]
Electrophilic derivatives of unsaturated fatty acids (nitroalkene and α,β-unsaturated carbonyl species) are critical proximal mediators of signaling actions, because electrophilic fatty acids are orders of magnitude more potent than native unsaturated fatty acids in modulating tissue-protective and adaptive signaling mechanisms.
“Notably, electrophilic derivatives of these unsaturated fatty acids (i.e.nitroalkene and ␣,␤-unsaturated carbonyl species) are critical proximal mediators of these signaling actions, because electrophilic fatty acids are orders of magnitude more potent than native unsaturated fatty acids in modulating these and other key tissue-protective and adaptive signaling mechanisms (2,3,11).”
From Conjugated linoleic acid is a preferential substrate for fatty acid nitration (2012) · cites this paper as [2]
Electrophilic fatty acid derivatives react with nucleophilic amino acids of proteins via Michael addition, thereby altering protein structure and function.
“Electrophilic fatty acid derivatives react with nucleophilic amino acids of proteins via Michael addition, thereby altering protein structure and function (2).”
From Conjugated linoleic acid is a preferential substrate for fatty acid nitration (2012) · cites this paper as [2]
NO2-FA are orders of magnitude more potent than native fatty acids in modulating similar transcriptional regulatory mechanisms of anti-inflammatory signaling.
“Considering that nitroalkene fatty acid derivatives are readily generated from CLA and that NO 2 -FA are orders of magnitude more potent than native fatty acids in modulating similar transcriptional regulatory mechanisms of anti-inflammatory signaling (2,24), Fig. 6 reveals that nitroalkenes can mediate the transduction of many of the salutary signaling actions noted for both NO 2 Ϫ and CLA.”
From Conjugated linoleic acid is a preferential substrate for fatty acid nitration (2012) · cites this paper as [2]
The endogenous generation of nitrogen dioxide (NO2) occurs via multiple acid-catalyzed and oxidative inflammatory reactions involving nitric oxide (NO) and nitrite (NO2−).
“The endogenous generation of NO2 occurs via multiple acid-catalyzed and oxidative inflammatory reactions involving NO and NO2 − [15].”
From Olives and olive oil are sources of electrophilic fatty acid nitroalkenes (2014) · cites this paper as [15]

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Authors: Schopfer, F. J., Cipollina, C., & Freeman, B. A.
Affiliations: University of Pittsburgh (US)
Istituto di Biomedicina e di Immunologia Molecolare Alberto Monroy (IT)
Department of Pharmacology & Chemical Biology, University of Pittsburgh School of Medicine, Pittsburgh, Pennsylvania 15261, United States
ORCID: Schopfer, Francisco J.
Cipollina, Chiara
Venue: Chemical Reviews
Publisher: American Chemical Society (ACS)
Published: 2011-09-20
Volume: 111
Issue: 10
Pages: 5997-6021
ISSN: 0009-2665 (ISSN-L)
1520-6890
DOI: 10.1021/cr200131e
PMC: PMC3294277
OpenAlex: W2061676392
Cited by: 299
References: 250
Citations by year: 2026: 8 · 2025: 12 · 2024: 18 · 2023: 14 · 2022: 14 · 2021: 20 · 2020: 30 · 2019: 27 · 2018: 28 · 2017: 24 · 2016: 26 · 2015: 17 · 2014: 24 · 2013: 22 · 2012: 14
FWCI: 1.74
Type: journal article
Language: en
Open access: green
www.ncbi.nlm.nih.gov
Locations: Chemical Reviews (publishedVersion)
PubMed (publishedVersion)
Europe PMC (PubMed Central) (acceptedVersion)
PubMed Central (acceptedVersion)
Funders: National Heart, Lung, and Blood Institute (R01HL64937, R01HL064937, R37HL058115, R01HL058115, P01HL103455, R01HL132550)
National Institute of Diabetes and Digestive and Kidney Diseases (P30DK072506)
Topics: Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Genomics, phytochemicals, and oxidative stress
Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Eicosanoids and Hypertension Pharmacology
Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Sphingolipid Metabolism and Signaling
Keywords: lipid signaling, lipid oxidation, reactive oxygen species, lipid peroxidation, lipid oxidation products
MeSH terms: Amino Acids, Animals, Fatty Acids, Humans, Oxidation-Reduction, Proteins, Signal Transduction, Lipid Metabolism

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Formation and signaling actions of electrophilic lipids

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