Cyclooxygenase-2 generates anti-inflammatory mediators from omega-3 fatty acids
Open accessAbstract
Electrophilic fatty acids are generated during inflammation by non-enzymatic reactions and can modulate inflammatory responses. We used a new mass spectrometry-based electrophile capture strategy to reveal the formation of electrophilic oxo-derivatives (EFOX) from the omega-3 fatty acids docosahexaenoic acid (DHA) and docosapentaenoic acid (DPA). These EFOX were generated by a cyclooxygenase-2 (COX-2)-catalyzed mechanism in activated macrophages. Modulation of COX-2 activity by aspirin increased the rate of EFOX production and their intracellular levels. Owing to their electrophilic nature, EFOX adducted to cysteine and histidine residues of proteins and activated Nrf2-dependent anti-oxidant gene expression. We confirmed the anti-inflammatory nature of DHA- and DPA-derived EFOX by showing that they can act as peroxisome proliferator-activated receptor-gamma (PPAR gamma) agonists and inhibit pro-inflammatory cytokine and nitric oxide production, all within biological concentration ranges. These data support the idea that EFOX are signaling mediators that transduce the beneficial clinical effects of omega-3 fatty acids, COX-2 and aspirin.
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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 [3]
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 [3]
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- Authors
- Groeger, A. L., Cipollina, C., Cole, M. P., Woodcock, S. R., Bonacci, G., Rudolph, T. K., Rudolph, V., Freeman, B. A., & Schopfer, F. J.
- Affiliations
- University of Pittsburgh (US)
- Universität Hamburg (DE)
- Corresponding author
- Schopfer, Francisco J
- ORCID
- Venue
- Nature Chemical Biology
- Published
- 2010-05-02
- Volume
- 6
- Issue
- 6
- Pages
- 433-441
- ISSN
- 1552-4450 (ISSN-L)
- 1552-4469
- PMC
- PMC3077712
- OpenAlex
- W2016008825
- Cited by
- 295
- References
- 64
- Citations by year
- 2026: 7 · 2025: 9 · 2024: 17 · 2023: 9 · 2022: 15 · 2021: 15 · 2020: 13 · 2019: 17 · 2018: 18 · 2017: 17 · 2016: 21 · 2015: 23 · 2014: 22 · 2013: 24 · 2012: 23
- FWCI
- 27.62
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Licence
- www.springer.com/tdm (tdm)
- Locations
- Nature Chemical Biology (publishedVersion)
- PubMed (publishedVersion)
- Europe PMC (PubMed Central) (acceptedVersion)
- PubMed Central (acceptedVersion)
- Funders
- National Institutes of Health
- National Heart, Lung, and Blood Institute (HL 64937, R01HL064937, HL 58115, R37HL058115, R01HL058115, K99HL095769)
- Topics
- Health Sciences › Nursing › Nutrition and Dietetics › Fatty Acid Research and Health
- Health Sciences › Medicine › Pharmacology › Inflammatory mediators and NSAID effects
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Eicosanoids and Hypertension Pharmacology
- Keywords
- cyclooxygenase-2, omega-3 fatty acids, docosahexaenoic acid, docosapentaenoic acid, macrophages, aspirin, Nrf2, PPARγ agonists, anti-inflammatory signaling, nitric oxide, inflammatory cytokines, inflammation
- MeSH terms
- Anti-Inflammatory Agents, Borohydrides, Cell Line, Cell Membrane, Docosahexaenoic Acids, Fatty Acids, Unsaturated, Glutathione, Humans, Hydroxylation, Macrophages, Fatty Acids, Omega-3, Interleukin-6, Interleukin-10, PPAR gamma, Cyclooxygenase 2
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