ArticleJournal of natural products2014
Total synthesis of the lipid mediator PD1n-3 DPA: configurational assignments and anti-inflammatory and pro-resolving actions.
Article in Journal of natural products, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 52 papers.
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
52 citing papers in PubMed, 97 citations in OpenAlex.
- Clinical Benefits of n-3 PUFA and ɤ-Linolenic Acid in Patients with Rheumatoid Arthritis.Nutrients · 2017Trial
- Efficient One-Step Production of 7S,17S- and 10S,17S-Dihydroxydocosahexaenoic Acids by a Double-Oxygenating 15S-Lipoxygenase From Chlamydomonas incerta.Biotechnology and bioengineering · 2025Article
- Associations between omega-3 fatty acid-derived lipid mediators and markers of inflammation in older subjects with low-grade chronic inflammation.Prostaglandins & other lipid mediators · 2025Article
- Effects of age on lacrimal gland bioactive lipids.The ocular surface · 2024Article
- Biology and Total Synthesis of n-3 Docosapentaenoic Acid-Derived Specialized Pro-Resolving Mediators.Molecules (Basel, Switzerland) · 2024Review
- Accumulation of docosapentaenoic acid (n-3 DPA) in a novel isolate of the marine ichthyosporean Sphaeroforma arctica.Biotechnology letters · 2024Article
- Fatty Acids and their Proteins in Adipose Tissue Inflammation.Cell biochemistry and biophysics · 2024Review
- Polydopamine-Based Biomaterials in Orthopedic Therapeutics: Properties, Applications, and Future Perspectives.Drug design, development and therapy · 2024Review
- The potential role of n-3 fatty acids and their lipid mediators on asthmatic airway inflammation.Frontiers in immunology · 2024Review
- Metabolization of Resolvin E4 by ω-Oxidation in Human Neutrophils: Synthesis and Biological Evaluation of 20-Hydroxy-Resolvin E4 (20-OH-RvE4).ACS pharmacology & translational science · 2023Article
- Stereoselective Synthesis, Pro-resolution, and Anti-inflammatory Actions of RvD5Journal of natural products · 2023Article
- Possibility of averting cytokine storm in SARS-COV 2 patients using specialized pro-resolving lipid mediators.Biochemical pharmacology · 2023Review
- Protectins: Their biosynthesis, metabolism and structure-functions.Biochemical pharmacology · 2022Review
- Impact of health and lifestyle food supplements on periodontal tissues and health.Periodontology 2000 · 2022Review
- Resolvins, Protectins, and Maresins: DHA-Derived Specialized Pro-Resolving Mediators, Biosynthetic Pathways, Synthetic Approaches, and Their Role in Inflammation.Molecules (Basel, Switzerland) · 2022Review
- Stereoselective Synthesis, Configurational Assignment and Biological Evaluations of the Lipid Mediator RvD2Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- The associations of circulating common and uncommon polyunsaturated fatty acids and modification effects on dietary quality with all-cause and disease-specific mortality in NHANES 2003-2004 and 2011-2012.Annals of medicine · 2021Article
- Total Synthesis and Anti-Inflammatory Bioactivity of (-)-Majusculoic Acid and Its Derivatives.Marine drugs · 2021Article
- A new synthetic protectin D1 analog 3-oxa-PD1Organic & biomolecular chemistry · 2021Article
- Stereoselective Synthesis and Structural Confirmation of the Specialized Pro-Resolving Mediator Resolvin E4.The Journal of organic chemistry · 2021Article
Corrections and comments
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Authors and funding
8 authors at 3 institutions in 2 countries.
Funding
Abstract
The polyunsaturated lipid mediator PD1n-3 DPA (5) was recently isolated from self-resolving inflammatory exudates of 5 and human macrophages. Herein, the first total synthesis of PD1n-3 DPA (5) is reported in 10 steps and 9% overall yield. These efforts, together with NMR data of its methyl ester 6, confirmed the structure of 5 to be (7Z,10R,11E,13E,15Z,17S,19Z)-10,17-dihydroxydocosa-7,11,13,15,19-pentaenoic acid. The proposed biosynthetic pathway, with the involvement of an epoxide intermediate, was supported by results from trapping experiments. In addition, LC-MS/MS data of the free acid 5, obtained from hydrolysis of the synthetic methyl ester 6, matched data for the endogenously produced biological material. The natural product PD1n-3 DPA (5) demonstrated potent anti-inflammatory properties together with pro-resolving actions stimulating human macrophage phagocytosis and efferocytosis. These results contribute new knowledge on the n-3 DPA structure-function of the growing numbers of specialized pro-resolving lipid mediators and pathways.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.