ArticleThe Journal of biological chemistry2009
Biogenic synthesis, purification, and chemical characterization of anti-inflammatory resolvins derived from docosapentaenoic acid (DPAn-6).
Article in The Journal of biological chemistry, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed, 67 citations in OpenAlex.
- Trial
- Correlation between omega-3 intake and the incidence of diabetic retinopathy based on NHANES from 2005 to 2008.Acta diabetologica · 2024Article
- Polydopamine-Based Biomaterials in Orthopedic Therapeutics: Properties, Applications, and Future Perspectives.Drug design, development and therapy · 2024Review
- Resolvins, Protectins, and Maresins: DHA-Derived Specialized Pro-Resolving Mediators, Biosynthetic Pathways, Synthetic Approaches, and Their Role in Inflammation.Molecules (Basel, Switzerland) · 2022Review
- Molecular and metabolomic changes in the proximal colon of pigs infected with Trichuris suis.Scientific reports · 2020Article
- Directed Non-targeted Mass Spectrometry and Chemical Networking for Discovery of Eicosanoids and Related Oxylipins.Cell chemical biology · 2019Article
- Dietary PUFAs attenuate NLRP3 inflammasome activation via enhancing macrophage autophagy.Journal of lipid research · 2017Article
- Increased ω6-Containing Phospholipids and Primary ω6 Oxidation Products in the Brain Tissue of Rats on an ω3-Deficient Diet.PloS one · 2016Article
- Controlled formation of mono- and dihydroxy-resolvins from EPA and DHA using soybean 15-lipoxygenase.Journal of lipid research · 2013Article
- A review of the biologic and pharmacologic role of docosapentaenoic acid n-3.F1000Research · 2013Review
- Omega-6 docosapentaenoic acid-derived resolvins and 17-hydroxydocosahexaenoic acid modulate macrophage function and alleviate experimental colitis.Inflammation research : official journal of the European Histamine Research Society ... [et al.] · 2012Article
- Fifteen weeks of dietary n-3 polyunsaturated fatty acid deprivation increase turnover of n-6 docosapentaenoic acid in rat-brain phospholipids.Biochimica et biophysica acta · 2012Article
- Omega-3 fatty acids cause dramatic changes in TLR4 and purinergic eicosanoid signaling.Proceedings of the National Academy of Sciences of the United States of America · 2012Article
- (n-3) fatty acids and cardiovascular health: are effects of EPA and DHA shared or complementary?The Journal of nutrition · 2012Review
- 15-lipoxygenase metabolites of docosahexaenoic acid inhibit prostate cancer cell proliferation and survival.PloS one · 2012Article
- Regulation of rat brain polyunsaturated fatty acid (PUFA) metabolism during graded dietary n-3 PUFA deprivation.Prostaglandins, leukotrienes, and essential fatty acids · 2011Article
- Resolvins and protectins in inflammation resolution.Chemical reviews · 2011Review
- LC/ESR/MS study of pH-dependent radical generation from 15-LOX-catalyzed DPA peroxidation.Free radical biology & medicine · 2011Article
- Finding homes for orphan cytochrome P450s: CYP4V2 and CYP4F22 in disease states.Molecular interventions · 2011Review
- Specialized pro-resolving lipid mediators in the inflammatory response: An update.Biochimica et biophysica acta · 2010Review
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Authors and funding
7 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Enzymatically oxygenated derivatives of the omega-3 fatty acids cis-4,7,10,13,16,19-docosahexaenoic acid (DHA) and cis-5,8,11,14,17-eicosapentaenoic acid, known as resolvins, have potent inflammation resolution activity (Serhan, C. N., Clish, C. B., Brannon, J., Colgan, S. P., Chiang, N., and Gronert, K. (2000) J. Exp. Med. 192, 1197-1204; Hong, S., Gronert, K., Devchand, P. R., Moussignac, R., and Serhan, C. N. (2003) J. Biol. Chem. 278, 14677-14687). Our objective was to determine whether similar derivatives are enzymatically synthesized from other C-22 fatty acids and whether these molecules possess inflammation resolution properties. The reaction of DHA, DPAn-3, and DPAn-6 with 5-, 12-, and 15-lipoxygenases produced oxylipins, which were identified and characterized by liquid chromatography coupled with tandem mass-spectrometry. DPAn-6 and DPAn-3 proved to be good substrates for 15-lipoxygenase. 15-Lipoxygenase proved to be the most efficient enzyme of the three tested for conversion of long chain polyunsaturated fatty acids to corresponding oxylipins. Since DPAn-6 is a major component of Martek DHA-S oil, we focused our attention on reaction products obtained from the DPAn-6 and 15-lipoxygenase reaction. (17S)-hydroxy-DPAn-6 and (10,17S)-dihydroxy-DPAn-6 were the main products of this reaction. These compounds were purified by preparatory high performance liquid chromatography techniques and further characterized by NMR, UV spectrophotometry, and tandem mass spectrometry. We tested both compounds in two animal models of acute inflammation and demonstrated that both compounds are potent anti-inflammatory agents that are active on local intravenous as well as oral administration. These oxygenated DPAn-6 compounds can thus be categorized as a new class of DPAn-6-derived resolvins.
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