The DOI matches its Crossref record; 10 of the 10 references it cites were found in a registry or an index.
Anti-Inflammatory Actions of Neuroprotectin D1/Protectin D1 and Its Natural Stereoisomers: Assignments of Dihydroxy-Containing Docosatrienes
Abstract
Protectin D1, neuroprotectin D1 when generated by neural cells, is a member of a new family of bioactive products generated from docosahexaenoic acid. The complete stereochemistry of protectin D1 (10,17S-docosatriene), namely, chirality of the carbon-10 alcohol and geometry of the conjugated triene, required for bioactivity remained to be assigned. To this end, protectin D1/neuroprotectin D1 (PD1) generated by human neutrophils during murine peritonitis and by neural tissues was separated from natural isomers and subjected to liquid chromatography-tandem mass spectrometry and gas chromatography-mass spectrometry. Comparisons with six 10,17-dihydroxydocosatrienes prepared by total organic and biogenic synthesis showed that PD1 from human cells carrying potent bioactivity is 10R,17S-dihydroxy-docosa-4Z,7Z,11E,13E,15Z,19Z-hexaenoic acid. Additional isomers identified included trace amounts of Δ15-trans-PD1 (isomer III), 10S,17S-dihydroxy-docosa-4Z,7Z,11E,13Z,15E,19Z-hexaenoic acid (isomer IV), and a double dioxygenation product 10S,17S-dihydroxy-docosa-4Z,7Z,11E,13Z,15E,19Z-hexaenoic acid (isomer I), present in exudates. 18O2 labeling showed that 10S,17S-diHDHA (isomer I) carried 18O in the carbon-10 position alcohol, indicating sequential lipoxygenation, whereas PD1 formation proceeded via an epoxide. PD1 at 10 nM attenuated (∼50%) human neutrophil transmigration, whereas Δ15-trans-PD1 was essentially inactive. PD1 was a potent regulator of polymorphonuclear leukocyte (PMN) infiltration (∼40% at 1 ng/mouse) in peritonitis. The rank order at 1- to 10-ng dose was PD1 ≈ PD1 methyl ester ≫ Δ15-trans-PD1 > 10S,17S-diHDHA (isomer I). 10S,17S-dihydroxy-docosa-4Z,7Z,11E,13E,15Z,19Z-hexaenoic acid (isomer VI) proved ≥ PD1 in blocking PMN infiltration, but was not a major product of leukocytes. PD1 also reduced PMN infiltration after initiation (2 h) of inflammation and was additive with resolvin E1. These results indicate that PD1 is a potent stereoselective anti-inflammatory molecule.
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Cites
Coussens, L. M., & Werb, Z. (2002) · Nature · doi:10.1038/nature01322 · Cited by 15,111
Inflammation in atherosclerosis
Libby, P. (2002) · Nature · doi:10.1038/nature01323 · Cited by 8,315
Points of control in inflammation
Nathan, C. (2002) · Nature · doi:10.1038/nature01320 · Cited by 2,738
Lipid mediator class switching during acute inflammation: signals in resolution
Levy, B. D., Clish, C. B., Schmidt, B., Gronert, K., & Serhan, C. N. (2001) · Nature Immunology · doi:10.1038/89759 · Cited by 1,453
Self-citationMarchioli, R., Barzi, F., Bomba, E., Chieffo, C., Di Gregorio, D., Di Mascio, R., Franzosi, M. G., Geraci, E., Levantesi, G., Maggioni, A. P., et al. (2002) · Circulation · doi:10.1161/01.cir.0000014682.14181.f2 · Cited by 1,311
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Self-citationHong, S., Gronert, K., Devchand, P. R., Moussignac, R.-L., & Serhan, C. N. (2003) · Journal of Biological Chemistry · doi:10.1074/jbc.m300218200 · Cited by 1,000
Self-citationMechanisms of action of docosahexaenoic acid in the nervous system
Salem, N., Litman, B., Kim, H., & Gawrisch, K. (2001) · Lipids · doi:10.1007/s11745-001-0805-6 · Cited by 919 · cited 1×
“DHA is enriched in neural tissues, where it appears to play functional as well as structural roles (27, 28).”
BackgroundMarcheselli, V. L., Hong, S., Lukiw, W. J., Tian, X. H., Gronert, K., Musto, A., Hardy, M., Gimenez, J. M., Chiang, N., Serhan, C. N., et al. (2003) · Journal of Biological Chemistry · doi:10.1074/jbc.m305841200 · Cited by 802
Self-citationMukherjee, P. K., Marcheselli, V. L., Serhan, C. N., & Bazan, N. G. (2004) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0402531101 · Cited by 753 · cited 3×
“, 10,17-dihydroxydocosatriene (1, 3, 37); its potent role in neural protection was recently uncovered (2), and thus it is denoted as NPD1 when produced in neural tissues.”
Cited by
Pro-resolving lipid mediators are leads for resolution physiology
Serhan, C. N. (2014) · Nature · doi:10.1038/nature13479 · Cited by 3,041
Self-citationResolving inflammation: dual anti-inflammatory and pro-resolution lipid mediators
Serhan, C. N., Chiang, N., & Van Dyke, T. E. (2008) · Nature Reviews Immunology · doi:10.1038/nri2294 · Cited by 2,932
Self-citationResolvins in inflammation: emergence of the pro-resolving superfamily of mediators
Serhan, C. N., & Levy, B. D. (2018) · Journal of Clinical Investigation · doi:10.1172/jci97943 · Cited by 1,344
Self-citationResolvins and protectins in inflammation resolution
Serhan, C. N., & Petasis, N. A. (2011) · Chemical Reviews · doi:10.1021/cr100396c · Cited by 996
Self-citationMaresins: Novel macrophage mediators with potent antiinflammatory and proresolving actions
Serhan, C. N., Yang, R., Martinod, K., Kasuga, K., Pillai, P. S., Porter, T. F., Oh, S. F., & Spite, M. (2009) · Journal of Experimental Medicine · doi:10.1084/jem.20081880 · Cited by 908
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Metadata
- Authors
- Serhan, C. N., Gotlinger, K., Hong, S., Lu, Y., Siegelman, J., Baer, T., Yang, R., Colgan, S. P., & Petasis, N. A.
- Venue
- The Journal of Immunology
- Publisher
- Oxford University Press (OUP)
- Published
- 2006-02-01
- Volume
- 176
- Issue
- 3
- Pages
- 1848-1859
- ISSN
- 0022-1767 (ISSN-L)
- 1550-6606
- OpenAlex
- W1959056525
- Cited by
- 455
- References
- 10
- FWCI
- 19.18
- Type
- journal article
- Language
- en
- Open access
- closed
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- Serhan, C. N., Gotlinger, K., Hong, S., Lu, Y., Siegelman, J., Baer, T., Yang, R., Colgan, S. P., & Petasis, N. A. (2006). Anti-Inflammatory Actions of Neuroprotectin D1/Protectin D1 and Its Natural Stereoisomers: Assignments of Dihydroxy-Containing Docosatrienes. The Journal of Immunology. https://doi.org/10.4049/jimmunol.176.3.1848
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