On the structure and synthesis of neuroprotectin D1, a novel anti-inflammatory compound of the docosahexaenoic acid family

Journal of Lipid Research

Volumn 46, Issue 11, 2005, Pages 2311-2314

  Butovich, Igor A ^a  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

10,17(S) docosatriene; 10,17 dihydroxy docosahexaenoic acid; cis, trans geometry; Double lipoxygenation; Lipoxygenase; Nuclear magnetic resonance

Indexed keywords

ANTIINFLAMMATORY AGENT; DOCOSAHEXAENOIC ACID; LIPOXYGENASE; NEUROPROTECTIN D1; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; EPOXIDATION; GEOMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

ANTI-INFLAMMATORY AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DOCOSAHEXAENOIC ACIDS; LIPOXYGENASE; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; SOLANUM TUBEROSUM; SOYBEANS;

EID: 27444443980     PISSN: 00222275     EISSN: None     Source Type: Journal    
DOI: 10.1194/jlr.C500015-JLR200     Document Type: Article

References (15)

1. Bannenberg, G. L., N. Chiang, A. Ariel, M. Arita, E. Tjonahen, K. H. Gotlinger, S. Hong, and C. N. Serhan. 2005. Molecular circuits of resolution: formation and action of resolvins and protectins. J. Immunol. 174: 4345-4355.
2. Serhan, C. N., M. Arita, S. Hong, and K. Godinger. 2004. Resolvins, docosatrienes, and neuroprotectins, novel omega-3 derived mediators, and their endogenous aspirin-triggered epimers. Lipids. 39:1125-1132.
3. Mukhenee, P. K., V. L. Marcheselli, C. N. Serhan, and N. G. Bazan. 2004. Neuroprotectin D1: a docosahexaenoic acid-derived docosatriene protects human retinal pigment epithelial cells from oxidative stress. Proc. Natl. Acad. Sci. USA. 101: 8491-8496.
4. Serhan, C. S., K. Gotlinger, S. Hong, and M. Arita. 2004. Resolvins, docosatrienes, and neuroprotectins, novel omega-3-derived mediators, and their aspirin-triggered endogenous epimers: an overview of their protective roles in catabasis. Prostaglandins Other Lipid Mediat. 73: 155-172.
5. Serhan, C. N. 2005. Novel ω-3-derived local mediators in anti-inflammation and resolution. Pharmacol. Ther. 105: 7-21.
6. Marcheselli, V. L., S. Hong, W. Lukiw, X. H. Tian, K. Gronert, A. Musto, M. Hardy, J. M. Gimenez, N. Chiang, C. N. Serhan, et al. 2003. Novel docosanoids inhibit ischemia-reperfusion-mediated leukocyte infiltration and pro-inflammatory gene expression. J. Biol. Chem. 278: 43807-43817.
7. Hong, S., K. Gronert, P. R. Devchand, R. L. Moussignas, and C. N. Serhan. 2003. Novel docosatrienes and 17(S)-resolvins generated from docosahexaenoic acid in murine brain, human blood, and glial cells. J. Biol. Chem. 278: 14677-14687.
8. Butovich, I. A., M. Hamberg, and O. Radmark. 2005. Novel oxylipins formed from docosahexaenoic acid by potato lipoxygenase-10(S)-hydroxydocosahexaenoic acid and 10,20-dihydroxy-docosahexaenoic acid. Lipids. 40: 249-257.
9. Butovich, I. A., S. M. Luk'yanova, and C. C. Reddy. 2000. Oxidation of linoleyl alcohol by potato tuber lipoxygenase: kinetics and positional, stereo, and geometrical (cis, trans) specificity of the reaction. Arch. Biochem. Biophys. 378: 65-77.
10. Butovich, I. A., and C. C. Reddy. 2001. Enzyme-catalyzed and enzyme-triggered pathways in dioxygenation of 1-monolinoleoyl-rac-glycerol by potato tuber lipoxygenase. Biochim. Biophys. Acta. 1546: 379-398.
11. Jiang, Z. D., S. O. Ketchum, and W. H. Gerwick. 2000. 5-Lipoxy-genase-derived oxylipins from the red alga Rhodymenia pertusa. Phytochemistry. 53: 129-133.
12. Gravel, J., J.-P. Falgueyret, J. Yergey, L. Trimble, and D. Riendeau. 1993. Identification of 5-keto-(7E,9E,11Z,14Z)-eicosatetraenoic acid as a novel nonenzymatic rearrangement product of leukotriene A4. Arch. Biochem. Biophys. 306: 469-475.
13. Radmark, O., C. Serhan, M. Hamberg, U. Lundberg, M. D. Ennis, G. L. Bundy, T. D. Oglesby, P. A. Aristoff, A. W. Harrison, G. Slomp, et al. 1984. Stereochemistry, total synthesis, and biological activity of 14,15-dihydroxy-5,8,10,12-eicosatetraenoic acid. J. Biol. Chem. 259: 13011-13016.
14. Kitamura, S., T. Shimizu, I. Miki, T. Izumi, T. Kasama, A. Sato, H. Sano, and Y. Seyama. 1988. Synthesis and structural identification of four dihydroxy acids and 11,12-leukotriene C4 derived from 11,12-leukotriene A4. Eur. J. Biochem. 176: 725-731.
15. Gronert, K., N. Maheshwari, N. Khan, I. R. Hassan, M. Dunn, and M. L. Schwartzmann. 2005. A role for the mouse 12/15-lipoxygenase pathway in promoting epithelial wound healing and host defense. J. Biol. Chem. 280: 15267-15278.