17(R)-Resolvin D1

• CAT Number: R060917
• CAS Number: 528583-91-7
• Molecular Formula: C22H32O5
• Molecular Weight: 376.5
• Purity: ≥95%
• Storage: -80°C
• IUPAC Name: 7,8,17-trihydroxydocosa-4,9,11,13,15,19-hexaenoic acid
• InChI: InChI=1S/C22H32O5/c1-2-3-9-14-19(23)15-10-6-4-5-7-11-16-20(24)21(25)17-12-8-13-18-22(26)27/h3-12,15-16,19-21,23-25H,2,13-14,17-18H2,1H3,(H,26,27)/b6-4-,7-5+,9-3-,12-8-,15-10+,16-11+/t19-,20-,21+/m1/s1
• InChIKey: OIWTWACQMDFHJG-BJEBZIPWSA-N
• SMILES: CC/C=CC[C@@H](O)C=CC=CC=C/C=C[C@@H](O)C(O)C/C=CCCC(=O)O

17(R)-Resolvin D1(CAS 528583-91-7) is an aspirin-triggered epimer of RvD1 that reduces human polymorphonuclear leukocyte (PMN) transendothelial migration, the earliest event in acute inflammation, with equipotency to RvD1 (EC50 = ~30 nM). It exhibits a dose-dependent reduction in leukocyte infiltration in a murine model of peritonitis with maximal inhibition of ~35% at a 100 ng dose. In contrast to RvD1, the aspirin-triggered form resists rapid inactivation by eicosanoid oxidoreductases. Analytical and biological comparisons of synthetic 17(R)-RvD1 with endogenously derived 17(R)-RvD1 have confirmed its identity as matching the natural product.

Resolvins are a family of potent lipid mediators derived from both eicosapentaenoic acid and docosahexaenoic acid (DHA). In addition to being anti-<wbr />inflammatory, resolvins promote the resolution of the inflammatory response back to a non-<wbr />inflamed state. Resolvin D1 is produced physiologically from the sequential oxygenation of DHA by 15- and 5-lipoxygenase. 

Reference

1.Hong, S.,Gronert, K.,Devchand, P.R., et al. Novel docosatrienes and 17S-resolvins generated from docosahexaenoic acid in murine brain, human blood, and glial cells. Autacoids in anti-inflammation. The Journal of Biological Chemisty 278(17), 14677-14687
2.Sun, Yee-Ping, et al. "Resolvin D1 and its aspirin-triggered 17R epimer: stereochemical assignments, anti-inflammatory properties, and enzymatic inactivation." Journal of Biological Chemistry 282.13 (2007): 9323-9334.
3.Ariel, Amiram, and Charles N. Serhan. "Resolvins and protectins in the termination program of acute inflammation." Trends in immunology 28.4 (2007): 176-183.