10-Nitrooleate-d
17 is intended for use as an internal standard for the quantification of 10-nitrooleate by GC- or LC-MS. Nitrated unsaturated fatty acids, such as 10- and 12-nitrolinoleate (LNO
2; ）, cholesteryl nitrolinoleate, and nitrohydroxylinoleate, represent a new class of endogenous lipid-derived signalling molecules. LNO
2 isomers serve as potent endogenous ligands for PPARγ and can also decompose or be metabolized to release nitric oxide.
1,2,3,4 10-Nitrooleate is one of two regioisomers of nitrooleate, the other being 9-nitrooleate (OA-NO
2; used for the mixture of isomers), which are formed by nitration of oleic acid in approximately equal proportions
in vivo.
5 Peroxynitrite, acidified nitrite, and myeloperoxidase in the presence of H
2O
2 and nitrite, all mediate the nitration of oleic acid. OA-NO
2 is found in human plasma as the free acid and esterified in phospholipids at concentrations of 619 ± 52 nM and 302 ± 369 nM, respectively. OA-NO
2 activates PPARγ approximately 7-fold at a concentration of 1 μM and effectively promotes differentiation 3T3-L1 preadipocytes to adipocytes at 3 μM.
5
1. Lim, D.G., Sweeney, S., Bloodsworth, A., et al. Nitrolinoleate, a nitric oxide-derived mediator of cell function: Synthesis, characterization, and vasomotor activity Proc. Natl. Acad. Sci. USA 99(25),15941-15946(2002).
2. Schopfer, F.J., Lin, Y., Baker, P.R.S., et al. Nitrolinoleic acid: An endogenous peroxisome proliferator-activated receptor γ ligand Proc. Natl. Acad. Sci. USA 102(7),2340-2345(2005).
3. Lima, E.S., Bonini, M.G., Augusto, O., et al. Nitrated lipids decompose to nitric oxide and lipid radicals and cause vasorelaxation Free Radic. Biol. Med. 39(4),532-539(2005).
4. Baker, P.R.S., Schopfer, F.J., Sweeney, S., et al. Red cell membrane and plasma linoleic acid nitration products: Synthesis, clinical identification, and quantitation Proc. Natl. Acad. Sci. USA 101(32),11577-11582(2004).
5. Baker, P.R., Lin, Y., Schopfer, F.J., et al. Fatty acid transduction of nitric oxide signaling. Multiple nitrated unsaturated acid derivatives exist in human blood and urine serve as endogenous peroxisome proliferator-activated receptor ligands J. Biol. Chem. 280(51),42464-42475(2005).
