Characterization of Nitro Arachidonic Acid and Nitro Linoleic Acid by Mass Spectrometry

@article{Chakravartula2012CharacterizationON,
  title={Characterization of Nitro Arachidonic Acid and Nitro Linoleic Acid by Mass Spectrometry},
  author={Srinivas V. S. Chakravartula and Michael Balazy},
  journal={Analytical Letters},
  year={2012},
  volume={45},
  pages={2412 - 2424}
}
Nitration of arachidonic and linoleic acids was performed with nitronium tetrafluroborate, nitrogen dioxide, and dinitrogen trioxide. The nitro compounds were separated on HPLC and characterized further on mass spectrometry. Formation of nitro arachidonic acid m/z 348 and nitro linoleic acid m/z 324 were observed with all the reagents. Interestingly, MS/MS of nitro AA and nitro LA showed specific ions m/z 142, m/z 193, and m/z 206 for nitro arachidonic and m/z 156 and m/z 196 for linoleic acid… 
Profile of Phosphatidylserine Modifications under Nitroxidative Stress Conditions Using a Liquid Chromatography-Mass Spectrometry Based Approach
TLDR
This in vitro model of nitration based on LC-MS/MS provided additional insights into the nitrated and nitroxidized derivatives of PS and their fragmentation fingerprinting.
Recent Advances on Mass Spectrometry Analysis of Nitrated Phospholipids.
TLDR
A mass spectrometry (MS) based approach is developed which allows identifying nitroalkenes derivatives of three major PL classes found in living systems: phosphatidylcholines (PCs),osphatidylethanolamine (PEs), and phosph atidylserines (PSs) and developed method was used to identify NO2-PL in cardiac mitochondria from a well-characterized animal model of type 1 diabetes mellitus.
New Insights into the Anti-Inflammatory and Antioxidant Properties of Nitrated Phospholipids.
TLDR
Nitrated POPC showed anti-inflammatory potential, as assessed by the inhibition of inducible nitric oxide synthase (iNOS) expression in RAW 264.7 macrophages activated by the Toll-like receptor 4 (TLR4) agonist lipopolysaccharide (LPS) in a well-described in vitro model of inflammation.
Advancing Target Identification of Nitrated Phospholipids in Biological Systems by HCD Specific Fragmentation Fingerprinting in Orbitrap Platforms
TLDR
The results showed that the intensity of the typical neutral loss of nitrous acid (HNO2) diminishes with increasing NCE, becoming non-detectable for a higher NCE and the loss of HNO2 could not be the most suitable ion/fragment for the characterization of nitrated phospholipids under HCD.

References

SHOWING 1-10 OF 30 REFERENCES
Isomerization and nitro-oxidation of arachidonic acid by NO2.
TLDR
This work studied the reaction of NO2 with arachidonic acid to characterize lipid products and their biological activity and usefulness as markers of No2 interaction with biological membranes.
Characterization of linoleic acid nitration in human blood plasma by mass spectrometry.
TLDR
Stable products with m/z of 324 and 340, which possessed the same chromatographic characteristics and fragmentation pattern as synthesized standards, were found in human plasma of normolipidemic and hyperlipidemic donors, suggesting the presence of these novel nitrogen-containing oxidized lipid adducts in human Plasma could represent "footprints" of the antioxidant action of *NO on lipid oxidation and/or a pro-oxidant and nitrating action of *.
Vicinal nitrohydroxyeicosatrienoic acids: vasodilator lipids formed by reaction of nitrogen dioxide with arachidonic acid.
TLDR
The oxidation product of NO, NO2, reacts with arachidonic acid to generate biologically active vicinal nitrohydroxyeicosatrienoic acids, which may be important endogenous mediators of vascular relaxation and sGC activation.
Synthesis, isomer characterization, and anti-inflammatory properties of nitroarachidonate.
TLDR
The isomer distribution of nitroarachidonate (AANO2) is synthesized and determined for the first time and demonstrated its ability to modulate inflammation and provide unique structural evidence and novel regulatory signaling properties of AANO1.
Red cell membrane and plasma linoleic acid nitration products: synthesis, clinical identification, and quantitation.
TLDR
It is affirm that basal oxidative and nitrating conditions occur in healthy humans to an extent that is sufficient to induce abundant membrane and lipoprotein-fatty acid nitration.
Nitrogen dioxide induces cis-trans-isomerization of arachidonic acid within cellular phospholipids. Detection of trans-arachidonic acids in vivo.
TLDR
Free radical processes mediated by NO2 lead to generation of trans-arachidonic acid isomers, including biologically active 14-trans-eicosatetraenoic acid, within membrane phospholipids from which they can be released and excreted into urine.
Biological nitration of arachidonic acid.
TLDR
The products of fatty acid nitration have the potential to function as biomarkers and/or lipid mediators of mechanisms distinct from fatty acid peroxidation but offering insight into the contribution of specific RNS such as NO2 to the damage of biological membrane resulting from nitrooxidative stress.
Nitration of unsaturated fatty acids by nitric oxide-derived reactive nitrogen species peroxynitrite, nitrous acid, nitrogen dioxide, and nitronium ion.
TLDR
Since unsaturated lipids of membranes and lipoproteins are critical targets of reactive oxygen and nitrogen species, these pathways lend insight into mechanisms for the formation of novel nitrogen-containing lipid products in vivo and provide synthetic strategies for further structural and functional studies.
Chemistry of nitrated lipids: remarkable instability of 9-nitrolinoleic acid in neutral aqueous medium and a novel nitronitrate ester product by concurrent autoxidation/nitric oxide-release pathways.
TLDR
The markedly different stability of isomeric nitrolinoleic acids disclosed in the present study may provide an explanation for the previous identification of 2, but not 1, in body fluids and offers a key for future insights into the biological activities of nitrated lipids.
...
...