Characterization of linoleic acid nitration in human blood plasma by mass spectrometry
Abstract
Nitric oxide (*NO) is a pervasive free radical species that concentrates in lipophilic compartments to serve as a potent inhibitor of lipid and low-density lipoprotein oxidation processes. In this study, we synthesized, characterized, and detected nitrated derivatives of linoleic acid (18:2) in human blood plasma using high-pressure liquid chromatography coupled with electrospray ionization tandem mass spectrometry. While the reaction of nitronium tetrafluoroborate with 18:2 presented ions with a mass/charge (m/z) ratio of 324 in the negative ion mode, characteristic of nitrolinoleate (LNO(2)), the reaction of nitrite (NO(2)(-)) with linoleic acid hydroperoxide yielded nitrohydroxylinoleate (LNO(2)OH, m/z 340). Further analysis by MS/MS gave a major fragment at m/z 46, characteristic of a nitro group (-NO(2)) present in the parent ion. This was confirmed by using [(15)N]O(2), which gave products of m/z 325 and 341, that after fragmentation yielded a daughter ion at m/z 47. Moreover, a C-NO(2) structure was also demonstrated in LNO(2)OH by nuclear magnetic resonance spectroscopy ((15)N NMR, delta 375.9), as well as by infrared analysis in both LNO(2)OH (nu(max) = 3427, 1553, and 1374 cm(-1)) and LNO(2) (nu(max) = 1552 and 1373 cm(-1)). 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. 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 *NO-derived species.
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Nitrated fatty acids have been detected both in animal tissues subjected to inflammatory conditions and endogenously in healthy human plasma and urine.
“Nitrated fatty acids have been detected both in animal tissues subjected to inflammatory conditions and endogenously in healthy human plasma and urine (25,38).”
From Conjugated linoleic acid is a preferential substrate for fatty acid nitration (2012) · cites this paper as [38]
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- Authors
- Lima, É. S., Di Mascio, P., Rubbo, H., & Abdalla, D. S. P.
- Affiliations
- Departamento de Análises Clínicas e Toxicológicas, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brazil, Departamento de Bioquímica, Instituto de Química Universidade de São Paulo, São Paulo, SP, Brazil, and Departamento de Bioquímica, Facultad de Medicina, Universidad de la República, Montevideo, Uruguay
- Universidade de São Paulo (BR)
- ORCID
- Rubbo, Homero
- Venue
- Biochemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2002-07-31
- Volume
- 41
- Issue
- 34
- Pages
- 10717-10722
- ISSN
- 0006-2960 (ISSN-L)
- 1520-4995
- OpenAlex
- W2002273238
- Cited by
- 103
- References
- 15
- Citations by year
- 2026: 1 · 2024: 4 · 2023: 2 · 2022: 1 · 2021: 3 · 2020: 3 · 2019: 7 · 2018: 4 · 2017: 2 · 2016: 4 · 2015: 5 · 2014: 4 · 2013: 5 · 2012: 4
- FWCI
- 2.89
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Biochemistry (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Chemistry › Spectroscopy › Mass Spectrometry Techniques and Applications
- Health Sciences › Medicine › Biochemistry › Antioxidant Activity and Oxidative Stress
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Metabolomics and Mass Spectrometry Studies
- Keywords
- nitric oxide, lipid oxidation, nitronium tetrafluoroborate, nitrite, linoleic acid hydroperoxide, hyperlipidemia, human plasma
- MeSH terms
- Female, Humans, Hydrogen-Ion Concentration, Male, Nitrogen, Mass Spectrometry, Time Factors, Linoleic Acid
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