Cited by 294Antioxidant Activity and Oxidative StressRedox biology and oxidative stressParaoxonase enzyme and polymorphisms

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Quantification of malondialdehyde and 4-hydroxynonenal adducts to lysine residues in native and oxidized human low-density lipoprotein

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REQUENA, Jesús R., FU, Min Xin, AHMED, Mahtab U., JENKINS, Alicia J., LYONS, Timothy J., BAYNES, John W., THORPE, Suzanne R.·1997·Biochemical Journal

DOI 10.1042/bj3220317PMC PMC1218194

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Abstract

Malondialdehyde (MDA) and 4-hydroxynonenal (HNE) are major end-products of oxidation of polyunsaturated fatty acids, and are frequently measured as indicators of lipid peroxidation and oxidative stress in vivo. MDA forms Schiff-base adducts with lysine residues and cross-links proteins in vitro; HNE also reacts with lysines, primarily via a Michael addition reaction. We have developed methods using NaBH4 reduction to stabilize these adducts to conditions used for acid hydrolysis of protein, and have prepared reduced forms of lysine-MDA [3-(Nε-lysino)propan-1-ol (LM)], the lysine-MDA-lysine iminopropene cross-link [1,3-di(Nε-lysino)propane (LML)] and lysine-HNE [3-(Nε-lysino)-4-hydroxynonan-1-ol (LHNE)]. Gas chromatography/MS assays have been developed for quantification of the reduced compounds in protein. RNase incubated with MDA or HNE was used as a model for quantification of the adducts by gas chromatography/MS. There was excellent agreement between measurement of MDA bound to RNase as LM and LML, and as thiobarbituric acid-MDA adducts measured by HPLC; these adducts accounted for 70Ő80% of total lysine loss during the reaction with MDA. LM and LML (0.002Ő0.12mmol/mol of lysine) were also found in freshly isolated low-density lipoprotein (LDL) from healthy subjects. LHNE was measured in RNase treated with HNE, but was not detectable in native LDL. LM, LML and LHNE increased in concert with the formation of conjugated dienes during the copper-catalysed oxidation of LDL, but accounted for modification of < 1% of lysine residues in oxidized LDL. These results are the first report of direct chemical measurement of MDA and HNE adducts to lysine residues in LDL. LM, LML and LHNE should be useful as biomarkers of lipid peroxidative modification of protein and of oxidative stress in vitro and in vivo.

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Authors: REQUENA, J. R., FU, M. X., AHMED, M. U., JENKINS, A. J., LYONS, T. J., BAYNES, J. W., & THORPE, S. R.
Affiliations: University of South Carolina (US)
Medical University of South Carolina (US)
ORCID: JENKINS, Alicia J.
LYONS, Timothy J.
Venue: Biochemical Journal
Publisher: Portland Press Ltd.
Published: 1997-02-15
Volume: 322
Issue: 1
Pages: 317-325
ISSN: 0264-6021 (ISSN-L)
1470-8728
DOI: 10.1042/bj3220317
PMC: PMC1218194
OpenAlex: W1843398852
Cited by: 293
References: 35
Citations by year: 2026: 4 · 2025: 3 · 2024: 3 · 2023: 13 · 2022: 7 · 2021: 6 · 2020: 7 · 2019: 2 · 2018: 5 · 2017: 9 · 2016: 6 · 2015: 5 · 2014: 7 · 2013: 11 · 2012: 14
FWCI: 10.07
Type: journal article
Language: en
Open access: bronze
doi.org
Locations: Biochemical Journal (publishedVersion)
PubMed Central (publishedVersion)
PubMed (publishedVersion)
Scholar Commons (University of South Carolina) (submittedVersion)
Research Portal (Queen's University Belfast) (submittedVersion)
Funders: National Institutes of Health (5r01ag011472-04)
National Institute on Aging (AG-11472)
National Eye Institute (5R29 EY10697, R29EY010697)
Topics: Health Sciences › Medicine › Biochemistry (medical) › Antioxidant Activity and Oxidative Stress
Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
Life Sciences › Biochemistry, Genetics and Molecular Biology › Clinical Biochemistry › Paraoxonase enzyme and polymorphisms
Keywords: malondialdehyde, 4-hydroxynonenal, lipid peroxidation, lysine adducts, low-density lipoprotein, protein oxidation, Schiff base adducts, Michael addition, sodium borohydride reduction, oxidative stress biomarkers, conjugated dienes, protein cross-linking
MeSH terms: Aldehydes, Amino Acids, Collagen, Copper, Crystallins, Drug Stability, Humans, Lipoproteins, LDL, Lysine, Malondialdehyde, Gas Chromatography-Mass Spectrometry, Oxidation-Reduction, Ribonucleases, Schiff Bases, Skin, Lipid Peroxidation

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Quantification of malondialdehyde and 4-hydroxynonenal adducts to lysine residues in native and oxidized human low-density lipoprotein

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