Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes

Esterbauer, Hermann; Schaur, Rudolf Jörg; Zollner, Helmward

doi:10.1016/0891-5849(91)90192-6

Cited by 6,672Antioxidant Activity and Oxidative StressRedox biology and oxidative stressCancer and biochemical research

Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes

Esterbauer, Hermann, Schaur, Rudolf Jörg, Zollner, Helmward·1991·Free Radical Biology and Medicine

DOI 10.1016/0891-5849(91)90192-6

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Abstract

Lipid peroxidation often occurs in response to oxidative stress, and a great diversity of aldehydes are formed when lipid hydroperoxides break down in biological systems. Some of these aldehydes are highly reactive and may be considered as second toxic messengers which disseminate and augment initial free radical events. The aldehydes most intensively studied so far are 4-hydroxynonenal, 4-hydroxyhexenal, and malonaldehyde. The purpose of this review is to provide a comprehensive summary on the chemical properties of these aldehydes, the mechanisms of their formation and their occurrence in biological systems and methods for their determination. We will also review the reactions of 4-hydroxyalkenals and malonaldehyde with biomolecules (amino acids, proteins, nucleic acid bases), their metabolism in isolated cells and excretion in whole animals, as well as the many types of biological activities described so far, including cytotoxicity, genotoxicity, chemotactic activity, and effects on cell proliferation and gene expression. Structurally related compounds, such as acrolein, crotonaldehyde, and other 2-alkenals are also briefly discussed, since they have some properties in common with 4-hydroxyalkenals.

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These indirect effects include up- or down-regulation of resistin, leptin, adiponectin, lipocalin 2, osteopontin and insulin itself.
“These effects include the up-or down-regulation of the synthesis of resistin (138) , leptin, adiponectin (139) , lipocalin 2 (140) , osteopontin (141) , and of insulin itself.”
From Dietary factors and low-grade inflammation in relation to overweight and obesity (2011) · cites this paper as [139]
Direct assessment of MDA and 4-HNE is not very sensitive, since the major portion of these reactive aldehydes is attached to proteins or other biomolecules and should be released before analysis.
“The direct assessment of MDA and 4-HNE is not very sensitive, since the major portion of these reactive aldehydes is attached to proteins or other biomolecules and therefore before analysis, should be released, otherwise, they remain undetected (Esterbauer et al. 1991).”
From Reactive Oxygen Species, Toxicity, Oxidative Stress, and Antioxidants: Chronic Diseases and Aging (2023) · cites this paper as Esterbauer et al. 1991
Reactive aldehydes from lipid peroxidation have biologically active functions.
“Reactive aldehydes from lipid peroxidation have biological active functions [59].”
From NOX4 promotes ferroptosis of astrocytes by oxidative stress-induced lipid peroxidation via the impairment of mitochondrial metabolism in Alzheimer’s diseases (2021) · cites this paper as [59]

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L-type Ca2+ channels provide a major pathway for iron entry into cardiomyocytes in iron-overload cardiomyopathy
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SOD2 knockdown mouse model of early AMD
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Authors: Esterbauer, H., Schaur, R. J., & Zollner, H.
Affiliations: University of Graz (AT)
Corresponding author: Esterbauer, Hermann
Venue: Free Radical Biology and Medicine
Publisher: Elsevier BV
Published: 1991
Volume: 11
Issue: 1
Pages: 81-128
ISSN: 0891-5849 (ISSN-L)
DOI: 10.1016/0891-5849(91)90192-6
OpenAlex: W2057522312
Cited by: 6,672
References: 370
Citations by year: 2026: 109 · 2025: 116 · 2024: 119 · 2023: 159 · 2022: 156 · 2021: 217 · 2020: 221 · 2019: 210 · 2018: 192 · 2017: 198 · 2016: 224 · 2015: 243 · 2014: 257 · 2013: 261 · 2012: 290
FWCI: 6.17
Type: journal article
Language: en
Open access: closed
Licence: www.elsevier.com/tdm/userlicense/1.0/ (tdm)
www.elsevier.com/legal/tdmrep-license (tdm)
Locations: Free Radical Biology and Medicine (publishedVersion)
PubMed (publishedVersion)
Topics: Health Sciences › Medicine › Biochemistry › 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 › Molecular Biology › Cancer and biochemical research
Keywords: 4-hydroxynonenal, malondialdehyde, lipid peroxidation, lipid hydroperoxides, 4-hydroxyhexenal, 2-alkenals, acrolein, crotonaldehyde, oxidative stress, aldehyde determination, aldehyde metabolism, cytotoxicity, genotoxicity, chemotactic activity, cell proliferation, gene expression
MeSH terms: Aldehydes, Animals, Free Radicals, Humans, Malondialdehyde

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Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes

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