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

The DOI matches its Crossref record; 370 of the 370 references it cites were found in a registry or an index.

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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Citations

Cites

Research works printed but not linked: 25

  1. Esterbauer, 1988, Hydroxyalkenals: cytotoxic products of lipid peroxidation, ISI Atlas of Science, 1, 311
  2. Ramenghi, 1985, Increased production of carbonyls other than malonaldehyde in red blood cells from homocygous thalassemic subjects exposed to oxidative stress, IRCS Med. Sci., 13, 273
  3. Curzio, 1986, Detection of carbonyl products of lipid peroxidation in rat pleural exudate, IRCS Med. Sci., 14, 984
  4. Sodum, 1987, Formation of 1,N2-ethenodeoxyguanosine and propano-deoxyguanosine adducts with trans-4-hydroxy-2-nonenal, Carcinogenesis, 28, 98
  5. Eckl, 1989, Genotoxic effects of 4-hydroxynonenals, Adv. Biosci., 76, 141
  6. Cajelli, 1984, Mutagenicity of 4-hydroxynonenal in V79 Chinese hamster lung cells, Mutation Res., 44, 169
  7. Curzio, 1990, Influence of the lipid peroxidation product 4-hydroxynonenal on human neutrophil migration, Int. J. Tissue React., 6, 13
  8. Hofer, 1983, Some effects of 4-hydroxypentenal on the synchronous mitotic cycle of Physarum polycephalum, IRCS Med. Science, 11, 356
  9. Zollner, 1973, Effects of 4-hydroxypentenal on succinate respiration and succinate dehydrogenase in liver and tumor cells, Z. Krebsforsch., 79, 108
  10. Koster, 1986, Comparison of the inactivation of microsomal glucose-6-phosphatase by in situ lipid peroxidation-derived 4-hydroxynonenal and exogenous 4-hydroxynonenal, Free Radic. Res. Commun., 1, 273, 10.3109/10715768609051637 · DOI
  11. Claisen, 1903, On the knowledge about propagylaldehyde and phenyl propagylaldehyde, Berichte, 36, 3664
  12. Hüttel, 1941, On malonaldehyde, Berichte, 74, 1825
  13. Scherz, 1978, Über die bildung von malondialdehyd bei der bestrahlung von lebensmitteln, Chem. Mikrobiol. Technol. Lebensm., 1, 103
  14. Napetschnig, 1988, Formation of a pyridinium derivative by reaction of 4-hydroxypentenal with glycine, Chem. Biol. Interact., 68, 165, 10.1016/0009-2797(88)90014-2 · DOI
  15. Loeper, 1983, Study of fatty acids and lipid peroxidation during the course of human atherosclerosis, Sem. Hop. Paris, 59, 1657
  16. Janero, 1986, Isolation by HPLC of free malondialdehyde as a product of the xanthine-oxidase dependent, iron-promoted peroxidation of cardiac membrane phospholipid, J. Am. Oil Chem. Soc., 63, 476
  17. Jeny, 1986, Study of lipidperoxidation in human and experimental atheroma by measurement of plasma malonaldehyde, Presse Medicale, 15, 1131
  18. Mahanty, 1986, Aspirin stimulates malonaldehyde production in mouse-liver microsomes, Pediatric Res., 20, 651
  19. Skornyakov, 1988, Lipid peroxidation products in the cerebrospinal fluid of patients with craniocerebral injuries, Lab. Delo., 14
  20. Kergonou, 1988, Immunogenicity of proteins reacted with malonic dialdehyde (MDA), Adv. Biosci., 71, 121
  21. Esterbauer, H.; Schaur, R. J.; Zollner, H. Biological activities of 4-hydroxyalkenals. In: Sies, H., ed. Oxidative stress. New York: Academic Press; in press.
  22. Fisher, 1954, Depolymerization of desoxyribonucleic acid preparations by oxidized methyl linoleate, J. Eli. Mitchell Soc., 70, 124
  23. Akasaka, 1985, Mutation induction in Escherichia coli incubated in the reaction mixture of NADPH-dependent lipid peroxidation of rat-liver microsomes, Mutation Res., 149, 321, 10.1016/0027-5107(85)90147-2 · DOI
  24. Spalding, 1989, Toxicology and carinogenesis studies of malondialdehyde sodium salt (3-hydroxy-2-propenal, sodium salt) in F344/N rats and B6C3F1 mice, Natl. Toxicol. Program Ser., 331, 5
  25. Stone, 1990, Investigation of the adducts formed by reaction of malondialdehyde with adenosine, Chem. Res. Toxicol., 3, 33, 10.1021/tx00013a006 · DOI

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Metadata

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
Locations
  • Free Radical Biology and Medicine (publishedVersion)
  • PubMed (publishedVersion)
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 › 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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