Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes - PubMed (original) (raw)
Review
Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes
H Esterbauer et al. Free Radic Biol Med. 1991.
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.
Similar articles
- Lipid peroxidation and biogenic aldehydes: from the identification of 4-hydroxynonenal to further achievements in biopathology.
Comporti M. Comporti M. Free Radic Res. 1998 Jun;28(6):623-35. doi: 10.3109/10715769809065818. Free Radic Res. 1998. PMID: 9736314 Review. - Genotoxicity of lipid oxidation compounds.
Eckl PM, Bresgen N. Eckl PM, et al. Free Radic Biol Med. 2017 Oct;111:244-252. doi: 10.1016/j.freeradbiomed.2017.02.002. Epub 2017 Feb 5. Free Radic Biol Med. 2017. PMID: 28167130 Review. - Chemistry and analysis of HNE and other prominent carbonyl-containing lipid oxidation compounds.
Sousa BC, Pitt AR, Spickett CM. Sousa BC, et al. Free Radic Biol Med. 2017 Oct;111:294-308. doi: 10.1016/j.freeradbiomed.2017.02.003. Epub 2017 Feb 10. Free Radic Biol Med. 2017. PMID: 28192230 Review. - The reaction of 2-thiobarbituric acid with biologically active alpha,beta-unsaturated aldehydes.
Witz G, Lawrie NJ, Zaccaria A, Ferran HE Jr, Goldstein BD. Witz G, et al. J Free Radic Biol Med. 1986;2(1):33-9. doi: 10.1016/0748-5514(86)90121-2. J Free Radic Biol Med. 1986. PMID: 3772040 - Biological effect of protein modifications by lipid peroxidation products.
Gęgotek A, Skrzydlewska E. Gęgotek A, et al. Chem Phys Lipids. 2019 Jul;221:46-52. doi: 10.1016/j.chemphyslip.2019.03.011. Epub 2019 Mar 25. Chem Phys Lipids. 2019. PMID: 30922835 Review.
Cited by
- Reactive Oxygen Species: Angels and Demons in the Life of a Neuron.
Biswas K, Alexander K, Francis MM. Biswas K, et al. NeuroSci. 2022 Mar 16;3(1):130-145. doi: 10.3390/neurosci3010011. eCollection 2022 Mar. NeuroSci. 2022. PMID: 39484669 Free PMC article. Review. - A maternal low-protein diet results in sex-specific differences in synaptophysin expression and milk fatty acid profiles in neonatal rats.
Bello-Medina PC, Díaz-Muñoz M, Martín Del Campo ST, Pacheco-Moisés FP, Flores Miguel C, Cobián Cervantes R, García Solano PB, Navarro-Meza M. Bello-Medina PC, et al. J Nutr Sci. 2024 Oct 14;13:e64. doi: 10.1017/jns.2024.46. eCollection 2024. J Nutr Sci. 2024. PMID: 39469193 Free PMC article. - Aberrant Lipid Metabolism and Complement Activation in Age-Related Macular Degeneration.
Tang S, Yang J, Xiao B, Wang Y, Lei Y, Lai D, Qiu Q. Tang S, et al. Invest Ophthalmol Vis Sci. 2024 Oct 1;65(12):20. doi: 10.1167/iovs.65.12.20. Invest Ophthalmol Vis Sci. 2024. PMID: 39405051 Free PMC article. Review. - Aldehyde-induced DNA-protein crosslinks- DNA damage, repair and mutagenesis.
Blouin T, Saini N. Blouin T, et al. Front Oncol. 2024 Sep 12;14:1478373. doi: 10.3389/fonc.2024.1478373. eCollection 2024. Front Oncol. 2024. PMID: 39328207 Free PMC article. Review.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources