CHEMISTRY AND BIOCHEMISTRY OF 4-HYDROXYNONENAL, MALONALDEHYDE AND RELATED ALDEHYDES

被引：5745
作者：
ESTERBAUER, H
SCHAUR, RJ
ZOLLNER, H
机构：
[1] Institute of Biochemistry, University of Graz, A-8010 Graz
来源：
FREE RADICAL BIOLOGY AND MEDICINE | 1991年 / 11卷 / 01期
关键词：
4-HYDROXYNONENAL; 4-HYDROXYHEXENAL; MALONALDEHYDE; ACROLEIN; LIPID PEROXIDATION; FREE RADICALS; BIOLOGICAL EFFECTS;
D O I：
10.1016/0891-5849(91)90192-6
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
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.
引用
收藏
页码：81 / 128
页数：48
相关论文
共 183 条
[81]  
Sodum, Chung, Formation of 1,N<sup>2</sup>-ethenodeoxyguanosine and propano-deoxyguanosine adducts with trans-4-hydroxy-2-nonenal, Carcinogenesis, 28, (1987)
[82]  
Schauenstein, Taufer, Esterbauer, Kylianek, Seelich, The reaction of protein-SH-groups with 4-hydroxy-pentenal, Monatsh. Chem., 102, pp. 517-529, (1971)
[83]  
Rosenfeld, Palinski, Yla-Herttuala, Butler, Witztum, Distribution of oxidation specific lipid-protein adducts and apolipoprotein B in atherosclerotic lesions of varying severity from WHHL rabbits, Arteriosclerosis, 10, pp. 336-349, (1990)
[84]  
Haberland, Fong, Cheng, Malondialdehyde-altered protein occurs in atheroma of Watanabe heritable hyperlipidemic rabbits, Science, 241, pp. 215-218, (1988)
[85]  
Palinski, Rosenfeld, Yla-Herttuala, Gurtner, Socher, Butler, Parthasarathy, Carew, Steinberg, Witztum, Low density lipoprotein undergoes oxidative modification in vivo, Proc. Natl. Acad. Sci. USA, 86, pp. 1372-1376, (1989)
[86]  
Kikugawa, Beppu, Involvement of lipid oxidation products in the formation of fluorescent and cross-linked proteins, Chem. Phys. Lipids, 44, pp. 277-296, (1987)
[87]  
Tsuchida, Miura, Aibara, Lipofuscin and lipofuscin-like substances, Chem. Phys. Lipids, 44, pp. 297-325, (1987)
[88]  
Nair, Offerman, Ring-extended products from the reaction of epoxy carbonyl compounds and nucleic acid bases, J. Org. Chem., 50, pp. 5627-5631, (1985)
[89]  
Goldschmidt, Blazej, Van Duuren, The reaction of guanosine and deoxyguanosine with glycidaldehyde, Tetrahedron Lett., 13, pp. 1583-1585, (1968)
[90]  
Schauenstein, Effects of low concentrations of aldehydes on tumour cells and tumor growth, Free radicals, lipid peroxidation and cancer, pp. 159-171, (1982)
45678910111213