Trans-4-hydroxy-2-hexenal, a product of n-3 fatty acid peroxidation: make some room HNE. - PubMed (original) (raw)
Review
Trans-4-hydroxy-2-hexenal, a product of n-3 fatty acid peroxidation: make some room HNE.
Eric K Long et al. Free Radic Biol Med. 2010.
Abstract
Lipid peroxidation yields multiple aldehyde species. Of these, trans-4-hydroxy-2-nonenal (HNE), derived from n-6 poly-unsaturated fatty acids (PUFA) is one of the most studied products of lipid peroxidation. On the other hand, oxidative damage to n-3 PUFA, e.g. docosahexaenoic acid (DHA; 22:6, n-3) and eicosapentaenoic acid, is now recognized as an important effector of oxidative stress and is of particular interest in n-3 rich tissues such as brain and retina. Trans-4-hydroxy-2-hexenal (HHE) is a major alpha,beta-unsaturated aldehyde product of n-3 PUFA oxidation and, like HNE, is an active biochemical mediator resulting from lipid peroxidation. HHE adducts are elevated in disease states, in some cases, at higher levels than the corresponding HNE adduct. HHE has properties in common with HNE, but there are important differences particularly with respect to adduction targets and detoxification pathways. In this review, the biochemistry and cell biology of HHE will be discussed. From this review, it is clear that further study is needed to determine the biochemical and physiological roles of HHE and its related aldehyde, trans-4-oxo-2-hexenal.
(c) 2010. Published by Elsevier Inc.
Similar articles
- Trans-4-hydroxy-2-hexenal is a neurotoxic product of docosahexaenoic (22:6; n-3) acid oxidation.
Long EK, Murphy TC, Leiphon LJ, Watt J, Morrow JD, Milne GL, Howard JR, Picklo MJ Sr. Long EK, et al. J Neurochem. 2008 May;105(3):714-24. doi: 10.1111/j.1471-4159.2007.05175.x. Epub 2008 Jan 8. J Neurochem. 2008. PMID: 18194211 - Formation of malondialdehyde (MDA), 4-hydroxy-2-hexenal (HHE) and 4-hydroxy-2-nonenal (HNE) in fish and fish oil during dynamic gastrointestinal in vitro digestion.
Larsson K, Harrysson H, Havenaar R, Alminger M, Undeland I. Larsson K, et al. Food Funct. 2016 Feb;7(2):1176-87. doi: 10.1039/c5fo01401h. Food Funct. 2016. PMID: 26824872 - High-fat diet induces changes in adipose tissue trans-4-oxo-2-nonenal and trans-4-hydroxy-2-nonenal levels in a depot-specific manner.
Long EK, Olson DM, Bernlohr DA. Long EK, et al. Free Radic Biol Med. 2013 Oct;63:390-8. doi: 10.1016/j.freeradbiomed.2013.05.030. Epub 2013 May 28. Free Radic Biol Med. 2013. PMID: 23726997 Free PMC article. - Lipid peroxidation of membrane phospholipids generates hydroxy-alkenals and oxidized phospholipids active in physiological and/or pathological conditions.
Catalá A. Catalá A. Chem Phys Lipids. 2009 Jan;157(1):1-11. doi: 10.1016/j.chemphyslip.2008.09.004. Epub 2008 Oct 14. Chem Phys Lipids. 2009. PMID: 18977338 Review. - Signaling and cytotoxic functions of 4-hydroxyalkenals.
Riahi Y, Cohen G, Shamni O, Sasson S. Riahi Y, et al. Am J Physiol Endocrinol Metab. 2010 Dec;299(6):E879-86. doi: 10.1152/ajpendo.00508.2010. Epub 2010 Sep 21. Am J Physiol Endocrinol Metab. 2010. PMID: 20858748 Review.
Cited by
- Effects of water-soluble mangosteen extract on cognitive function and neuropsychiatric symptoms in patients with mild to moderate Alzheimer's disease (WECAN-AD): A randomized controlled trial.
Muangpaisan W, Wiputhanuphongs P, Jaisupa N, Junnu S, Samer J, Moongkarndi P, Supapueng O, Chalermsri C, Neungton N. Muangpaisan W, et al. Alzheimers Dement (N Y). 2022 Apr 5;8(1):e12292. doi: 10.1002/trc2.12292. eCollection 2022. Alzheimers Dement (N Y). 2022. PMID: 35415207 Free PMC article. - Dietary docosahexaenoic Acid (22:6) incorporates into cardiolipin at the expense of linoleic Acid (18:2): analysis and potential implications.
Cortie CH, Else PL. Cortie CH, et al. Int J Mol Sci. 2012 Nov 21;13(11):15447-63. doi: 10.3390/ijms131115447. Int J Mol Sci. 2012. PMID: 23203135 Free PMC article. Review. - 4-Oxo-(E)-2-hexenal produced by Heteroptera induces permanent locomotive impairment in crickets that correlates with free thiol depletion.
Noge K, Becerra JX. Noge K, et al. FEBS Open Bio. 2015 Apr 14;5:319-24. doi: 10.1016/j.fob.2015.04.004. eCollection 2015. FEBS Open Bio. 2015. PMID: 25941628 Free PMC article. - Deuterated polyunsaturated fatty acids reduce brain lipid peroxidation and hippocampal amyloid β-peptide levels, without discernable behavioral effects in an APP/PS1 mutant transgenic mouse model of Alzheimer's disease.
Raefsky SM, Furman R, Milne G, Pollock E, Axelsen P, Mattson MP, Shchepinov MS. Raefsky SM, et al. Neurobiol Aging. 2018 Jun;66:165-176. doi: 10.1016/j.neurobiolaging.2018.02.024. Epub 2018 Mar 5. Neurobiol Aging. 2018. PMID: 29579687 Free PMC article. - Docosahexaenoic acid (DHA): An essential nutrient and a nutraceutical for brain health and diseases.
Sun GY, Simonyi A, Fritsche KL, Chuang DY, Hannink M, Gu Z, Greenlief CM, Yao JK, Lee JC, Beversdorf DQ. Sun GY, et al. Prostaglandins Leukot Essent Fatty Acids. 2018 Sep;136:3-13. doi: 10.1016/j.plefa.2017.03.006. Epub 2017 Mar 10. Prostaglandins Leukot Essent Fatty Acids. 2018. PMID: 28314621 Free PMC article. Review.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources