Two Distinct Pathways of Formation of 4-Hydroxynonenal
Open accessAbstract
The mechanism of formation of 4-hydroxy-2E-nonenal (4-HNE) has been a matter of debate since it was discovered as a major cytotoxic product of lipid peroxidation in 1980. Recent evidence points to 4-hydroperoxy-2E-nonenal (4-HPNE) as the immediate precursor of 4-HNE (Lee, S. H., and Blair, I. A. (2000) Chem. Res. Toxicol. 13, 698-702; Noordermeer, M. A., Feussner, I., Kolbe, A., Veldink, G. A., and Vliegenthart, J. F. G. (2000) Biochem. Biophys. Res. Commun. 277, 112-116), and a pathway via 9-hydroperoxylinoleic acid and 3Z-nonenal is recognized in plant extracts. Using the 9- and 13-hydroperoxides of linoleic acid as starting material, we find that two distinct mechanisms lead to the formation of 4-H(P)NE and the corresponding 4-hydro(pero)xyalkenal that retains the original carboxyl group (9-hydroperoxy-12-oxo-10E-dodecenoic acid). Chiral analysis revealed that 4-HPNE formed from 13S-hydroperoxy-9Z,11E-octadecadienoic acid (13S-HPODE) retains >90% S configuration, whereas it is nearly racemic from 9S-hydroperoxy-10E,12Z-octadecadienoic acid (9S-HPODE). 9-Hydroperoxy-12-oxo-10E-dodecenoic acid is >90% S when derived from 9S-HPODE and almost racemic from 13S-HPODE. Through analysis of intermediates and products, we provide evidence that (i) allylic hydrogen abstraction at C-8 of 13S-HPODE leads to a 10,13-dihydroperoxide that undergoes cleavage between C-9 and C-10 to give 4S-HPNE, whereas direct Hock cleavage of the 13S-HPODE gives 12-oxo-9Z-dodecenoic acid, which oxygenates to racemic 9-hydroperoxy-12-oxo-10E-dodecenoic acid; by contrast, (ii) 9S-HPODE cleaves directly to 3Z-nonenal as a precursor of racemic 4-HPNE, whereas allylic hydrogen abstraction at C-14 and oxygenation to a 9,12-dihydroperoxide leads to chiral 9S-hydroperoxy-12-oxo-10E-dodecenoic acid. Our results distinguish two major pathways to the formation of 4-HNE that should apply also to other fatty acid hydroperoxides. Slight ( approximately 10%) differences in the observed chiralities from those predicted in the above mechanisms suggest the existence of additional routes to the 4-hydroxyalkenals.
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The abundant diffusible products of lipid peroxidation are chemically reactive aldehydes including malondialdehyde (MDA), acrolein, 4-hydroxy-2-hexenal (4-HHE), and 4-hydroxy-2-nonenal (4-HNE).
“The abundant diffusible products of lipid peroxidation are chemically reactive aldehydes including malondialdehyde (MDA), acrolein, 4-hydroxy-2-hexenal (4-HHE), and 4-hydroxy-2-nonenal (4-HNE) [57,58].”
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Cites
Spectrometric Identification of Organic Compounds
Silverstein, R. M., & Bassler, G. C. (1962) · Journal of Chemical Education · doi:10.1021/ed039p546 · Cited by 14,272 · see citing works
Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes
Esterbauer, H., Schaur, R. J., & Zollner, H. (1991) · Free Radical Biology and Medicine · doi:10.1016/0891-5849(91)90192-6 · Cited by 6,672 · see citing works
Mechanisms of free radical oxidation of unsaturated lipids
Porter, N. A., Caldwell, S. E., & Mills, K. A. (1995) · Lipids · doi:10.1007/bf02536034 · Cited by 1,208 · see citing works
Self-citationBenedetti, A., Comporti, M., & Esterbauer, H. (1980) · Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism · doi:10.1016/0005-2760(80)90209-x · Cited by 1,085 · see citing works
Oxidative Alterations in Alzheimer's Disease
Markesbery, W. R., & Carney, J. M. (1999) · Brain Pathology · doi:10.1111/j.1750-3639.1999.tb00215.x · Cited by 789 · see citing works
The biogeneration of green odour by green leaves
Hatanaka, A. (1993) · Phytochemistry · doi:10.1016/0031-9422(91)80003-j · Cited by 643 · see citing works
The reaction of singlet oxygen with olefins: the question of mechanism
Frimer, A. A. (1979) · Chemical Reviews · doi:10.1021/cr60321a001 · Cited by 509 · see citing works
Porter, N. A., Weber, B. A., Weenen, H., & Khan, J. A. (1980) · Journal of the American Chemical Society · doi:10.1021/ja00537a032 · Cited by 245 · see citing works
Self-citationCharacterization of 4-Oxo-2-nonenal as a Novel Product of Lipid Peroxidation
Lee, S. H., & Blair, I. A. (2000) · Chemical Research in Toxicology · doi:10.1021/tx000101a · Cited by 244 · see citing works
Pryor, W. A., & Porter, N. A. (1990) · Free Radical Biology and Medicine · doi:10.1016/0891-5849(90)90153-a · Cited by 230 · see citing works
Self-citationKeller, J. N., & Mattson, M. P. (1998) · Reviews in the Neurosciences · doi:10.1515/revneuro.1998.9.2.105 · Cited by 217 · see citing works
Etheno DNA-base adducts from endogenous reactive species
Nair, J., Barbin, A., Velic, I., & Bartsch, H. (1999) · Mutation research. Fundamental and molecular mechanisms of mutagenesis · doi:10.1016/s0027-5107(99)00008-1 · Cited by 210 · see citing works
The Unexpected Role of Vitamin E (α-Tocopherol) in the Peroxidation of Human Low-Density Lipoprotein
Bowry, V. W., & Ingold, K. U. (1998) · Accounts of Chemical Research · doi:10.1021/ar950059o · Cited by 206 · see citing works
Studies on the mechanism of formation of 4-hydroxynonenal during microsomal lipid peroxidation
Esterbauer, H., Benedetti, A., Lång, J., Fulceri, R., Fauler, G., & Comporti, M. (1986) · Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism · doi:10.1016/0005-2760(86)90329-2 · Cited by 171 · see citing works
Matthew, J. A., Chan, H. W.-S., & GALLIARD, T. (1977) · Lipids · doi:10.1007/bf02533358 · Cited by 144 · see citing works
Havrilla, C. M., Hachey, D. L., & Porter, N. A. (2000) · Journal of the American Chemical Society · doi:10.1021/ja001180f · Cited by 118 · see citing works
Self-citationComportl, M. (1998) · Free Radical Research · doi:10.3109/10715769809065818 · Cited by 109 · see citing works
Tijet, N., Schneider, C. G., Muller, B. L., & BRASH, A. R. (2001) · Archives of Biochemistry and Biophysics · doi:10.1006/abbi.2000.2218 · Cited by 101 · see citing works
Self-citationGardner, H. W., & Plattner, R. D. (1984) · Lipids · doi:10.1007/bf02534458 · Cited by 92 · see citing works
Evidence for aldehydes bound to liver microsomal protein following CCl4 or BrCCl3 poisoning
Benedetti, A., Esterbauer, H., Ferrali, M., Fulceri, R., & Comporti, M. (1982) · Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism · doi:10.1016/0005-2760(82)90044-3 · Cited by 86 · see citing works
Oxygenation of (3Z)-nonenal to (2E)-4-hydroxy-2-nonenal in the broad bean (Vicia faba L.).
Gardner, H. W., & Hámberg, M. (1993) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)53134-3 · Cited by 78 · see citing works
Autoxidation of methyl linoleate: Identification of the bis‐allylic 11‐hydroperoxide
BRASH, A. R. (2000) · Lipids · doi:10.1007/s11745-000-0604-0 · Cited by 74 · see citing works
Self-citationCharacterization of HETEs and related conjugated dienes by UV spectroscopy
Ingram, C. D., & BRASH, A. R. (1988) · Lipids · doi:10.1007/bf02537345 · Cited by 53 · see citing works
Self-citationSoybean Lipoxygenase-1 Oxidizes 3Z-Nonenal
Gardner, H. W., & Grove, M. J. (1998) · PLANT PHYSIOLOGY · doi:10.1104/pp.116.4.1359 · Cited by 44 · see citing works
Fazio, V. M., Rinaldi, M., Ciafrè, S. A., Barrera, G., & Farace, M. G. (1993) · Molecular Aspects of Medicine · doi:10.1016/0098-2997(93)90008-2 · Cited by 38 · see citing works
Oxygenation of (3Z)-Alkenals to 4-Hydroxy-(2E)-Alkenals in Plant Extracts: A Nonenzymatic Process
Noordermeer, M. A., Feußner, I., Kolbe, A., Veldink, G. A., & Vliegenthart, J. F. G. (2000) · Biochemical and Biophysical Research Communications · doi:10.1006/bbrc.2000.3641 · Cited by 36 · see citing works
A novel transformation of 13-ls-hydroperoxy-9, 11-octadecadienoicacid
Hámberg, M. (1983) · Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism · doi:10.1016/0005-2760(83)90112-1 · Cited by 34 · see citing works
9‐Hydroxy‐traumatin, a new metabolite of the lipoxygenase pathway
Gardner, H. W. (1998) · Lipids · doi:10.1007/s11745-998-0265-z · Cited by 30 · see citing works
Corey, E. J., & Nagata, R. (1987) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)96736-4 · Cited by 27 · see citing works
Brown, H. C., Chen, G.-M., & Ramachandran, P. V. (1997) · Chirality · doi:10.1002/(sici)1520-636x(1997)9:5/6 · Cited by 12 · see citing works
Self-citation
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Ayala, A., Muñoz, M., & Argüelles, S. (2014) · Oxidative Medicine and Cellular Longevity · doi:10.1155/2014/360438 · Cited by 6,557 · see citing works
Role of Oxidative Modifications in Atherosclerosis
Stocker, R., & Keaney, J. F. (2004) · Physiological Reviews · doi:10.1152/physrev.00047.2003 · Cited by 2,611 · see citing works
Free Radical Lipid Peroxidation: Mechanisms and Analysis
Yin, H., Xu, L., & Porter, N. A. (2011) · Chemical Reviews · doi:10.1021/cr200084z · Cited by 1,952 · see citing works
Self-citationLipid peroxidation in cell death
Gaschler, M. M., & Stockwell, B. R. (2017) · Biochemical and Biophysical Research Communications · doi:10.1016/j.bbrc.2016.10.086 · Cited by 1,852 · see citing works
Feußner, I., & Wasternack, C. H. (2002) · Annual Review of Plant Biology · doi:10.1146/annurev.arplant.53.100301.135248 · Cited by 1,510 · see citing works
4-Hydroxy-2-nonenal: a product and mediator of oxidative stress
Uchida, K. (2003) · Progress in Lipid Research · doi:10.1016/s0163-7827(03)00014-6 · Cited by 1,164 · see citing works
Acrolein: Sources, metabolism, and biomolecular interactions relevant to human health and disease
Stevens, J. F., & Maier, C. S. (2008) · Molecular Nutrition & Food Research · doi:10.1002/mnfr.200700412 · Cited by 756 · see citing works
Aldehyde Sources, Metabolism, Molecular Toxicity Mechanisms, and Possible Effects on Human Health
O'Brien, P. J., Siraki, A. G., & Shangari, N. (2005) · Critical Reviews in Toxicology · doi:10.1080/10408440591002183 · Cited by 738 · see citing works
Park, M. W., Cha, H. W., Kim, J., Kim, J. H., Yang, H., Yoon, S., Boonpraman, N., Yi, S. S., Yoo, I. D., & Moon, J.-S. (2021) · Redox Biology · doi:10.1016/j.redox.2021.101947 · Cited by 683 · see citing works
Oxidative Stress and Covalent Modification of Protein with Bioactive Aldehydes
Grimsrud, P. A., Xie, H., Griffin, T. J., & Bernlohr, D. (2008) · Journal of Biological Chemistry · doi:10.1074/jbc.r700019200 · Cited by 570 · see citing works
Chemistry and biochemistry of lipid peroxidation products
Guéraud, F., Atalay, M., Bresgen, N., Gašparović, A. Č., Eckl, P., Laurence Therese, H. U. C., Jouanin, I., Siems, W., & Uchida, K. (2010) · Free Radical Research · doi:10.3109/10715762.2010.498477 · Cited by 556 · see citing works
Role of lipid peroxidation derived 4-hydroxynonenal (4-HNE) in cancer: Focusing on mitochondria
Zhong, H., & Yin, H. (2014) · Redox Biology · doi:10.1016/j.redox.2014.12.011 · Cited by 540 · see citing works
The Role of Oxidative Stress in Diabetic Complications
Niedowicz, D. M., & Daleke, D. L. (2005) · Cell Biochemistry and Biophysics · doi:10.1385/cbb:43:2:289 · Cited by 528 · see citing works
Montine, T. J., Neely, M. D., Quinn, J. F., Beal, M. F., Markesbery, W. R., Roberts, L. J., & Morrow, J. D. (2002) · Free Radical Biology and Medicine · doi:10.1016/s0891-5849(02)00807-9 · Cited by 449 · see citing works
Bogeat‐Triboulot, M., Brosché, M., Renaut, J., Jouve, L., Thiec, D. L., Fayyaz, P., Vinocur, B., Witters, E., Laukens, K., Teichmann, T., et al. (2006) · PLANT PHYSIOLOGY · doi:10.1104/pp.106.088708 · Cited by 414 · see citing works
Reactions of 4-hydroxynonenal with proteins and cellular targets
Petersen, D. R., & Doorn, J. A. (2004) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2004.06.012 · Cited by 393 · see citing works
Chemical alterations taken place during deep-fat frying based on certain reaction products: A review
Zhang, Q. R., Saleh, A. S. M., Chen, J., & Shen, Q. (2012) · Chemistry and Physics of Lipids · doi:10.1016/j.chemphyslip.2012.07.002 · Cited by 378 · see citing works
Mitochondrial uncoupling proteins—What is their physiological role?
Echtay, K. S. (2007) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2007.08.011 · Cited by 338 · see citing works
Basic aspects of the biochemical reactivity of 4-hydroxynonenal
Schaur, R. J. (2003) · Molecular Aspects of Medicine · doi:10.1016/s0098-2997(03)00009-8 · Cited by 341 · see citing works
Intervention strategies to inhibit protein carbonylation by lipoxidation‐derived reactive carbonyls
Aldini, G., Dalle‐Donne, I., Facino, R. M., Milzani, A., & Carini, M. (2006) · Medicinal Research Reviews · doi:10.1002/med.20073 · Cited by 289 · see citing works
Routes to 4-Hydroxynonenal: Fundamental Issues in the Mechanisms of Lipid Peroxidation
Schneider, C. G., Porter, N. A., & BRASH, A. R. (2008) · Journal of Biological Chemistry · doi:10.1074/jbc.r800001200 · Cited by 275 · see citing works
Self-citationThe lipid peroxidation product 4-hydroxy-2-nonenal: Advances in chemistry and analysis
Spickett, C. M. (2013) · Redox Biology · doi:10.1016/j.redox.2013.01.007 · Cited by 269 · see citing works
4-Hydroxy-2-nonenal: a critical target in oxidative stress?
Breitzig, M., Bhimineni, C., Lockey, R. F., & Kolliputi, N. (2016) · American Journal of Physiology-Cell Physiology · doi:10.1152/ajpcell.00101.2016 · Cited by 284 · see citing works
Sawicki, R., Singh, S. P., Mondal, A. K., Beneš, H., & Zimniak, P. (2003) · Biochemical Journal · doi:10.1042/bj20021287 · Cited by 221 · see citing works
Antioxidants and HNE in redox homeostasis
Łuczaj, W., Gęgotek, A., & Skrzydlewska, E. (2016) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2016.11.033 · Cited by 197 · see citing works
Vila, A., Tallman, K. A., Jacobs, A. T., Liebler, D. C., Porter, N. A., & Marnett, L. J. (2008) · Chemical Research in Toxicology · doi:10.1021/tx700347w · Cited by 192 · see citing works
Self-citationToxic Oxygenated α,β-Unsaturated Aldehydes and their Study in Foods: A Review
Guillén, M. D., & Goicoechea, E. (2008) · Critical Reviews in Food Science and Nutrition · doi:10.1080/10408390601177613 · Cited by 188 · see citing works
Trans-4-hydroxy-2-hexenal, a product of n-3 fatty acid peroxidation: Make some room HNE…
Long, E. K., & Picklo, M. J. (2010) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2010.03.015 · Cited by 178 · see citing works
Carini, M., Aldini, G., & Facino, R. M. (2004) · Mass Spectrometry Reviews · doi:10.1002/mas.10076 · Cited by 176 · see citing works
New Insights Regarding the Autoxidation of Polyunsaturated Fatty Acids
Yin, H., & Porter, N. A. (2004) · Antioxidants and Redox Signaling · doi:10.1089/ars.2005.7.170 · Cited by 177 · see citing works
Self-citationChemistry and analysis of HNE and other prominent carbonyl-containing lipid oxidation compounds
Sousa, B. C., Pitt, A. R., & Spickett, C. M. (2017) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2017.02.003 · Cited by 172 · see citing works
Lipid Peroxidation: Kinetics, Mechanisms, and Products
Zielinski, Z. A. M., & Pratt, D. A. (2017) · The Journal of Organic Chemistry · doi:10.1021/acs.joc.7b00152 · Cited by 168 · see citing works
Effects of polyunsaturated fatty acids on hibernation and torpor: a review and hypothesis
Ruf, T., & Arnold, W. (2008) · American Journal of Physiology-Regulatory, Integrative and Comparative Physiology · doi:10.1152/ajpregu.00688.2007 · Cited by 166 · see citing works
Lipoxidation adducts with peptides and proteins: Deleterious modifications or signaling mechanisms?
Domingues, R. M., Domingues, P. M., Melo, T., Pérez‐Sala, D., Reis, A., & Spickett, C. M. (2013) · Journal of Proteomics · doi:10.1016/j.jprot.2013.06.004 · Cited by 165 · see citing works
Histidine and lysine as targets of oxidative modification
Uchida, K. (2003) · Amino Acids · doi:10.1007/s00726-003-0015-y · Cited by 164 · see citing works
Taylor, N. L., Tan, Y., Jacoby, R. P., & Millar, A. H. (2008) · Journal of Proteomics · doi:10.1016/j.jprot.2008.11.006 · Cited by 147 · see citing works
The lipoxygenase gene ALOXE3 implicated in skin differentiation encodes a hydroperoxide isomerase
Yu, Z., Schneider, C. G., Boeglin, W. E., Marnett, L. J., & BRASH, A. R. (2003) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1633612100 · Cited by 146 · see citing works
Self-citationMano, J., Torii, Y., Hayashi, S.-I., Takimoto, K., Matsui, K., Nakamura, K., Inzé, D., Babiychuk, E., Kushnir, S., & Asada, K. (2002) · Plant and Cell Physiology · doi:10.1093/pcp/pcf187 · Cited by 145 · see citing works
The role of vitamin E in atherosclerosis
Upston, J. M., Kritharides, L., & Stocker, R. (2003) · Progress in Lipid Research · doi:10.1016/s0163-7827(03)00024-9 · Cited by 145 · see citing works
Upston, J. M., Niu, X., Brown, A. J., Mashima, R., Wang, H., Senthilmohan, R., Kettle, A. J., Dean, R. T., & Stocker, R. (2002) · American Journal Of Pathology · doi:10.1016/s0002-9440(10)64890-0 · Cited by 143 · see citing works
Mano, J., Belles‐Boix, E., Babiychuk, E., Inzé, D., Torii, Y., Hiraoka, E., Takimoto, K., Slooten, L., Asada, K., & Kushnir, S. (2005) · PLANT PHYSIOLOGY · doi:10.1104/pp.105.070391 · Cited by 140 · see citing works
Proteomics of lipid oxidation‐induced oxidation of porcine and bovine oxymyoglobins
Suman, S. P., Faustman, C., Stamer, S. L., & Liebler, D. C. (2007) · PROTEOMICS · doi:10.1002/pmic.200600313 · Cited by 131 · see citing works
Damage of DNA and proteins by major lipid peroxidation products in genome stability
Winczura, A., Zdżalik-Bielecka, D., & Tudek, B. (2012) · Free Radical Research · doi:10.3109/10715762.2012.658516 · Cited by 127 · see citing works
Reiniers, M. J., van Golen, R. F., van Gulik, T. M., & Heger, M. (2013) · Antioxidants and Redox Signaling · doi:10.1089/ars.2013.5486 · Cited by 131 · see citing works
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Mano, J., Biswas, M. S., & Sugimoto, K. (2019) · Plants · doi:10.3390/plants8100391 · Cited by 126 · see citing works
Formation of oxylipins by CYP74 enzymes
Stumpe, M., & Feußner, I. (2006) · Phytochemistry Reviews · doi:10.1007/s11101-006-9038-9 · Cited by 126 · see citing works
Chew, P., Yuen, D. Y. C., Stefanovic, N., Pete, J., Coughlan, M. T., Jandeleit-Dahm, K. A. M., Thomas, M. C., Rosenfeldt, F., Cooper, M. E., & de Haan, J. B. (2010) · Diabetes · doi:10.2337/db10-0195 · Cited by 125 · see citing works
Milković, L., Žarković, N., Marušić, Z., Žarković, K., & Jaganjac, M. (2023) · Antioxidants · doi:10.3390/antiox12040856 · Cited by 124 · see citing works
Liu, W., Porter, N. A., Schneider, C. G., BRASH, A. R., & Yin, H. (2010) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2010.10.709 · Cited by 121 · see citing works
Self-citationTaylor, N. L. (2003) · Journal of Experimental Botany · doi:10.1093/jxb/erh001 · Cited by 119 · see citing works
Ohsawa, I., Nishimaki, K., Murakami, Y., Suzuki, Y., Ishikawa, M., & Ohta, S. (2008) · Journal of Neuroscience · doi:10.1523/jneurosci.4956-07.2008 · Cited by 117 · see citing works
Abdul, H. M., Rukhsana Sultana, A., Keller, J. N., Clair, D. K. S., Markesbery, W. R., & Butterfield, D. A. (2006) · Journal of Neurochemistry · doi:10.1111/j.1471-4159.2005.03647.x · Cited by 114 · see citing works
Zhu, Q. Y., Zheng, Z., Cheng, K., Wu, J., Zhang, S., Tang, Y. S., Sze, K. H., Chen, J., Chen, F., & Wang, M. (2009) · Chemical Research in Toxicology · doi:10.1021/tx900221s · Cited by 112 · see citing works
Porcia, L. C., Mella–Flores, D., Moenne, A., & Correa, J. A. (2009) · Aquatic Toxicology · doi:10.1016/j.aquatox.2009.06.004 · Cited by 111 · see citing works
Reconsider Alzheimer's disease by the ‘calpain–cathepsin hypothesis’—A perspective review
Yamashima, T. (2013) · Progress in Neurobiology · doi:10.1016/j.pneurobio.2013.02.004 · Cited by 107 · see citing works
Nishimaki, K., Asada, T., Ohsawa, I., Nakajima, E., Ikejima, C., Yokota, T., Kamimura, N., & Ohta, S. (2018) · Current Alzheimer Research · doi:10.2174/1567205014666171106145017 · Cited by 108 · see citing works
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Awasthi, S., Ansari, G. A. S., & Awasthi, S. (2005) · Methods in enzymology on CD-ROM/Methods in enzymology · doi:10.1016/s0076-6879(05)01024-4 · Cited by 108 · see citing works
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Murray, I. V. J., Liu, L., Komatsu, H., Uryu, K., Xiao, G., Lawson, J. A., & Axelsen, P. H. (2007) · Journal of Biological Chemistry · doi:10.1074/jbc.m608589200 · Cited by 106 · see citing works
Ayyadevara, S., Engle, M. R., Singh, S. P., Dandapat, A., Lichti, C. F., Beneš, H., Reis, R. J. S., Liebau, E., & Zimniak, P. (2005) · Aging Cell · doi:10.1111/j.1474-9726.2005.00168.x · Cited by 103 · see citing works
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Cao, W., Kayama, H., Chen, M. L., Delmas, A., Sun, A., Kim, S. Y., Rangarajan, E. S., McKevitt, K., Beck, A. P., Jackson, C. B., et al. (2017) · Immunity · doi:10.1016/j.immuni.2017.11.012 · Cited by 102 · see citing works
The Chemical Reactivity of Membrane Lipids
Duché, G., & Sanderson, J. M. (2024) · Chemical Reviews · doi:10.1021/acs.chemrev.3c00608 · Cited by 102 · see citing works
Cyclooxygenase-2-mediated DNA Damage
Lee, S. H., Williams, M. V., DuBois, R. N., & Blair, I. A. (2005) · Journal of Biological Chemistry · doi:10.1074/jbc.m504178200 · Cited by 102 · see citing works
Role of Lipid Peroxidation and PPAR-δ in Amplifying Glucose-Stimulated Insulin Secretion
Cohen, G., Riahi, Y., Shamni, O., Guichardant, M., Chatgilialoglu, C., Ferreri, C., Kaiser, N., & Sasson, S. (2011) · Diabetes · doi:10.2337/db11-0347 · Cited by 101 · see citing works
Hydroperoxide lyase and divinyl ether synthase
Grechkin, A. N. (2002) · Prostaglandins & Other Lipid Mediators · doi:10.1016/s0090-6980(02)00048-5 · Cited by 97 · see citing works
Trans‐4‐hydroxy‐2‐hexenal is a neurotoxic product of docosahexaenoic (22:6; n‐3) acid oxidation
Long, E. K., Murphy, T. C., Leiphon, L. J., Watt, J. A., Morrow, J. D., Milne, G. L., Howard, J. R. H., & Picklo, M. J. (2007) · Journal of Neurochemistry · doi:10.1111/j.1471-4159.2007.05175.x · Cited by 97 · see citing works
Onyango, A. N. (2016) · Oxidative Medicine and Cellular Longevity · doi:10.1155/2016/2398573 · Cited by 96 · see citing works
Boonpraman, N., Yoon, S., Kim, C. Y., Moon, J., & Yi, S. S. (2023) · Redox Biology · doi:10.1016/j.redox.2023.102698 · Cited by 95 · see citing works
Davoine, C., Falletti, O., Douki, T., Iacazio, G., Ennar, N., Montillet, J., & Triantaphylidès, C. (2006) · PLANT PHYSIOLOGY · doi:10.1104/pp.105.074690 · Cited by 94 · see citing works
Structural Basis of Protein-bound Endogenous Aldehydes
Hashimoto, M., Sibata, T., Wasada, H., Toyokuni, S., & Uchida, K. (2003) · Journal of Biological Chemistry · doi:10.1074/jbc.m210129200 · Cited by 88 · see citing works
Dang, Y., He, Q. H., Yang, S., Sun, H., Liu, Y., Li, W., Tang, Y., Zheng, Y., & Wu, T. (2022) · Pharmaceuticals · doi:10.3390/ph15101177 · Cited by 82 · see citing works
Xu, L., & Porter, N. A. (2014) · Free Radical Research · doi:10.3109/10715762.2014.985219 · Cited by 84 · see citing works
Self-citationThe onset of lipid peroxidation in rheumatoid arthritis: consequences and monitoring
Łuczaj, W., Gindzienska-Sieskiewicz, E., Jarocka-Karpowicz, I., Andrisic, L., Sierakowski, S., Zarkovic, N., Waeg, G., & Skrzydlewska, E. (2016) · Free Radical Research · doi:10.3109/10715762.2015.1112901 · Cited by 95 · see citing works
Liu, Z., Zhou, D., Li, A., Zhao, M., Hu, Y., Li, D., Xie, H., Zhao, Q., Hu, X., Zhang, J., et al. (2019) · Food Chemistry · doi:10.1016/j.foodchem.2019.125650 · Cited by 83 · see citing works
Winger, A. M., Taylor, N. L., Heazlewood, J. L., Day, D. A., & Millar, A. H. (2007) · Journal of Biological Chemistry · doi:10.1074/jbc.m702385200 · Cited by 83 · see citing works
Promotion of Amyloid β Protein Misfolding and Fibrillogenesis by a Lipid Oxidation Product
Liu, L., Komatsu, H., Murray, I. V. J., & Axelsen, P. H. (2008) · Journal of Molecular Biology · doi:10.1016/j.jmb.2008.01.057 · Cited by 81 · see citing works
Koenitzer, J. R., & Freeman, B. Α. (2010) · Annals of the New York Academy of Sciences · doi:10.1111/j.1749-6632.2010.05559.x · Cited by 80 · see citing works
Stability and analysis of eicosanoids and docosanoids in tissue culture media
Maddipati, K. R., & Zhou, S. (2011) · Prostaglandins & Other Lipid Mediators · doi:10.1016/j.prostaglandins.2011.01.003 · Cited by 78 · see citing works
Youn, B., Kim, S., Moinuddin, S. G. A., Lee, C., Bedgar, D. L., Harper, A. R., Davin, L. B., Lewis, N., & Kang, C. (2006) · Journal of Biological Chemistry · doi:10.1074/jbc.m605900200 · Cited by 78 · see citing works
Mol, M., Regazzoni, L., Altomare, A., Degani, G., Carini, M., Vistoli, G., & Aldini, G. (2017) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2017.01.036 · Cited by 77 · see citing works
Yamamoto, K., Zhang, P., Miake, F., Kashige, N., Aso, Y., Banno, Y., & Fujii, H. (2005) · Comparative Biochemistry and Physiology Part B Biochemistry and Molecular Biology · doi:10.1016/j.cbpc.2005.04.012 · Cited by 75 · see citing works
Zhao, M., Liu, Z., Zhang, W., Xia, G., Li, C., Rakariyatham, K., & Zhou, D. (2025) · Food Research International · doi:10.1016/j.foodres.2025.115811 · Cited by 74 · see citing works
Endogenous Lipid Hydroperoxide-mediated DNA-adduct Formation in Min Mice
Williams, M. V., Lee, S. H., Pollack, M., & Blair, I. A. (2006) · Journal of Biological Chemistry · doi:10.1074/jbc.m600178200 · Cited by 74 · see citing works
Uchida, Y., Ohba, K., Yoshioka, T., Irie, K., Muraki, T., & Maru, Y. (2004) · Journal of Biological Chemistry · doi:10.1074/jbc.m304222200 · Cited by 74 · see citing works
Lee, S. H., Oe, T., & Blair, I. A. (2002) · Chemical Research in Toxicology · doi:10.1021/tx010147j · Cited by 74 · see citing works
Ferroptosis in ulcerative colitis: Potential mechanisms and promising therapeutic targets
Long, D., Mao, C., Huang, Y., Xu, Y., & Zhu, Y. (2024) · Biomedicine & Pharmacotherapy · doi:10.1016/j.biopha.2024.116722 · Cited by 76 · see citing works
Oxidation of 4‐hydroxy‐2‐nonenal by succinic semialdehyde dehydrogenase (ALDH5A)
Murphy, T. C., Amarnath, V., Gibson, K. M., & Picklo, M. J. (2003) · Journal of Neurochemistry · doi:10.1046/j.1471-4159.2003.01839.x · Cited by 72 · see citing works
Carbonylation of proteins—an element of plant ageing
Ciacka, K., Tymiński, M., Gniazdowska, A., & Krasuska, U. (2020) · Planta · doi:10.1007/s00425-020-03414-1 · Cited by 71 · see citing works
A Novel Lipid Hydroperoxide-derived Cyclic Covalent Modification to Histone H4
Oe, T., Arora, J. S., Lee, S. H., & Blair, I. A. (2003) · Journal of Biological Chemistry · doi:10.1074/jbc.m308167200 · Cited by 71 · see citing works
Zhou, X., Zhang, Z., Liu, X., Wu, D., Ding, Y., Li, G., & Wu, Y. (2020) · Comprehensive Reviews in Food Science and Food Safety · doi:10.1111/1541-4337.12535 · Cited by 69 · see citing works
Wang, L., Csallany, A. S., Kerr, B. J., Shurson, G. C., & Chen, C. (2016) · Journal of Agricultural and Food Chemistry · doi:10.1021/acs.jafc.6b01127 · Cited by 69 · see citing works
Porcine oxymyoglobin and lipid oxidation in vitro
Lee, S., Phillips, A. L., Liebler, D. C., & Faustman, C. (2003) · Meat Science · doi:10.1016/s0309-1740(02)00076-1 · Cited by 69 · see citing works
Wang, H., Kozekov, I. D., Harris, T. M., & Rizzo, C. J. (2003) · Journal of the American Chemical Society · doi:10.1021/ja0288800 · Cited by 69 · see citing works
Schneider, C. G., Boeglin, W. E., Yin, H., Porter, N. A., & BRASH, A. R. (2008) · Chemical Research in Toxicology · doi:10.1021/tx700357u · Cited by 67 · see citing works
Self-citation4-Hydroperoxy-2-nonenal-Induced Formation of 1,N2-Etheno-2‘-deoxyguanosine Adducts
Lee, S. H., Arora, J. A., Oe, T., & Blair, I. A. (2005) · Chemical Research in Toxicology · doi:10.1021/tx0497088 · Cited by 66 · see citing works
Separation and identification of phospholipid peroxidation products
Milne, G. L., & Porter, N. A. (2001) · Lipids · doi:10.1007/s11745-001-0841-2 · Cited by 65 · see citing works
Self-citationPreventive effects of Chlorella on cognitive decline in age-dependent dementia model mice
Nakashima, Y., Ohsawa, I., Konishi, F., Hasegawa, T., Kumamoto, S., Suzuki, Y., & Ohta, S. (2009) · Neuroscience Letters · doi:10.1016/j.neulet.2009.08.044 · Cited by 65 · see citing works
Winger, A. M., Millar, A. H., & Day, D. A. (2005) · Biochemical Journal · doi:10.1042/bj20042044 · Cited by 65 · see citing works
Singh, S. P., Janecki, A. J., Srivastava, S., Awasthi, S., Awasthi, S., Xia, S. J., & Zimniak, P. (2002) · Journal of Biological Chemistry · doi:10.1074/jbc.m109678200 · Cited by 64 · see citing works
Hormetic and regulatory effects of lipid peroxidation mediators in pancreatic beta cells
Maulucci, G., Daniel, B., Cohen, O., Avrahami, Y., & Sasson, S. (2016) · Molecular Aspects of Medicine · doi:10.1016/j.mam.2016.03.001 · Cited by 63 · see citing works
Szapacs, M. E., Kim, H., Porter, N. A., & Liebler, D. C. (2008) · Journal of Proteome Research · doi:10.1021/pr8001222 · Cited by 62 · see citing works
Self-citation
- Authors
- Schneider, C., Tallman, K. A., Porter, N. A., & Brash, A. R.
- Affiliations
- Vanderbilt University (US)
- Corresponding author
- Brash, Alan R.
- Venue
- Journal of Biological Chemistry
- Publisher
- Elsevier BV
- Published
- 2001-06
- Volume
- 276
- Issue
- 24
- Pages
- 20831-20838
- ISSN
- 0021-9258 (ISSN-L)
- OpenAlex
- W2050057935
- Cited by
- 313
- References
- 30
- Citations by year
- 2026: 8 · 2025: 8 · 2024: 3 · 2023: 10 · 2022: 10 · 2021: 8 · 2020: 10 · 2019: 9 · 2018: 4 · 2017: 12 · 2016: 16 · 2015: 12 · 2014: 12 · 2013: 13 · 2012: 10
- FWCI
- 10.34
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Licence
- Locations
- Journal of Biological Chemistry (publishedVersion, cc-by)
- PubMed (publishedVersion)
- Funders
- National Institutes of Health (GM 15431)
- National Institute of General Medical Sciences (GM 15431, GM-53638, R01GM053638)
- 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 › Biochemistry › Eicosanoids and Hypertension Pharmacology
- Keywords
- 4-hydroxynonenal, lipid peroxidation, linoleic acid hydroperoxide, allylic hydrogen abstraction, chiral analysis, 4-hydroxyalkenals
- MeSH terms
- Aldehyde-Lyases, Aldehydes, Chromatography, High Pressure Liquid, Cytochrome P-450 Enzyme System, Kinetics, Linoleic Acids, Lipid Peroxides, Lipoxygenase, Recombinant Proteins, Glycine max, Spectrophotometry, Ultraviolet, Stereoisomerism, Vitamin E, Cucurbitaceae
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