4-hhe (BioDeep_00000594526)
代谢物信息卡片
(±)-4-hydroxy-2E-hexenal
化学式: C6H10O2 (114.068076)
中文名称: (E)-4-羟基己烯醛
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CCC(C=CC=O)O
InChI: InChI=1S/C6H10O2/c1-2-6(8)4-3-5-7/h3-6,8H,2H2,1H3/b4-3+
描述信息
同义名列表
数据库引用编号
7 个数据库交叉引用编号
- ChEBI: CHEBI:180385
- PubChem: 5283314
- Metlin: METLIN36538
- LipidMAPS: LMFA06000016
- CAS: 160708-91-8
- CAS: 17427-08-6
- CAS: 17427-21-3
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
0 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Rafael Pineda-Alemán, Camila Cabarcas-Herrera, Antistio Alviz-Amador, Humberto Pérez-Gonzalez, Erika Rodríguez-Cavallo, Darío Méndez-Cuadro. Synthesizing Amino Acids Modified with Reactive Carbonyls in Silico to Assess Structural Effects Using Molecular Dynamics Simulations.
Journal of visualized experiments : JoVE.
2024 Apr; ?(206):. doi:
10.3791/66605. [PMID: 38738901] - Grace Y Sun, Michael K Appenteng, Runting Li, Taeseon Woo, Bo Yang, Chao Qin, Meixia Pan, Magdalena Cieślik, Jiankun Cui, Kevin L Fritsche, Zezong Gu, Matthew Will, David Beversdorf, Agata Adamczyk, Xianlin Han, C Michael Greenlief. Docosahexaenoic Acid (DHA) Supplementation Alters Phospholipid Species and Lipid Peroxidation Products in Adult Mouse Brain, Heart, and Plasma.
Neuromolecular medicine.
2021 03; 23(1):118-129. doi:
10.1007/s12017-020-08616-0. [PMID: 32926329] - Christophe O Soulage, Caroline C Pelletier, Nans Florens, Sandrine Lemoine, Laurence Dubourg, Laurent Juillard, Fitsum Guebre-Egziabher. Two Toxic Lipid Aldehydes, 4-hydroxy-2-hexenal (4-HHE) and 4-hydroxy-2-nonenal (4-HNE), Accumulate in Patients with Chronic Kidney Disease.
Toxins.
2020 09; 12(9):. doi:
10.3390/toxins12090567. [PMID: 32899405] - Lukai Ma, Guoqin Liu, Weiwei Cheng, Xinqi Liu, Charles Brennan, Margaret Anne Brennan, Huifan Liu, Qin Wang. The effect of heating on the formation of 4-hydroxy-2-hexenal and 4-hydroxy-2-nonenal in unsaturated vegetable oils: Evaluation of oxidation indicators.
Food chemistry.
2020 Aug; 321(?):126603. doi:
10.1016/j.foodchem.2020.126603. [PMID: 32244142] - Garrett Ungerer, Jiankun Cui, Tina Ndam, Mikeala Bekemeier, Hailong Song, Runting Li, Heather R Siedhoff, Bo Yang, Michael K Appenteng, C Michael Greenlief, Dennis K Miller, Grace Y Sun, William R Folk, Zezong Gu. Harpagophytum procumbens Extract Ameliorates Allodynia and Modulates Oxidative and Antioxidant Stress Pathways in a Rat Model of Spinal Cord Injury.
Neuromolecular medicine.
2020 06; 22(2):278-292. doi:
10.1007/s12017-019-08585-z. [PMID: 31900786] - Bebiana C Sousa, Tanzim Ahmed, William L Dann, Jed Ashman, Alexandre Guy, Thierry Durand, Andrew R Pitt, Corinne M Spickett. Short-chain lipid peroxidation products form covalent adducts with pyruvate kinase and inhibit its activity in vitro and in breast cancer cells.
Free radical biology & medicine.
2019 11; 144(?):223-233. doi:
10.1016/j.freeradbiomed.2019.05.028. [PMID: 31173844] - Thomas Van Hecke, Sophie Goethals, Els Vossen, Stefaan De Smet. Long-Chain n-3 PUFA Content and n-6/n-3 PUFA Ratio in Mammal, Poultry, and Fish Muscles Largely Explain Differential Protein and Lipid Oxidation Profiles Following In Vitro Gastrointestinal Digestion.
Molecular nutrition & food research.
2019 11; 63(22):e1900404. doi:
10.1002/mnfr.201900404. [PMID: 31483096] - Lukai Ma, Guoqin Liu, Weiwei Cheng, Xinqi Liu, Huifan Liu, Qin Wang. Matrix-mediated distribution of 4-hydroxy-2-hexanal (nonenal) during deep-frying of chicken breast and potato sticks in vegetable oil.
Food & function.
2019 Nov; 10(11):7052-7062. doi:
10.1039/c9fo01878f. [PMID: 31616895] - Francisco J Hidalgo, Rosario Zamora. Characterization of Carbonyl-Phenol Adducts Produced by Food Phenolic Trapping of 4-Hydroxy-2-hexenal and 4-Hydroxy-2-nonenal.
Journal of agricultural and food chemistry.
2019 Feb; 67(7):2043-2051. doi:
10.1021/acs.jafc.8b07091. [PMID: 30702290] - Jiri Hlusicka, Tomas Loster, Lucie Lischkova, Manuela Vaneckova, Zdenek Seidl, Pavel Diblik, Pavel Kuthan, Pavel Urban, Tomas Navratil, Petr Kacer, Sergey Zakharov. Role of activation of lipid peroxidation in the mechanisms of acute methanol poisoning.
Clinical toxicology (Philadelphia, Pa.).
2018 10; 56(10):893-903. doi:
10.1080/15563650.2018.1455980. [PMID: 29607701] - Amy K Hauck, Tong Zhou, Wendy Hahn, Raphael Petegrosso, Rui Kuang, Yue Chen, David A Bernlohr. Obesity-induced protein carbonylation in murine adipose tissue regulates the DNA-binding domain of nuclear zinc finger proteins.
The Journal of biological chemistry.
2018 08; 293(35):13464-13476. doi:
10.1074/jbc.ra118.003469. [PMID: 30012885] - Bo Yang, Runting Li, C Michael Greenlief, Kevin L Fritsche, Zezong Gu, Jiankun Cui, James C Lee, David Q Beversdorf, Grace Y Sun. Unveiling anti-oxidative and anti-inflammatory effects of docosahexaenoic acid and its lipid peroxidation product on lipopolysaccharide-stimulated BV-2 microglial cells.
Journal of neuroinflammation.
2018 Jul; 15(1):202. doi:
10.1186/s12974-018-1232-3. [PMID: 29986724] - S Chevolleau, M-H Noguer-Meireles, I Jouanin, N Naud, F Pierre, F Gueraud, L Debrauwer. Development and validation of an ultra high performance liquid chromatography-electrospray tandem mass spectrometry method using selective derivatisation, for the quantification of two reactive aldehydes produced by lipid peroxidation, HNE (4-hydroxy-2(E)-nonenal) and HHE (4-hydroxy-2(E)-hexenal) in faecal water.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2018 Apr; 1083(?):171-179. doi:
10.1016/j.jchromb.2018.03.002. [PMID: 29549740] - Christophe O Soulage, Laura Sardón Puig, Laurent Soulère, Bader Zarrouki, Michel Guichardant, Michel Lagarde, Nicolas J Pillon. Skeletal muscle insulin resistance is induced by 4-hydroxy-2-hexenal, a by-product of n-3 fatty acid peroxidation.
Diabetologia.
2018 03; 61(3):688-699. doi:
10.1007/s00125-017-4528-4. [PMID: 29299636] - Lukai Ma, Guoqin Liu. Simultaneous Analysis of Malondialdehyde, 4-Hydroxy-2-hexenal, and 4-Hydroxy-2-nonenal in Vegetable Oil by Reversed-Phase High-Performance Liquid Chromatography.
Journal of agricultural and food chemistry.
2017 Dec; 65(51):11320-11328. doi:
10.1021/acs.jafc.7b04566. [PMID: 29179555] - Bebiana C Sousa, Andrew R Pitt, Corinne M Spickett. Chemistry and analysis of HNE and other prominent carbonyl-containing lipid oxidation compounds.
Free radical biology & medicine.
2017 10; 111(?):294-308. doi:
10.1016/j.freeradbiomed.2017.02.003. [PMID: 28192230] - Lara Rodríguez-Ribera, Craig Slattery, Tara Mc Morrow, Ricard Marcos, Susana Pastor. Reactive carbonyl compounds impair wound healing by vimentin collapse and loss of the primary cilium.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2017 Oct; 108(Pt A):128-138. doi:
10.1016/j.fct.2017.07.055. [PMID: 28760545] - Petr Grúz, Masatomi Shimizu, Kei-Ichi Sugiyama, Masamitsu Honma. Mutagenicity of ω-3 fatty acid peroxidation products in the Ames test.
Mutation research. Genetic toxicology and environmental mutagenesis.
2017 Jul; 819(?):14-19. doi:
10.1016/j.mrgentox.2017.05.004. [PMID: 28622825] - Joon Hyuk Suh, Yue S Niu, Wei-Lun Hung, Chi-Tang Ho, Yu Wang. Lipidomic analysis for carbonyl species derived from fish oil using liquid chromatography-tandem mass spectrometry.
Talanta.
2017 Jun; 168(?):31-42. doi:
10.1016/j.talanta.2017.03.023. [PMID: 28391860] - Ryusuke Tanaka, Mami Ishimaru, Hideo Hatate, Yoshimasa Sugiura, Teruo Matsushita. Relationship between 4-hydroxy-2-hexenal contents and commercial grade by organoleptic judgement in Japanese dried laver Porphyra spp.
Food chemistry.
2016 Dec; 212(?):104-9. doi:
10.1016/j.foodchem.2016.05.166. [PMID: 27374512] - G Muzio, M Ricci, N Traverso, F Monacelli, M Oraldi, M Maggiora, R A Canuto. 4-Hydroxyhexenal and 4-hydroxynonenal are mediators of the anti-cachectic effect of n-3 and n-6 polyunsaturated fatty acids on human lung cancer cells.
Free radical biology & medicine.
2016 10; 99(?):63-70. doi:
10.1016/j.freeradbiomed.2016.07.031. [PMID: 27480845] - Karin Larsson, Cecilia Tullberg, Marie Alminger, Robert Havenaar, Ingrid Undeland. Malondialdehyde and 4-hydroxy-2-hexenal are formed during dynamic gastrointestinal in vitro digestion of cod liver oils.
Food & function.
2016 Aug; 7(8):3458-67. doi:
10.1039/c6fo00635c. [PMID: 27396605] - Anna Moniuszko-Malinowska, Wojciech Łuczaj, Iwona Jarocka-Karpowicz, Sławomir Pancewicz, Joanna Zajkowska, Luka Andrisic, Neven Zarkovic, Elżbieta Skrzydlewska. Lipid peroxidation in the pathogenesis of neuroborreliosis.
Free radical biology & medicine.
2016 07; 96(?):255-63. doi:
10.1016/j.freeradbiomed.2016.04.032. [PMID: 27140232] - Cecilia Tullberg, Karin Larsson, Nils-Gunnar Carlsson, Irene Comi, Nathalie Scheers, Gerd Vegarud, Ingrid Undeland. Formation of reactive aldehydes (MDA, HHE, HNE) during the digestion of cod liver oil: comparison of human and porcine in vitro digestion models.
Food & function.
2016 03; 7(3):1401-12. doi:
10.1039/c5fo01332a. [PMID: 26838473] - Karin Larsson, Hanna Harrysson, Robert Havenaar, Marie Alminger, Ingrid Undeland. 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.
Food & function.
2016 Feb; 7(2):1176-87. doi:
10.1039/c5fo01401h. [PMID: 26824872] - Christina Steppeler, John-Erik Haugen, Rune Rødbotten, Bente Kirkhus. Formation of Malondialdehyde, 4-Hydroxynonenal, and 4-Hydroxyhexenal during in Vitro Digestion of Cooked Beef, Pork, Chicken, and Salmon.
Journal of agricultural and food chemistry.
2016 Jan; 64(2):487-96. doi:
10.1021/acs.jafc.5b04201. [PMID: 26654171] - Wojciech Łuczaj, Anna Moniuszko, Iwona Jarocka-Karpowicz, Sławomir Pancewicz, Luka Andrisic, Neven Zarkovic, Elżbieta Skrzydlewska. Tick-borne encephalitis--lipid peroxidation and its consequences.
Scandinavian journal of clinical and laboratory investigation.
2016; 76(1):1-9. doi:
10.3109/00365513.2015.1084040. [PMID: 26414861] - Karin Larsson, Katja Istenič, Tune Wulff, Rósa Jónsdóttir, Hordur Kristinsson, Jona Freysdottir, Ingrid Undeland, Polona Jamnik. Effect of in vitro digested cod liver oil of different quality on oxidative, proteomic and inflammatory responses in the yeast Saccharomyces cerevisiae and human monocyte-derived dendritic cells.
Journal of the science of food and agriculture.
2015 Dec; 95(15):3096-106. doi:
10.1002/jsfa.7046. [PMID: 25504560] - Olga Jovanovic, Alina A Pashkovskaya, Andrea Annibal, Mario Vazdar, Nadine Burchardt, Anna Sansone, Lars Gille, Maria Fedorova, Carla Ferreri, Elena E Pohl. The molecular mechanism behind reactive aldehyde action on transmembrane translocations of proton and potassium ions.
Free radical biology & medicine.
2015 Dec; 89(?):1067-76. doi:
10.1016/j.freeradbiomed.2015.10.422. [PMID: 26520807] - Ryusuke Tanaka, Kazuhiro Shigeta, Yoshimasa Sugiura, Hideo Hatate, Teruo Matsushita. Accumulation of hydroxyl lipids and 4-hydroxy-2-hexenal in live fish infected with fish diseases.
Lipids.
2014 Apr; 49(4):385-96. doi:
10.1007/s11745-013-3875-2. [PMID: 24390795] - Fumiyuki Nakagawa, Katsutaro Morino, Satoshi Ugi, Atsushi Ishikado, Keiko Kondo, Daisuke Sato, Shiho Konno, Ken-ichi Nemoto, Chisato Kusunoki, Osamu Sekine, Akihiro Sunagawa, Masanori Kawamura, Noriko Inoue, Yoshihiko Nishio, Hiroshi Maegawa. 4-Hydroxy hexenal derived from dietary n-3 polyunsaturated fatty acids induces anti-oxidative enzyme heme oxygenase-1 in multiple organs.
Biochemical and biophysical research communications.
2014 Jan; 443(3):991-6. doi:
10.1016/j.bbrc.2013.12.085. [PMID: 24361890] - Eşref Demir, Fatma Turna, Bülent Kaya, Amadeu Creus, Ricard Marcos. Mutagenic/recombinogenic effects of four lipid peroxidation products in Drosophila.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2013 Mar; 53(?):221-7. doi:
10.1016/j.fct.2012.11.053. [PMID: 23238235] - Chang Seong Kim, Soo Yeon Joo, Ko Eun Lee, Joon Seok Choi, Eun Hui Bae, Seong Kwon Ma, Suhn Hee Kim, Jongun Lee, Soo Wan Kim. Paricalcitol attenuates 4-hydroxy-2-hexenal-induced inflammation and epithelial-mesenchymal transition in human renal proximal tubular epithelial cells.
PloS one.
2013; 8(5):e63186. doi:
10.1371/journal.pone.0063186. [PMID: 23690997] - Atsushi Ishikado, Katsutaro Morino, Yoshihiko Nishio, Fumiyuki Nakagawa, Atsushi Mukose, Yoko Sono, Nagisa Yoshioka, Keiko Kondo, Osamu Sekine, Takeshi Yoshizaki, Satoshi Ugi, Takashi Uzu, Hiromichi Kawai, Taketoshi Makino, Tomio Okamura, Masayuki Yamamoto, Atsunori Kashiwagi, Hiroshi Maegawa. 4-Hydroxy hexenal derived from docosahexaenoic acid protects endothelial cells via Nrf2 activation.
PloS one.
2013; 8(7):e69415. doi:
10.1371/journal.pone.0069415. [PMID: 23936010] - Bingnan Han, Michael Hare, Samanthi Wickramasekara, Yi Fang, Claudia S Maier. A comparative 'bottom up' proteomics strategy for the site-specific identification and quantification of protein modifications by electrophilic lipids.
Journal of proteomics.
2012 Oct; 75(18):5724-33. doi:
10.1016/j.jprot.2012.07.029. [PMID: 22842153] - Manar Awada, Christophe O Soulage, Anne Meynier, Cyrille Debard, Pascale Plaisancié, Bérengère Benoit, Grégory Picard, Emmanuelle Loizon, Marie-Agnès Chauvin, Monique Estienne, Noël Peretti, Michel Guichardant, Michel Lagarde, Claude Genot, Marie-Caroline Michalski. Dietary oxidized n-3 PUFA induce oxidative stress and inflammation: role of intestinal absorption of 4-HHE and reactivity in intestinal cells.
Journal of lipid research.
2012 Oct; 53(10):2069-2080. doi:
10.1194/jlr.m026179. [PMID: 22865918] - Inger Ottestad, Gjermund Vogt, Kjetil Retterstøl, Mari C Myhrstad, John-Erik Haugen, Astrid Nilsson, Gitte Ravn-Haren, Berit Nordvi, Kirsti W Brønner, Lene F Andersen, Kirsten B Holven, Stine M Ulven. Oxidised fish oil does not influence established markers of oxidative stress in healthy human subjects: a randomised controlled trial.
The British journal of nutrition.
2012 Jul; 108(2):315-26. doi:
10.1017/s0007114511005484. [PMID: 22136711] - Melissa A Bradley, Shuling Xiong-Fister, William R Markesbery, Mark A Lovell. Elevated 4-hydroxyhexenal in Alzheimer's disease (AD) progression.
Neurobiology of aging.
2012 Jun; 33(6):1034-44. doi:
10.1016/j.neurobiolaging.2010.08.016. [PMID: 20965613] - Cécile Gladine, Nicole C Roy, Jean-Paul Rigaudière, Brigitte Laillet, Georges Da Silva, Charlotte Joly, Estelle Pujos-Guillot, Béatrice Morio, Christine Feillet-Coudray, Warren C McNabb, Jean-Michel Chardigny, Blandine Comte. Increasing intake of long-chain n-3 PUFA enhances lipoperoxidation and modulates hepatic gene expression in a dose-dependent manner.
The British journal of nutrition.
2012 May; 107(9):1254-73. doi:
10.1017/s0007114511004259. [PMID: 21914239] - Mark A Lovell, Melissa A Bradley, Shuling X Fister. 4-Hydroxyhexenal (HHE) impairs glutamate transport in astrocyte cultures.
Journal of Alzheimer's disease : JAD.
2012; 32(1):139-46. doi:
10.3233/jad-2012-120409. [PMID: 22766736] - Eşref Demir, Bülent Kaya, Carolina Soriano, Amadeu Creus, Ricard Marcos. Genotoxic analysis of four lipid-peroxidation products in the mouse lymphoma assay.
Mutation research.
2011 Dec; 726(2):98-103. doi:
10.1016/j.mrgentox.2011.07.001. [PMID: 21763450] - Eun Hui Bae, Sunghee Cho, Soo Yeon Joo, Seong Kwon Ma, Suhn Hee Kim, Jongun Lee, Soo Wan Kim. 4-Hydroxy-2-hexenal-induced apoptosis in human renal proximal tubular epithelial cells.
Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association.
2011 Dec; 26(12):3866-73. doi:
10.1093/ndt/gfr386. [PMID: 21771752] - Nicolas J Pillon, Roxane E Vella, Laurent Souleere, Michel Becchi, Michel Lagarde, Christophe O Soulage. Structural and functional changes in human insulin induced by the lipid peroxidation byproducts 4-hydroxy-2-nonenal and 4-hydroxy-2-hexenal.
Chemical research in toxicology.
2011 May; 24(5):752-62. doi:
10.1021/tx200084d. [PMID: 21462967] - Jean-François Lesgards, Cyrielle Gauthier, Juan Iovanna, Nicolas Vidal, Alain Dolla, Pierre Stocker. Effect of reactive oxygen and carbonyl species on crucial cellular antioxidant enzymes.
Chemico-biological interactions.
2011 Mar; 190(1):28-34. doi:
10.1016/j.cbi.2010.12.028. [PMID: 21216240] - Sergio Porté, Agrin Moeini, Irene Reche, Naeem Shafqat, Udo Oppermann, Jaume Farrés, Xavier Parés. Kinetic and structural evidence of the alkenal/one reductase specificity of human ζ-crystallin.
Cellular and molecular life sciences : CMLS.
2011 Mar; 68(6):1065-77. doi:
10.1007/s00018-010-0508-2. [PMID: 20835842] - Atsushi Ishikado, Yoshihiko Nishio, Katsutaro Morino, Satoshi Ugi, Hajime Kondo, Taketoshi Makino, Atsunori Kashiwagi, Hiroshi Maegawa. Low concentration of 4-hydroxy hexenal increases heme oxygenase-1 expression through activation of Nrf2 and antioxidative activity in vascular endothelial cells.
Biochemical and biophysical research communications.
2010 Nov; 402(1):99-104. doi:
10.1016/j.bbrc.2010.09.124. [PMID: 20920477] - Nicolas J Pillon, Laurent Soulère, Roxane E Vella, Marine Croze, Bertrand R Caré, Hedi A Soula, Alain Doutheau, Michel Lagarde, Christophe O Soulage. Quantitative structure-activity relationship for 4-hydroxy-2-alkenal induced cytotoxicity in L6 muscle cells.
Chemico-biological interactions.
2010 Oct; 188(1):171-80. doi:
10.1016/j.cbi.2010.06.015. [PMID: 20619253] - Eric K Long, Matthew J Picklo. Trans-4-hydroxy-2-hexenal, a product of n-3 fatty acid peroxidation: make some room HNE...
Free radical biology & medicine.
2010 Jul; 49(1):1-8. doi:
10.1016/j.freeradbiomed.2010.03.015. [PMID: 20353821] - Eric K Long, Thad A Rosenberger, Matthew J Picklo. Ethanol withdrawal increases glutathione adducts of 4-hydroxy-2-hexenal but not 4-hydroxyl-2-nonenal in the rat cerebral cortex.
Free radical biology & medicine.
2010 Feb; 48(3):384-90. doi:
10.1016/j.freeradbiomed.2009.10.048. [PMID: 19878718] - Marie-Caroline Michalski, Catherine Calzada, Asami Makino, Sabine Michaud, Michel Guichardant. Oxidation products of polyunsaturated fatty acids in infant formulas compared to human milk--a preliminary study.
Molecular nutrition & food research.
2008 Dec; 52(12):1478-85. doi:
10.1002/mnfr.200700451. [PMID: 18792926] - Eric K Long, Tonya C Murphy, Laura J Leiphon, John Watt, Jason D Morrow, Ginger L Milne, Jocelyn R H Howard, Matthew J Picklo. Trans-4-hydroxy-2-hexenal is a neurotoxic product of docosahexaenoic (22:6; n-3) acid oxidation.
Journal of neurochemistry.
2008 May; 105(3):714-24. doi:
10.1111/j.1471-4159.2007.05175.x. [PMID: 18194211] - David A Andersson, Clive Gentry, Sian Moss, Stuart Bevan. Transient receptor potential A1 is a sensory receptor for multiple products of oxidative stress.
The Journal of neuroscience : the official journal of the Society for Neuroscience.
2008 Mar; 28(10):2485-94. doi:
10.1523/jneurosci.5369-07.2008. [PMID: 18322093] - J Surh, S Lee, H Kwon. 4-hydroxy-2-alkenals in polyunsaturated fatty acids-fortified infant formulas and other commercial food products.
Food additives and contaminants.
2007 Nov; 24(11):1209-18. doi:
10.1080/02652030701422465. [PMID: 17852396] - Bingnan Han, Jan F Stevens, Claudia S Maier. Design, synthesis, and application of a hydrazide-functionalized isotope-coded affinity tag for the quantification of oxylipid-protein conjugates.
Analytical chemistry.
2007 May; 79(9):3342-54. doi:
10.1021/ac062262a. [PMID: 17385840] - M Guichardant, S Bacot, P Molière, M Lagarde. Hydroxy-alkenals from the peroxidation of n-3 and n-6 fatty acids and urinary metabolites.
Prostaglandins, leukotrienes, and essential fatty acids.
2006 Sep; 75(3):179-82. doi:
10.1016/j.plefa.2006.05.006. [PMID: 16828271] - Toshiya Saeki, Miho Ichiba, Naotada Tanabe, Masaru Ueki, Kinya Okamoto, Yoshiko Matsunaga, Keiko Hosho, Takamasa Kanbe, Hiroyuki Tsuchiya, Akihiro Kurimasa, Sadako Yamada, Yasuaki Hirooka, Ichiro Hisatome, Yukihiro Kishimoto, Takeaki Suou, Yoshikazu Murawaki, Hironaka Kawasaki, Junji Yodoi, Goshi Shiota. Expression of oxidative stress-related molecules in circulating leukocytes and urine in patients with chronic viral hepatitis.
Liver international : official journal of the International Association for the Study of the Liver.
2006 Mar; 26(2):157-65. doi:
10.1111/j.1478-3231.2005.01213.x. [PMID: 16448453] - J Surh, H Kwon. Estimation of daily exposure to 4-hydroxy-2-alkenals in Korean foods containing n-3 and n-6 polyunsaturated fatty acids.
Food additives and contaminants.
2005 Aug; 22(8):701-8. doi:
10.1080/02652030500164359. [PMID: 16147425] - Yukihiro Tsuchiya, Mitsune Yamaguchi, Toshiyuki Chikuma, Hiroshi Hojo. Degradation of glyceraldehyde-3-phosphate dehydrogenase triggered by 4-hydroxy-2-nonenal and 4-hydroxy-2-hexenal.
Archives of biochemistry and biophysics.
2005 Jun; 438(2):217-22. doi:
10.1016/j.abb.2005.04.015. [PMID: 15907785] - Akira Kitase, Keisuke Hino, Takakazu Furutani, Michiari Okuda, Toshikazu Gondo, Isao Hidaka, Yuichi Hara, Yuhki Yamaguchi, Kiwamu Okita. In situ detection of oxidized n-3 polyunsaturated fatty acids in chronic hepatitis C: correlation with hepatic steatosis.
Journal of gastroenterology.
2005 Jun; 40(6):617-24. doi:
10.1007/s00535-005-1596-x. [PMID: 16007396] - S Choudhary, T Xiao, S Srivastava, W Zhang, L L Chan, L A Vergara, F J G M Van Kuijk, N H Ansari. Toxicity and detoxification of lipid-derived aldehydes in cultured retinal pigmented epithelial cells.
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