5-HETE (BioDeep_00000003305)

Main id: BioDeep_00000594376

 

human metabolite Endogenous blood metabolite


代谢物信息卡片


(5S,6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoic acid

化学式: C20H32O3 (320.2351322)
中文名称: 5(S)-羟化二十烷四烯酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.2%

Reviewed

Last reviewed on 2024-10-28.

Cite this Page

5-HETE. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/5-hete (retrieved 2024-11-03) (BioDeep RN: BioDeep_00000003305). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C(=C\[C@@H](CCCC(=O)O)O)/C=C\C/C=C\C/C=C\CCCCC
InChI: InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16,19,21H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+/t19-/m0/s1

描述信息

5-Hydroxyeicosatetraenoic acid (5-HETE) is an endogenous eicosanoid. 5-HETE is an intermediate in the pathway of leukotriene synthesis. In addition, it is a modulator of tubuloglomerular feedback.; 5-hydroxyeicosatetraenoic acid (5-HETE) is an endogenous eicosanoid. 5-HETE is an intermediate in Arachidonic acid metabolism. It is converted from 5(S)-HPETE via the enzyme glutathione peroxidase (EC 1.11.1.9)and then it is converted to 5-OxoETE. It is also involved in the pathway of leukotriene synthesis. In addition, it is a modulator of tubuloglomerular feedback. 5-HETE is found in corn.
5-hydroxyeicosatetraenoic acid (5-HETE) is an endogenous eicosanoid. 5-HETE is an intermediate in arachidonic acid metabolism. It is converted from 5(S)-HPETE via the enzyme glutathione peroxidase (EC 1.11.1.9)and then converted to 5-OxoETE. It is also involved in the pathway of leukotriene synthesis. In addition, it is a modulator of tubuloglomerular feedback.

同义名列表

34 个代谢物同义名

5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,Z,Z,Z)-(+-)-isomer; 5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (S)-(e,Z,Z,Z)-isomer; (6E,8Z,11Z,14Z)-(5S)-5-Hydroxyicosa-6,8,11,14-tetraenoic acid; 5-Hydroxy-6,8,11,14-eicosatetraenoic acid, R-(e,Z,Z,Z)-isomer; (5S,6E,8Z,11Z,14Z)-5-Hydroxy-6,8,11,14-eicosatetraenoic acid; (5S,6E,8Z,11Z,14Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoic acid; 5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,Z,Z,Z)-isomer; 5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,e,Z,Z)-isomer; (5S,6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoic acid; (6E,8Z,11Z,14Z)-(5S)-5-Hydroxyicosa-6,8,11,14-tetraenoate; (5S,6E,8Z,11Z,14Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoate; 5(S)-Hydroxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoic acid; (S)-(e,Z,Z,Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoic acid; 5(S)-Hydroxy-6-trans-8,11,14-cis-eicosatetraenoic acid; 5(S)-Hydroxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoate; 5S-Hydroxy-6,8,11,14-(e,Z,Z,Z)-eicosatetraenoic acid; (S)-(e,Z,Z,Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoate; 5(S)-Hydroxy-6-trans-8,11,14-cis-eicosatetraenoate; 5-L-Hydroxy-6,8,11,14-eicosatetraenoic acid; 5S-Hydroxy-6,8,11,14-eicosatetraenoic acid; 5-Hydroxy-6,8,11,14-eicosatetraenoic acid; 5-L-Hydroxy-6,8,11,14-eicosatetraenoate; 5S-Hydroxy-6,8,11,14-eicosatetraenoate; 5-Hydroxy-6,8,11,14-eicosatetraenoate; 5(S)-Hydroxyeicosatetraenoic acid; 5-Hydroxyeicosatetraenoic acid; FA(20:4(5S-OH,6E,8Z,11Z,14Z)); 5(S)-Hydroxyeicosatetraenoate; FA(20:4(5-OH,6E,8Z,11Z,14Z)); 5-Hydroxyeicosatetraenoate; 5-Hydroxyarachidonic acid; 5(S)-HETE; 5S-HETE; 5-Hete



数据库引用编号

28 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(4)

BioCyc(0)

PlantCyc(0)

代谢反应

53 个相关的代谢反应过程信息。

Reactome(5)

BioCyc(0)

WikiPathways(2)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(46)

PharmGKB(0)

2 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

  • Ai Lin Daphne Teh, Jaime Jacqueline Jayapalan, Mun Fai Loke, Azida Juana Wan Abdul Kadir, Visvaraja Subrayan. Identification of potential serum metabolic biomarkers for patient with keratoconus using untargeted metabolomics approach. Experimental eye research. 2021 10; 211(?):108734. doi: 10.1016/j.exer.2021.108734. [PMID: 34428458]
  • Tatsuro Nakamura. The roles of lipid mediators in type I hypersensitivity. Journal of pharmacological sciences. 2021 Sep; 147(1):126-131. doi: 10.1016/j.jphs.2021.06.001. [PMID: 34294363]
  • Jianjun Tang, Chuang Zhang, Jingjing Lin, Peng Duan, Jian Long, Hongyan Zhu. ALOX5-5-HETE promotes gastric cancer growth and alleviates chemotherapy toxicity via MEK/ERK activation. Cancer medicine. 2021 08; 10(15):5246-5255. doi: 10.1002/cam4.4066. [PMID: 34121352]
  • Kristen J Polinski, Elizabeth A Bemis, Fan Yang, Tessa Crume, M Kristen Demoruelle, Marie Feser, Jennifer Seifert, James R O'Dell, Ted R Mikuls, Michael H Weisman, Peter K Gregersen, Richard M Keating, Jane Buckner, Nichole Reisdorph, Kevin D Deane, Michael Clare-Salzler, V Michael Holers, Jill M Norris. Association of Lipid Mediators With Development of Future Incident Inflammatory Arthritis in an Anti-Citrullinated Protein Antibody-Positive Population. Arthritis & rheumatology (Hoboken, N.J.). 2021 06; 73(6):955-962. doi: 10.1002/art.41631. [PMID: 33381911]
  • Laura Niederstaetter, Benjamin Neuditschko, Julia Brunmair, Lukas Janker, Andrea Bileck, Giorgia Del Favero, Christopher Gerner. Eicosanoid Content in Fetal Calf Serum Accounts for Reproducibility Challenges in Cell Culture. Biomolecules. 2021 01; 11(1):. doi: 10.3390/biom11010113. [PMID: 33467719]
  • Sangmae Sharon Bae, Yuen Yin Lee, Ani Shahbazian, Jennifer Wang, David Meriwether, Ilana Golub, Buzand Oganesian, Tyler Dowd, Srinivasa T Reddy, Christina Charles-Schoeman. High- density lipoprotein function is abnormal in idiopathic inflammatory myopathies. Rheumatology (Oxford, England). 2020 11; 59(11):3515-3525. doi: 10.1093/rheumatology/keaa273. [PMID: 32830270]
  • Miriam C Wolters, Julia Schmetzer, Christine V Möser, Lisa Hahnefeld, Carlo Angioni, Dominique Thomas, Nerea Ferreirós, Gerd Geisslinger, Ellen Niederberger. Exercise-Induced Changes in Bioactive Lipids Might Serve as Potential Predictors of Post-Exercise Hypotension. A Pilot Study in Healthy Volunteers. Cells. 2020 09; 9(9):. doi: 10.3390/cells9092111. [PMID: 32948055]
  • Elżbieta Cecerska-Heryć, Rafał Heryć, Magda Wiśniewska, Natalia Serwin, Bartłomiej Grygorcewicz, Barbara Dołęgowska. Effect of renal replacement therapy on selected arachidonic acid derivatives concentration. BMC nephrology. 2020 09; 21(1):394. doi: 10.1186/s12882-020-02053-8. [PMID: 32917166]
  • Nathaniel C Gilbert, Jana Gerstmeier, Erin E Schexnaydre, Friedemann Börner, Ulrike Garscha, David B Neau, Oliver Werz, Marcia E Newcomer. Structural and mechanistic insights into 5-lipoxygenase inhibition by natural products. Nature chemical biology. 2020 07; 16(7):783-790. doi: 10.1038/s41589-020-0544-7. [PMID: 32393899]
  • Juan Antonio Giménez-Bastida, Antonio González-Sarrías, Juan Carlos Espín, Claus Schneider. Inhibition of 5-Lipoxygenase-Derived Leukotrienes and Hemiketals as a Novel Anti-Inflammatory Mechanism of Urolithins. Molecular nutrition & food research. 2020 06; 64(11):e2000129. doi: 10.1002/mnfr.202000129. [PMID: 32306507]
  • H Patrick MacKnight, Daniel J Stephenson, L Alexis Hoeferlin, Savannah D Benusa, James T DeLigio, Kenneth D Maus, Anika N Ali, Jennifer S Wayne, Margaret A Park, Edward H Hinchcliffe, Rhoderick E Brown, John J Ryan, Robert F Diegelmann, Charles E Chalfant. The interaction of ceramide 1-phosphate with group IVA cytosolic phospholipase A2 coordinates acute wound healing and repair. Science signaling. 2019 12; 12(610):. doi: 10.1126/scisignal.aav5918. [PMID: 31796632]
  • Dmitry V Chistyakov, Ivan S Filimonov, Nadezhda V Azbukina, Sergei V Goriainov, Viktor V Chistyakov, Maksim A Fomich, Andrei V Bekish, Vadim V Shmanai, Marina G Sergeeva, Mikhail S Shchepinov. Deuterated Arachidonic Acids Library for Regulation of Inflammation and Controlled Synthesis of Eicosanoids: An In Vitro Study. Molecules (Basel, Switzerland). 2018 Dec; 23(12):. doi: 10.3390/molecules23123331. [PMID: 30558277]
  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
  • C Morgantini, S Trifirò, D Tricò, D Meriwether, S Baldi, A Mengozzi, S T Reddy, A Natali. A short-term increase in dietary cholesterol and fat intake affects high-density lipoprotein composition in healthy subjects. Nutrition, metabolism, and cardiovascular diseases : NMCD. 2018 06; 28(6):575-581. doi: 10.1016/j.numecd.2018.03.005. [PMID: 29699812]
  • Anne E Barden, Sujata Shinde, Valerie Burke, Ian B Puddey, Lawrence J Beilin, Ashley B Irish, Gerald F Watts, Trevor A Mori. The effect of n-3 fatty acids and coenzyme Q10 supplementation on neutrophil leukotrienes, mediators of inflammation resolution and myeloperoxidase in chronic kidney disease. Prostaglandins & other lipid mediators. 2018 05; 136(?):1-8. doi: 10.1016/j.prostaglandins.2018.03.002. [PMID: 29577973]
  • Charles Austin Pickens, Lorraine M Sordillo, Chen Zhang, Jenifer I Fenton. Obesity is positively associated with arachidonic acid-derived 5- and 11-hydroxyeicosatetraenoic acid (HETE). Metabolism: clinical and experimental. 2017 05; 70(?):177-191. doi: 10.1016/j.metabol.2017.01.034. [PMID: 28403941]
  • Oscar D Rangel-Huerta, Concepcion M Aguilera, Antonio Perez-de-la-Cruz, Fernando Vallejo, Francisco Tomas-Barberan, Angel Gil, Maria D Mesa. A serum metabolomics-driven approach predicts orange juice consumption and its impact on oxidative stress and inflammation in subjects from the BIONAOS study. Molecular nutrition & food research. 2017 02; 61(2):. doi: 10.1002/mnfr.201600120. [PMID: 27689343]
  • A L Peters, M A T Vervaart, R van Bruggen, D de Korte, R Nieuwland, W Kulik, A P J Vlaar. Non-polar lipids accumulate during storage of transfusion products and do not contribute to the onset of transfusion-related acute lung injury. Vox sanguinis. 2017 Jan; 112(1):25-32. doi: 10.1111/vox.12453. [PMID: 28097705]
  • G Andres Contreras, Clarissa Strieder-Barboza, Jonas de Souza, Jeff Gandy, Vengai Mavangira, Adam L Lock, Lorraine M Sordillo. Periparturient lipolysis and oxylipid biosynthesis in bovine adipose tissues. PloS one. 2017; 12(12):e0188621. doi: 10.1371/journal.pone.0188621. [PMID: 29206843]
  • Hua Yuan, Xuemei Li, Xiuying Zhang, Rui Kang, Daolin Tang. Identification of ACSL4 as a biomarker and contributor of ferroptosis. Biochemical and biophysical research communications. 2016 09; 478(3):1338-43. doi: 10.1016/j.bbrc.2016.08.124. [PMID: 27565726]
  • Qiaoxia Bian, Weihui Wang, Nannan Wang, Yan Peng, Wen Ma, Ronghua Dai. Arachidonic acid metabolomic study of BPH in rats and the interventional effects of Zishen pill, a traditional Chinese medicine. Journal of pharmaceutical and biomedical analysis. 2016 Sep; 128(?):149-157. doi: 10.1016/j.jpba.2016.05.027. [PMID: 27262108]
  • William S Powell, Joshua Rokach. Biosynthesis, biological effects, and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid. Biochimica et biophysica acta. 2015 Apr; 1851(4):340-55. doi: 10.1016/j.bbalip.2014.10.008. [PMID: 25449650]
  • Marco Sisignano, Carlo Angioni, Nerea Ferreiros, Claus-Dieter Schuh, Jing Suo, Yannick Schreiber, John M Dawes, Ana Antunes-Martins, David L H Bennett, Stephen B McMahon, Gerd Geisslinger, Klaus Scholich. Synthesis of lipid mediators during UVB-induced inflammatory hyperalgesia in rats and mice. PloS one. 2013; 8(12):e81228. doi: 10.1371/journal.pone.0081228. [PMID: 24349046]
  • Joanna Raszeja-Wyszomirska, Krzysztof Safranow, Małgorzata Milkiewicz, Piotr Milkiewicz, Agnieszka Szynkowska, Ewa Stachowska. Lipidic last breath of life in patients with alcoholic liver disease. Prostaglandins & other lipid mediators. 2012 Oct; 99(1-2):51-6. doi: 10.1016/j.prostaglandins.2012.06.001. [PMID: 22706383]
  • Jun Yang, Jason P Eiserich, Carroll E Cross, Brian M Morrissey, Bruce D Hammock. Metabolomic profiling of regulatory lipid mediators in sputum from adult cystic fibrosis patients. Free radical biology & medicine. 2012 Jul; 53(1):160-71. doi: 10.1016/j.freeradbiomed.2012.05.001. [PMID: 22580336]
  • Si-Yang Fan, Hua-Wu Zeng, Yue-Hu Pei, Li Li, Ji Ye, Yue-Xin Pan, Ji-Gang Zhang, Xing Yuan, Wei-Dong Zhang. The anti-inflammatory activities of an extract and compounds isolated from Platycladus orientalis (Linnaeus) Franco in vitro and ex vivo. Journal of ethnopharmacology. 2012 Jun; 141(2):647-52. doi: 10.1016/j.jep.2011.05.019. [PMID: 21619922]
  • E Patterson, R Wall, G F Fitzgerald, R P Ross, C Stanton. Health implications of high dietary omega-6 polyunsaturated Fatty acids. Journal of nutrition and metabolism. 2012; 2012(?):539426. doi: 10.1155/2012/539426. [PMID: 22570770]
  • Tianfu Wu, Chun Xie, Jie Han, Yujin Ye, Jim Weiel, Quan Li, Irene Blanco, Chul Ahn, Nancy Olsen, Chaim Putterman, Ramesh Saxena, Chandra Mohan. Metabolic disturbances associated with systemic lupus erythematosus. PloS one. 2012; 7(6):e37210. doi: 10.1371/journal.pone.0037210. [PMID: 22723834]
  • Raquel Martín-Venegas, Rosario Casillas, Olga Jáuregui, Juan José Moreno. Rapid simultaneous analysis of cyclooxygenase, lipoxygenase and cytochrome P-450 metabolites of arachidonic and linoleic acids using high performance liquid chromatography/mass spectrometry in tandem mode. Journal of pharmaceutical and biomedical analysis. 2011 Dec; 56(5):976-82. doi: 10.1016/j.jpba.2011.06.018. [PMID: 21880455]
  • Martin J Edelman, Lydia Hodgson, Xiaofei Wang, Robert Christenson, Scott Jewell, Everett Vokes, Robert Kratzke. Serum vascular endothelial growth factor and COX-2/5-LOX inhibition in advanced non-small cell lung cancer: Cancer and Leukemia Group B 150304. Journal of thoracic oncology : official publication of the International Association for the Study of Lung Cancer. 2011 Nov; 6(11):1902-6. doi: 10.1097/jto.0b013e31822a7383. [PMID: 21964530]
  • Suzanna M Zick, D Kim Turgeon, Shaiju K Vareed, Mack T Ruffin, Amie J Litzinger, Benjamin D Wright, Sara Alrawi, Daniel P Normolle, Zora Djuric, Dean E Brenner. Phase II study of the effects of ginger root extract on eicosanoids in colon mucosa in people at normal risk for colorectal cancer. Cancer prevention research (Philadelphia, Pa.). 2011 Nov; 4(11):1929-37. doi: 10.1158/1940-6207.capr-11-0224. [PMID: 21990307]
  • Santiago E Farias, Kim A Heidenreich, Max V Wohlauer, Robert C Murphy, Ernest E Moore. Lipid mediators in cerebral spinal fluid of traumatic brain injured patients. The Journal of trauma. 2011 Nov; 71(5):1211-8. doi: 10.1097/ta.0b013e3182092c62. [PMID: 21427623]
  • Undurti N Das, N Madhavi. Effect of polyunsaturated fatty acids on drug-sensitive and resistant tumor cells in vitro. Lipids in health and disease. 2011 Sep; 10(?):159. doi: 10.1186/1476-511x-10-159. [PMID: 21917129]
  • Tengis S Pavlov, Daria V Ilatovskaya, Vladislav Levchenko, David L Mattson, Richard J Roman, Alexander Staruschenko. Effects of cytochrome P-450 metabolites of arachidonic acid on the epithelial sodium channel (ENaC). American journal of physiology. Renal physiology. 2011 Sep; 301(3):F672-81. doi: 10.1152/ajprenal.00597.2010. [PMID: 21697242]
  • Janny C de Grauw, Chris H A van de Lest, Paul René van Weeren. A targeted lipidomics approach to the study of eicosanoid release in synovial joints. Arthritis research & therapy. 2011 Jul; 13(4):R123. doi: 10.1186/ar3427. [PMID: 21794148]
  • T Maaløe, E B Schmidt, M Svensson, I V Aardestrup, J H Christensen. The effect of n-3 polyunsaturated fatty acids on leukotriene B₄ and leukotriene B₅ production from stimulated neutrophil granulocytes in patients with chronic kidney disease. Prostaglandins, leukotrienes, and essential fatty acids. 2011 Jul; 85(1):37-41. doi: 10.1016/j.plefa.2011.04.004. [PMID: 21530211]
  • Undurti N Das. Lipoxins as biomarkers of lupus and other inflammatory conditions. Lipids in health and disease. 2011 May; 10(?):76. doi: 10.1186/1476-511x-10-76. [PMID: 21569625]
  • Robert E Carroll, Richard V Benya, Danielle Kim Turgeon, Shaiju Vareed, Malloree Neuman, Luz Rodriguez, Madhuri Kakarala, Philip M Carpenter, Christine McLaren, Frank L Meyskens, Dean E Brenner. Phase IIa clinical trial of curcumin for the prevention of colorectal neoplasia. Cancer prevention research (Philadelphia, Pa.). 2011 Mar; 4(3):354-64. doi: 10.1158/1940-6207.capr-10-0098. [PMID: 21372035]
  • Gabrielle Fredman, Sungwhan F Oh, Srinivas Ayilavarapu, Hatice Hasturk, Charles N Serhan, Thomas E Van Dyke. Impaired phagocytosis in localized aggressive periodontitis: rescue by Resolvin E1. PloS one. 2011; 6(9):e24422. doi: 10.1371/journal.pone.0024422. [PMID: 21935407]
  • Swarup K Chakrabarti, Yeshao Wen, Anca D Dobrian, Banumathi K Cole, Qian Ma, Hong Pei, Michael D Williams, Melissa H Bevard, George E Vandenhoff, Susanna R Keller, Jiali Gu, Jerry L Nadler. Evidence for activation of inflammatory lipoxygenase pathways in visceral adipose tissue of obese Zucker rats. American journal of physiology. Endocrinology and metabolism. 2011 Jan; 300(1):E175-87. doi: 10.1152/ajpendo.00203.2010. [PMID: 20978234]
  • Dong Hyun Kim, Luca Vanella, Kazuyoshi Inoue, Angela Burgess, Katherine Gotlinger, Vijaya Lingam Manthati, Sreenivasulu Reddy Koduru, Darryl C Zeldin, John R Falck, Michal L Schwartzman, Nader G Abraham. Epoxyeicosatrienoic acid agonist regulates human mesenchymal stem cell-derived adipocytes through activation of HO-1-pAKT signaling and a decrease in PPARγ. Stem cells and development. 2010 Dec; 19(12):1863-73. doi: 10.1089/scd.2010.0098. [PMID: 20412023]
  • Barbara Dolegowska, Wojciech Blogowski, Krzysztof Safranow, Leszek Domanski, Katarzyna Jakubowska, Maria Olszewska. Lipoxygenase-derived hydroxyeicosatetraenoic acids--novel perioperative markers of early post-transplant allograft function?. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2010 Dec; 25(12):4061-7. doi: 10.1093/ndt/gfq320. [PMID: 20530808]
  • Dipak Panigrahy, Arja Kaipainen, Emily R Greene, Sui Huang. Cytochrome P450-derived eicosanoids: the neglected pathway in cancer. Cancer metastasis reviews. 2010 Dec; 29(4):723-35. doi: 10.1007/s10555-010-9264-x. [PMID: 20941528]
  • Oliver Jung, Felix Jansen, Anja Mieth, Eduardo Barbosa-Sicard, Rainer U Pliquett, Andrea Babelova, Christophe Morisseau, Sung H Hwang, Cindy Tsai, Bruce D Hammock, Liliana Schaefer, Gerd Geisslinger, Kerstin Amann, Ralf P Brandes. Inhibition of the soluble epoxide hydrolase promotes albuminuria in mice with progressive renal disease. PloS one. 2010 Aug; 5(8):e11979. doi: 10.1371/journal.pone.0011979. [PMID: 20694143]
  • Satoshi Imaizumi, Victor Grijalva, Mohamad Navab, Brian J Van Lenten, Alan C Wagner, G M Anantharamiah, Alan M Fogelman, Srinivasa T Reddy. L-4F differentially alters plasma levels of oxidized fatty acids resulting in more anti-inflammatory HDL in mice. Drug metabolism letters. 2010 Aug; 4(3):139-48. doi: 10.2174/187231210791698438. [PMID: 20642447]
  • Michal Laniado Schwartzman, Pavel Iserovich, Katherine Gotlinger, Lars Bellner, Michael W Dunn, Mauro Sartore, Maria Grazia Pertile, Andrea Leonardi, Sonal Sathe, Ann Beaton, Lynn Trieu, Robert Sack. Profile of lipid and protein autacoids in diabetic vitreous correlates with the progression of diabetic retinopathy. Diabetes. 2010 Jul; 59(7):1780-8. doi: 10.2337/db10-0110. [PMID: 20424229]
  • Marek Sanak, Anna Gielicz, Krzysztof Nagraba, Marek Kaszuba, Jagoda Kumik, Andrew Szczeklik. Targeted eicosanoids lipidomics of exhaled breath condensate in healthy subjects. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Jul; 878(21):1796-800. doi: 10.1016/j.jchromb.2010.05.012. [PMID: 20627827]
  • Christopher P Thomas, Lloyd T Morgan, Benjamin H Maskrey, Robert C Murphy, Hartmut Kühn, Stanley L Hazen, Alison H Goodall, Hassan A Hamali, Peter W Collins, Valerie B O'Donnell. Phospholipid-esterified eicosanoids are generated in agonist-activated human platelets and enhance tissue factor-dependent thrombin generation. The Journal of biological chemistry. 2010 Mar; 285(10):6891-903. doi: 10.1074/jbc.m109.078428. [PMID: 20061396]
  • M D Brown, C Hart, E Gazi, P Gardner, N Lockyer, N Clarke. Influence of omega-6 PUFA arachidonic acid and bone marrow adipocytes on metastatic spread from prostate cancer. British journal of cancer. 2010 Jan; 102(2):403-13. doi: 10.1038/sj.bjc.6605481. [PMID: 19997104]
  • Gail E Grant, Joshua Rokach, William S Powell. 5-Oxo-ETE and the OXE receptor. Prostaglandins & other lipid mediators. 2009 Sep; 89(3-4):98-104. doi: 10.1016/j.prostaglandins.2009.05.002. [PMID: 19450703]
  • Gazala N Khan, Michael A Gorin, Devin Rosenthal, Quintin Pan, Li Wei Bao, Zhi Fen Wu, Robert A Newman, Alison D Pawlus, Peiying Yang, Ephraim P Lansky, Sofia D Merajver. Pomegranate fruit extract impairs invasion and motility in human breast cancer. Integrative cancer therapies. 2009 Sep; 8(3):242-53. doi: 10.1177/1534735409341405. [PMID: 19815594]
  • Wenying Jian, Seon Hwa Lee, Michelle V Williams, Ian A Blair. 5-Lipoxygenase-mediated endogenous DNA damage. The Journal of biological chemistry. 2009 Jun; 284(25):16799-16807. doi: 10.1074/jbc.m109.011841. [PMID: 19390118]
  • Barbara Dołegowska, Wojciech Błogowski, Karolina Kedzierska, Krzysztof Safranow, Katarzyna Jakubowska, Maria Olszewska, Monika Rać, Dariusz Chlubek, Kazimierz Ciechanowski. Platelets arachidonic acid metabolism in patients with essential hypertension. Platelets. 2009 Jun; 20(4):242-9. doi: 10.1080/09537100902849836. [PMID: 19440924]
  • Talat Roome, Ahsana Dar, Sabira Naqvi, Shamsher Ali, Muhammad Iqbal Choudhary. Aegiceras corniculatum extract suppresses initial and late phases of inflammation in rat paw and attenuates the production of eicosanoids in rat neutrophils and human platelets. Journal of ethnopharmacology. 2008 Nov; 120(2):248-54. doi: 10.1016/j.jep.2008.08.025. [PMID: 18809484]
  • Lu Zhao, Nan Zeng, Yong-xin Tang, Xiao-shuai Liu, Xuan Yang, Li-ping Qu. [Effect of herba schizonepetae volatile oil (STO) on activity of 5-lipoxygenase in rat thoracic cavity leukocytes]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2008 Sep; 33(17):2154-7. doi: ". [PMID: 19066064]
  • Thomas G Brock. Capturing proteins that bind polyunsaturated fatty acids: demonstration using arachidonic acid and eicosanoids. Lipids. 2008 Feb; 43(2):161-9. doi: 10.1007/s11745-007-3136-3. [PMID: 18084788]
  • Paul Rubin, Karl W Mollison. Pharmacotherapy of diseases mediated by 5-lipoxygenase pathway eicosanoids. Prostaglandins & other lipid mediators. 2007 May; 83(3):188-97. doi: 10.1016/j.prostaglandins.2007.01.005. [PMID: 17481554]
  • Soojin Park, Marie Yeo, Joo-Hyun Jin, Kee-Myung Lee, Sung Soo Kim, Sang Yoon Choi, Ki-Baik Hahm. Inhibitory activities and attenuated expressions of 5-LOX with red ginseng in Helicobacter pylori-infected gastric epithelial cells. Digestive diseases and sciences. 2007 Apr; 52(4):973-82. doi: 10.1007/s10620-006-9440-6. [PMID: 17333352]
  • Karl-Rudolf Erlemann, Chantal Cossette, Sylvie Gravel, Alain Lesimple, Gue-Jae Lee, Goutam Saha, Joshua Rokach, William S Powell. Airway epithelial cells synthesize the lipid mediator 5-oxo-ETE in response to oxidative stress. Free radical biology & medicine. 2007 Mar; 42(5):654-64. doi: 10.1016/j.freeradbiomed.2006.12.006. [PMID: 17291989]
  • George B Lenon, Charlie C L Xue, David F Story, Frank C K Thien, Sarah McPhee, Chun G Li. Inhibition of release of inflammatory mediators in primary and cultured cells by a Chinese herbal medicine formula for allergic rhinitis. Chinese medicine. 2007 Feb; 2(?):2. doi: 10.1186/1749-8546-2-2. [PMID: 17302969]
  • Peiying Yang, Carrie Cartwright, Diana Chan, Mary Vijjeswarapu, Jibin Ding, Robert A Newman. Zyflamend-mediated inhibition of human prostate cancer PC3 cell proliferation: effects on 12-LOX and Rb protein phosphorylation. Cancer biology & therapy. 2007 Feb; 6(2):228-36. doi: 10.4161/cbt.6.2.3624. [PMID: 17218785]
  • L Cerioni, O Cantoni. ERK1/2 regulates two sequential steps promoting monocyte survival to peroxynitrite. Journal of cellular physiology. 2007 Jan; 210(1):177-82. doi: 10.1002/jcp.20837. [PMID: 16998804]
  • Francesca Sanna, Rosa Rita Bonatesta, Bruno Frongia, Sabrina Uda, Sebastiano Banni, Maria Paola Melis, Maria Collu, Clelia Madeddu, Roberto Serpe, Silvana Puddu, Giovanna Porcu, Sandra Dessì, Barbara Batetta. Production of inflammatory molecules in peripheral blood mononuclear cells from severely glucose-6-phosphate dehydrogenase-deficient subjects. Journal of vascular research. 2007; 44(4):253-63. doi: 10.1159/000100903. [PMID: 17361089]
  • Diana Nieves, Juan José Moreno. Hydroxyeicosatetraenoic acids released through the cytochrome P-450 pathway regulate 3T6 fibroblast growth. Journal of lipid research. 2006 Dec; 47(12):2681-9. doi: 10.1194/jlr.m600212-jlr200. [PMID: 16980726]
  • B Dołegowska, E Pikuła, K Safranow, M Olszewska, K Jakubowska, D Chlubek, P Gutowski. Metabolism of eicosanoids and their action on renal function during ischaemia and reperfusion: the effect of alprostadil. Prostaglandins, leukotrienes, and essential fatty acids. 2006 Dec; 75(6):403-11. doi: 10.1016/j.plefa.2006.07.016. [PMID: 17011760]
  • Cecilia Berg, Sven Hammarström, Helena Herbertsson, Eva Lindström, Ann-Charlotte Svensson, Mats Söderström, Pentti Tengvall, Torbjörn Bengtsson. Platelet-induced growth of human fibroblasts is associated with an increased expression of 5-lipoxygenase. Thrombosis and haemostasis. 2006 Nov; 96(5):652-9. doi: . [PMID: 17080223]
  • Sarah Chouinard, Georges Pelletier, Alain Bélanger, Olivier Barbier. Isoform-specific regulation of uridine diphosphate-glucuronosyltransferase 2B enzymes in the human prostate: differential consequences for androgen and bioactive lipid inactivation. Endocrinology. 2006 Nov; 147(11):5431-42. doi: 10.1210/en.2006-0229. [PMID: 16887906]
  • Ilaria Tommasini, Andrea Guidarelli, Letizia Palomba, Liana Cerioni, Orazio Cantoni. 5-Hydroxyeicosatetraenoic acid is a key intermediate of the arachidonate-dependent protective signaling in monocytes/macrophages exposed to peroxynitrite. Journal of leukocyte biology. 2006 Oct; 80(4):929-38. doi: 10.1189/jlb.0406240. [PMID: 16885503]
  • Samuel F Lockwood, Marc S Penn, Stanley L Hazen, Zsolt Bikádi, Ferenc Zsila. The effects of oral Cardax (disodium disuccinate astaxanthin) on multiple independent oxidative stress markers in a mouse peritoneal inflammation model: influence on 5-lipoxygenase in vitro and in vivo. Life sciences. 2006 Jun; 79(2):162-74. doi: 10.1016/j.lfs.2005.12.052. [PMID: 16466747]
  • M D Brown, C A Hart, E Gazi, S Bagley, N W Clarke. Promotion of prostatic metastatic migration towards human bone marrow stoma by Omega 6 and its inhibition by Omega 3 PUFAs. British journal of cancer. 2006 Mar; 94(6):842-53. doi: 10.1038/sj.bjc.6603030. [PMID: 16523199]
  • Robert E Carraway, Sazzad Hassan, David E Cochrane. Regulation of neurotensin receptor function by the arachidonic acid-lipoxygenase pathway in prostate cancer PC3 cells. Prostaglandins, leukotrienes, and essential fatty acids. 2006 Feb; 74(2):93-107. doi: 10.1016/j.plefa.2005.11.005. [PMID: 16406549]
  • Manohar V Kulkarni, Geeta M Kulkarni, Chao-Hsiung Lin, Chung-Ming Sun. Recent advances in coumarins and 1-azacoumarins as versatile biodynamic agents. Current medicinal chemistry. 2006; 13(23):2795-818. doi: 10.2174/092986706778521968. [PMID: 17073630]
  • Joo-Heon Yoon, Seung Joon Baek. Molecular targets of dietary polyphenols with anti-inflammatory properties. Yonsei medical journal. 2005 Oct; 46(5):585-96. doi: 10.3349/ymj.2005.46.5.585. [PMID: 16259055]
  • Uzzal Roy, Robert Joshua, Russell L Stark, Michael Balazy. Cytochrome P450/NADPH-dependent biosynthesis of 5,6-trans-epoxyeicosatrienoic acid from 5,6-trans-arachidonic acid. The Biochemical journal. 2005 Sep; 390(Pt 3):719-27. doi: 10.1042/bj20050681. [PMID: 15916533]
  • William S Powell, Joshua Rokach. Biochemistry, biology and chemistry of the 5-lipoxygenase product 5-oxo-ETE. Progress in lipid research. 2005 Mar; 44(2-3):154-83. doi: 10.1016/j.plipres.2005.04.002. [PMID: 15893379]
  • Jennifer S Dickinson Zimmer, Douglas F Dyckes, David A Bernlohr, Robert C Murphy. Fatty acid binding proteins stabilize leukotriene A4: competition with arachidonic acid but not other lipoxygenase products. Journal of lipid research. 2004 Nov; 45(11):2138-44. doi: 10.1194/jlr.m400240-jlr200. [PMID: 15342681]
  • N Satya Prasad, R Raghavendra, B R Lokesh, K Akhilender Naidu. Spice phenolics inhibit human PMNL 5-lipoxygenase. Prostaglandins, leukotrienes, and essential fatty acids. 2004 Jun; 70(6):521-8. doi: 10.1016/j.plefa.2003.11.006. [PMID: 15120715]
  • John F Teiber, Dragomir I Draganov, Bert N La Du. Lactonase and lactonizing activities of human serum paraoxonase (PON1) and rabbit serum PON3. Biochemical pharmacology. 2003 Sep; 66(6):887-96. doi: 10.1016/s0006-2952(03)00401-5. [PMID: 12963475]
  • Ingrid Beck-Speier, Niru Dayal, Claudio Denzlinger, Christopher Haberl, Konrad L Maier, Axel Ziesenis, Joachim Heyder. Sulfur-related air pollutants induce the generation of platelet-activating factor, 5-lipoxygenase- and cyclooxygenase-products in canine alveolar macrophages via activation of phospholipases A2. Prostaglandins & other lipid mediators. 2003 Jul; 71(3-4):217-34. doi: 10.1016/s1098-8823(03)00041-8. [PMID: 14518563]
  • Thomas G Brock, Robert W McNish, Peter Mancuso, Michael J Coffey, Marc Peters-Golden. Prolonged lipopolysaccharide inhibits leukotriene synthesis in peritoneal macrophages: mediation by nitric oxide and prostaglandins. Prostaglandins & other lipid mediators. 2003 Jul; 71(3-4):131-45. doi: 10.1016/s1098-8823(03)00036-4. [PMID: 14518557]
  • Simona Zarini, Robert C Murphy. Biosynthesis of 5-oxo-6,8,11,14-eicosatetraenoic acid from 5-hydroperoxyeicosatetraenoic acid in the murine macrophage. The Journal of biological chemistry. 2003 Mar; 278(13):11190-6. doi: 10.1074/jbc.m208496200. [PMID: 12547823]
  • Harry E Grates, Richard M McGowen, Smiti V Gupta, John R Falck, Thomas R Brown, Denis M Callewaert, Diane M Sasaki. Quantification of 20-hydroxyeicosatetraenoic acid by colorimetric competitive enzyme linked immunosorbent assay. Journal of biosciences. 2003 Feb; 28(1):109-13. doi: 10.1007/bf02970140. [PMID: 12682433]
  • Angela M Bentes de Souza, Michael Scott Rogers, Chi Chiu Wang, Pong Mo Yuen, Pui Shan Ng. Comparison of peritoneal oxidative stress during laparoscopy and laparotomy. The Journal of the American Association of Gynecologic Laparoscopists. 2003 Feb; 10(1):65-74. doi: 10.1016/s1074-3804(05)60237-x. [PMID: 12554997]
  • Ayumi Hirano, Yuko Namatame, Eiichi Wakaizumi, Yuka Matsuno, Masao Sugawara. Arachidonic acid-induced channel- and carrier-type ion transport across planar bilayer lipid membranes. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2003 Feb; 19(2):191-7. doi: 10.2116/analsci.19.191. [PMID: 12608744]
  • I A Kudryavtsev, O D Golenko, M V Gudkova, N V Myasishcheva. Arachidonic acid metabolism in growth control of A549 human lung adenocarcinoma cells. Biochemistry. Biokhimiia. 2002 Sep; 67(9):1021-6. doi: 10.1023/a:1020526119866. [PMID: 12387716]
  • Takeshi Hosoi, Yutaka Koguchi, Emiko Sugikawa, Aiko Chikada, Koji Ogawa, Naoki Tsuda, Naoki Suto, Shiho Tsunoda, Tomoyasu Taniguchi, Tetsuo Ohnuki. Identification of a novel human eicosanoid receptor coupled to G(i/o). The Journal of biological chemistry. 2002 Aug; 277(35):31459-65. doi: 10.1074/jbc.m203194200. [PMID: 12065583]
  • M El-Dakhakhny, N J Madi, N Lembert, H P T Ammon. Nigella sativa oil, nigellone and derived thymoquinone inhibit synthesis of 5-lipoxygenase products in polymorphonuclear leukocytes from rats. Journal of ethnopharmacology. 2002 Jul; 81(2):161-4. doi: 10.1016/s0378-8741(02)00051-x. [PMID: 12065147]
  • Hiroaki Taniguchi, Yoshihisa Uenoyama, Yoko Miyamoto, Kiyoshi Okuda. The lipoxygenase pathways are involved in LH-stimulated progesterone production in bovine corpus luteum. Prostaglandins & other lipid mediators. 2002 Jan; 67(1):49-60. doi: 10.1016/s0090-6980(01)00174-5. [PMID: 11789897]
  • J T O'Flaherty, B A Chadwell, M W Kearns, S Sergeant, L W Daniel. Protein kinases C translocation responses to low concentrations of arachidonic acid. The Journal of biological chemistry. 2001 Jul; 276(27):24743-50. doi: 10.1074/jbc.m101093200. [PMID: 11328812]
  • S Tavakoli, M J Cowan, T Benfield, C Logun, J H Shelhamer. Prostaglandin E(2)-induced interleukin-6 release by a human airway epithelial cell line. American journal of physiology. Lung cellular and molecular physiology. 2001 Jan; 280(1):L127-33. doi: 10.1152/ajplung.2001.280.1.l127. [PMID: 11133502]
  • G Di Girolamo, A Franchi, A R De Los Santos, M L Martí, M Farina, M A Fernández de Gimeno. [Effect of nonsteroidal antiinflammatory drugs on colonic lipoxygenase and cyclooxygenase activities from patients with colonic neoplasia]. Medicina. 2001; 61(5 Pt 1):566-72. doi: NULL. [PMID: 11721323]
  • G M Halpern. Anti-inflammatory effects of a stabilized lipid extract of Perna canaliculus (Lyprinol). Allergie et immunologie. 2000 Sep; 32(7):272-8. doi: ". [PMID: 11094640]
  • S W Hwang, H Cho, J Kwak, S Y Lee, C J Kang, J Jung, S Cho, K H Min, Y G Suh, D Kim, U Oh. Direct activation of capsaicin receptors by products of lipoxygenases: endogenous capsaicin-like substances. Proceedings of the National Academy of Sciences of the United States of America. 2000 May; 97(11):6155-60. doi: 10.1073/pnas.97.11.6155. [PMID: 10823958]
  • A Franchi, G Di Girolamo, M Farina, A R de los Santos, M L Martí, M A Gimeno. [Differential action of non-steroidal antiinflammatory drugs on human gallbladder cyclooxygenase and lipoxygenase]. Medicina. 2000; 60(5 Pt 1):580-6. doi: NULL. [PMID: 11188896]
  • C Chavis, L Fraissinet, P Chanez, E Thomas, J Bousquet. A method for the measurement of plasma hydroxyeicosatetraenoic acid levels. Analytical biochemistry. 1999 Jun; 271(1):105-8. doi: 10.1006/abio.1999.4113. [PMID: 10361015]
  • M Dadaian, P Westlund. Albumin modifies the metabolism of hydroxyeicosatetraenoic acids via 12-lipoxygenase in human platelets. Journal of lipid research. 1999 May; 40(5):940-7. doi: . [PMID: 10224163]
  • M Dadaian, P Westlund. Eicosanoid metabolism in human platelets is modified by albumin. Advances in experimental medicine and biology. 1999; 469(?):23-7. doi: 10.1007/978-1-4615-4793-8_4. [PMID: 10667305]
  • J T O'Flaherty, J S Taylor, M J Thomas. Receptors for the 5-oxo class of eicosanoids in neutrophils. The Journal of biological chemistry. 1998 Dec; 273(49):32535-41. doi: 10.1074/jbc.273.49.32535. [PMID: 9829988]
  • F Bucar, M Resch, R Bauer, M Burits, E Knauder, M Schubert-Zsilavecz. 5-Methylflavasperone and rhamnetin from Guiera senegalensis and their antioxidative and 5-lipoxygenase inhibitory activity. Die Pharmazie. 1998 Dec; 53(12):875-8. doi: . [PMID: 9879572]