17(R)-HDHA (BioDeep_00000018508)

   

human metabolite Endogenous blood metabolite natural product


代谢物信息卡片


(4Z,7Z,10Z,13Z,15E,19Z)-17-Hydroxydocosa-4,7,10,13,15,19-hexaenoic acid

化学式: C22H32O3 (344.2351)
中文名称: 17-羟化二十二烷六烯酸
谱图信息: 最多检出来源 Homo sapiens(blood) 41.13%

Reviewed

Last reviewed on 2024-10-24.

Cite this Page

17(R)-HDHA. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/17(r)-hdha (retrieved 2024-12-26) (BioDeep RN: BioDeep_00000018508). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC/C=C\CC(/C=C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O)O
InChI: InChI=1S/C22H32O3/c1-2-3-15-18-21(23)19-16-13-11-9-7-5-4-6-8-10-12-14-17-20-22(24)25/h3,5-8,11-16,19,21,23H,2,4,9-10,17-18,20H2,1H3,(H,24,25)/b7-5-,8-6-,13-11-,14-12-,15-3-,19-16+

描述信息

Docosahexaenoic acid (DHA) is a omega-3 essential fatty acid that reduces the incidence and severity of a number of diseases. Recently, a novel series of DHA-derived lipid mediators with potent protective actions has been identified. In this study we demonstrate that dietary amplification of these DHA-derived products protects the liver from necroinflammatory injury. In vitro, supplementation of hepatocytes with DHA significantly reduced hydrogen peroxide-induced DNA damage, evaluated by the "comet assay," and oxidative stress, determined by measurement of malondialdehyde levels. In vivo, dietary supplementation of mice with DHA ameliorated carbon tetrachloride-induced necroinflammatory damage. In addition, hepatic cyclooxygenase-2 expression and PGE2 levels were significantly reduced in mice fed DHA-enriched diets. In these animals, increased hepatic formation of DHA-derived lipid mediators (i.e., 17S-hydroxy-DHA (17S-HDHA) and protectin D1) was detected by HPLC-gas chromatography/mass spectrometry analysis. Consistent with these findings, synthetic 17-HDHA abrogated genotoxic and oxidative damage in hepatocytes and decreased TNF-alpha release and 5-lipoxygenase expression in macrophages. In a transactivation assay, 17-HDHA acted in a concentration-dependent manner as a PPARgamma agonist. Taken together, these findings identify a potential role for DHA-derived products, specifically 17S-HDHA and protectin D1, in mediating the protective effects of dietary DHA in necroinflammatory liver injury. (PMID: 17056761). This fatty acyl belongs to the main class of docosanoids. (Lipid Maps).
Docosahexaenoic acid (DHA) is a omega-3 essential fatty acid that reduces the incidence and severity of a number of diseases. Recently, a novel series of DHA-derived lipid mediators with potent protective actions has been identified. In this study we demonstrate that dietary amplification of these DHA-derived products protects the liver from necroinflammatory injury. In vitro, supplementation of hepatocytes with DHA significantly reduced hydrogen peroxide-induced DNA damage, evaluated by the "comet assay," and oxidative stress, determined by measurement of malondialdehyde levels. In vivo, dietary supplementation of mice with DHA ameliorated carbon tetrachloride-induced necroinflammatory damage. In addition, hepatic cyclooxygenase-2 expression and PGE2 levels were significantly reduced in mice fed DHA-enriched diets. In these animals, increased hepatic formation of DHA-derived lipid mediators (i.e., 17S-hydroxy-DHA (17S-HDHA) and protectin D1) was detected by HPLC-gas chromatography/mass spectrometry analysis. Consistent with these findings, synthetic 17-HDHA abrogated genotoxic and oxidative damage in hepatocytes and decreased TNF-alpha release and 5-lipoxygenase expression in macrophages. In a transactivation assay, 17-HDHA acted in a concentration-dependent manner as a PPARgamma agonist. Taken together, these findings identify a potential role for DHA-derived products, specifically 17S-HDHA and protectin D1, in mediating the protective effects of dietary DHA in necroinflammatory liver injury. (PMID: 17056761)

同义名列表

19 个代谢物同义名

(4Z,7Z,10Z,13Z,15E,19Z)-17-Hydroxydocosa-4,7,10,13,15,19-hexaenoic acid; (4Z,7Z,10Z,13Z,15E,19Z)-17-Hydroxydocosa-4,7,10,13,15,19-hexaenoate; (e,Z,Z,Z,Z,Z)-17-Hydroxy-, 4,7,10,13,15,19-docosahexaenoic acid; (e,Z,Z,Z,Z,Z)-17-Hydroxy-, 4,7,10,13,15,19-docosahexaenoate; (+/-)-17-hydroxy-4Z,7Z,10Z,13Z,15E,19Z-docosahexaenoic acid; (+/-)-17-hydroxy-4Z,7Z,10Z,13Z,15E,19Z-docosahexaenoate; (4Z,7Z,10Z,13Z,15E,19Z)-17-Hydroxydocosahexaenoate; 17-Hydroxy-4,7,10,13,15,19-docosahexaenoic acid; 17-Hydroxy-4,7,10,13,15,19-docosahexaenoate; 17-Hydroxydocosahexaenoic acid; 17-Hydroxydocosahexaenoate; 17-Hydroxy-dha; (+/-)-17-HDoHE; 17(R)-HDoHE; 17(R)HDoHE; 17(S)-HDHA; 17-HDoHE; 17-Hdhe; 17-HDHA



数据库引用编号

10 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

41 个相关的代谢反应过程信息。

Reactome(40)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

8 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。

亚细胞结构定位 关联基因列表


文献列表

  • Saeed Alqahtani, Li Xia, Amber Jannasch, Christina Ferreira, Jackeline Franco, Jonathan H Shannahan. Disruption of pulmonary resolution mediators contribute to exacerbated silver nanoparticle-induced acute inflammation in a metabolic syndrome mouse model. Toxicology and applied pharmacology. 2021 11; 431(?):115730. doi: 10.1016/j.taap.2021.115730. [PMID: 34601004]
  • Anne Barden, Michael Phillips, Sujata Shinde, Tomas Corcoran, Trevor A Mori. The effects of perioperative dexamethasone on eicosanoids and mediators of inflammation resolution: A sub-study of the PADDAG trial. Prostaglandins, leukotrienes, and essential fatty acids. 2021 10; 173(?):102334. doi: 10.1016/j.plefa.2021.102334. [PMID: 34455200]
  • Christopher E Ramsden, Daisy Zamora, Keturah R Faurot, Beth MacIntosh, Mark Horowitz, Gregory S Keyes, Zhi-Xin Yuan, Vanessa Miller, Chanee Lynch, Gilson Honvoh, Jinyoung Park, Russell Levy, Anthony F Domenichiello, Angela Johnston, Sharon Majchrzak-Hong, Joseph R Hibbeln, David A Barrow, James Loewke, John M Davis, Andrew Mannes, Olafur S Palsson, Chirayath M Suchindran, Susan A Gaylord, J Douglas Mann. Dietary alteration of n-3 and n-6 fatty acids for headache reduction in adults with migraine: randomized controlled trial. BMJ (Clinical research ed.). 2021 06; 374(?):n1448. doi: 10.1136/bmj.n1448. [PMID: 34526307]
  • 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]
  • Yong-Jian Liu, Hui Li, Yang Tian, Jun Han, Xin-Yang Wang, Xin-Yu Li, Chao Tian, Pu-Hong Zhang, Yu Hao, Fang Gao, Sheng-Wei Jin. PCTR1 ameliorates lipopolysaccharide-induced acute inflammation and multiple organ damage via regulation of linoleic acid metabolism by promoting FADS1/FASDS2/ELOV2 expression and reducing PLA2 expression. Laboratory investigation; a journal of technical methods and pathology. 2020 07; 100(7):904-915. doi: 10.1038/s41374-020-0412-9. [PMID: 32123295]
  • Miranda J Crouch, Rasagna Kosaraju, William Guesdon, Michael Armstrong, Nichole Reisdorph, Raghav Jain, Jenifer Fenton, Saame Raza Shaikh. Frontline Science: A reduction in DHA-derived mediators in male obesity contributes toward defects in select B cell subsets and circulating antibody. Journal of leukocyte biology. 2019 08; 106(2):241-257. doi: 10.1002/jlb.3hi1017-405rr. [PMID: 30576001]
  • Chung-Chih Yang, Cheng-Kuei Chang, Meng-Ting Chang, Lie-Fen Shyur. Plant galactolipid dLGG suppresses lung metastasis of melanoma through deregulating TNF-α-mediated pulmonary vascular permeability and circulating oxylipin dynamics in mice. International journal of cancer. 2018 12; 143(12):3248-3261. doi: 10.1002/ijc.31663. [PMID: 29978476]
  • 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]
  • Anne Barden, Sujata Shinde, Michael Phillips, Lawrence Beilin, Emilie Mas, Jonathan M Hodgson, Ian Puddey, Trevor A Mori. The effects of alcohol on plasma lipid mediators of inflammation resolution in patients with Type 2 diabetes mellitus. Prostaglandins, leukotrienes, and essential fatty acids. 2018 06; 133(?):29-34. doi: 10.1016/j.plefa.2018.04.004. [PMID: 29789130]
  • Roberto Rodriguez-Echevarria, Jose Macias-Barragan, Marcela Parra-Vargas, Judith Rebeca Davila-Rodriguez, Eduardo Amezcua-Galvez, Juan Armendariz-Borunda. Diet switch and omega-3 hydroxy-fatty acids display differential hepatoprotective effects in an obesity/nonalcoholic fatty liver disease model in mice. World journal of gastroenterology. 2018 Jan; 24(4):461-474. doi: 10.3748/wjg.v24.i4.461. [PMID: 29398867]
  • Valene H L See, Emilie Mas, Susan L Prescott, Lawrence J Beilin, Sally Burrows, Anne E Barden, Rae-Chi Huang, Trevor A Mori. Effects of prenatal n-3 fatty acid supplementation on offspring resolvins at birth and 12 years of age: a double-blind, randomised controlled clinical trial. The British journal of nutrition. 2017 Dec; 118(11):971-980. doi: 10.1017/s0007114517002914. [PMID: 29173199]
  • Rasagna Kosaraju, William Guesdon, Miranda J Crouch, Heather L Teague, E Madison Sullivan, Erik A Karlsson, Stacey Schultz-Cherry, Kymberly Gowdy, Lance C Bridges, Lauren R Reese, P Darrell Neufer, Michael Armstrong, Nichole Reisdorph, J Justin Milner, Melinda Beck, Saame Raza Shaikh. B Cell Activity Is Impaired in Human and Mouse Obesity and Is Responsive to an Essential Fatty Acid upon Murine Influenza Infection. Journal of immunology (Baltimore, Md. : 1950). 2017 06; 198(12):4738-4752. doi: 10.4049/jimmunol.1601031. [PMID: 28500069]
  • Guangbi Li, Zhida Chen, Owais M Bhat, Qinghua Zhang, Justine M Abais-Battad, Sabena M Conley, Joseph K Ritter, Pin-Lan Li. NLRP3 inflammasome as a novel target for docosahexaenoic acid metabolites to abrogate glomerular injury. Journal of lipid research. 2017 06; 58(6):1080-1090. doi: 10.1194/jlr.m072587. [PMID: 28404641]
  • D T Robinson, H L Palac, V Baillif, E Van Goethem, M Dubourdeau, L Van Horn, C R Martin. Long chain fatty acids and related pro-inflammatory, specialized pro-resolving lipid mediators and their intermediates in preterm human milk during the first month of lactation. Prostaglandins, leukotrienes, and essential fatty acids. 2017 Jun; 121(?):1-6. doi: 10.1016/j.plefa.2017.05.003. [PMID: 28651692]
  • Junting Huang, James J Burston, Li Li, Sadaf Ashraf, Paul I Mapp, Andrew J Bennett, Srinivasarao Ravipati, Petros Pousinis, David A Barrett, Brigitte E Scammell, Victoria Chapman. Targeting the D Series Resolvin Receptor System for the Treatment of Osteoarthritis Pain. Arthritis & rheumatology (Hoboken, N.J.). 2017 05; 69(5):996-1008. doi: 10.1002/art.40001. [PMID: 27860453]
  • L Malan, J Baumgartner, P C Calder, C M Smuts. Low immune cell ARA and high plasma 12-HETE and 17-HDHA in iron-deficient South African school children with allergy. Prostaglandins, leukotrienes, and essential fatty acids. 2016 07; 110(?):35-41. doi: 10.1016/j.plefa.2016.05.006. [PMID: 27255641]
  • Anne E Barden, Mahin Moghaddami, Emilie Mas, Michael Phillips, Leslie G Cleland, Trevor A Mori. Specialised pro-resolving mediators of inflammation in inflammatory arthritis. Prostaglandins, leukotrienes, and essential fatty acids. 2016 Apr; 107(?):24-9. doi: 10.1016/j.plefa.2016.03.004. [PMID: 27033423]
  • Emilie Mas, Anne Barden, Valerie Burke, Lawrence J Beilin, Gerald F Watts, Rae-Chi Huang, Ian B Puddey, Ashley B Irish, Trevor A Mori. A randomized controlled trial of the effects of n-3 fatty acids on resolvins in chronic kidney disease. Clinical nutrition (Edinburgh, Scotland). 2016 Apr; 35(2):331-336. doi: 10.1016/j.clnu.2015.04.004. [PMID: 25908532]
  • Kathy Stein, Melissa Stoffels, Mariola Lysson, Bianca Schneiker, Oliver Dewald, Gerhard Krönke, Jörg C Kalff, Sven Wehner. A role for 12/15-lipoxygenase-derived proresolving mediators in postoperative ileus: protectin DX-regulated neutrophil extravasation. Journal of leukocyte biology. 2016 Feb; 99(2):231-9. doi: 10.1189/jlb.3hi0515-189r. [PMID: 26292977]
  • Anne E Barden, Emilie Mas, Kevin D Croft, Michael Phillips, Trevor A Mori. Specialized proresolving lipid mediators in humans with the metabolic syndrome after n-3 fatty acids and aspirin. The American journal of clinical nutrition. 2015 Dec; 102(6):1357-64. doi: 10.3945/ajcn.115.116384. [PMID: 26561623]
  • Sesquile Ramon, Steven F Baker, Julie M Sahler, Nina Kim, Eric A Feldsott, Charles N Serhan, Luis Martínez-Sobrido, David J Topham, Richard P Phipps. The specialized proresolving mediator 17-HDHA enhances the antibody-mediated immune response against influenza virus: a new class of adjuvant?. Journal of immunology (Baltimore, Md. : 1950). 2014 Dec; 193(12):6031-40. doi: 10.4049/jimmunol.1302795. [PMID: 25392529]
  • Angelika Neuhofer, Maximilian Zeyda, Daniel Mascher, Bianca K Itariu, Incoronata Murano, Lukas Leitner, Eva E Hochbrugger, Peter Fraisl, Saverio Cinti, Charles N Serhan, Thomas M Stulnig. Impaired local production of proresolving lipid mediators in obesity and 17-HDHA as a potential treatment for obesity-associated inflammation. Diabetes. 2013 Jun; 62(6):1945-56. doi: 10.2337/db12-0828. [PMID: 23349501]
  • Thomas Köhnke, Beate Gomolka, Süleyman Bilal, Xiangzhi Zhou, Yanping Sun, Michael Rothe, Daniel C Baumgart, Karsten H Weylandt. Acetylsalicylic Acid reduces the severity of dextran sodium sulfate-induced colitis and increases the formation of anti-inflammatory lipid mediators. BioMed research international. 2013; 2013(?):748160. doi: 10.1155/2013/748160. [PMID: 24083240]
  • Cheng-Ying Chiu, Beate Gomolka, Cordula Dierkes, Nora R Huang, Maik Schroeder, Martin Purschke, Dieter Manstein, Bindi Dangi, Karsten H Weylandt. Omega-6 docosapentaenoic acid-derived resolvins and 17-hydroxydocosahexaenoic acid modulate macrophage function and alleviate experimental colitis. Inflammation research : official journal of the European Histamine Research Society ... [et al.]. 2012 Sep; 61(9):967-76. doi: 10.1007/s00011-012-0489-8. [PMID: 22618200]
  • Sesquile Ramon, Fei Gao, Charles N Serhan, Richard P Phipps. Specialized proresolving mediators enhance human B cell differentiation to antibody-secreting cells. Journal of immunology (Baltimore, Md. : 1950). 2012 Jul; 189(2):1036-42. doi: 10.4049/jimmunol.1103483. [PMID: 22711890]
  • J F Lima-Garcia, R C Dutra, Kabs da Silva, E M Motta, M M Campos, J B Calixto. The precursor of resolvin D series and aspirin-triggered resolvin D1 display anti-hyperalgesic properties in adjuvant-induced arthritis in rats. British journal of pharmacology. 2011 Sep; 164(2):278-93. doi: 10.1111/j.1476-5381.2011.01345.x. [PMID: 21418187]
  • Allisson Freire Bento, Rafaela Franco Claudino, Rafael Cypriano Dutra, Rodrigo Marcon, João B Calixto. Omega-3 fatty acid-derived mediators 17(R)-hydroxy docosahexaenoic acid, aspirin-triggered resolvin D1 and resolvin D2 prevent experimental colitis in mice. Journal of immunology (Baltimore, Md. : 1950). 2011 Aug; 187(4):1957-69. doi: 10.4049/jimmunol.1101305. [PMID: 21724996]
  • Karsten H Weylandt, Lena F Krause, Beate Gomolka, Cheng-Ying Chiu, Süleyman Bilal, Anja Nadolny, Simon F Waechter, Andreas Fischer, Michael Rothe, Jing X Kang. Suppressed liver tumorigenesis in fat-1 mice with elevated omega-3 fatty acids is associated with increased omega-3 derived lipid mediators and reduced TNF-α. Carcinogenesis. 2011 Jun; 32(6):897-903. doi: 10.1093/carcin/bgr049. [PMID: 21421544]
  • Helena Gleissman, Rong Yang, Kimberly Martinod, Magnus Lindskog, Charles N Serhan, John Inge Johnsen, Per Kogner. Docosahexaenoic acid metabolome in neural tumors: identification of cytotoxic intermediates. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2010 Mar; 24(3):906-15. doi: 10.1096/fj.09-137919. [PMID: 19890019]
  • Iram R Hassan, Karsten Gronert. Acute changes in dietary omega-3 and omega-6 polyunsaturated fatty acids have a pronounced impact on survival following ischemic renal injury and formation of renoprotective docosahexaenoic acid-derived protectin D1. Journal of immunology (Baltimore, Md. : 1950). 2009 Mar; 182(5):3223-32. doi: 10.4049/jimmunol.0802064. [PMID: 19234220]
  • Charles N Serhan, Rong Yang, Kimberly Martinod, Kie Kasuga, Padmini S Pillai, Timothy F Porter, Sungwhan F Oh, Matthew Spite. Maresins: novel macrophage mediators with potent antiinflammatory and proresolving actions. The Journal of experimental medicine. 2009 Jan; 206(1):15-23. doi: 10.1084/jem.20081880. [PMID: 19103881]
  • Ana González-Périz, Anna Planagumà, Karsten Gronert, Rosa Miquel, Marta López-Parra, Esther Titos, Raquel Horrillo, Natàlia Ferré, Ramon Deulofeu, Vicente Arroyo, Juan Rodés, Joan Clària. Docosahexaenoic acid (DHA) blunts liver injury by conversion to protective lipid mediators: protectin D1 and 17S-hydroxy-DHA. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2006 Dec; 20(14):2537-9. doi: 10.1096/fj.06-6250fje. [PMID: 17056761]
  • M Moya, J Beltran, J Colomer. Therapeutic and collateral effects of 25-hydroxycholecalciferol in vitamin D deficiency. European journal of pediatrics. 1977 Dec; 127(1):49-55. doi: 10.1007/bf00465565. [PMID: 23950]