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 2024-12-27) (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]
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  • 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]
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  • 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]
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  • 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]
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  • 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]
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