Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2008-09-15 09:55:09 UTC |
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Update Date | 2021-09-14 15:46:28 UTC |
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HMDB ID | HMDB0010213 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 17-HDoHE |
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Description | 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). |
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Structure | CC\C=C/CC(O)\C=C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O 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+ |
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Synonyms | Value | Source |
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(+/-)-17-hydroxy-4Z,7Z,10Z,13Z,15E,19Z-docosahexaenoic acid | ChEBI | 17-HDHA | ChEBI | 17-Hydroxy-dha | ChEBI | (+/-)-17-hydroxy-4Z,7Z,10Z,13Z,15E,19Z-docosahexaenoate | Generator | (+/-)-17-hdohe | HMDB | (4Z,7Z,10Z,13Z,15E,19Z)-17-Hydroxydocosa-4,7,10,13,15,19-hexaenoate | HMDB | (4Z,7Z,10Z,13Z,15E,19Z)-17-Hydroxydocosa-4,7,10,13,15,19-hexaenoic acid | HMDB | (e,Z,Z,Z,Z,Z)-17-Hydroxy-, 4,7,10,13,15,19-docosahexaenoate | HMDB | (e,Z,Z,Z,Z,Z)-17-Hydroxy-, 4,7,10,13,15,19-docosahexaenoic acid | HMDB | 17-Hdhe | HMDB | 17-Hydroxy-4,7,10,13,15,19-docosahexaenoate | HMDB | 17-Hydroxy-4,7,10,13,15,19-docosahexaenoic acid | HMDB | 17-Hydroxydocosahexaenoate | HMDB | 17-Hydroxydocosahexaenoic acid | HMDB | 17(R)HDoHE | HMDB | 17(S)-HDHA | HMDB | (4Z,7Z,10Z,13Z,15E,19Z)-17-Hydroxydocosahexaenoate | HMDB | 17-HDoHE | ChEBI |
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Chemical Formula | C22H32O3 |
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Average Molecular Weight | 344.4877 |
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Monoisotopic Molecular Weight | 344.23514489 |
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IUPAC Name | (4Z,7Z,10Z,13Z,15E,19Z)-17-hydroxydocosa-4,7,10,13,15,19-hexaenoic acid |
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Traditional Name | 17-HDoHE |
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CAS Registry Number | 90780-52-2 |
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SMILES | CC\C=C/CC(O)\C=C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O |
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InChI Identifier | 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+ |
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InChI Key | SWTYBBUBEPPYCX-VIIQGJSXSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acids and conjugates |
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Direct Parent | Very long-chain fatty acids |
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Alternative Parents | |
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Substituents | - Very long-chain fatty acid
- Hydroxy fatty acid
- Unsaturated fatty acid
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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17-HDoHE,1TMS,isomer #1 | CC/C=C\CC(/C=C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O)O[Si](C)(C)C | 3015.8 | Semi standard non polar | 33892256 | 17-HDoHE,1TMS,isomer #2 | CC/C=C\CC(O)/C=C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C | 2856.2 | Semi standard non polar | 33892256 | 17-HDoHE,2TMS,isomer #1 | CC/C=C\CC(/C=C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2900.2 | Semi standard non polar | 33892256 | 17-HDoHE,1TBDMS,isomer #1 | CC/C=C\CC(/C=C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O)O[Si](C)(C)C(C)(C)C | 3246.9 | Semi standard non polar | 33892256 | 17-HDoHE,1TBDMS,isomer #2 | CC/C=C\CC(O)/C=C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C | 3100.7 | Semi standard non polar | 33892256 | 17-HDoHE,2TBDMS,isomer #1 | CC/C=C\CC(/C=C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3375.1 | Semi standard non polar | 33892256 |
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General References | - Levy BD, Kohli P, Gotlinger K, Haworth O, Hong S, Kazani S, Israel E, Haley KJ, Serhan CN: Protectin D1 is generated in asthma and dampens airway inflammation and hyperresponsiveness. J Immunol. 2007 Jan 1;178(1):496-502. [PubMed:17182589 ]
- Gonzalez-Periz A, Planaguma A, Gronert K, Miquel R, Lopez-Parra M, Titos E, Horrillo R, Ferre N, Deulofeu R, Arroyo V, Rodes J, Claria J: Docosahexaenoic acid (DHA) blunts liver injury by conversion to protective lipid mediators: protectin D1 and 17S-hydroxy-DHA. FASEB J. 2006 Dec;20(14):2537-9. Epub 2006 Oct 20. [PubMed:17056761 ]
- Miller C, Yamaguchi RY, Ziboh VA: Guinea pig epidermis generates putative anti-inflammatory metabolites from fish oil polyunsaturated fatty acids. Lipids. 1989 Dec;24(12):998-1003. [PubMed:2559281 ]
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