17-HDoHE (BioCAD00000023807)
Metabolite Card
Formula: C22H32O3 (344.2351)
SMILES: CC\C=C/CC(O)\C=C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O
Synonyms [en]
17-HDoHE; (+/-)-17-hydroxy-4Z,7Z,10Z,13Z,15E,19Z-docosahexaenoic acid; 17-Hydroxy-dha; 17-HDHA; (4Z,7Z,10Z,13Z,15E,19Z)-17-Hydroxydocosa-4,7,10,13,15,19-hexaenoic acid; (+/-)-17-hdohe
Last reviewed on 2024-06-28.
Cite this Page
17-HDoHE. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China.
https://biocad_registry.innovation.ac.cn/s/(-)-arctiin
(retrieved
2026-01-03) (CAD Registry RN: BioCAD00000023807). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
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).
DBLinks
- CAS Registry Number: 90780-52-2
- PubChem CID: 6439179
- ChEBI: 72637
- HMDB: HMDB0010213
- LipidMaps: LMFA04000032
- KEGG:
- BioCyc:
- NCBI MeSH: 17-hydroxy-4,7,10,13,15,19-docosahexaenoic acid
- Wikipedia:
Other DBLinks
- CAS Registry Number: 90780-52-2
- PubChem: 11046191
- PubChem: 6439179
- ChEBI: ChEBI:138640
- ChEBI: ChEBI:72637
- HMDB: HMDB0010213
- LipidMaps: LMFA04000012
- LipidMaps: LMFA04000032
- NCBI MeSH: 17-hydroxy-4,7,10,13,15,19-docosahexaenoic acid
- RefMet: RM0153416
- RefMet: RM0153445
- MoNA: UT000127
- MoNA: UT000128
- MoNA: UT000129
- MoNA: UT000130
- MoNA: UT000131
- MoNA: UT000132
- MoNA: UT000133
- MoNA: UT000134
- MoNA: UT000135
- Metlin: METLIN_36447
Class / Ontology
- WishartLab ClassyFire: [Fatty acids and conjugates] Fatty acids and conjugates
- RefMet: [Docosanoids] Docosanoids
- LipidMaps: [Other Docosanoids [FA0400]] Other Docosanoids [FA0400]
- ChEBI: [CHEBI:72637] (4Z,7Z,10Z,13Z,15E,19Z)-17-hydroxydocosahexaenoic acid
Taxonomy Source
Pathway Synthetic
| pathway id | name |
|---|---|
| WikiPathways:WP5154 | Docosahexaenoic acid oxylipin metabolism |