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- Name help_outline prostaglandin H3 Identifier CHEBI:133134 Charge -1 Formula C20H29O5 InChIKeyhelp_outline PVTQTOGPOPGQGE-SAMSIYEGSA-M SMILEShelp_outline [C@@H]1([C@@H]2C[C@H]([C@@H]1/C=C/[C@H](C/C=C\CC)O)OO2)C/C=C\CCCC([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 3 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline prostaglandin E3 Identifier CHEBI:133132 Charge -1 Formula C20H29O5 InChIKeyhelp_outline CBOMORHDRONZRN-QLOYDKTKSA-M SMILEShelp_outline C(\[C@H]1[C@@H](CC([C@@H]1C/C=C\CCCC([O-])=O)=O)O)=C/[C@H](C/C=C\CC)O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:50452 | RHEA:50453 | RHEA:50454 | RHEA:50455 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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The essentiality of arachidonic acid and docosahexaenoic acid.
Le H.D., Meisel J.A., de Meijer V.E., Gura K.M., Puder M.
<h4>Objective</h4>The purpose of this review is to correlate the clinical finding that patients receiving parenteral nutrition with a fish oil-based lipid emulsion do not develop essential fatty acid deficiency (EFAD) with an experimental murine model, thus showing that arachidonic acid (AA) and d ... >> More
<h4>Objective</h4>The purpose of this review is to correlate the clinical finding that patients receiving parenteral nutrition with a fish oil-based lipid emulsion do not develop essential fatty acid deficiency (EFAD) with an experimental murine model, thus showing that arachidonic acid (AA) and docosahexaenoic acid (DHA) are likely to be the essential fatty acids.<h4>Background</h4>Conventional belief is that linoleic acid (LA, omega-6) and alpha-linolenic acid (ALA, omega-3) are the essential fatty acids (EFAs). We have shown that a fish oil-based lipid emulsion containing AA (omega-6) and docosahexaenoic acid (omega-3) and insignificant quantities of LA and ALA is efficacious in the treatment of parenteral nutrition-associated liver disease (PNALD), a major cause of liver-related morbidity and mortality. The prospect of using a fish oil-based lipid emulsion as monotherapy has raised concerns of EFAD development, hindering its adoption into clinical practice.<h4>Design</h4>Data from patients in our institution who received PN with a fish oil-based lipid emulsion was reviewed for clinical and biochemical evidence of EFAD, defined as an elevated triene-tetraene ratio (Mead acid/AA>0.2). We also investigated the minimum amount of fish oil required to prevent EFAD in a murine model and determined whether DHA and AA alone can prevent EFAD.<h4>Results</h4>No patients receiving PN with a fish oil-based lipid emulsion in our institution have developed biochemical or clinical evidence of EFAD such as an elevated triene-tetraene ratio, growth retardation or dermatitis. This observation parallels our previously published animal studies, which demonstrated prevention of EFAD when 13% of total calories were from fish oil. Moreover, current work in our laboratory shows that AA and DHA provision alone is sufficient to prevent biochemical and physiologic evidence of EFAD in a murine model.<h4>Conclusions</h4>When dosed appropriately, fish oil-based lipid emulsions contain sufficient EFAs to prevent EFAD. Furthermore, AA and DHA alone may be the true EFAs. << Less
Prostaglandins Leukot. Essent. Fatty Acids 81:165-170(2009) [PubMed] [EuropePMC]
This publication is cited by 2 other entries.
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PUFAs: Structures, Metabolism and Functions.
Wiktorowska-Owczarek A., Berezinska M., Nowak J.Z.
Polyunsaturated fatty acids (PUFAs) include two series of fatty acids: omega-6 and omega-3 series. PUFAs have amphiphatic properties: hydrophilic head and hydrophobic tail. Such structure and other properties of unsaturated fatty acids are responsible for exerting the following biological action: ... >> More
Polyunsaturated fatty acids (PUFAs) include two series of fatty acids: omega-6 and omega-3 series. PUFAs have amphiphatic properties: hydrophilic head and hydrophobic tail. Such structure and other properties of unsaturated fatty acids are responsible for exerting the following biological action: maintaining cell-membrane fluidity, inhib-iting inflammatory processes, decreasing secretion of proinflammatory cytokines by monocytes/macrophages, decreasing susceptibility to ventricular rhythm disorders of the heart, improving functions of vascular endothe-lial cells, inhibiting blood platelet aggregation and decreasing triglyceride synthesis in the liver. In an organism, aracidonic acid (ARA) is converted to prostanoids series 2 (PGE2, PGI2, TXA2) and leukotrienes series 4 (LTB4, LTC4, LTD4) which are endowed with pro-inflammatory potential and are able to induce platelet aggregation and vasoconstriction. The metabolism of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) gives prostanoids series 3 (PGE3, PGI3, TXA3) and leukotrienes series 5 (LTB5, LTC5, LTD5); this group of eicosanoids shows anti-inflammatory, antiplatelet and antiarrhythmic properties. << Less
Adv Clin Exp Med 24:931-941(2015) [PubMed] [EuropePMC]
This publication is cited by 2 other entries.