| pubmed-article:15869467 | rdf:type | pubmed:Citation | lld:pubmed |
| pubmed-article:15869467 | lifeskim:mentions | umls-concept:C1565860 | lld:lifeskim |
| pubmed-article:15869467 | lifeskim:mentions | umls-concept:C1705323 | lld:lifeskim |
| pubmed-article:15869467 | lifeskim:mentions | umls-concept:C0282636 | lld:lifeskim |
| pubmed-article:15869467 | lifeskim:mentions | umls-concept:C0003695 | lld:lifeskim |
| pubmed-article:15869467 | lifeskim:mentions | umls-concept:C0521033 | lld:lifeskim |
| pubmed-article:15869467 | lifeskim:mentions | umls-concept:C1707310 | lld:lifeskim |
| pubmed-article:15869467 | lifeskim:mentions | umls-concept:C0679622 | lld:lifeskim |
| pubmed-article:15869467 | lifeskim:mentions | umls-concept:C0205314 | lld:lifeskim |
| pubmed-article:15869467 | lifeskim:mentions | umls-concept:C0920591 | lld:lifeskim |
| pubmed-article:15869467 | lifeskim:mentions | umls-concept:C0646199 | lld:lifeskim |
| pubmed-article:15869467 | pubmed:issue | Pt 3 | lld:pubmed |
| pubmed-article:15869467 | pubmed:dateCreated | 2005-9-1 | lld:pubmed |
| pubmed-article:15869467 | pubmed:abstractText | Cyclo-oxygenases-1/2 (COX-1/2) catalyse the oxygenation of AA (arachidonic acid) and related polyunsaturated fatty acids to endoperoxide precursors of prostanoids. COX-1 is referred to as a constitutive enzyme involved in haemostasis, whereas COX-2 is an inducible enzyme expressed in inflammatory diseases and cancer. The fungus Dipodascopsis uninucleata has been shown by us to convert exogenous AA into 3(R)-HETE [3(R)-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid]. 3R-HETE is stereochemically identical with AA, except that a hydroxy group is attached at its C-3 position. Molecular modelling studies with 3-HETE and COX-1/2 revealed a similar enzyme-substrate structure as reported for AA and COX-1/2. Here, we report that 3-HETE is an appropriate substrate for COX-1 and -2, albeit with a lower activity of oxygenation than AA. Oxygenation of 3-HETE by COX-2 produced a novel cascade of 3-hydroxyeicosanoids, as identified with EI (electron impact)-GC-MS, LC-MS-ES (electrospray) and LC-MS-API (atmospheric pressure ionization) methods. Evidence for in vitro production of 3-hydroxy-PGE2 (3-hydroxy-prostaglandin E2) was obtained upon infection of HeLa cells with Candida albicans at an MOI (multiplicity of infection) of 100. Analogous to interaction of AA and aspirin-treated COX-2, 3-HETE was transformed by acetylated COX-2 to 3,15-di-HETE (3,15-dihydroxy-HETE), whereby C-15 showed the (R)-stereochemistry. 3-Hydroxy-PGs are potent biologically active compounds. Thus 3-hydroxy-PGE2 induced interleukin-6 gene expression via the EP3 receptor (PGE2 receptor 3) in A549 cells, and raised cAMP levels via the EP4 receptor in Jurkat cells. Moreover, 3R,15S-di-HETE triggered the opening of the K+ channel in HTM (human trabecular meshwork) cells, as measured by the patch-clamp technique. Since many fatty acid disorders are associated with an 'escape' of 3-hydroxy fatty acids from the b-oxidation cycle, the production of 3-hydroxyeicosanoids may be critical in modulation of effects of endogenously produced eicosanoids. | lld:pubmed |
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| pubmed-article:15869467 | pubmed:language | eng | lld:pubmed |
| pubmed-article:15869467 | pubmed:journal | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:15869467 | pubmed:citationSubset | IM | lld:pubmed |
| pubmed-article:15869467 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
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| pubmed-article:15869467 | pubmed:status | MEDLINE | lld:pubmed |
| pubmed-article:15869467 | pubmed:month | Sep | lld:pubmed |
| pubmed-article:15869467 | pubmed:issn | 1470-8728 | lld:pubmed |
| pubmed-article:15869467 | pubmed:author | pubmed-author:NigamSantoshS | lld:pubmed |
| pubmed-article:15869467 | pubmed:author | pubmed-author:CiccoliRobert... | lld:pubmed |
| pubmed-article:15869467 | pubmed:author | pubmed-author:KockJohan L... | lld:pubmed |
| pubmed-article:15869467 | pubmed:author | pubmed-author:IshdorjGanchi... | lld:pubmed |
| pubmed-article:15869467 | pubmed:author | pubmed-author:PrakashHriday... | lld:pubmed |
| pubmed-article:15869467 | pubmed:author | pubmed-author:SahiShaktiS | lld:pubmed |
| pubmed-article:15869467 | pubmed:author | pubmed-author:SinghSandhyaS | lld:pubmed |
| pubmed-article:15869467 | pubmed:author | pubmed-author:ZafiriouMaria... | lld:pubmed |
| pubmed-article:15869467 | pubmed:issnType | Electronic | lld:pubmed |
| pubmed-article:15869467 | pubmed:day | 15 | lld:pubmed |
| pubmed-article:15869467 | pubmed:volume | 390 | lld:pubmed |
| pubmed-article:15869467 | pubmed:owner | NLM | lld:pubmed |
| pubmed-article:15869467 | pubmed:authorsComplete | Y | lld:pubmed |
| pubmed-article:15869467 | pubmed:pagination | 737-47 | lld:pubmed |
| pubmed-article:15869467 | pubmed:dateRevised | 2009-11-18 | lld:pubmed |
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