Switch to
Predicate | Object |
---|---|
rdf:type | |
lifeskim:mentions | |
pubmed:issue |
43
|
pubmed:dateCreated |
1991-2-22
|
pubmed:abstractText |
We have previously shown that porcine polymorphonuclear leukocytes (PMNL) reduce leukotriene B4 (LTB4) to 10,11-dihydro-LTB4, 10,11-dihydro-12-epi-LTB4, and 10,11-dihydro-12-oxo-LTB4 [Wainwright et al. (1990) Biochemistry 29, 1180-1185]. We have now demonstrated that 12(S)-hydroxy-5,8,10,14-eicosatetraenoic acid [12(S)-HETE] is metabolized by a similar pathway in porcine PMNL. 12(S)-HETE was metabolized to two products that were identified by gas chromatography-mass spectrometry and nuclear magnetic resonance spectroscopy as 12-hydroxy-5,8,14-eicosatrienoic acid (10,11-dihydro-12-HETE) and 12-oxo-5,8,14-eicosatrienoic acid (10,11-dihydro-12-oxo-ETE). Derivatization of 12-hydroxy-5,8,14-eicosatrienoic acid with (R)-(+)-alpha-methoxy-alpha-(trifluoromethyl)phenylacetic acid, followed by chromatography on a silicic acid column, enabled the resolution of 12R and 12S stereoisomers, which were identified by cochromatography with synthetic standards. Incubation of 12(S)-HETE with PMNL for various times revealed that the stereochemistry of the 12-hydroxyl group of 12-hydroxy-5,8,14-eicosatrienoic acid was initially the same as that of 12(S)-HETE. However, after 40 min, 30% of the 12-hydroxy-5,8,14-eicosatrienoic acid had the opposite configuration at C12. 13-Hydroxy-9,11-octadecadienoic acid (13-HODE) was metabolized in a similar fashion by porcine PMNL to 13-hydroxy-9-octadecenoic acid (11,12-dihydro-13-HODE) and 13-oxooctadecenoic acid (11,12-dihydro-13-oxo-ODE). The apparent Km values for the reduction of 12-HETE, LTB4, and 13-HODE were 0.21, 0.28, and 2.22 microM, respectively. All three substrates had the same apparent Vmax [0.029 pmol min-1 (10(6) cells)-1]. Competition experiments between LTB4 and 12-HETE indicated that they were metabolized by the same pathway. Various structurally related compounds were metabolized by porcine PMNL in the order LTB4 = 6-trans-LTB4 greater than 12-epi-6-trans,8-cis-LTB4 greater than 12-epi-6-trans-LTB4 greater than 12-HETE greater than LTB5 greater than 15-HETE = 13-HODE much greater than 5-HETE greater than 9-HODE greater than 20-hydroxy-LTB4 greater than 12-hydroxy-5,8,10-heptadecatrienoic acid. Prostaglandins E2 and F2 alpha were not metabolized to any detectable products by porcine PMNL.
|
pubmed:language |
eng
|
pubmed:journal | |
pubmed:citationSubset |
IM
|
pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/12-Hydroxy-5,8,10,14-eicosatetraenoi...,
http://linkedlifedata.com/resource/pubmed/chemical/13-hydroxy-9,11-octadecadienoic acid,
http://linkedlifedata.com/resource/pubmed/chemical/5,8,11,14-Eicosatetraynoic Acid,
http://linkedlifedata.com/resource/pubmed/chemical/Aldehyde Oxidoreductases,
http://linkedlifedata.com/resource/pubmed/chemical/Fatty Acids,
http://linkedlifedata.com/resource/pubmed/chemical/Fatty Acids, Unsaturated,
http://linkedlifedata.com/resource/pubmed/chemical/Hydroxyeicosatetraenoic Acids,
http://linkedlifedata.com/resource/pubmed/chemical/Leukotriene B4,
http://linkedlifedata.com/resource/pubmed/chemical/Linoleic Acids,
http://linkedlifedata.com/resource/pubmed/chemical/fatty acid reductase
|
pubmed:status |
MEDLINE
|
pubmed:month |
Oct
|
pubmed:issn |
0006-2960
|
pubmed:author | |
pubmed:issnType |
Print
|
pubmed:day |
30
|
pubmed:volume |
29
|
pubmed:owner |
NLM
|
pubmed:authorsComplete |
Y
|
pubmed:pagination |
10126-35
|
pubmed:dateRevised |
2006-11-15
|
pubmed:meshHeading |
pubmed-meshheading:2176862-12-Hydroxy-5,8,10,14-eicosatetraenoic Acid,
pubmed-meshheading:2176862-5,8,11,14-Eicosatetraynoic Acid,
pubmed-meshheading:2176862-Aldehyde Oxidoreductases,
pubmed-meshheading:2176862-Animals,
pubmed-meshheading:2176862-Fatty Acids,
pubmed-meshheading:2176862-Fatty Acids, Unsaturated,
pubmed-meshheading:2176862-Hydroxyeicosatetraenoic Acids,
pubmed-meshheading:2176862-Leukotriene B4,
pubmed-meshheading:2176862-Linoleic Acids,
pubmed-meshheading:2176862-Molecular Conformation,
pubmed-meshheading:2176862-Neutrophils,
pubmed-meshheading:2176862-Oxidation-Reduction,
pubmed-meshheading:2176862-Substrate Specificity,
pubmed-meshheading:2176862-Swine
|
pubmed:year |
1990
|
pubmed:articleTitle |
Metabolism of 12(S)-hydroxy-5,8,10,14-eicosatetraenoic acid and other hydroxylated fatty acids by the reductase pathway in porcine polymorphonuclear leukocytes.
|
pubmed:affiliation |
Endocrine Laboratory, Royal Victoria Hospital, Montreal, Quebec, Canada.
|
pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, P.H.S.,
Research Support, Non-U.S. Gov't
|