Linked Life Data

2215089

Source:http://linkedlifedata.com/resource/pubmed/id/2215089

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
8
pubmed:dateCreated
1990-11-20
pubmed:abstractText
Eicosapentaenoic acid, a major component of fish oil extracts, was recently shown to be metabolized to vicinal diol regioisomers by renal and hepatic cytochrome P-450 epoxygenases. The diol products were also found in the urine of people ingesting fish oil. In the present report, we developed a chemical method of making milligram amounts of the epoxide intermediates and their diol products. Eicosapentaenoic acid was reacted with 0.1 eq. m-chloroperoxybenzoic acid for 15 min. After normal- and reverse-phase high performance liquid chromatography plus capillary gas chromatography and electron impact mass spectrometry, the products were identified as 17,18-cis-epoxy-eicosa-5,8,11,14-tetraenoic, 14,15-cis-epoxy-eicosa-5,8,11,17-tetraenoic, 11,12-cis-epoxy-eicosa-5,8,14,17-tetraenoic, 8,9-cis-epoxy-eicosa-5,11,14,17-tetraenoic and 5,6-cis-epoxy-eicosa-8,11,14,17-tetraenoic acids. The total epoxide yield from eicosapentaenoate was 10% per incubation. By reincubating (cycling) the unused substrate 10-20 times, the total epoxide yield could be increased to 66-88%. Epoxide regioisomers were not produced in equal amounts; epoxygenation was facilitated as the distance between the target double bond and carbomethoxy group increased. Upon hydrolyzing the epoxides, the gas-chromatographic retention times and mass spectra of the diol products were found to match those of biological metabolites. In addition, each of these standards was rapidly and quantitatively synthesized in an amount (milligram) adequate for biological tests.
pubmed:grant
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Aug
pubmed:issn
0024-4201
pubmed:author
pubmed:issnType
Print
pubmed:volume
25
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
481-90
pubmed:dateRevised
2007-11-14
pubmed:meshHeading
pubmed:year
1990
pubmed:articleTitle
Synthesis and characterization of cytochrome P-450 epoxygenase metabolites of eicosapentaenoic acid.
pubmed:affiliation
Hypertension Research Division, Henry Ford Hospital, Detroit, Michigan 48202.
pubmed:publicationType
Journal Article, Research Support, U.S. Gov't, P.H.S., Research Support, Non-U.S. Gov't