Linked Life Data

2523946

Source:http://linkedlifedata.com/resource/pubmed/id/2523946

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
2
pubmed:dateCreated
1989-6-16
pubmed:abstractText
Docosahexaenoic acid (22:6(n-3)) was recently shown to be metabolized by liver microsomes to vicinal diol regioisomers. To identify the diols, and to compare their biological actions with those of epoxide precursors, we developed a chemical method to synthesize microgram to milligram amounts of epoxides and corresponding diols. In brief, methylated docosahexaenoate was reacted for 15 min with 0.1 eq m-chloroperoxybenzoic acid. After normal- and reverse-phase high performance liquid chromatography, six products were isolated. The underivatized or hydrogenated products were characterized and identified using capillary gas-liquid chromatography and mass spectrometry. The products were identified as 19,20-, 16,17-, 13,14-, 10,11-, 7,8-, and 4,5-epoxy-docosapentaenoate. Per incubation, the total epoxide yield from 22:6(n-3) was 8.6%. By reincubating unused substrate 10-20 times (cycling), the total epoxide could be increased to 55-70%. As found for epoxides of arachidonic and eicosapentaenoic acids, the yield of individual regioisomers increased as the distance between the targeted double bond and carbomethoxy group increased. Each epoxide regioisomer was hydrolyzed to its corresponding vicinal diol. The gas-liquid chromatographic retention times and mass spectra of the diol products were found to match those of metabolites produced by cytochrome P-450 monooxygenases.
pubmed:grant
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Feb
pubmed:issn
0022-2275
pubmed:author
pubmed:issnType
Print
pubmed:volume
30
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
275-86
pubmed:dateRevised
2008-11-21
pubmed:meshHeading
pubmed:year
1989
pubmed:articleTitle
Synthesis of epoxide and vicinal diol regioisomers from docosahexaenoate methyl esters.
pubmed:affiliation
Hypertension Research Division, Henry Ford Hospital, Detroit, MI 48202.
pubmed:publicationType
Journal Article, Research Support, U.S. Gov't, P.H.S., Research Support, Non-U.S. Gov't