Stereochemical analysis of hydroxylated docosahexaenoates produced by human platelets and rat brain homogenate.
The stereochemical configuration of hydroxylated products of docosahexaenoic acid (22:6w3) formed by human platelets and rat brain homogenate were characterized for the first time. Chiral phase HPLC was employed along with autooxidized 22:6w3 as reference material. The 14- and 11-hydroxy 22:6w3 (HDHE) products produced by human platelets were in the S configuration. Rat brain homogenate produced all of the ten possible positional isomers when incubated with 22:6w3. Their retention behavior on the reversed and chiral phase HPLC columns and GC/MS/EI analysis indicated that they were 20-, 17-, 16-, 14-, 13-, 11-, 10-, 8-, 7- and 4-HDHE. However, stereochemical analysis revealed that each positional isomer was a racemic mixture, suggesting that these were not formed by lipoxygenation but mainly by peroxidation process.
Kim
H Y
HY
Section of Analytical Chemistry, LCS, DICBR, NIAAA, Bethesda, MD 20892.
Karanian
J W
JW
Shingu
T
T
Salem
N
N
D000818:Animals; D001792:Blood Platelets / Q000378:metabolism*; D001921:Brain / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D004281:Docosahexaenoic Acids / Q000097:blood / Q000302:isolation & purification / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D008084:Lipoxygenase / Q000097:blood / Q000378:metabolism*; D013058:Mass Spectrometry; D051381:Rats; D013237:Stereoisomerism
D004281:Docosahexaenoic Acids; D008084:Lipoxygenase