Previously unknown aldehydic lipid peroxidation compounds of arachidonic acid.
Arachidonic acid was oxidized by iron ascorbate. Samples were withdrawn in time intervals. The aldehydic oxidation products were trapped by preparation of pentafluorbenzyloximes. Their trimethylsilylated derivatives were subjected to analysis by GC/MS. The main aldehydic lipid peroxidation product was found to be the well-known 4-hydroxy-2-nonenal (HNE), but 2-hydroxy heptanal (HH) -- a previously unknown lipid peroxidation product of arachidonic acid -- was detected to be nearly equally abundant. Malondialdehyde (MDA), glyoxal and 2-hydroxy-4-decenal (HDE) were detected to be produced in up to 100 times lower amounts compared to HNE. The amounts of aldehydes increased steadily with time. In addition, n-l-hydroxy-n-oxo acids were detected. Similar aldehydes were obtained by iron ascorbate-induced oxidation of hydroxy acids derived by NaBH4-reduction of 13-hydroperoxy-9-cis-11-trans-octadecadienoic acid. Since this and analogous hydroxy acids (LOHs) are the main biological degradation products of hydroperoxides of unsaturated acids (LOOHs) their further peroxidation seems to be a main source of toxic aldehydes.
Lehrstuhl fr Organische Chemie I, Universitt Bayreuth, Germany.
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Mlakar
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Spiteller
D000081:Acetamides; D000447:Aldehydes / Q000032:analysis* / Q000737:chemistry / Q000378:metabolism; D016718:Arachidonic Acid / Q000378:metabolism*; D001205:Ascorbic Acid / Q000378:metabolism; D002849:Chromatography, Gas; D005463:Fluoroacetates; D005609:Free Radicals / Q000378:metabolism; D006037:Glyoxal / Q000378:metabolism; D006898:Hydroxylamines / Q000378:metabolism; D007202:Indicators and Reagents / Q000378:metabolism; D007700:Kinetics; D015227:Lipid Peroxidation; D008054:Lipid Peroxides / Q000378:metabolism; D008315:Malondialdehyde / Q000378:metabolism; D013058:Mass Spectrometry; D008956:Models, Chemical; D015394:Molecular Structure; D014269:Trifluoroacetic Acid / Q000378:metabolism; D014297:Trimethylsilyl Compounds / Q000378:metabolism; D005466:Fluorocarbons
D000081:Acetamides; D000447:Aldehydes; D016718:Arachidonic Acid; D001205:Ascorbic Acid; D005463:Fluoroacetates; D005609:Free Radicals; D006037:Glyoxal; D006898:Hydroxylamines; D007202:Indicators and Reagents; D008054:Lipid Peroxides; D008315:Malondialdehyde; D014269:Trifluoroacetic Acid; D014297:Trimethylsilyl Compounds; C098838:2-hydroxyheptanal; C086665:N-methyl-N-(trimethylsilyl)trifluoroacetamide; C010277:Florox Reagent; D005466:Fluorocarbons; C027576:4-hydroxy-2-nonenal