GENERATION OF ALPHA-HYDROXYALDEHYDIC COMPOUNDS IN THE COURSE OF LIPID-PEROXIDATION

Based on O-18-labeling experiments a general scheme for the generation of hydroxy aldehydic compounds in the course of lipid peroxidation of linoleic acid is developed. Key intermediates are obviously dioxygena ted fatty acids, since after reduction with either NaBH4 or Rh/H-2 1,2 . and 1,6 dihydroxy fatty acids can be identified. The postulated mech anism not only explains the formation of 2-hydroxyalkanals but also su pports earlier hypothesis concerning the generation of 1-hydroxyalkena ls. In addition it predicted the occurrence of (n - 1)-hydroxy-n-oxo f atty acids as additional oxidation products. A search for these previo usly unknown autoxidation products of linoleic acid was indeed success ful.