Analysis by fast-atom bombardment tandem mass spectrometry of phosphatidylcholine isolated from heart mitochondrial fractions: Evidence of incorporation of monohydroxylated fatty acyl moieties.

Phosphatidylcholine (PC) is one of the main phospholipids present in mitochondrial membranes. According to current knowledge, the predominant fatty acyl moieties in this phospholipid are 16, 18, 20, or 22 carbon atoms long with chains that contain only carbon and hydrogen atoms. We have conducted a detailed analysis of the fatty acid substituents of the phospholipids present in mitochondrial fractions by using fast-atom bombardment tandem PC extracted from mitochondrial fractions of rat heart. The structure of one of these monohydroxylated fatty acids has been elucidated and corresponded to 12-hydroxy 9-octadecenoic acid. Indications that concern the structure of the five other monohydroxylated fatty acids are presented. These monohydroxylated fatty acyl groups are preferentially associated in the PC molecule with C-18 and C-20 fatty acyl moieties. We present arguments to suggest that the formation of these compounds is probably not due to a free-radical initiated mechanism. The potential implication of these monohydroxylated fatty acids in several physiological functions is suggested by the fact that free hydroxylated fatty acids that are identical or closely related to those found in the mitochondrial fractions possess various biological activities.