[Frontiers in Bioscience 8, e202-217, January 1, 2003]

FATTY ACID ETHYL ESTERS: TOXIC NON-OXIDATIVE METABOLITES OF ETHANOL AND MARKERS OF ETHANOL INTAKE

Catherine A. Best and Michael Laposata

Division of Laboratory Medicine, Department of Pathology, Massachusetts General Hospital and Harvard Medical School, Boston, Massachusetts USA 02114

FIGURE

Figure 1. Oxidative and non-oxidative pathways of ethanol metabolism. Abbreviations - FA, fatty acid; FACoA, fatty acyl coenzyme A; TG, triglyceride.

Figure 2. Current understanding of the synthesis, degradation and toxicities of fatty acid ethyl esters. Abbreviations: FA, fatty acid; FACoA, fatty acyl coenzyme A; FAEE, fatty acid ethyl esters; TG, triglyceride.

Figure 3. Panel A. Serum fatty acid ethyl ester (FAEE) and ethanol levels 24 hours after the initiation of ethanol ingestion and 22.5 hours after cessation. Panel B. Composite time course for total serum fatty acid ethyl ester concentration over a 24-hour period. Each data point represents the mean FAEE values for seven subjects at the indicated time point; results are shown as ± SEM. Ethanol ingestion occurred during the first 1.5 hours of the time course. (Reproduced with permission, JAMA 276,1152-1156, 1996).

Figure 4. Detection and quantitation of fatty acid ethyl esters in serum by single ion monitoring. Gas chromatographic analysis of the ester fraction of lipids extracted from a representative ethanol positive serum sample. Panel A shows a scan of all ions (50-500 AMU) and Panel B shows a scan monitoring single ions of the identical sample. Base ions 67, 88 and 101 are selected for ethyl palmitate (E16:0), ethyl palmitoleate (E16:1), ethyl heptadecanoate (E17:0-the internal standard), ethyl stearate (E18:0), ethyl oleate (E18:1), ethyl linoleate (18:2); and ions 79 and 91 are selected for ethyl arachidonate (E20:4). E16:0, E16:1, E17:0, E18:0, E18:1, E18:2 and E20:4 peaks are shown. Detailed operating conditions of gas chromatographic analysis are described in the FAEE methodology section.

Figure 5. The electron impact spectra generated by GC-MS for selected fatty acid ethyl esters and the corresponding methyl esters. Panel A, ethyl palmitate (E16:0); Panel B, ethyl oleate (E18:1); Panel C, methyl palmitate (M16:0); and Panel D, methyl oleate (M18:1).