335
Views
21
CrossRef citations to date
0
Altmetric
Review Article

Synthesis of fatty acid ethyl esters in mammalian tissues after ethanol exposure: a systematic review of the literature

, , &
Pages 277-299 | Received 23 Jan 2013, Accepted 10 Apr 2013, Published online: 29 May 2013

References

  • Ahmad F, Kaphalia BS, Khan MF, Ansari GAS. (1993). Fatty-acid anilides A new conjugation pathway of aniline. Biochem Arch 9:111–118
  • Aleryani S, Kabakibi A, Cluette-Brown J, Laposata M. (1996). Fatty acid ethyl ester synthase, an enzyme for nonoxidative ethanol metabolism, is present in serum after liver and pancreatic injury. Clin Chem 42:24–27
  • Alhomsi K, Cluette-Brown JE, Laposata M. (2006). Fatty acid ethyl esters in human mononuclear cells: Production by endogenous synthesis greatly exceeds the uptake of preformed ethyl esters. Alcohol Clin Exp Res 30:560–566
  • Ansari GA, Kaphalia BS, Khan MF. (1995). Fatty acid conjugates of xenobiotics. Toxicol Lett 75:1–17
  • Auwarter V, Kiessling B, Pragst F. (2004). Squalene in hair – a natural reference substance for the improved interpretation of fatty acid ethyl ester concentrations with respect to alcohol misuse. For Sci Int 145:149–159
  • Auwarter V, Sporkert F, Hartwig S, et al. (2001). Fatty acid ethyl esters in hair as markers of alcohol consumption. Segmental hair analysis of alcoholics, social drinkers, and teetotalers. Clin Chem 47:2114–2123
  • Baraona E, Pirola RC, Lieber CS. (1975). Acute and chronic effects of ethanol on intestinal lipid metabolism. Biochim Biophys Acta 388:19–28
  • Bearer CF, Gould S, Emerson R, et al. (1992). Fetal alcohol syndrome and fatty acid ethyl esters. Pediatr Res 31:492–495
  • Bearer CF, Jacobson JL, Jacobson SW, et al. (2003). Validation of a new biomarker of fetal exposure to alcohol. J Pediatr 143:463–469
  • Bearer CF, Lee S, Salvator AE, et al. (1999). Ethyl linoleate in meconium: A biomarker for prenatal ethanol exposure. Alcohol Clin Exp Res 23:487–493
  • Bearer CF, Swick AR, Emerson RK. (1995). Fetal activity of fatty acid ethyl ester synthases. Res Commun Alcohol S 16:189–194
  • Bearer CF, Santiago LM, O'Riordan MA, et al. (2005). Fatty acid ethyl esters: Quantitative biomarkers for maternal alcohol consumption. J Pediatr 146:824–830
  • Behonick GS, Vallaro GM, Hodnett CN, et al. (1997). Distribution of fatty acid ethyl esters in long evans rats following acute ethanol ingestion. Toxicol Method 7:17–25
  • Best CA, Cluette-Brown JE, Teruya M, et al. (2003). Red blood cell fatty acid ethyl esters: A significant component of fatty acid ethyl esters in the blood. J Lipid Res 44:612–620
  • Best CA, Laposata M. (2003). Fatty acid ethyl esters: Toxic non-oxidative metabolites of ethanol and markers of ethanol intake. Front Biosci 8:e202–e217
  • Best CA, Sarkola T, Eriksson CJP, et al. (2006). Increased plasma fatty acid ethyl ester levels following inhibition of oxidative metabolism of ethanol by 4-methylpyrazole treatment in human subjects. Alcohol Clin Exp Res 30:1126–1131
  • Bhat HK, Ansari GA. (1990). Cholesterol ester hydrolase mediated conjugation of haloethanols with fatty acids. Chem Res Toxicol 3:311–317
  • Bhopale KK, Wu H, Boor PJ, et al. (2006). Metabolic basis of ethanol-induced hepatic and pancreatic injury in hepatic alcohol dehydrogenase deficient deer mice. Alcohol 39:179–188
  • Bisaga A, Laposata M, Xie S, Evans SM. (2005). Comparison of serum fatty acid ethyl esters and urinary 5-hydroxytryptophol as biochemical markers of recent ethanol consumption. Alcohol Alcohol 40:214–218
  • Bishop JE, Hajra AK. (1984). Biosynthesis of triglyceride and other fatty acyl esters by developing rat brain. J Neurochem 43:1046–1051
  • Bjorntorp P, Depergola G, Sjoberg C, et al. (1990). Alcohol consumption and synthesis of ethyl esters of fatty acids in adipose tissue. J Intern Med 228:557–562
  • Blanco PG, Salem RO, Ollero M, et al. (2005). Ethanol administration to cystic fibrosis knockout mice results in increased fatty acid ethyl ester production. Alcohol Clin Exp Res 29:2039–2045
  • Board P, Smith S, Green J, et al. (1993). Evidence against a relationship between fatty acid ethyl ester synthase and the pi class glutathione s-transferase in humans. J Biol Chem 268:15655–15658
  • Bora PS, Bora NS, Wu X, Lange LG. (1991). Molecular cloning sequencing and expression of human myocardial fatty acid ethyl ester synthase-III cDNA. J Biol Chem 266:16774–16777
  • Bora PS, Guruge BL, Bora NS. (2003). Molecular characterization of human eye and heart fatty acid ethyl ester synthase/carboxylesterase by site-directed mutagenesis. Biochem Biophys Res Commun 312:1094–1098
  • Bora PS, Guruge BL, Miller DD, et al. (1996). Purification and characterization of human heart fatty acid ethyl ester synthase/carboxylesterase. J Mol Cell Cardiol 28:2027–2032
  • Bora PS, Kaliappan S, Xu Q, et al. (2006). Alcohol linked to enhanced angiogenesis in rat model of choroidal neovascularization. FEBS J 273:1403–1414
  • Bora PS, Spilburg CA, Lange LG. (1989a). Identification of a satellite fatty acid ethyl ester synthase from human myocardium as a glutathione s transferase. J Clin Invest 84:1942–1946
  • Bora PS, Spilburg CA, Lange LG. (1989b). Metabolism of ethanol and carcinogens by glutathione transferase. Proc Natl Acad Sci USA 86:4470–4473
  • Bora PS, Spilburg CA, Lange LG. (1989c). Purification to homogeneity and characterization of major fatty acid ethyl ester synthase from human myocardium. FEBS Lett 258:236–239
  • Bora PS, Wu X, Spilburg CA, Lange LG. (1992a). Purification and characterization of fatty acid ethyl ester synthase-II from human myocardium. J Biol Chem 267:13217–13221
  • Bora PS, Wu XL, Lange LG. (1992b). Site-specific mutagenesis of 2 histidine-residues in fatty-acid ethyl-ester synthase-III. Biochem Biophys Res Commun 184:706–711
  • Borucki K, Dierkes J, Wartberg J, et al. (2007). In heavy drinkers, fatty acid ethyl esters remain elevated for up to 99 hours. Alcohol Clin Exp Res 31:423–427
  • Borucki K, Kunstmann S, Dierkes J, et al. (2004). In heavy drinkers fatty acid ethyl esters in the serum are increased for 44 hr after ethanol consumption. Alcoholism Clin Exp Res 28:1102–1106
  • Borucki K, Schreiner R, Dierkes J, et al. (2005). Detection of recent ethanol intake with new markers: Comparison of fatty acid ethyl esters in serum and of ethyl glucuronide and the ratio of 5-hydroxytryptophol to 5-hydroxyindole acetic acid in urine. Alcohol Clin Exp Res 29:781–787
  • Brien JF, Chan D, Green C, et al. (2006). Chronic prenatal ethanol exposure and increased concentration of fatty acid ethyl esters in meconium of term fetal guinea pig. Ther Drug Monit 28:345–350
  • Calabrese V, Bombaci G, Calderone A, Rizza V. (1993). Effects of metadoxine on cellular free fatty acid levels in ethanol treated rats. Int J Tissue React 15:235–243
  • Calabrese V, Calderone A, Ragusa N, Rizza V. (1995). Effects of metadoxine on cellular formation of fatty acid ethyl esters in ethanol treated rats. Int J Tissue React 17:101–108
  • Calabrese V, Rizza V. (1999). Effects of l-carnitine on the formation of fatty acid ethyl esters in brain and peripheral organs after short-term ethanol administration in rat. Neurochem Res 24:79–84
  • Calabrese V, Scapagnini G, Catalano C, et al. (2001). Effects of acetyl-l-carnitine on the formation of fatty acid ethyl esters in brain and peripheral organs after short-term ethanol administration in rat. Neurochem Res 26:167–174
  • Caprara DL, Brien JF, Iqbal U, et al. (2005). A guinea pig model for the identification of in utero alcohol exposure using fatty acid ethyl esters in neonatal hair. Pediatr Res 58:1158–1163
  • Carlson GP, Chancy AM, Jiang F. (1995). Comparison of the induction of rat glutathione s-transferase and fatty acid ethyl ester synthase activities. Toxicology 96:127–132
  • Chan D, Klein J, Koren G. (2004a). Validation of meconium fatty acid ethyl esters as biomarkers for prenatal alcohol exposure. J Pediatr 144:692
  • Chan D, Knie B, Boskovic R, Koren G. (2004b). Placental handling of fatty acid ethyl esters: Perfusion and subcellular studies. J Pharmacol Exp Ther 310:75–82
  • Chang W, Waltenbaugh C, Borensztajn J. (1997). Fatty acid ethyl ester synthesis by the isolated perfused rat heart. Metabolism 46:926–929
  • Chen Q, Barros H, Floren CH, Nilsson A. (1994). Absorption and incorporation into tissue-lipids of H-3 arachidonic-acid and C-14 linoleic-acid – effects of ethanol in jejunal tissue-cultures and in-vivo. Scand J Clin Lab Inv 54:495–504
  • Clugston RD, Jiang H, Lee MX, et al. (2011). Altered hepatic lipid metabolism in C57BL/6 mice fed alcohol: A targeted lipidomic and gene expression study. J Lipid Res 52:2021–2031
  • Dan L, Cluette-Brown JE, Kabakibi A, Laposata M. (1998). Quantitation of the mass of fatty acid ethyl esters synthesized by HepG2 cells incubated with ethanol. Alcohol Clin Exp Res 22:1125–1131
  • Dan L, Laposata M. (1997). Ethyl palmitate and ethyl oleate are the predominant fatty acid ethyl esters in the blood after ethanol ingestion and their synthesis is differentially influenced by the extracellular concentrations of their corresponding fatty acids. Alcohol Clin Exp Res 21:286–292
  • de Giovanni N, Donadio G, Chiarotti M. (2007). The reliability of fatty acid ethyl esters (FAEE) as biological markers for the diagnosis of alcohol abuse. J Anal Toxicol 31:93–97
  • de Giovanni N, Donadio G, Chiarotti M. (2008). Ethanol contamination leads to fatty acid ethyl esters in hair samples. J Anal Toxicol 32:156–159
  • Depergola G, Kjellstrom C, Holm C, et al. (1991). The metabolism of ethyl esters of fatty acids in adipose tissue of rats chronically exposed to ethanol. Alcohol Clin Exp Res 15:184–195
  • Diczfalusy MA, Bjorkhem I, Einarsson C, Alexson SEH. (1999). Formation of fatty acid ethyl esters in rat liver microsomes -- Evidence for a key role for acyl-CoA: Ethanol O-acyltransferase. Eur J Biochem 259:404–411
  • Diczfalusy MA, Bjorkhem I, Einarsson C, et al. (2001a). Characterization of enzymes involved in formation of ethyl esters of long-chain fatty acids in humans. J Lipid Res 42:1025–1032
  • Diczfalusy MA, von Wachenfeldt M, Holmberg I, Alexson SEH. (2001b). Possible role of long chain fatty acid ethyl esters in organ injury and as short-term markers of ethanol intake in humans. In: Wurst FM, ed. New and Upcoming Markers of Alcohol Consumption. Darmstadt, Berlin: Steinkopff, 17–34
  • Doyle KM, Bird DA, Al-Salihi S, et al. (1994). Fatty acid ethyl esters are present in human serum after ethanol ingestion. J Lipid Res 35:428–437
  • Doyle KM, Cluette-Brown JE, Dube DM, et al. (1996). Fatty acid ethyl esters in the blood as markers for ethanol intake. J Am Med Assoc 276:1152–1156
  • Estival A, Clemente F, Ribet A. (1981). Ethanol metabolism by the rat pancreas. Toxicol Appl Pharm 61:155–165
  • Gareri J, Appenzeller B, Walasek P, Koren G. (2011). Impact of hair-care products on FAEE hair concentrations in substance abuse monitoring. Anal Bioanal Chem 400:183–188
  • Gonzalez-Illan F, Ojeda-Torres G, Diaz-Vazquez LM, Rosario O. (2011). Detection of fatty acid ethyl esters in skin surface lipids as biomarkers of ethanol consumption in alcoholics, social drinkers, light drinkers, and teetotalers using a methodology based on microwave-assisted extraction followed by solid-phase microextraction and gas chromatography-mass spectrometry. J Anal Toxicol 35:232–237
  • Goodman DS, Deykin D. (1963). Fatty acid ethyl ester formation during ethanol metabolism in vivo. Proc Soc Exp Biol Med 113:65–67
  • Gorski NP, Nouraldin H, Dube DM, et al. (1996). Reduced fatty acid ethyl ester synthase activity in the white blood cells of alcoholics. Alcohol Clin Exp Res 20:268–274
  • Grigor MR, Bell ICJ. (1973). Synthesis of fatty acid esters of short-chain alcohols by an acyltransferase in rat liver microsomes. Biochim Biophys Acta 306:26–30
  • Gukovskaya AS, Mouria M, Gukovsky I, et al. (2002). Ethanol metabolism and transcription factor activation in pancreatic acinar cells in rats. Gastroenterology 122:106–118
  • Haber PS, Apte MV, Moran C, et al. (2004). Non-oxidative metabolism of ethanol by rat pancreatic acini. Pancreatology 4:82–89
  • Hamamoto T, Yamada S, Hirayama C. (1990). Nonoxidative metabolism of ethanol in the pancreas implication in alcoholic pancreatic damage. Biochem Pharmacol 39:241–246
  • Hartwig S, Auwaerter V, Pragst F. (2003a). Effect of hair care and hair cosmetics on the concentrations of fatty acid ethyl esters in hair as markers of chronically elevated alcohol consumption. For Sci Int 131:90–97
  • Hartwig S, Auwaerter V, Pragst F. (2003b). Fatty acid ethyl esters in scalp, pubic, axillary, beard and body hair as markers for alcohol misuse. Alcohol Alcohol 38:163–167
  • Hasaba A, Laposata M. (2001). The synthesis and secretion of fatty acid ethyl esters from HepG2 cells are stimulated by lipoproteins and albumin. Alcohol Clin Exp Res 25:338–343
  • Heith AM, Morse CR, Tsujita T, et al. (1995). Fatty acid ethyl ester synthase catalyzes the esterification of ethanol to cocaine. Biochem Biophys Res Commun 208:549–554
  • Hungund BL, Gokhale VS. (1994). Reduction of fatty acid ethyl ester accumulation by ganglioside GM1 in rat fetus exposed to ethanol. Biochem Pharmacol 48:2103–2108
  • Hungund BL, Goldstein DB, Villegas F, Cooper TB. (1988). Formation of fatty acid ethyl esters during chronic ethanol treatment in mice. Biochem Pharmacol 37:3001–3004
  • Isenberg KE, Bora PS, Zhou X, et al. (1992). Nonoxidative ethanol metabolism expression of fatty acid ethyl ester synthase-III in cultured neural cells. Biochem Bioph Res Co 185:938–943
  • Jackson RL. (1983). Chapter 5: Lipoprotein Lipase and Hepatic Lipase. In: Boyer PD, ed. Lipid enzymology. New York: Academic Press Inc., 169
  • Kabakibi A, Morse CR, Laposata M. (1998). Fatty acid ethyl esters and HepG2 cells: Intracellular synthesis and release from the cells. J Lipid Res 39:1568–1582
  • Kaphalia BS, Ansari GA. (2001). Purification and characterization of rat hepatic microsomal low molecular weight fatty acid ethyl ester synthase and its relationship to carboxylesterases. J Biochem Mol Toxicol 15:165–171
  • Kaphalia BS, Ansari GAS. (2003). Purification and characterization of rat pancreatic fatty acid ethyl ester synthase and its structural and functional relationship to pancreatic cholesterol esterase. J Biochem Mol Toxicol 17:338–345
  • Kaphalia BS, Bhopale KK, Kondraganti S, et al. (2010). Pancreatic injury in hepatic alcohol dehydrogenase-deficient deer mice after subchronic exposure to ethanol. Toxicol Appl Pharm 246:154–162
  • Kaphalia BS, Fritz RR, Ansari GA. (1997). Purification and characterization of rat liver microsomal fatty acid ethyl and 2-chloroethyl ester synthase and their relationship with carboxylesterase (PI 6.1). Chem Res Toxicol 10:211–218
  • Kaphalia BS, Granayem BI, Ansari GAS. (1996). Nonoxidative metabolism of 2-butoxyethanol via fatty acid conjugation in Fischer 344 rats. J Toxicol Environ Health 49:463–480
  • Kaphalia BS, Green SM, Ansari GAS. (1999). Fatty acid ethyl and methyl ester synthases, and fatty acid anilide synthase in HepG2 and AR42J cells: Interrelationships and inhibition by tri-o-tolyl phosphate. Toxicol Appl Pharm 159:134–141
  • Kaphalia BS, Cai P, Khan MF, et al. (2004a). Fatty acid ethyl esters: Markers of alcohol abuse and alcoholism. Alcohol 34:151–158
  • Kaphalia BS, Mericle KA, Ansari GAS. (2004b). Mechanism of differential inhibition of hepatic and pancreatic fatty acid ethyl ester synthase by inhibitors of serine-esterases: In vitro and cell culture studies. Toxicol Appl Pharmacol 200:7–15
  • Kinnunen PM, Lange LG. (1984). Identification and quantitation of fatty acid ethyl esters in biological specimens. Anal Biochem 140:567–576
  • Kissel J, Fontaine R, Turck C, et al. (1989). Molecular cloning and expression of cDNA for rat pancreatic cholesterol esterase. Biochim Biophys Acta 1006:227–236
  • Klein J, Karaskov T, Koren G. (1999). Fatty acid ethyl esters: A novel biologic marker for heavy in utero ethanol exposure: A case report. Ther Drug Monit 21:644–646
  • Kroetz D, Mcbride O, Gonzalez F. (1993). Glycosylation-dependent activity of baculovirus-expressed human liver carboxylesterases: cDNA cloning and characterization of two highly similar enzyme forms. Biochemistry 32:11606–11617
  • Kulaga V, Caprara D, Iqbal U, et al. (2006). Fatty acid ethyl esters (FAEE); comparative accumulation in human and guinea pig hair as a biomarker for prenatal alcohol exposure. Alcohol Alcohol 41:534–539
  • Kulaga V, Velazquez-Armenta Y, Aleksa K, et al. (2009). The effect of hair pigment on the incorporation of fatty acid ethyl esters (FAEE). Alcohol Alcohol 44:287–292
  • Lange LG. (1982). Nonoxidative ethanol metabolism formation of fatty-acid ethyl esters by cholesterol esterase EC-3.1.1.13. Proc Natl Acad Sci USA 79:3954–3957
  • Lange LG, Bergmann SR, Sobel BE. (1981). Identification of fatty acid ethyl esters as products of rabbit myocardial ethanol metabolism. J Biol Chem 256:12968–12973
  • Lange LG, Sobel BE. (1983a). Mitochondrial dysfunction induced by fatty-acid ethyl esters myocardial metabolites of ethanol. J Clin Invest 72:724–731
  • Lange LG, Sobel BE. (1983b). Myocardial metabolites of ethanol. Circ Res 52:479–482
  • Laposata EA, Harrison EH, Hedberg EB. (1990). Synthesis and degradation of fatty acid ethyl esters by cultured hepatoma cells exposed to ethanol. J Biol Chem 265:9688–9693
  • Laposata EA, Lange LG. (1986). Presence of nonoxidative ethanol metabolism in human organs commonly damaged by ethanol abuse. Science 231:497–499
  • Laposata EA, Scherrer DE, Lange LG. (1989). Fatty acid ethyl esters in adipoose tissue. A laboratory marker for alcohol-related death. Arch Pathol Lab Med 113:762–766
  • Laposata EA, Scherrer DE, Mazow C, Lange LG. (1987). Metabolism of ethanol by human brain to fatty acid ethyl esters. J Biol Chem 262:4653–4657
  • Laposata M, Szczepiorkowski ZM, Brown JE. (1995). Fatty acid ethyl esters: Non-oxidative metabolites of ethanol. Prostag Leukotr Ess 52:87–91
  • Littner Y, Cudd TA, O'Riordan MA, et al. (2008). Elevated fatty acid ethyl esters in meconium of sheep fetuses exposed in utero to ethanol -- A new animal model. Pediatr Res 63:164–168
  • Loftus N, Barnes A, Ashton S, et al. (2011). Metabonomic investigation of liver profiles of nonpolar metabolites obtained from alcohol-dosed rats and mice using high mass accuracy MSn analysis. J Proteome Res 10:705–713
  • Manautou JE, Buss NJ, Carlson GP. (1992). Oxidative and nonoxidative metabolism of ethanol by the rabbit lung. Toxicol Lett 62:93–99
  • Manautou JE, Carlson GP. (1991). Ethanol-induced fatty acid ethyl ester formation in vivo and in vitro in rat lung. Toxicology 70:303–312
  • Mericle KA, Kaphalia BS, Ansari GAS. (2002). Differential inhibition of hepatic, pancreatic, and plasma fatty acid ethyl ester synthase by tri-o-tolylphosphate in rats. Toxicol Appl Pharmacol 179:119–125
  • Mericle KA, Kaphalia BS, Ansari GA. (2004). Modulation of fatty acid methyl esters in rats pretreated with tri-o-tolyl phosphate. J Toxicol Environ Health A 67:583–593
  • Mogelson S, Lange LG. (1984). Nonoxidative ethanol metabolism in rabbit myocardium purification to homogeneity of fatty acyl ethyl ester synthase. Biochemistry 23:4075–4081
  • Mogelson S, Pieper SJ, Kinnunen PM, Lange LG. (1984). Partial purification and product characterization of fatty acid ethyl ester synthases in rabbit myocardium. Biochim Biophys Acta 798:144–148
  • Morfin JP, Kulig C, Everson G, Beresford T. (2007). Controlling for serum albumin level improves the correlation between serum fatty acid ethyl esters and blood ethanol level. Alcohol Clin Exp Res 31:265–268
  • Newsome WH, Rattray JBM. (1965). The enzymatic esterification of ethanol with fatty acids. Can J Biochem 43:1223–1233
  • Newsome WH, Rattray JB. (1966). Fatty acid ethyl ester formation by plasma in vitro. Can J Biochem 44:219–227
  • Ostrea JEM, Hernandez JD, Bielawski DM, et al. (2006). Fatty acid ethyl esters in meconium: Are they biomarkers of fetal alcohol exposure and effect? Alcohol Clin Exp Res 30:1152–1159
  • Patton S, McCarthy RD. (1966). Conversion of alcohol to ethyl esters of fatty acids by lactating goat. Nature 209:616
  • Pawan G. (1972). Metabolism of alcohol (ethanol) in man. Proc Nutr Soc 31:83–89
  • Pfutzer RH, Tadic SD, Li HS, et al. (2002). Pancreatic cholesterol esterase, ES-10, and fatty acid ethyl ester synthase III gene expression are increased in the pancreas and liver but not in the brain or heart with long-term ethanol feeding in rats. Pancreas 25:101–106
  • Polokoff MA, Bell RM. (1978). Limited palmitoyl-CoA penetration into microsomal vesicles as evidenced by a highly latent ethanol acyltransferase activity. J Biol Chem 253:7173–7178
  • Pragst F, Auwaerter V, Sporkert F, Spiegel K. (2001). Analysis of fatty acid ethyl esters in hair as possible markers of chronically elevated alcohol consumption by headspace solid-phase microextraction (HS-SPME) and gas chromatography-mass spectrometry (GC-MS). Forensic Sci Int 121:76–88
  • Pragst F, Auwarter V, Kiessling B, Dyes C. (2004). Wipe-test and patch-test for alcohol misuse based on the concentration ratio of fatty acid ethyl esters and squalene CFAEE/CSQ in skin surface lipids. For Sci Int 143:77–86
  • Pragst F, Spiegel K, Sporkert F, Bohnenkamp M. (2000). Are there possibilities for the detection of chronically elevated alcohol consumption by hair analysis? A report about the state of investigation. For Sci Int 107:201–223
  • Refaai MA, Nguyen PN, Cluette-Brown JE, Laposata M. (2003). Ethyl arachidonate is the predominant fatty acid ethyl ester in the brains of alcohol-intoxicated subjects at autopsy. Lipids 38:269–273
  • Refaai MA, Nguyen PN, Steffensen TS, et al. (2002). Liver and adipose tissue fatty acid ethyl esters obtained at autopsy are postmortem markers for premortem ethanol intake. Clin Chem 48:77–83
  • Riley DJS, Kyger EM, Spilburg CA, Lange LG. (1990). Pancreatic cholesterol esterases 2. Purification and characterization of human pancreatic fatty acid ethyl ester synthase. Biochemistry 29:3848–3852
  • Saghir M, Blodget E, Laposata M. (1999a). The hydrolysis of fatty acid ethyl esters in low-density lipoproteins by red blood cells, white blood cells and platelets. Alcohol 19:163–168
  • Saghir M, Werner J, Laposata M. (1997). Rapid in vivo hydrolysis of fatty acid ethyl esters, toxic nonoxidative ethanol metabolites. Am J Physiol 273:G184–G190
  • Saghir M, Werner J, Laposata M. (1999b). A comparison of the hydrolysis and metabolism in rats of fatty acid ethyl esters within human low density lipoproteins and rat low density lipoproteins. Res Commun Alcohol S 20:123–133
  • Salem RO, Refaai MA, Cluette-Brown JE, et al. (2001). Fatty acid ethyl esters in liver and adipose tissues as postmortem markers for ethanol intake. Clin Chem 47:722–725
  • Salem RO, Cluette-Brown JE, Laposata M. (2005). Fatty acid ethyl esters, nonoxidative ethanol metabolites, synthesis, uptake, and hydrolysis by human platelets. Biochim Biophys Acta 1738:99–104
  • Salem RO, Laposata M, Rajendram R, et al. (2006). The total body mass of fatty acid ethyl esters in skeletal muscles following ethanol exposure greatly exceeds that found in the liver and the heart. Alcohol Alcohol 41:598–603
  • Sharma R, Gupta S, Singhal SS, et al. (1991). Independent segregation of glutathione s-transferase and fatty acid ethyl ester synthase from pancreas and other human tissues. Biochem J 275:507–513
  • Singhal SS, Gupta S, Saxena M, et al. (1991). Purification and characterization of glutathione s transferases from rat pancreas. Biochim Biophys Acta 1079:285–292
  • Small C, Yeaman S, West D, Clegg R. (1991). Cholesterol ester hydrolysis and hormone-sensitive lipase in lactating rat mammary tissue. Biochim Biophys Acta 1082:251–254
  • Soderberg BL, Sicinska ET, Blodget E, et al. (1999). Preanalytical variables affecting the quantification of fatty acid ethyl esters in plasma and serum samples. Clin Chem 45:2183–2190
  • Susse S, Selavka CM, Mieczkowski T, Pragst F. (2010). Fatty acid ethyl ester concentrations in hair and self-reported alcohol consumption in 644 cases from different origin. Forensic Sci Int 196:111–117
  • Suzuki T, Kovacs MS, Board PG. (1990). Do the major human glutathione s-transferases have fatty acid ethyl ester synthase activity? FEBS Lett 275:58–60
  • Swift R. (2003). Direct measurement of alcohol and its metabolites. Addiction 98 Suppl 2:73–80
  • Szczepiorkowski ZM, Dickersin GR, Laposata M. (1995). Fatty acid ethyl esters decrease human hepatoblastoma cell proliferation and protein synthesis. Gastroenterology 108:515–522
  • Treloar T, Madden LJ, Winter JS, et al. (1996). Fatty acid ethyl ester synthesis by human liver microsomes. Biochim Biophys Acta 1299:160–166
  • Tsujita T, Okuda H. (1992). Fatty acid ethyl ester synthase in rat adipose tissue and its relationship to carboxylesterase. J Biol Chem 267:23489–23494
  • Tsujita T, Okuda H. (1994a). Fatty acid ethyl ester-synthesizing activity of lipoprotein lipase from rat postheparin plasma. J Biol Chem 269:5884–5889
  • Tsujita T, Okuda H. (1994b). The synthesis of fatty acid ethyl ester by carboxylester lipase. Eur J Biochem 224:57–62
  • Tsujita T, Sumiyoshi M, Okuda H. (1999). Fatty acid alcohol ester-synthesizing activity of lipoprotein lipase. J Biochem 126:1074–1079
  • Vallaro GM, Behonick GS, Hodnett CN, et al. (1997). Acute temporal distribution of fatty acid ethyl esters in pregnant long-evans rats. Toxicol Method 7:97–110
  • Vogel WC, Ryan WG, Koppel JL, Olwin JH. (1965). Post-heparin phospholipase and fatty acid transesterification in human plasma. J Lipid Res 6:335–340
  • Werner J, Saghir M, Castillo CFD, et al. (2001). Linkage of oxidative and nonoxidative ethanol metabolism in the pancreas and toxicity of nonoxidative ethanol metabolites for pancreatic acinar cells. Surgery 129:736–744
  • Werner J, Saghir M, Warshaw AL, et al. (2002). Alcoholic pancreatitis in rats: Injury from nonoxidative metabolites of ethanol. Am J Physiol Gastrointest Liver Physiol 283:G65–G73
  • Wright M, Bieser KJ, Kinnunen PM, Lange LG. (1987). Nonoxidative ethanol metabolism in human leukocytes detection of fatty acid ethyl ester synthase activity. Biochem Bioph Res Co 142:979–985
  • Wu H, Bhopale KK, Ansari GAS, Kaphalia BS. (2008). Ethanol-induced cytotoxicity in rat pancreatic acinar Ar42J cells: Role of fatty acid ethyl esters. Alcohol Alcohol 43:1–8
  • Wu H, Cai P, Clemens DL, et al. (2006). Metabolic basis of ethanol-induced cytotoxicity in recombinant HepG2 cells: Role of nonoxidative metabolism. Toxicol Appl Pharmacol 216:238–247
  • Wurst FM, Alexson S, Wolfersdorf M, et al. (2004). Concentration of fatty acid ethyl esters in hair of alcoholics: Comparison to other biological state markers and self reported-ethanol intake. Alcohol Alcohol 39:33–38
  • Yamazaki K, Gilg T, Kauert G, et al. (1997). Nonoxidative ethanol and methanol changes in the heart and brain tissue of alcohol abusers. Nihon Hoigaku Zasshi 51:380–387
  • Yoerger DM, Best CA, Mcquillan BM, et al. (2006). Rapid fatty acid ethyl ester synthesis by porcine myocardium upon ethanol infusion into the left anterior descending coronary artery. Am J Pathol 168:1435–1442
  • Zelner I, Hutson JR, Kapur BM, et al. (2012). False-positive meconium test results for fatty acid ethyl esters secondary to delayed sample collection. Alcohol Clin Exp Res 36:1497–1506
  • Zimatkin SM, Deitrich RA. (1997). Ethanol metabolism in the brain. Addict Biol 2:387–399

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.