Synthesis of fatty acid esters of short-chain alcoh an acyltransferase in rat liver microsomes

Grigor, Murray R.; Bell, Iverson C.

doi:10.1016/0005-2760(73)90204-x

Cited by 36 publications

(13 citation statements)

References 17 publications

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“…Of interest, in another study, fatty acid ethyl esters were identified in Rhizopus arrhizus (34), but no enzymatic pathway for their formation was identified. In vitro production of fatty acid ethyl esters was noted initially in 1973 in liver microsomes (35) and subsequently confirmed (36). In view of the widespread use of methanol as a competing nucleophile for water in the study of numerous proteases (37) to form methyl esters, the quantitative importance of the finding that ethanol in vitro may give rise to ethyl esters is difficult to assess, especially when 40 MM palmitoyl-Coenzyme A, a supraphysiological concentration, was used in the assays.…”

Section: Methodsmentioning

confidence: 90%

Mitochondrial dysfunction induced by fatty acid ethyl esters, myocardial metabolites of ethanol.

Lange¹,

Sobel²

1983

J. Clin. Invest.

230

106

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A B S T R A C T Mechanisms responsible for alcohol-induced heart muscle disease have been difficult to elucidate partly because of previously obscure, demonstrable cardiac metabolism of ethanol. Recently, fatty acid ethyl esters were identified in our laboratory and found to be myocardial metabolites of ethanol. In the present study, they have been shown to induce mitochondrial dysfunction. Incubation of isolated myocardial mitochondria with fatty acid ethyl esters led to a concentration-dependent reduction of the respiratory control ratio index of coupling of oxidative phosphorylation and decrement of maximal rate of oxygen consumption. Furthermore, fatty acid ethyl esters were demonstrated to bind to mitochondria in vitro, and, importantly, 72% of intracellularly synthesized ethyl esters were found to bind to mitochondria isolated from intact tissue incubated with ethanol. Protein binding of fatty acid ethyl esters was markedly less than that of fatty acids. Because uncoupling of mitochondrial oxidative phosphorylation correlated with the cleavage of fatty acid ethyl ester shown to be initially bound to mitochondria, with resultant generation of fatty acid, a potent uncoupler, in a locus in or near the mitochondrial membrane, fatty acid ethyl esters may contribute to a potentially toxic shuttle for fatty acid with transport from physiological intracellular binding sites to the mitochondrial membrane; direct effects of fatty acid ethyl esters may also be deleterious. Operation of this shuttle as a result of ethanol ingestion and subsequent accumulation of fatty acid ethyl esters may account for the impaired mitochondrial function and inefficient energy production associated with toxic effects of ethanol on the heart.

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Section: Methodsmentioning

confidence: 90%

Mitochondrial dysfunction induced by fatty acid ethyl esters, myocardial metabolites of ethanol.

Lange¹,

Sobel²

1983

J. Clin. Invest.

230

106

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“…A question that follows from FAEE detection in plasma is where the FAEE in plasma originate. It is possible that they originate in the liver and are secreted into the plasma (Aleryani et al, 1996; Grigor and Bell, 1973) as HepG2 cells (a hepatoblastoma cell line) can secrete FAEE, especially when lipoproteins or albumin which can carry FAEE, are added to the extracellular medium (Hasaba and Laposata, 2001). Gorski et al (1996) demonstrated that blood cells are able to synthesize FAEE, with white blood cells (WBC), especially the mononuclear fraction, having the highest rate of synthesis on a per cell basis.…”

mentioning

confidence: 99%

Fatty Acid Ethyl Esters in Human Mononuclear Cells: Production by Endogenous Synthesis Greatly Exceeds the Uptake of Preformed Ethyl Esters

Alhomsi

Cluette‐Brown

Laposata

2006

Alcoholism Clin & Exp Res

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“…Rat brain and murine ascites cells also synthesize wax esters (5,6). Cofactors such as ATP, Mg 2+ , and CoA reportedly stimulate wax ester formation (7,8). However, the wax ester-synthesizing enzymes have not been purified and characterized.…”

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confidence: 99%

Wax ester‐synthesizing activity of lipases

Tsujita

Sumiyoshi

Okuda

1999

Lipids

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The synthesis/hydrolysis of wax esters was studied in an aqueous solution using purified rat pancreatic lipase, porcine pancreatic carboxylester lipase, and Pseudomonas fluorescens lipase. The equilibrium between wax ester synthesis and hydrolysis favored ester formation at neutral pH. The synthesizing activities were measured using free fatty acid or triacylglycerol as the acyl donor and an equimolar amount of long-chain alcohol as the acyl acceptor. When oleic acid and hexadecanol emulsified with gum arabic were incubated with these lipases, wax ester was synthesized, in a dose- and time-dependent manner, and the apparent equilibrium ratio of palmityl oleate/free oleic acid was about 0.9/0.1. These lipases catalyzed the hydrolysis of palmityl oleate emulsified with gum arabic, and the apparent equilibrium ratio of palmityl oleate/free oleic acid was also about 0.9/0.1. The apparent equilibrium ratio of wax ester/free fatty acid catalyzed by lipase depended on incubation pH and fatty alcohol chain length. When equimolar amounts of trioleoylglycerol and fatty acyl alcohol were incubated with pancreatic lipase, carboxylester lipase, or P. fluorescens lipase, wax esters were synthesized dose-dependently. These results suggest that lipases can catalyze the synthesis of wax esters from free fatty acids or through degradation of triacylglycerol in an aqueous medium.

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Synthesis of fatty acid esters of short-chain alcoh an acyltransferase in rat liver microsomes

Cited by 36 publications

References 17 publications

Mitochondrial dysfunction induced by fatty acid ethyl esters, myocardial metabolites of ethanol.

Mitochondrial dysfunction induced by fatty acid ethyl esters, myocardial metabolites of ethanol.

Fatty Acid Ethyl Esters in Human Mononuclear Cells: Production by Endogenous Synthesis Greatly Exceeds the Uptake of Preformed Ethyl Esters

Wax ester‐synthesizing activity of lipases

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