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J. Biol. Chem., Vol. 279, Issue 50, 52160-52167, December 10, 2004

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Leaky -Oxidation of a trans-Fatty Acid

INCOMPLETE -OXIDATION OF ELAIDIC ACID IS DUE TO THE ACCUMULATION OF 5-TRANS-TETRADECENOYL-CoA AND ITS HYDROLYSIS AND CONVERSION TO 5-TRANS-TETRADECENOYLCARNITINE IN THE MATRIX OF RAT MITOCHONDRIA^*

Wenfeng Yu, Xiquan Liang, Regina E. Ensenauer, Jerry Vockley, Lawrence Sweetman¶, and Horst Schulz||

From the Department of Chemistry, City College and Graduate Center of the City University of New York, New York, New York 10031, the Department of Medical Genetics, Mayo Clinic, Rochester, Minnesota 55905, and the ^¶Institute of Metabolic Disease, Baylor University Medical Center, Dallas, Texas 75226

The degradation of elaidic acid (9-trans-octadecenoic acid), oleic acid, and stearic acid by rat mitochondria was studied to determine whether the presence of a trans double bond in place of a cis double bond or no double bond affects -oxidation. Rat mitochondria from liver or heart effectively degraded the coenzyme A derivatives of all three fatty acids. However, with elaidoyl-CoA as a substrate, a major metabolite accumulated in the mitochondrial matrix. This metabolite was isolated and identified as 5-trans-tetradecenoyl-CoA. In contrast, little or none of the corresponding metabolites were detected with oleoyl-CoA or stearoyl-CoA as substrates. A kinetic study of long-chain acyl-CoA dehydrogenase (LCAD) and very long-chain acyl-CoA dehydrogenase revealed that 5-trans-tetradecenoyl-CoA is a poorer substrate of LCAD than is 5-cis-tetradecenoyl-CoA, while both unsaturated acyl-CoAs are poor substrates of very long-chain acyl-CoA dehydrogenase when compared with myristoyl-CoA. Tetradecenoic acid and tetradecenoylcarnitine were detected by gas chromatography/mass spectrometry and tandem mass spectrometry, respectively, when rat liver mitochondria were incubated with elaidoyl-CoA but not when oleoyl-CoA was the substrate. These observations support the conclusion that 5-trans-tetradecenoyl-CoA accumulates in the mitochondrial matrix, because it is less efficiently dehydrogenated by LCAD than is its cis isomer and that the accumulation of this -oxidation intermediate facilitates its hydrolysis and conversion to 5-trans-tetradecenoylcarnitine thereby permitting a partially degraded fatty acid to escape from mitochondria. Analysis of this compromised but functional process provides insight into the operation of -oxidation in intact mitochondria.

Received for publication, August 23, 2004 , and in revised form, October 1, 2004.

^* This work was supported by U.S. Public Health Services Grant HL30847 from the NHLBI, National Institutes of Health, and by Grant RR03060 to Research Centers of Minority Institutions. The costs of publication of this article were defrayed in part by the payment of page charges. This article must therefore be hereby marked "advertisement" in accordance with 18 U.S.C. Section 1734 solely to indicate this fact.

^|| To whom correspondence should be addressed: Dept. of Chemistry, City College of the City University of New York, Convent Ave. at 138th St., New York, NY 10031. Tel.: 212-650-8323; Fax: 212-650-8322; E-mail: hoschu{at}sci.ccny.cuny.edu.

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