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Desaturation and chain elongation of [1-14C]mono-trans isomers of linoleic and alpha-linolenic acids in perfused rat liver. 1998

L Bretillon, and J M Chardigny, and J P Noël, and J L Sébédio
INRA, Unité de Nutrition Lipidique, 21034 Dijon Cédex, France.

Trans polyunsaturated fatty acids are produced during heat treatment of oils, such as deodorization and frying. The detailed metabolic pathways of these trans isomers are not fully understood. In the present work, the desaturation and chain elongation of [1-14C]linoleic acid, 9cis,12trans -18:2, 9trans,12cis -18:2, alpha-linolenic acid, 9cis, 12cis,15trans -18:3 and 9trans,12cis, 15cis -18:3 were studied using a perfused rat liver model. After perfusion with both trans isomers of 18:2n-6, the 14C was equally distributed between phospholipids and triacylglycerols, compared to the 70:30 distribution (phospholipids:triacylglycerols) observed after infusing linoleic acid. The corresponding distribution of 14C after perfusion with both trans isomers of 18:3n-3 was comparable to what was obtained for alpha-linolenic acid. The products of conversion were analyzed by combination of different radio chromatographic methods. 9cis,12trans -18:2 was 16 times more converted into a C18:3n-6 fatty acid than linoleic acid into gamma-linolenic acid. Trans -18:2 isomers were more elongated into "dead-end products" when compared to the conversion of linoleic acid into 20:2n-6 (from 2- to 5-times more). 9cis,12cis,15trans -18:3 and 9trans,12cis, 15cis-18:3 were 2- and 10-times less converted to trans -20:5, respectively, than alpha-linolenic acid into eicosapentaenoic acid. Moreover, 9cis,12cis,15trans -18:3 and 9trans, 12cis, 15cis -18:3 were equally and 2.5-times more elongated into "dead-end products", respectively, than alpha-linolenic acid into 20:3n-3. The partitioning of the conversion between formation of desaturated and chain elongated products on the one hand and production of "dead-end products" on the other was also calculated. Compared to their cis analogs, 9trans,12cis -18:2 and 9trans,12cis, 15cis -18:3 were elongated into trans "dead-end products" rather than being converted to desaturated and chain elongated trans-metabolites. On the other hand 9cis,12cis,15trans -18:3 was more desaturated and chain elongated into 17trans 20:5 rather than elongated into 17trans -20:3.

UI MeSH Term Description Entries
D007536 Isomerism The phenomenon whereby certain chemical compounds have structures that are different although the compounds possess the same elemental composition. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Isomerisms
D008099 Liver A large lobed glandular organ in the abdomen of vertebrates that is responsible for detoxification, metabolism, synthesis and storage of various substances. Livers
D008297 Male Males
D010084 Oxidation-Reduction A chemical reaction in which an electron is transferred from one molecule to another. The electron-donating molecule is the reducing agent or reductant; the electron-accepting molecule is the oxidizing agent or oxidant. Reducing and oxidizing agents function as conjugate reductant-oxidant pairs or redox pairs (Lehninger, Principles of Biochemistry, 1982, p471). Redox,Oxidation Reduction
D010477 Perfusion Treatment process involving the injection of fluid into an organ or tissue. Perfusions
D010743 Phospholipids Lipids containing one or more phosphate groups, particularly those derived from either glycerol (phosphoglycerides see GLYCEROPHOSPHOLIPIDS) or sphingosine (SPHINGOLIPIDS). They are polar lipids that are of great importance for the structure and function of cell membranes and are the most abundant of membrane lipids, although not stored in large amounts in the system. Phosphatides,Phospholipid
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D017208 Rats, Wistar A strain of albino rat developed at the Wistar Institute that has spread widely at other institutions. This has markedly diluted the original strain. Wistar Rat,Rat, Wistar,Wistar Rats
D050356 Lipid Metabolism Physiological processes in biosynthesis (anabolism) and degradation (catabolism) of LIPIDS. Metabolism, Lipid
D051381 Rats The common name for the genus Rattus. Rattus,Rats, Laboratory,Rats, Norway,Rattus norvegicus,Laboratory Rat,Laboratory Rats,Norway Rat,Norway Rats,Rat,Rat, Laboratory,Rat, Norway,norvegicus, Rattus

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