Metabolism of furan fatty acids in fish.

In vivo experiments on interconversions of furan fatty acids in fish are described. Administration of 2- or 3-14C-labelled furan fatty acids showed that the heterocycle does not interfere with conversions at the carboxyl group, such as shortening and elongating the chain, or its reduction to alcohol. There was no indication for desaturation of proximal chains, methylation or demethylation of the ring, or changes in the terminal chains. According to these restricted metabolic correlations, the furan fatty acids can be classified in specific structural families of bis-homologs. Distinct parent furan compounds are likely for each of these families. [1-14C]Acetate was incorporated by fish into furan fatty acids. Their chemical oxidation showed that only the resulting dicarboxylic fragments were labelled. They represent the proximal chain including alpha-C of the ring. Label was not found in the monocarboxylic acids which represent terminal chains with alpha'-C, and ring-methyl substituents with beta- and beta'-C. Accordingly, fish do not synthesize from acetate the terminal alkyl chain including the carbons in the cyclic portion of the furan fatty acids.