Furan fatty acids: occurrence, synthesis, and reactions. Are furan fatty acids responsible for the cardioprotective effects of a fish diet?
Furan FA (F-acids) are tri- or tetrasubstituted furan derivatives characterized by either a propyl or pentyl side chain in one of the alpha-positions; the other is substituted by a straight long-chain saturated acid with a carboxylic group at its end. F-acids are generated in large amounts in algae, but they are also produced by plants and microorganisms. Fish and other marine organisms as well as mammals consume F-acids in their food and incorporate them into phospholipids and cholesterol esters. F-acids are catabolized to dibasic urofuran acids, which are excreted in the urine. The biogenetic precursor of the most abundant F-acid, F6, is linoleic acid. Methyl groups in the beta-position are derived from adenosylmethionine. Owing to the different alkyl substituents, synthesis of F-acids requires multistep reactions. F-acids react readily with peroxyl radicals to generate dioxoenes. The radical-scavenging ability of F-acids may contribute to the protective properties of fish and fish oil diets against mortality from heart disease.
Spiteller
Gerhard
G
Lehrstuhl für Organische Chemie I, University of Bayreuth, Bayreuth, Germany. gerhard.spiteller@uni-bayreuth.de
D002316:Cardiotonic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D004032:Diet; D006801:Humans; D008041:Linoleic Acids / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D015394:Molecular Structure; D017747:Seafood
D002316:Cardiotonic Agents; D008041:Linoleic Acids