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Furan fatty acids: Occurrence, synthesis, and reactions. Are furan fatty acids responsible for the cardioprotective effects of a fish diet?

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Lipids

Abstract

Furan FA (F-acids) are tri-or tetrasubstituted furan derivatives characterized by either a propyl or pentyl side chain in one of the α-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 β-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.

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Abbreviations

AA:

arachidonic acid

CLE:

cholesterol ester

F-acid:

furan FA

LA:

linoleic acid

LOOH:

lipid hydroperoxide

LOX:

lipoxygenase

LPO:

lipid peroxidation

OA:

oleic acid

PL:

phospholipids

TX:

thromboxane

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    Gerhard Spiteller

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Spiteller, G. Furan fatty acids: Occurrence, synthesis, and reactions. Are furan fatty acids responsible for the cardioprotective effects of a fish diet?. Lipids 40, 755–771 (2005). https://doi.org/10.1007/s11745-005-1438-5

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