Investigations of the origin of the furan fatty acids (F‐acids)

Abstract

The possible role of linoleic acid as a biogenetic precursor of the furan fatty acids (F-acids) was investigated in in vivo experiments in the rat, using a C19 analogue of linoleic acid and gas chromatography-mass spectrometry. No evidence of incorporation of this compound into the F-acids was found. Using an improved analysis procedure by converting F-acids into their tetrahydrofuran derivatives (enabling a separation from the large amounts of normal fatty acids), F-acids (F3, F4 and F6) were detected in rat food, correcting earlier results. Quantification of F-acid intake with food and excretion of furandicarboxylic acids in the urine, suggested the possibility that the F-acids are not produced de novo in the rat, but instead accumulate in tissue after nutritional intake.

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

“…In order to prove the hypothesis that F-acids are derived from linoleic acid, a homolog of linoleic acid was fed to rats, but no homologous F-acids could be detected in their livers. As a consequence it was assumed that F-acids may be derived from rat food (96). This assumption was confirmed later by an investigation of plants (49).…”

Furanoid fatty acids in oils from soybeans lacking lipoxygenase isoenzymes

“…They differ from one another in reaction products, pH optima and substrate specificities (5,6). On the basis that formation of the furan ring system can be explained by a lipoxygenasecatalyzed reaction (7)(8)(9), it has been speculated that this enzyme is involved in the biosynthesis of furanoid fatty acids. As soybean varieties lacking one or two isoenzymes have been developed (10)(11)(12), it was of interest to investigate whether the lack of a particular lipoxygenase isoenzyme affects the concentrations of F20 and F22 in SBO.…”

Liquid chromatographic tandem mass spectrometric assay for the uremic toxin 3‐carboxy‐4‐methyl‐5‐propyl‐2‐furanpropionic acid in human plasma

“…One report has suggested that CMPF might not be the result of de novo synthesis, but rather from dietary sources. 13 However, it is unclear what foods contain the CMPF and how the diet affects plasma CMPF concentration. Further studies are needed to address these issues.…”