Effects of soybean lipoxygenase-1 on phosphatidylcholines containing furan fatty acids.
Naturally occurring tetraalkylsubstituted furan fatty acids (F-acids) were tested as potential substrates for soybean lipoxygenase-1. For this purpose, F-acid methyl ester and phosphatidylcholines containing F-acids at the sn-2 position of the glycerol residue were incubated with the enzyme. Oxidation of F-acids only occurs in the presence of linoleic acid as co-substrate. Linoleic acid is converted by lipoxygenase to the corresponding hydroperoxide that oxidizes the F-acid, probably in a radical reaction, to form an unstable dioxoene compound. This intermediate then forms, dependent on pH, unsaturated furanoid acids or isomers with cyclopentenolone structure that can be detected by gas chromatography/mass spectrometry (GC/MS). F-acids located at the sn-2 position of a synthetic phosphatidylcholine (PC), containing linoleic acid in the sn-1 position, are co-oxidized to a greater extent by incubation with soybean lipoxygenase-1 than are F-acids bound to PC with myristic acid in the sn-1 position when subjected to the enzyme in the presence of a great excess of linoleic acid. The results suggest that F-acids may play a strategic role in antioxidative processes in plant cells.
Batna
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A
Lehrstuhl für Organische Chemie I, Universität Bayreuth, Germany.
Spiteller
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G
D005227:Fatty Acids / Q000378:metabolism*; D005663:Furans / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D005990:Glycerol / Q000378:metabolism; D019787:Linoleic Acid; D008041:Linoleic Acids / Q000378:metabolism; D008084:Lipoxygenase / Q000378:metabolism*; D013058:Mass Spectrometry; D019814:Myristic Acid; D009227:Myristic Acids / Q000378:metabolism; D010084:Oxidation-Reduction; D010713:Phosphatidylcholines / Q000378:metabolism*; D013025:Glycine max / Q000201:enzymology*
D005227:Fatty Acids; D005663:Furans; D008041:Linoleic Acids; D009227:Myristic Acids; D010713:Phosphatidylcholines; D019814:Myristic Acid; D019787:Linoleic Acid; D008084:Lipoxygenase; D005990:Glycerol