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Effects of soybean lipoxygenase‐1 on phosphatidylcholines containing furan fatty acids
Author(s) -
Batna Andreas,
Spiteller Gerhard
Publication year - 1994
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02537308
Subject(s) - chemistry , linoleic acid , lipoxygenase , furan , polyunsaturated fatty acid , myristic acid , glycerol , organic chemistry , enzyme , residue (chemistry) , fatty acid , chromatography , stereochemistry , palmitic acid
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 wer 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 the 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 phosphadidylcholine (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.