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Lipids

, Volume 29, Issue 6, pp 397–403 | Cite as

Effects of soybean lipoxygenase-1 on phosphatidylcholines containing furan fatty acids

  • Andreas Batna
  • Gerhard Spiteller
Article

Abstract

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 thesn-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 thesn-2 position of a synthetic phosphadidylcholine (PC), containing linoleic acid in thesn-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 thesn-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.

Keywords

Linoleic Acid Furan Peroxyl Radical Furan Ring Nuclear Magnetic Reso 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Abbreviations

DMAP

4-dimethylaminopyridine

EDC

N-ethyl-N′--(3-dimethylaminopropyl)carbodiimide hydrochloride

F-acid(s)

furan fatty acid(s)

FID

flame-ionization detector

GC

gas chromatography

LSI-MS

liquid secondary ion mass spectrometry

LOX

soybean lipoxygenase-1

MS

mass spectrometry

MSTFA

N-methyl-N-trimethylsilyltrifluoroacetamide

NMR

nuclear magnetic resonance

PC

phosphatidylcholine(s)

14∶0-F-PC

1-tetradecanoyl-2-[11-(3,4-dimethyl-5-butyl-furan-2-yl)undecanoyl]-sn-glycero-3-phosphocholine

18∶2-F-PC

1-(cis-9,cis-12-octadecadienoyl)-2-[11-(3,4-dimethyl-5-butylfuran-2-yl)undecanoyl]-sn-glycero-3-phosphocholine

TLC

thin-layer chromatography

Tris-HCl

tris(hydroxymethyl)amino-methane hydrochloride

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Copyright information

© American Oil Chemists’ Society 1994

Authors and Affiliations

  • Andreas Batna
    • 1
  • Gerhard Spiteller
    • 1
  1. 1.Lehrstuhl für Organische Chemie IUniversität BayreuthBayreuthGermany

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