Improved specificity of cardiolipin peroxidation by soybean lipoxygenase: a liquid chromatography - electrospray ionization mass spectrometry investigation

Peroxidation catalysed by Soybean Lypoxigenase was performed on tetralinoleyl‐cardiolipin with the aim of generating selectively oxidized products, to be used subsequently as standards for studies on cardiolipin oxidation. The reaction products were characterized by LC‐ESI‐MS and MS/MS, and the proc...

Full description

Saved in:
Bibliographic Details
Published in:Journal of mass spectrometry. 2011-12, Vol.46 (12), p.1255-1262
Main Authors: Losito, I., Conte, E., Introna, B., Megli, F. M., Palmisano, F.
Format: Article
Language:English
Subjects:
Analytical, structural and metabolic biochemistry
Animals
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
cardiolipins
Cardiolipins - analysis
Cardiolipins - chemistry
Cardiolipins - metabolism
Cattle
Chromatography, High Pressure Liquid - methods
electrospray ionization mass spectrometry
enzymatic peroxidation
Fundamental and applied biological sciences. Psychology
Glycerolipids, phospholipids
Glycine max - enzymology
Lipid Peroxidation
Lipids
Lipoxygenase - chemistry
Lipoxygenase - metabolism
Methods. Procedures. Technologies
Other biological molecules
oxidized phospholipids
soybean lipoxygenase
Spectrometry, Mass, Electrospray Ionization - methods
Substrate Specificity
Tandem Mass Spectrometry - methods
Citations: Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Peroxidation catalysed by Soybean Lypoxigenase was performed on tetralinoleyl‐cardiolipin with the aim of generating selectively oxidized products, to be used subsequently as standards for studies on cardiolipin oxidation. The reaction products were characterized by LC‐ESI‐MS and MS/MS, and the process was found to link a hydroperoxylic group on one or more linoleic chains of cardiolipin, up to a total of four groups per molecule. Interestingly, the incidence of other oxidized products, like those arising from multiple hydroxylation or mixed hydroxylation‐hydroperoxydation, previously observed after the chemical oxidation of the same cardiolipin, was found to be negligible. Moreover, evidences for the presence of the hydroperoxylic group(s) almost exclusively on carbon 13 of the linoleic chain(s) were obtained by MS/MS measurements. The enzymatic approach, integrated with a preparative separation step, which could be developed by adapting the chromatographic conditions adopted in the present work for analytical purposes, represents a promising strategy for the synthesis of highly specific mono‐ or multi‐peroxidated derivatives of cardiolipins. Copyright © 2011 John Wiley & Sons, Ltd.
ISSN:1076-5174
1096-9888
DOI:10.1002/jms.2012