A simple method to generate oxidized phosphatidylcholines in amounts close to one milligram

• The commercial availability of oxidized (phospho)lipids is rather limited – despite their biological significance.
• It will be shown that selected oxidation products of PC 16:0/18:2 can be very easily prepared.
• Oxidations were induced by the Fenton reaction and the individual fractions isolated by preparative TLC.
• MALDI–TOF MS was used to identify the products present in the different fractions.

Oxidized (phospho)lipids are of paramount interest from different reasons: beside their significant in vivo relevance, these products are often needed in the laboratory to study the response of selected cells to oxidized lipids. Unfortunately, the commercial availability of oxidized lipids is limited and scientists interested in studying the physiological impact of oxidized lipids are normally forced to prepare the required compounds by themselves.We will show here that chain-shortened products of oxidized phosphatidylcholines (PCs) such as aldehydes and carboxylic acids can be easily (and in nearly quantitative yields) generated by the Fenton reaction (H2O2 + Fe2+) or the KMnO4-induced oxidation of the PC. Using the Fenton reaction and physiological saline, chlorinated oxidation products such as chlorohydrins are also readily available. Additionally, it will be shown that preparative thin-layer chromatography (TLC) is a convenient but simple method to isolate the individual oxidation products in reasonable yields and high purities: all relevant products could be successfully identified by matrix-assisted laser desorption and ionization (MALDI) mass spectrometry and the amounts of the oxidized products determined by a simple colorimetric assay.

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