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Study of sphingolipids oxidation by ESI tandem MS
Author(s) -
Melo Tânia,
Maciel Elisabete,
Oliveira Maria Manuel,
Domingues Pedro,
Domingues Maria R. M.
Publication year - 2012
Publication title -
european journal of lipid science and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.614
H-Index - 94
eISSN - 1438-9312
pISSN - 1438-7697
DOI - 10.1002/ejlt.201100328
Subject(s) - sphingolipid , ceramide , chemistry , sphingomyelin , oxidative stress , sphingosine , oxidative phosphorylation , hydroxyl radical , lipid oxidation , dna oxidation , tandem , tandem mass spectrometry , biochemistry , stereochemistry , membrane , antioxidant , apoptosis , chromatography , mass spectrometry , receptor , oxidative damage , materials science , composite material
Sphingolipids are a class of lipids that play important cellular roles both as structural components of membranes and as signaling molecules. They have also an active participation in apoptosis and inflammation processes which are associated with oxidative stress conditions. However, no studies so far accomplished the oxidative modification of sphingolipids under oxidative stress conditions. In the present study, different sphingolipids, ((d18:1/16:0) sphingomyelin ( N ‐palmitoyl‐ D ‐erythro‐sphingosylphosphorylcholine, SM), (d18:1) sphingosylphosphorylcholine (a lysosphingolipid, SPC), and (d18:1/18:0) ceramide (Cer)) were oxidized by the hydroxyl radical, generated under Fenton reaction conditions, and the oxidation reaction was monitored by ESI‐MS in positive mode. No oxidation products were identified for Cer under the oxidative conditions used, while ESI‐MS spectra of SPC and SM after oxidation show some oxidation products that were analyzed by ESI‐MS/MS. This approach allowed identifying hydroxyl and keto derivatives of SPC and acetaldehydephosphorylcholine derivative ( m / z 226). SM oxidation occurs exclusively in sphingosine backbone with formation of SPC, hydroxyl, and keto derivatives of SPC and the oxidation product at m / z 226. This study may give new insight and could help to understanding the behavior and biological roles of the sphingolipids under oxidative stress conditions.