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Photooxidation of glycated and non‐glycated phosphatidylethanolamines monitored by mass spectrometry
Authors:Tânia Melo  Eduarda M P Silva  Cláudia Simões  Pedro Domingues  M Rosário M Domingues
Institution:1. Mass Spectrometry Centre, QOPNA, Department of Chemistry, University of Aveiro, , 3810‐193 Aveiro, Portugal;2. Organic Chemistry Group, QOPNA, Department of Chemistry, University of Aveiro, , 3810‐193 Aveiro, Portugal
Abstract:Phosphatidylethanolamines (PE) are one of the major components of cells membranes, namely in skin and in retina, that are continuously exposed to solar UV radiation being major targets of photooxidation damage. In addition, due to the presence of the free amine group, PE can also undergo glycation, in hyperglycemic conditions which may increase the susceptibility to oxidation. The aim of this study is to develop a model, based on mass spectrometry (MS) analysis, to identify photooxidative degradation of selected PE (POPE: PE 16:0/18:1, PLPE: PE 16:0/18:2, PAPE: PE 16:0/20:4) and glycated PEs due to UV irradiation. Photooxidation products were analysed by electrospray ionization MS (ESI‐MS) and tandem MS (ESI‐MS/MS) in positive and negative mode. Emphasis is placed in the influence of glycation in the generation of distinct photooxidation products. ESI‐MS spectra of PE after UV photo‐irradiation showed mainly hydroperoxy derivatives, due to oxidation of unsaturated fatty acyl chains. Glycated PE gave rise to several new photooxidation products formed due to oxidative cleavages of the glucose moiety, namely between C1 and C2, C2 and C3, and C5 and C6 of this sugar unit. These new products were identified by ESI‐MS/MS in positive mode showing distinct neutral loss depending on the different structure of the polar head group. These new identified advanced glycated photooxidation products may have a deleterious role in the etiology of diabetic retinopathy and in diabetic retinal microvascular complications. Copyright © 2013 John Wiley & Sons, Ltd.
Keywords:photooxidation  phospholipids  UV  electrospray  tandem mass spectrometry  advanced glycated end products
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