Issue 5, 2012
From the journal:

Analyst

Using ambient ozone for assignment of double bond position in unsaturated lipids†

Shane R. Ellis,a   Jessica R. Hughes,b   Todd W. Mitchell,c   Marc in het Panhuisd  and  Stephen J. Blanksby*a  

* Corresponding authors

a ARC Centre of Excellence for Free Radical Chemistry and Biotechnology, School of Chemistry, University of Wollongong, Wollongong, NSW, Australia
E-mail: blanksby@uow.edu.au
Fax: +61 2 4221 4287
Tel: +61 2 4221 5484

b Graduate School of Medicine, University of Wollongong, Wollongong, NSW, Australia

c School of Health Sciences, University of Wollongong, Wollongong, NSW, Australia

d School of Chemistry, University of Wollongong, Wollongong, NSW, Australia

Abstract

Unsaturated lipids deposited onto a range of materials are observed to react with the low concentrations of ozone present in normal laboratory air. Parent lipids and ozonolysis cleavage products are both detected directly from surfaces by desorption electrospray ionisation mass spectrometry (DESI-MS) with the resulting mass spectra providing clear evidence of the double bond position within these molecules. This serendipitous process has been coupled with thin-layer chromatography (TLC) to provide a simple but powerful approach for the detailed structural elucidation of lipids present in complex biological extracts. Lipid extracts from human lens were deposited onto normal phase TLC plates and then developed to separate components according to lipid class. Exposure of the developed plates to laboratory air for ca. 1 h prior to DESI-MS analysis gave rise to ozonolysis products allowing for the unambiguous identification of double bond positions in even low abundant, unsaturated lipids. In particular, the co-localization of intact unsaturated lactosylceramides (LacCer) with products from their oxidative cleavage provide the first evidence for the presence of three isomeric LacCer (d18:0/24:1) species in the ocular lens lipidome, i.e., variants with double bonds at the n-9, n-7 and n-5 positions.

Graphical abstract: Using ambient ozone for assignment of double bond position in unsaturated lipids

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Article information

DOI
https://doi.org/10.1039/C1AN15864C
Article type
Paper
Submitted
16 Sep 2011
Accepted
10 Nov 2011
First published
25 Nov 2011

Analyst, 2012,137, 1100-1110

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Using ambient ozone for assignment of double bond position in unsaturated lipids

S. R. Ellis, J. R. Hughes, T. W. Mitchell, M. I. H. Panhuis and S. J. Blanksby, Analyst, 2012, 137, 1100 DOI: 10.1039/C1AN15864C

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