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

Ellis, S.R., Hughes, J.R., Mitchell, T.W., Panhuis, M.I.H., & Blanksby, S.J. (2012) Using ambient ozone for assignment of double bond position in unsaturated lipids. The Analyst, 137(5), pp. 1100-1110.

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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.

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ID Code: 70666
Item Type: Journal Article
Refereed: Yes
Additional Information: Ellis, Shane R. Hughes, Jessica R. Mitchell, Todd W. Panhuis, Marc In Het Blanksby, Stephen J.
Australian Postgraduate Award; ARC Centre of Excellence for Free Radical Chemistry and Biotechnology [CE0561607]; Australian Research Council [DP0986628, FT0990846]
S.R E. and J.R.H. are supported by Australian Postgraduate Awards and S. R. E. is grateful to the University of Wollongong for travel support. S.J.B. acknowledges research funding from the ARC Centre of Excellence for Free Radical Chemistry and Biotechnology (CE0561607). T. W. M. and M. in het P. are grateful to the Australian Research Council for research support (DP0986628 and FT0990846, respectively). The authors also acknowledge Prof. Roger Truscott ( Save Sight Institute, University of Sydney, NSW, 2001, Australia) for provision of the human lens tissue along with Prof. Graham Cooks and Chunping Wu (Purdue University, Indiana, 47907, USA) for helpful discussions.
Royal soc chemistry
Cambridge
Keywords: desorption electrospray-ionization, tandem mass-spectrometry, thin-layer-chromatography, pulmonary-function changes, fatty-acids, structural-characterization, human lens, phospholipids, phosphatidylcholine, glycerophospholipids
DOI: 10.1039/c1an15864c
ISSN: 0003-2654
Divisions: Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 29 Apr 2014 04:16
Last Modified: 02 May 2014 01:27

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