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Papers In Press, published online ahead of print September 1, 2007
J. Lipid Res., doi:10.1194/jlr.M700060-JLR200

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Journal of Lipid Research, Vol. 48, 1976-1984, September 2007
Copyright © 2007 by American Society for Biochemistry and Molecular Biology

Sensitive profiling of chemically diverse bioactive lipids

Guanghou Shui^1,*, Anne K. Bendt^1,*, Kevin Pethe, Thomas Dick and Markus R. Wenk^2,*,

^* Yong Loo Lin School of Medicine, National University of Singapore, Department of Biochemistry, Singapore, 117597
Novartis Institute for Tropical Diseases, Singapore, 138670
Department of Biological Sciences, Singapore, 117597

The online version of this article (available at http://www.jlr.org) contains supplementary data in the form of one figure.

Published, JLR Papers in Press, June 12, 2007.

¹ G. Shui and A. K. Bendt contributed equally to this work.

² To whom correspondence should be addressed. e-mail: bchmrw{at}nus.edu.sg

Here, we present an improved method for sensitive profiling of lipids in a single high-performance liquid chromatography-electrospray ionization-quadrupole time of flight mass spectrometry experiment. The approach consists of i) sensitive isocratic elution, which takes advantage of C18 column material that is resistant to increased pH values induced by piperidine, ii) chemometric alignment of mass spectra followed by differential analysis of ion intensities, and iii) semiquantitative analysis of extracted ion chromatograms of interest. A key advantage of this method is its wide applicability to extracts that harbor lipids of considerable chemical complexity. The method allows qualitative and semiquantitative analysis of fatty acyls, glycerophospholipids (such as glycerophosphatidylinositols, glycerophosphatidylserines, and glycerophosphatidylcholines in brain extracts), phosphatidylinositol mannosides, acylated glycerophospholipids, sphingolipids (including ceramides and gangliosides in brain extracts), and, for the first time with ESI, prenols and mycolic acids (MAs). MAs are targets in antimycobacterial therapy, and they play an important immunomodulatory role during host-pathogen interactions. We compared high-resolution mass spectra of MAs derived from Mycobacterium bovis Bacille Camette-Guérin during entry into nonreplicative conditions induced by oxygen deprivation (hypoxic dormancy). Although the overall composition is not drastically altered, there are pronounced differences in individual MAs. -MAs accumulate during entry into dormancy, whereas a subpopulation of keto-MAs is almost entirely eliminated. This effect is reversed upon resuscitation of dormant mycobacteria. These results provide detailed chemical information with relevance to drug development and immunobiology of mycobacteria.

Supplementary key words lipidomics • liquid chromatography • mass spectrometry • mycobacteria • mycolic acids • drug development • host-pathogen interactions • hypoxic dormancy

Abbreviations: BCG, Bacille Camette-Guérin; COW, correlation-optimized warping; MA, mycolic acid; PIP, phosphatidylinositol polyphosphate; Q-TOF, quadrupole/time of flight

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