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Papers In Press, published online ahead of print July 1, 2009
J. Lipid Res., doi:10.1194/jlr.M800478-JLR200

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Journal of Lipid Research, Vol. 50, 1363-1373, July 2009
Copyright © 2009 by American Society for Biochemistry and Molecular Biology

Positive and negative tandem mass spectrometric fingerprints of lipids from the halophilic Archaea Haloarcula marismortui

Lauro M. de Souza, Marcelo Müller-Santos, Marcello Iacomini, Philip A. J. Gorin and Guilherme L. Sassaki¹

Departamento de Bioquímica e Biologia Molecular, Universidade Federal do Paraná, CP 19046, CEP 81531-980, Curitiba-PR, Brazil

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

Published, JLR Papers in Press, March 2, 2009.

¹ To whom correspondence should be addressed. e-mail: sassaki{at}ufpr.br

Lipids from the extremely halophilic Archaea, Haloarcula marismortui, contain abundant phytanyl diether phospholipids, namely archaetidic acid (AA), archaetidylglycerol (AG), archaetidylglycerosulfate (AGS), with mainly archaetidylglycerophosphate methyl ester (AGP-Me). These were accompanied by a triglycosyl archaeol (TGA), lacking characteristic sulfate groups. Tandem-mass spectrometry was employed to provide fingerprints for identifying these known lipids, as well as small amounts of unsaturated phospholipids. These contained 3 and 6 double bonds in their archaeol moiety, suggested by negative tandem-MS of intact phospholipids, as indicated by differences between their pseudo-molecular ion and specific fragment ions designated as ₂. The core ether lipids were confirmed by electrospray ionization mass spectrometry (ESI-MS) as 2,3-di-O-phytanyl-sn-glycerol (C20, C20), which gave rise to a precursor-ion at m/z 660 [M+Li]⁺, and its fragment ion at m/z 379 [M+Li]⁺, consistent with mono-O-phytanyl-glycerol. Furthermore, lithiated ions at m/z 654 (MS¹), 379 (MS²) and m/z 648 (MS¹), 373 (MS²), combined with ¹H/¹³C NMR chemical shifts at 5.31-121.6 (C2/2'-H2/2'), 5.08-124.9 (C6/6'-H6/6') and 5.10-126.0 (10/10'-H10/10') confirmed the presence of unsaturated homologs of archaeol. We carried out a comprehensive study on the lipids present in cells of H. marismortui. We used positive and negative ESI-MS with tandem-MS, which served as a fingerprint analysis for identifying the majority of component lipids.

Supplementary key words fingerprint analysis • glycolipid • ¹H/¹³C NMR • Haloarcula marismortui • phospholipids • tandem-mass spectrometry

Abbreviations: AA, archaetidic acid; AG, archaetidylglycerol; AGP, archaetidylglycerophosphate; AGP-Me, archaetidylglycerophosphate methyl ester; AGS, archaetidylglycerosulfate; API, atmospheric pressure ionization; CID-MS, collision induced dissociation-mass spectrometry; ESI-MS, electrospray ionization-mass spectrometry; GC-MS, gas chromatography-mass spectrometry; HMQC, heteronuclear multiple quantum coherence; MS, mass spectrometry; m.u., mass units; m/z, mass to charge ratio; NL, neutral loss; NMR, nuclear magnetic resonance; PHG, polar head group; PMI, pseudo-molecular ion; TIC, total ion current; TGA, triglycosyl archaeol; TLC, thin layer chromatography

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