Characterization of inositol phosphorylceramides from <i>Leishmania major</i> by tandem mass spectrometry with electrospray ionization

Hsu, Fong‐Fu; Turk, John; Zhang, Kai; Beverley, Stephen M.

doi:10.1016/j.jasms.2007.05.017

Cited by 68 publications

(69 citation statements)

References 32 publications

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“…The presence of PI-Cers is an interesting fi nding of this study, as this is a class of lipid known to be present in fungi such as Saccharomyces cerevisiae ( 39 ) and Aspergillus niger ( 40 ). They have also been found in protozoan pathogens like Trichomonas brucei ( 41 ), Trypanosoma brucei ( 41 ), Leishmania major ( 42 ), and plants ( 43 ). However, to our knowledge, the occurrence of bacterial PI-Cers has never been previously described.…”

Section: Discussionmentioning

confidence: 94%

A comprehensive insight into the lipid composition of Myxococcus xanthus by UPLC-ESI-MS

Lorenzen

Bozhüyük

Cortina

et al. 2014

Journal of Lipid Research

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This article is available online at http://www.jlr.org that allows researchers to investigate the lipid repertoire of these bacteria as a whole, in order to unveil alterations in the lipid composition on the molecular level as a function of different metabolic conditions or growth stages.In recent years, progress has been made in elucidating the biosynthesis and putative biological importance of myxobacterial FAs including branched-chain ( 6 ), straightchain ( 7 ), unsaturated ( 8 ), and hydroxylated FAs, as well as sphingoid species ( 9 ), particularly with regard to the best studied myxobacterial model organism Myxococcus xanthus . In these studies, methanolysis-derived FA methyl esters (FAMEs) or selected lipid classes were analyzed by means of GC-MS; there is thus only limited information about the complete lipidome of M. xanthus . High temperature GC-MS was applied to unhydrolyzed lipid extracts in order to elucidate the structures and relative abundance of neutral lipids ( 10 ) and unusual iso-branched alkyldiacylglycerols ( 4 ), molecules that exhibit signaling functions in this organism ( 5 ). HPLC ESI-MS/MS experiments were used to determine changes in the glycerophosphoethanolamine (PE) composition of mutant strains with inactivated acyltransferases ( 11 ) on the one hand, and to determine the ratio of certain ether PEs to acyl PEs during the process of starvation-induced fruiting body formation ( 4 ) on the other hand. In a recent publication on the myxobacterial ether lipid biosynthesis and the importance of these lipids for the myxobacterial life cycle ( 12 ), all these methods had to be combined in order to examine the effects of gene inactivations on the lipid composition of the respective mutants, as the occurrence and abundance of Myxobacteria are a globally occurring order of soildwelling Gram-negative ␦ -proteobacteria that attracts interest due to a wide range of remarkable features including cooperative motility, predation, simple multicellularity [including fungi-like fruiting body formation ( 1 )], and as producers of a wide range of secondary metabolites ( 2 ). Additionally, they exhibit a complex pattern of primary metabolites, with fatty acyl species and associated lipids the most well-studied. Some of these lipids are involved in processes like chemotaxis or starvation-induced fruiting body formation, either as biomarkers or chemotactic signals ( 3-5 ). However, to date, no methodology has been described This work was supported in part by the Emmy Noether program of the Deutsche Forschungsgemeinschaft (DFG).

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Section: Discussionmentioning

confidence: 94%

A comprehensive insight into the lipid composition of Myxococcus xanthus by UPLC-ESI-MS

Lorenzen

Bozhüyük

Cortina

et al. 2014

Journal of Lipid Research

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“…The 1-O-octadec-1=-enyl-2-oleoyl-sn-glycero-3-phosphoethanolamine was purchased from Avanti Polar Lipid Co. (Alabaster, Al), while the 1-O-octadecanyl-2-steroyl-sn-glycero-3-phosphoethanolamine was prepared by hydrogenation of 1-O-octadec-1=-enyl-2-oleoyl-snglycero-3-phosphoethanolamine. The lipid extracts from Leishmania major (L. major) and African trypanosomes were prepared as previously described [8,9].…”

Section: Methodsmentioning

confidence: 99%

Differentiation of 1-O-alk-1′-enyl-2-acyl and 1-O-alkyl-2-acyl Glycerophospholipids by Multiple-Stage Linear Ion-Trap Mass Spectrometry with Electrospray Ionization

Hsu

Turk

2007

J. Am. Soc. Mass Spectrom.

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We described linear ion-trap mass spectrometric approaches applying MS(3) and MS(4) toward to the structural characterization of 1-O-alk-1'-enyl-2-acyl-, 1-O-alkyl-2-acyl-, and diacyl-glycerophospholipids (GPL) as the [M - H](-) ions desorbed by ESI in negative-ion mode. Further dissociation of the [lM - H - R(2)CO(2)H - polar head group](-) ions from the [M - H](-) ions of GPL that have undergone the consecutive losses of the fatty acid substituent at sn-2 and the polar head group readily gives the structural information of the radyl group at sn-1, resulting in structural differentiation among the 1-O-alk-1'-enyl-2-acyl-, 1-O-alkyl-2-acyl, and diacyl-glycerolphospholipid molecules. The distinction between a 1-O-alk-1'-enyl-2-acyl- and a 1-O-alkyl-2-acyl-GPL is based on the findings that the MS(3) (or MS(4)) spectrum of the [M - H - R(2)CO(2)H - polar head group](-) ion from the former compound is dominated by the alkenoxide anion that represents the radyl moiety at sn-1, while the spectrum from the latter compound is dominated by the ion at m/z 135 arising from further loss of the 1-O-alkyl group as an alcohol. Another important notion is that the optimal collision energy required for acquiring the former spectrum is significantly lower than that required for obtaining the latter spectrum. Using the approaches, we are able to reveal the structures of several isobaric isomers in GPL mixtures of biological origin. Because the [M - H](-) ions are readily formed by various GPL classes (except glycerophosphocholine) in the negative-ion mode, these mass spectrometric approaches should have broad application in the structural identification of GPLs.

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“…Since the long chain base (sphingoid base) of SLs is synthesized through the condensation of serine and fatty acyl-CoA, it is concluded that Leishmania enzyme preferentially incorporates myristoyl-CoA (C14) over palmitoyl-CoA (C16) into their long chain base and ceramide (Fig. 1E) [47]. This differs from mammalian cells which mostly use palmitoyl-CoA to synthesize their SLs [48]; or yeasts ( S. cerevisiae ) in which palmitoyl Co-A is the preferred substrate [49] and in vivo sphingoid bases arise primarily from C16 and C18 acyl-CoA [50].…”

Section: Composition Of Pls and Sls In Leishmaniamentioning

confidence: 99%

“…Two ORFs with homology to SPT1 and SPT2 have been identified from the L. major genome with SPT2 being the putative catalytic subunit. It is noteworthy that the main IPC species in L. major contains C16 as the long chain base, suggesting that L. major SPT prefers myristoyl-CoA over palmitoyl-CoA as a substrate [27, 47]. Deletion of SPT2 in L. major results in a complete loss of IPC and other SLs.…”

Section: Metabolismmentioning

confidence: 99%

Phospholipid and sphingolipid metabolism in Leishmania

Zhang

Beverley

2010

Molecular and Biochemical Parasitology

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In many eukaryotes, phospholipids (PLs) and sphingolipids (SLs) are abundant membrane components and reservoirs for important signaling molecules. In Leishmania, the composition, metabolism, and function of PLs and SLs differ significantly from those in mammalian cells. Although only a handful of enzymes have been experimentally characterized, available data suggest many steps of PL/SL metabolism are critical for Leishmania viability and/or virulence, and could be a source for new drug targets. Further studies of genes involved in the synthesis (de novo and salvage) and degradation of PLs and SLs will reveal their diverse effects on Leishmania pathogenesis.

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Characterization of inositol phosphorylceramides from Leishmania major by tandem mass spectrometry with electrospray ionization

Cited by 68 publications

References 32 publications

A comprehensive insight into the lipid composition of Myxococcus xanthus by UPLC-ESI-MS

A comprehensive insight into the lipid composition of Myxococcus xanthus by UPLC-ESI-MS

Differentiation of 1-O-alk-1′-enyl-2-acyl and 1-O-alkyl-2-acyl Glycerophospholipids by Multiple-Stage Linear Ion-Trap Mass Spectrometry with Electrospray Ionization

Phospholipid and sphingolipid metabolism in Leishmania

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