Characterization of polar lipids of Listeria monocytogenes by HCD and low-energy CAD linear ion-trap mass spectrometry with electrospray ionization

Tatituri, Raju V. V.; Wolf, Benjamin; Brenner, Michael B.; Turk, John; Hsu, Fong‐Fu

doi:10.1007/s00216-015-8480-1

Cited by 28 publications

(37 citation statements)

References 34 publications

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“…(13). For structural analysis of fatty acids, TLC-purified lipids were first treated via alkaline hydrolysis to liberate fatty acids, which were then isolated and derivatized with N-(4-aminomethylphenyl) pyridinium (AMPP), and subjected to MS as described (37). …”

Section: Methodsmentioning

confidence: 99%

Identification of a Potent Microbial Lipid Antigen for Diverse NKT Cells

Wolf

Tatituri

Almeida

et al. 2015

The Journal of Immunology

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Invariant Natural Killer T (iNKT) cells are a well-characterized CD1d-restricted T cell subset. The availability of potent antigens and tetramers for iNKT cells has allowed this population to be extensively studied and has revealed their central roles in infection, autoimmunity, and tumor immunity. In contrast, diverse Natural Killer T (dNKT) cells are poorly understood because the lipid antigens they recognize are largely unknown. We sought to identify dNKT cell lipid antigen(s) by interrogating a panel of dNKT mouse cell hybridomas with lipid extracts from the pathogen Listeria monocytogenes. We identified Listeria phosphatidylglycerol (PG) as a microbial antigen that was significantly more potent than a previously characterized dNKT cell antigen, mammalian PG. Further, while mammalian PG loaded CD1d tetramers did not stain dNKT cells, the Listeria-derived PG loaded tetramers did. The structure of Listeria PG was distinct from mammalian PG since it contained shorter, fully-saturated anteiso fatty acid lipid tails. CD1d binding lipid displacement studies revealed that the microbial PG antigen binds significantly better to CD1d than counterparts with the same headgroup. These data reveal a highly-potent microbial lipid antigen for a subset of dNKT cells and provide an explanation for its increased antigen potency compared to the mammalian counterpart.

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Section: Methodsmentioning

confidence: 99%

Identification of a Potent Microbial Lipid Antigen for Diverse NKT Cells

Wolf

Tatituri

Almeida

et al. 2015

The Journal of Immunology

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“…6 ) ( 34, 40-43 ), and ions from charge-remote fragmentations can locate the methyl side chains ( 34,43 ) and the functional groups unambiguously ( Fig. 6 , inset).…”

Section: Characterization Of Multiple-methyl-branched Long-chain Mycomentioning

confidence: 96%

“…Alkaline hydrolysis to yield myroceranoic acids from PDIM was carried out following the protocol as previously described ( 34 ) with modifi cation. To the tube containing dried PDIM, 400 l methanol, 200 l diethylether, and 200 l tetrabutylammonium hydroxide (40 wt% solution in water) were added.…”

Section: Alkaline Hydrolysis and Preparation Of N -(4-aminomethylphenmentioning

confidence: 99%

“…By contrast, the traditional GC/MS method for identifi cation of mycocerosic acids is laborious, requiring acid methanolysis to form the methyl ester, separated by TLC, followed by reductive degradation to mycocerosic alcohol and another two-dimensional TLC purifi cation, before formation of the fi nal t-butyldimethylsilyl ether derivatives (23)(24)(25). The superb sensitivity gained for the acid detected as the AMPP derivative (as compared with its underivatized form) also facilitates structural identifi cation and quantitation ( 34,(40)(41)(42)(43). This aspect may deserve further investigation.…”

Section: Characterization Of Multiple-methyl-branched Long-chain Mycomentioning

confidence: 99%

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Characterization of phthiocerol and phthiodiolone dimycocerosate esters of M. tuberculosis by multiple-stage linear ion-trap MS

Flentie

Stallings

Turk³

et al. 2016

Journal of Lipid Research

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This article is available online at http://www.jlr.org Both phthiocerol/phthiodiolone dimycocerosate (PDIM) esters and phenolic glycolipids (PGLs) are dimycocerosate esters (DIMs) produced by pathogenic mycobacteria. PDIMs were originally isolated from Mycobacterium tuberculosis (1)(2)(3)(4) and are specifi c tuberculosis biomarkers ( 5, 6 ). They are among the most abundant lipids in the cell wall of various pathogenic mycobacteria, including M. tuberculosis , M. bovis , M. leprae , M. kansasii , M. microti , and M. marinum ( 7-10 ), which are known to synthesize a range of complex highmolecular-mass lipids ( 7 ). PGLs are produced by the same set of pathogenic mycobacteria species, except that in M. tuberculosis only a subset of clinical isolates belonging to the W-Beijing family ( 11 ) produces PGLs.Phthiocerol and phenolphthiocerol and other lipids such as mycolic acids and methyl-branched FAs in cell wall are among those that have been most extensively studied in terms of their biosynthesis and the role in M. tuberculosis virulence in vivo ( 12 ). In pathogenesis, the role of PDIMs of M. tuberculosis was recognized by the studies that identifi ed that mutants of M. tuberculosis were unable to either produce or properly localize PDIMs to the cell envelopeand that demonstrated that PDIM-defi cient strains were attenuated in animal models of infection ( 8,11,(13)(14)(15)(16)(17). Recently, M. tuberculosis and its close pathogenic relative M. marinum were reported to manipulate macrophage recruitment through coordinated use of membrane PDIM and PGLs to initiate infections ( 18 ). However, the precise role of these molecules in the course of infection remains largely unknown, and their role in the multiplication of mycobacteria from the tuberculosis complex in organs other than the lungs is also unclear.

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“…More minor routes for metabolising PG are in producing amino acid derivatives [11,131,132] and producing PGs acylated with FARs [133]. It is also a source of phosphatidyl and of sn-glycerol-1-phosphate groups [134].…”

Section: Bacteriamentioning

confidence: 99%

Is phosphatidylglycerol essential for terrestrial life?

Furse

2016

J Chem Biol

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Lipids are of increasing importance in understanding biological systems. Lipids carrying an anionic charge are noted in particular for their electrostatic interactions with both proteins and divalent cations. However, the biological, analytical, chemical and biophysical data of such species are rarely considered together, limiting our ability to assess the true role of such lipids in vivo. In this review, evidence from a range of studies about the lipid phosphatidylglycerol is considered. This evidence supports the conclusions that this lipid is ubiquitous in living systems and generally of low abundance but probably fundamental for terrestrial life. Possible reasons for this are discussed and further questions posed.

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Characterization of polar lipids of Listeria monocytogenes by HCD and low-energy CAD linear ion-trap mass spectrometry with electrospray ionization

Cited by 28 publications

References 34 publications

Identification of a Potent Microbial Lipid Antigen for Diverse NKT Cells

Identification of a Potent Microbial Lipid Antigen for Diverse NKT Cells

Characterization of phthiocerol and phthiodiolone dimycocerosate esters of M. tuberculosis by multiple-stage linear ion-trap MS

Is phosphatidylglycerol essential for terrestrial life?

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