Characterization of phthiocerol dimycocerosates from Mycobacterium tuberculosis

Minnikin, David E.; Dobson, Gary; Hutchinson, I

doi:10.1016/0005-2760(83)90069-3

Cited by 14 publications

(14 citation statements)

References 12 publications

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“…In essence, mycolic acids are obtained by a special low-water alkaline hydrolysis procedure designed to release all long-chain compounds, including the components of the phthiocerol dimycocerosate waxes that are particularly resistant to normal hydrolytic methods (Minnikin et al, 1983). Long-chain acids in the hydrolysates are converted to stable pentafluorobenzyl esters, both to allow the analysis of mycocerosates by highly sensitive negative-ion chemical-ionisation gas chromatography mass spectrometry (NI-CI GC-MS) (Redman et al, 2009) and also preserve the extracted material for analysis with developing methodologies.…”

Section: Essential Data Necessary For the Use Of Mycolic Acid Profilementioning

confidence: 99%

Essentials in the use of mycolic acid biomarkers for tuberculosis detection: response to “High-throughput mass spectrometric analysis of 1400-year-old mycolic acids as biomarkers for ancient tuberculosis infection” by

Minnikin¹,

Lee²,

Pitts³

et al. 2010

Journal of Archaeological Science

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Section: Essential Data Necessary For the Use Of Mycolic Acid Profilementioning

confidence: 99%

Essentials in the use of mycolic acid biomarkers for tuberculosis detection: response to “High-throughput mass spectrometric analysis of 1400-year-old mycolic acids as biomarkers for ancient tuberculosis infection” by

Minnikin¹,

Lee²,

Pitts³

et al. 2010

Journal of Archaeological Science

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“…1 ) and PGL respectively consist of a longchain 3-methoxy, 4-methyl, 9,11-dihydroxy glycol (phthiocerol) and a p -glycosylated phenylglycol (glycosyl phenolphthiocerol) backbone diesterifi ed with di-, tri-, and tetra-methyl-branched long-chain mycocerosic (mycoceranic) acids ( 10,19,20 ). Dependent on the species, the long-chain diol backbone ranges in size from C 25 to C 36 , and the mycocerosic acid chain ranges from C 23 or C 24 to C 32 ( 3,4,10,21,22 ). Other variants with 3-keto or 3-hydroxy diols also exist.…”

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

confidence: 99%

“…For example, Minnikin et al ( 10,(24)(25)(26) and Daffe et al ( 9,(27)(28)(29) used GC/MS analysis together with NMR spectroscopy for complete characterization of DIMs, following extraction steps, chromato graphic separations, and chemical reactions. Recently, MALDI-TOF ( 16,29,30 ) and ESI-Fourier transform ion cyclotron resonance ( 31 ) MS have also been applied for profi ling PDIM and PGLs.…”

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

confidence: 99%

“…6 , inset). 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).…”

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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“…The mycocerosic and mycolipenic acids (Fig. 1B) are the beststudied examples, the former being components of phthiocerol dimycocerosate waxes and the latter being part of pentaacyl trehalose glycolipids (Minnikin et al, 1983(Minnikin et al, , 1985a(Minnikin et al, , 1985b. Mycocerosic acids are found in a limited number of mycobacterial species, including Mycobacterium kansasii, M. leprae and Mycobacterium haemophilum in addition to members of the MTBC; Mycobacterium marinum and Mycobacterium ulcerans have closely related acids .…”

Section: Established Lipid Biomarkers For Mtbcmentioning

confidence: 99%