Glycolipids of Recent Clinical Isolates of Mycobacterium tuberculosis: Chemical Characterization and Immunoreactivity

Daffé, Mamadou; Papa, F; László, A; David, Hugo L.

doi:10.1099/00221287-135-10-2759

Cited by 24 publications

(19 citation statements)

References 10 publications

(5 reference statements)

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“…A temperature gradient of 100 to 280ЊC (2Њ min Ϫ1 ) was used. Purified sulfatide was subjected to desulfation (16) by the method of Daffé et al (11).…”

Section: Tuberculosismentioning

confidence: 99%

Chemical characterization of the ester-linked 3-hydroxy fatty acyl-containing lipids in Mycobacterium tuberculosis

et al. 1995

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In a previous study (S. Alugupalli, F. Portaels, and L. Larsson, J. Bacteriol. 176:2962-2969, 1994), we reported the occurrence of 21 3-hydroxy fatty acids (3-OH-FAs) in the methanolysis products of different mycobacterial species. The present study was undertaken in order to chemically characterize the ester-linked complex native forms of these acids in Mycobacterium tuberculosis. Three 3-OH-FA-containing lipids were purified by chromatography and analyzed by one-and two-dimensional nuclear magnetic resonance spectroscopy, by fast atom bombardment-mass spectrometry, and by various conventional chemical analysis techniques. 3-OH-2,4,6-trimethyl-FAs were found in 2,3-diacyl trehalose and 2,3,6,6 -tetra-acyl-2 -sulfate trehalose (sulfatide I), two specific glycolipids of the tubercle bacillus, explaining the specific occurrence of these fatty acids in the methanolysis products of virulent strains of M. tuberculosis. Straight-chain 3-OH-FAs were localized in phosphatidyl ethanolamine but not in the other phospholipids, suggesting a possible role of this class of phospholipids in the metabolism of fatty acids in actinomycetes.Tuberculosis remains the leading cause of death in the world from a single pathogen (7,18). The slow growth of the tubercle bacillus and the lack of easy and reliable tests for detecting the disease at an early stage also limit the program of control and eradication of tuberculosis. In this context, recent efforts have been devoted to more knowledge of the disease and its pathogen.Most of the unique features of mycobacteria, such as their mold-like growth pattern and their resistance to chemical agents, as well as many of their biologic activities have been attributed to their high lipid content (17). Detailed chemical studies demonstrated the diversity and the complexity of the mycobacterial fatty acids, which have been used in chemotaxonomy in order to discriminate among mycobacterial species (4,8,24). These compounds include 2-alkyl branched, 3-hydroxylated long chain fatty acids (up to 90 carbon atoms), the so-called mycolic acids, multi-methyl (Me) branched-chain fatty acids having chiral centers with an L or D configuration, and ␣,␤-unsaturated compounds. We recently characterized 21 3-hydroxy fatty acids (3-OH-FAs), i.e., straight-chain and 2-Me and 2,4,6-tri-Me branched-chain fatty acids, in 27 strains belonging to 12 mycobacterial species (2). According to their 3-OH-FA patterns, the mycobacterial species could be subdivided into six groups, suggesting a taxonomic interest for these fatty acids. Virulent strains of Mycobacterium tuberculosis exhibited an unique pattern of 3-OH-FAs in that they contain multi-Me branched long chain hydroxy fatty acids, the potential precursors of fatty acids found in the biologically important mycobacterial lipids (4, 24). The present study was undertaken in order to chemically characterize the ester-linked native forms of straight-and Me branched-chain 3-OH-FAs in M. tuberculosis.M. tuberculosis H37Rv was grown for 4 weeks on Sauton's medium (26) as sur...

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“…A temperature gradient of 100 to 280ЊC (2Њ min Ϫ1 ) was used. Purified sulfatide was subjected to desulfation (16) by the method of Daffé et al (11).…”

Section: Tuberculosismentioning

confidence: 99%

Chemical characterization of the ester-linked 3-hydroxy fatty acyl-containing lipids in Mycobacterium tuberculosis

et al. 1995

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“…One such lipid is PGL, a glycolipid produced universally by Mycobacterium leprae but sporadically by M. tuberculosis strains (17). Recently, a globally disseminated clinical strain was shown to be hypervirulent for mice.…”

Section: Introductionmentioning

confidence: 99%

Trans-cyclopropanation of mycolic acids on trehalose dimycolate suppresses Mycobacterium tuberculosis-induced inflammation and virulence

Rao¹

2006

Journal of Clinical Investigation

179

120

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“…However, it has been shown that both GPL-positive and GPL-negative strains of Mycobacterium avium-M. intracellulare are surrounded by capsules (53). Similarly, some tubercle bacilli, notably the Canetti and Canetti-like strains, synthesize large amounts of PGLs (12,14,19), whereas other virulent strains contain only traces, if any at all, of these molecules (11,12,51). These observations suggested that PGLs and GPLs are not the major components of the mycobacterial capsule and that M. leprae and M. lepraemurium are anomalous in producing such very large amounts of lipids (22).…”

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confidence: 99%

Identification of the surface-exposed lipids on the cell envelopes of Mycobacterium tuberculosis and other mycobacterial species

et al. 1996

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The surface-exposed lipids of Mycobacterium tuberculosis, Mycobacterium avium, Mycobacterium kansasii, Mycobacterium gastri, Mycobacterium smegmatis, and Mycobacterium aurum were isolated by gentle mechanical treatment of cells with glass beads. Analysis of the exposed lipids demonstrated a selective location of classes of ubiquitous lipids on the surfaces of mycobacteria. While phosphatidylethanolamine and phosphatidylinositol mannosides were exposed in all the species examined, dimycoloyl trehalose (''cord factor'') was identified in the surface components of M. aurum only. Furthermore, monomycoloyl trehaloses and triacylglycerides were identified in the surface-exposed lipids of M. avium and M. smegmatis but not in those of the other mycobacterial species examined. The species-and type-species specific lipids were present on the mycobacterial cell surface: phenolic glycolipids, dimycocerosates of phthiocerols, and lipooligosaccharides were identified in the surface-exposed materials of M. tuberculosis (Canetti), M. kansasii, and M. gastri, whereas glycopeptidolipids were identified in the outermost lipid constituents of M. avium and M. smegmatis. This difference in the surface exposure of lipids of various mycobacterial species may reflect differences in their cell envelope organizations. Brief treatments of M. tuberculosis with Tween 80 prior to the use of glass beads led to erosion of regions of the capsule to expose gradually both cord factor and other lipids on the cell surface of the tubercle bacillus, demonstrating that the latter lipids are buried more deeply in the cell envelope and leading to the proposal of a scheme for the location of the capsular lipids of the tubercle bacillus.

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Glycolipids of Recent Clinical Isolates of Mycobacterium tuberculosis: Chemical Characterization and Immunoreactivity

Cited by 24 publications

References 10 publications

Chemical characterization of the ester-linked 3-hydroxy fatty acyl-containing lipids in Mycobacterium tuberculosis

Chemical characterization of the ester-linked 3-hydroxy fatty acyl-containing lipids in Mycobacterium tuberculosis

Trans-cyclopropanation of mycolic acids on trehalose dimycolate suppresses Mycobacterium tuberculosis-induced inflammation and virulence

Identification of the surface-exposed lipids on the cell envelopes of Mycobacterium tuberculosis and other mycobacterial species

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