Structural and immunological properties of the phenolic glycolids from <i>Mycobacterium gastri</i> and <i>Mycobacterium kansasii</i>

Gilleron, Martine; Venisse, Anne; Fournié, Jean‐Jacques; Rivière, M.; Dupont, Marie-Ange; Gas, Nicole; Puzo, Germain

doi:10.1111/j.1432-1033.1990.tb15473.x

Cited by 19 publications

(14 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…kansasii and M. gastri showed the same profile as M. tuberculosis: PGLs (27, 57), DIMs (15,46), and LOSs (30,37) were surface exposed in these species, but DMTs, MMTs, and TAGs were not. The surface exposure of these species-specific lipids was in agreement with the immunocytochemical data showing the surface location of PGLs and LOSs on M. kansasii (4,29) and with the identification of PGLs and DIMs in the petroleum ether extract of this species (39). In connection with that agreement, it is interesting that DIMs, PGLs, and TAGs were detected in a petroleum ether extract of M. kansasii (39).…”

supporting

confidence: 88%

“…Because the interaction of the outermost constituents of the bacterial cell envelope with the phagocyte determines in part the immunological response of the host, the surface-exposed lipids may play a role in the pathogenesis of mycobacterial diseases. It is worthy of note that both PGLs and GPLs have been shown to be located on the cell surface (3,9,21,29) and to exhibit various immunomodulatory properties (10,26,44,52,56). In the present study, we adopted a novel approach to study the outermost capsular components, based on the release of superficial components by gentle mechanical abrasion, to define the chemical nature of the surface-exposed lipids of M. tuberculosis and other pathogenic and nonpathogenic mycobacterial species.…”

mentioning

confidence: 99%

See 1 more Smart Citation

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

et al. 1996

View full text Add to dashboard Cite

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.

show abstract

supporting

confidence: 88%

mentioning

confidence: 99%

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

et al. 1996

View full text Add to dashboard Cite

show abstract

“…The determination of the complete structure of one such GPL, containing alkaline-labile side chains, by chemical methods remains a difficult task and has led, in some cases, to the description of incomplete structures. For example, almost any chemical treatment allowing interglycosidic cleavage leads to the loss of the acyl chains, thereby preventing their detection, whereas it has been shown that these kinds of appendages are often of major importance to the biological properties of the the carbohydrate backbone (Gilleron et al, 1990). Thus all approaches which modify the molecular integrity of the investigated antigen must be used together with analytical methods allowing structural elucidation of the native form.…”

Section: Discussionmentioning

confidence: 99%

Structure of a novel glycopeptidolipid antigen containing a O‐methylated serine isolated from Mycobacterium xenopi

Rivière

Augé

Vercauteren³

et al. 1993

European Journal of Biochemistry

Self Cite

View full text Add to dashboard Cite

GPL X-1, a novel glycopeptidolipid (GPL) isolated from Mycobacterium xenopi ( C q 140 35004), has recently been found to typify a new class of mycobacterial glycopeptidolipids devoid of C-mycoside core structure, the so-called serine-containing glycopeptidolipid [Rivikre, M. & Puzo, G. (1991) J. Biol. Chem. 266,9057-90631. Here we report the purification and characterization of a novel serine-containing GPL termed GPL X-IIb, isolated from the M. xenopi strain NCTC 10042.On thin-layer chromatography, this GPL was found to be present in some other M. xenopi strains isolated from patients with pulmonary infections. The sugar and amino-acid compositions of this GPL were elucidated from the native form using a combination of two-dimensional homonuclear and heteronuclear scalar coupling NMR. The peptide and sugar sequences, as well as the methoxyl group locations on the C-3 of the 6-deoxy-a-~-talopyranoside (6dTalp) and on a Ser, were unambiguously determined by heteronuclear multiple-bond correlation experiments. GPL X-1% was found to be composed of a lipotetrapeptide of the following structure C,,-Ser-OMe-Ser-Phe-a%-OMe (aThr = allothreonine). The sugar part is made up of 30Me-a-~-6dTalp and the following disaccharide : a-~-Rhap-(1+3)-2-O-Lau-a-~-Rhap (Rhap = rhanmopyranose). Unlike GPL X-I, the sugar attachment sites on the tetrapeptide were successfully determined from heteronuclear three-bond coupling correlation observed in the heteronuclear multiple bond correlation spectrum between the anomeric carbon resonances and the protons of aThr-OMe and Ser. It was established that the 30Me-6dTalp glycosylates the Ser while the disaccharide is linked to the aThr-OMe. Thus both GPL X-I and GPL X-IIb share a common lipotetrapeptide core [with the exception of Ser(0Me)l but drastically differ in their oligosaccharide appendage. Thus, by analogy with the M. avium complex, the present report suggests that M. xenopi species can be divided in various serovars characterized by the unique structure of their C-mycoside GPL oligosaccharide appendage, enhancing the interest for this new type of serine-containing glycopeptidolipid.Research into mycobacterial infection has intensifying as a result of a resurgence in the prevalence of human tuberculosis. In developed countries, the epidemiology of the disease is changing, due mainly to the emergence of drug-resistant Mycobacterium tuberculosis strains (Weiss, 1992), but also from an increase in infections with nontuberculous mycobacteria such as Mycobacterium avium, Mycobacterium kansasii Correspondence to M.

show abstract

“…Similarly, M. kansasii and M . gastri accumulate the same phenolic mycosides (Gilleron et al, 1990;Papa et al, 1987;Vercellone et al, 1988) and were found to be indistinguishable according to their rRNA sequences (Rogall et al, 1990) and their fatty acid content (Daffk et al, 1983). Classical identification methods, however, easily differentiate M. kansasii, a potential pathogen frequently isolated in clinical samples, from M. gastri, a non-pathogenic species (Wayne & Kubica, 1986).…”

Section: M Dafk a Varnerot And V Vincent Lhy-fribaultmentioning

confidence: 99%

The phenolic mycoside of Mycobacterium ulcerans: structure and taxonomic implications

Daffé

Varnerot

Lévy-Frébault

1992

Journal of General Microbiology

View full text Add to dashboard Cite

Mycobacterium ufcerans and some pathogenic mycobacterial species elaborate wax A consisting of related longchain P-diol components (phthiocerol and related compounds) esterified by multimethyl-branched fatty acids. With the exception of M. ulcerans, wax A-containing mycobacteria also synthesize glycosylated phenol phthiocerol diester and related compounds: the so-called phenolic mycosides. In a deliberate effort to characterize this latter class of compounds in M. ufcerans, 20 strains were examined. Phenolic mycosides were found in two strains. Application of chemical analyses, including one-and two-dimensional N M R spectroscopy, allowed the structural elucidation of glycolipids identified as 3-O-methyl-a-~-rhamnosyl phenol phthiocerol diphthioceranate and related compounds which correspond to mycoside G , previously characterized in M. marinum by other investigators. As phenolic mycosides are highly species-specific molecules, this finding stresses the close phylogenetic link between M. marinurn and M. ulcerans. Incidentally, a survey of the mycolate content of M. ulcerans showed that methoxymycolate could not be detected in three strains.

show abstract

Structural and immunological properties of the phenolic glycolids from Mycobacterium gastri and Mycobacterium kansasii

Cited by 19 publications

References 33 publications

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

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

Structure of a novel glycopeptidolipid antigen containing a O‐methylated serine isolated from Mycobacterium xenopi

The phenolic mycoside of Mycobacterium ulcerans: structure and taxonomic implications

Contact Info

Product

Resources

About