A family of diacyltrehaloses isolated from Mycobacterium fortuitum

Ariza, Maria A.; Martin-Luengo, F.; Valero-Guillén, Pedro L.

doi:10.1099/13500872-140-8-1989

Cited by 21 publications

(22 citation statements)

References 31 publications

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“…The eluates (each 200-300 ml) were monitored for various types of lipids on TLC silica gel 60 F #&% plates (Merck) using chloroform\methanol\water (65 : 25 : 4, by vol.). The positions of the separated compounds were detected by spraying with a 5 % (w\v) ethanolic solution of molybdophosphoric acid, followed by heating for 10 min at 180 mC (visualization of all lipid-containing compounds) (Ariza et al, 1994). To detect sugar-containing lipids, the plates were sprayed with orcinol (0n5%, w\v, in 3 % H # SO % in methanol) followed by heating.…”

Section: Lipid Analysismentioning

confidence: 99%

Polycations increase the permeability of Mycobacterium vaccae cell envelopes to hydrophobic compounds

et al. 2001

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Section: Lipid Analysismentioning

confidence: 99%

Polycations increase the permeability of Mycobacterium vaccae cell envelopes to hydrophobic compounds

et al. 2001

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“…chelonae and M. absccssus) and of a group of strains, the third biovariant complex of M. fortuitum, which is unique in its immunodiffusion pattern and acid production from various carbohydrates (LCvy-Frebault et al, 1983;Pattyn et al, 1974;Silcox et al, 1981). Chemical analyses of the representative strains of the lour species demonstrated the occurrence of species-specific alkali-labile glycolipid in M. fortuitum (Ariza et al, 1994;Gautier et al, 1992;Hamid et al, 1993;Tsang et al, 1984;Sempere et al, 1993) and alkalistable glycolipids in the three other species (L6pez Marin et al, 1991(L6pez Marin et al, , 1992(L6pez Marin et al, , 1994Tsang et al, 1984). The present study was performed to characterize specific glycolipids in six strains that belong to the third biovariant complex of M. fortuitum (mannitol-positive and inositol-positive) and showed that this group of organisms is heterogeneous, in agreement with the data obtained by others by means of genotypic (Kirschner et al, 1992;Springer et al, 1995) and biochemical approaches (Wallace et al, 1991).…”

Section: Discussionmentioning

confidence: 99%

“…Replacement of an acetyl group by a fatty acyl substituent may explain the difference in the mobilities of the two glycolipids, as almost identical fatty acyl residues were identified in both studies. Nevertheless, the presence o f a tetraacylated triglucoside may typify some strains of the third biovariant complex, since biochemically well-characterized strains of M. fortuitum, including the type strain, were shown to synthesize alkali-labile glycolipids that consisted of 2,3-acy12trehalose, 2,3,4-acy13trehalose and 2,3,6-acy13trehalose (Ariza et al, 1994;Gautier et al, 1992;Hamid et al, 1993;Sempere et al, 1993). These acyltrehaloses differ from the major alkali-labile glycolipid of the third biovariant complex both in the structure of the carbohydrate moiety and in the location of the acyl substitutents, which suggests that the latter compound is not biosynthetically derived from the former substances.…”

Section: Discussionmentioning

confidence: 99%

“…Recent studies have established the structures of the alkali-labile glycolipids of M . fortuitum (Ariza et al, 1994;Besra et al, 1992;Gautier et al, 1992;Hamid et al, 1993;Sempere et al, 1993) and of the alkali-stable glycopeptidolipids of M. peregrinum (Lbpez Marin et al, 1991. The present study describes the structures of the major glycolipid antigens of selected strains of the third biovariant complex of M. fortuitum by means of conventional chemical analyses, MS and one-dimensional and two-dimensional NMR spectroscopy.…”

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confidence: 99%

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Structures of the Glycolipid Antigens of Members of the third Biovariant Complex of Mycobacterium Fortuitum

Lanéelle

Silve

López-Marı́n

et al. 1996

European Journal of Biochemistry

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Among the fast-growing mycobacteria, members of the Mycobacterium fortuitum complex are the most-commonly cited opportunistic human pathogens, notably in post-surgical infections. Previous studies showed that this complex was composed of four well-identified species and a group of isolates that did not correspond to recognized species, which has been referred to as the third biovariant complex. The occurrence and chemical structure of the glycolipid antigens of six strains that belong to this latter group were examined in the present study. Based on the TLC profiles, resistance to alkali and seroreactivities of their glycolipids, the examined strains were classified into three groups: one group was devoid of species-specific glycolipid and the two other groups contained alkali-stable or alkali-labile glycoconjugates. The structures of the major glycolipid antigens of the latter two groups were elucidated by fastatom-bombardment MS, one-dimensional and two-dimensional NMR spectroscopy and conventional chemical analyses. The alkali-stable glycolipids were structurally identical to the C-mycoside-type glycopeptidolipids characterized in the taxonomically related species Mycobacterium peregrinum. The major alkali-labile glycolipid was identified as ~-Glcp-(1-+6)-a-Glcp2Acyl-(l-l)-a-Glcp3,4,6Acyl,. The acyl substituents consisted of one acetyl group and three fatty acyl residues composed mainly of tetradecanoyl residues, but significant amounts of 2-methylhexadecanoyl and 2-methyloctadecanoyl substituents were also present. The heterogeneity of the glycolipid content of members of the third biovariant complex of M. fortuitum demonstrated in the present study confirms the heterogeneity of the complex. In addition, the occurrence of a species-specific glycolipid in some strains supports the hypothesis that some strains of this complex of M. fortuitum may belong to a new mycobacterial species.Keywords: antigen ; glycopeptidolipid ; lipooligosaccharide ; mycobacteria.Interest in mycobacteria other than Mycobacterium tuberculosis has been renewed by the increased frequency of clinical infections caused by these organisms (Woods and Washington, 1987). Unlike M. tuberculosis, whose host is man, most other mycobacteria are environmental microorganisms widely distributed in nature. Among the fast-growing mycobacteria, the mostcommonly cited opportunistic human pathogens, notably in post-surgical infections, are members of the Mycobacterium fortuitum complex (Good, 198.5). Biovariants and subspecies of this complex have frequently been misidentified and can, with difficulty, be recognized as distinct species. Strains that belong to this complex are resistant to most antimycobacterial drugs, and their response to other antimicrobial agents depends on the species and biovariant or subspecies (Good, 1985). The the third biovariant (LCvy-Frtbault et al., 1983). The glycolipid content of M. fortuitum differs from that of M. peregrinum

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“…The resulting monomethyl branched shortchain acids were found in SLs, PATs, and the more polar DATs. Such unsaturated monomethyl branched acids have been reported in the various glycolipids of Mycobacterium fortuitum (1,16,26,30), but their presence in M. tuberculosis has not been previously noted. The use of [1-14 C]propionic acid and careful separation of the methyl esters by argentation chromatography allowed us to detect these minor components.…”

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Biochemical Function of msl5 ( pks8 plus pks17 ) in Mycobacterium tuberculosis H37Rv: Biosynthesis of Monomethyl Branched Unsaturated Fatty Acids

et al. 2003

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We show that the disruption of one of the mycocerosic acid synthase (mas)-like genes, msl5 (pks8 plus pks17) in Mycobacterium tuberculosis H37Rv generates a mutant incapable of producing monomethyl branched unsaturated C 16 to C 20 fatty acids that are minor constituents of acyltrehaloses and sulfolipids. The msl5 mutation did not cause any significant change in the acyl lipid composition and also did not affect growth in culture, in mouse alveolar macrophage cell line MH-S, or in the murine lung.Mycobacterium tuberculosis infection is present in a latent form in one-third of the world population, and 5 to 10% of them will probably develop active tuberculosis some time during their life. This disease accounts for more than a quarter of all preventable adult deaths (32). The high degree of success of this pathogen is, to a large extent, due to its ability to evade the natural host defenses and antimycobacterial therapy. The unusually lipid-rich (50 to 60%) cell wall of the pathogen, which constitutes an impermeable barrier, plays a major role in its ability to successfully infect its host (12,19,21,23). Reflecting the unusual variety and content of lipids in this organism, its genome contains an unusually large number of genes that show homology to genes involved in lipid metabolism (7). Many of these belong to the polyketide synthase (pks) family. These genes encode large multifunctional proteins that contain all of the domains required to catalyze the various steps involved in fatty acid synthesis. One of these, mycocerosic acid synthase, which catalyzes the synthesis of multiple methyl branched fatty acids, has been purified and characterized (22), and the gene that encodes this protein (mas) has been cloned (20). Because isolation and characterization of the many large proteins of similar size and similar functions would pose a technical challenge, a genetic approach has been used to identify the biochemical functions of the pks genes. Based on the lipids missing in the mutants in which specific pks genes have been disrupted, the biochemical functions of some pks genes have been deduced (3,6,9,14,24,(27)(28)(29). However, the biochemical functions of most pks genes remain unknown.Based on homology to catalytic domains involved in fatty acid synthesis, pks8 would encode ketoacyl synthase (KS), acyl transferase (AT), dehydratase (DH), and enoyl reductase (ER) domains, whereas the adjoining pks17 gene would encode a ketoreductase (KR) and acyl carrier protein (ACP) domain. Thus, the products of pks8 and pks17 together would contain a complete set of domains required to make a saturated fatty acid. Because of its similarity to mas, we designated this combination of pks8 and pks17 as msl5 (27). To elucidate the nature of the branched fatty acids generated by the msl5 gene product, we disrupted this gene and used [1-14 C]propionic acid as a radiotracer to identify the fatty acids missing in the msl5 mutant. We report that this approach identified the msl5 product as the one responsible for the synthesis of 2-methyl...

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A family of diacyltrehaloses isolated from Mycobacterium fortuitum

Cited by 21 publications

References 31 publications

Polycations increase the permeability of Mycobacterium vaccae cell envelopes to hydrophobic compounds

Polycations increase the permeability of Mycobacterium vaccae cell envelopes to hydrophobic compounds

Structures of the Glycolipid Antigens of Members of the third Biovariant Complex of Mycobacterium Fortuitum

Biochemical Function of msl5 ( pks8 plus pks17 ) in Mycobacterium tuberculosis H37Rv: Biosynthesis of Monomethyl Branched Unsaturated Fatty Acids

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