Contribution à l'étude de la structure et de la biosynthèse de glycolipides spécifiques isolés de mycobactéries: les mycosides A et B

Gastambide-Odier, M; Sarda, Pierre

doi:10.1007/bf02095222

Cited by 32 publications

(16 citation statements)

References 20 publications

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“…Information about the biosynthesis of the phenolic glycolipids is limited. The carbon atoms in the methyl-branched structures in mycocerosic acids are derived from propionate (Gastambide-Odier et al, 1963 a;Yano and Kusunose, 1966), as are those in phthiocerol (GastambideOdier et al, 1967;Gastambide-Odier and Sarda, 1970). The aromatic ring can be derived from tyrosine (Gastambide-Odier and Sarda, 1970), though not from phenylalanine.…”

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“…The carbon atoms in the methyl-branched structures in mycocerosic acids are derived from propionate (Gastambide-Odier et al, 1963 a;Yano and Kusunose, 1966), as are those in phthiocerol (GastambideOdier et al, 1967;Gastambide-Odier and Sarda, 1970). The aromatic ring can be derived from tyrosine (Gastambide-Odier and Sarda, 1970), though not from phenylalanine. The methoxyl residue in phenolphthiocerol presumably comes from methionine, by analogy with the known source in the related lipid phthiocerol (Gastambide-Odier et al, 1963 b).…”

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Possible intermediates in the biosynthesis of mycoside B by Mycobacterium microti

Thurman

Chai²,

Rosankiewicz³

et al. 1993

European Journal of Biochemistry

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Two lipids were isolated from Mycobacterium microti which became labelled when the cells were grown in the presence of [2-14C]propionate. They were purified by thin-layer chromatography and studied by chemical degradation and mass spectrometry. The lipids were identified as phenolphthiocerol dimycocerosate and phenolphthiodiolone dimycocerosate, the aglycosyl derivatives of mycoside B, the phenolic glycolipid produced by M. microti. Cell-free extracts of the organism were able to glycosylate the lipids to form mycoside B in vitro. It is probable that the lipids are intermediates in the biosynthesis of phenolic glycolipids by mycobacteria.Mycoside B (2-0-methylrhamnosyl phenolphthiocerol dimycocerosate, a typical 'phenolic glycolipid') was originally isolated from Mycobacterium bovis as part of a programme to identify mycobacterial species from their characteristic lipids (Maclennan et al., 1960). Related lipids bearing oligosaccharides rather than a single sugar, notably the characteristic phenolic glycolipids from M. Zeprue (PGL-I ; Hunter et al., 1982) and from some strains of M. tuberculosis (DaffC et al., 1987), have excited much interest as speciesspecific antigens. The molecules also possess biological properties which may have to do with the ability of mycobacterial pathogens to survive inside host cells (Chan et al., 1989;Mehra et al., 1984; Schlesinger and Horwitz, 1991;Sut et al., 1990;Vachula et al., 1989).Phenolic glycolipids consist of a phenolphthiocerol core containing a 1 : 3 glycol esterified with multi-methyl branched fatty acids (mycocerosic acids) (Daffk and LanCelle, 1988). There are minor variations in the fatty acids and the phenolphthiocerol core between species, but the main differences occur in the nature of the sugar(s) attached to the phenolic hydroxyl. The structure as a whole, and many of the individual sugars found, are apparently unique to a few species of mycobacteria. Information about the biosynthesis of the phenolic glycolipids is limited. The carbon atoms in the methyl-branched structures in mycocerosic acids are derived from propionate (Gastambide-Odier et al., 1963 a;Yano and Kusunose, 1966), as are those in phthiocerol (GastambideOdier et al., 1967;Gastambide-Odier and Sarda, 1970). The aromatic ring can be derived from tyrosine (Gastambide-Odier and Sarda, 1970), though not from phenylalanine. The methoxyl residue in phenolphthiocerol presumably comes from methionine, by analogy with the known source in the related lipid phthiocerol (Gastambide-Odier et al., 1963 b). Rainwater and Kolatukuddy (1982, 1983 strated two steps in the biosynthesis of mycocerosic acids, and isolated the enzymes involved, but the biosynthetic steps leading to phenolphthiocerol itself are not known. Using M. microti, which is a member of the M. tuberculosis group which causes tuberculosis in small rodents but not in humans (Wells, 1946), we have sought potential intermediates in phenolphthiocerol biosynthesis. We report here the identification of two aglycosyl derivatives of mycoside B, which may...

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Possible intermediates in the biosynthesis of mycoside B by Mycobacterium microti

Thurman

Chai²,

Rosankiewicz³

et al. 1993

European Journal of Biochemistry

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“…When the unique distal glycobiose unit N-acylkansosaminyl (1)(2)(3)(4) fucopyranose is added to the growing oligosaccharide chain, then specific anti-M. kansasii antigenicity is conferred. The second class of glycolipids, of the same family as the well-known phenolic glycolipid I of Mycobacterium leprae (18,20), had been known for many years as mycoside A (16). However, its complete structure has only recently been established (10)(11)(12)28) (Fig.…”

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Chemical basis of rough and smooth variation in mycobacteria

1989

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Rough and smooth colony variants of Mycobacterium kansasii were compared with respect to surface glycolipid composition. Thin-layer chromatography of the native glycolipid antigens, gas chromatography of the constituent sugars, and in situ probing with an appropriate monoclonal antibody by colony dot blot enzyme-linked immunosorbent assay and immunogold labeling demonstrated that all M. kansasii strains of smooth colony morphology contain on their surfaces the recently described trehalose-containing lipooligosaccharides, whereas all rough variants were devoid of such surface antigens. Yet all strains, rough and smooth, contained another glycolipid, the M. kansasii-specific phenolic glycolipid. Previous studies by others had shown that the rough forms of M. kansasii persist longer than smooth variants in experimentally infected mice. Therefore, this study may provide some insight into the question of the chemical basis of pathogenesis in certain mycobacteria.

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“…In The aglycon R residue was identified by Gastambide-Odier and co-workers (229,232) as a phthiocerol molecule mainly esterified by mycocerosic FA. Mycobacterium kansasii, the "yellow" bacillus, is an important etiologic agent of chronic pulmonary infections indistinguishable from tuberculosis.…”

Section: Phenolic Glycolipidsmentioning

confidence: 98%

“…These glycolipids attracted great interest at first for the unusual structure of their lipid part, and then as potential tools to detect infections by Mycobacterium tuberculosis. The structure of the lipid aglycone moiety (phenolphthiocerol) was studied by Gastambide-Odier and co-workers (228,229). It is unusual because of its terminal phenol moiety, derived biosynthetically from tyrosine, which bears a long chain with two hydroxyl groups acylated by multimethyl-branched FA.…”

Section: Phenolic Glycolipidsmentioning

confidence: 99%

Astonishing diversity of natural surfactants: 3. Carotenoid glycosides and isoprenoid glycolipids

Dembitsky

2005

Lipids

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Carotenoid glycosides and isoprenoid glycolipids are of great interest, especially for the medicinal, pharmaceutical, food, cosmetic, flavor, and fragrance industries. These biologically active natural surfactants have good prospects for the future chemical preparation of compounds useful as antimicrobial, antibacterial, and antitumor agents, or in industry. More than 300 unusual natural surfactants are described in this review article, including their chemical structures and biological activities.

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Contribution à l'étude de la structure et de la biosynthèse de glycolipides spécifiques isolés de mycobactéries: les mycosides A et B

Cited by 32 publications

References 20 publications

Possible intermediates in the biosynthesis of mycoside B by Mycobacterium microti

Possible intermediates in the biosynthesis of mycoside B by Mycobacterium microti

Chemical basis of rough and smooth variation in mycobacteria

Astonishing diversity of natural surfactants: 3. Carotenoid glycosides and isoprenoid glycolipids

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