The occurence of methyl ethers of rhamose and fucose in specific glycolipids of certain mycobacteria

Maclennan, A. P.; Randall, H. M.; Smith, Donald W.

doi:10.1042/bj0800309

Cited by 45 publications

(19 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The percentage of recovery of these amino acids was also low, indicating loss (ether extraction discussed in previous paragraph) or destruction. All other amino acids were present in very nearly the same amounts as in the hydrolysate of whole chlamydospores, except with glutamic acid, 14.3% of which was found in the trichloroacetic acid extract.…”

Section: Fig 3 Fluorescence Of Chlamydospores After Vitalmentioning

confidence: 83%

“…Of course, the lipid content of different yeasts is very variable, ranging from 2.3 to 63% (16), and the amount of lipid produced may depend not only on the organism but also on the composition of the culture medium, pH, and temperature (7). The finding that the free lipid fraction of chlamydospores contains sugars is interesting when compared with work on Mycobacterium tuberculosis (14). Upon subjection of the free lipid fraction of tubercle bacilli to acid hydrolysis, methyl ethers of rhamnose and fucose were found.…”

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Chemical Composition of Chlamydospores of Candida albicans

Jansons

Nickerson

1970

J Bacteriol

View full text Add to dashboard Cite

A variety of analytical techniques was employed to study the composition of the chlamydospore of Candida albicans. The outer, thin, electron-transparent layer was found to be composed of glucan, together with a small amount of chitin. The inner, thick, electron-dense layer is proteinaceous. The central structure is composed largely of ribonucleic acid and lipid globules. In addition to being acid-fast, the chlamydospore was found to contain glycolipids and to lose the property of acidfastness on extraction with ethanol-ether. Skujins et al. (21). Streptomyces species no. 3 (kindly supplied by M. Alexander, Cornell University) was maintained on a medium consisting of a 0.5% suspension of distiller's solubles (Brown, Forman Co., Louisville, Ky.) in distilled water, adjusted to pH 7.6, and solidified with 3% agar (Difco). For enzyme production, the organism was grown in a basal salts liquid medium (21) to which autoclaved, lyophilized cells of C. albicans were added (5 g/liter). This medium (25 liters) was sterilized in a 40-liter fermentor 922 on July 31, 2020 by guest

show abstract

Section: Fig 3 Fluorescence Of Chlamydospores After Vitalmentioning

confidence: 83%

Section: Discussionmentioning

confidence: 99%

Chemical Composition of Chlamydospores of Candida albicans

Jansons

Nickerson

1970

J Bacteriol

View full text Add to dashboard Cite

show abstract

“…It has also been reported in glycolipids from Mycobacterium leprae (8, 23) and other mycobacterial species (18,19,26), as well as in lipopolysaccharides from species belonging to the genera Klebsiella (4), Rhodopseudomonas (21,28), and Azospirillum (6). It is a component of extracellular capsular polysaccharides of rhizobial root nodules of Acacia (9,10,12) and an antitumor antibiotic, calichemicin, a product of the actinomycete Micromonospora echinospora (16,17).…”

Section: Discussionmentioning

confidence: 99%

3-O-Methylrhamnose: Identification and Distribution in Catellatospora Species and Related Actinomycetes

Asano

Sano²,

Masunaga

et al. 1989

International Journal of Systematic Bacteriology

View full text Add to dashboard Cite

3-0-methylrhamnose was found in cell walls of Catellatospora ferruginea. This sugar was purified and identified by proton and 13C nuclear magnetic resonance and mass spectroscopy, using the acetylation method. It is localized in the cell wall fraction and occurs at a constant ratio among the cell wall sugars when various carbon sources are used for growth. 3-0-methylrhamnose was found in nine strains of Catellatosporu species containing MK-10 as the major menaquinone, but not in nine strains containing MK-9. Among 22 type strains of genera related to Catellatospora (Actinoplanes, Amorphosphorangium, Ampullariella, Dactylosporangium, Micromonosporu, Glycomyces, and "Catenuloplanes"), 4 strains contained only trace quantities, and the remainder contained none. Thus, we propose that 3-0-methylrhamnose is a key sugar in the chemotaxonomy of the genes Catellatospora.

show abstract

“…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.…”

mentioning

confidence: 99%

Possible intermediates in the biosynthesis of mycoside B by Mycobacterium microti

Thurman

Chai²,

Rosankiewicz³

et al. 1993

European Journal of Biochemistry

View full text Add to dashboard Cite

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...

show abstract

The occurence of methyl ethers of rhamose and fucose in specific glycolipids of certain mycobacteria

Cited by 45 publications

References 24 publications

Chemical Composition of Chlamydospores of Candida albicans

Chemical Composition of Chlamydospores of Candida albicans

3-O-Methylrhamnose: Identification and Distribution in Catellatospora Species and Related Actinomycetes

Possible intermediates in the biosynthesis of mycoside B by Mycobacterium microti

Contact Info

Product

Resources

About