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PubMed1986

An antigen present in rat adenocarcinoma and normal colon non-epithelial stroma is a novel Forssman-like glycolipid based on isoglobotetraosylceramide.

A glycolipid with blood group A activity detected in the non-epithelial stroma of normal rat colon but not in epithelial cells (Hansson, G.C., Karlsson, K.-A., and Thurin, J. (1984) Biochim. Biophys. Acta 792, 281-292), was purified to homogeneity from normal rat colon and rat colon adenocarcinoma. Mass spectrometry and 1H-NMR spectroscopy of the intact permethylated derivative and gas chromatography after degradation revealed the structure GalNAc alpha 1----3GAINAc beta 1----3Gal alpha 1----3Gal beta 1----4Glc beta 1----1Cer, with the predominant ceramide containing sphingosine and non-hydroxylated 24:0 fatty acid. This identifies this glycolipid as a novel Forssman-like glycolipid, which is a tumor-associated antigen by definition, since it is not present in the normal rat large intestinal epithelium cells but in rat adenocarcinoma derived from these cells.

Acetaminophen↗
PubMed1992

A new glycolipid from Mycobacterium avium--Mycobacterium intracellulare complex.

From a nonpolar lipid fraction of Mycobacterium avium--Mycobacterium intracellulare complex cell mass, a new glycolipid was obtained, which was shown to be 5-mycoloyl-beta-arabinofuranosyl-(1-->2)-5-mycoloyl-alpha-ar abinofuranosyl- (1-->1')-glycerol. When examined by TLC, all the 12 strains of this species tested, including clinical isolates, were found to contain this glycolipid. But the glycolipid was not detected in Mycobacterium bovis BCG or Mycobacterium tubrculosis H37Rv.

Chromatography, Thin Layer↗
PubMed1992

Glycolipids from Thermotoga maritima, a hyperthermophilic microorganism belonging to Bacteria domain.

Two novel glycolipids with a very rare alpha(1-->4) diglucosyl structure have been isolated from the thermophilic bacterium Thermotoga maritima. The structures of these compounds, on the basis of chemical procedures and spectroscopic studies (FAB-MS and NMR), were shown to be: 1(3),2-dipalmitoyl-3(1)-[glucopyranosyl-(6-decanoyl)-alpha-D-(1-->4)- glucopyranosyl-alpha-D]-glycerol (Glycolipid 1) and 1(3),2-dipalmitoyl-3(1)-[glucopyranosyl-alpha-D-(1-->4)-glucopyranosyl- alpha-D]-glycerol (Glycolipid 2).

Chromatography, Gas↗
PubMed1990

Localization of sulfated glucuronyl glycolipids in human dorsal root and sympathetic ganglia.

Sulfated glucuronyl glycolipids (SGGLs) in human dorsal root ganglion (DRG) and sympathetic ganglion (SG) were analyzed biochemically and immunohistochemically. SGGLs were enriched in human DRG (1.02 +/- 0.23 micrograms/mg protein), whereas much lower concentrations of these glycolipids (0.043 +/- 0.23 micrograms/mg protein) were detected in SG. Myelin within DRG and SG was immunostained by anti-SGGL antiserum, although only a few myelinated fibers were seen in SG. Nerve cell bodies or unmyelinated fibers were not immunostained. Subcellular fractionation study of human DRG demonstrated that these glycolipids were not only enriched in myelin but also in the axolemma-enriched fraction. These data are consistent with the view that SGGLs may be expressed on myelinated fibers in myelin and axolemma, suggesting that these compounds may play an important role in regulating myelinogenesis.

Chromatography, High Pressure Liquid↗
PubMed1988

Synthesis and immunoreactivity of neoglycoproteins containing the trisaccharide unit of phenolic glycolipid I of Mycobacterium leprae.

The trisaccharide segment, O-(3,6-di-O-methyl-beta-D-glucopyranosyl)-(1----4)-O-(2,3-di-O-methyl- alpha-L-rhamnopyranosyl)-(1----2)-3-O-methyl-L-rhamnopyranose, of the Mycobacterium leprae-specific phenolic glycolipid I has been synthesized as its 8-(methoxycarbonyl)octyl glycoside and coupled to a carrier protein, to produce a leprosy-specific neoglycoprotein, the so-called natural trisaccharide-octyl-bovine serum albumin (NT-O-BSA). Special features of the synthetic strategy were the use of silver trifluoromethanesulfonate (triflate) to promote glycosylation, resulting in the rhamnobiose in high yield and absolute stereospecificity. The terminal 3,6-di-O-methyl-D-glucopyranosyl group was introduced after O-deallylation of the rhamnobiose. Removal of protecting groups yielded the trisaccharide hapten suitable for coupling to carrier protein. Poly(acrylamide)-gel electrophoresis of the neoglycoprotein demonstrated its purity, and subsequent immunoblotting with a monoclonal antibody directed to the terminal 3,6-di-O-methyl-beta-D-glucopyranosyl epitope of the native glycolipid demonstrated its antigenicity. Comparative serological testing in enzyme-linked immunosorbent assays of NT-O-BSA, the corresponding disaccharide-containing products, and another trisaccharide-containing neoglycoprotein, O-(3,6-di-O-methyl-beta-D-glucopyranosyl)-(1----4)-O-(2,3-di-O- methyl-alpha-L-rhamnopyranosyl)-(1----2)-(3-O-methyl-alpha-L-rhamnopy ran osyl)- (1----4')-oxy-(3-phenylpropanoyl)-BSA (NT-P-BSA) [Fujiwara et al., Agric. Biol. Chem., 51 (1987) 2539-2547] against sera from leprosy patients and control populations showed concordance; the presence of the innermost sugar did not contribute significantly to sensitivity or specificity. The di- and tri-saccharide-containing neoantigens, on account of ready availability and solubility, provide greater flexibility than the native glycolipid for the serodiagnosis of leprosy.

Antigens, Bacterial↗
PubMed1991

The resolution into molecular species on desorption of glycolipids from thin-layer chromatograms, using combined thin-layer chromatography and fast-atom-bombardment mass spectrometry.

Using a specially designed, motorised t.l.c.-f.a.b.-m.s. probe with continuous desorption and scanning over a moving t.l.c. plate, it was shown that glycolipids with identical carbohydrate sequences were well resolved into molecular species with differences in long-chain base and fatty acid. There was no serious diffusion of the glycolipids into the matrix. The technique is demonstrated for sulphatides (one and two sugar residues) isolated from human kidney, GM3 ganglioside isolated from human malignant melanoma, and chemically modified gangliotetraosylceramide from mouse intestine. T.l.c.-f.a.b.m.s. is convenient for sequencing and composition analysis of receptor-active glycolipids, the biological activity of which can be monitored in parallel by overlay on the t.l.c. plate with proteins, viruses, bacteria, or animal cells.

Carbohydrate Sequence↗
PubMed1986

Tumor-associated glycolipid antigens, their metabolism and organization.

A number of experimental animal tumors as well as human cancers have been characterized by dramatic changes of glycolipid composition and metabolism. This review focuses on the chemical and enzymatic basis of the appearance of tumor-associated glycolipid antigens belonging to four major structural classes, i.e., globo, ganglio, lacto type 1, and lacto type 2 series. Some antigens represent the accumulation of precursors with deletion of more complex glycolipids, and others are the result of enhanced synthesis of new structures, most of which are aberrant fucosylation or sialylation or their combination; thus, novel structures such as di- or trimeric Le chi, trifucosyl Le gamma, sialyl Le chi, sialyl dimeric Le chi and disialyl Le alpha A have been isolated and characterized. Many monoclonal antibodies are capable of recognizing antigens in high density but are not capable of reacting with the same antigen in low density. Therefore, the expression of novel structures in high densities at the cell surface is important for recognition of tumor-association antigens. Molecular models of a typical tumor-associated antigen and its organization in membranes are also presented.

Animals↗
PubMed1994

In vivo incorporation of [2-14C]mevalonic acid into rat brain complex glycolipids: characterization of glycosylsterols in mammalian brain.

The in vivo incorporation of [2-14C]mevalonate into complex glycolipids of rat brain was investigated. Results indicated that the majority of the incorporated radioactivity was found to be in cholesterol. Analysis of neutral glycolipid and ganglioside fractions revealed that there were selected radioactive bands co-migrating to known glycolipids and gangliosides and the hydrolysis of which released the radioactive cholesterol. These results indicated the existence of glycosylsterols in the rat central nervous system.

Animals↗
PubMed1983

HPLC analysis of neutral glycolipids: an aid in the diagnosis of lysosomal storage disease.

Concentrations of GL-la (glucocerebroside) (8.36 nmol/ml), GL-2a (lactosylceramide) (4.03 nmol/ml), GL-3a (globotriosylceramide) (2.25 nmol/ml) and GL-4a (globotetraosylceramide) (2.87 nmol/ml) have been determined in normal plasma and compared to concentrations in the plasma from patients with Gaucher, Krabbe, Fabry, Sandhoff and Tay-Sachs diseases as well as with hypercholesterolemia. HPLC analysis of perbenzoylated glycolipid derivatives (isolated and purified by modification of an existing procedure) was performed on samples equivalent to 50 to 100 microliter of plasma. The sensitivity could be readily increased ten-fold. We have employed a novel internal standard-monogalactosyl diglyceride, a plant glycolipid, commercially available in pure form. Analysis was performed on a 5 micron ultrasphere silica column, using a gradient of isopropanol in hexane rather than the more usual dioxane in hexane. Our gradient exhibited an essentially flat baseline precluding the necessity of a reference cell. Recoveries of glycolipids added to plasma (95%), experimental yields (60%) and standard curves are presented and discussed. A method is also presented for the separation of GL-la and monogalactosyl diglyceride derivatives for rapid (8 minute) isocratic analysis of multiple samples from Gaucher patients. The benefits of such a simple, reproducible HPLC technique are discussed.

Chromatography, High Pressure Liquid↗
PubMed1992

Specific binding of phenolic glycolipid antigens from Mycobacterium bovis BCG with antibodies.

We studied the molecular binding specificity of two rabbit polyclonal sera generated against phenolic glycolipid antigens namely PheG1 B and PheG1 B-3 from Mycobacterium bovis BCG. PheG1 B is the well-known mycoside B (2-O-Me-alpha-L-Rhap 1----aglycone), while PheG1 B-3 is a recently found glycolipid (alpha-L-Rhap-(1----3)-2-O-Me-alpha-L-Rhap 1----aglycone). The interaction specificity was mainly explained in terms of the cavity volume of the antibodies paratope. The anti-PheG1 B antibodies paratope fits the 2-O-Me-alpha-L-Rhap ligand, while that of anti-PheG1 B-3 binds the disaccharide moiety of PheG1 B-3, and, with a higher affinity, the monosaccharidic unit localized at the non-reducing end. The B-3 antigen affinity is higher than that of antigen B for their homologous antibodies. This can be explained by the fact that the antibodies against phenolic glycolipid B-3 bind optimally to two sequential glycosyl residues suggesting the presence of two subsites. The immunoglobulin subsite with the major affinity binds the monosaccharidic unit localized at the non-reducing end.

Animals↗
PubMed1988

Polysaccharide and glycolipid composition in Tritrichomonas foetus.

1. The polysaccharide and glycolipid composition in Tritrichomonas foetus was studied by paper, thin-layer and gas-liquid chromatographic analysis. 2. The carbohydrate components of the polysaccharide were glucose (47%), galactose (34%) and mannose (19%). N-acetylneuraminic acid was the sialic acid derivative characterized in the flagellate whole cells. 3. The sialic acid density was estimated as 2.7 x 10(7) residues/cell. 4. The long-chain base dihydrosphingosine, the carbohydrates galactose (67%), glucose (21%) and mannose (12%) as well as the fatty acids myristic (48%) and palmitic (52%) acids were characterized as components of the total glycolipids of T. foetus. 5. Total glycolipids were fractionated: a galactocerebroside and a ganglioside were identified.

Animals↗
PubMed1985

Nitrocellulose-based assays for the detection of glycolipids and other antigens: mechanism of binding to nitrocellulose.

A variety of simple and rapid assays for the detection of glycolipids by direct binding to nitrocellulose or binding to antibody-coated nitrocellulose, and probing with monoclonal antibodies are described. These include dot-blotting, charge shift electrophoresis and electroblotting. It is shown that the direct binding of the Leishmania major glycolipid to nitrocellulose is dependent on its lipid moiety, indicating that the mechanism of binding is probably via hydrophobic interactions. However, the L. major glycolipid from which the lipid moiety has been removed can still be detected by blotting onto nitrocellulose precoated with a monoclonal antibody directed to a carbohydrate epitope. The general approach of blotting onto antibody-coated nitrocellulose thus extends the usefulness of these techniques to cases in which the antigen to be detected does not bind directly to nitrocellulose.

Antigens, Protozoan↗
PubMed1986

Immunological relationship between a demyelinating RNA enveloped budding virus (Semliki Forest) and brain glycolipids.

A monoclonal antibody (MAb) raised against central nervous system (CNS) myelin (212) and a MAb (308) raised against brain with Semliki Forest virus (SFV) were both found to react against the same CNS glycolipids. Both these MAbs were also found to react strongly with SFV and against certain brain glycolipid fractions in an immunosorbent assay (ELISA). This demonstrates the presence of common glycolipid antigens in the viral envelope and CNS myelin. MAb 212 had no SFV neutralising capacity and that of MAb 308 was not significant. However, MAb 212 inhibited the neutralisation of the virus by the MAbs (302, 307) specific to SFV proteins. The implications of these findings in relation to the viral induced CNS autoimmunity and persistence of virus in the CNS is discussed.

Antibodies, Monoclonal↗
PubMed1990

Immunoelectron microscopical labelling of a glycolipid in the envelopes of brain cell-derived budding viruses, Semliki Forest, influenza and measles, using a monoclonal antibody directed chiefly against galactocerebroside resulting from Semliki Forest virus infection.

Neurotropic RNA budding viruses such as Semliki Forest virus (SFV), influenza and measles were each grown in identical mouse brain cell cultures. Positive immunoelectron microscopical labelling with gold was seen in the envelope of these viruses using an anti-SFV derived glycolipid monoclonal antibody (MAb), 373 shown to be directed chiefly against galactocerebroside. The results indicate that each enveloped virus grown from the same cell type contains the same glycolipid in its envelope. The presence of common glycolipids derived from the host cell in the envelopes of various enveloped budding viruses may play a significant role in the pathogenesis of virus induced, immune mediated CNS autoimmunity and demyelination, particularly in multiple sclerosis (MS).

Animals↗
PubMed1994

Pattern of nervous tissue immunostaining by human anti-glycolipid antibodies.

Immunostaining of human, bovine and rodent unfixed nervous tissue sections was performed in order to characterize the structures recognized by anti-glycolipid antibodies. Four human sera from patients, two with M-IgM and motor neuron syndrome or motor neuropathy and two with motor neuropathy and polyclonal IgG antibody activity against gangliosides (GL; i.e. GM1, GD1b, GD1a), were utilized. Serum from a patient with sensory neuropathy and M-IgM immunoglobulins with antibody activity against sulfatide (SUL) was included in this series. This study shows that polyclonal and monoclonal anti-glycolipid antibodies give three different patterns of staining. The first is cholera toxin-like showing a more restricted neuronal pattern of staining. The second is peanut agglutinin-like, which includes the carbohydrate epitope shared by a group of glycoproteins in the gray and white matter. The third (anti-SUL) gives a preferential myelin staining. However, sera with anti-GM1 and anti-SUL antibodies recognize a number of closely situated determinants in the gray matter of the spinal cord and in the granule cells, while in peripheral nerves or in neuronal cells in culture their binding produces a different pattern (nodes of Ranvier for anti-GL; myelin for anti-SUL). These findings indicate that immunohistochemistry with anti-GL and anti-SUL antibodies may provide information regarding the glycolipid-bearing anatomical structures as target antigens and further substantiate the role of these molecules in the pathogenesis of autoimmune neurological disorders.

Amyotrophic Lateral Sclerosis↗
PubMed1988

Isolation, purification and quantification of phenolic glycolipid-1 from human leprosy skin tissues.

Phenolic glycolipid-I, a marker lipid of Mycobacterium leprae, was isolated from skin biopsies obtained from untreated lepromatous leprosy patients by silicic acid and florisil column chromatography and purified by thin layer chromatography. Tissues with varying bacillary loads were analysed for their phenolic glycolipid content. A good correlation was observed between the bacillary population of the tissues and the phenolic glycolipid content.

Antigens, Bacterial↗
PubMed1982

Effect of glycolipids and glycophorin on the activity of human interferon-beta and -gamma.

We have studied neutralization of the antiviral activity of human fibroblast (IFN-beta) and immune interferon (IFN-gamma) by incubation with glycolipids (including the gangliosides GM1, GM2 and GM3, as well as various other glycolipids) and with the sialoglycoprotein, glycophorin. When 100 units/ml of IFN-beta were preincubated with 30-80 microM of the gangliosides, all antiviral activity was abolished. Similarly, 120 microM of glycophorin completely reversed the antiviral activity of 100 units/ml of IFN-beta. Glycolipids containing more than two sugars also showed moderate inhibitory effects. GM2 at a concentration of 200 microM almost completely inhibited the antiviral activity of 100 units/ml of IFN-gamma, but GM1, GM3 and glycophorin had only a moderate inhibitory effect. These results suggest that the terminal N-acetylneuraminic acid (NANA) residues of gangliosides and of glycophorin play an important role in the inhibition of IFN-beta, and that they may be similarly involved in the inhibition of IFN-gamma.

Binding Sites↗
PubMed1994

Stereochemistry of 2,4-dimethyleicos-2-enoate from the pyruvylated glycolipid of Mycobacterium smegmatis.

The absolute stereochemistry of 2,4-dimethyleicos-2-enoic acid, isolated from the pyruvylated glycolipid of Mycobacterium smegmatis, has been determined. The two enantiomers of methyl 2,4-dimethyleicos-2-enoate were synthesised for the first time but could not be separated by gas chromatography on cyclodextrin phases. (E)-2-Methyloctadec-2-enoate, an intermediate in the synthesis, is a characteristic component of acyl trehalose glycolipids from Mycobacterium fortuitum. Ozonolysis of the fatty acid ester mixture, obtained from the pyruvylated glycolipid produced 2-methyloctadecanoate. It was identified as the (S)-enantiomer by comparison with (2R) and (2S)-2-methyloctadecanoic acid, intermediates in the synthesis of (4R)- and (4S)-2,4,-dimethyleicos-2-enoic acid, using enantioselective gas chromatography of the methyl esters with heptakis(2,6-di-O-methyl-3-O-pentyl)-beta-cyclodextrin as a chiral stationary phase. The natural acid was therefore determined to be 2E-(4S)-2,4-dimethyleicos-2-enoic acid.

Fatty Acids, Monounsaturated↗