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PubMed1989

Factors regulating the expression of the neutral glycolipids in the mouse small intestinal mucosa.

GDP-fucose:asialo GM1 alpha(1-2)fucosyltransferase (FT) is induced in the small intestinal mucosa after microbial contamination of germ-free mice (Umesaki, Y., Sakata, T. and Yajima, T. (1982) Biochem. Biophys. Res. Commun. 105, 439-443). As a result, asialo GM1 glycolipid, a major component of the epithelial cell membrane, drastically converted into fucosyl asialo GM1. There were many other examples in which FT was induced. One was the weaning period for conventional mice. Others included injuries of the small intestine by punctures or administration of cytosine arabinoside, and the injection of protein synthesis inhibitors, such as cycloheximide or emetine, or the soluble fraction of the small intestinal homogenate (SISF). The induction of FT was more rapid after injection of cycloheximide or SISF than after injury, mechanical puncturing or after administration of cytosine arabinoside. The changes in the neutral glycolipids of the small intestine by injection of cycloheximide or SISF were analyzed in detail. FT activity started to increase after approx. 5 h and reached the maximum 10-12 h after injection of cycloheximide or SISF, and rapidly declined thereafter. The conversion of asialo GM1 into fucosyl asialo GM1 started after about 10 h and reached the maximal value 24 h after the treatment. Fucosyl asialo GM1 persisted for a few days, although the FT activity fell to near the basal level. On the other hand, the amount of glucosyl ceramide was constant after these treatments. There was little difference in the time-courses of both the FT activity and the glycolipid conversion between these treatments. In the case of co-injection of cycloheximide and SISF, the effect of both materials on FT activity induction was synergistic. The distribution of FT activity and immunohistochemical staining using anti-fucosyl asialo GM1 antibody along the crypt-villus axis showed a stronger expression of fucosyl asialo GM1 in villus portion, the post-mitotic cell zone, than in the crypt portion. Asialo GM1 was converted into fucosyl asialo GM1 after the induction of FT by the various treatments mentioned above. Especially the effects of cycloheximide and/or SISF on FT induction suggest at least the presence of a regulatory protein(s) which controls the glycolipid expression in the small intestine.

Animals↗

PubMed1989

Novel isoglobo-neolacto-series hybrid glycolipid detected by a monoclonal antibody is a rat colon tumor-associated antigen.

Isoglobotetraosylceramide (GalNAc(beta 1-3)Gal(alpha 1-3)Gal(beta 1-4)Glc (beta 1-1)Cer), the major glycolipid species in dimethylhydrazine-induced rat tumors of colorectal origin, was not detected in epithelial cells of normal colon but was present in the non-epithelial stroma and could be extracted from each of nine tumors studied. Monoclonal antibodies produced against isoglobotetraosylceramide detected this and another novel rat tumor-associated glycolipid not present in epithelial cells nor in non-epithelial stroma of normal rat colon (Brodin, T., Thurin, J., Strömberg, N., Karlsson, K.-A. and Sjögren, H.O. (1985) Eur. J. Immunol. 16, 951-956). This novel glycolipid was present in 8/9 of the studied tumors and was also present in two in vitro cell clones. These were originally obtained from a W49/T4 colon tumor isograft. The novel glycolipid was characterized by mass spectrometry, 1H-NMR, and methylation analysis as a hybrid between the isoglobo- and neolacto-series, with the structure GalNAc(beta 1-3)Gal(alpha 1-3)Gal(beta 1-4)GlcNA(beta 1-3)Gal (beta 1-4)Glc(beta 1-1)Cer.

Animals↗

PubMed1990

Characterisation of phenolic glycolipids from Mycobacterium marinum.

The phenolic glycolipids from two strains of Mycobacterium marinum have been isolated and characterised. The glycolipids from M. marinum MNC 170 were principally glycosides of diacyl C37, C39 and C41 phenolphthiocerols A, but in M. marinum MNC 842, these lipids were accompanied by glycosides of diacyl phenolphthiodiolones A and novel phthiotriols A with the same overall chain-lengths. The main acyl components of the phenolic glycolipids from M. marinum MNC 170 were C26 dimethyl and C27 and C29 trimethyl-branched fatty acids, but in the lipids of M. marinum MNC 842, the C27 trimethyl acid was the only principal component. The sugar composition of all these glycolipids had been previously shown to correspond to 3-O-methylrhamnose.

Gas Chromatography-Mass Spectrometry↗

PubMed1995

Sequential changes in glycolipid expression during human B cell differentiation: enzymatic bases.

We have previously reported that human B cell differentiation is accompanied by sequential changes in glycosphingolipid expression. Pre-B cells contain lacto-series type II chain-based glycolipids and GM3 ganglioside; mature/activated B cells do not synthesize lacto-series compounds but express GM3 and globo-series glycolipids (Gb3 and Gb4); terminally differentiated B cells, in addition to these compounds, also contain GM2 ganglioside. At the cell surface, Gb3, Gb4 and GM2 constitute stage-specific antigens. To elucidate the biosynthetic mechanism leading to these modifications we have compared activities of the glycosyltransferases involved in the core structure assembly and the first elongation steps of neo-lacto, ganglio- and globo-series glycolipids. These glycosyltransferase activities have been measured in B cell lines and normal B lymphocytes at various stages of differentiation. We first determined the optimal requirements of the four glycosyltransferases which synthesize Lc3, GM3, Gb4 and GM2 glycolipids in B lymphocytes and then tested these enzymes and the Gb3 synthetase in the selected B cells. The following results were obtained: beta 1-->3 N-Acetylglucosaminyltransferase (Lc3 synthetase) has a high activity in pro- and pre-B cells whereas it is undetectable in more differentiated cells; alpha 2-->3 sialytransferase (GM3 synthetase) is activated from the pre-B cell stage to the terminally differentiated myeloma cells; alpha 1-->4 galactosyltransferase (Gb3 synthetase) is only detected in cells representing the late stages of B cell differentiation; beta 1-->3 N-Acetylgalactosaminyltransferase (Gb4 synthetase) is only found in some lymphoblastoid cell lines, representative of activated B cells whereas the beta 1-->4 N-Acetylgalactosaminyltransferase (GM2 synthetase) has a high activity in these lymphoblastoid cell lines and in terminally differentiated myeloma cells. These results suggest that the sequential shifts in the three major glycosphingolipid series observed during B cell differentiation are mostly due to sequential activations of the corresponding glycosyltransferases.

B-Lymphocytes↗

PubMed1994

Polar lipids of a non-alkaliphilic extremely halophilic archaebacterium strain 172: a novel bis-sulfated glycolipid.

Extremely halophilic archaebacteria which require high salt concentrations for growth and survival contain glycerol diether analogues of phospholipids and sulfated glycolipids as major membrane polar lipids. A non-alkaliphilic, non-pigmented rod-shaped extreme halophile, isolated from sea sand in Japan and designated 'strain 172', was found to contain two phospholipids, phosphatidylglycerol (PG) and phosphatidylglyceromethylphosphate (PGP-Me), derived from both C20-C20- and C20-C25-glycerol diethers, and a novel major glycolipid (designated SGL-X). This glycolipid has been identified as a bis-sulfated diglycosyl C20-C20- or C20-C25-glycerol diether, on the basis of its TLC mobility, positive-staining behavior with sugar and sulfate-staining reagents, its mole ratio sulfate/glycolipid = 2.2, and by spectrometric analysis (IR and FAB-MS) of the intact and the desulfated SGL-X. The sugars were identified as mannose and glucose, after acid hydrolysis of SGL-X, by paper chromatography of the free sugars and GC-MS of the derivatized sugars (alditol acetates). Permethylation analysis and 1H- and 13C-NMR analysis established the position and configuration of the sugar linkages and the positions of the sulfate groups. The final structure of SGL-X (now designated S2-DGD-1) is proposed to be: 2,3-diphytanyl- or phytanyl-sesterterpenyl-1-[2,6-(HSO3)2-alpha-Manp-1--> 2- Glcp]-sn-glycerol. This lipid is the first bis-sulfated glycolipid to be reported in extremely halophilic archaebacteria, and is the first in the biosphere that possesses two sulfate groups attached to the same monosaccaride.

Archaea↗

PubMed1983

Fucosyl-globoside and sialosyl-globoside are new glycolipids isolated from human teratocarcinoma cells.

Several novel glycosphingolipids have been isolated from the human teratocarcinoma cell line HT-E (833K). These cells contain two neutral glycolipids which metabolically incorporate radio-labelled fucose. In addition, there are three new gangliosides present, which are all members of the globoside series of glycolipids. One of the fucose containing glycolipids forms globoside when treated with alpha-fucosidase, and one of the gangliosides forms globoside when treated with neuraminidase. On the basis of chromatographic behavior, exoglycosidase treatment and antibody reactivity, the tentative structures of these new glycolipids are: Fuc (alpha 1-?) GalNAc (beta 1-3) Gal (alpha 1-4) Gal (beta 1-4) Glc (beta 1-Cer) and NeuAc (alpha 2-3) GalNAc (beta 1-3) Gal (alpha 1-4) Gal (beta 1-4) Glc (beta 1-Cer)

Antigens, Neoplasm↗

PubMed1986

Animal glycolipids as attachment sites for microbes.

The abundance of carbohydrate at the animal cell surface may explain why microbes have selected primarily carbohydrates as essential attachment sites for colonization or infection. Of the various surface glycoconjugates of interest, primary attention has been given to glycolipids, due in part to an efficient binding assay based on a thin-layer chromatogram with separated glycolipids. In this way the general character of carbohydrate recognition by microbes is being mapped. Mainly two examples are briefly described to illustrate some generalizations: lactosylceramide-recognition by several bacteria, and Gal alpha l----4Gal-binding by Escherichia coli and the Shiga toxin. The unique recognition of internally placed sequences, the often low-affinity binding, and the preference of certain sequences before others are interpreted to be of decisive biological value. The binding to internal parts makes it technically possible to approximate the binding epitope on a receptor glycolipid. For this the binding preferences to glycolipids carrying the binding site in different saccharide environments (isoreceptors) are compared with the computer-calculated preferred conformations (definition of steric hindrances to epitope access). Several binding epitopes dissected with this approach have a common surface character: a nonpolar area of ring hydrogens over one or two sugars, surrounded by polar oxygens or amide. This is in agreement with the recent Lemieux concept for antibody-carbohydrate interaction. This information facilitates a rational synthesis of receptor analogues for potential applications. An outline is finally given of an improved general approach for receptor analysis.

Animals↗

PubMedDate not supplied

Model membranes bearing glycolipids and glycoproteins.

The forces that hold cell membrane components together are non-covalent and thermodynamically favoured in aqueous media. Hence virtually any glycolipid or membrane glycoprotein might be expected to be incorporable into lipid bilayer membranes and this expectation has been borne out. In addition methods have been developed for linking lipid fragments to species that would not otherwise be expected to associate with bilayers. Techniques that have been successfully used to generate bilayer structures bearing glycolipids and glycoproteins include hydration of films dried down from non-aqueous solutions of the components, detergent removal from aqueous component solutions, exogenous addition to preformed membranes, and various organic solvent injection or reverse phase approaches. Bilayer association of glycolipids and membrane glycoproteins, with preservation of specific receptor function, seem easy to achieve--in fact difficult not to achieve. Optimization of receptor function to accurately mimic that of cell membranes and efficient preservation of functions such as transport or second messenger activation, are typically more demanding, although still feasible. A systematic approach can give considerable insight into the processes involved via identification of minimal necessary factors. Unfortunately, the actual relative arrangement of components, so critical to subtleties of glycolipid and glycoprotein function, remains almost totally unknown for lack of morphological information in the size range of individual macromolecules. The latter problem has come to be the most critical limitation to many studies.

Freeze Etching↗

PubMed1987

Immobilized glycolipids from human diploid fibroblasts inhibit DNA synthesis of cultured human fibroblasts.

Several previous studies have shown that glycolipids isolated from plasma membranes of cultured cells and added to cells in culture inhibit the growth rate in a concentration-dependent fashion. In order to investigate the possible involvement of glycolipids in the growth regulation of normal cells by cell-cell contacts, we tested the effect of immobilized glycolipids, isolated from human fibroblasts, on the DNA synthesis of freshly seeded fibroblasts. Gangliosides inhibited DNA synthesis to a great extent, whereas neutral glycolipids had only a minor effect. The degree of inhibition of DNA synthesis by immobilized gangliosides depended both on the cell density of the cultures from which the gangliosides were isolated and on the pretreatment of the immobilized gangliosides: Preincubation with DMEM without FCS of immobilized gangliosides, isolated from confluent cultures, resulted in a 75% inhibition of growth rate of embryonal human lung fibroblasts (FH109) cultured on immobilized gangliosides. Under the same conditions, gangliosides from sparse cultures reduced the growth rate by about 30%. On the other hand, the degree of inhibition exerted by immobilized gangliosides isolated from confluent cultures was found to be greatly reduced by preincubation with DMEM with FCS, whereas the slight inhibition of growth rate, exerted by gangliosides from sparse cultures, was found to be reversed into a slight stimulation of growth rate after preincubation with complete medium. Concomitantly with the reduction of the inhibition of DNA synthesis, it was found that the complete medium, used for preincubation of the gangliosides, was no longer able to support DNA synthesis to the same extent as untreated complete medium. The data suggest that gangliosides bind growth-supporting factors of the serum, gangliosides isolated from sparse cultures being more potent in the binding of these molecules than gangliosides isolated from dense cultures.

Cell Line↗

PubMed1989

Quantitation of the rabbit intestinal glycolipid receptor for Shiga toxin. Further evidence for the developmental regulation of globotriaosylceramide in microvillus membranes.

Shiga toxin, produced by Shigella dysenteriae 1, causes enterotoxic, cytotoxic, and neurotoxic effects, which may be mediated by a glycolipid receptor, globotriaosylceramide, Gb3. To study the relationship of this receptor and toxin effects, globotriaosylceramide was quantitated and further characterized in rabbit small intestinal microvillus membranes at various ages. Glycolipids were extracted from rabbit microvillus membranes, purified on Unisil columns, and quantitated by high-performance liquid chromatography. The major glycolipid peaks were hydroxylated fatty acid-containing glucosylceramide, lactosylceramide, and globotriaosylceramide. There was a marked increase of globotriaosylceramide levels with age, ranging from 0.02 to 16.2 pmol/micrograms microvillus membrane protein in neonates and adults, respectively. The globotriaosylceramide peak was susceptible to alpha-galactosidase treatment, which produced an elevation in the lactosylceramide peak, but markedly reduced globotriaosylceramide content in 34-day-old rabbits. Binding of iodinated Shiga toxin to globotriaosylceramide was documented on high-performance thin-layer chromatography plates by autoradiography. The glycolipid receptor for Shiga toxin in rabbit microvillus membranes is thus a hydroxylated fatty acid-containing globotriaosylceramide. This moiety is virtually absent in neonates and gradually increases with age. Quantitative differences in globotriaosylceramide may be the underlying basis for the age-specific differences in functional responsiveness of rabbit intestinal tissue to Shiga toxin.

Animals↗

PubMed1993

Isolation, initial characterization and serological studies of glycolipid antigens from Babesia bovis-infected erythrocytes.

Serological analysis of Babesia bovis-derived glycolipids by ELISA and the indirect fluorescent antibody technique demonstrated the existence of their antigenic and immunogenic activities not only in B. bovis but also in B. bigemina infections. This indicates that serological cross-reactivity of B. bovis and B. bigemina relates to glycolipids. The negative ELISA reaction obtained with Anaplasma marginale antisera suggested the specificity of the reaction to the genus Babesia. Fractionation of these glycolipids by Florisil Sep-Pak column chromatography with subsequent HPTLC immunostaining and Orcinol staining suggested the presence of carbohydrate antigenic determinants in B. bovis glycolipids.

Animals↗

PubMed1981

A simple method to measure anti-glycolipid antibody by using complement-mediated immune lysis of fluorescent dye-trapped liposomes.

A simple, reproducible, and micro quantity method is described to measure the antibody against glycolipid antigens. The multilamellar liposomes containing carboxyfluorescein (CF), which is self-quenched at high concentration, are prepared by vortexing the dried lipid films consisting of egg lecithin, cholesterol, phosphatidic acid and Forssman glycolipid antigen. On addition of anti-glycolipid serum plus active complement, liposome lysis occurs, and trapped CF is released. The dilution of CF in the external volume abolishes the quenching, resulting in a high fluorescence signal. Experimental conditions to measure anti-glycolipid antibody is established in this paper.

Animals↗

PubMed1992

Effects of Guillain-Barré sera containing antibodies against glycolipids in cultures of rat Schwann cells and sensory neurons.

Serum samples from 52 patients with the acute Guillain-Barré syndrome (GBS), 19 patients with other neurological disorders, and 18 healthy volunteers were tested for cytotoxicity in cultures of rat Schwann cells and dorsal root ganglion neurons. The samples were also examined by enzyme-linked immunosorbent assay for IgG and IgM antibodies against various acidic and neutral glycolipids. Samples from 16 of the 52 (31%) acute GBS patients and from 1 of the 6 patients with chronic inflammatory demyelinating polyneuropathy produced myelin breakdown in culture. Although 10 of the 16 cytotoxic acute GBS serum samples contained anti-glycolipid immunoglobulins, there was no correlation in individual samples between cytotoxic activity and the presence of antibodies against specific glycolipids. While our results do not exclude a role for anti-glycolipid antibodies in the pathogenesis of the acute GBS, the cytotoxic effects of acute GBS serum in cultures of Schwann cells and sensory neurons are probably not due to these antibodies alone.

Animals↗

PubMed1987

Scrapie prion protein contains a phosphatidylinositol glycolipid.

The scrapie (PrPSc) and cellular (PrPC) prion proteins are encoded by the same gene, and their different properties are thought to arise from posttranslational modifications. We have found a phosphatidylinositol glycolipid on both PrPC and PrP 27-30 (derived from PrPSc by limited proteolysis at the amino terminus). Ethanolamine, myo-inositol, phosphate, and stearic acid were identified as glycolipid components of gel-purified PrP 27-30. PrP 27-30 contains 2.8 moles of ethanolamine per mole. Incubation of PrP 27-30 with a bacterial phosphatidylinositol-specific phospholipase C (PIPLC) releases covalently bound stearic acid, and allows PrP 27-30 to react with antiserum specific for the PIPLC-digested glycolipid linked to the carboxyl terminus of the trypanosomal variant surface glycoprotein. PIPLC catalyzes the release of PrPC from cultured mammalian cells into the medium. These observations indicate that PrPC is anchored to the cell surface by the glycolipid.

Animals↗

PubMed1984

Fine specificity of a monoclonal anti-testicular cell antibody for glycolipids with terminal N-acetyl-D-glucosamine structure.

The specificity of a mouse anti-testicular cell monoclonal antibody, J1, was investigated. Previous studies suggested that N-acetyl-D-glucosamine (GlcNAc) was a constituent of the determinant recognized by J1. When the antibody was tested against a variety of purified glycolipids containing this saccharide in terminal, penultimate or internal positions, J1 reacted only with species expressing terminal GlcNAc. The influence of oligosaccharide chain length, branch substitution, and haptenic valence on J1 binding was examined using glycolipids prepared by a weak acid hydrolysis and exoglycosidase digestion of bovine I-active ganglioside. Degree of binding was inversely proportional to chain length and was proportional to hapten valence. Failure of J1 to bind partially deglycosylated transferrin implied binding preference for GlcNAc beta 1----3Gal over GlcNAc beta 1----2Man. Immunofluorescence analysis of J1 binding to human neutrophils failed to detect lactotriosylceramide on their surface, although this glycolipid has previously been isolated from these cells, suggesting that this structure exists in a cryptic or intracellular form. Binding results were consistent with J1 having low affinity for GlcNAc or GlcNAc beta 1----3Gal on a variety of lacto-series glycolipids.

Acetylglucosamine↗

PubMed1994

A unique neuronal glycolipid defines rostrocaudal compartmentalization in the accessory olfactory system of rats.

A monoclonal antibody, CC6, reacts with a complex glycolipid whose expression in the rat is restricted to the olfactory system. Structural analysis reveals that the glycolipid contains two alpha-fucose branches; one each at internal and external beta-galactose residues. Immunocytochemistry demonstrates in rat embryos that CC6 glycolipid expression is restricted to a subset of neurons in the vomeronasal organ (VNO) and their corresponding axon projections in the caudal accessory olfactory bulb (AOB). This pattern of expression in the accessory olfactory system is the converse of the pattern revealed by a previously characterized antiglycolipid antibody that reacts with VNO neurons projecting to the rostral AOB. The CC6-reactive glycolipid is also expressed on a subset of neurons in the main olfactory epithelium. Postnatally, axons from these CC6 positive sensory neurons converge to form a limited number of axon bundles running longitudinally through the nerve layer of the main olfactory bulb. These data provide further evidence that groups of vomeronasal and olfactory neurons expressing unique surface molecules project axons that terminate in selected targets in the AOB and OB, respectively.

Animals↗

PubMed1996

The Epstein-Barr virus (EBV) alters the B cell glycolipid which is recognized by the human monoclonal antibody to i-blood group antigen.

To analyze the differentiation-related glycolipids, we have recently developed human monoclonal anti-i antibodies (mAbs) using a combination of EBV-transformation and bovine i-active glycolipid (NeuAc alpha 2-->3Gal beta 1-->4GlcNAc beta 1-->3Gal beta 1-->4GlcNAc beta 1-->3Gal beta 1-->4Glc beta 1-->1Cer)-containing liposome immune lysis assay (LILA). Using complement cytolysis with these mAbs, we found the occurrence of a surface antigen (Ag) in the EBV-negative but not in the EBV-positive cell lines. The fresh EBV infection reveals that the suppressed expression of the antigen was a result of the EBV infection. The Ag recognized with these mAbs appeared to have a very low density on the B cell lines. Unexpectedly, thin layer chromatogram (TLC)-immunostaining using the mAbs revealed that the major immunoreactive substance in the EBV-negative B cell lines was an extremely minor glycolipid that was distinct from the i-active glycolipid however, this was not the case in the EBV-positive B cell lines.

Antibodies, Monoclonal↗

PubMed1988

Solubilized glycosyltransferases and biosynthesis in vitro of glycolipids.

The assembly of most of the ceramide-linked glycolipids (GSLs) in eukaryotic cells occurs in Golgi bodies. At least 18 different glycolipid:glycosyltransferases (GSL:GLTs) have been characterized, 10 of which have been solubilized. These GLTs can be classified into 2 distinct groups: 1) GLTs dedicated to either Dol-P-P-sugar(s) or ceramide-linked sugar(s); and 2) GLTs with dual loyalties (i.e., they compete with glycolipid- and glycoprotein-bound oligosaccharides). Studies with solubilized and purified GalNAcT-1 and GalNAcT-2 from embryonic chicken brains prove that GalNAcT-1 (UDP-GalNAc:GM3 beta 1-4GalNAcT) is specific for GSL, whereas GalNAcT-2 (UDP-GalNAc:Gb3 beta 1-3GalNAcT) can transfer to an oligosaccharide containing the alpha-linked terminal galactose. Similarly, GalT-3 (UDP-Gal:GM2 beta 1-3GalT) is more specific for ganglio-oligosaccharide and GalT-4 (UDP-Gal:Lc3 beta 1-4GalT) can transfer galactose to N-acetylglucosamine linked to p-nitrophenol, glycolipid or glycoprotein. Both GalT-3 and GalT-4 have been separated and purified from embryonic chicken brains. Studies with solubilized SAT-4 and SAT-3, from bovine spleen and embryonic chicken brains, respectively, suggest the existence of 2 different gene-expressed alpha 2-3SATs. The newly discovered FucT-3 (GDP-Fuc:NeuGc-iLc6-alpha 1-3FucT) from human colon carcinoma (Colo-205) has also been solubilized and separated from other GSL:GLTs. Using a new activity gel-Western blot combined technique, the molecular mass of this FucT-3 was determined to be 105 kDa.

Animals↗