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PubMed1976

Rat intestinal glycolipids. II. Distribution and biosynthesis of glycolipids and ceramide in villus and crypt cells.

Intestinal epithelial cells were isolated from rat intestine and grouped into villus and crypt cell fractions. Glycolipids were purified from each cell fraction and quantitated by fluorimetric determination of glycolipid sphingosine. Significant quantities of ceramide were found in all cell fractions and accounted for approximately 15% of total glycolipid sphingosine. While villus and crypt cell fractions quantitatively contained differing amounts of sphingosine, all cell fractions contained proportionally similar quantities of sphingosine when compared to cellular cholesterol or phospholipid. Individual glycolipids, however, showed significant differences in distribution between villus and crypt cells. Hematoside and glucosylceramide were proportionally increased in villus cells, while crypt cells showed an increase in trihexosylceramide and ceramide content. The rate of UDPglucose : hydroxy fatty acid ceramide glucosyltransferase was higher in villus cells while the rate of UDPgalactose : lactosylceramide galactosyltransferase was 3--4 times increased in crypt cells. These studies demonstrate that significant differences in both the distribution and biosynthesis of individual glycolipids occur in crypt and villus cells of rat intestine and are of possible importance in the process of intestinal cell differentiation.

Animals↗
PubMed1985

Macrophage glycolipid receptors for human migration inhibitory factor (MIF): differentiated HL-60 cells exhibit MIF responsiveness and express surface glycolipids which both bind MIF and convert nonresponsive cells to responsiveness.

The human promyelocytic leukemia line HL-60 when treated with a phorbol diester (TPA) differentiates into cells (HL60-TPA) that respond to human migration inhibitory factor (MIF). Unresponsive HL-60 cells became responsive to MIF when preincubated with a glycolipid-enriched preparation extracted from HL60-TPA cells, human monocytes, human macrophage-like (U937) cell line, or with the purified glycolipid receptor for MIF from guinea pig peritoneal macrophages. Human blood monocytes exhibited an increased response to MIF when preincubated with glycolipids from HL60-TPA and U937 cells but not from HL-60 cells. Finally, glycolipids from HL60-TPA cells but not from HL-60 cells were able to reversibly bind MIF when covalently coupled to agarose. These studies suggest that TPA induces the differentiation of HL-60 cells into MIF-responsive cells through the expression of a glycolipid receptor for MIF.

Cell Differentiation↗
PubMed1984

Glycolipids of the mouse peritoneal macrophage. Alterations in amount and surface exposure of specific glycolipid species occur in response to inflammation and tumoricidal activation.

We have characterized the major glycolipid constituents of the mouse peritoneal macrophage, and have demonstrated that alterations in the amount and in the accessibility of specific glycolipid species to galactose oxidase/NaB3H4 labeling, an indicator of glycolipid surface exposure, occur in response to inflammation and as a consequence of activation to a tumoricidal state. The key findings are: (a) Asialo GM1, a major neutral glycolipid constituent of all macrophage populations examined, is accessible to galactose oxidase/NaB3H4 labeling on the surface of TG-elicited and BCG-activated macrophages but not on resident macrophages; (b) GM1 is the predominant ganglioside constituent of the mouse macrophage. Resident macrophages contain two distinct GM1 species, as determined by cholera toxin binding, while TG-elicited and BCG-activated macrophages contain an additional GM1 species. Differences in the relative amounts of these GM1 species, as well as in their accessibility to galactose oxidase/NaB3H4 labeling, exist among the macrophage populations. These observations suggest that both a chemical and spatial reorganization of surface glycolipids occurs in response to inflammation and tumoricidal activation.

Animals↗
PubMed1986

Quantitation of the phenolic glycolipid of Mycobacterium leprae and relevance to glycolipid antigenemia in leprosy.

Chemical and immunologic procedures have been developed for quantitation, in the body fluids of patients with leprosy, of phenolic glycolipid I, the major specific antigen of the leprosy bacillus. Serum samples were extracted with CHCl3/CH3OH and fractionated on columns of silicic acid. Thin-layer chromatography with a sensitivity of about 500 ng allowed detection of the glycolipid in untreated lepromatous and borderline patients, and high-pressure liquid chromatography gave a quantitation of 0.8-3.7 micrograms/ml of serum from four patients. An ELISA-inhibition assay with polyclonal antibodies to glycolipid corroborated these figures. Dot-ELISA on nitrocellulose with polyclonal and monoclonal IgG antibodies allowed for much greater sensitivity (500 pg) and semiquantitative evaluation. Small quantities of glycolipid were present in the urine of patients with lepromatous leprosy. In sera obtained from patients undergoing chemotherapy, the amount of glycolipid declined sooner than did titer of antibody. This experimental approach is applicable to diagnosis of leprosy, bacillary quantification, and standardization of skin-test reagents and vaccines.

Animals↗
PubMed1981

Structural studies on glycolipid of shellfish. III. Novel glycolipids from Turbo cornutus.

Five kinds of sphingoglycolipids were isolated from Turbo cornutus. Four of them were a series of novel glycolipids consisting only of galactose. The structures of these glycolipids were studied by methylation analysis, periodate oxidation, enzymatic degradation, and proton magnetic resonance spectroscopy. Three glycolipids were characterized as galactosyl(beta 1 leads to 1)ceramide, galactosyl(beta 1 leads to 6)galactosyl(beta 1 leads to 1)ceramide, and galactosyl(beta 1 leads to 6)galactosyl(beta 1 leads to 6)galactosyl(beta 1 leads to 1)ceramide. Data indicating that the 4th glycolipid might be the tetragalactosyl derivative of this series were obtained. The carbohydrate moiety of the 5th glycolipid, in contrast, was composed of fucose, galactose, glucose and N-acetylglycosamine in a molar ratio of 1 : 2 : 1 : 1.

Carbohydrates↗
PubMed1996

Determination of the structure of a novel glycolipid from Thermus aquaticus 15004 and demonstration that hydroxy fatty acids are amide linked to glycolipids in Thermus spp.

The compositions of the major glycolipids (GL-1) of five strains of Thermus aquaticus, the type strain of T. filiformis, T. oshimai SPS-11, and Thermnus sp. strain CG-2 were examined by gas chromatography, gas chromatography-mass spectroscopy, fast atom bombardment-mass spectroscopy, and chemical methods. The results showed that, with the exception of T. aquaticus 15004, the organisms each have a major glycolipid whose structure was established as diglycosyl-(N-acyl)glycosaminyl-glycosyl diacylglycerol. Glucosamine was present in GL-1 of T. oshimai SPS-11 and Thermus sp. strain CG-2, while galactosamine was present in the GL-1 of T. aquaticus and T. filiformis. The novel major glycolipid of T. aquaticus 15004 was identified as galactofuranosyl-(N-acetyl)galactosaminyl-(N-acyl)galactosaminyl-gluc - osyl diacylglycerol. The hydroxy fatty acids found in the T. aquaticus strains and in the type strain of T. filiformis were exclusively amide linked to the galactosamine of the major glycolipid. Ester-linked hydroxy fatty acids were not detected in the diacylglycerol moiety of GL-1 of these organisms. Hydroxy fatty acids were detected neither in the major glycolipid of T. oshimai SPS-11 and Thermnus sp. strain CG-2, in which glucosamine is present, nor in the major phospholipid of any of the strains examined.

Amides↗
PubMed1985

Isolation of the Mycobacterium leprae-specific glycolipid antigen, phenolic glycolipid-I, from formalin-fixed human lepromatous liver.

A Mycobacterium leprae-specific phenolic glycolipid antigen was purified from Formalin-fixed liver preserved from an advanced lepromatous leprosy patient. Its chemical and immunological properties were compared with those of phenolic glycolipid-I obtained from M. leprae-infected armadillo liver. Based on the findings that the glycolipids from the two sources have the same thin-layer chromatographic properties, infrared absorption spectrum, sugar composition, and seroreactivity, we conclude that large quantities of the phenolic glycolipid-I antigen are produced in human lepromatous leprosy lesions and that Formalin-fixed lepromatous livers and spleens from the prechemotherapeutic era are suitable sources of the glycolipid.

Animals↗
PubMed1992

A family of glycolipids from Toxoplasma gondii. Identification of candidate glycolipid precursor(s) for Toxoplasma gondii glycosylphosphatidylinositol membrane anchors.

Four major glycolipids were extracted from Toxoplasma gondii tachyzoites which were metabolically labeled with tritiated glucosamine, mannose, palmitic and myristic acid, ethanolamine, and inositol. Judging from their sensitivity to a set of enzymatic and chemical tests, these glycolipids share the following properties with the glycolipid moiety of the glycosylphosphatidylinositol anchor (GPI anchor) of the major surface protein, P30, of T. gondii: 1) a nonacetylated glucosamine-inositol phosphate linkage; 2) sensitivity toward phosphatidylinositol-specific phospholipase C and nitrous acid; 3) identity of HF-dephosphorylated GPI glycan backbone between three glycolipids and the HF-dephosphorylated core glycan of the GPI anchor of the major surface protein P30; 4) the presence of a linear core glycan structure blocked by an ethanolamine phosphate residue(s). Taken together with the nature of radiolabeled precursors incorporated into these glycolipids, the data indicate that these GPIs are involved in the biosynthesis of the GPI-membrane anchors of T. gondii.

Animals↗
PubMed1990

Glycolipid composition of a mutant cell line of mouse FM3A cells, and the effect of exogenous glycolipids on cell growth.

Had-1 isolated from mouse mammary tumour FM3A cells as a non-permissive cell line to Newcastle disease virus infection is deficient in NDV receptors, and galactosylation of the complex type sugar chains of the glycoproteins is extensively reduced compared to FM3A cells. It is also deficient in UDP-galactose transport into Golgi vesicles. The major neutral glycolipids in FM3A is Lac-Cer, whereas, in Had-1 cell, Glc-Cer is the major glycolipid and the concentration of neutral glycolipids is one-tenth as low as that in FM3A. GM3, GD3 and sialyl i- and I-type lactosaminylceramide are the gangliosides present in both FM3A and Had-1, although their presence in both cells is only in traces. Had-1 contains relatively high N-glycolyl-neuraminic acid. Among the several glycolipids tested, Lac-Cer, Gg-4-Cer and Glc-Cer showed inhibitory effect on proliferation of Had-1 cells, but did not show any appreciable effect on that of FM3A cells. Lac-Cer had the most potent inhibitory effect and this inhibitory effect was completely reversible. While mice injected with 5 x 10(6) cells of FM3A died in one month, those injected of Had-1 cells at the same dose survived for more than 6 months. Thus glycolipids on the cell surface play an essential role during cell growth both in vivo and in vitro.

Animals↗
PubMed1975

Main structures of the Forssman glycolipid hapten and a Leb-like glycolipid of dog small intestine, as revealed by mass spectrometry. Difference in ceramide structure related to tissue localization.

Two glycolipids of dog small intestine, one with Forssman activity and one with Leb-like activity, have been characterized by mass spectrometry of methylated, and methylated and reduced (LiAlH4) derivatives. The Forssman glycolipid was conclusively shown to be a pentaglycosylceramide with the carbohydrate sequence hexosamine-hexosamine-hexose-hexose-hexose-ceramide, and with sphingosine (dihydroxy base) as major long-chain base and normal fatty acids as the only fatty acids. The Leb-like glycolipid was a hexaglycosyl-ceramide with sequence fucose-hexose-[fucose-] hexosamine-hexose-hexose-ceramide and with phytosphingosine (trihydroxy base) as major long-chain base and only 2-hydroxy fatty acids as fatty acids. The difference of two hydroxy groups in the ceramide between the two glycolipids may be related to a different tissue localization. As shown by immunofluorescense study the Forssman activity was associated with the lamina propria and the Leb-like activity to the glandular epithelium of dog small intestine.

Aluminum↗
PubMed2005

Pentaerythritol as the core of multivalent glycolipids: synthesis of a glycolipid with three SO3Lea ligands.

A glycolipid containing three SO(3)Le(a) ligands was synthesized with pentaerythritol as the core. The glycolipid was used to prepare glycoliposomes that showed stability similar to that of DSPC liposomes without glycolipid. The easily prepared derivatives of pentaerythritol proved to be useful scaffolds for multivalent displaying of carbohydrates in the form of glycolipids and clustered glycoliposomes. [structure: see text]

Carbohydrate Sequence↗
PubMed1993

Differentiation antigens of human germ cell tumours: distribution of carbohydrate epitopes on glycolipids and glycoproteins analyzed using PDMP, an inhibitor of glycolipid synthesis.

Human and mouse embryonal carcinoma (EC) cells are characterized by their expression of cell surface carbohydrate antigens, present in both glycolipids and glycoproteins. These antigens disappear upon differentiation and are replaced with other antigens. We have used the inhibitor of glucosyl ceramide synthetase, 1-phenyl-2-decanoylamino-3-morpholino-1-propanol (PDMP), to study the distribution of carbohydrate epitopes between glycolipids and glycoproteins. PDMP inhibited the expression of glycolipid antigens, but not glycoprotein antigens assayed by immunofluorescence and thin layer chromatography. In the case of SSEA1, we observed expression on both glycolipids and glycoproteins. Resistance to PDMP inhibition suggests that glycoproteins carry the immunodominant form of SSEA1 on the cell surface of differentiated human EC cells and undifferentiated murine EC cells.

Animals↗
PubMed1992

An investigation into the glycolipid metabolism of alpha-N-acetylgalactosaminidase-deficient fibroblasts using native and artificial glycolipids.

Deficient activity of lysosomal alpha-N-acetylgalactosaminidase represents a recently recognized lysosomal disorder whose neurologic manifestation in infancy is infantile neuroaxonal dystrophy. The lysosomal enzyme defect, inherited as an autosomal recessive trait, was first identified in the two brothers, GD and BD. Metabolic modification of glycolipids with terminal alpha-GalNAc was studied in fibroblasts from these patients. [Ceramide-3H]Forssman-glycosphingolipid (GSL), the fluorescent C6-NBD-lyso-Forssman-glycolipid (GL) and a 14C-labelled neoglycolipid containing the blood group A trisaccharide were synthesized and used as probes in degradation studies with cell homogenates and with cells in culture. Assays of each of these substrates with fibroblast homogenates of the patients demonstrated the profound deficiency of alpha-N-acetylgalactosaminidase activity compared with controls. Residual activities in the patients' fibroblast homogenates were detected with all glycolipid substrates; those amounted to 6.3 +/- 3.7% (BD) and 12.8 +/- 6.3% (GD) of the mean activity in controls for [3H]Forssman-GSL, and to 2.2 +/- 0.8% (BD) and 3.6 +/- 1.8% (GD) for C6-NBD-lyso-Forssman GL, respectively. alpha-N-Acetylgalactosaminidase deficiency in intact cells was confirmed by TLC analyses, which showed impaired glycolipid modification in cell extracts obtained following addition of [3H]Forssman GSL and C6-NBD-lyso-Forssman GL to the culture media of fibroblasts from the patients.

Carbohydrate Sequence↗
PubMed1990

Role of glycolipids in the metastatic process: characteristics of neutral glycolipids in clones with different metastatic potentials isolated from a murine fibrosarcoma cell line.

We investigated whether metastatic phenotype is associated with a characteristic glycolipid pattern. For this study, we developed a system of variants with different metastatic potentials that we isolated from the highly metastatic T3 murine fibrosarcoma line by culture in 0.3% agar or on plastic. The glycolipid profiles of T3 cells and of their highly metastatic isolates were characterized by a high level of globotriaosylceramide (Gb3ose). On the other hand, Gb3ose was reduced in a weakly metastatic clone isolated from T3 cells. A reduced level of Gb3ose was also found in a weakly metastatic subclone isolated from a highly metastatic T3 clone. Propagation of this subclone led to the emergence of a series of variants which expressed a high metastatic potential together with a high Gb3ose level. We also observed that Gb3ose was 10 times more prevalent on the cell surface in T3 cells than in a weakly metastatic clone. On the whole, these findings indicate that, in our system of metastatic cells, a high Gb3ose level correlates with metastatic phenotype. It is possible that the highly exposed Gb3ose in metastatic cells is relevant to the metastatic process in view of the role played by the unique molecular structure of this glycolipid in other models of cell-to-cell interaction.

Animals↗
PubMedDate not supplied

Glycolipids from Paracoccidioides brasiliensis. Isolation of a galactofuranose-containing glycolipid reactive with sera of patients with paracoccidioidomycosis.

In the present study, we describe the isolation of glycolipids from yeast and mycelium forms of Paracoccidioides brasiliensis. Both forms contains glucosylceramide as the only neutral glycosphingolipid and two acidic glycolipids termed band 1 and band 2. Band 1 was found to be reactive with 100% of sera of patients with paracoccidioidomycosis tested. Structural analysis of band 1 revealed that it is composed of mannose and galactose in molar ratios of 2:1, and a trace amount of glucose. Furthermore, this paper presents evidence that the galactose unit of band 1 is in the furanose configuration. Finally, it was found that reactivity of paracoccidioidomycosis sera with band 1 glycolipid can be attributed mainly to antibodies directed to galactofuranosyl residue present in this glycoconjugate.

Antibodies, Fungal↗
PubMed1983

Decreased glycolipid antigen expression in lymphoma cell variants escaping from anti-glycolipid serotherapy.

Mice challenged with L5178Y lymphoma cells expression high levels of the glycolipid asialo GM2 (gangliotriosylceramide) were protected from tumor growth by passive administration of a monoclonal antibody specific for the glycolipid; in a few antibody-treated mice, ascites cells eventually proliferated which contained a reduced chemical quantity of the glycolipid antigen (3). We now report that the cells emerging from antibody-treated mice had abnormal marker chromosomes identical to those in the cells used for challenge, indicating that the emergent cells were progeny of the challenge inoculum. Flow cytometric analysis revealed that asialo GM2 was undetectable on the surface of greater than 95% of the tumor cells from antibody-treated mice, whereas surface display of H-2 determinants was unchanged from that of the cells used for challenge. Tumor cells arising in challenged but untreated mice consisted of a mixture of asialo GM2-positive and -negative cells, indicating the presence of selective pressures in these mice as well. None of the cells taken from tumor bearing mice differed significantly from the challenge cells in their susceptibility to natural killer cell attack, suggesting that resistance to natural killer cell lysis was not responsible for the proliferation of these cells in vivo. When cells derived from an antibody-treated mouse were used to challenge mice, serotherapy with anti-asialo GM2 had no effect on mouse survival. These results suggest that serotherapy may complement a host anti-tumor response, from which only asialo GM2 deficient cells can escape.

Animals↗
PubMed1994

Lipid modulation of glycolipid receptor function. Availability of Gal(alpha 1-4)Gal disaccharide for verotoxin binding in natural and synthetic glycolipids.

Verotoxins bind to glycosphingolipids containing terminal Gal(alpha 1-4)Gal residues. Globotriaosylceramide is the most effective receptor for verotoxin-1 in vitro and is the functional plasma-membrane receptor which mediates cytopathology for most sensitive cells. Binding of verotoxin-1 to a series of galabiose-containing or globotriaose-containing synthetic glycolipids with monoalkylsulfides and bisalkylsulfides or sulfones as the lipid moiety, have been studied for toxin binding by TLC overlay and in solid phase in the presence of auxiliary lipids. The results demonstrate that for an identical carbohydrate, binding is dramatically altered according to the nature of the lipid moiety. The close proximity of the galabiose sequence and the hydrophobic species also compromised recognition. The lipid environment is also a major determinant of receptor function, since species that were effective, even preferred toxin receptors as monitored by TLC overlay, were not necessarily recognized in the presence of auxiliary lipids. Certain glycolipids, which were not recognized by TLC overlay, were nevertheless found to be effective receptors in an auxiliary lipid matrix. These results demonstrate the crucial role of the lipid moiety in verotoxin/glycolipid recognition and are discussed in relation to toxin pathogenesis and glycolipid receptor function.

Bacterial Toxins↗
PubMed1986

Glycolipid transfer protein from pig brain transfers glycolipids with beta-linked sugars but not with alpha-linked sugars at the sugar-lipid linkage.

The glycolipid transfer protein purified from pig brain facilitates the transfer of various glycosphingolipids and glyceroglycolipids (Yamada, K., Abe, A. and Sasaki, T. (1985) J. Biol. Chem. 260, 4615-4621). In this paper, the transfer of Man beta 1----4Glc beta 1-Cer and Man alpha 1----4Man beta 1-Cer isolated from a bivalve, Corbicula japonica, the transfer of 3-[Glc alpha 1-]-sn-1,2-diacylglycerol and 3-[Glc alpha 1----2Glc alpha 1-]-sn-1,2-diacylglycerol prepared from Streptococcus lactis, and the transfer of 3-[Glc beta 1-]-rac-1,2-dipalmitylglycerol have been investigated. The transfer of these lipids from liposomes to mitochondria was assayed by the decrease of these lipids in the donor liposomes. These lipids were determined by chromatographic isolation of the lipids, acid hydrolysis of the isolated lipids, and subsequent determination of glucose in the hydrolysate. The glycolipid transfer protein facilitated the transfer of ManGlcCer and ManManGlcCer. The transfer protein did not facilitate the transfer of Glc alpha-diacylglycerol or Glc alpha Glc alpha-diacylglycerol. However, the transfer of Glc beta-dipalmitylglycerol was facilitated by the protein. These results strongly suggest that the glycolipid transfer protein has the specificity to the presence of beta-linked glucose or galactose directly linked to either ceramide or diacylglycerol.

Amino Acid Sequence↗