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At least 55 records · Page 3Linked to original sources
PubMed1986

Immunoelectron-microscopical labelling of glycolipids in the envelope of a demyelinating brain-derived RNA virus (Semliki Forest) by anti-glycolipid sera.

Immunoelectron-microscopical techniques using gold-labelled antibodies were used to localize the glycolipids ganglioside, glucocerebroside and galactocerebroside, and spike glycoprotein antigens, in the envelope of the RNA virus Semliki Forest which had replicated in mouse brain cell cultures. The demonstration of host cell membrane glycolipid antigens in viruses is discussed in relation to the possibility of an autoimmune reaction to central nervous system cells.

Animals↗
PubMed2002

New modified single chained glycolipids. Part 1: synthesis of deoxy and partially O-methylated glycolipids with or without a sulfur containing spacer.

A way to synthesize neoglycolipids with high yields and anomeric purity is described. Starting point of the synthesis strategy is the glycosylation of allyl alcohol with definite steric orientation. Introduction of the hydrophobic moiety was achieved by photoaddition of n-hexadecanethiol and 3-mercaptopropionic acid followed by amidation with n-hexadecylamine, respectively. In order to investigate the influence of different carbohydrate headgroups in the physicochemical behavior of the general glycolipid, especially the orientation of the alkyl chain, a range of neoglycolipids was synthesized. Beside the differences in the configuration between unfunctionalized glycopyranoses like D-glucose, D-galactose and D-mannose, a number of deoxy and partially O-methylated sugar derivatives was prepared. The divergences concerning the different carbohydrate headgroups and the hydrophobic moiety, respectively, can be compared to relatively simple structured glycolipids with hexadecyl residue and without spacer function.

Glycolipids↗
PubMed1999

Glycolipids from sponges. VII. Simplexides, novel immunosuppressive glycolipids from the Caribbean sponge Plakortis simplex.

The new glycolipids simplexides (1) have been isolated from the marine sponge Plakortis simplex, and their structure determined by spectroscopic data and microgram-scale chemical degradation. Simplexides are composed of long-chain secondary alcohols glycosylated by a disaccharide chain, and represent a new structural kind of glycolipids. Simplexides strongly inhibit proliferation of activated T-cells by a non-cytotoxic mechanism and can be regarded as simple model molecules for designing immunosuppressive drugs.

Animals↗
PubMed2005

Glycolipids from sponges. Part 16.(1) discoside, a rare myo-inositol-containing glycolipid from the caribbean sponge Discodermia dissoluta.

Discoside (1a), a glycolipid composed of 4,6-O-diacylated mannose attached to the 2-hydroxyl group of a myo-inositol unit, was isolated as a mixture of homologues from the marine sponge Discodermia dissoluta. The complete stereostructure of this new glycolipid was solved by interpretation of mass spectrometric and NMR data and CD analysis of degradation products.

Animals↗
PubMed2006

Glycolipids from sponges. Part 17. Clathrosides and isoclathrosides, unique glycolipids from the Caribbean sponge Agelas clathrodes.

Two families of unique glycolipids, clathrosides A-C (2a-4a) and isoclathrosides A-C (5a-7a) were isolated from the Caribbean sponge Agelas clathrodes. Clathrosides and isoclathrosides are glycosides of a very-long-chain alcohol derived from fatty acids, a new class of glycolipids that appears to be characteristic of marine sponges. The six compounds differ in configuration and in the branching of alkyl chains. Stereostructures of the clathrosides were determined by NMR and CD spectroscopy, mass spectrometry, and chemical degradation. Location of the methyl branch on the proper alkyl chain required an exceptional 1-D TOCSY experiment, in which coherence was transferred through as many as 13 vicinal couplings.

Agelas↗
PubMed1990

Glycolipid precursors for the membrane anchor of Trypanosoma brucei variant surface glycoproteins. II. Lipid structures of phosphatidylinositol-specific phospholipase C sensitive and resistant glycolipids.

A common diagnostic feature of glycosylinositol phospholipid (GPI)-anchored proteins is their release from the membrane by a phosphatidylinositol-specific phospholipase C (PI-PLC). However, some GPI-anchored proteins are resistant to this enzyme. The best characterized example of this subclass is the human erythrocyte acetylcholinesterase, where the structural basis of PI-PLC resistance has been shown to be the acylation of an inositol hydroxyl group(s) (Roberts, W. L., Myher, J. J., Kuksis, A., Low, M. G., and Rosenberry, T. L. (1988) J. Biol. Chem. 263, 18766-18775). Both PI-PLC-sensitive and resistant GPI-anchor precursors (P2 and P3, respectively) have been found in Trypanosoma brucei, where the major surface glycoprotein is anchored by a PI-PLC-sensitive glycolipid anchor. The accompanying paper (Mayor, S., Menon, A. K., Cross, G. A. M., Ferguson, M. A. J., Dwek, R. A., and Rademacher, T. W. (1990) J. Biol. Chem. 265, 6164-6173) shows that P2 and P3 have identical glycans, indistinguishable from the common core glycan found on all the characterized GPI protein anchors. This paper shows that the single difference between P2 and P3, and the basis for the PI-PLC insusceptibility of P3, is a fatty acid, ester-linked to the inositol residue in P3. The inositol-linked fatty acid can be removed by treatment with mild base to restore PI-PLC sensitivity. Biosynthetic labeling experiments with [3H]palmitic acid and [3H]myristic acid show that [3H]palmitic acid specifically labels the inositol residue in P3 while [3H]myristic acid labels the diacylglycerol portion. Possible models to account for the simultaneous presence of PI-PLC-resistant and sensitive glycolipids are discussed in the context of available information on the biosynthesis of GPI-anchors.

Animals↗
PubMed1973

Glycolipids of peripheral nerve: isolation and characterization of glycolipids from rabbit sciatic nerve.

Besides cerebreside and sulfatide four other glycolipids were isolated from rabbit sciatic nerve and analyzed by chemical and chromatographic methods. Three of the glycolipids were shown to be fatty acid esters of cerebroside; the fourth was characterized as diacyl glycerol galactoside and its alkyl ether analog. In the ester linkage mainly unsubstituted acids with chain length C(16) to C(18) were present. Both hydroxy and unsubstituted acids were found in amide linkage. They varied in chain length from C(16) to C(24) and were typical of cerebrosides. The long-chain base fraction contained sphingosine and dihydrosphingosine as the main components.

Animals↗
PubMed1978

Structural studies on glycolipid of shellfish. II. Occurrence of 3-O-methylgalactosamine in oyster glycolipid.

3-O-Methyl hexosamine was found for the first time and characterized as one of the sugar components of oyster glycolipid. The alditol acetate of this sugar was identified as 3-O-methyl-N-acetylgalactosaminitol acetate by comparing its retention time on gas chromatography and mass spectrum with those of the authentic sample synthesized in this laboratory. The new sugar, 3-O-methylgalactosamine, occupied the non-reducing terminal position of the carbohydrate moiety of the lipid and was linked to the penultimate hexose by a (1 leads to 3) bond.

Animals↗
PubMed1992

Temporal expression of HNK-1-reactive sulfoglucuronyl glycolipid in cultured quail trunk neural crest cells: comparison with other developmentally regulated glycolipids.

Monoclonal antibody HNK-1 is an important marker for embryonic neural crest cells and some of their differentiated derivatives. We have identified 3-sulfoglucuronylneolactotetraosylceramide (SGGL-1) as one of the HNK-1 antigens present in cultures of trunk neural crest cells. This lipid was present at 2 days in vitro and increased in amount with time in culture. Other major HNK-1-reactive antigens present in the culture were glycoproteins of apparent molecular masses of 120, 180, and 200 kDa. The 180- and 200-kDa bands were present at 2, 7, and 17 days in vitro, whereas the 120-kDa band was present only at 17 days in vitro. Gangliosides GD3, LD1, and LM1 were also found in the cultures and exhibited distinct temporal patterns of expression. Ganglioside GD3 was present at all stages examined and its expression peaked at 7 days in vitro. In contrast, LD1 was present only at 2 days in vitro and was not detectable at later times. Ganglioside LM1 increased in amount with time in culture in a pattern similar to that seen for SGGL-1. Taken together, these results indicate that several HNK-1-reactive molecules are expressed in neural crest cultures in a temporally regulated manner along with several glycolipids that do not bear this epitope.

Animals↗
PubMed1985

Protein-glycolipid interactions during spermatogenesis. Binding of specific germ cell proteins to sulfatoxygalactosylacylalkylglycerol, the major glycolipid of mammalian male germ cells.

Specific binding of membrane proteins extracted from rat spermatogenic cells to the major glycolipid of the male germ cell has been demonstrated by affinity chromatography. A new method for the production of affinity matrices, using photoactivatable heterobifunctional cross-linking agents, has been used to immobilize sulfatoxygalactosylacylalkylglycerol. Three proteins of apparent molecular weights 68 000, 34 000, and 24 000 from spermatogenic cells have been shown to selectively and reversibly bind to this affinity matrix. Antiserum raised against the major of these species (68 000) was demonstrated to be specific for this protein by immunoblotting. A new technique for the reduction of background nonspecific antibody staining using this method is described. The immune serum has been used to localize the antigen in frozen testicular sections. The protein is present in the plasma membranes of all germ cells, but the expression is elevated for testicular spermatozoa and cells in or near the basal compartment of the seminiferous epithelium. The relevance of these findings to intercellular communication and spermatogenesis is discussed.

Animals↗
PubMed2006

The liganding of glycolipid transfer protein is controlled by glycolipid acyl structure.

Glycosphingolipids (GSLs) play major roles in cellular growth and development. Mammalian glycolipid transfer proteins (GLTPs) are potential regulators of cell processes mediated by GSLs and display a unique architecture among lipid binding/transfer proteins. The GLTP fold represents a novel membrane targeting/interaction domain among peripheral proteins. Here we report crystal structures of human GLTP bound to GSLs of diverse acyl chain length, unsaturation, and sugar composition. Structural comparisons show a highly conserved anchoring of galactosyl- and lactosyl-amide headgroups by the GLTP recognition center. By contrast, acyl chain chemical structure and occupancy of the hydrophobic tunnel dictate partitioning between sphingosine-in and newly-observed sphingosine-out ligand-binding modes. The structural insights, combined with computed interaction propensity distributions, suggest a concerted sequence of events mediated by GLTP conformational changes during GSL transfer to and/or from membranes, as well as during GSL presentation and/or transfer to other proteins.

Base Sequence↗
PubMed1990

Sequential monitoring of leprosy patients with serum antibody levels to phenolic glycolipid-I, a synthetic analog of phenolic glycolipid-I, and mycobacterial lipoarabinomannan.

Sequential serum samples from leprosy patients at various stages of antibacterial treatment were tested by an ELISA for antibodies to phenolic glycolipid I (PGL-I), a synthetic PGL-I analog (ND-BSA), and lipoarabinomannan (LAM) from Mycobacterium tuberculosis to determine if these antibodies could be useful in monitoring response to therapy. Among patients with positive initial anti-PGL-I IgM, a significant decrease in this antibody was seen over time (p less than 0.01), whether assayed by PGL-I or ND-BSA. The two antigens showed good agreement in the detection of decrease in anti-PGL-I IgM. The greatest decrease was seen in patients with a high initial anti-PGL-I IgM and a high bacterial index (BI). Patients with a declining BI were seen to have generally declining antibody levels to PGL-I and to LAM; in those patients with a fluctuating BI, antibody levels were less predictable. We conclude that antibodies to PGL-I and LAM can be useful in following response to therapy in leprosy patients and that either the native PGL-I or ND-BSA can serve as antigen for the ELISA.

Antibodies, Bacterial↗
PubMed1988

Direct analysis of glycolipids on thin-layer plates by matrix-assisted secondary ion mass spectrometry: application for glycolipid storage disorders.

The lipids accumulated in organs of patients with Gaucher's, Tay-Sachs, and Fabry's disease were identified by means of the combination of thin-layer chromatography and matrix-assisted secondary ion mass spectrometry. The total lipid extract of each lipidosis tissue was chromatographed on a TLC plate and then analyzed directly by mass spectrometry without elution of the sample from the TLC plate. The amount of material needed to obtain an adequate spectrum is in the order of a few micrograms of lipids per band for both positive and negative ion detection. By scanning the plates, mass spectral and chromatographic information can be obtained simultaneously, which was shown to be useful for the qualitative identification of the components on the plates.

Chromatography, Thin Layer↗