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PubMed1971

Inhibition of glycolipid biosynthesis in chloroplasts by ozone and sulfhydryl reagents.

The metabolism of uridine 5'-pyrophosphate-galactose by spinach (Spinacia oleracea) chloroplast preparations was inhibited by ozone. The formation of digalactosyl diglyceride and trigalactosyl diglyceride was inhibited much more than the formation of monogalactosyl diglyceride, steryl glycoside, and acylated steryl glycoside. Essentially identical results were obtained when glycolipid synthesis was inhibited by N-ethyl maleimide, p-hydroxymercuribenzoate, and CdCl(2). Iodoacetate and iodoacetamide affected neither the total incorporation of sugar from uridine 5'-pyrophosphate-galactose nor distribution of the incorporated sugar in the various glycolipids.Ozone reacted with model membrane systems prepared with egg lecithin. In the absence of reduced glutathione, products included malonaldehyde and hydrogen peroxide. In the presence of glutathione, malonaldehyde was still produced, but the glutathione was oxidized and no peroxide was detected. When these studies were extended to chloroplast preparations, it was also found that malonaldehyde was produced and glutathione was oxidized.It was concluded that ozone inhibits glycolipid biosynthesis in chloroplast preparations by way of oxidation of enzyme sulfhydryl groups but that this reaction may be a secondary effect of oxidation of unsaturated fatty acids.

Journal Article↗
PubMed2004

Crystallization and X-ray analysis of bovine glycolipid transfer protein.

Glycolipid-transfer protein (GLTP) is a 24 kDa basic cytosolic protein that facilitates the transfer of glycolipids between bilayer membranes in vitro, but its in vivo function is unknown. Human, bovine, porcine and murine GLTPs have recently been cloned and share high sequence identity to each other. The three-dimensional structure of GLTP has not yet been solved and no structures of any proteins related to GLTP are known. Therefore, the structure of GLTP might reveal a currently unknown fold. Here, the crystallization and preliminary X-ray analysis of bovine GLTP are reported for the first time. Protein prepared by recombinant techniques using an Escherichia coli expression system has been crystallized using the vapour-diffusion method. The crystals belong to space group P2(1), with unit-cell parameters a = 55.4, b = 34.9, c = 58.5 A, alpha = gamma = 90, beta = 116 degrees. The crystals diffract to 1.6 A resolution and a 97.1% complete data set with an R(merge) of 6.7% has been collected from a single crystal at 100 K using synchrotron radiation.

Animals↗
PubMed1995

Segmented filamentous bacteria are indigenous intestinal bacteria that activate intraepithelial lymphocytes and induce MHC class II molecules and fucosyl asialo GM1 glycolipids on the small intestinal epithelial cells in the ex-germ-free mouse.

In ex-germ-free mice conventionalized by association with fecal microorganisms, the induction fo major histocompatibility complex class II molecules and fucosylation of asialo GM1 glycolipid occur in the small intestinal epithelial cells (IEC). The intestinal intraepithelial lymphocytes (IEL), especially alpha beta T-cell receptor-bearing ones, also remarkably expand and show cytolytic activity. In this study, we investigated the immunological and physiological characteristics of the small intestine induced by a kind of indigenous bacteria of the small intestine, segmental filamentous bacteria (SFB), among chloroform-resistant intestinal bacteria. Monoassociation of SFB with germ-free mice was confirmed by the determination of the base sequences of polymerase chain reaction products of 16S rRNA genes of the fecal bacteria of these mice and in situ hybridization using fluorescein-labeled probes based on them. SFB increased the number of alpha beta TCR-bearing IEL and induced Thy-1 expression and cytolytic activity of IEL. The induction of MHC class II molecules and fucosyl asialo GM1 glycolipids and the increases in the mitotic activity and the ratio of the number of columnar cells to those of goblet cells also occurred in the small intestinal epithelial cells on monoassociation of these bacteria. SFB are important indigenous bacteria for the development of the mucosal architecture and immune system in the small intestine, at least in mice.

Animals↗
PubMed2001

Immunological properties of trehalose dimycolate (cord factor) and other mycolic acid-containing glycolipids--a review.

Mycolic acids are characteristic fatty acids of Mycobacteria and are responsible for the wax-like consistence of these microorganisms. Decades of research revealed that mycolic acid-containing glycolipids, in particular trehalose-6,6'-dimycolate (TDM, cord factor) as their best-studied representative, exert a number of immunomodifying effects. They are able to stimulate innate, early adaptive and both humoral and cellular adaptive immunity. Most functions can be associated with their ability to induce a wide range of chemokines (MCP-1, MIP-1alpha, IL-8) and cytokines (e.g., IL-12, IFN-gamma, TNF-alpha, IL-4, IL-6, IL-10). This review tries to link well-known properties of mycolic acid-containing glycolipids, e.g., stimulation of cellular and humoral immunity, granuloma formation and anti-tumor activity, with recent findings in molecular immunology and to give an outlook on potential practical applications.

Adjuvants, Immunologic↗
PubMed1991

Autoantibodies against Forssman glycolipids in Graves' disease and Hashimoto's thyroiditis.

Sera from patients with Graves' disease and Hashimoto's thyroiditis have been shown to react with the Forssman glycolipid antigen (Gb5) using the techniques of high performance thin-layer chromatography (HPTLC) immunostaining and ELISA. Human monoclonal antibodies (MoAbs) have been prepared by fusion of human myeloma with peripheral lymphocytes from patients with Graves' disease. A MoAb, TRMo-4, reacted strongly and specifically with Gb5. These results suggest that anti-Forssman antibody may be involved in the pathogenesis of these autoimmune diseases. The detection of anti-Forssman glycolipid antibody may provide a useful means for clinical diagnosis and therapy.

Antibodies, Monoclonal↗
PubMed2006

The CD1d-binding glycolipid alpha-galactosylceramide enhances humoral immunity to T-dependent and T-independent antigen in a CD1d-dependent manner.

Specific interaction of class II/peptide with the T-cell receptor (TCR) expressed by class II-restricted CD4+ T helper (Th) cells is essential for in vivo production of antibodies reactive with T-dependent antigen. In response to stimulation with CD1d-binding glycolipid, Valpha14+ TCR-expressing, CD1d-restricted natural killer T (NKT) cells may provide additional help for antibody production. We tested the hypothesis that the CD1d-binding glycolipid alpha-galactosylceramide (alpha-GC) enhances production of antibodies reactive with T-dependent antigen in vivo. alpha-GC enhanced antibody production in vivo in a CD1d-dependent manner in the presence of class II-restricted Th cells and induced a limited antibody response in Th-deficient mice. alpha-GC also led to alterations in isotype switch, selectively increasing production of immunoglobulin G2b. Further analysis revealed that alpha-GC led to priming of class II-restricted Th cells in vivo. Additionally, we observed that alpha-GC enhanced production of antibodies reactive with T-independent antigen, showing the effects of NKT cells on B cells independently of Th cells. Our data show that NKT cells have multiple effects on the induction of a humoral immune response. We propose that NKT cells could be exploited for the development of novel vaccines where protective antibody is required.

Animals↗
PubMed2004

Monoacylglycerols: glycolipid biosurfactants produced by a thermotolerant yeast, Candida ishiwadae.

AIMS: To isolate and characterize biosurfactants produced by a thermotolerant yeast isolated in Thailand. MATERIALS AND RESULTS: Yeast strains isolated from plant material in Thailand were first screened for the ability to produce lipase and biosurfactant. A strain Y12, identified as Candida ishiwadae by physiological tests, survived at 45 degrees C and produced relatively large amounts of biosurfactants. From the culture filtrate of this strain, two glycolipid biosurfactants, a and b, were purified by solvent fractionation, silica gel and ODS column chromatographies. Compounds a and b were determined to be monoacylglycerols; 1-linoleylglycerol and 1-oleylglycerol, respectively. Both compounds exhibited higher surfactant activities tested by the drop collapse test than several artificial surfactants such as sodium dodecyl sulphate. CONCLUSIONS: Glycolipid biosurfactants produced by a thermotolerant yeast, C. ishiwadae were characterized to be monoacylglycerols which exhibited high surfactant activities. SIGNIFICANCE AND IMPACT OF THE STUDY: A thermotolerant yeast strain, C. ishiwadae, could be a potential candidate for producing monoacylglycerols which are useful in industrial applications.

Bioreactors↗
PubMed1986

Complete structural analysis of globoseries glycolipids by two-dimensional nuclear magnetic resonance.

Combined two-dimensional proton nuclear magnetic resonance allowed the determination of complete oligosaccharide structures of glycolipids belonging to the globo series, without any other analytical methods. Although a chemical modification by peracetylation was required for the above purpose, the derivatization permitted facile assignment of the pyranose ring proton resonances of the oligosaccharide moiety. Two-dimensional chemical-shift-correlated spectroscopy of the acetylated glycolipid enabled us to elucidate the glycosidic positions from the chemical shifts of the protons at the substituted sites. The monosaccharide species were also identified from the characteristic splitting patterns of the methine protons on individual pyranose rings. The sequence of the monosaccharides was inferred from the interresidue connectivity across glycosidic linkages shown by two-dimensional nuclear Overhauser effect spectroscopy, which also gave intraresidue interaction on the pyranose rings. The linkage sites of long oligosaccharide chains having more than five monosaccharides, such as globopentaosylceramide, were analyzed by two-dimensional J-relayed coherence transfer, which yielded 1,3 interactions along with 1,2 interactions.

Acetylation↗
PubMed1993

Evidence for a glycolipid anchor of gp64, a putative cell-cell adhesion protein of Polysphondylium pallidum.

The membrane-bound glycoprotein (gp64) of the cellular slime mold Polysphondylium pallidum, is a putative cell-cell adhesion protein identified by adhesion-blocking antibody fragments. Since gp64 can be purified in a few days and in substantial yields, it is a good candidate for clarifying the structure of a cell-cell adhesion protein. This study reveals that gp64 possesses a glycolipid anchor which is sensitive to deamination but resistant to phosphatidylinositol-specific phospholipase C from Bacillus thuringiensis. Although the anchor resistance to phosphatidylinositol-specific phospholipase C can be ascribed to the presence of an additional acyl chain on the inositol ring in the glycosyl phosphatidylinositol anchors, this was not the case. After a mild-base treatment that released an additional acyl chain on the inositol ring, only a trace amount of fatty acid was detected but, after strong acid hydrolysis, we detected both amide-linked fatty acids and a long-chain base. The long-chain base was further analysed by gas-chromatography/mass spectrometry and was found to be phytosphingosine. Both fatty acids and myo-inositol were also analysed by gas-chromatography/mass spectrometry. These data suggest that gp64 possesses a glycolipid anchor which contains ceramide and myo-inositol.

Bacillus thuringiensis↗
PubMed1990

Developmental expression of HNK-1-reactive antigens in the rat cerebellum and localization of sulfoglucuronyl glycolipids in molecular layer and deep cerebellar nuclei.

Monoclonal antibody HNK-1-reactive carbohydrate epitope is expressed on proteins, proteoglycans, and sulfoglucuronyl glycolipids (SGGLs). The developmental expression of these HNK-1-reactive antigens was studied in rat cerebellum. The expression of sulfoglucuronyl lacto-N-neotetraosylceramide (SGGL-1) was biphasic with an initial maximum at postnatal day one (PD 1), followed by a second rise in the level at PD 20. The level of sulfoglucuronyl lacto-N-norhexaosyl ceramide (SGGL-2) in cerebellum was low until PD 15 and then increased to a plateau at PD 20. The levels of SGGLs increased during postnatal development of the cerebellum, contrary to their diminishing expression in the cerebral cortex. The expression of HNK-1-reactive glycoproteins decreased with development of the rat cerebellum from PD 1. Several HNK-1-reactive glycoproteins with apparent molecular masses between 150 and 325 kDa were visualized between PD 1 and PD 10. However, beyond PD 10, only two HNK-1-reactive bands at 160 and 180 kDa remained. The latter appeared to be neural cell adhesion molecule, N-CAM-180. A diffuse HNK-1-reactive band seen at the top of polyacrylamide electrophoretic gels was due mostly to proteoglycans. This band increased in its reactivity to HNK-1 between PD 15 and PD 25 and then decreased in the adult cerebellum. The lipid antigens were shown by two complementary methodologies to be localized primarily in the molecular layer and deep cerebellar nuclei as opposed to the granular layer and white matter. A fixation procedure which eliminates HNK-1-reactive epitope on glycoproteins and proteoglycans, but does not affect glycolipids, allowed selective immunoreactivity in the molecular layer and deep cerebellar nuclei.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMed2001

Glycolipid antigen processing for presentation by CD1d molecules.

The requirement for processing glycolipid antigens in T cell recognition was examined with mouse CD1d-mediated responses to glycosphingolipids (GSLs). Although some disaccharide GSL antigens can be recognized without processing, the responses to three other antigens, including the disaccharide GSL Gal(alpha1-->2)GalCer (Gal, galactose; GalCer, galactosylceramide), required removal of the terminal sugars to permit interaction with the T cell receptor. A lysosomal enzyme, alpha-galactosidase A, was responsible for the processing of Gal(alpha1-->2)GalCer to generate the antigenic monosaccharide epitope. These data demonstrate a carbohydrate antigen processing system analogous to that used for peptides and an ability of T cells to recognize processed fragments of complex glycolipids.

Amino Acid Motifs↗
PubMed1984

Formation and identification of interfacial-active glycolipids from resting microbial cells.

Resting cells of Arthrobacter sp. strain DSM2567 incubated in the presence of various mono-, di-, or trisaccharides biosynthesized different glycolipids. All eight glycolipids, containing the corresponding carbohydrate moiety and one, two, or three alpha-branched beta-hydroxy fatty acids, were produced when mannose, glucose, cellobiose, maltose, and maltotriose were used as carbon sources in a simple phosphate buffer. The structures of the compounds were elucidated by means of H and C nuclear magnetic resonance spectroscopy and by chemical ionization mass spectroscopy. In high-salinity solution, the substances showed different surfactant properties. Cellobiose and maltose monocorynomycolates reduced the interfacial tension from 42 to 1 mN/m at critical micelle concentrations below 20 mg/liter.

Journal Article↗
PubMed2003

Forssman synthetase expression results in diminished shiga toxin susceptibility: a role for glycolipids in determining host-microbe interactions.

Forssman glycolipid (FG), the product of Forssman synthetase (FS), is widely expressed among nonprimate mammalian species. Here, we describe a molecular and genetic relationship between FG expression and Shiga toxin (Stx) susceptibility. We have isolated the FS cDNA from human, canine, and murine cells. Whereas the murine and canine FS genes express a functional enzyme, the human FS cDNA was found to express a protein that lacks FS activity, despite a high degree of sequence identity with the enzymatically active murine and canine FS genes. In order to examine the relationship between FG expression and Stx susceptibility, Vero cells were transfected with the three FS orthologues or a vector control. Complementation with the human FS cDNA had no effect on Stx susceptibility, whereas stable expression of the canine and murine FS resulted in markedly decreased susceptibility to toxin. Among individual cells, an inverse correlation between FG expression and Stx binding was demonstrated. Moreover, only strongly FG-reactive cells were capable of growing in the presence of Stx. These cells were found to have high levels of FG expression and a correspondingly diminished GbO(3) content. We conclude that expression of a functionally active FS modifies Stx receptor glycolipids to FG and results in markedly decreased susceptibility to toxin. We speculate that inactivation of the FS gene during primate evolution may account, at least in part, for the marked susceptibility of human cells to Stx.

Amino Acid Sequence↗
PubMed1978

Glycolipids stimulate DNA polymerase activity in a DNA-membrane fraction and in a partially purified polymerase system extracted from pneumococci.

We have assayed the ability of various lipids to affect DNA polymerases activity in a DNA-membrane complex extracted from Streptococcus pneumoniae by the Sarkosyl-M-band technique. In addition, to determine which DNA polymerases were affected by the lipids, we partially purified three DNA polymerase activities from cell lysates, the first such demonstration outside of Escherichia coli and Bacillus subtilis. Glycolipids are unique among polar lipids in stimulating the rate and extent of DNA polymerase activity in M-bands and in Sarkosyl lysates from which the M-band is derived. It appears that they exert this stimulatory effect, in part, by removing (neutralizing) detergent molecules which act as inhibitors, as well as by substituting for the detergent, thereby creating a favorable environment for the polymerases involved in DNA synthesis. That the stimulatory effect is not simply a detoxification of the detergent was shown by two observations. One, phospholipids, although interacting with Sarkosyl and therefore "potentially" capable of detoxifying the system, did not stimulate DNA polymerase activity in vitro. Two, glycolipids were capable of stimulating the activity of at least two DNA polymerases partially purified from cell lysates in the absence of any Sarkosyl. The stimulatory effect was greater for a polymerase that had four characteristics similar to those observed with polymerase III in other organisms.

DNA, Bacterial↗
PubMed1967

Phospholipids and glycolipids of sterol-requiring Mycoplasma.

The phospholipids of Mycoplasma hominis type 2 strain 07 are composed almost entirely of phosphatidyl glycerol. Traces of other glycerophospholipids may exist. No glycolipids are found. The phospholipids of Mycoplasma sp. avian strain J are composed of diphosphatidyl glycerol, which predominates in older cultures, a monoacyl glycerophosphoryl glycerophosphate, which may serve as a precursor of diphosphatidyl glycerol, and phosphatidyl glycerophosphate. This organism also contains cholesteryl glucoside and an unidentified glycolipid which appears to be similar to a monoglucosyl diglyceride. No turnover or radioisotope labeling of the phospholipids occurs during metabolism. This lack of turnover during growth is indicative of a structural role for these glycerophospholipids. A concomitant decrease of monoacyl glycerophosphoryl glycerophosphate and increase of diphosphatidyl glycerol occurs during growth.

Fatty Acids↗
PubMedDate not supplied

Mycobacterial glycolipid cord factor trehalose 6,6'-dimycolate causes a decrease in serum cortisol during the granulomatous response.

Serum cortisol levels were evaluated in mice following intravenous administration of purified mycobacterial glycolipid trehalose 6,6'-dimycolate (TDM). C57BL/6 mice develop lung granulomas in response to TDM, while A/J mice are deficient in this process. Administration of TDM to C57BL/6 mice led to a rapid reduction in serum cortisol, concurrent with initiation of the granulomatous response and cytokine and chemokine mRNA induction. Cortisol levels were lowest on day 5 after TDM administration, but there was significant production of IL-6, TNF-alpha and IL-1beta messages. Granuloma formation and full immune responsiveness to TDM were only apparent upon a sufficient decrease in levels of systemic cortisol. Treatment of the C57BL/6 mice with hydrocortisone abolished inflammatory responses. Histologically nonresponding A/J mice exhibited higher constitutive serum cortisol and demonstrated different kinetics of cortisol reduction upon administration of TDM. A/J mice demonstrated hyperplastic morphology in the suprarenal gland with a high degree of vacuolization in the medullary region and activation of cells in the zona fasciculata and zona reticularis. The A/J mice were dysregulated with respect to cytokine responses thought to be necessary during granuloma formation. The high constitutive serum cortisol in the A/J mice may therefore contribute to pulmonary immunoresponsiveness and the establishment of an environment counterproductive to the initiation of granulomatous responses. The identification of a mycobacterial glycolipid able to influence serum cortisol levels is unique and is discussed in relation to immunopathology during tuberculosis disease.

Adrenal Cortex↗
PubMed1986

The effects of glycolipids and carbohydrates on bilirubin cytotoxicity in vitro.

We have studied the inhibitory effects of various glycolipids including gangliosides and carbohydrates on bilirubin cytotoxicity towards human glia cells using a 51Cr release assay. All cytotoxic activity was abolished when 100 microM bilirubin was incubated with 40-80 microM gangliosides (GM1, galactosyl-N-acetylgalactosaminyl-(N-acetylneuraminyl) galactosylglucosylceramide; GM2, N-acetylgalactosaminyl-(N-acetylneuraminyl)galactosylglucosylceramide; GM3, N-acetylneuraminylgalactosylglucosylceramide, and GD1a, N-acetylneuraminylgalactosyl-N-acetylgalactosaminyl-(N-acetylneura minyl) galactosylglucosylceramide). On the other hand, inhibition by asialoglycolipids was less effective than that by gangliosides, but became more effective with increasing numbers of sugars per molecule, the efficacy of inhibition being as follows: globoside greater than trihexosyl ceramide greater than lactosyl ceramide greater than glucosyl ceramide. Glucosyl ceramide and the carbohydrates of neuramine lactose or N-acetylneuraminic acid (NANA) did not have inhibitory effects. These results suggest that the terminal acidic group of NANA and the numbers of sugar chains in glycolipids play important roles in the inhibition of bilirubin cytotoxicity.

Bilirubin↗
PubMed1996

Mycobacterium fortuitum glycolipids for the serodiagnosis of pulmonary tuberculosis.

Glycolipids belonging to the family of acylated trehaloses were isolated from Mycobacterium fortuitum, a rapidly growing mycobacterial species, and tested in the serologic diagnosis of human pulmonary tuberculosis by enzyme-linked immunosorbent assay. Di- and tri-O-acylated trehaloses from M. fortuitum reacted with serum antibodies of patients with pulmonary tuberculosis at higher titers than did with sera from healthy donors. With both glycolipids, the sensitivity of the test was above 0.80 at a chosen specificity of 0.98. Individuals with treated tuberculosis showed lower antibody titers compared with their initial reactivities. These data show that M. fortuitum could be used as a surrogate source of antigens for tuberculosis serodiagnosis.

Acetylation↗