Studies on Glycosphingolipids of Fresh-Water Bivalves

Itasaka, Osamu; Hori, Taro

doi:10.1093/oxfordjournals.jbchem.a132475

Cited by 40 publications

(6 citation statements)

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“…C-6 linked, sugar-phosphoethanolamine moieties are not restricted to the glycosphingolipids of insects, being present in freshwater [29] and marine 1301 molluscs, however, in the Diptera studied so far this amphoteric residue has been found to be bound only to N-acetylglucosamine 16, 271.…”

Section: Discussionmentioning

confidence: 95%

Glycosphingolipids in insects

Helling

Dennis

Weske

et al. 1991

European Journal of Biochemistry

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A group of Calliphoru vicinu pupal glycolipids could be segregated from the neutral glycosphingolipids, according to their two-dimensional TLC migration properties and positive reactions toward ninhydrin and fluorescamine spray reagents. These classified zwitterionic glycolipids were isolated by silica-gel column chromatography and characterized by the presence of a N-acetyl-glucosamine-bound phosphoethanolamine residue. The structural elucidation of the oligosaccharide moieties was performed by the determination of constituent carbohydrates as alditol acetates, linkage analysis by permethylation, exoglycosidase cleavage, fast-atombombardment mass spectrometry and NMR spectroscopy. The dominant fatty acid and sphingoid base species of the ceramide moieties were C2,: , (arachidic acid) and C14: (tetradecasphing-4-enine), respectively. The chemical structures of the zwitterionic, biogenetic glycosphingolipid series were determined as :

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Section: Discussionmentioning

confidence: 95%

Glycosphingolipids in insects

Helling

Dennis

Weske

et al. 1991

European Journal of Biochemistry

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“…Zwitterionic glycosphingolipids have been structurally characterized from various members of the invertebrate phyla, including identification of the monosaccharide-amphoteric moiety in the Sarcomastigophora (Flagellata) as Man-phosphoethanolamine (39), in the Annelida as Gal-phosphocholine (40)(41)(42)(43)(44), in the Arthropoda (Crustacea) as Glc-phosphonoethanolamine (45), in the Arthropoda (Insecta) as GlcNAc-phosphoethanolamine (33,46,47), in the Mollusca (freshwater Bivalvia) as Man-phosphoethanolamine (48), in the Mollusca (marine Gastropoda) as Gal-phosphonoethanolamine (49,50), and in the Nematoda (Ascaridida) as GlcNAc-phosphocholine and Man-phosphoethanolamine (Ref. 3 and this publication).…”

Section: Discussionmentioning

confidence: 99%

Structural Elucidation and Monokine-inducing Activity of Two Biologically Active Zwitterionic Glycosphingolipids Derived from the Porcine Parasitic Nematode Ascaris suum

Lochnit¹,

Dennis²,

Ulmer³

et al. 1998

Journal of Biological Chemistry

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The isolated neutral glycosphingolipid fraction from the pig parasitic nematode, Ascaris suum, was fractionated by silica gel chromatography to yield a neutral and a zwitterionic glycosphingolipid fraction, the latter of which mainly contained two zwitterionic glycosphingolipids termed components A and C. Preliminary chemical characterization with hydrofluoric acid treatment and immunochemical characterization with a phosphocholine-specific monoclonal antibody indicated that both components contained phosphodiester substitutions: phosphocholine for component A, and phosphocholine and phosphoethanolamine for component C. Both components were biologically active in inducing human peripheral blood mononuclear cells to release the inflammatory monokines tumor necrosis factor ␣, interleukin 1, and interleukin 6. Component A was the more bioactive molecule, and its biological activity was abolished on removal of the phosphocholine substituent by hydrofluoric acid. The glycosphingolipid components were structurally analyzed by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, liquid secondary ion mass spectrometry, methylation analysis, 1 H NMR spectroscopy, exoglycosidase cleavage, and ceramide analysis. Their chemical structures were elucidated to be (see Structure I below), The carbohydrate moiety oligosaccharide core was characterized as belonging to the arthro series of protostomial glycosphingolipids. The ceramide moiety was distinguished by (R)-2-hydroxytetracosanoic acid as the dominant fatty acid species and by the C17 iso-branched sphingosine and sphinganine bases, 15-methylhexadecasphing-4-enine and 15-methylhexadecasphinganine, respectively.Analyses of the immunoreactivity between neutral fraction glycolipids derived from various species of parasitic nematodes have indicated a high degree of serological cross-reactivity (1, 2). The structural basis for this immunological cross-reactivity between parasitic nematodes at the level of glycolipids is at present unknown. Structural studies on the neutral fraction glycosphingolipids from adults of the porcine parasitic nematode Ascaris suum have revealed that the identified arthro series oligosaccharide chain was not immunogenic, i.e. did not exhibit immunoreactivity toward infection sera from A. suuminfected mice (2, 3). However, a zwitterionic glycosphingolipid fraction was also isolated from A. suum that demonstrated a phosphodiester sidechain as a structural modification of possibly phosphocholine (PC) 1 and phosphoethanolamine (PE). In addition, these zwitterionic glycolipids were immunogenic/antigenic, i.e. exhibited immunoreactivity toward infection sera from A. suum-infected mice (2).PC-containing macromolecules have been regularly detected * This project was supported by the Deutsche Forschungsgemeinschaft (SFB 535 and Graduiertenkolleg Molecular Biology and Pharmacology) and by the Bundesministerium fü r Bildung, Wissenschaft, Forschung und Technologie Grant 01 KI 9471. The costs of publication of this article were defrayed in...

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“…Acid in the aqueous layer was removed under reduced pressure. HF treatment of metabolically labeled [3H]LPG (3 x 105 cpm) was as described above except that the acid was neutralized with saturated LiOH (19) and the products were fractionated on a Fractogel TSK HW40(s) (Merck) gel filtration column (1.5 x 100 cm) in 0.1 M Tes buffer/0.5 M NaCl, pH 7.0. The column was calibrated with a series of malto-oligosaccharide standards (Sigma) loaded onto the column together with the sample.…”

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confidence: 99%

Lipophosphoglycan of Leishmania major that vaccinates against cutaneous leishmaniasis contains an alkylglycerophosphoinositol lipid anchor.

McConville

Bacic

Mitchell

et al. 1987

Proc. Natl. Acad. Sci. U.S.A.

151

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The major cell surface glycoconjugate of Leishmania major, a putative parasite receptor for macrophages, is a lipophosphoglycan containing 81.6% (wt/wt) carbohydrate, 17.0% (wt/wt) phosphate, and 1.4% (wt/wt) lipid. It has been purified to homogeneity by hydrophobic chromatography and consists of a polydisperse family of molecules with Mr 5000-40,000. It contains galactose, mannose, glucose, arabinose, glucosamine, and inositol in the molar ratio of 51:21:5:6:1:1. The lipophosphoglycan has a complex structure, consisting mainly of tri-and tetrasaccharide units linked by phosphodiester bonds, which are cleaved by HF hydrolysis. The phosphate groups are located on the 6-hydroxyl of both galactose and mannose residues. The lipophosphoglycan is anchored to the parasite surface by a 1-O-alkyl-snglycero-3-phosphoinositol moiety. This conclusion is supported by analysis of the products of nitrous acid deamination, HF hydrolysis, and Staphylococcus aureus phosphatidylinositol specific-phospholipase C treatment. The 24:0 and 26:0 alkyl chains accounted for 93% of the ether-linked fatty acids in the lipid anchor. The results are also consistent with a glycosidic linkage between the inositol and a non-N-acetylated glucosamine residue. The lipophosphoglycan membrane anchor shares limited structural homology with the glycosylphosphatidylinositol anchors of several eukaryotic proteins, indicating that this type of membrane anchor is not limited to proteins. Vaccination of mice with the purified L. major lipophosphoglycan in liposomes induced resistance against cutaneous leishmaniasis.Essential for the establishment of infection by the obligatory intramacrophage parasite Leishmania major are four sequential events: recognition, intracellular entry, survival, and replication (1,2). A family of lipoglycoconjugates on the cell surface of L. major, the etiological agent of cutaneous leishmaniasis, are putative parasite recognition molecules for macrophages of the mammalian host (3). A molecule with similar chemical properties has been isolated from Leishmania donovani, the etiological agent of visceral leishmaniasis, and partially characterized as a lipophosphoglycan (LPG) containing mannose, galactose, and phosphate (4, 5). The presence of a hydrophobic lipid moiety in the Leishmania LPGs was indicated by their amphipathic properties and by biosynthetic labeling with fatty acids (4, 6, 7). This lipid could be removed by treatment of LPG with phospholipase C (3). These glycoconjugates are part of a polymorphic family of similar but antigenically distinct molecules present in all Leishmania species (6,8) and have formed the basis for the classification of Leishmania.The localization of the L. major LPG on the surface of both the promastigote and infected macrophage (6) made it an attractive candidate for a vaccine. This was confirmed by studies showing that L. major LPG, immunoaffinity purified from detergent extracts by using the monoclonal antibody WIC-79.3, protected mice against cutaneous leishmaniasis (9).In this ...

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Studies on Glycosphingolipids of Fresh-Water Bivalves

Cited by 40 publications

References 0 publications

Glycosphingolipids in insects

Glycosphingolipids in insects

Structural Elucidation and Monokine-inducing Activity of Two Biologically Active Zwitterionic Glycosphingolipids Derived from the Porcine Parasitic Nematode Ascaris suum

Lipophosphoglycan of Leishmania major that vaccinates against cutaneous leishmaniasis contains an alkylglycerophosphoinositol lipid anchor.

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