Glycosphingolipids in insects

Helling, Friedhelm; Dennis, Roger D.; Weske, Bianka; Nores, Gustavo A.; Peter‐Katalinić, Jasna; Dąbrowski, Ursula; Egge, Heinz; Wiegandt, Herbert

doi:10.1111/j.1432-1033.1991.tb16199.x

Cited by 42 publications

(29 citation statements)

References 28 publications

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“…It is now evident (this publication) that this banding within groups, a phenomenon well known for glycosphingolipids of vertebrate origin, in the case of the parasite glycolipids is also clearly related to differences in the respective ceramide composition, whilst groups of TLC bands of glycosphingolipids are distinguished from one another by differences in the size of the carbohydrate moiety. Under the TLC conditions employed, no heterogeneity of the ceramide residue influencing migration is observed with the neutral fraction C. vicina glycosphingolipids used as standards [46].…”

Section: Discussionmentioning

confidence: 99%

Glycosphingolipids in cestodes

Dennis

Baumeister

Geyer

et al. 1992

European Journal of Biochemistry

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The presence of glycosphingolipids in the metacestodes of the fox tapeworm, Tueniu crassiceps, has been established. The normal-phase TLC pattern of the neutral-fraction glycolipids revealed groups of bands corresponding to homologous components of increasing sugar chain length. The three simplest glycolipid components have been isolated and their chemical constitution determined as being of the neogala series: Galpl Cer, Galp6Galpl Cer and Galp6Galfl6Galbl Cer. The ceramide tetrasaccharide fraction has been found to consist of a mixture of neogalatetraosylceramide, as an elongation of the neogala series, Gal/36Galp6Galp6GalplCer and the component Gala4Galp6-GalB6GalplCer (both occurring in approximately equimolar proportions). The long-chain bases of the ceramide monogalactoside, digalactoside, trigalactoside and tetragalactosides contain, as well as small amounts of sphingosine, predominantly dihydrosphingosine/phytosphingosine in the approximate ratios 1.7: 1, 1.4: 1 , l : 1 and 2.3: 1, respectively. The major ceramide fatty acids have particularly long chains, with hexacosanoic and octacosanoic acids predominating. Upon reverse-phase TLC, the glycolipid components ceramide monogalactoside, digalactoside and trigalactoside were each separable into five component bands. Parent glycolipid components therefore show component band distributions comparable to one another in being governed by similar ceramide constitutions.As a possible reflection of their general relevance in biology, glycolipids are widely distributed in tissues of plants [l, 21, animals [3] An investigation of the glycolipids of multicellular parasites (protozoan parasites do not appear to contain major amounts of classical glycosphingolipids, i.e. compounds containing sugar linked to ceramide) was initiated in this laboratory, with the aim of increasing our knowledge of the diversity and distribution of their glycosphingolipids. It is hoped that this information will contribute to a better understanding of the putative roles of parasite glycosphingolipids in the maintenance of parasite integrity, in the mediation of parasite/ host interactions and in their significance in the host immune response. As a model, the metacestode stage of Taenia crassiceps has been chosen because of its relevance to other parasitic helminths that are pathogenic in humans, as well as for ease of propagation in laboratory mice [12]. Preliminary data have shown their neutral-fraction glycolipids to be antigenic, as evidenced by immunoreactivity (ELISA and HPTLC immunostaining) towards T. crassiceps metacestode-elicited infection serum, and, interestingly, against an affinitycolumn-isolated fraction [with parasite-derived ceramide trihexoside (CTH) as the ligand] [13].The results have shown that T. crassiceps metacestodes contain an array of glycolipids which can be separated by TLC into groups of chromatographic bands corresponding to homologous components of increasing sugar chain length. Isolation of ceramide monosaccharide, disaccharide, trisaccharide and tetrasa...

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Section: Discussionmentioning

confidence: 99%

Glycosphingolipids in cestodes

Dennis

Baumeister

Geyer

et al. 1992

European Journal of Biochemistry

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“…The structure of higher order sphingolipids has been studied in dipterans (23)(24)(25)(26)(27). However, until the last few years, relatively little information about sphingolipid structure and function in Drosophila has been available.…”

Section: Discussionmentioning

confidence: 99%

Identification and characterization by electrospray mass spectrometry of endogenous Drosophila sphingadienes

Fyrst¹,

Zhang

Herr

et al. 2008

Journal of Lipid Research

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Sphingolipids comprise a complex group of lipids concentrated in membrane rafts and whose metabolites function as signaling molecules. Sphingolipids are conserved in Drosophila, in which their tight regulation is required for proper development and tissue integrity. In this study, we identified a new family of Drosophila sphingolipids containing two double bonds in the long chain base (LCB). The lipids were found at low levels in wild-type flies and accumulated markedly in Drosophila Sply mutants, which do not express sphingosine-1-phosphate lyase and are defective in sphingolipid catabolism. To determine the identity of the unknown lipids, purified whole fly lipid extracts were separated on a C18-HPLC column and analyzed using electrospray mass spectrometry. The lipids contain a LCB of either 14 or 16 carbons with conjugated double bonds at C4,6. The Sphingolipids are a diverse group of membrane lipids that are highly conserved throughout evolution (1, 2). In mammalian cells, sphingolipid structure, composition, and metabolism have been well characterized. Knowledge of sphingolipid structure has facilitated in-depth analyses of the contribution of sphingolipids to membrane organization and their function in signal transduction events and normal physiology. Such studies have defined an important role for higher order sphingolipids in the formation of membrane subdomains (lipid rafts) wherein growth factor signaling and recruitment occur (3-6), and sphingolipid metabolites have been shown to participate in signaling pathways regulating the key processes of cellular proliferation, migration, stress responses, programmed cell death, angiogenesis, and immune cell trafficking (7-12).We have been exploring the physiological roles of sphingolipids in the genetically tractable organism, Drosophila melanogaster. In this species, tight regulation of sphingolipid levels is required for proper development, reproduction, and the maintenance of tissue integrity, as demonstrated by the severe phenotypes observed in mutants with disrupted sphingolipid metabolism (13-17). However, a clear understanding of the role of sphingolipid metabolism and, in particular, the mechanisms by which sphingolipid metabolites influence physiological processes in this organism has been hampered by an incomplete knowledge of the chemical structures of endogenous Drosophila sphingolipids and their metabolic products.Previously, we found that the Drosophila free sphingoid bases or long chain bases (LCBs) are composed largely of C 14 -and C 16 -sphingosine and dihydrosphingosine (18). In the current study, we have identified a second family of sphingolipids recognized by their differential separation on HPLC compared with known Drosophila sphingolipid species. Mass spectrometry approaches were used to characterize the structures of these unknown lipids as C 14 -and C 16 -sphingadienes with D-4,6 conjugated double bonds and to further identify a family of related lipids built upon the same D Abbreviations: dsRNA, double-stranded RNA; LCB, long...

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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%

“…ment after the permethylation procedure revealed for compound A the presence of a 4,6-disubstituted N-acetylglucosamine (Table II, column A2) that indicated location of the phosphocholine substituent at the C-6 of N-acetylglucosamine. For compound C, a 4,6-disubstituted N-acetylglucosamine and a 3,6-disubstituted mannose were found along with 3-substituted mannose (Table II, column C2), the latter of which is formed due to the lability of the phosphoethanolamine substituent to the conditions of the permethylation procedure (33). If the phosphoethanolamine substituent was stabilized by methylation to choline before permethylation, the major mannose constituent was found to be 3,6-disubstituted mannose, indicating the localization of phosphoethanolamine at the C-6 of mannose (Table II, …”

Section: Isolation Of Zwitterionic Components a And C-glycosphin-mentioning

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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Glycosphingolipids in insects

Cited by 42 publications

References 28 publications

Glycosphingolipids in cestodes

Glycosphingolipids in cestodes

Identification and characterization by electrospray mass spectrometry of endogenous Drosophila sphingadienes

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

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