Insects: Animals Without Gangliosides — Preliminary Data

Dennis, Roger D.; Geyer, Rudolf; Egge, Heinz; Peter‐Katalinić, Jasna; Keller, Martin D.; Menges, Hans; Wiegandt, Herbert

doi:10.1007/978-3-642-71932-5_32

Cited by 6 publications

(15 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In this publication, we report the structural elucidation of the two major arthrosides, A5c and Az5c from C. vicina pupae, by fast-atom-bombardment mass spectrometric data and preliminary data of the carbohydrate sequence [4]. The results confirm the original proposal of Dennis et al [5].…”

supporting

confidence: 75%

“…Its structure deviates from a similar compound, the previously characterized ceramide pentasaccharide 5B [2] that carried a terminal Ngalactosyl residue linked to the same tetrasaccharide, i.e. IV3-Galcr-Ap,Cer.…”

Section: Discussionmentioning

confidence: 54%

“…This was fractionated on a DEAE-Sephadex column, equilibrated with methanol, by a stepwise-gradient of ammonium acetate in methanol (0.02, 0.04 and 0.3 M). Single components were isolated by preparative HPLC [2], with elution of the main acidic glycolipids, A5c and AzSc, using a linear gradient of 2-propanollnhexane/water (55:33:12 to 55:28:17) at 2ml/min and 1.0-ml fractions.…”

Section: Isolation and Purification Of The Acidic Fraction Glycolipidsmentioning

confidence: 99%

“…With elongation of the core structure, arthrotetraosylceramide (Ap,Cer), at least three different oligosaccharide chain sequences appear. Elongation with an a-GalNAc residue corresponds to the originally isolated ceramide pentasaccharide 5A (IV4GalNAca-Ap4Cer), whilst the b component corresponds to the originally isolated ceramide pentasaccharide (IV3Gala-Ap4Cer) [2]. A c pentahexosylceramide has now been established as identical to the b component except for the anomeric configuration of the terminal Gal residue, which is /?-linked: 5c (IV3Galj-Ap4Cer).…”

mentioning

confidence: 99%

“…Neutral species (N1 -7), containing one to seven neutral sugars in the particular arthro-series sequence [2,31 ; zwitterionic species (Nz3 -7), containing from three to seven neutral sugars of the neutral oligosaccharide chain and an N-acetylglucosaminebound phosphoethanolamine moiety at the third monosaccharide residue [4]; and the acidic species (A), which may (Az) or may not carry the phosphoethanolamine sidechain.…”

mentioning

confidence: 99%

See 4 more Smart Citations

Glycosphingolipids in insects

Weske

Dennis²,

Helling³

et al. 1990

European Journal of Biochemistry

View full text Add to dashboard Cite

The two major components of the acidic glycolipid fraction from the pupae of Calliphora vicina were isolated using high-performance liquid chromatography. The acidic moiety was identified as glucuronic acid by jglucuronidase cleavage and gas chromatographic analysis as the pentafluoropropionyl derivative. The structures of the carbohydrate moiety were elucidated by peracetylation, methylation, exoglycosidase cleavage, fast-atombombardment mass spectrometric and 'H-nuclear magnetic resonance spectroscopic analysis. The only difference between the two hexasaccharide variants was the presence, in one of them, of a phosphoethanolamine (AeP) sidechain on the third sugar of the sequence, i. e. N-acetylglucosamine. The composition of the ceramide moiety was dominated by a C2,, : fatty acid (arachidic acid) and a CI4 : sphingoid base (tetradecasphing-4-enine). The chemical structures of the two insect acidic glycosphingolipids were determined to be:Such glucuronic-acid-containing insect glycosphingolipids have been given the generic name arthrosides, with the implied synonymity to the gangliosides.Systematic structural elucidation of glycosphingolipids from members of the phyla Mollusca and Athropoda (class: Insecta) of the Invertebrata (Protostomia) have revealed major divergences in the carbohydrate moiety compared to those of the Vertebrata (Deuterostomia). The mollu series (Ml) of the Mollusca and arthro series (Ap) of the Arthropoda are characterised by a mactose-containing ceramide disaccharide in which the galactose residue of vertebrate lactose is replaced by mannose. Abbreviations. Gangliosides of the sialoganglio series are designated as was suggested previously [I] : GI,,I = I13NeuAc-LacCer, G,,,l = I13NeuAc-Gg,Cer. The shorthand abbreviations of glycosphingolipids (GSL) of the arthro series (Ap), characterized by the monosaccharide sequence of the arthroheptaose (Ap7) GlcNAcPl3GalP1 -3GalNAcal -4GalNAcP1 -4GlcNAcPI -3ManDl -4Glc, are N, Nz, A, and Az, where N stands for GSL with a neutral oligosaccharide chain, A for those with an additional acidic substituent (glucuronic acid); the lower case letter z is added for members that carry the zwitterionic substituent 2-aminoethylphosphate; arabic numerals 1-7 indicate the number of constituent neutral monosaccharides. In the case of two isomeric ceramide pentahexosides, a lower-case letter b or c distinguishes IV3Gala-Ap,Cer (N5b) and IV3GalP-Ap,Cer ( N~c ) , respectively. Mab, monoclonal antibody; Mac, mactose, i. e. Manp(1-4)Glc; FAB-MS, fast atom-bombardment mass spectrometry.Enzymes. P-Glucuronidase (EC 3.2.1.31), P-galactosidase (EC 3.2.1.23).

show abstract

supporting

confidence: 75%

Section: Discussionmentioning

confidence: 54%

Section: Isolation and Purification Of The Acidic Fraction Glycolipidsmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 3 more Smart Citations

Glycosphingolipids in insects

Weske

Dennis²,

Helling³

et al. 1990

European Journal of Biochemistry

View full text Add to dashboard Cite

show abstract

Fast atom bombardment mass spectrometry for structural elucidation of glycoconjugates

Egge

Peter‐Katalinić

1987

Mass Spectrometry Reviews

228

View full text Add to dashboard Cite

Expression of carbohydrate epitopes L2/HNK-1 and L3 in the larva and imago of Drosophila melanogaster and Calliphora vicina

1991

View full text Add to dashboard Cite

The carbohydrate epitopes L2/HNK-1 and L3 belong to two overlapping families of adhesion molecules in the vertebrate, and probably the invertebrate nervous systems. To investigate their pattern of expression during the development of insects, cryosections of late third instar larvae and imagoes of Drosophila melanogaster and Calliphora vicina were studied by indirect immunofluorescence using several monoclonal antibodies to the L2/HNK-1 and one monoclonal antibody to the L3 epitope. Each monoclonal antibody to the L2/HNK-1 epitope showed a different immunohistological staining pattern, which differed from that of the L3 monoclonal antibody. In both insect species the immunohistological staining patterns for the two carbohydrate epitopes were similar at the two developmental stages, with immunoreactivity not confined to the nervous system. In larvae, immunoreactivities of the monoclonal antibodies L2.334 and L3.492 were predominantly associated with the extracellular matrix as indicated by co-localization with laminin, particularly in the imaginal discs, while L2.349 revealed a more cell surface-associated distribution. In imagoes, immunoreactivities were detectable in most organs studied.

show abstract

Insects: Animals Without Gangliosides — Preliminary Data

Cited by 6 publications

References 31 publications

Glycosphingolipids in insects

Glycosphingolipids in insects

Fast atom bombardment mass spectrometry for structural elucidation of glycoconjugates

Expression of carbohydrate epitopes L2/HNK-1 and L3 in the larva and imago of Drosophila melanogaster and Calliphora vicina

Contact Info

Product

Resources

About