Structural characterization of a novel glycoinositolphospholipid from the parasitic nematode, Ascaris suum

Sugita, Mutsumi; Mizunoma, Tomoko; Aoki, Kazuhiro; Dulaney, John T.; Inagaki, Fuyuhiko; Suzuki, Minoru; Suzuki, Akemi; Ichikawa, Saori; Kushida, Katsuhiko; Ohta, Satoru; Kurimoto, Ayako

doi:10.1016/0005-2760(96)00047-1

Cited by 25 publications

(5 citation statements)

References 35 publications

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“…The sialylated glycosphingolipids, called gangliosides, have been widely distributed within the Echinodermata and in deuterostomes. For example, although gangliosides have not been detected in protostomia, other acidic glycosphingolipids containing uronic acid or inositol phosphate have been characterized (7)(8)(9).…”

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Isolation and characterization of a novel uronic acid-containing acidic glycosphingolipid from the ascidian Halocynthia roretzi

Ito

Matsumuro

Yamada

et al. 2007

Journal of Lipid Research

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A novel uronic acid-containing glycosphingolipid (UGL-1) was isolated from the ascidian Halocynthia roretzi. UGL-1 was prepared from chloroform-methanol extracts and purified by the use of successive column chromatography on DEAE-Sephadex, Florisil, and Iatrobeads. Chemical structural analysis was performed using methylation analysis, gas chromatography, gas chromatography-mass spectrometry, matrix-assisted laser-desorption/ionization time-of-flight mass spectrometry, and 1 H-NMR spectra. The chemical structure of UGL-1 was determined to be a glucuronic acid-containing glycosphingolipid, Galb1-4(Fuca1-3)GlcAb1-1Cer. The ceramide component was composed of C16:0 and C18:0 acids and C 16 -, C 17 -, and C 18 -phytosphingosines as major components. Glycosphingolipids have been characterized in a range of animal phyla, including arthropods, and have been shown to participate in important functions such as cellular development (1-6). Comparison of protostome and deuterostome glycolipids shows dramatic structural differences even between species with closely related glycolipid expression. In particular, the structures of acidic glycolipids are unique. The sialylated glycosphingolipids, called gangliosides, have been widely distributed within the Echinodermata and in deuterostomes. For example, although gangliosides have not been detected in protostomia, other acidic glycosphingolipids containing uronic acid or inositol phosphate have been characterized (7-9).Ascidians, which belong to the phylum Urochordata, are often referred to as protochordates because during the larval stage they possess chordate characteristics, most notably the tail contains a notochord and a dorsal hollow nerve cord. After a free-swimming stage, the simple tadpolelike larvae attach to a substrate and undergo metamorphosis that includes tail loss and rearrangement of the internal organs. Subsequently, in the adult form, the similarities to chordates are lost. In addition, ascidians are good model organisms for understanding vertebrates (and their development) because their cell lineage can be traced (10, 11) and a large number of genome-related data have been accumulated, including genome sequences, expressed sequence tag sequences, and gene expression patterns (12-15). However, very few studies have been directed to ascidian glycolipids, with the exception of some neutral glycolipids (16)(17)(18).In this article, we describe the structural characterization of a novel acidic glycosphingolipid containing a uronic acid residue (UGL-1) from the ascidian Halocynthia roretzi. UGL-1 exhibits unique structural features, such as Galb1-4(Fuca1-3)GlcAb1-1Cer. The chemical structure of UGL-1, which has a uronic acid with a fucosyl residue bond at the reducing end, is the first example to our knowledge. MATERIALS AND METHODS Isolation and purification of acidic glycolipidsSpecimens of H. roretzi were obtained from Hiroyo Fisheries, Ltd., at Miyagi in Japan, and the cellulose crust was removed, Abbreviations: MALDI-TOF MS, matrix-assisted laser-desorp...

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confidence: 99%

Isolation and characterization of a novel uronic acid-containing acidic glycosphingolipid from the ascidian Halocynthia roretzi

Ito

Matsumuro

Yamada

et al. 2007

Journal of Lipid Research

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“…For glycerolipid removal, mild alkali hydrolysis was conducted followed by dialysis of the total lipids (13). For neutral and acidic sphingolipid class separation, DEAE-Sephadex A-25 column chromatography (Pharmacia LKB Biotechnology, Sweden) was carried out on the alkali-stable product as previously reported (14,15).…”

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Content and Constituent Properties of Sphingolipid Classes in Saccharomyces kluyveri

et al. 2006

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Sphingolipids are each comprised of a sphingoid base backbone, amide linked fatty acid (normal and 2hydroxy fatty acids) and a polar headgroup, such as phosphocholine or hexose. These lipids may frequently be found in eukaryotic organisms, with the mammalian sphingolipid trans-4-sphingenine (sphingosine) being most prevalent. Other sphingoid bases such as sphinga-nine (dihydrosphingosine) and 4-hydroxysphinganine (phytosphingosine) are often present in small amounts. Plant and fungal sphingolipids display a diversity of sphingoid base structures, as apparent from trans-8sphingenine, cis-8-sphingenine, trans-4, trans-8-sphingadienine, trans-4, cis-8-sphingadienine, 4-hydroxysphinganine, 4-hydroxy-trans-8-sphingenine, 4hydroxy-trans-8-sphingenine and 9-methyl-trans-4, trans-8-sphingadienine (9-Me d18:2 4t, 8t) (1-4).

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“…Glycolipids, galactosylceramides, and glycosphingolipids have been identified in tegumental membranes of Spirometra mansonoides , Echinococcus multilocularis, and Hymenolepis diminuta [15–17]. A novel glycosphingolipid named AGL containing inositol phosphate as acidic group has been found in the nematode Ascaris sum [18]. …”

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confidence: 99%

Release of Glycoprotein (GP1) from the Tegumental Surface ofTaenia soliumby Phospholipase C fromClostridium perfringensSuggests a Novel Protein-Anchor to Membranes

Landa

Willms

Laclette³

2010

Journal of Biomedicine and Biotechnology

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In order to explore how molecules are linked to the membrane surface in larval Taenia solium, whole cysticerci were incubated in the presence of phospholipase C from Clostridium perfringens (PLC). Released material was collected and analyzed in polyacrylamide gels with sodium dodecyl sulfate. Two major bands with apparent molecular weights of 180 and 43 kDa were observed. Western blot of released material and localization assays in cysticerci tissue sections using antibodies against five known surface glycoproteins of T. solium cysticerci indicated that only one, previously called GP1, was released. Similar localization studies using the lectins wheat-germ-agglutinin and Concanavalin A showed that N-acetyl-D-glucosamine, N-acetylneuraminic, sialic acid, αmethyl-D-mannoside, D-manose/glucose, and N-acetyl-D-glucosamine residues are abundantly present on the surface. On the other hand, we find that treatment with PLC releases molecules from the surface; they do not reveal Cross Reacting Determinant (CRD), suggesting a novel anchor to the membrane for the glycoprotein GP1.

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Structural characterization of a novel glycoinositolphospholipid from the parasitic nematode, Ascaris suum

Cited by 25 publications

References 35 publications

Isolation and characterization of a novel uronic acid-containing acidic glycosphingolipid from the ascidian Halocynthia roretzi

Isolation and characterization of a novel uronic acid-containing acidic glycosphingolipid from the ascidian Halocynthia roretzi

Content and Constituent Properties of Sphingolipid Classes in Saccharomyces kluyveri

Release of Glycoprotein (GP1) from the Tegumental Surface ofTaenia soliumby Phospholipase C fromClostridium perfringensSuggests a Novel Protein-Anchor to Membranes

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