Show legend Show as text

Structure type: oligomer ; 778 [M+Na]+
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_5

• Article ID: 6875
  Duarte RS, Polycarpo CR, Wait R, Hartmann R, Bergter EB "Structural characterization of neutral glycosphingolipids from Fusarium species" - Biochimica et Biophysica Acta 1390 (1998) 186-196
  

  Glycosphingolipids were extracted from hyphae of Fusarium solani and from an unnamed Fusarium species, and were purified by silica and Iatrobead column chromatography. Their structures were determined by compositional analysis, nuclear magnetic resonance spectroscopy, gas chromatography/mass spectrometry and by fast atom bombardment mass spectrometry of the native and peracetylated materials, which defined their sugar, long-chain base and fatty acid compositions. The locations of the double bonds in the bases were established by 2D NMR spectroscopy and by novel mass spectrometric approaches, including collisional activation of the protonated and lithium-cationized glycosphingolipids, and of the sphingadienene-derived fragment ion at m/z 276. From these results we propose that the structures of the glycosphingolipids from F. solani and Fusarium sp. are N-2'-hydroxyoctadecanoyl-1-O-β-D-glucopyranosyl-9-methyl-4, 8-sphingadienine and N-2'-hydroxyoctadecenoyl-1-O-β-D-glucopyranosyl-9-methyl-4, 8-sphingadienine, respectively

  NMR spectroscopy, mass spectrometry, glycosphingolipid, Fast Atom Bombardment, Fusarium

  Journal NLM ID: 0217513
  WWW link: http://www.sciencedirect.com/science/article/pii/S0005276097001793
  Publisher: Elsevier
  Correspondence: immgbel@microbio.ufrj.br
  Institutions: Instituto de Microbiologia, Universidade Federal do Rio de Janeiro, 21 944 970-Cidade Universitária, Rio de Janeiro, RJ, Brazil, Centre for Applied Microbiology and Research, Salisbury, SP4 0JG, UK, Institut für Physiologische Chemie, Universität Bonn, Bonn, Germany
  Methods: 1H NMR, FAB-MS, GC-MS, acid hydrolysis, GLC, GC, paper chromatography, methanolysis, HPTLC, COSY, silica gel chromatography
  
   
  
  Fusarium
  CSDB ID 40840 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: glucosylceramide
Compound class: glycolipid
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_5

• Article ID: 7002
  Park C, Bennion B, Francois IEJA, Ferket KKA, Cammue BPA, Thevissen K, Levery SB "Neutral glycolipids of the filamentous fungus Neurospora crassa: altered expression in plant defensin-resistant mutants" - Journal of Lipid Research 46(4) (2005) 759-768
  

  To defend themselves against fungal pathogens, plants produce numerous antifungal proteins and peptides, including defensins, some of which have been proposed to interact with fungal cell surface glycosphingolipid components. Although not known as a phytopathogen, the filamentous fungus Neurospora crassa possesses numerous genes similar to those required for plant pathogenesis identified in fungal pathogens (Galagan, J. E., et al. 2003. Nature 422: 859-868), and it has been used as a model for studying plant-phytopathogen interactions targeting fungal membrane components (Thevissen, K., et al. 2003. Peptides. 24: 1705 1712). For this study, neutral glycolipid components were extracted from wild-type and plant defensin-resistant mutant strains of N. crassa. The structures of purified components were elucidated by NMR spectroscopy and mass spectrometry. Neutral glycosphingolipids of both wild-type and mutant strains were characterized as β-glucopyranosylceramides, but those of the mutants were found with structurally altered ceramides. Although the wild type expressed a preponderance of N-2'-hydroxy-(E)-Delta(3)-octadecenoate as the fatty-N-acyl component attached to the long-chain base (4E,8E)-9-methyl-4,8-sphingadienine, the mutant ceramides were found with mainly N-2'-hydroxyhexadecanoate instead. In addition, the mutant strains expressed highly increased levels of a sterol glucoside identified as ergosterol-β-glucoside. The potential implications of these findings with respect to defensin resistance in the N. crassa mutants are discussed.

  mass spectrometry, nuclear magnetic resonance spectroscopy, ceramide, tandem mass spectrometry, Electrospray Ionization, collision-induced dissociation, glucoside, Aspergillus fumigatus, sphingolipid, cerebroside, ergosterol, sterol

  NCBI PubMed ID: 15654124
  Publication DOI: 10.1194/jlr.M400457-JLR200
  Journal NLM ID: 0376606
  Publisher: ASBMB
  Correspondence: slevery@cisunix.unh.edu
  Institutions: Department of Chemistry, University of New Hampshire, Durham, NH 03824-3598, Complex Carbohydrate Research Center and Department of Biochemistry and Molecular Biology, University of Georgia, Athens, GA 30602-7229, Center of Microbial and Plant Genetics, Katholieke Universiteit Leuven, B-3001 Heverlee-Leuven, Belgium
  Methods: 13C NMR, 1H NMR, NMR-2D, ESI-MS, ion-exchange chromatography, extraction, HPTLC, ESI-QTOF-MS
  
   
  
  Neurospora crassa 74-OR23-1A
  CSDB ID 41270 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: glucosylceramide
Compound class: glycolipid
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141794,IEDB_190606,SB_1,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88

• Article ID: 7002
  Park C, Bennion B, Francois IEJA, Ferket KKA, Cammue BPA, Thevissen K, Levery SB "Neutral glycolipids of the filamentous fungus Neurospora crassa: altered expression in plant defensin-resistant mutants" - Journal of Lipid Research 46(4) (2005) 759-768
  

  To defend themselves against fungal pathogens, plants produce numerous antifungal proteins and peptides, including defensins, some of which have been proposed to interact with fungal cell surface glycosphingolipid components. Although not known as a phytopathogen, the filamentous fungus Neurospora crassa possesses numerous genes similar to those required for plant pathogenesis identified in fungal pathogens (Galagan, J. E., et al. 2003. Nature 422: 859-868), and it has been used as a model for studying plant-phytopathogen interactions targeting fungal membrane components (Thevissen, K., et al. 2003. Peptides. 24: 1705 1712). For this study, neutral glycolipid components were extracted from wild-type and plant defensin-resistant mutant strains of N. crassa. The structures of purified components were elucidated by NMR spectroscopy and mass spectrometry. Neutral glycosphingolipids of both wild-type and mutant strains were characterized as β-glucopyranosylceramides, but those of the mutants were found with structurally altered ceramides. Although the wild type expressed a preponderance of N-2'-hydroxy-(E)-Delta(3)-octadecenoate as the fatty-N-acyl component attached to the long-chain base (4E,8E)-9-methyl-4,8-sphingadienine, the mutant ceramides were found with mainly N-2'-hydroxyhexadecanoate instead. In addition, the mutant strains expressed highly increased levels of a sterol glucoside identified as ergosterol-β-glucoside. The potential implications of these findings with respect to defensin resistance in the N. crassa mutants are discussed.

  mass spectrometry, nuclear magnetic resonance spectroscopy, ceramide, tandem mass spectrometry, Electrospray Ionization, collision-induced dissociation, glucoside, Aspergillus fumigatus, sphingolipid, cerebroside, ergosterol, sterol

  NCBI PubMed ID: 15654124
  Publication DOI: 10.1194/jlr.M400457-JLR200
  Journal NLM ID: 0376606
  Publisher: ASBMB
  Correspondence: slevery@cisunix.unh.edu
  Institutions: Department of Chemistry, University of New Hampshire, Durham, NH 03824-3598, Complex Carbohydrate Research Center and Department of Biochemistry and Molecular Biology, University of Georgia, Athens, GA 30602-7229, Center of Microbial and Plant Genetics, Katholieke Universiteit Leuven, B-3001 Heverlee-Leuven, Belgium
  Methods: 13C NMR, 1H NMR, NMR-2D, ESI-MS, ion-exchange chromatography, extraction, HPTLC, ESI-QTOF-MS
  
   
  
  Neurospora crassa 74-OR23-1A
  CSDB ID 41384 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: glucosylceramide
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_5

• Article ID: 7020
  da Silva AFC, Rodrigues ML, Farias SE, Almeida IC, Pinto MR, Barreto-Bergter E "Glucosylceramides in Colletotrichum gloeosporioides are involved in the differentiation of conidia into mycelial cells" - FEBS Letters 561(1-3) (2004) 137-143
  

  Glucosylceramides (GlcCer) were extracted from the plant pathogen Colletotrichum gloeosporioides and purified by several chromatographic steps. By using electrospray ionization mass spectrometry and nuclear magnetic resonance, GlcCer from C. gloeosporioides were identified as N-2'-hydroxyoctadecanoyl-1-β-D-glucopyranosyl-9-methyl-4,8-sphingadienine and N-2'-hydroxyoctadecenoyl-1-β-D-glucopyranosyl-9-methyl-4,8-sphingadienine. Monoclonal antibodies against these structures were produced and used as tools for the evaluation of the role of GlcCer in the morphological transition of C. gloeosporioides. In the presence of antibodies to GlcCer, the differentiation of conidia into mycelia was blocked. Since GlcCer is present in several plant pathogens, the inhibitory activity of external ligands recognizing these structures mail be applicable in other models of fungal infections.

  glucosylceramide, monoclonal antibody to GlcCe, Colletotrichum gloeosporioides

  Publication DOI: 10.1016/S0014-5793(04)00156-5
  Journal NLM ID: 0155157
  Publisher: Elsevier
  Correspondence: eliana.bergter@micro.ufrj.br
  Institutions: Instituto de Microbiologia Professor Paulo de Góes, Universidade Federal do Rio de Janeiro, Centro de Ciências da Saúde, Bloco I, Cidade Universitária, Rio de Janeiro 21941-590, Brazil, Departamento de Fisiologia, Instituto de Ciências Básicas da Saúde, Universidade Federal do Rio Grande do Sul, Porto Alegre, Brazil, Departamento de Parasitologia, Universidade de São Paulo, São Paulo, Brazil
  Methods: 1H NMR, GC-MS, sugar analysis, TLC, ELISA, ESI-MS, acid hydrolysis, ESI-MS/MS, biological assays, serological methods, extraction, HPTLC, immunofluorescence analyses
  
   
  
  Colletotrichum gloeosporioides
  CSDB ID 41322 (all data & tools)

Show legend Show as text

Structure type: monomer
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192,SB_5

• Article ID: 7065
  Takahashi HK, Toledo MS, Suzuki E, Tagliari L, Straus AH "Current relevance of fungal and trypanosomatid glycolipids and sphingolipids: studies defining structures conspicuously absent in mammals" - Anais Da Academia Brasileira De Ciências 81(3) (2009) 477-488
  

  Recently, glycosphingolipids have been attracting attention due to their role on biological systems as second messengers or modulators of signal transduction, affecting several events, which range from apoptosis to regulation of the cell cycle. In pathogenic fungi, glycolipids are expressed in two classes: neutral monohexosylceramides (glucosyl-or galactosylceramide) and acidic glycosylinositol phosphorylceramides (the latter class carries longer glycan chains). It is worth to mention that monohexosylceramides exhibit significant structural differences in their lipid moieties compared to their mammalian counterparts, whereas the glycosylinositol phosphorylceramides exhibit remarkable structural differences in their carbohydrate moieties in comparison to mammal glycosphingolipids counterpart. We observed that glycosylinositol phosphorylceramides are capable of promoting immune response in infected humans. In addition, inhibiting fungal glycosphingolipid biosynthetic pathways leads to an inhibition of colony formation, spore germination, cell cycle, dimorphism and hyphal growth. Other pathogens, such as trypanosomatids, also present unique glycolipids, which may have an important role for the parasite development and/or disease establishment. Regarding host-pathogen interaction, cell membrane rafts, which are enriched in sphingolipids and sterols, participate in parasite/fungal infection. In this review, it is discussed the different biological roles of (glyco) (sphingo)lipids of pathogenic/opportunistic fungi and trypanosomatids.

  glycosphingolipids, leishmania, glycosylinositol phosphorylceramides, inositol phosphorylceramide, membrane rafts, pathogenic fungi

  NCBI PubMed ID: 19722017
  Publication DOI: 10.1590/S0001-37652009000300012
  Journal NLM ID: 7503280
  Publisher: Academia Brasileira De Ciencias
  Correspondence: Anita H. Straus
  Institutions: Setor de Imunoquímica de Glicoconjugados, Departamento de Bioquímica Ed. J.L. Prado, São Paulo, Brasil, Departamento de Microbiologia, Imunologia e Parasitologia, São Paulo, Brasil
  
   
  
  Paracoccidioides brasiliensis, Histoplasma capsulatum, Aspergillus fumigatus, Sporothrix schenckii, Aspergillus nidulans, Candida, Cryptococcus
  CSDB ID 41731 (all data & tools)

Show legend Show as text

Structure type: monomer ; 1002.6 (h18:0), 1058.7 (h22:0), 1084.7 (h24:1), 1086.7 (h24:0) [M-H]-
Trivial name: glycosylinositolphospholipid
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_130701,IEDB_1394182,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_67,SB_72

• Article ID: 7092
  Itonori S, Yamawaki S, Aoki K, Yamamoto K, Hada N, Takeda T, Dulaney JT, Sugita M "Structural characterization of glycosylinositolphospholipids with a blood group type B sugar unit from the edible mushroom, Hypsizygus marmoreus" - Glycobiology 18(7) (2008) 540-548
  

  Edible fungi, mushrooms, are a popular food in Japan and over 15 cultured mushroom species are available at the food markets. Recently, constituents or ingredients of edible mushrooms have drawn attention because possibilities have been seen for their medical usage. Mycoglycolipids (basidiolipids) of higher mushrooms have been characterized as glycosylinositolphosphoceramides, having a common core structure of Manα1-2Ins1-[PO(4)]-Cer and extensions of Man, Gal, and/or Fuc sugar moieties. Seven mycoglycolipids were purified from the edible mushroom Hypsizygus marmoreus by successive column chromatography on ion exchange Sephadex (DEAE-Sephadex) and silicic acid (Iatrobeads). Their structures were characterized to be Ins1-[PO(4)]-Cer (AGL0), Manα1-2Ins1-[PO(4)]-Cer (AGL1), Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL2), Fucα1- 2Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL3), Galα1-3(Fucα1-2)Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL4), Galα1-2Galα1-3(Fucα1-2)Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL5), and Galα1-2Galα1-2Galα1-3(Fucα1-2)Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL6) by sugar compositional analysis, methylation analysis, periodate oxidation, partial acid hydrolysis, enzymatic hydrolysis, immunochemical analysis, gas-liquid chromatography (GC), gas chromatography-mass spectrometry (GC-MS), matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS), and (1)H-nuclear magnetic resonance spectroscopy (NMR). Ceramide constituents of their mycoglycolipids were composed of phytosphingosine as the sole sphingoid, and mainly 2-hydroxy C22:0 and C24:0 acids as the fatty acids. By immunochemical detection, the terminal structure of AGL4, Galα1-3(Fucα1-2)Galβ-, was shown to have blood group type B activity. Galα1-2 and its repeating sequence in AGL5 and AGL6 are novel structures on the nonreducing sugar end in mycoglycolipids. These two mycoglycolipids in H. marmoreus distinguish it from other basidiomycetes.

  mushroom, glycosphingolipid, blood group, Hypsizygus marmoreus, mycoglycolipid

  NCBI PubMed ID: 18450973
  Publication DOI: 10.1093/glycob/cwn036
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Correspondence: Saki Itonori
  Institutions: Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University, Otsu, Japan
  Methods: 1H NMR, methylation, periodate oxidation, partial acid hydrolysis, GC-MS, sugar analysis, TLC, GC, MALDI-TOF MS, composition analysis, alkaline hydrolysis, enzymatic digestion, ion-exchange chromatography, extraction, HF treatment, CC, TLC immunostaining
  
   
  
  Hypsizygus marmoreus
  CSDB ID 41764 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1136.6 (h16:0), 1164.6 (h18:0), 1192.7 (h20:0), 1220.7 (h22:0), 1246.7 (h24:1), 1248.7 (h24:0) [M-H]-
Trivial name: glycosylinositolphospholipid
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_130701,IEDB_136044,IEDB_136095,IEDB_137472,IEDB_1394182,IEDB_141794,IEDB_144983,IEDB_152206,IEDB_190606,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88

• Article ID: 7092
  Itonori S, Yamawaki S, Aoki K, Yamamoto K, Hada N, Takeda T, Dulaney JT, Sugita M "Structural characterization of glycosylinositolphospholipids with a blood group type B sugar unit from the edible mushroom, Hypsizygus marmoreus" - Glycobiology 18(7) (2008) 540-548
  

  Edible fungi, mushrooms, are a popular food in Japan and over 15 cultured mushroom species are available at the food markets. Recently, constituents or ingredients of edible mushrooms have drawn attention because possibilities have been seen for their medical usage. Mycoglycolipids (basidiolipids) of higher mushrooms have been characterized as glycosylinositolphosphoceramides, having a common core structure of Manα1-2Ins1-[PO(4)]-Cer and extensions of Man, Gal, and/or Fuc sugar moieties. Seven mycoglycolipids were purified from the edible mushroom Hypsizygus marmoreus by successive column chromatography on ion exchange Sephadex (DEAE-Sephadex) and silicic acid (Iatrobeads). Their structures were characterized to be Ins1-[PO(4)]-Cer (AGL0), Manα1-2Ins1-[PO(4)]-Cer (AGL1), Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL2), Fucα1- 2Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL3), Galα1-3(Fucα1-2)Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL4), Galα1-2Galα1-3(Fucα1-2)Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL5), and Galα1-2Galα1-2Galα1-3(Fucα1-2)Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL6) by sugar compositional analysis, methylation analysis, periodate oxidation, partial acid hydrolysis, enzymatic hydrolysis, immunochemical analysis, gas-liquid chromatography (GC), gas chromatography-mass spectrometry (GC-MS), matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS), and (1)H-nuclear magnetic resonance spectroscopy (NMR). Ceramide constituents of their mycoglycolipids were composed of phytosphingosine as the sole sphingoid, and mainly 2-hydroxy C22:0 and C24:0 acids as the fatty acids. By immunochemical detection, the terminal structure of AGL4, Galα1-3(Fucα1-2)Galβ-, was shown to have blood group type B activity. Galα1-2 and its repeating sequence in AGL5 and AGL6 are novel structures on the nonreducing sugar end in mycoglycolipids. These two mycoglycolipids in H. marmoreus distinguish it from other basidiomycetes.

  mushroom, glycosphingolipid, blood group, Hypsizygus marmoreus, mycoglycolipid

  NCBI PubMed ID: 18450973
  Publication DOI: 10.1093/glycob/cwn036
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Correspondence: Saki Itonori
  Institutions: Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University, Otsu, Japan
  Methods: 1H NMR, methylation, periodate oxidation, partial acid hydrolysis, GC-MS, sugar analysis, TLC, GC, MALDI-TOF MS, composition analysis, alkaline hydrolysis, enzymatic digestion, ion-exchange chromatography, extraction, HF treatment, CC, TLC immunostaining
  
   
  
  Hypsizygus marmoreus
  CSDB ID 41974 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1310.6 (h18:0), 1366.6 (h20:0), 1394.7 (h24:0) [M-H]-
Trivial name: glycosylinositolphospholipid
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_115015,IEDB_130701,IEDB_136044,IEDB_136045,IEDB_136095,IEDB_137472,IEDB_1394182,IEDB_141794,IEDB_142489,IEDB_144562,IEDB_144983,IEDB_149135,IEDB_150948,IEDB_152206,IEDB_152214,IEDB_153553,IEDB_174333,IEDB_190606,IEDB_461719,IEDB_983930,SB_154,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_86,SB_88

• Article ID: 7092
  Itonori S, Yamawaki S, Aoki K, Yamamoto K, Hada N, Takeda T, Dulaney JT, Sugita M "Structural characterization of glycosylinositolphospholipids with a blood group type B sugar unit from the edible mushroom, Hypsizygus marmoreus" - Glycobiology 18(7) (2008) 540-548
  

  Edible fungi, mushrooms, are a popular food in Japan and over 15 cultured mushroom species are available at the food markets. Recently, constituents or ingredients of edible mushrooms have drawn attention because possibilities have been seen for their medical usage. Mycoglycolipids (basidiolipids) of higher mushrooms have been characterized as glycosylinositolphosphoceramides, having a common core structure of Manα1-2Ins1-[PO(4)]-Cer and extensions of Man, Gal, and/or Fuc sugar moieties. Seven mycoglycolipids were purified from the edible mushroom Hypsizygus marmoreus by successive column chromatography on ion exchange Sephadex (DEAE-Sephadex) and silicic acid (Iatrobeads). Their structures were characterized to be Ins1-[PO(4)]-Cer (AGL0), Manα1-2Ins1-[PO(4)]-Cer (AGL1), Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL2), Fucα1- 2Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL3), Galα1-3(Fucα1-2)Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL4), Galα1-2Galα1-3(Fucα1-2)Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL5), and Galα1-2Galα1-2Galα1-3(Fucα1-2)Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL6) by sugar compositional analysis, methylation analysis, periodate oxidation, partial acid hydrolysis, enzymatic hydrolysis, immunochemical analysis, gas-liquid chromatography (GC), gas chromatography-mass spectrometry (GC-MS), matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS), and (1)H-nuclear magnetic resonance spectroscopy (NMR). Ceramide constituents of their mycoglycolipids were composed of phytosphingosine as the sole sphingoid, and mainly 2-hydroxy C22:0 and C24:0 acids as the fatty acids. By immunochemical detection, the terminal structure of AGL4, Galα1-3(Fucα1-2)Galβ-, was shown to have blood group type B activity. Galα1-2 and its repeating sequence in AGL5 and AGL6 are novel structures on the nonreducing sugar end in mycoglycolipids. These two mycoglycolipids in H. marmoreus distinguish it from other basidiomycetes.

  mushroom, glycosphingolipid, blood group, Hypsizygus marmoreus, mycoglycolipid

  NCBI PubMed ID: 18450973
  Publication DOI: 10.1093/glycob/cwn036
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Correspondence: Saki Itonori
  Institutions: Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University, Otsu, Japan
  Methods: 1H NMR, methylation, periodate oxidation, partial acid hydrolysis, GC-MS, sugar analysis, TLC, GC, MALDI-TOF MS, composition analysis, alkaline hydrolysis, enzymatic digestion, ion-exchange chromatography, extraction, HF treatment, CC, TLC immunostaining
  
   
  
  Hypsizygus marmoreus
  CSDB ID 41975 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1472.4 (h18:0), 1528.5 (h22:0), 1554.5 (h24:1), 1556.5 (h24:0) [M-H]-
Trivial name: glycosylinositolphospholipid
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_115013,IEDB_115015,IEDB_130645,IEDB_130701,IEDB_136044,IEDB_136045,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_1394182,IEDB_140125,IEDB_141794,IEDB_142489,IEDB_144562,IEDB_144983,IEDB_149135,IEDB_149558,IEDB_150948,IEDB_151528,IEDB_152206,IEDB_152212,IEDB_152214,IEDB_153553,IEDB_174333,IEDB_190606,IEDB_461719,IEDB_918314,IEDB_983930,SB_148,SB_154,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_86,SB_87,SB_88

• Article ID: 7092
  Itonori S, Yamawaki S, Aoki K, Yamamoto K, Hada N, Takeda T, Dulaney JT, Sugita M "Structural characterization of glycosylinositolphospholipids with a blood group type B sugar unit from the edible mushroom, Hypsizygus marmoreus" - Glycobiology 18(7) (2008) 540-548
  

  Edible fungi, mushrooms, are a popular food in Japan and over 15 cultured mushroom species are available at the food markets. Recently, constituents or ingredients of edible mushrooms have drawn attention because possibilities have been seen for their medical usage. Mycoglycolipids (basidiolipids) of higher mushrooms have been characterized as glycosylinositolphosphoceramides, having a common core structure of Manα1-2Ins1-[PO(4)]-Cer and extensions of Man, Gal, and/or Fuc sugar moieties. Seven mycoglycolipids were purified from the edible mushroom Hypsizygus marmoreus by successive column chromatography on ion exchange Sephadex (DEAE-Sephadex) and silicic acid (Iatrobeads). Their structures were characterized to be Ins1-[PO(4)]-Cer (AGL0), Manα1-2Ins1-[PO(4)]-Cer (AGL1), Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL2), Fucα1- 2Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL3), Galα1-3(Fucα1-2)Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL4), Galα1-2Galα1-3(Fucα1-2)Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL5), and Galα1-2Galα1-2Galα1-3(Fucα1-2)Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL6) by sugar compositional analysis, methylation analysis, periodate oxidation, partial acid hydrolysis, enzymatic hydrolysis, immunochemical analysis, gas-liquid chromatography (GC), gas chromatography-mass spectrometry (GC-MS), matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS), and (1)H-nuclear magnetic resonance spectroscopy (NMR). Ceramide constituents of their mycoglycolipids were composed of phytosphingosine as the sole sphingoid, and mainly 2-hydroxy C22:0 and C24:0 acids as the fatty acids. By immunochemical detection, the terminal structure of AGL4, Galα1-3(Fucα1-2)Galβ-, was shown to have blood group type B activity. Galα1-2 and its repeating sequence in AGL5 and AGL6 are novel structures on the nonreducing sugar end in mycoglycolipids. These two mycoglycolipids in H. marmoreus distinguish it from other basidiomycetes.

  mushroom, glycosphingolipid, blood group, Hypsizygus marmoreus, mycoglycolipid

  NCBI PubMed ID: 18450973
  Publication DOI: 10.1093/glycob/cwn036
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Correspondence: Saki Itonori
  Institutions: Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University, Otsu, Japan
  Methods: 1H NMR, methylation, periodate oxidation, partial acid hydrolysis, GC-MS, sugar analysis, TLC, GC, MALDI-TOF MS, composition analysis, alkaline hydrolysis, enzymatic digestion, ion-exchange chromatography, extraction, HF treatment, CC, TLC immunostaining
  
   
  
  Hypsizygus marmoreus, Amanita virosa
  CSDB ID 41976 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1635.0 (h18:0), 1691.0 (h22:0), 1717.0 (h24:1), 1719.1 (h24:0) [M-H]-
Trivial name: glycosylinositolphospholipid
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_115013,IEDB_115015,IEDB_130645,IEDB_130701,IEDB_131186,IEDB_135818,IEDB_136044,IEDB_136045,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_1394182,IEDB_140125,IEDB_141794,IEDB_142489,IEDB_144562,IEDB_144983,IEDB_149135,IEDB_149558,IEDB_150948,IEDB_151528,IEDB_152206,IEDB_152212,IEDB_152214,IEDB_153553,IEDB_174333,IEDB_190606,IEDB_461719,IEDB_918314,IEDB_983930,SB_148,SB_154,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_86,SB_87,SB_88

• Article ID: 7092
  Itonori S, Yamawaki S, Aoki K, Yamamoto K, Hada N, Takeda T, Dulaney JT, Sugita M "Structural characterization of glycosylinositolphospholipids with a blood group type B sugar unit from the edible mushroom, Hypsizygus marmoreus" - Glycobiology 18(7) (2008) 540-548
  

  Edible fungi, mushrooms, are a popular food in Japan and over 15 cultured mushroom species are available at the food markets. Recently, constituents or ingredients of edible mushrooms have drawn attention because possibilities have been seen for their medical usage. Mycoglycolipids (basidiolipids) of higher mushrooms have been characterized as glycosylinositolphosphoceramides, having a common core structure of Manα1-2Ins1-[PO(4)]-Cer and extensions of Man, Gal, and/or Fuc sugar moieties. Seven mycoglycolipids were purified from the edible mushroom Hypsizygus marmoreus by successive column chromatography on ion exchange Sephadex (DEAE-Sephadex) and silicic acid (Iatrobeads). Their structures were characterized to be Ins1-[PO(4)]-Cer (AGL0), Manα1-2Ins1-[PO(4)]-Cer (AGL1), Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL2), Fucα1- 2Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL3), Galα1-3(Fucα1-2)Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL4), Galα1-2Galα1-3(Fucα1-2)Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL5), and Galα1-2Galα1-2Galα1-3(Fucα1-2)Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL6) by sugar compositional analysis, methylation analysis, periodate oxidation, partial acid hydrolysis, enzymatic hydrolysis, immunochemical analysis, gas-liquid chromatography (GC), gas chromatography-mass spectrometry (GC-MS), matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS), and (1)H-nuclear magnetic resonance spectroscopy (NMR). Ceramide constituents of their mycoglycolipids were composed of phytosphingosine as the sole sphingoid, and mainly 2-hydroxy C22:0 and C24:0 acids as the fatty acids. By immunochemical detection, the terminal structure of AGL4, Galα1-3(Fucα1-2)Galβ-, was shown to have blood group type B activity. Galα1-2 and its repeating sequence in AGL5 and AGL6 are novel structures on the nonreducing sugar end in mycoglycolipids. These two mycoglycolipids in H. marmoreus distinguish it from other basidiomycetes.

  mushroom, glycosphingolipid, blood group, Hypsizygus marmoreus, mycoglycolipid

  NCBI PubMed ID: 18450973
  Publication DOI: 10.1093/glycob/cwn036
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Correspondence: Saki Itonori
  Institutions: Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University, Otsu, Japan
  Methods: 1H NMR, methylation, periodate oxidation, partial acid hydrolysis, GC-MS, sugar analysis, TLC, GC, MALDI-TOF MS, composition analysis, alkaline hydrolysis, enzymatic digestion, ion-exchange chromatography, extraction, HF treatment, CC, TLC immunostaining
  
   
  
  Hypsizygus marmoreus
  CSDB ID 41977 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1768.9 (h16:0), 1796.9 (h18:0), 1853.2 (h22:0), 1881.1 (h24:0) [M-H]-
Trivial name: glycosylinositolphospholipid
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_115013,IEDB_115015,IEDB_130645,IEDB_130701,IEDB_131186,IEDB_135818,IEDB_136044,IEDB_136045,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_1394182,IEDB_140125,IEDB_141794,IEDB_142489,IEDB_144562,IEDB_144983,IEDB_149135,IEDB_149558,IEDB_150948,IEDB_151528,IEDB_152206,IEDB_152212,IEDB_152214,IEDB_153553,IEDB_174333,IEDB_190606,IEDB_461719,IEDB_918314,IEDB_983930,SB_148,SB_154,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_86,SB_87,SB_88

• Article ID: 7092
  Itonori S, Yamawaki S, Aoki K, Yamamoto K, Hada N, Takeda T, Dulaney JT, Sugita M "Structural characterization of glycosylinositolphospholipids with a blood group type B sugar unit from the edible mushroom, Hypsizygus marmoreus" - Glycobiology 18(7) (2008) 540-548
  

  Edible fungi, mushrooms, are a popular food in Japan and over 15 cultured mushroom species are available at the food markets. Recently, constituents or ingredients of edible mushrooms have drawn attention because possibilities have been seen for their medical usage. Mycoglycolipids (basidiolipids) of higher mushrooms have been characterized as glycosylinositolphosphoceramides, having a common core structure of Manα1-2Ins1-[PO(4)]-Cer and extensions of Man, Gal, and/or Fuc sugar moieties. Seven mycoglycolipids were purified from the edible mushroom Hypsizygus marmoreus by successive column chromatography on ion exchange Sephadex (DEAE-Sephadex) and silicic acid (Iatrobeads). Their structures were characterized to be Ins1-[PO(4)]-Cer (AGL0), Manα1-2Ins1-[PO(4)]-Cer (AGL1), Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL2), Fucα1- 2Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL3), Galα1-3(Fucα1-2)Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL4), Galα1-2Galα1-3(Fucα1-2)Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL5), and Galα1-2Galα1-2Galα1-3(Fucα1-2)Galβ1-6Manα1-2Ins1-[PO(4)]-Cer (AGL6) by sugar compositional analysis, methylation analysis, periodate oxidation, partial acid hydrolysis, enzymatic hydrolysis, immunochemical analysis, gas-liquid chromatography (GC), gas chromatography-mass spectrometry (GC-MS), matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS), and (1)H-nuclear magnetic resonance spectroscopy (NMR). Ceramide constituents of their mycoglycolipids were composed of phytosphingosine as the sole sphingoid, and mainly 2-hydroxy C22:0 and C24:0 acids as the fatty acids. By immunochemical detection, the terminal structure of AGL4, Galα1-3(Fucα1-2)Galβ-, was shown to have blood group type B activity. Galα1-2 and its repeating sequence in AGL5 and AGL6 are novel structures on the nonreducing sugar end in mycoglycolipids. These two mycoglycolipids in H. marmoreus distinguish it from other basidiomycetes.

  mushroom, glycosphingolipid, blood group, Hypsizygus marmoreus, mycoglycolipid

  NCBI PubMed ID: 18450973
  Publication DOI: 10.1093/glycob/cwn036
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Correspondence: Saki Itonori
  Institutions: Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University, Otsu, Japan
  Methods: 1H NMR, methylation, periodate oxidation, partial acid hydrolysis, GC-MS, sugar analysis, TLC, GC, MALDI-TOF MS, composition analysis, alkaline hydrolysis, enzymatic digestion, ion-exchange chromatography, extraction, HF treatment, CC, TLC immunostaining
  
   
  
  Hypsizygus marmoreus
  CSDB ID 41978 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: galactosylceramide
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141794,IEDB_190606,SB_1,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88

• Article ID: 7214
  Barreto-Bergter E, Sassaki GL, de Souza LM "Structural analysis of fungal cerebrosides" - Frontiers in Microbiology 2 (2011) 1-11
  

  Of the ceramide monohexosides (CMHs), gluco- and galactosyl-ceramides are the main neutral glycosphingolipids expressed in fungal cells. Their structural determination is greatly dependent on the use of mass spectrometric techniques, including fast atom bombardment-mass spectrometry, electrospray ionization, and energy collision-induced dissociation mass spectrometry. Nuclear magnetic resonance has also been used successfully. Such a combination of techniques, combined with classical analytical separation, such as high-performance thin layer chromatography and column chromatography, has led to the structural elucidation of a great number of fungal CMHs. The structure of fungal CMH is conserved among fungal species and consists of a glucose or galactose residue attached to a ceramide moiety containing 9-methyl-4,8-sphingadienine with an amidic linkage to hydroxylated fatty acids, most commonly having 16 or 18 carbon atoms and unsaturation between C-3 and C-4. Along with their unique structural characteristics, fungal CMHs have a peculiar subcellular distribution and striking biological properties. Fungal cerebrosides were also characterized as antigenic molecules directly or indirectly involved in cell growth or differentiation in Schizophyllum commune, Cryptococcus neoformans, Pseudallescheria boydii, Candida albicans, Aspergillus nidulans, Aspergillus fumigatus, and Colletotrichum gloeosporioides. Besides classical techniques for cerebroside (CMH) analysis, we now describe new approaches, combining conventional thin layer chromatography and mass spectrometry, as well as emerging technologies for subcellular localization and distribution of glycosphingolipids by secondary ion mass spectrometry and imaging matrix-assisted laser desorption ionization time-of-flight.

  NMR spectroscopy, mass spectrometry, Structural characterization, cerebrosides, pathogenic fungi

  NCBI PubMed ID: 22164155
  Publication DOI: 10.3389/fmicb.2011.00239
  Journal NLM ID: 101548977
  Publisher: Lausanne: Frontiers Research Foundation
  Correspondence: eliana.bergter@micro.ufrj.br
  Institutions: Instituto de Microbiologia Paulo de Góes, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil, Departamento de Bioquímica e Biologia Celular, Universidade Federal do Paraná, Curitiba, Brazil
  Methods: 13C NMR, 1H NMR, NMR-2D, IR, FAB-MS, GC-MS, TLC, ESI-MS, NMR-1D, extraction, CID-MS, HPTLC, SIMS, HPTLC immunostaining, MALDI
  
   
  
  Aspergillus fumigatus, Hansenula anomala, Neurospora crassa
  CSDB ID 43402 (all data & tools)

Show legend Show as text

Structure type: monomer ; 726 [M-H]-, 754 [M-H]-, 756 [M+H]+
Trivial name: glucoceramide
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_5

• Article ID: 7214
  Barreto-Bergter E, Sassaki GL, de Souza LM "Structural analysis of fungal cerebrosides" - Frontiers in Microbiology 2 (2011) 1-11
  

  Of the ceramide monohexosides (CMHs), gluco- and galactosyl-ceramides are the main neutral glycosphingolipids expressed in fungal cells. Their structural determination is greatly dependent on the use of mass spectrometric techniques, including fast atom bombardment-mass spectrometry, electrospray ionization, and energy collision-induced dissociation mass spectrometry. Nuclear magnetic resonance has also been used successfully. Such a combination of techniques, combined with classical analytical separation, such as high-performance thin layer chromatography and column chromatography, has led to the structural elucidation of a great number of fungal CMHs. The structure of fungal CMH is conserved among fungal species and consists of a glucose or galactose residue attached to a ceramide moiety containing 9-methyl-4,8-sphingadienine with an amidic linkage to hydroxylated fatty acids, most commonly having 16 or 18 carbon atoms and unsaturation between C-3 and C-4. Along with their unique structural characteristics, fungal CMHs have a peculiar subcellular distribution and striking biological properties. Fungal cerebrosides were also characterized as antigenic molecules directly or indirectly involved in cell growth or differentiation in Schizophyllum commune, Cryptococcus neoformans, Pseudallescheria boydii, Candida albicans, Aspergillus nidulans, Aspergillus fumigatus, and Colletotrichum gloeosporioides. Besides classical techniques for cerebroside (CMH) analysis, we now describe new approaches, combining conventional thin layer chromatography and mass spectrometry, as well as emerging technologies for subcellular localization and distribution of glycosphingolipids by secondary ion mass spectrometry and imaging matrix-assisted laser desorption ionization time-of-flight.

  NMR spectroscopy, mass spectrometry, Structural characterization, cerebrosides, pathogenic fungi

  NCBI PubMed ID: 22164155
  Publication DOI: 10.3389/fmicb.2011.00239
  Journal NLM ID: 101548977
  Publisher: Lausanne: Frontiers Research Foundation
  Correspondence: eliana.bergter@micro.ufrj.br
  Institutions: Instituto de Microbiologia Paulo de Góes, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil, Departamento de Bioquímica e Biologia Celular, Universidade Federal do Paraná, Curitiba, Brazil
  Methods: 13C NMR, 1H NMR, NMR-2D, IR, FAB-MS, GC-MS, TLC, ESI-MS, NMR-1D, extraction, CID-MS, HPTLC, SIMS, HPTLC immunostaining, MALDI
  
   
  
  Pseudallescheria boydii, Colletotrichum gloeosporioides, Scedosporium apiospermum, Fusarium oxysporum
  CSDB ID 43403 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: ceramide monohexoside
Compound class: glycosphingolipid, cerebroside
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_5,SB_61

• Article ID: 7225
  Pinto MR, Rodrigues ML, Travassos LR, Haido RM, Wait R, Barreto-Bergter E "Characterization of glucosylceramides in Pseudallescheria boydii and their involvement in fungal differentiation" - Glycobiology 12(4) (2002) 251-260
  

  Pseudallescheria boydii is a fungal pathogen that causes disease in immunocompromised patients. Ceramide monohexosides (CMHs) were purified from lipidic extracts of this fungus, showing that, as described for several other species, P. boydii synthesizes glucosylceramides as major neutral glycosphingolipids. CMHs from P. boydii were analyzed by high-performance thin-layer chromatography, gas chromatography coupled to mass spectrometry, fast atom bombardment-mass spectrometry, and nuclear magnetic resonance. These combination of techniques allowed the identification of CMHs from P. boydii as molecules containing a glucose residue attached to 9-methyl-4,8-sphingadienine in amidic linkage to 2-hydroxyoctadecanoic or 2-hydroxyhexadecanoic acids. Antibodies from a rabbit infected with P. boydii recognized CMHs from this fungus. Antibodies to CMH were purified from serum and used in indirect immunofluorescence, which revealed that CMHs are detectable on the surface of mycelial and pseudohyphal but not conidial forms of P. boydii, suggesting a differential expression of glucosylceramides according with morphological phase. We also investigated the influence of antibodies to CMH on growth and germ tube formation in P. boydii. Cultures that were supplemented with these antibodies failed to form mycelium, but the latter was not affected once formed. Similar experiments were performed to evaluate whether antibodies to CMH would influence germ tube formation in Candida albicans, a fungal pathogen that synthesizes glucosylceramide and uses differentiation as a virulence factor. Addition of antiglucosylceramide antibodies to cultures of C. albicans clearly inhibited the generation of germ tubes. These results indicated that fungal CMHs might be involved in the differentiation and, consequently, play a role on the infectivity of fungal cells.

  Pseudallescheria boydii, ceramide monohexosides, fungal differentiation

  NCBI PubMed ID: 12042248
  Publication DOI: 10.1093/glycob/12.4.251
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Correspondence: eliana.bergter@micro.ufrj.br
  Institutions: Instituto de Microbiologia Professor Paulo de Goes, Federal University of Rio de Janeiro, Rio de Janeiro, Brazil, Universidade Federal Fluminense Niterói, Rio de Janeiro, Brazil, Fundação Oswaldo Cruz Rio de Janeiro, Brazil, Disciplina de Biologia Cellular, Universidade Federal de São Paulo, São Paulo, Sao Paulo, Brazil, University of Oxford, Oxford, United Kingdom
  Methods: 13C NMR, 1H NMR, NMR-2D, FAB-MS, GC-MS, sugar analysis, Western blotting, NMR-1D, methanolysis, extraction, acetylation, HPTLC, CC, HPTLC immunostaining
  
   
  
  Pseudallescheria boydii
  CSDB ID 43417 (all data & tools)

Show legend Show as text

Structure type: monomer
Compound class: glycosphingolipid, cerebroside
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_5

• Article ID: 7236
  Duarte RS, Polycarpo CR, Wait R, Hartmann R, Bergter EB "Structural characterization of neutral glycosphingolipids from Fusarium species" - Biochemical and Biophysical Research Communications 1390(2) (1998) 186-196
  

  Glycosphingolipids were extracted from hyphae of Fusarium solani and from an unnamed Fusarium species, and were purified by silica and Iatrobead column chromatography. Their structures were determined by compositional analysis, nuclear magnetic resonance spectroscopy, gas chromatography/mass spectrometry and by fast atom bombardment mass spectrometry of the native and peracetylated materials, which defined their sugar, long-chain base and fatty acid compositions. The locations of the double bonds in the bases were established by 2D NMR spectroscopy and by novel mass spectrometric approaches, including collisional activation of the protonated and lithium-cationized glycosphingolipids, and of the sphingadienene-derived fragment ion at m/z 276. From these results we propose that the structures of the glycosphingolipids from F. solani and Fusarium sp. are N-2'-hydroxyoctadecanoyl-1-O-β-D-glucopyranosyl-9-methyl-4, 8-sphingadienine and N-2'-hydroxyoctadecenoyl-1-O-β-D-glucopyranosyl-9-methyl-4, 8-sphingadienine, respectively.

  NMR spectroscopy, mass spectrometry, glycosphingolipid, Fast Atom Bombardment, Fusarium

  NCBI PubMed ID: 9507119
  Publication DOI: 10.1016/S0005-2760(97)00179-3
  Journal NLM ID: 0372516
  Publisher: Academic Press
  Correspondence: immgbel@microbio.ufrj.br
  Institutions: Institut für Physiologische Chemie, Universität Bonn, Bonn, Germany, Instituto de Microbiologia, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil, Centre for Applied Microbiology and Research, Salisbury, UK
  Methods: 1H NMR, NMR-2D, FAB-MS, GC-MS, sugar analysis, paper chromatography, methanolysis, extraction, HPTLC, CC, acetylation analysis
  
   
  
  Fusarium sp
  CSDB ID 42273 (all data & tools)