Show legend Show as text

Structure type: oligomer
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_130701,IEDB_144983,IEDB_152206,IEDB_164174,IEDB_983930,SB_197,SB_44,SB_67,SB_72

• Article ID: 7027
  Bennion B, Park C, Fuller M, Lindsey R, Momany M, Jennemann R, Levery SB "Glycosphingolipids of the model fungus Aspergillus nidulans: characterization of GIPCs with oligo-alpha-mannose-type glycans" - Journal of Lipid Research 44(11) (2003) 2073-2088
  

  Aspergillus nidulans is a well-established nonpathogenic laboratory model for the opportunistic mycopathogen, A. fumigatus. Some recent studies have focused on possible functional roles of glycosphingolipids (GSLs) in these fungi. It has been demonstrated that biosynthesis of glycosylinositol phosphorylceramides (GIPCs) is required for normal cell cycle progression and polarized growth in A. nidulans (Cheng, J., T.-S. Park, A. S. Fischl, and X. S. Ye. 2001. Mol. Cell Biol. 21: 6198-6209); however, the structures of A. nidulans GIPCs were not addressed in that study, nor were the functional significance of individual structural variants and the downstream steps in their biosynthesis. To initiate such studies, acidic GSL components (designated An-2, -3, and -5) were isolated from A. nidulans and subjected to structural characterization by a combination of one-dimensional (1-D) and 2-D NMR spectroscopy, electrospray ionization-mass spectrometry (ESI-MS), ESI-MS/collision-induced decomposition-MS (MS/CID-MS), ESI-pseudo-[CID-MS](2), and gas chromatography-MS methods.jlr All three were determined to be GIPCs, with mannose as the only monosaccharide present in the headgroup glycans; An-2 and An-3 were identified as di- and trimannosyl inositol phosphorylceramides (IPCs) with the structures Manα1→3Manα1→2Ins1-P-1Cer and Manα1→3(Manα1→6)Manα1→2Ins1-P-1Cer, respectively (where Ins = myo-inositol, P = phosphodiester, and Cer = ceramide). An-5 was partially characterized, and is proposed to be a pentamannosyl IPC, based on the trimannosyl core structure of An-3.-Bennion, B., C. Park, M. Fuller, R. Lindsey, M. Momany, R. Jennemann, and S. B. Levery. Glycosphingolipids of the model fungus Aspergillus nidulans: characterization of GIPCs with oligo-α-mannose-type glycans.

  NMR spectroscopy, mass spectrometry, glycolipid, tandem mass spectrometry, Electrospray Ionization, collision-induced dissociation, Aspergillus fumigatus

  Publication DOI: 10.1194/jlr.M300184-JLR200
  Journal NLM ID: 0376606
  Publisher: ASBMB
  Correspondence: slevery@cisunix.unh.edu
  Institutions: Department of Chemistry, University of New Hampshire, Durham, NH 03824-3598, The Complex Carbohydrate Research Center and Department of Biochemistry and Molecular Biology, and Department of Plant Biology, University of Georgia, Athens, GA 30602-7229, Abteilung für Zelluläre und Molekuläre Pathologie, Deutsches Krebsforschungszentrum-Heidelberg, Heidelberg, Germany
  Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, sugar analysis, ESI-MS, HPLC, extraction, HPTLC, ESI-CID-MS, ESI-QTOF-MS
  
   
  
  Aspergillus nidulans FGSC A28
  CSDB ID 41386 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_130701,IEDB_141793,IEDB_144983,IEDB_152206,IEDB_153220,IEDB_164174,IEDB_983930,SB_197,SB_198,SB_44,SB_67,SB_72,SB_73

• Article ID: 7027
  Bennion B, Park C, Fuller M, Lindsey R, Momany M, Jennemann R, Levery SB "Glycosphingolipids of the model fungus Aspergillus nidulans: characterization of GIPCs with oligo-alpha-mannose-type glycans" - Journal of Lipid Research 44(11) (2003) 2073-2088
  

  Aspergillus nidulans is a well-established nonpathogenic laboratory model for the opportunistic mycopathogen, A. fumigatus. Some recent studies have focused on possible functional roles of glycosphingolipids (GSLs) in these fungi. It has been demonstrated that biosynthesis of glycosylinositol phosphorylceramides (GIPCs) is required for normal cell cycle progression and polarized growth in A. nidulans (Cheng, J., T.-S. Park, A. S. Fischl, and X. S. Ye. 2001. Mol. Cell Biol. 21: 6198-6209); however, the structures of A. nidulans GIPCs were not addressed in that study, nor were the functional significance of individual structural variants and the downstream steps in their biosynthesis. To initiate such studies, acidic GSL components (designated An-2, -3, and -5) were isolated from A. nidulans and subjected to structural characterization by a combination of one-dimensional (1-D) and 2-D NMR spectroscopy, electrospray ionization-mass spectrometry (ESI-MS), ESI-MS/collision-induced decomposition-MS (MS/CID-MS), ESI-pseudo-[CID-MS](2), and gas chromatography-MS methods.jlr All three were determined to be GIPCs, with mannose as the only monosaccharide present in the headgroup glycans; An-2 and An-3 were identified as di- and trimannosyl inositol phosphorylceramides (IPCs) with the structures Manα1→3Manα1→2Ins1-P-1Cer and Manα1→3(Manα1→6)Manα1→2Ins1-P-1Cer, respectively (where Ins = myo-inositol, P = phosphodiester, and Cer = ceramide). An-5 was partially characterized, and is proposed to be a pentamannosyl IPC, based on the trimannosyl core structure of An-3.-Bennion, B., C. Park, M. Fuller, R. Lindsey, M. Momany, R. Jennemann, and S. B. Levery. Glycosphingolipids of the model fungus Aspergillus nidulans: characterization of GIPCs with oligo-α-mannose-type glycans.

  NMR spectroscopy, mass spectrometry, glycolipid, tandem mass spectrometry, Electrospray Ionization, collision-induced dissociation, Aspergillus fumigatus

  Publication DOI: 10.1194/jlr.M300184-JLR200
  Journal NLM ID: 0376606
  Publisher: ASBMB
  Correspondence: slevery@cisunix.unh.edu
  Institutions: Department of Chemistry, University of New Hampshire, Durham, NH 03824-3598, The Complex Carbohydrate Research Center and Department of Biochemistry and Molecular Biology, and Department of Plant Biology, University of Georgia, Athens, GA 30602-7229, Abteilung für Zelluläre und Molekuläre Pathologie, Deutsches Krebsforschungszentrum-Heidelberg, Heidelberg, Germany
  Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, sugar analysis, ESI-MS, HPLC, extraction, HPTLC, ESI-CID-MS, ESI-QTOF-MS
  
   
  
  Aspergillus nidulans FGSC A28
  CSDB ID 41387 (all data & tools)

Show legend Show as text

Structure type: structural motif or average structure
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_140116,IEDB_141793,IEDB_141828,IEDB_141829,IEDB_141831,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_153220,IEDB_164174,IEDB_76933,IEDB_983930,SB_136,SB_191,SB_196,SB_197,SB_198,SB_44,SB_67,SB_72,SB_73

• Article ID: 7027
  Bennion B, Park C, Fuller M, Lindsey R, Momany M, Jennemann R, Levery SB "Glycosphingolipids of the model fungus Aspergillus nidulans: characterization of GIPCs with oligo-alpha-mannose-type glycans" - Journal of Lipid Research 44(11) (2003) 2073-2088
  

  Aspergillus nidulans is a well-established nonpathogenic laboratory model for the opportunistic mycopathogen, A. fumigatus. Some recent studies have focused on possible functional roles of glycosphingolipids (GSLs) in these fungi. It has been demonstrated that biosynthesis of glycosylinositol phosphorylceramides (GIPCs) is required for normal cell cycle progression and polarized growth in A. nidulans (Cheng, J., T.-S. Park, A. S. Fischl, and X. S. Ye. 2001. Mol. Cell Biol. 21: 6198-6209); however, the structures of A. nidulans GIPCs were not addressed in that study, nor were the functional significance of individual structural variants and the downstream steps in their biosynthesis. To initiate such studies, acidic GSL components (designated An-2, -3, and -5) were isolated from A. nidulans and subjected to structural characterization by a combination of one-dimensional (1-D) and 2-D NMR spectroscopy, electrospray ionization-mass spectrometry (ESI-MS), ESI-MS/collision-induced decomposition-MS (MS/CID-MS), ESI-pseudo-[CID-MS](2), and gas chromatography-MS methods.jlr All three were determined to be GIPCs, with mannose as the only monosaccharide present in the headgroup glycans; An-2 and An-3 were identified as di- and trimannosyl inositol phosphorylceramides (IPCs) with the structures Manα1→3Manα1→2Ins1-P-1Cer and Manα1→3(Manα1→6)Manα1→2Ins1-P-1Cer, respectively (where Ins = myo-inositol, P = phosphodiester, and Cer = ceramide). An-5 was partially characterized, and is proposed to be a pentamannosyl IPC, based on the trimannosyl core structure of An-3.-Bennion, B., C. Park, M. Fuller, R. Lindsey, M. Momany, R. Jennemann, and S. B. Levery. Glycosphingolipids of the model fungus Aspergillus nidulans: characterization of GIPCs with oligo-α-mannose-type glycans.

  NMR spectroscopy, mass spectrometry, glycolipid, tandem mass spectrometry, Electrospray Ionization, collision-induced dissociation, Aspergillus fumigatus

  Publication DOI: 10.1194/jlr.M300184-JLR200
  Journal NLM ID: 0376606
  Publisher: ASBMB
  Correspondence: slevery@cisunix.unh.edu
  Institutions: Department of Chemistry, University of New Hampshire, Durham, NH 03824-3598, The Complex Carbohydrate Research Center and Department of Biochemistry and Molecular Biology, and Department of Plant Biology, University of Georgia, Athens, GA 30602-7229, Abteilung für Zelluläre und Molekuläre Pathologie, Deutsches Krebsforschungszentrum-Heidelberg, Heidelberg, Germany
  Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, sugar analysis, ESI-MS, HPLC, extraction, HPTLC, ESI-CID-MS, ESI-QTOF-MS
  
   
  
  Aspergillus nidulans FGSC A28
  CSDB ID 41388 (all data & tools)

Show legend Show as text

Structure type: monomer ; 1072 [M+Li]+; 1100 [M+Li]+; 1128 [M+Li]+
Compound class: ceramide
Contained glycoepitopes: IEDB_130701,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_67,SB_72

• Article ID: 7561
  Levery SB, Toledo MS, Straus AH, Takahashi HK "Comparative analysis of glycosylinositol phosphorylceramides from fungi by electrospray tandem mass spectrometry with low-energy collision-induced dissociation of Li+ adduct ions" - Rapid Communications in Mass Spectrometry 15(23) (2001) 2240-2258
  

  Glycosylinositol phosphorylceramides (GIPCs) are a class of acidic glycosphingolipids (GSLs) expressed by fungi, plants, and certain parasitic organisms, but not found in cells or tissues of mammals or other higher animals. Recent characterizations of fungal GIPCs point to an emerging diversity which could rival that already known for mammalian GSLs, and which can be expected to present a multitude of challenges for the analytical chemist. Previously, the use of Li+ cationization, in conjunction with electrospray ionization mass spectrometry (ESI-MS) and low-energy collision-induced dissociation tandem mass spectrometry (ESI-MS/CID-MS), was found to be particularly effective for detailed structural analysis of monohexosylceramides (cerebrosides) from a variety of sources, including fungi, especially minor components present in mixtures at extremely low abundance. In applying Li+ cationization to characterization of GIPCs, a substantial increase in both sensitivity and fragmentation was observed on collision-induced dissociation of [M + Li]+ versus [M + Na]+ for the same components analyzed under similar conditions, similar to results obtained previously with cerebrosides. Molecular adduct fragmentation patterns were found to be systematic and characteristic for both the glycosylinositol and ceramide moieties with or without phosphate. Interestingly, significant differences were observed in fragmentation patterns when comparing GIPCs having Manα1→2 versus Manα1→6Ins core linkages. In addition, it was useful to perform tandem product ion scans on primary fragments generated in the orifice region, equivalent to ESI-(CID-MS)2 mode. Finally, precursor ion scanning from appropriate glycosylinositol phosphate product ions yielded clean molecular ion profiles in the presence of obscuring impurity peaks. The methods were applied to detailed characterization of GIPC fractions of increasing structural complexity from a variety of fungi, including a non-pathogenic Basidiomycete (mushroom), Agaricus blazei, and pathogenic Euascomycete species such as Aspergillus fumigatus, Histoplasma capsulatum, and Sporothrix schenckii. The analysis confirmed a remarkable diversity of GIPC structures synthesized by the dimorphic S. schenckii, as well as differential expression of both glycosylinositol and ceramide structures in the mycelium and yeast forms of this mycopathogen. Mass spectrometry also established that the ceramides of some A. fumigatus GIPC fractions contain very little 2-hydroxylation of the long-chain fatty-N-acyl moiety, a feature that is not generally observed with fungal GIPCs.

  mass spectrometry, glycosphingolipids, Aspergillus fumigatus, Agaricus blazei, glucosylceramides, Histoplasma capsulatum

  NCBI PubMed ID: 11746891
  Publication DOI: 10.1002/rcm.505
  Journal NLM ID: 8802365
  Publisher: John Wiley And Sons Ltd
  Correspondence: leverysb@ccrc.uga.edu
  Institutions: Complex Carbohydrate Research Center, Department of Biochemistry and Molecular Biology, University of Georgia, Athens, USA, Department of Biochemistry, Universidade Federal de São Paulo, Escola Paulista de Medicina, São Paulo, Brazil
  Methods: 13C NMR, 1H NMR, GC-MS, ESI-MS, extraction, ESI-CID-MS, cell growth
  
   
  
  Agaricus blazei
  CSDB ID 44309 (all data & tools)

Show legend Show as text

Structure type: monomer ; 1100 [M+Li]+
Compound class: ceramide
Contained glycoepitopes: IEDB_130701,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_67,SB_72

• Article ID: 7561
  Levery SB, Toledo MS, Straus AH, Takahashi HK "Comparative analysis of glycosylinositol phosphorylceramides from fungi by electrospray tandem mass spectrometry with low-energy collision-induced dissociation of Li+ adduct ions" - Rapid Communications in Mass Spectrometry 15(23) (2001) 2240-2258
  

  Glycosylinositol phosphorylceramides (GIPCs) are a class of acidic glycosphingolipids (GSLs) expressed by fungi, plants, and certain parasitic organisms, but not found in cells or tissues of mammals or other higher animals. Recent characterizations of fungal GIPCs point to an emerging diversity which could rival that already known for mammalian GSLs, and which can be expected to present a multitude of challenges for the analytical chemist. Previously, the use of Li+ cationization, in conjunction with electrospray ionization mass spectrometry (ESI-MS) and low-energy collision-induced dissociation tandem mass spectrometry (ESI-MS/CID-MS), was found to be particularly effective for detailed structural analysis of monohexosylceramides (cerebrosides) from a variety of sources, including fungi, especially minor components present in mixtures at extremely low abundance. In applying Li+ cationization to characterization of GIPCs, a substantial increase in both sensitivity and fragmentation was observed on collision-induced dissociation of [M + Li]+ versus [M + Na]+ for the same components analyzed under similar conditions, similar to results obtained previously with cerebrosides. Molecular adduct fragmentation patterns were found to be systematic and characteristic for both the glycosylinositol and ceramide moieties with or without phosphate. Interestingly, significant differences were observed in fragmentation patterns when comparing GIPCs having Manα1→2 versus Manα1→6Ins core linkages. In addition, it was useful to perform tandem product ion scans on primary fragments generated in the orifice region, equivalent to ESI-(CID-MS)2 mode. Finally, precursor ion scanning from appropriate glycosylinositol phosphate product ions yielded clean molecular ion profiles in the presence of obscuring impurity peaks. The methods were applied to detailed characterization of GIPC fractions of increasing structural complexity from a variety of fungi, including a non-pathogenic Basidiomycete (mushroom), Agaricus blazei, and pathogenic Euascomycete species such as Aspergillus fumigatus, Histoplasma capsulatum, and Sporothrix schenckii. The analysis confirmed a remarkable diversity of GIPC structures synthesized by the dimorphic S. schenckii, as well as differential expression of both glycosylinositol and ceramide structures in the mycelium and yeast forms of this mycopathogen. Mass spectrometry also established that the ceramides of some A. fumigatus GIPC fractions contain very little 2-hydroxylation of the long-chain fatty-N-acyl moiety, a feature that is not generally observed with fungal GIPCs.

  mass spectrometry, glycosphingolipids, Aspergillus fumigatus, Agaricus blazei, glucosylceramides, Histoplasma capsulatum

  NCBI PubMed ID: 11746891
  Publication DOI: 10.1002/rcm.505
  Journal NLM ID: 8802365
  Publisher: John Wiley And Sons Ltd
  Correspondence: leverysb@ccrc.uga.edu
  Institutions: Complex Carbohydrate Research Center, Department of Biochemistry and Molecular Biology, University of Georgia, Athens, USA, Department of Biochemistry, Universidade Federal de São Paulo, Escola Paulista de Medicina, São Paulo, Brazil
  Methods: 13C NMR, 1H NMR, GC-MS, ESI-MS, extraction, ESI-CID-MS, cell growth
  
   
  
  Sporothrix schenckii 65
  CSDB ID 44310 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1262 [M+Li]+
Compound class: ceramide
Contained glycoepitopes: IEDB_130701,IEDB_144983,IEDB_152206,IEDB_164174,IEDB_983930,SB_197,SB_44,SB_67,SB_72

• Article ID: 7561
  Levery SB, Toledo MS, Straus AH, Takahashi HK "Comparative analysis of glycosylinositol phosphorylceramides from fungi by electrospray tandem mass spectrometry with low-energy collision-induced dissociation of Li+ adduct ions" - Rapid Communications in Mass Spectrometry 15(23) (2001) 2240-2258
  

  Glycosylinositol phosphorylceramides (GIPCs) are a class of acidic glycosphingolipids (GSLs) expressed by fungi, plants, and certain parasitic organisms, but not found in cells or tissues of mammals or other higher animals. Recent characterizations of fungal GIPCs point to an emerging diversity which could rival that already known for mammalian GSLs, and which can be expected to present a multitude of challenges for the analytical chemist. Previously, the use of Li+ cationization, in conjunction with electrospray ionization mass spectrometry (ESI-MS) and low-energy collision-induced dissociation tandem mass spectrometry (ESI-MS/CID-MS), was found to be particularly effective for detailed structural analysis of monohexosylceramides (cerebrosides) from a variety of sources, including fungi, especially minor components present in mixtures at extremely low abundance. In applying Li+ cationization to characterization of GIPCs, a substantial increase in both sensitivity and fragmentation was observed on collision-induced dissociation of [M + Li]+ versus [M + Na]+ for the same components analyzed under similar conditions, similar to results obtained previously with cerebrosides. Molecular adduct fragmentation patterns were found to be systematic and characteristic for both the glycosylinositol and ceramide moieties with or without phosphate. Interestingly, significant differences were observed in fragmentation patterns when comparing GIPCs having Manα1→2 versus Manα1→6Ins core linkages. In addition, it was useful to perform tandem product ion scans on primary fragments generated in the orifice region, equivalent to ESI-(CID-MS)2 mode. Finally, precursor ion scanning from appropriate glycosylinositol phosphate product ions yielded clean molecular ion profiles in the presence of obscuring impurity peaks. The methods were applied to detailed characterization of GIPC fractions of increasing structural complexity from a variety of fungi, including a non-pathogenic Basidiomycete (mushroom), Agaricus blazei, and pathogenic Euascomycete species such as Aspergillus fumigatus, Histoplasma capsulatum, and Sporothrix schenckii. The analysis confirmed a remarkable diversity of GIPC structures synthesized by the dimorphic S. schenckii, as well as differential expression of both glycosylinositol and ceramide structures in the mycelium and yeast forms of this mycopathogen. Mass spectrometry also established that the ceramides of some A. fumigatus GIPC fractions contain very little 2-hydroxylation of the long-chain fatty-N-acyl moiety, a feature that is not generally observed with fungal GIPCs.

  mass spectrometry, glycosphingolipids, Aspergillus fumigatus, Agaricus blazei, glucosylceramides, Histoplasma capsulatum

  NCBI PubMed ID: 11746891
  Publication DOI: 10.1002/rcm.505
  Journal NLM ID: 8802365
  Publisher: John Wiley And Sons Ltd
  Correspondence: leverysb@ccrc.uga.edu
  Institutions: Complex Carbohydrate Research Center, Department of Biochemistry and Molecular Biology, University of Georgia, Athens, USA, Department of Biochemistry, Universidade Federal de São Paulo, Escola Paulista de Medicina, São Paulo, Brazil
  Methods: 13C NMR, 1H NMR, GC-MS, ESI-MS, extraction, ESI-CID-MS, cell growth
  
   
  
  Sporothrix schenckii 65
  CSDB ID 44311 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycosphingolipid, glycoinositolphosphoryl ceramide (GIPC)
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_140116,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_164174,IEDB_983930,SB_136,SB_196,SB_197,SB_44,SB_67,SB_72

• Article ID: 7669
  Fontaine T "Sphingolipids from the human fungal pathogen Aspergillus fumigatus" - Biochimie 141 (2017) 9-15
  

  Sphingolipids (SPLs) are key components of the plasma membrane in yeast and filamentous fungi. These molecules are involved in a number of cellular processes, and particularly, SGLs are essential components of the highly polarized fungal growth where they are required for the formation of the polarisome organization at the hyphal apex. Aspergillus fumigatus, a human fungal pathogen, produce SGLs that are discriminated into neutral cerebrosides, glycosylinositolphosphoceramides (GIPCs) and glycosylphosphatidylinositol (GPI) anchors. In addition to complex hydrophilic head groups of GIPCs, A. fumigatus is, to date, the sole fungus that produces a GPI-anchored polysaccharide. These SPLs follow three different biosynthetic pathways. Genetics blockage leading to the inhibition of any SPL biosynthesis or to the alteration of the structure of SPL induces growth and virulence defects. The complete lipid moiety of SPLs is essential for the lipid microdomain organization and their biosynthetic pathways are potential antifungal targets but remains understudied.

  Aspergillus fumigatus, GPI, glucosylceramide, GIPC

  NCBI PubMed ID: 28652019
  Publication DOI: 10.1016/j.biochi.2017.06.012
  Journal NLM ID: 1264604
  Publisher: Paris: Editions Scientifiques Elsevier
  Correspondence: thierry.fontaine@pasteur.fr
  Institutions: Unité des Aspergillus, Institut Pasteur, Paris, France
  
   
  
  Aspergillus fumigatus
  CSDB ID 43096 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycosphingolipid, glycoinositolphosphoryl ceramide (GIPC)
Contained glycoepitopes: IEDB_130701,IEDB_136095,IEDB_137472,IEDB_144983,IEDB_152206,IEDB_164174,IEDB_190606,IEDB_983930,SB_197,SB_44,SB_67,SB_72

• Article ID: 7669
  Fontaine T "Sphingolipids from the human fungal pathogen Aspergillus fumigatus" - Biochimie 141 (2017) 9-15
  

  Sphingolipids (SPLs) are key components of the plasma membrane in yeast and filamentous fungi. These molecules are involved in a number of cellular processes, and particularly, SGLs are essential components of the highly polarized fungal growth where they are required for the formation of the polarisome organization at the hyphal apex. Aspergillus fumigatus, a human fungal pathogen, produce SGLs that are discriminated into neutral cerebrosides, glycosylinositolphosphoceramides (GIPCs) and glycosylphosphatidylinositol (GPI) anchors. In addition to complex hydrophilic head groups of GIPCs, A. fumigatus is, to date, the sole fungus that produces a GPI-anchored polysaccharide. These SPLs follow three different biosynthetic pathways. Genetics blockage leading to the inhibition of any SPL biosynthesis or to the alteration of the structure of SPL induces growth and virulence defects. The complete lipid moiety of SPLs is essential for the lipid microdomain organization and their biosynthetic pathways are potential antifungal targets but remains understudied.

  Aspergillus fumigatus, GPI, glucosylceramide, GIPC

  NCBI PubMed ID: 28652019
  Publication DOI: 10.1016/j.biochi.2017.06.012
  Journal NLM ID: 1264604
  Publisher: Paris: Editions Scientifiques Elsevier
  Correspondence: thierry.fontaine@pasteur.fr
  Institutions: Unité des Aspergillus, Institut Pasteur, Paris, France
  
   
  
  Aspergillus fumigatus
  CSDB ID 43097 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycosphingolipid, glycoinositolphosphoryl ceramide (GIPC)
Contained glycoepitopes: IEDB_130701,IEDB_136095,IEDB_136104,IEDB_137472,IEDB_140116,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_164174,IEDB_190606,IEDB_983930,SB_136,SB_196,SB_197,SB_44,SB_67,SB_72

• Article ID: 7669
  Fontaine T "Sphingolipids from the human fungal pathogen Aspergillus fumigatus" - Biochimie 141 (2017) 9-15
  

  Sphingolipids (SPLs) are key components of the plasma membrane in yeast and filamentous fungi. These molecules are involved in a number of cellular processes, and particularly, SGLs are essential components of the highly polarized fungal growth where they are required for the formation of the polarisome organization at the hyphal apex. Aspergillus fumigatus, a human fungal pathogen, produce SGLs that are discriminated into neutral cerebrosides, glycosylinositolphosphoceramides (GIPCs) and glycosylphosphatidylinositol (GPI) anchors. In addition to complex hydrophilic head groups of GIPCs, A. fumigatus is, to date, the sole fungus that produces a GPI-anchored polysaccharide. These SPLs follow three different biosynthetic pathways. Genetics blockage leading to the inhibition of any SPL biosynthesis or to the alteration of the structure of SPL induces growth and virulence defects. The complete lipid moiety of SPLs is essential for the lipid microdomain organization and their biosynthetic pathways are potential antifungal targets but remains understudied.

  Aspergillus fumigatus, GPI, glucosylceramide, GIPC

  NCBI PubMed ID: 28652019
  Publication DOI: 10.1016/j.biochi.2017.06.012
  Journal NLM ID: 1264604
  Publisher: Paris: Editions Scientifiques Elsevier
  Correspondence: thierry.fontaine@pasteur.fr
  Institutions: Unité des Aspergillus, Institut Pasteur, Paris, France
  
   
  
  Aspergillus fumigatus
  CSDB ID 43098 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: sphingolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_137485,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_72

• Article ID: 8001
  Guan XL, Wenk MR "Mass spectrometry-based profiling of phospholipids and sphingolipids in extracts from Saccharomyces cerevisiae" - Yeast 23(6) (2006) 465-477
  

  Lipids are rapidly moving to centre stage in many fields of biological sciences. Lipidomics, the systems-level scale analysis of lipids and their interacting factors, is thus an emerging field which holds great promise for drug and biomarker discovery. Here we present a mass spectrometry-based approach for profiling of polar lipids, in particular phospholipids and sphingolipids, in Saccharomyces cerevisiae. The first step includes semi-quantitative surveys of lipids in an untargeted fashion, which is particularly powerful for detection of changes that cannot easily be anticipated. This leads to the identification of ions with increased or decreased signal intensities. Comprehensive theoretical calculation of the masses of yeast phospholipid and sphingolipid molecular species, based on fatty acyl and headgroup heterogeneity, is next used to tentatively assign ions of interest. Subsequent targeted analysis using tandem mass spectrometry allows for characterization and quantification of phospholipids and sphingolipids. Given the high degree of conservation in pathways of lipid metabolism between different organisms, it can be expected that this method will lead to the discovery of novel enzymatic activities and modulators of known ones, particularly when used in combination with genetic and chemogenetic libraries and screens. We validated the method using the EUROSCARF library of non-essential deletion mutants. Mutants of SCS7, a lipid hydroxylase, and SLC1, a putative acyl transferase with unknown substrate specificity, were profiled for their phospholipid and sphingolipid content. The observed changes in lipid profiles are consistent with previous observations and extend our knowledge on in vivo substrate use under permissive growth conditions.

  mass spectrometry, phospholipid, lipidomics, sphingolipid, S. cerevisiae

  NCBI PubMed ID: 16652392
  Publication DOI: 10.1002/yea.1362
  Journal NLM ID: 8607637
  Publisher: Chichester, Wiley
  Correspondence: Wenk MR
  Institutions: Department of Biochemistry and Department of Biological Sciences, National University of Singapore, Singapore
  Methods: extraction, ESI-QTOF-MS/MS, cell growth
  
   
  
  Saccharomyces cerevisiae BY4741, Saccharomyces cerevisiae (Δslc1 mutant), Saccharomyces cerevisiae (Δscs7 mutant)
  CSDB ID 45513 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: sphingolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_137485,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_72

• Article ID: 8001
  Guan XL, Wenk MR "Mass spectrometry-based profiling of phospholipids and sphingolipids in extracts from Saccharomyces cerevisiae" - Yeast 23(6) (2006) 465-477
  

  Lipids are rapidly moving to centre stage in many fields of biological sciences. Lipidomics, the systems-level scale analysis of lipids and their interacting factors, is thus an emerging field which holds great promise for drug and biomarker discovery. Here we present a mass spectrometry-based approach for profiling of polar lipids, in particular phospholipids and sphingolipids, in Saccharomyces cerevisiae. The first step includes semi-quantitative surveys of lipids in an untargeted fashion, which is particularly powerful for detection of changes that cannot easily be anticipated. This leads to the identification of ions with increased or decreased signal intensities. Comprehensive theoretical calculation of the masses of yeast phospholipid and sphingolipid molecular species, based on fatty acyl and headgroup heterogeneity, is next used to tentatively assign ions of interest. Subsequent targeted analysis using tandem mass spectrometry allows for characterization and quantification of phospholipids and sphingolipids. Given the high degree of conservation in pathways of lipid metabolism between different organisms, it can be expected that this method will lead to the discovery of novel enzymatic activities and modulators of known ones, particularly when used in combination with genetic and chemogenetic libraries and screens. We validated the method using the EUROSCARF library of non-essential deletion mutants. Mutants of SCS7, a lipid hydroxylase, and SLC1, a putative acyl transferase with unknown substrate specificity, were profiled for their phospholipid and sphingolipid content. The observed changes in lipid profiles are consistent with previous observations and extend our knowledge on in vivo substrate use under permissive growth conditions.

  mass spectrometry, phospholipid, lipidomics, sphingolipid, S. cerevisiae

  NCBI PubMed ID: 16652392
  Publication DOI: 10.1002/yea.1362
  Journal NLM ID: 8607637
  Publisher: Chichester, Wiley
  Correspondence: Wenk MR
  Institutions: Department of Biochemistry and Department of Biological Sciences, National University of Singapore, Singapore
  Methods: extraction, ESI-QTOF-MS/MS, cell growth
  
   
  
  Saccharomyces cerevisiae BY4741, Saccharomyces cerevisiae (Δslc1 mutant), Saccharomyces cerevisiae (Δscs7 mutant)
  CSDB ID 45514 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: sphingolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_137485,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_72

• Article ID: 8001
  Guan XL, Wenk MR "Mass spectrometry-based profiling of phospholipids and sphingolipids in extracts from Saccharomyces cerevisiae" - Yeast 23(6) (2006) 465-477
  

  Lipids are rapidly moving to centre stage in many fields of biological sciences. Lipidomics, the systems-level scale analysis of lipids and their interacting factors, is thus an emerging field which holds great promise for drug and biomarker discovery. Here we present a mass spectrometry-based approach for profiling of polar lipids, in particular phospholipids and sphingolipids, in Saccharomyces cerevisiae. The first step includes semi-quantitative surveys of lipids in an untargeted fashion, which is particularly powerful for detection of changes that cannot easily be anticipated. This leads to the identification of ions with increased or decreased signal intensities. Comprehensive theoretical calculation of the masses of yeast phospholipid and sphingolipid molecular species, based on fatty acyl and headgroup heterogeneity, is next used to tentatively assign ions of interest. Subsequent targeted analysis using tandem mass spectrometry allows for characterization and quantification of phospholipids and sphingolipids. Given the high degree of conservation in pathways of lipid metabolism between different organisms, it can be expected that this method will lead to the discovery of novel enzymatic activities and modulators of known ones, particularly when used in combination with genetic and chemogenetic libraries and screens. We validated the method using the EUROSCARF library of non-essential deletion mutants. Mutants of SCS7, a lipid hydroxylase, and SLC1, a putative acyl transferase with unknown substrate specificity, were profiled for their phospholipid and sphingolipid content. The observed changes in lipid profiles are consistent with previous observations and extend our knowledge on in vivo substrate use under permissive growth conditions.

  mass spectrometry, phospholipid, lipidomics, sphingolipid, S. cerevisiae

  NCBI PubMed ID: 16652392
  Publication DOI: 10.1002/yea.1362
  Journal NLM ID: 8607637
  Publisher: Chichester, Wiley
  Correspondence: Wenk MR
  Institutions: Department of Biochemistry and Department of Biological Sciences, National University of Singapore, Singapore
  Methods: extraction, ESI-QTOF-MS/MS, cell growth
  
   
  
  Saccharomyces cerevisiae
  CSDB ID 45515 (all data & tools)

Show legend Show as text

Structure type: monomer
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_130701,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_67,SB_72

• Article ID: 8032
  Buré C, Cacas JL, Mongrand S, Schmitter JM "Characterization of glycosyl inositol phosphoryl ceramides from plants and fungi by mass spectrometry" - Analytical and Bioanalytical Chemistry 406(4) (2014) 995-1010
  

  Although glycosyl inositol phosphoryl ceramides (GIPCs) represent the most abundant class of sphingolipids in plants, they still remain poorly characterized in terms of structure and biodiversity. More than 50 years after their discovery, little is known about their subcellular distribution and their exact roles in membrane structure and biological functions. This review is focused on extraction and characterization methods of GIPCs occurring in plants and fungi. Global methods for characterizing ceramide moieties of GIPCs revealed the structures of long-chain bases (LCBs) and fatty acids (FAs): LCBs are dominated by tri-hydroxylated molecules such as monounsaturated and saturated phytosphingosine (t18:1 and t18:0, respectively) in plants and mainly phytosphingosine (t18:0 and t20:0) in fungi; FA are generally 14-26 carbon atoms long in plants and 16-26 carbon atoms long in fungi, these chains being often hydroxylated in position 2. Mass spectrometry plays a pivotal role in the assessment of GIPC diversity and the characterization of their structures. Indeed, it allowed to determine that the core structure of GIPC polar heads in plants is Hex(R1)-HexA-IPC, with R1 being a hydroxyl, an amine, or a N-acetylamine group, whereas the core structure in fungi is Man-IPC. Notably, information gained from tandem mass spectrometry spectra was most useful to describe the huge variety of structures encountered in plants and fungi and reveal GIPCs with yet uncharacterized polar head structures, such as hexose-inositol phosphoceramide in Chondracanthus acicularis and (hexuronic acid)4-inositol phosphoceramide and hexose-(hexuronic acid)3-inositol phosphoceramide in Ulva lactuca.

  mass spectrometry, Plants, sphingolipids, fungi, glycosyl inositol phosphoryl ceramide

  NCBI PubMed ID: 23887274
  Publication DOI: 10.1007/s00216-013-7130-8
  Journal NLM ID: 101134327
  Publisher: Heidelberg: Springer-Verlag
  Correspondence: Buré C
  Institutions: Université de Bordeaux, Chimie Biologie des Membranes et Nanoobjets CBMN-UMR 5248 Centre de Génomique Fonctionnelle, Université Bordeaux Segalen, Bordeaux, France, Université de Bordeaux, Laboratoire de Biogenèse Membranaire, UMR 5200 CNRS-Université Bordeaux Segalen, Villenave-d’Ornon, France, UMR1347 Agroécologie, INRA/Université de Bourgogne/AgrosupPôle Interactions Plante-Microorganisme, Dijon, France
  Methods: GC-MS, NMR, TLC, MALDI-MS
  
   
  
  Agaricus blazei, Calvatia exipuliformis, Lentinula edodes
  CSDB ID 46256 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_115009,IEDB_116046,IEDB_130701,IEDB_136095,IEDB_137472,IEDB_140624,IEDB_144983,IEDB_152206,IEDB_164174,IEDB_190606,IEDB_983930,SB_197,SB_44,SB_67,SB_72

• Article ID: 8032
  Buré C, Cacas JL, Mongrand S, Schmitter JM "Characterization of glycosyl inositol phosphoryl ceramides from plants and fungi by mass spectrometry" - Analytical and Bioanalytical Chemistry 406(4) (2014) 995-1010
  

  Although glycosyl inositol phosphoryl ceramides (GIPCs) represent the most abundant class of sphingolipids in plants, they still remain poorly characterized in terms of structure and biodiversity. More than 50 years after their discovery, little is known about their subcellular distribution and their exact roles in membrane structure and biological functions. This review is focused on extraction and characterization methods of GIPCs occurring in plants and fungi. Global methods for characterizing ceramide moieties of GIPCs revealed the structures of long-chain bases (LCBs) and fatty acids (FAs): LCBs are dominated by tri-hydroxylated molecules such as monounsaturated and saturated phytosphingosine (t18:1 and t18:0, respectively) in plants and mainly phytosphingosine (t18:0 and t20:0) in fungi; FA are generally 14-26 carbon atoms long in plants and 16-26 carbon atoms long in fungi, these chains being often hydroxylated in position 2. Mass spectrometry plays a pivotal role in the assessment of GIPC diversity and the characterization of their structures. Indeed, it allowed to determine that the core structure of GIPC polar heads in plants is Hex(R1)-HexA-IPC, with R1 being a hydroxyl, an amine, or a N-acetylamine group, whereas the core structure in fungi is Man-IPC. Notably, information gained from tandem mass spectrometry spectra was most useful to describe the huge variety of structures encountered in plants and fungi and reveal GIPCs with yet uncharacterized polar head structures, such as hexose-inositol phosphoceramide in Chondracanthus acicularis and (hexuronic acid)4-inositol phosphoceramide and hexose-(hexuronic acid)3-inositol phosphoceramide in Ulva lactuca.

  mass spectrometry, Plants, sphingolipids, fungi, glycosyl inositol phosphoryl ceramide

  NCBI PubMed ID: 23887274
  Publication DOI: 10.1007/s00216-013-7130-8
  Journal NLM ID: 101134327
  Publisher: Heidelberg: Springer-Verlag
  Correspondence: Buré C
  Institutions: Université de Bordeaux, Chimie Biologie des Membranes et Nanoobjets CBMN-UMR 5248 Centre de Génomique Fonctionnelle, Université Bordeaux Segalen, Bordeaux, France, Université de Bordeaux, Laboratoire de Biogenèse Membranaire, UMR 5200 CNRS-Université Bordeaux Segalen, Villenave-d’Ornon, France, UMR1347 Agroécologie, INRA/Université de Bourgogne/AgrosupPôle Interactions Plante-Microorganisme, Dijon, France
  Methods: GC-MS, NMR, TLC, MALDI-MS
  
   
  
  Aspergillus fumigatus
  CSDB ID 46262 (all data & tools)