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: oligomer
Compound class: glycosphingolipid, glycosylinositolphosphoceramide (GIPC)
Contained glycoepitopes: IEDB_130701,IEDB_1394182,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_67,SB_72

• Article ID: 7128
  Arigi E, Singh S, Kahlili AH, Winter HC, Goldstein IJ, Levery SB "Characterization of neutral and acidic glycosphingolipids from the lectin-producing mushroom, Polyporus squamosus" - Glycobiology 17(7) (2007) 754-766
  

  The polypore mushroom Polyporus squamosus is the source of a lectin that exhibits a general affinity for terminal β-galactosides, but appears to have an extended carbohydrate-binding site with high affinity and strict specificity for the nonreducing terminal trisaccharide sequence NeuAcα2→6Galβ1→4Glc/GlcNAc. In considering the possibility that the lectin's in vivo function could involve interaction with an endogenous glycoconjugate, it would clearly be helpful to identify candidate ligands among various classes of carbohydrate-containing materials expressed by P. squamosus. Since evidence has been accumulating that glycosphingolipids (GSLs) may serve as key ligands for some endogenous lectins in animal species, possible similar roles for fungal GSLs could be considered. For this study, total lipids were extracted from mature fruiting body of P. squamosus. Multistep fractionation yielded a major monohexosylceramide (CMH) component and three major glycosylinositol phosphorylceramides (GIPCs) from the neutral and acidic lipids, respectively. These were characterized by a variety of techniques as required, including one- and two-dimensional (1)H- and (13)C-nuclear magnetic resonance (NMR) spectroscopy; electrospray ionization-mass spectrometry (ESI-MS, tandem-MS/collision-induced decay-MS, and ion trap-MS(n)); and component and methylation linkage analysis by gas chromatography-mass spectrometry. The CMH was determined to be glucosylceramide having a typical ceramide consisting of 2-hydroxy fatty-N-acylated (4E,8E)-9-methyl-sphinga-4,8-dienine. The GIPCs were identified as Manα1→2Ins1-P-1Cer (Ps-1), Galβ1→6Manα1→2Ins1-P-1Cer (Ps-2), and Manα1→3Fucα1→2Galα1→6Galβ1→6Manα1→2Ins1-P-1Cer (Ps-5), respectively (where Ins = myo-inositol, P = phosphodiester, and Cer = ceramide consisting mainly of long-chain 2-hydroxy and 2,3-dihydroxy fatty-N-acylated 4-hydroxy-sphinganines). Of these GSLs, Ps-2 could potentially interact with P. squamosus lectin, and further investigations will focus on determining the binding affinity, if any, of the lectin for the GIPCs isolated from this fungus.

  NMR spectroscopy, mass spectrometry, glycolipid, Electrospray Ionization, Basidiomycete

  NCBI PubMed ID: 17395693
  Publication DOI: 10.1093/glycob/cwm035
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Correspondence: slevery@cisunix.unh.edu (Steven B Levery)
  Institutions: Department of Chemistry, University of New Hampshire, Durham, North Carolina, USA, Department of Biochemistry and Molecular Biology, The Complex Carbohydrate Research Center, University of Georgia, Athens, Georgia, USA, Department of Biological Chemistry, School of Medicine, University of Michigan, Ann Arbor, Michigan, USA
  Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, composition analysis, CID-MS/MS, HPLC, extraction, HPTLC, ESI-QTOF-MS, MALDI-QIT-TOF-MS
  
   
  
  Polyporus squamosus
  CSDB ID 41800 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycosphingolipid, glycosylinositolphosphoceramide (GIPC)
Contained glycoepitopes: IEDB_130701,IEDB_136044,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: 7128
  Arigi E, Singh S, Kahlili AH, Winter HC, Goldstein IJ, Levery SB "Characterization of neutral and acidic glycosphingolipids from the lectin-producing mushroom, Polyporus squamosus" - Glycobiology 17(7) (2007) 754-766
  

  The polypore mushroom Polyporus squamosus is the source of a lectin that exhibits a general affinity for terminal β-galactosides, but appears to have an extended carbohydrate-binding site with high affinity and strict specificity for the nonreducing terminal trisaccharide sequence NeuAcα2→6Galβ1→4Glc/GlcNAc. In considering the possibility that the lectin's in vivo function could involve interaction with an endogenous glycoconjugate, it would clearly be helpful to identify candidate ligands among various classes of carbohydrate-containing materials expressed by P. squamosus. Since evidence has been accumulating that glycosphingolipids (GSLs) may serve as key ligands for some endogenous lectins in animal species, possible similar roles for fungal GSLs could be considered. For this study, total lipids were extracted from mature fruiting body of P. squamosus. Multistep fractionation yielded a major monohexosylceramide (CMH) component and three major glycosylinositol phosphorylceramides (GIPCs) from the neutral and acidic lipids, respectively. These were characterized by a variety of techniques as required, including one- and two-dimensional (1)H- and (13)C-nuclear magnetic resonance (NMR) spectroscopy; electrospray ionization-mass spectrometry (ESI-MS, tandem-MS/collision-induced decay-MS, and ion trap-MS(n)); and component and methylation linkage analysis by gas chromatography-mass spectrometry. The CMH was determined to be glucosylceramide having a typical ceramide consisting of 2-hydroxy fatty-N-acylated (4E,8E)-9-methyl-sphinga-4,8-dienine. The GIPCs were identified as Manα1→2Ins1-P-1Cer (Ps-1), Galβ1→6Manα1→2Ins1-P-1Cer (Ps-2), and Manα1→3Fucα1→2Galα1→6Galβ1→6Manα1→2Ins1-P-1Cer (Ps-5), respectively (where Ins = myo-inositol, P = phosphodiester, and Cer = ceramide consisting mainly of long-chain 2-hydroxy and 2,3-dihydroxy fatty-N-acylated 4-hydroxy-sphinganines). Of these GSLs, Ps-2 could potentially interact with P. squamosus lectin, and further investigations will focus on determining the binding affinity, if any, of the lectin for the GIPCs isolated from this fungus.

  NMR spectroscopy, mass spectrometry, glycolipid, Electrospray Ionization, Basidiomycete

  NCBI PubMed ID: 17395693
  Publication DOI: 10.1093/glycob/cwm035
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Correspondence: slevery@cisunix.unh.edu (Steven B Levery)
  Institutions: Department of Chemistry, University of New Hampshire, Durham, North Carolina, USA, Department of Biochemistry and Molecular Biology, The Complex Carbohydrate Research Center, University of Georgia, Athens, Georgia, USA, Department of Biological Chemistry, School of Medicine, University of Michigan, Ann Arbor, Michigan, USA
  Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, composition analysis, CID-MS/MS, HPLC, extraction, HPTLC, ESI-QTOF-MS, MALDI-QIT-TOF-MS
  
   
  
  Polyporus squamosus
  CSDB ID 42019 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycosphingolipid, glycosylinositolphosphoceramide (GIPC)
Contained glycoepitopes: IEDB_115015,IEDB_130701,IEDB_134624,IEDB_136044,IEDB_136045,IEDB_136906,IEDB_137472,IEDB_1394182,IEDB_141794,IEDB_142489,IEDB_144562,IEDB_144983,IEDB_149135,IEDB_151528,IEDB_152206,IEDB_152214,IEDB_153553,IEDB_174333,IEDB_190606,IEDB_742248,IEDB_983930,SB_154,SB_163,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_86,SB_88

• Article ID: 7128
  Arigi E, Singh S, Kahlili AH, Winter HC, Goldstein IJ, Levery SB "Characterization of neutral and acidic glycosphingolipids from the lectin-producing mushroom, Polyporus squamosus" - Glycobiology 17(7) (2007) 754-766
  

  The polypore mushroom Polyporus squamosus is the source of a lectin that exhibits a general affinity for terminal β-galactosides, but appears to have an extended carbohydrate-binding site with high affinity and strict specificity for the nonreducing terminal trisaccharide sequence NeuAcα2→6Galβ1→4Glc/GlcNAc. In considering the possibility that the lectin's in vivo function could involve interaction with an endogenous glycoconjugate, it would clearly be helpful to identify candidate ligands among various classes of carbohydrate-containing materials expressed by P. squamosus. Since evidence has been accumulating that glycosphingolipids (GSLs) may serve as key ligands for some endogenous lectins in animal species, possible similar roles for fungal GSLs could be considered. For this study, total lipids were extracted from mature fruiting body of P. squamosus. Multistep fractionation yielded a major monohexosylceramide (CMH) component and three major glycosylinositol phosphorylceramides (GIPCs) from the neutral and acidic lipids, respectively. These were characterized by a variety of techniques as required, including one- and two-dimensional (1)H- and (13)C-nuclear magnetic resonance (NMR) spectroscopy; electrospray ionization-mass spectrometry (ESI-MS, tandem-MS/collision-induced decay-MS, and ion trap-MS(n)); and component and methylation linkage analysis by gas chromatography-mass spectrometry. The CMH was determined to be glucosylceramide having a typical ceramide consisting of 2-hydroxy fatty-N-acylated (4E,8E)-9-methyl-sphinga-4,8-dienine. The GIPCs were identified as Manα1→2Ins1-P-1Cer (Ps-1), Galβ1→6Manα1→2Ins1-P-1Cer (Ps-2), and Manα1→3Fucα1→2Galα1→6Galβ1→6Manα1→2Ins1-P-1Cer (Ps-5), respectively (where Ins = myo-inositol, P = phosphodiester, and Cer = ceramide consisting mainly of long-chain 2-hydroxy and 2,3-dihydroxy fatty-N-acylated 4-hydroxy-sphinganines). Of these GSLs, Ps-2 could potentially interact with P. squamosus lectin, and further investigations will focus on determining the binding affinity, if any, of the lectin for the GIPCs isolated from this fungus.

  NMR spectroscopy, mass spectrometry, glycolipid, Electrospray Ionization, Basidiomycete

  NCBI PubMed ID: 17395693
  Publication DOI: 10.1093/glycob/cwm035
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Correspondence: slevery@cisunix.unh.edu (Steven B Levery)
  Institutions: Department of Chemistry, University of New Hampshire, Durham, North Carolina, USA, Department of Biochemistry and Molecular Biology, The Complex Carbohydrate Research Center, University of Georgia, Athens, Georgia, USA, Department of Biological Chemistry, School of Medicine, University of Michigan, Ann Arbor, Michigan, USA
  Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, composition analysis, CID-MS/MS, HPLC, extraction, HPTLC, ESI-QTOF-MS, MALDI-QIT-TOF-MS
  
   
  
  Polyporus squamosus
  CSDB ID 42020 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycosphingolipid, glycoinositolphosphoryl ceramide (GIPC)
Contained glycoepitopes: IEDB_115013,IEDB_115015,IEDB_130645,IEDB_130701,IEDB_136044,IEDB_136045,IEDB_136906,IEDB_137472,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: 7156
  Barreto-Bergter E, Pinto MR, Rodrigues ML "Structural and Functional Aspects of Fungal Glycosphingolipids" - Book: Studies in Natural Products Chemistry (2006) 1025-1056
  

  During the last decade, significant progress has been made on the field of biosynthesis and structural elucidation of fungal glycosphingolipids (GSLs), molecules composed of a hydrophobic ceramide moiety linked to one or more sugars. Ceramide monohexosides (CMHs) from several fungal species were characterized in detail, all of them presenting a ceramide moiety containing 9-methyl-4,8-sphingadienine in amidic linkage to 2-hydroxyoctadecanoic or 2-hydroxyhexadecanoic acids, and a carbohydrate portion consisting of one residue of glucose or galactose. CMHs seem to be associated with growth or differentiation of fungal species such as Pseudallescheria boydii, Candida albicans. Cryptococcus neoformans, Aspergillus nidulans, A. fumigatus, and Schizophyllum commune. A ceramide dihexoside (CDH) was recently described in Magnaporthe grisea. This glycolipid presented phytosphingosine as the long chain base, and this observation revealed the existence of alternative pathways of ceramide glycosylation in fungal cells. Glycoinositolphosphoryl ceramides (GIPCs), a class of acidic glycosphingolipids expressed by plants and certain parasitic organisms, but not in higher animals, were also identified in fungi, representing potential targets for the development of antifungal agents. The structural characterization of GIPCs, CMHs and, more recently, CDHs from fungal cells allows therefore the design of experimental models for studies involving biosynthesis and function of these molecules.

  biosynthesis, structure, glycosphingolipids, fungi

  Publication DOI: 10.1016/S1572-5995(06)80045-1
  Publisher: New York: Elsevier
  Correspondence: Barreto-Bergter E
  Editors: Atta-ur-Rahman
  Institutions: Instituto de Microbiologia Professor Paulo de Góes, Departamento de Microbiologia Geral. Universidade Federal do Rio de Janeiro, Cidade Universitária, CCS, Rio de Janeiro, Brazil
  Methods: methylation, GC-MS, chemical analysis, ESI-MS, anion-exchange chromatography, GC, MS/MS, MALDI-TOF MS, MS, methanolysis, HPLC, GPC, CID-MS
  
   
  
  Amanita virosa
  CSDB ID 42077 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycosphingolipid, glycoinositolphosphoryl ceramide (GIPC)
Contained glycoepitopes: IEDB_115013,IEDB_115015,IEDB_130645,IEDB_130701,IEDB_131186,IEDB_135818,IEDB_136044,IEDB_136045,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142489,IEDB_144562,IEDB_144983,IEDB_149135,IEDB_149558,IEDB_151528,IEDB_152206,IEDB_152212,IEDB_152214,IEDB_153553,IEDB_174333,IEDB_190606,IEDB_742246,IEDB_918313,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: 7156
  Barreto-Bergter E, Pinto MR, Rodrigues ML "Structural and Functional Aspects of Fungal Glycosphingolipids" - Book: Studies in Natural Products Chemistry (2006) 1025-1056
  

  During the last decade, significant progress has been made on the field of biosynthesis and structural elucidation of fungal glycosphingolipids (GSLs), molecules composed of a hydrophobic ceramide moiety linked to one or more sugars. Ceramide monohexosides (CMHs) from several fungal species were characterized in detail, all of them presenting a ceramide moiety containing 9-methyl-4,8-sphingadienine in amidic linkage to 2-hydroxyoctadecanoic or 2-hydroxyhexadecanoic acids, and a carbohydrate portion consisting of one residue of glucose or galactose. CMHs seem to be associated with growth or differentiation of fungal species such as Pseudallescheria boydii, Candida albicans. Cryptococcus neoformans, Aspergillus nidulans, A. fumigatus, and Schizophyllum commune. A ceramide dihexoside (CDH) was recently described in Magnaporthe grisea. This glycolipid presented phytosphingosine as the long chain base, and this observation revealed the existence of alternative pathways of ceramide glycosylation in fungal cells. Glycoinositolphosphoryl ceramides (GIPCs), a class of acidic glycosphingolipids expressed by plants and certain parasitic organisms, but not in higher animals, were also identified in fungi, representing potential targets for the development of antifungal agents. The structural characterization of GIPCs, CMHs and, more recently, CDHs from fungal cells allows therefore the design of experimental models for studies involving biosynthesis and function of these molecules.

  biosynthesis, structure, glycosphingolipids, fungi

  Publication DOI: 10.1016/S1572-5995(06)80045-1
  Publisher: New York: Elsevier
  Correspondence: Barreto-Bergter E
  Editors: Atta-ur-Rahman
  Institutions: Instituto de Microbiologia Professor Paulo de Góes, Departamento de Microbiologia Geral. Universidade Federal do Rio de Janeiro, Cidade Universitária, CCS, Rio de Janeiro, Brazil
  Methods: methylation, GC-MS, chemical analysis, ESI-MS, anion-exchange chromatography, GC, MS/MS, MALDI-TOF MS, MS, methanolysis, HPLC, GPC, CID-MS
  
   
  
  Amanita virosa
  CSDB ID 42078 (all data & tools)

Show legend Show as text

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

• Article ID: 7156
  Barreto-Bergter E, Pinto MR, Rodrigues ML "Structural and Functional Aspects of Fungal Glycosphingolipids" - Book: Studies in Natural Products Chemistry (2006) 1025-1056
  

  During the last decade, significant progress has been made on the field of biosynthesis and structural elucidation of fungal glycosphingolipids (GSLs), molecules composed of a hydrophobic ceramide moiety linked to one or more sugars. Ceramide monohexosides (CMHs) from several fungal species were characterized in detail, all of them presenting a ceramide moiety containing 9-methyl-4,8-sphingadienine in amidic linkage to 2-hydroxyoctadecanoic or 2-hydroxyhexadecanoic acids, and a carbohydrate portion consisting of one residue of glucose or galactose. CMHs seem to be associated with growth or differentiation of fungal species such as Pseudallescheria boydii, Candida albicans. Cryptococcus neoformans, Aspergillus nidulans, A. fumigatus, and Schizophyllum commune. A ceramide dihexoside (CDH) was recently described in Magnaporthe grisea. This glycolipid presented phytosphingosine as the long chain base, and this observation revealed the existence of alternative pathways of ceramide glycosylation in fungal cells. Glycoinositolphosphoryl ceramides (GIPCs), a class of acidic glycosphingolipids expressed by plants and certain parasitic organisms, but not in higher animals, were also identified in fungi, representing potential targets for the development of antifungal agents. The structural characterization of GIPCs, CMHs and, more recently, CDHs from fungal cells allows therefore the design of experimental models for studies involving biosynthesis and function of these molecules.

  biosynthesis, structure, glycosphingolipids, fungi

  Publication DOI: 10.1016/S1572-5995(06)80045-1
  Publisher: New York: Elsevier
  Correspondence: Barreto-Bergter E
  Editors: Atta-ur-Rahman
  Institutions: Instituto de Microbiologia Professor Paulo de Góes, Departamento de Microbiologia Geral. Universidade Federal do Rio de Janeiro, Cidade Universitária, CCS, Rio de Janeiro, Brazil
  Methods: methylation, GC-MS, chemical analysis, ESI-MS, anion-exchange chromatography, GC, MS/MS, MALDI-TOF MS, MS, methanolysis, HPLC, GPC, CID-MS
  
   
  
  Calvatia excipuliformis, Pleurotus ostreatus, Lentinus edodes
  CSDB ID 42079 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycosphingolipid, glycoinositolphosphoryl ceramide (GIPC)
Contained glycoepitopes: IEDB_130701,IEDB_136044,IEDB_137472,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: 7156
  Barreto-Bergter E, Pinto MR, Rodrigues ML "Structural and Functional Aspects of Fungal Glycosphingolipids" - Book: Studies in Natural Products Chemistry (2006) 1025-1056
  

  During the last decade, significant progress has been made on the field of biosynthesis and structural elucidation of fungal glycosphingolipids (GSLs), molecules composed of a hydrophobic ceramide moiety linked to one or more sugars. Ceramide monohexosides (CMHs) from several fungal species were characterized in detail, all of them presenting a ceramide moiety containing 9-methyl-4,8-sphingadienine in amidic linkage to 2-hydroxyoctadecanoic or 2-hydroxyhexadecanoic acids, and a carbohydrate portion consisting of one residue of glucose or galactose. CMHs seem to be associated with growth or differentiation of fungal species such as Pseudallescheria boydii, Candida albicans. Cryptococcus neoformans, Aspergillus nidulans, A. fumigatus, and Schizophyllum commune. A ceramide dihexoside (CDH) was recently described in Magnaporthe grisea. This glycolipid presented phytosphingosine as the long chain base, and this observation revealed the existence of alternative pathways of ceramide glycosylation in fungal cells. Glycoinositolphosphoryl ceramides (GIPCs), a class of acidic glycosphingolipids expressed by plants and certain parasitic organisms, but not in higher animals, were also identified in fungi, representing potential targets for the development of antifungal agents. The structural characterization of GIPCs, CMHs and, more recently, CDHs from fungal cells allows therefore the design of experimental models for studies involving biosynthesis and function of these molecules.

  biosynthesis, structure, glycosphingolipids, fungi

  Publication DOI: 10.1016/S1572-5995(06)80045-1
  Publisher: New York: Elsevier
  Correspondence: Barreto-Bergter E
  Editors: Atta-ur-Rahman
  Institutions: Instituto de Microbiologia Professor Paulo de Góes, Departamento de Microbiologia Geral. Universidade Federal do Rio de Janeiro, Cidade Universitária, CCS, Rio de Janeiro, Brazil
  Methods: methylation, GC-MS, chemical analysis, ESI-MS, anion-exchange chromatography, GC, MS/MS, MALDI-TOF MS, MS, methanolysis, HPLC, GPC, CID-MS
  
   
  
  Calvatia excipuliformis
  CSDB ID 42080 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycosphingolipid, glycoinositolphosphoryl ceramide (GIPC)
Contained glycoepitopes: IEDB_130701,IEDB_134624,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_742248,IEDB_983930,SB_163,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_88

• Article ID: 7156
  Barreto-Bergter E, Pinto MR, Rodrigues ML "Structural and Functional Aspects of Fungal Glycosphingolipids" - Book: Studies in Natural Products Chemistry (2006) 1025-1056
  

  During the last decade, significant progress has been made on the field of biosynthesis and structural elucidation of fungal glycosphingolipids (GSLs), molecules composed of a hydrophobic ceramide moiety linked to one or more sugars. Ceramide monohexosides (CMHs) from several fungal species were characterized in detail, all of them presenting a ceramide moiety containing 9-methyl-4,8-sphingadienine in amidic linkage to 2-hydroxyoctadecanoic or 2-hydroxyhexadecanoic acids, and a carbohydrate portion consisting of one residue of glucose or galactose. CMHs seem to be associated with growth or differentiation of fungal species such as Pseudallescheria boydii, Candida albicans. Cryptococcus neoformans, Aspergillus nidulans, A. fumigatus, and Schizophyllum commune. A ceramide dihexoside (CDH) was recently described in Magnaporthe grisea. This glycolipid presented phytosphingosine as the long chain base, and this observation revealed the existence of alternative pathways of ceramide glycosylation in fungal cells. Glycoinositolphosphoryl ceramides (GIPCs), a class of acidic glycosphingolipids expressed by plants and certain parasitic organisms, but not in higher animals, were also identified in fungi, representing potential targets for the development of antifungal agents. The structural characterization of GIPCs, CMHs and, more recently, CDHs from fungal cells allows therefore the design of experimental models for studies involving biosynthesis and function of these molecules.

  biosynthesis, structure, glycosphingolipids, fungi

  Publication DOI: 10.1016/S1572-5995(06)80045-1
  Publisher: New York: Elsevier
  Correspondence: Barreto-Bergter E
  Editors: Atta-ur-Rahman
  Institutions: Instituto de Microbiologia Professor Paulo de Góes, Departamento de Microbiologia Geral. Universidade Federal do Rio de Janeiro, Cidade Universitária, CCS, Rio de Janeiro, Brazil
  Methods: methylation, GC-MS, chemical analysis, ESI-MS, anion-exchange chromatography, GC, MS/MS, MALDI-TOF MS, MS, methanolysis, HPLC, GPC, CID-MS
  
   
  
  Calvatia excipuliformis
  CSDB ID 42081 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycosphingolipid, glycoinositolphosphoryl ceramide (GIPC)
Contained glycoepitopes: IEDB_115013,IEDB_115015,IEDB_130645,IEDB_130701,IEDB_134624,IEDB_136044,IEDB_136045,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142489,IEDB_144562,IEDB_144983,IEDB_149135,IEDB_150948,IEDB_151528,IEDB_152206,IEDB_152214,IEDB_153553,IEDB_174333,IEDB_190606,IEDB_461719,IEDB_742246,IEDB_742248,IEDB_918313,IEDB_983930,SB_154,SB_163,SB_165,SB_166,SB_187,SB_195,SB_44,SB_67,SB_7,SB_72,SB_86,SB_87,SB_88

• Article ID: 7156
  Barreto-Bergter E, Pinto MR, Rodrigues ML "Structural and Functional Aspects of Fungal Glycosphingolipids" - Book: Studies in Natural Products Chemistry (2006) 1025-1056
  

  During the last decade, significant progress has been made on the field of biosynthesis and structural elucidation of fungal glycosphingolipids (GSLs), molecules composed of a hydrophobic ceramide moiety linked to one or more sugars. Ceramide monohexosides (CMHs) from several fungal species were characterized in detail, all of them presenting a ceramide moiety containing 9-methyl-4,8-sphingadienine in amidic linkage to 2-hydroxyoctadecanoic or 2-hydroxyhexadecanoic acids, and a carbohydrate portion consisting of one residue of glucose or galactose. CMHs seem to be associated with growth or differentiation of fungal species such as Pseudallescheria boydii, Candida albicans. Cryptococcus neoformans, Aspergillus nidulans, A. fumigatus, and Schizophyllum commune. A ceramide dihexoside (CDH) was recently described in Magnaporthe grisea. This glycolipid presented phytosphingosine as the long chain base, and this observation revealed the existence of alternative pathways of ceramide glycosylation in fungal cells. Glycoinositolphosphoryl ceramides (GIPCs), a class of acidic glycosphingolipids expressed by plants and certain parasitic organisms, but not in higher animals, were also identified in fungi, representing potential targets for the development of antifungal agents. The structural characterization of GIPCs, CMHs and, more recently, CDHs from fungal cells allows therefore the design of experimental models for studies involving biosynthesis and function of these molecules.

  biosynthesis, structure, glycosphingolipids, fungi

  Publication DOI: 10.1016/S1572-5995(06)80045-1
  Publisher: New York: Elsevier
  Correspondence: Barreto-Bergter E
  Editors: Atta-ur-Rahman
  Institutions: Instituto de Microbiologia Professor Paulo de Góes, Departamento de Microbiologia Geral. Universidade Federal do Rio de Janeiro, Cidade Universitária, CCS, Rio de Janeiro, Brazil
  Methods: methylation, GC-MS, chemical analysis, ESI-MS, anion-exchange chromatography, GC, MS/MS, MALDI-TOF MS, MS, methanolysis, HPLC, GPC, CID-MS
  
   
  
  Calvatia excipuliformis, Pleurotus ostreatus
  CSDB ID 42082 (all data & tools)