Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153758,IEDB_158540,IEDB_190606,IEDB_688614,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_66,SB_69,SB_7,SB_88

• Article ID: 2536
  Ono E, Abe K, Nakazawa M, Naiki M "Ganglioside epitope recognized by K99 fimbriae from enterotoxigenic Escherichia coli" - Infection and Immunity 57 (1989) 907-911
  

  The receptor structure recognized by Escherichia coli possessing K99 fimbriae and by isolated K99 fimbrial fractions was examined by using an equine erythrocyte hemagglutination inhibition test. Both K99-positive organisms (strain B41) and fimbrial preparations reacted with N-glycolylneuraminyl-lactosyl-ceramide (NeuGcLacCer) purified from equine erythrocytes with very high potency. Fimbrial preparations were 253 times more potent than intact organisms, indicating that isolated fimbriae more precisely recognize the structure of NeuGcLacCer than do fimbriae located on the bacterial cell wall. Structurally, the N-glycolyl group of the sialic acid was shown to be essential because substitution of the N-acetyl group for the N-glycolyl group caused the reactivity to completely disappear. The substitution of the O-acetyl group for the C4 hydroxyl group of the sialic acid (4-O-Ac-NeuGcLacCer) also diminished the reactivity by about 500 times, indicating that the fine structure of NeuGc is necessary for recognition. N-Glycolylneuraminyl-neolactotetraosyl-ceramide (NeuGcnLc4Cer) and N-glycolylneuraminyl-neolactohexaosyl-ceramide (NeuGcnLc6Cer), both of which have identical disaccharides at the nonreducing terminal and longer carbohydrate chains, showed reduced reactivity, indicating that the ceramide of NeuGcLacCer is also involved in the recognition. Indeed, NeuGcLac oligosaccharides altered by cleavage of the ceramide or the terminal sialic acid (NeuGc) showed dramatically reduced reactivities. Ten other E. coli strains (isolated from diseased calves) and two strains (isolated from diseased piglets) which possessed the same K99 antigen and various O antigens were used for the recognition test. The results obtained were similar to those mentioned above.

  NCBI PubMed ID: 2465273
  Journal NLM ID: 0246127
  Publisher: American Society for Microbiology
  Institutions: Department of Biochemistry, Faculty of Veterinary Genetics, Hokkaido University, Sapporo, Japan
  
   
  
  Escherichia coli
  CSDB ID 130227 (all data & tools)

Show legend Show as text

Structure type: oligomer
Aglycon: Ceramide
Trivial name: GM3-NeuGc, II3NeuGc-Lac-Cer
Compound class: ganglioside
Contained glycoepitopes: IEDB_136044,IEDB_137339,IEDB_137472,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_153758,IEDB_158540,IEDB_190606,IEDB_688614,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_3,SB_5,SB_6,SB_66,SB_69,SB_7,SB_88

• Article ID: 2536
  Ono E, Abe K, Nakazawa M, Naiki M "Ganglioside epitope recognized by K99 fimbriae from enterotoxigenic Escherichia coli" - Infection and Immunity 57 (1989) 907-911
  

  The receptor structure recognized by Escherichia coli possessing K99 fimbriae and by isolated K99 fimbrial fractions was examined by using an equine erythrocyte hemagglutination inhibition test. Both K99-positive organisms (strain B41) and fimbrial preparations reacted with N-glycolylneuraminyl-lactosyl-ceramide (NeuGcLacCer) purified from equine erythrocytes with very high potency. Fimbrial preparations were 253 times more potent than intact organisms, indicating that isolated fimbriae more precisely recognize the structure of NeuGcLacCer than do fimbriae located on the bacterial cell wall. Structurally, the N-glycolyl group of the sialic acid was shown to be essential because substitution of the N-acetyl group for the N-glycolyl group caused the reactivity to completely disappear. The substitution of the O-acetyl group for the C4 hydroxyl group of the sialic acid (4-O-Ac-NeuGcLacCer) also diminished the reactivity by about 500 times, indicating that the fine structure of NeuGc is necessary for recognition. N-Glycolylneuraminyl-neolactotetraosyl-ceramide (NeuGcnLc4Cer) and N-glycolylneuraminyl-neolactohexaosyl-ceramide (NeuGcnLc6Cer), both of which have identical disaccharides at the nonreducing terminal and longer carbohydrate chains, showed reduced reactivity, indicating that the ceramide of NeuGcLacCer is also involved in the recognition. Indeed, NeuGcLac oligosaccharides altered by cleavage of the ceramide or the terminal sialic acid (NeuGc) showed dramatically reduced reactivities. Ten other E. coli strains (isolated from diseased calves) and two strains (isolated from diseased piglets) which possessed the same K99 antigen and various O antigens were used for the recognition test. The results obtained were similar to those mentioned above.

  NCBI PubMed ID: 2465273
  Journal NLM ID: 0246127
  Publisher: American Society for Microbiology
  Institutions: Department of Biochemistry, Faculty of Veterinary Genetics, Hokkaido University, Sapporo, Japan
  
   
  
  Escherichia coli
  CSDB ID 130229 (all data & tools)

Show legend Show as text

Structure type: oligomer
Aglycon: Ceramide
Trivial name: GM3-Neu4Ac5Gc
Compound class: ganglioside
Contained glycoepitopes: IEDB_136044,IEDB_137339,IEDB_137472,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_153758,IEDB_158540,IEDB_190606,IEDB_688614,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_3,SB_5,SB_6,SB_66,SB_69,SB_7,SB_88

• Article ID: 2536
  Ono E, Abe K, Nakazawa M, Naiki M "Ganglioside epitope recognized by K99 fimbriae from enterotoxigenic Escherichia coli" - Infection and Immunity 57 (1989) 907-911
  

  The receptor structure recognized by Escherichia coli possessing K99 fimbriae and by isolated K99 fimbrial fractions was examined by using an equine erythrocyte hemagglutination inhibition test. Both K99-positive organisms (strain B41) and fimbrial preparations reacted with N-glycolylneuraminyl-lactosyl-ceramide (NeuGcLacCer) purified from equine erythrocytes with very high potency. Fimbrial preparations were 253 times more potent than intact organisms, indicating that isolated fimbriae more precisely recognize the structure of NeuGcLacCer than do fimbriae located on the bacterial cell wall. Structurally, the N-glycolyl group of the sialic acid was shown to be essential because substitution of the N-acetyl group for the N-glycolyl group caused the reactivity to completely disappear. The substitution of the O-acetyl group for the C4 hydroxyl group of the sialic acid (4-O-Ac-NeuGcLacCer) also diminished the reactivity by about 500 times, indicating that the fine structure of NeuGc is necessary for recognition. N-Glycolylneuraminyl-neolactotetraosyl-ceramide (NeuGcnLc4Cer) and N-glycolylneuraminyl-neolactohexaosyl-ceramide (NeuGcnLc6Cer), both of which have identical disaccharides at the nonreducing terminal and longer carbohydrate chains, showed reduced reactivity, indicating that the ceramide of NeuGcLacCer is also involved in the recognition. Indeed, NeuGcLac oligosaccharides altered by cleavage of the ceramide or the terminal sialic acid (NeuGc) showed dramatically reduced reactivities. Ten other E. coli strains (isolated from diseased calves) and two strains (isolated from diseased piglets) which possessed the same K99 antigen and various O antigens were used for the recognition test. The results obtained were similar to those mentioned above.

  NCBI PubMed ID: 2465273
  Journal NLM ID: 0246127
  Publisher: American Society for Microbiology
  Institutions: Department of Biochemistry, Faculty of Veterinary Genetics, Hokkaido University, Sapporo, Japan
  
   
  
  Escherichia coli
  CSDB ID 130230 (all data & tools)

Show legend Show as text

Structure type: oligomer
Aglycon: Ceramide
Trivial name: 3'-LM1-NeuGc
Compound class: ganglioside
Contained glycoepitopes: IEDB_130646,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_137339,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_1391966,IEDB_140108,IEDB_140110,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_149144,IEDB_151531,IEDB_153758,IEDB_190606,IEDB_983931,SB_145,SB_15,SB_165,SB_166,SB_173,SB_175,SB_187,SB_192,SB_195,SB_20,SB_201,SB_3,SB_30,SB_5,SB_6,SB_7,SB_88

• Article ID: 2536
  Ono E, Abe K, Nakazawa M, Naiki M "Ganglioside epitope recognized by K99 fimbriae from enterotoxigenic Escherichia coli" - Infection and Immunity 57 (1989) 907-911
  

  The receptor structure recognized by Escherichia coli possessing K99 fimbriae and by isolated K99 fimbrial fractions was examined by using an equine erythrocyte hemagglutination inhibition test. Both K99-positive organisms (strain B41) and fimbrial preparations reacted with N-glycolylneuraminyl-lactosyl-ceramide (NeuGcLacCer) purified from equine erythrocytes with very high potency. Fimbrial preparations were 253 times more potent than intact organisms, indicating that isolated fimbriae more precisely recognize the structure of NeuGcLacCer than do fimbriae located on the bacterial cell wall. Structurally, the N-glycolyl group of the sialic acid was shown to be essential because substitution of the N-acetyl group for the N-glycolyl group caused the reactivity to completely disappear. The substitution of the O-acetyl group for the C4 hydroxyl group of the sialic acid (4-O-Ac-NeuGcLacCer) also diminished the reactivity by about 500 times, indicating that the fine structure of NeuGc is necessary for recognition. N-Glycolylneuraminyl-neolactotetraosyl-ceramide (NeuGcnLc4Cer) and N-glycolylneuraminyl-neolactohexaosyl-ceramide (NeuGcnLc6Cer), both of which have identical disaccharides at the nonreducing terminal and longer carbohydrate chains, showed reduced reactivity, indicating that the ceramide of NeuGcLacCer is also involved in the recognition. Indeed, NeuGcLac oligosaccharides altered by cleavage of the ceramide or the terminal sialic acid (NeuGc) showed dramatically reduced reactivities. Ten other E. coli strains (isolated from diseased calves) and two strains (isolated from diseased piglets) which possessed the same K99 antigen and various O antigens were used for the recognition test. The results obtained were similar to those mentioned above.

  NCBI PubMed ID: 2465273
  Journal NLM ID: 0246127
  Publisher: American Society for Microbiology
  Institutions: Department of Biochemistry, Faculty of Veterinary Genetics, Hokkaido University, Sapporo, Japan
  
   
  
  Escherichia coli
  CSDB ID 130232 (all data & tools)

Show legend Show as text

Structure type: oligomer
Aglycon: Ceramide
Trivial name: VI3NeuGc-nLc6-Cer
Compound class: ganglioside
Contained glycoepitopes: IEDB_130646,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_137339,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_1391966,IEDB_140108,IEDB_140110,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_149144,IEDB_150939,IEDB_151531,IEDB_153758,IEDB_158549,IEDB_190606,IEDB_983931,SB_117,SB_145,SB_15,SB_165,SB_166,SB_173,SB_175,SB_187,SB_192,SB_195,SB_20,SB_201,SB_3,SB_30,SB_5,SB_6,SB_7,SB_88

• Article ID: 2536
  Ono E, Abe K, Nakazawa M, Naiki M "Ganglioside epitope recognized by K99 fimbriae from enterotoxigenic Escherichia coli" - Infection and Immunity 57 (1989) 907-911
  

  The receptor structure recognized by Escherichia coli possessing K99 fimbriae and by isolated K99 fimbrial fractions was examined by using an equine erythrocyte hemagglutination inhibition test. Both K99-positive organisms (strain B41) and fimbrial preparations reacted with N-glycolylneuraminyl-lactosyl-ceramide (NeuGcLacCer) purified from equine erythrocytes with very high potency. Fimbrial preparations were 253 times more potent than intact organisms, indicating that isolated fimbriae more precisely recognize the structure of NeuGcLacCer than do fimbriae located on the bacterial cell wall. Structurally, the N-glycolyl group of the sialic acid was shown to be essential because substitution of the N-acetyl group for the N-glycolyl group caused the reactivity to completely disappear. The substitution of the O-acetyl group for the C4 hydroxyl group of the sialic acid (4-O-Ac-NeuGcLacCer) also diminished the reactivity by about 500 times, indicating that the fine structure of NeuGc is necessary for recognition. N-Glycolylneuraminyl-neolactotetraosyl-ceramide (NeuGcnLc4Cer) and N-glycolylneuraminyl-neolactohexaosyl-ceramide (NeuGcnLc6Cer), both of which have identical disaccharides at the nonreducing terminal and longer carbohydrate chains, showed reduced reactivity, indicating that the ceramide of NeuGcLacCer is also involved in the recognition. Indeed, NeuGcLac oligosaccharides altered by cleavage of the ceramide or the terminal sialic acid (NeuGc) showed dramatically reduced reactivities. Ten other E. coli strains (isolated from diseased calves) and two strains (isolated from diseased piglets) which possessed the same K99 antigen and various O antigens were used for the recognition test. The results obtained were similar to those mentioned above.

  NCBI PubMed ID: 2465273
  Journal NLM ID: 0246127
  Publisher: American Society for Microbiology
  Institutions: Department of Biochemistry, Faculty of Veterinary Genetics, Hokkaido University, Sapporo, Japan
  
   
  
  Escherichia coli
  CSDB ID 130233 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_130648,IEDB_136794,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_153758,IEDB_241118,IEDB_885822,IEDB_983931,SB_170,SB_171,SB_172,SB_192,SB_84

• Article ID: 4599
  Perry MB, MacLean LL, Gottschalk M, Aragón V, Vinogradov E "Structure of the capsular polysaccharides and lipopolysaccharides from Haemophilus parasuis strains ER-6P (serovar 15) and Nagasaki (serovar 5)" - Carbohydrate Research 378 (2013) 91-97
  

  Haemophilus parasuis is a Gram-negative bacterium from the family Pasteurellaceae and a swine pathogen. H. parasuis is found in the upper respiratory tract of piglets and produces Glasser's disease, an invasive disease characterized by polyserositis. H. parasuis contains a short lipopolysaccharide (LPS) or lipooligosaccharide (LOS) reported to play a partial role in interaction with host cells. The presence of capsule has been phenotypically demonstrated in certain H. parasuis strains and its role in virulence has been suggested, but the chemical structure of the surface polysaccharides of this bacterium was unknown. The structure of capsular polysaccharide (CPS) and LOS from virulent strains ER-6P and Nagasaki was studied by NMR spectroscopy, mass spectrometry and chemical methods. CPS from both strains had the same main chain with disaccharide repeating unit, substituted with α-Neu5R-(2-3)-α-GalNAc-(1-P-(strain ER-6P) or α-Neu5R-(2-3)-α-Gal-(1-P-strain Nagasaki) side chains, where R is the N-acetyl or N-glycolyl group. Glycolyl-neuraminic acid is widely found in animal glycoproteins, but it apparently has not been found in bacteria before, and might be important for the biology of this microorganism. Ac and Gc were present in equal amounts in the strain ER-6P but Nagasaki contained only about 20% of Gc substituent. Both strains produced the same LPS of a rough type with a single phosphorylated Kdo linking core and lipid A parts. LOS structure was similar to some strains of H. influenzae and contained a globotetraose terminal sequence.

  Lipopolysaccharide, polysaccharide, capsule, Haemophilus parasuis

  NCBI PubMed ID: 23664728
  Publication DOI: 10.1016/j.carres.2013.04.023
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: E. Vinogradov
  Institutions: National Research Council, Ottawa, ON, Canada, Faculté de médecine vétérinaire, Université de Montréal, St-Hyacinthe, Québec, Canada, Centre de Recerca en Sanitat Animal (CReSA), UAB-IRTA, Campus de la Universitat Autònoma de Barcelona, Bellaterra (Cerdanyola del Vallès) and Institut de Recerca i Tecnología Agroalimentàries (IRTA), Barcelona, Spain
  Methods: 13C NMR, 1H NMR, NMR-2D, HF solvolysis, sugar analysis, ESI-MS, mild acid hydrolysis, alkaline degradation, GC, de-O-acylation with hydrazine, NMR-1D, methanolysis, CE-MS
  
   
  
  Haemophilus parasuis ER-6P sv. 15
  CSDB ID 29316 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_136794,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_145001,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_150933,IEDB_151528,IEDB_153758,IEDB_190606,IEDB_241118,IEDB_983931,SB_170,SB_171,SB_172,SB_192,SB_39,SB_7,SB_84

• Article ID: 4599
  Perry MB, MacLean LL, Gottschalk M, Aragón V, Vinogradov E "Structure of the capsular polysaccharides and lipopolysaccharides from Haemophilus parasuis strains ER-6P (serovar 15) and Nagasaki (serovar 5)" - Carbohydrate Research 378 (2013) 91-97
  

  Haemophilus parasuis is a Gram-negative bacterium from the family Pasteurellaceae and a swine pathogen. H. parasuis is found in the upper respiratory tract of piglets and produces Glasser's disease, an invasive disease characterized by polyserositis. H. parasuis contains a short lipopolysaccharide (LPS) or lipooligosaccharide (LOS) reported to play a partial role in interaction with host cells. The presence of capsule has been phenotypically demonstrated in certain H. parasuis strains and its role in virulence has been suggested, but the chemical structure of the surface polysaccharides of this bacterium was unknown. The structure of capsular polysaccharide (CPS) and LOS from virulent strains ER-6P and Nagasaki was studied by NMR spectroscopy, mass spectrometry and chemical methods. CPS from both strains had the same main chain with disaccharide repeating unit, substituted with α-Neu5R-(2-3)-α-GalNAc-(1-P-(strain ER-6P) or α-Neu5R-(2-3)-α-Gal-(1-P-strain Nagasaki) side chains, where R is the N-acetyl or N-glycolyl group. Glycolyl-neuraminic acid is widely found in animal glycoproteins, but it apparently has not been found in bacteria before, and might be important for the biology of this microorganism. Ac and Gc were present in equal amounts in the strain ER-6P but Nagasaki contained only about 20% of Gc substituent. Both strains produced the same LPS of a rough type with a single phosphorylated Kdo linking core and lipid A parts. LOS structure was similar to some strains of H. influenzae and contained a globotetraose terminal sequence.

  Lipopolysaccharide, polysaccharide, capsule, Haemophilus parasuis

  NCBI PubMed ID: 23664728
  Publication DOI: 10.1016/j.carres.2013.04.023
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: E. Vinogradov
  Institutions: National Research Council, Ottawa, ON, Canada, Faculté de médecine vétérinaire, Université de Montréal, St-Hyacinthe, Québec, Canada, Centre de Recerca en Sanitat Animal (CReSA), UAB-IRTA, Campus de la Universitat Autònoma de Barcelona, Bellaterra (Cerdanyola del Vallès) and Institut de Recerca i Tecnología Agroalimentàries (IRTA), Barcelona, Spain
  Methods: 13C NMR, 1H NMR, NMR-2D, HF solvolysis, sugar analysis, ESI-MS, mild acid hydrolysis, alkaline degradation, GC, de-O-acylation with hydrazine, NMR-1D, methanolysis, CE-MS
  
   
  
  Haemophilus parasuis sv. 5 Nagasaki
  CSDB ID 29719 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: CPS
Contained glycoepitopes: IEDB_136044,IEDB_136794,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_146100,IEDB_149174,IEDB_150933,IEDB_151528,IEDB_153758,IEDB_190606,SB_116,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_195,SB_39,SB_68,SB_7,SB_84,SB_88

• Article ID: 4599
  Perry MB, MacLean LL, Gottschalk M, Aragón V, Vinogradov E "Structure of the capsular polysaccharides and lipopolysaccharides from Haemophilus parasuis strains ER-6P (serovar 15) and Nagasaki (serovar 5)" - Carbohydrate Research 378 (2013) 91-97
  

  Haemophilus parasuis is a Gram-negative bacterium from the family Pasteurellaceae and a swine pathogen. H. parasuis is found in the upper respiratory tract of piglets and produces Glasser's disease, an invasive disease characterized by polyserositis. H. parasuis contains a short lipopolysaccharide (LPS) or lipooligosaccharide (LOS) reported to play a partial role in interaction with host cells. The presence of capsule has been phenotypically demonstrated in certain H. parasuis strains and its role in virulence has been suggested, but the chemical structure of the surface polysaccharides of this bacterium was unknown. The structure of capsular polysaccharide (CPS) and LOS from virulent strains ER-6P and Nagasaki was studied by NMR spectroscopy, mass spectrometry and chemical methods. CPS from both strains had the same main chain with disaccharide repeating unit, substituted with α-Neu5R-(2-3)-α-GalNAc-(1-P-(strain ER-6P) or α-Neu5R-(2-3)-α-Gal-(1-P-strain Nagasaki) side chains, where R is the N-acetyl or N-glycolyl group. Glycolyl-neuraminic acid is widely found in animal glycoproteins, but it apparently has not been found in bacteria before, and might be important for the biology of this microorganism. Ac and Gc were present in equal amounts in the strain ER-6P but Nagasaki contained only about 20% of Gc substituent. Both strains produced the same LPS of a rough type with a single phosphorylated Kdo linking core and lipid A parts. LOS structure was similar to some strains of H. influenzae and contained a globotetraose terminal sequence.

  Lipopolysaccharide, polysaccharide, capsule, Haemophilus parasuis

  NCBI PubMed ID: 23664728
  Publication DOI: 10.1016/j.carres.2013.04.023
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: E. Vinogradov
  Institutions: National Research Council, Ottawa, ON, Canada, Faculté de médecine vétérinaire, Université de Montréal, St-Hyacinthe, Québec, Canada, Centre de Recerca en Sanitat Animal (CReSA), UAB-IRTA, Campus de la Universitat Autònoma de Barcelona, Bellaterra (Cerdanyola del Vallès) and Institut de Recerca i Tecnología Agroalimentàries (IRTA), Barcelona, Spain
  Methods: 13C NMR, 1H NMR, NMR-2D, HF solvolysis, sugar analysis, ESI-MS, mild acid hydrolysis, alkaline degradation, GC, de-O-acylation with hydrazine, NMR-1D, methanolysis, CE-MS
  
   
  
  Haemophilus parasuis sv. 5 Nagasaki, Haemophilus parasuis sv. 15 ER-6P
  CSDB ID 29722 (all data & tools)

Show legend Show as text

Structure type: monomer
Compound class: sialic acid
Contained glycoepitopes: IEDB_153758

• Article ID: 7409
  Takata T, Hasegawa T, Tatsuno T, Date J, Ishigaki Y, Nakamura Y, Tomosugi N, Takano F, Ohta T "Isolation of N-acetylneuraminic acid and N-glycolylneuraminic acid from Pleurocybella porrigens" - Journal of Health Science 55(3) (2009) 373-379
  

  Pleurocybella porrigens (P. porrigens) is a traditional food consumed in Japan. Toxicity was first reported in 2004, following which a series of poisonings were reported in 2007. More than 59 people who consumed P. porrigens suffered from similar severe cryptogenic encephalitis, with an overall death rate of approximately 29%. P. porrigens is believed to be a major etiological agent of this disease, but the mechanism of pathogenesis is not clear. To elucidate the toxic properties of P. porrigens in the 2004 and 2007 poisonings, we compared the oligosaccharide constituents of mushroom samples collected in these years with those collected in other years. Water extracts (90°C and 4°C) of P. porrigens were dialyzed, and the oligosaccharides obtained from the high-molecular-weight fraction (>7.8 kDa) were subjected to acid hydrolysis for modification and labeling. Resultant saccharides were analyzed by high performance liquid chromatography on an octadecyl silane (ODS) column. Our analysis revealed that the concentration of N-acetylneuraminic acid (NeuAc) was abundant in all samples, however, N-glycolylneuraminic acid (NeuGc) was present only in significant amounts in the P. porrigens samples collected in 2004 and 2007.

  sialic acid, N-acetylneuraminic acid, N-glycolylneuraminic acid, Pleurocybella porrigens, encephalopathy

  Publication DOI: 10.1248/jhs.55.373
  Journal NLM ID: 100895795
  Publisher: Tokyo: Pharmaceutical Society of Japan
  Correspondence: Takata T
  Institutions: High-Tech Research Center, Kanazawa Medical University, Kahoku, Japan, Department of Pharmacognosy and Chemistry of Natural Products, Graduate School of Natural Science and Technology, Kanazawa University, Kanazawa, Japan, Division of Core Facility, Medical Research Institute, Kanazawa Medical University, Kahoku, Japan, MCProt Biotechnology Company Limited, Kahoku, Japan, Division of Advanced Medicine, Medical Research Institute, Kanazawa Medical University, Kahoku, Japan
  Methods: SDS-PAGE, HPLC, extraction, column chromatography, evaporation, HR-FAB-MS, phospho-phenol method
  
   
  
  Pleurocybella porrigens
  CSDB ID 44396 (all data & tools)

Show legend Show as text

Structure type: monomer
Contained glycoepitopes: IEDB_153193,IEDB_153758

• Article ID: 7571
  Chen HP, Liu JK "Secondary metabolites from higher fungi" - Progress in the Chemistry of Organic Natural Products 106 (2017) 1-201
  

  Secondary metabolites of higher fungi (mushrooms) are an underexplored resource compared to plant-derived secondary metabolites. An increasing interest in mushroom natural products has been noted in recent years. This chapter gives a comprehensive overview of the secondary metabolites from higher fungi, with 765 references highlighting the isolation, structure elucidation, biological activities, chemical syntheses, and biosynthesis of pigments, nitrogen-containing compounds, and terpenoids from mushrooms. Mushroom toxins are also included in each section.In a section on pigments of higher fungi, pigments are classified into four categories, namely, those from the shikimate-chorismate, acetate-malonate, and mevalonate biosynthetic pathways, and pigments containing nitrogen, with 145 references covering the years 2010-2016.In a section on other nitrogen-containing compounds of higher fungi, compounds are categorized primarily into nitrogen heterocycles, nucleosides, non-protein amino acids, cyclic peptides, and sphingolipids, with 65 references covering the years 2010-2016. In turn, in a section describing terpenoids of higher fungi, the sesquiterpenoids and diterpenoids are thoroughly elaborated, spanning the years 2001-2016, and 2009-2016, respectively. The divergent biosynthetic pathways from farnesyl pyrophosphate to sesquiterpenoids are also described. Selected triterpenoids with novel structures and promising biological activities, including lanostanes and ergostanes, are reported from the genus Ganoderma, and the fungi Antrodia cinnamomea and Poria cocos. In addition, cucurbitanes and saponaceolides are also compiled in this section.

  biosynthesis, biological activity, chemical synthesis, mushrooms, secondary metabolites, higher fungi, triterpenoids, diterpenoids, mushroom toxins, nitrogen-containing compounds, pigments, sesquiterpenoids

  NCBI PubMed ID: 28762089
  Publication DOI: 10.1007/978-3-319-59542-9_1
  Journal NLM ID: 101605200
  Publisher: Wien: Springer
  Correspondence: liujikai@mail.scuec.edu.cn
  Institutions: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China, School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan, China
  
   
  
  Pleurocybella porrigens
  CSDB ID 44588 (all data & tools)