Show legend Show as text

Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_136095,IEDB_137472,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_149137,IEDB_190606,IEDB_885812,IEDB_983931,SB_192

• Article ID: 2277
  Daffé M, McNeil M, Brennan PJ "Major structural features of the cell wall arabinogalactans of Mycobacterium, Rhodococcus, and Nocardia spp." - Carbohydrate Research 249 (1993) 383-398
  

  The cell wall arabinogalactans of strains of Mycobacterium, Rhodococcus, and Nocardia were per-O-methylated, partially hydrolyzed with acid, and the resulting oligosaccharides were reduced and per-O-ethylated to yield per-O-alkylated oligoglycosyl alditol fragments. Analyses of these fragments by gas chromatography-mass spectrometry and of the intact solubilized polysaccharides by 1H and 13C NMR revealed the major structural features of the different arabinogalactans from representatives of the different genera. All of the mycobacterial products contained a homogalactan segment of alternating 5-linked α-Galactofuranosyl (Galf) and 6-linked β-Galf residues. The arabinan segment consisted of three major domains, linear 5-linked α-arabinofuranosyl (Araf) residues and branched (3→5)-linked Araf units substituted with either 5-linked Araf or the disaccharide β-Araf-(1→2)-α-Araf at both branched positions. The recognition of these features in in vivo grown Mycobacterium leprae is an important development. The arabinan from strains of Nocardia contains a nonreducing-end motif composed of the linear trisaccharide, β-Araf-(1→2)-α-Araf-(1→5)-Araf, attached to linear 5-linked α-Araf units. The galactan segment of the arabinogalactan of Nocardia sp. is composed of linear 5-linked β-Galf units substituted in part at O-6 with terminal β-glucosyl units. The two representative strains of Rhodococcus also differed in the composition of the galactan moiety; in addition to the 5-linked Galf, 2- and 3-linked β-Galf units are present. The reducing end of the galactans, and therefore, apparently, of the entire arabinogalactans from all species from all genera, are apparently composed of the unit, rhamnosyl-(1→3)-N-acetyl-glucosamine, which, in turn, is apparently attached to peptidoglycan via phosphodiester linkage.

  NCBI PubMed ID: 8275507
  Publication DOI: 10.1016/0008-6215(93)84102-C
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523
  Methods: 13C NMR, 1H NMR, GLC-MS
  
   
  
  Nocardia brasiliensis ATCC 19296, Nocardia asteroides
  CSDB ID 117498 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: lipopeptidophosphoglycan
Contained glycoepitopes: IEDB_130701,IEDB_136095,IEDB_136104,IEDB_137472,IEDB_1394182,IEDB_140116,IEDB_141793,IEDB_141807,IEDB_141829,IEDB_141830,IEDB_141832,IEDB_143632,IEDB_144983,IEDB_151531,IEDB_152206,IEDB_153220,IEDB_176772,IEDB_190606,IEDB_76933,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72

• Article ID: 4262
  de Lederkremer RM, Lima C, Vila MdC "Ceramide 1-phosphate is released from a glycoinositolphosphoceramide of Trypanosoma cruzi by rat blood plasma" - Molecular and Biochemical Parasitology 79(2) (1996) 219-223
  

  No abstract

  glycosylphosphatidylinositol phospholipase D, glycoinositolphosphoceramide, Trypanosoma cruzi, lipopeptidophosphoglycan

  NCBI PubMed ID: 8855558
  Publication DOI: 10.1016/0166-6851(96)02644-8
  Journal NLM ID: 8006324
  Institutions: Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina, Departamento de Química Biológica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina
  Methods: TLC, fluorography
  
   
  
  Trypanosoma cruzi
  CSDB ID 11404 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycoinositol phospholipid
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130701,IEDB_136095,IEDB_136104,IEDB_137472,IEDB_1394182,IEDB_140116,IEDB_141795,IEDB_141807,IEDB_141830,IEDB_143632,IEDB_144983,IEDB_151531,IEDB_152206,IEDB_164480,IEDB_190606,IEDB_474450,IEDB_76933,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72

• Article ID: 4264
  DosReis GA, Peçanha LM, Bellio M, Previato JO, Mendonça-Previatoa L "Glycoinositol phospholipids from Trypanosoma cruzi transmit signals to the cells of the host immune system through both ceramide and glycan chains" - Microbes and Infection / Institut Pasteur 4(9) (2002) 1007-1013
  

  Chagas' disease is a chronic disease affecting millions of people in Latin America. The cell surface of Trypanosoma cruzi, the etiological agent, is covered by a glycocalyx whose components play important roles in parasite survival and infectivity. The most abundant surface component is a glycolipid (glycoinositol phospholipid, GIPL) related in structure to glycosylphosphatidyl inositol anchors. In this review, we describe the biological effects of highly purified native GIPLs and their glycan or lipid moities on cells of the host immune system.

  macrophage, Lymphocytes, Trypanosoma cruzi, glycoinositolphospholipids, natural killer

  NCBI PubMed ID: 12106795
  Publication DOI: 10.1016/S1286-4579(02)01616-7
  Journal NLM ID: 100883508
  Publisher: Paris, New York: Elsevier
  Institutions: Instituto de Biofísica Carlos Chagas Filho, Centro de Ciências da Saúde, Bloco G, Universidade Federal do Rio de Janeiro, Cidade Universitária, Ilha do Fundão, Rio de Janeiro, RJ 21944-970, Brazil, Instituto de Microbiologia, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ 21944-970, Brazil
  
   
  
  Trypanosoma cruzi G, Trypanosoma cruzi G-645
  CSDB ID 11436 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycoinositol phospholipid
Contained glycoepitopes: IEDB_130701,IEDB_136095,IEDB_136104,IEDB_137472,IEDB_1394182,IEDB_140116,IEDB_141795,IEDB_141807,IEDB_141830,IEDB_143632,IEDB_144983,IEDB_151531,IEDB_152206,IEDB_164480,IEDB_190606,IEDB_76933,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72

• Article ID: 4264
  DosReis GA, Peçanha LM, Bellio M, Previato JO, Mendonça-Previatoa L "Glycoinositol phospholipids from Trypanosoma cruzi transmit signals to the cells of the host immune system through both ceramide and glycan chains" - Microbes and Infection / Institut Pasteur 4(9) (2002) 1007-1013
  

  Chagas' disease is a chronic disease affecting millions of people in Latin America. The cell surface of Trypanosoma cruzi, the etiological agent, is covered by a glycocalyx whose components play important roles in parasite survival and infectivity. The most abundant surface component is a glycolipid (glycoinositol phospholipid, GIPL) related in structure to glycosylphosphatidyl inositol anchors. In this review, we describe the biological effects of highly purified native GIPLs and their glycan or lipid moities on cells of the host immune system.

  macrophage, Lymphocytes, Trypanosoma cruzi, glycoinositolphospholipids, natural killer

  NCBI PubMed ID: 12106795
  Publication DOI: 10.1016/S1286-4579(02)01616-7
  Journal NLM ID: 100883508
  Publisher: Paris, New York: Elsevier
  Institutions: Instituto de Biofísica Carlos Chagas Filho, Centro de Ciências da Saúde, Bloco G, Universidade Federal do Rio de Janeiro, Cidade Universitária, Ilha do Fundão, Rio de Janeiro, RJ 21944-970, Brazil, Instituto de Microbiologia, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ 21944-970, Brazil
  
   
  
  Trypanosoma cruzi Y, Trypanosoma cruzi CL
  CSDB ID 15014 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycoinositol phospholipid
Contained glycoepitopes: IEDB_130701,IEDB_136095,IEDB_136104,IEDB_137472,IEDB_1394182,IEDB_140116,IEDB_141795,IEDB_141807,IEDB_141830,IEDB_143632,IEDB_144983,IEDB_151531,IEDB_152206,IEDB_164480,IEDB_190606,IEDB_76933,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72

• Article ID: 4264
  DosReis GA, Peçanha LM, Bellio M, Previato JO, Mendonça-Previatoa L "Glycoinositol phospholipids from Trypanosoma cruzi transmit signals to the cells of the host immune system through both ceramide and glycan chains" - Microbes and Infection / Institut Pasteur 4(9) (2002) 1007-1013
  

  Chagas' disease is a chronic disease affecting millions of people in Latin America. The cell surface of Trypanosoma cruzi, the etiological agent, is covered by a glycocalyx whose components play important roles in parasite survival and infectivity. The most abundant surface component is a glycolipid (glycoinositol phospholipid, GIPL) related in structure to glycosylphosphatidyl inositol anchors. In this review, we describe the biological effects of highly purified native GIPLs and their glycan or lipid moities on cells of the host immune system.

  macrophage, Lymphocytes, Trypanosoma cruzi, glycoinositolphospholipids, natural killer

  NCBI PubMed ID: 12106795
  Publication DOI: 10.1016/S1286-4579(02)01616-7
  Journal NLM ID: 100883508
  Publisher: Paris, New York: Elsevier
  Institutions: Instituto de Biofísica Carlos Chagas Filho, Centro de Ciências da Saúde, Bloco G, Universidade Federal do Rio de Janeiro, Cidade Universitária, Ilha do Fundão, Rio de Janeiro, RJ 21944-970, Brazil, Instituto de Microbiologia, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ 21944-970, Brazil
  
   
  
  Trypanosoma cruzi Y, Trypanosoma cruzi CL
  CSDB ID 15015 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycoinositol phospholipid
Contained glycoepitopes: IEDB_130701,IEDB_136095,IEDB_136104,IEDB_137472,IEDB_1394182,IEDB_140116,IEDB_141807,IEDB_141830,IEDB_143632,IEDB_144983,IEDB_151531,IEDB_152206,IEDB_190606,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72

• Article ID: 4264
  DosReis GA, Peçanha LM, Bellio M, Previato JO, Mendonça-Previatoa L "Glycoinositol phospholipids from Trypanosoma cruzi transmit signals to the cells of the host immune system through both ceramide and glycan chains" - Microbes and Infection / Institut Pasteur 4(9) (2002) 1007-1013
  

  Chagas' disease is a chronic disease affecting millions of people in Latin America. The cell surface of Trypanosoma cruzi, the etiological agent, is covered by a glycocalyx whose components play important roles in parasite survival and infectivity. The most abundant surface component is a glycolipid (glycoinositol phospholipid, GIPL) related in structure to glycosylphosphatidyl inositol anchors. In this review, we describe the biological effects of highly purified native GIPLs and their glycan or lipid moities on cells of the host immune system.

  macrophage, Lymphocytes, Trypanosoma cruzi, glycoinositolphospholipids, natural killer

  NCBI PubMed ID: 12106795
  Publication DOI: 10.1016/S1286-4579(02)01616-7
  Journal NLM ID: 100883508
  Publisher: Paris, New York: Elsevier
  Institutions: Instituto de Biofísica Carlos Chagas Filho, Centro de Ciências da Saúde, Bloco G, Universidade Federal do Rio de Janeiro, Cidade Universitária, Ilha do Fundão, Rio de Janeiro, RJ 21944-970, Brazil, Instituto de Microbiologia, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ 21944-970, Brazil
  
   
  
  Trypanosoma cruzi Y
  CSDB ID 15016 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_149176,IEDB_151528,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88

• Article ID: 6616
  Iwahara S, Mishima T, Ramli N, Takegawa K "Degradation of b1-6 galactofuranoside linkages in the polysaccharide of Fusarium sp. M7-1 by endo-b-galactofuranosidase from Bacillus sp." - Bioscience, Biotechnology, and Biochemistry 60 (1996) 957-961
  
  Journal NLM ID: 9205717
  Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry
  Methods: 13C NMR, 1H NMR, methylation, GC-MS, CC
  
   
  
  Fusarium sp. M7-1
  CSDB ID 111499 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_149176,IEDB_151528,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88

• Article ID: 6616
  Iwahara S, Mishima T, Ramli N, Takegawa K "Degradation of b1-6 galactofuranoside linkages in the polysaccharide of Fusarium sp. M7-1 by endo-b-galactofuranosidase from Bacillus sp." - Bioscience, Biotechnology, and Biochemistry 60 (1996) 957-961
  
  Journal NLM ID: 9205717
  Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry
  Methods: 13C NMR, 1H NMR, methylation, GC-MS, CC
  
   
  
  Fusarium sp. M7-1
  CSDB ID 111500 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_149176,IEDB_151528,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88

• Article ID: 6616
  Iwahara S, Mishima T, Ramli N, Takegawa K "Degradation of b1-6 galactofuranoside linkages in the polysaccharide of Fusarium sp. M7-1 by endo-b-galactofuranosidase from Bacillus sp." - Bioscience, Biotechnology, and Biochemistry 60 (1996) 957-961
  
  Journal NLM ID: 9205717
  Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry
  Methods: 13C NMR, 1H NMR, methylation, GC-MS, CC
  
   
  
  Fusarium sp. M7-1
  CSDB ID 111501 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_149176,IEDB_151528,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88

• Article ID: 6616
  Iwahara S, Mishima T, Ramli N, Takegawa K "Degradation of b1-6 galactofuranoside linkages in the polysaccharide of Fusarium sp. M7-1 by endo-b-galactofuranosidase from Bacillus sp." - Bioscience, Biotechnology, and Biochemistry 60 (1996) 957-961
  
  Journal NLM ID: 9205717
  Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry
  Methods: 13C NMR, 1H NMR, methylation, GC-MS, CC
  
   
  
  Fusarium sp. M7-1
  CSDB ID 111502 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_149176,IEDB_151528,IEDB_190606,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88

• Article ID: 6616
  Iwahara S, Mishima T, Ramli N, Takegawa K "Degradation of b1-6 galactofuranoside linkages in the polysaccharide of Fusarium sp. M7-1 by endo-b-galactofuranosidase from Bacillus sp." - Bioscience, Biotechnology, and Biochemistry 60 (1996) 957-961
  
  Journal NLM ID: 9205717
  Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry
  Methods: 13C NMR, 1H NMR, methylation, GC-MS, CC
  
   
  
  Fusarium sp. M7-1
  CSDB ID 111503 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_136095,IEDB_137472,IEDB_190606

• Article ID: 6616
  Iwahara S, Mishima T, Ramli N, Takegawa K "Degradation of b1-6 galactofuranoside linkages in the polysaccharide of Fusarium sp. M7-1 by endo-b-galactofuranosidase from Bacillus sp." - Bioscience, Biotechnology, and Biochemistry 60 (1996) 957-961
  
  Journal NLM ID: 9205717
  Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry
  Methods: 13C NMR, 1H NMR, methylation, GC-MS, CC
  
   
  
  Fusarium sp. M7-1
  CSDB ID 111504 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Trivial name: galactomannan
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_130701,IEDB_136095,IEDB_136104,IEDB_137472,IEDB_1394182,IEDB_140116,IEDB_141793,IEDB_141795,IEDB_141829,IEDB_141830,IEDB_141832,IEDB_141833,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_153220,IEDB_164480,IEDB_190606,IEDB_76933,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72

• Article ID: 6860
  Ikuta K, Shibata N, Blake JS, Dahl MV, Nelson RD, Hisamichi K, Kobayashi H, Suzuki S, Okawa Y "NMR study of the galactomannans of Trichophyton mentagrophytes and Trichophyton rubrum" - Biochemical Journal 323(Pt1) (1997) 297-305
  

  Around 90% of chronic dermatophyte infections are caused by the fungi Trichophyton mentagrophytes and Trichophyton rubrum. One of the causes of the chronic infection resides in the immunosuppressive effects of the cell-wall components of these organisms. Therefore we have attempted to identify the chemical structure of galactomannan, one of the major cell-wall components. The cell-wall polysaccharides secreted by T. mentagrophytes and T. rubrum were isolated from the culture medium and fractionated into three subfractions by DEAE-Sephadex chromatography. Analysis of each subfraction by NMR indicated that there are two kinds of polysaccharides present, i.e. mannan and galactomannan. The mannan has a linear backbone consisting of α1,6-linked mannose units, with α1,2-linked mannose units as side chains. The core mannan moiety of the galactomannan was analysed by a sequential NMR assignment method after removing the galactofuranose units by acid treatment. The result indicates that the mannan moiety has a linear repeating structure of α1,2-linked mannotetraose units connected by an α1,6 linkage. The H-1 signals of the two intermediary α1,2-linked mannoses of the tetraose unit showed a significant upfield shift (Deltadelta=0.05-0.08 p.p.m.), due to the steric effect of an α1,6-linked mannose unit. The attachment point of the galactofuranose units was determined at C-3 of the core mannan by the assignment of the downfield-shifted 13C signals of the galactomannan compared with those of the acid-modified product. In these galactomannans there were no polygalactofuranosyl chains which have been found in Penicillium charlesii and Aspergillus fumigatus.

  NCBI PubMed ID: 9173896
  Journal NLM ID: 2984726R
  Publisher: London, UK : Published by Portland Press on behalf of the Biochemical Society
  Institutions: Second Department of Hygienic Chemistry, Tohoku College of Pharmacy, 4-4-1 Komatsushima, Aoba-ku, Sendai, Miyagi 981, Japan
  Methods: 13C NMR, 1H NMR, NMR-2D, acid hydrolysis, Smith degradation
  
   
  
  Trichophyton mentagrophytes IFO 5466, Trichophyton rubrum IFO 5467
  CSDB ID 40024 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Trivial name: galactomannan
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_130701,IEDB_136095,IEDB_136104,IEDB_137472,IEDB_1394182,IEDB_140116,IEDB_141793,IEDB_141795,IEDB_141829,IEDB_141830,IEDB_141832,IEDB_141833,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_153220,IEDB_164480,IEDB_190606,IEDB_76933,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72

• Article ID: 6860
  Ikuta K, Shibata N, Blake JS, Dahl MV, Nelson RD, Hisamichi K, Kobayashi H, Suzuki S, Okawa Y "NMR study of the galactomannans of Trichophyton mentagrophytes and Trichophyton rubrum" - Biochemical Journal 323(Pt1) (1997) 297-305
  

  Around 90% of chronic dermatophyte infections are caused by the fungi Trichophyton mentagrophytes and Trichophyton rubrum. One of the causes of the chronic infection resides in the immunosuppressive effects of the cell-wall components of these organisms. Therefore we have attempted to identify the chemical structure of galactomannan, one of the major cell-wall components. The cell-wall polysaccharides secreted by T. mentagrophytes and T. rubrum were isolated from the culture medium and fractionated into three subfractions by DEAE-Sephadex chromatography. Analysis of each subfraction by NMR indicated that there are two kinds of polysaccharides present, i.e. mannan and galactomannan. The mannan has a linear backbone consisting of α1,6-linked mannose units, with α1,2-linked mannose units as side chains. The core mannan moiety of the galactomannan was analysed by a sequential NMR assignment method after removing the galactofuranose units by acid treatment. The result indicates that the mannan moiety has a linear repeating structure of α1,2-linked mannotetraose units connected by an α1,6 linkage. The H-1 signals of the two intermediary α1,2-linked mannoses of the tetraose unit showed a significant upfield shift (Deltadelta=0.05-0.08 p.p.m.), due to the steric effect of an α1,6-linked mannose unit. The attachment point of the galactofuranose units was determined at C-3 of the core mannan by the assignment of the downfield-shifted 13C signals of the galactomannan compared with those of the acid-modified product. In these galactomannans there were no polygalactofuranosyl chains which have been found in Penicillium charlesii and Aspergillus fumigatus.

  NCBI PubMed ID: 9173896
  Journal NLM ID: 2984726R
  Publisher: London, UK : Published by Portland Press on behalf of the Biochemical Society
  Institutions: Second Department of Hygienic Chemistry, Tohoku College of Pharmacy, 4-4-1 Komatsushima, Aoba-ku, Sendai, Miyagi 981, Japan
  Methods: 13C NMR, 1H NMR, NMR-2D, acid hydrolysis, Smith degradation
  
   
  
  Trichophyton mentagrophytes IFO 5466, Trichophyton rubrum IFO 5467
  CSDB ID 40025 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1456 [M*Na]+
Contained glycoepitopes: IEDB_130701,IEDB_136095,IEDB_137472,IEDB_1394182,IEDB_144983,IEDB_152206,IEDB_164174,IEDB_190606,IEDB_983930,SB_197,SB_44,SB_67,SB_72

• Article ID: 6873
  Levery SB, Toledo MS, Straus AH, Takahashi HK "Structure elucidation of sphingolipids from the mycopathogen Paracoccidioides brasiliensis: An immunodominant beta-galactofuranose residue is carried by a novel glycosylinositol phosphorylceramide antigen" - Biochemistry 37 (1998) 8764-8775
  

  Two major acidic glycolipid components (Pb-1 and Pb-2) have been extracted from the mycopathogen Paracoccidioides brasiliensis, a thermally dimorphic fungus endemic to rural areas of South and Central America. Sera of all patients exhibiting paracoccidioidomycosis were found to be reactive with Pb-1, but not with Pb-2; no reactivity was observed with sera of healthy patients or those with histoplasmosis [Toledo, M. S., Suzuki, S., Straus, A. H., and Takahashi, H. K. (1995) J. Mcd. Vet. Mycol. 33, 247-251]. We report here the complete structure elucidation of both P. brasiliensis glycolipids using monosaccharide, fatty acid, sphingosine, and inositol component analysis by GC-MS; H-1- and P-31 NMR spectroscopy; ESI-MS and -MS/CID-MS, linkage analysis, and exoglycosidase digestion. The compounds were found to be glycosylinositol phosphorylceramides (GIPCs) with the following structures: Pb-2, Manp-α1→3Manp-α1→2Ins1-P-1Cer; and Pb-1, Manp-α1→3[Galf-βl→6]Manp-α1→2lns1-P-1Cer. The serologically nonreactive Pb-2 appears to be a biosynthetic intermediate between mannosylinositol phosphorylceramide (MIPC), which is widely distributed among fungi, and the antigenic Pb-1. Pb-1 is a novel glycosphingolipid, similar to a triglycosyl IPC (Hc-VI) reported from Histoplasma capsulatum [Barr, K., Laine, R.A, and Lester, R. L. (1984) Biochemistry 23, 5589-5596], but differing in the anomeric configuration of the terminal Galf1→6 residue, which is immunodominant. The significance of these structures as serological and taxonomic markers, as well as their potential utility as targets for immunodiagnostic agents, is discussed.

  Publication DOI: 10.1021/bi9730083
  Journal NLM ID: 0370623
  Publisher: American Chemical Society
  Institutions: University of Georgia/Complex Carbohydrate Research Center, 220 Riverbend Road, Athens, GA, USA, Department of Biochemistry, Universidade Federal de Sao Paulo/Escola Paulista Medicina, Rua Botucatu 862, 04023-900, Sao Paulo, SP, Brazil
  Methods: 1H NMR, GC-MS, 31P NMR, ESI-MS, methanolysis, HPLC, enzymatic digestion, permethylation, acetylation, HPTLC, ESI-CID-MS, TOCSY, reduction, hydrolysis, COSY, NOESY, ion exchange chropmatography, ammonolysis, RECSY
  
   
  
  Paracoccidioides brasiliensis
  CSDB ID 40576 (all data & tools)