Show legend Show as text

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

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

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

  glucosylceramide, monoclonal antibody to GlcCe, Colletotrichum gloeosporioides

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

Show legend Show as text

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

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

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

  glucosylceramide, monoclonal antibody to GlcCe, Colletotrichum gloeosporioides

  Publication DOI: 10.1016/S0014-5793(04)00156-5
  Journal NLM ID: 0155157
  Publisher: Elsevier
  Correspondence: eliana.bergter@micro.ufrj.br
  Institutions: Instituto de Microbiologia Professor Paulo de Góes, Universidade Federal do Rio de Janeiro, Centro de Ciências da Saúde, Bloco I, Cidade Universitária, Rio de Janeiro 21941-590, Brazil, Departamento de Fisiologia, Instituto de Ciências Básicas da Saúde, Universidade Federal do Rio Grande do Sul, Porto Alegre, Brazil, Departamento de Parasitologia, Universidade de São Paulo, São Paulo, Brazil
  Methods: 1H NMR, GC-MS, sugar analysis, TLC, ELISA, ESI-MS, acid hydrolysis, ESI-MS/MS, biological assays, serological methods, extraction, HPTLC, immunofluorescence analyses
  
   
  
  Colletotrichum gloeosporioides
  CSDB ID 41323 (all data & tools)

Show legend Show as text

Structure type: monomer ; 734.5 [M+Na]+
Trivial name: neogala sphingolipid, NGL1
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_5

• Article ID: 7054
  Tani Y, Funatsu T, Ashida H, Ito M, Itonori S, Sugita M, Yamamoto K "Novel neogala-series glycosphingolipids with terminal mannose and glucose residues from Hirsutella rhossiliensis, an aureobasidin A-resistant ascomycete fungus" - Glycobiology 20(4) (2010) 433-441
  

  Hirsutella rhossiliensis, a nematophagous fungus belonging to the Ascomycota, is resistant to aureobasidin A (AbA). In this fungus, the biosynthetic pathway leading to mannosylinositolphosphoceramides, which is inhibited by AbA, was not detected. Instead, this fungus contains neutral complex glycosphingolipids (GSLs) and monoglycosylceramides. Except for monoglycosylceramides, neutral GSLs share a neogala-series core structure, Galβ1-6Galβ1-Cer. Among the GSLs of H. rhossiliensis, three novel GSLs with terminal Man and Glc residues on the sugar chain were elucidated. We analyzed GSL structure using compositional sugar, fatty acid, and sphingoid analyses, methylation analysis, matrix-assisted laser desorption ionization time-of-flight/mass spectrometry (MALDI-TOF MS), and (1)H nuclear magnetic resonance spectroscopy (NMR). The following structures were determined: Manα1-3Galβ1-6Galβ1-6Galβ1-Cer; Glcα1-2Galβ1-6Galβ1-6Galβ1-Cer; and Manα1-3Galβ1-6(Glcα1-4)Galβ1-6Galβ1-Cer. In the ceramides, the fatty acids were predominantly saturated h24:0-acids and the sphingoids were predominately t18:0- or t18:1-sphingoids. In contrast, the ceramides of Glcβ1-Cer contained d18:2- and d19:2-sphingoids. These findings indicate the presence of a novel biosynthetic pathway of neogala-series GSLs in fungi.

  glycosphingolipid, Aureobasidin A, Ascomycota, Hirsutella rhossiliensis, neogalatriaosylceramide

  NCBI PubMed ID: 20007186
  Publication DOI: 10.1093/glycob/cwp190
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Correspondence: yasu-t@lif.kyoto-u.ac.jp
  Institutions: Graduate School of Biostudies, Kyoto University, Kyoto, Japan, Department of Bioscience and Bioinformatics, Ritsumeikan University, Kusatsu, Shiga 525-8577, and Faculty of Liberal Arts and Education, Shiga University, Otsu, Japan
  Methods: 1H NMR, GC-MS, sugar analysis, TLC, GC, MALDI-TOF MS, enzymatic digestion, mild alkaline hydrolysis, methylation analysis
  
   
  
  Hirsutella rhossiliensis JCM 23109
  CSDB ID 41719 (all data & tools)

Show legend Show as text

Structure type: monomer ; 748.5 [M+Na]+
Trivial name: neogala sphingolipid, NGL1
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_5

• Article ID: 7054
  Tani Y, Funatsu T, Ashida H, Ito M, Itonori S, Sugita M, Yamamoto K "Novel neogala-series glycosphingolipids with terminal mannose and glucose residues from Hirsutella rhossiliensis, an aureobasidin A-resistant ascomycete fungus" - Glycobiology 20(4) (2010) 433-441
  

  Hirsutella rhossiliensis, a nematophagous fungus belonging to the Ascomycota, is resistant to aureobasidin A (AbA). In this fungus, the biosynthetic pathway leading to mannosylinositolphosphoceramides, which is inhibited by AbA, was not detected. Instead, this fungus contains neutral complex glycosphingolipids (GSLs) and monoglycosylceramides. Except for monoglycosylceramides, neutral GSLs share a neogala-series core structure, Galβ1-6Galβ1-Cer. Among the GSLs of H. rhossiliensis, three novel GSLs with terminal Man and Glc residues on the sugar chain were elucidated. We analyzed GSL structure using compositional sugar, fatty acid, and sphingoid analyses, methylation analysis, matrix-assisted laser desorption ionization time-of-flight/mass spectrometry (MALDI-TOF MS), and (1)H nuclear magnetic resonance spectroscopy (NMR). The following structures were determined: Manα1-3Galβ1-6Galβ1-6Galβ1-Cer; Glcα1-2Galβ1-6Galβ1-6Galβ1-Cer; and Manα1-3Galβ1-6(Glcα1-4)Galβ1-6Galβ1-Cer. In the ceramides, the fatty acids were predominantly saturated h24:0-acids and the sphingoids were predominately t18:0- or t18:1-sphingoids. In contrast, the ceramides of Glcβ1-Cer contained d18:2- and d19:2-sphingoids. These findings indicate the presence of a novel biosynthetic pathway of neogala-series GSLs in fungi.

  glycosphingolipid, Aureobasidin A, Ascomycota, Hirsutella rhossiliensis, neogalatriaosylceramide

  NCBI PubMed ID: 20007186
  Publication DOI: 10.1093/glycob/cwp190
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  Correspondence: yasu-t@lif.kyoto-u.ac.jp
  Institutions: Graduate School of Biostudies, Kyoto University, Kyoto, Japan, Department of Bioscience and Bioinformatics, Ritsumeikan University, Kusatsu, Shiga 525-8577, and Faculty of Liberal Arts and Education, Shiga University, Otsu, Japan
  Methods: 1H NMR, GC-MS, sugar analysis, TLC, GC, MALDI-TOF MS, enzymatic digestion, mild alkaline hydrolysis, methylation analysis
  
   
  
  Hirsutella rhossiliensis JCM 23109
  CSDB ID 42149 (all data & tools)

Show legend Show as text

Structure type: monomer ; 754.5843 [M+H]+
C₄₃H₇₉NO₉
Trivial name: Asperamide B
Compound class: glycosphingolipid
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_5

• Article ID: 7127
  Zhang Y, Wang S, Li XM, Cui CM, Feng C, Wang BG "New sphingolipids with a previously unreported 9-methyl-C20-sphingosine moiety from a Marine Algous endophytic fungus Aspergillus niger EN-13" - Lipids 42(8) (2007) 759-764
  

  Asperamides A (1) and B (2), a sphingolipid and their corresponding glycosphingolipid possessing a hitherto unreported 9-methyl-C20-sphingosine moiety, were characterized from the culture extract of Aspergillus niger EN-13, an endophytic fungus isolated from marine brown alga Colpomenia sinuosa. The structures were elucidated by spectroscopic and chemical methods as (2S,2'R,3R,3'E,4E,8E)-N-(2'-hydroxy-3'-hexadecenoyl)-9-methyl-4,8-icosadien-1,3-diol (1) and 1-O-β-D-glucopyranosyl-(2S,2'R,3R,3'E,4E,8E)-N-(2'-hydroxy-3'-hexadecenoyl)-9-methyl-4,8-icosadien-1,3-diol (2). In the antifungal assay, asperamide A (1) displayed moderate activity against Candida albicans.

  glycosphingolipid, sphingolipid, endophytic fungus, Marine alga, Colpomenia sinuosa, Aspergillus niger, Asperamide A, Asperamide B

  NCBI PubMed ID: 17605063
  Publication DOI: 10.1007/s11745-007-3079-8
  Journal NLM ID: 0060450
  Publisher: American Oil Chemists' Society
  Correspondence: wangbg@ms.qdio.ac.cn
  Institutions: Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Qingdao, China, Graduate School of the Chinese Academy of Sciences, Beijing, China
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, GC-MS, TLC, ESI-MS, composition analysis, methanolysis, HPLC, extraction, CC, HR-ESI-MS, antifungal assay
  
   
  
  Aspergillus niger EN-13
  CSDB ID 41799 (all data & tools)

Show legend Show as text

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

• Article ID: 7465
  Rodrigues ML, Nimrichter L, Oliveira DL, Frases S, Miranda K, Zaragoza O, Alvarez M, Nakouzi A, Feldmesser M, Casadevall A "Vesicular polysaccharide export in Cryptococcus neoformans is a eukaryotic solution to the problem of fungal trans-cell wall transport" - Eukaryotic Cell 6(1) (2007) 48-59
  

  The mechanisms by which macromolecules are transported through the cell wall of fungi are not known. A central question in the biology of Cryptococcus neoformans, the causative agent of cryptococcosis, is the mechanism by which capsular polysaccharide synthesized inside the cell is exported to the extracellular environment for capsule assembly and release. We demonstrate that C. neoformans produces extracellular vesicles during in vitro growth and animal infection. Vesicular compartments, which are transferred to the extracellular space by cell wall passage, contain glucuronoxylomannan (GXM), a component of the cryptococcal capsule, and key lipids, such as glucosylceramide and sterols. A correlation between GXM-containing vesicles and capsule expression was observed. The results imply a novel mechanism for the release of the major virulence factor of C. neoformans whereby polysaccharide packaged in lipid vesicles crosses the cell wall and the capsule network to reach the extracellular environment.

  capsular polysaccharides, lipid, Cryptococcus neoformans, cryptococcosis, vesicles

  NCBI PubMed ID: 17114598
  Publication DOI: 10.1128/EC.00318-06
  Journal NLM ID: 101130731
  Publisher: American Society for Microbiology
  Correspondence: Arturo Casadevall
  Institutions: Servicio de Micología, Centro Nacional de Microbiología, Instituto de Salud Carlos III, Madrid, Spain, Laboratório de Estudos Integrados em Bioquímica Microbiana, Instituto de Microbiologia Professor Paulo de Góes, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil, Department of Microbiology and Immunology, Albert Einstein College of Medicine, New York, NY, USA, Division of Infectious Diseases, Department of Medicine, Albert Einstein College of Medicine, New York, NY, USA, Laboratório de Ultraestrutura Celular Hertha Meyer, Instituto de Biofísica Carlos Chagas Filho, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil
  Methods: ELISA, ESI-MS, biological assays, serological methods, affinity chromatography, HPTLC, CC, transmission electron microscopy, cell growth, cell viability assay, centrifugation
  
   
  
  Cryptococcus neoformans D ATCC 24067, Cryptococcus neoformans A H99, Cryptococcus neoformans A HEC3393, Cryptococcus neoformans (ΔCap67 mutant)
  CSDB ID 44023 (all data & tools)

Show legend Show as text

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

• Article ID: 7537
  Ishibashi Y, Ikeda K, Sakaguchi K, Okino N, Taguchi R, Ito M "Quality control of fungus-specific glucosylceramide in Cryptococcus neoformans by endoglycoceramidase-related protein 1 (EGCrP1)" - Journal of Biological Chemistry 287(1) (2012) 368-381
  

  A fungus-specific glucosylceramide (GlcCer), which contains a unique sphingoid base possessing two double bonds and a methyl substitution, is essential for pathogenicity in fungi. Although the biosynthetic pathway of the GlcCer has been well elucidated, little is known about GlcCer catabolism because a GlcCer-degrading enzyme (glucocerebrosidase) has yet to be identified in fungi. We found a homologue of endoglycoceramidase tentatively designated endoglycoceramidase-related protein 1 (EGCrP1) in several fungal genomic databases. The recombinant EGCrP1 hydrolyzed GlcCer but not other glycosphingolipids, whereas endoglycoceramidase hydrolyzed oligosaccharide- linked glycosphingolipids but not GlcCer. Disruption of egcrp1 in Cryptococcus neoformans, a typical pathogenic fungus causing cryptococcosis, resulted in the accumulation of fungus-specific GlcCer and immature GlcCer that possess sphingoid bases without a methyl substitution concomitant with a dysfunction of polysaccharide capsule formation. These results indicated that EGCrP1 participates in the catabolism of GlcCer and especially functions to eliminate immature GlcCer in vivo that are generated as by-products due to the broad specificity of GlcCer synthase. We conclude that EGCrP1, a glucocerebrosidase identified for the first time in fungi, controls the quality of GlcCer by eliminating immature GlcCer incorrectly generated in C. neoformans, leading to accurate processing of fungus-specific GlcCer.

  glycosphingolipid, Cryptococcus neoformans, glucosylceramide, EGCase II

  NCBI PubMed ID: 22072709
  Publication DOI: 10.1074/jbc.M111.311340
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Correspondence: Ito M
  Institutions: Department of Bioscience and Biotechnology, Graduate School of Bioresource and Bioenvironmental Sciences, Kyushu University, Fukuoka, Japan, Department of Metabolome, Graduate School of Medicine, University of Tokyo, Tokyo, Japan, Institute for Advanced Biosciences, Keio University, Yamagata, Japan, Department of Biomedical Sciences, College of Life and Health Sciences, Chubu University, Aichi, Japan, New Energy and Industrial Technology Development Organization (NEDO), MUZA, Kanagawa, Japan, Laboratory for Molecular Membrane Neuroscience, RIKEN Brain Science Institute, Wako, Japan
  Methods: DNA sequencing, SDS-PAGE, DNA techniques, TLC, GLC, ESI-MS/MS, MALDI-TOF MS, HPLC, extraction, CC, protein detection, enzymatic assay, derivatization
  
   
  
  Cryptococcus neoformans var. grubii H99 ATCC 208821, Rhizopus oryzae NBRC 9364, Aspergillus fumigatus NBRC 33022
  CSDB ID 44254 (all data & tools)

Show legend Show as text

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

• Article ID: 7833
  Singh A, Wang H, Silva LC, Na C, Prieto M, Futerman AH, Luberto C, Del Poeta M "Methylation of glycosylated sphingolipid modulates membrane lipid topography and pathogenicity of Cryptococcus neoformans" - Cellular Microbiology 14(4) (2012) 500-516
  

  In previous studies we showed that the replication of Cryptococcus neoformans in the lung environment is controlled by the glucosylceramide (GlcCer) synthase gene (GCS1), which synthesizes the membrane sphingolipid GlcCer from the C9-methyl ceramide. Here, we studied the effect of the mutation of the sphingolipid C9 methyltransferase gene (SMT1), which adds a methyl group to position 9 of the sphingosine backbone of ceramide. The C. neoformans Δsmt1 mutant does not make C9-methyl ceramide and, thus, any methylated GlcCer. However, it accumulates demethylated ceramide and demethylated GlcCer. The Δsmt1 mutant loses more than 80% of its virulence compared with the wild type and the reconstituted strain. Interestingly, growth of C. neoformans Δsmt1 in the lung was decreased and C. neoformans cells were contained in lung granulomas, which significantly reduced the rate of their dissemination to the brain reducing the onset of meningoencephalitis. Thus, using fluorescent spectroscopy and atomic force microscopy we compared the wild type and Δsmt1 mutant and found that the altered membrane composition and GlcCer structure affects fungal membrane rigidity, suggesting that specific sphingolipid structures are required for proper fungal membrane organization and integrity. Therefore, we propose that the physical structure of the plasma membrane imparted by specific classes of sphingolipids represents a critical factor for the ability of the fungus to establish virulence.

  virulence, methylation, glycosphingolipid, Cryptococcus neoformans

  NCBI PubMed ID: 22151739
  Publication DOI: 10.1111/j.1462-5822.2011.01735.x
  Journal NLM ID: 100883691
  Publisher: Oxford: Wiley-Blackwell
  Correspondence: delpoeta@musc.edu
  Institutions: Division of Infectious Diseases, Medical University of South Carolina, Charleston, USA, Biochemistry & Molecular Biology, Medical University of South Carolina, Charleston, USA, Microbiology & Immunology, Medical University of South Carolina, Charleston, USA, Craniofacial Biology, Medical University of South Carolina, Charleston, USA, Department of Civil Engineering & Geological Sciences, University of Notre Dame, Notre Dame, USA, iMed. UL, Faculdade de Farmácia, da Universidade de Lisboa, Lisbon, Portugal, Centro de Química-Física Molecular, IST, Lisbon, Portugal, Department of Biological Chemistry, Weizmann Institute of Science, Rehovot, Israel, Laboratory of Clinical Infectious Diseases, Molecular Microbiology Section, National Institute of Allergy and Infectious Diseases, Bethesda, USA
  Methods: DNA techniques, MS/MS, biological assays, MS, enzymatic digestion, extraction, atomic force microscopy, fluorescence spectroscopy, cell growth
  
   
  
  Cryptococcus neoformans var. grubii A H99, Cryptococcus neoformans var. grubii A H99 (Δsmt1H99 mutant), Cryptococcus neoformans var. grubii A H99 (Δsmt1ΔSMT1 mutant), Cryptococcus neoformans var. grubii A H99 (Δgcs1 mutant), Cryptococcus neoformans var. grubii A H99 (Δgcs1ΔGCS1 mutant)
  CSDB ID 45816 (all data & tools)

Show legend Show as text

Structure type: monomer
Trivial name: phalluside-1
Compound class: cerebroside
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_5

• Article ID: 7869
  Yang SX, Wang HP, Gao JM, Zhang Q, Laatsch H, Kuang Y "Fusaroside, a unique glycolipid from Fusarium sp., an endophytic fungus isolated from Melia azedarach" - Organic and Biomolecular Chemistry 10(4) (2012) 819-824
  

  Fusaroside (1), a unique trehalose-containing glycolipid composed of the 4-hydroxyl group of a trehalose unit attached to the carboxylic carbon of a long-chain fatty acid, was isolated from the organic extract of fermentation broths of an endophytic fungus, Fusarium sp. LN-11 isolated from the leaves of Melia azedarach. Six known compounds, phalluside (2), (9R*,10R*,7E)-6, 9,10-trihydroxyoctadec-7-enoic acid (3), porrigenic acid (4), (9Z)-2,3-dihydroxypropyl octadeca-9-enoate (5), cerevisterol (6) and ergokonin B (7), were also isolated from this fungus. The glycolipid contains a rare branched long-chain fatty acid (C(20:4)) with a conjugated diene moiety and a conjugated ketone moiety. The structure of the new compound 1 was elucidated by spectroscopic methods (1D and 2D NMR experiments, MS) and chemical degradations. The metabolites 1-5 were shown to have moderate to weak active against the brine shrimp larvae. To our knowledge, this is the first report of isolation of the first representative of a new family of glycolipids from natural sources.

  glycolipid, fusaroside, Fusarium sp., Melia azedarach

  NCBI PubMed ID: 22124543
  Publication DOI: 10.1039/c1ob06426f
  Journal NLM ID: 101154995
  Publisher: The Royal Society of Chemistry
  Correspondence: Gao JM ; Laatsch H
  Institutions: Department of Organic Chemistry, University of Göttingen, Göttingen, Germany, Chemical Biological Research Institute, College of Science, Northwest A&F University, Yangling, China, Department of Chemical Engineering, Huainan Union University, Huainan, China, Department of Crop Sciences, Georg-August-Universität Göttingen, Göttingen, Germany
  Methods: 13C NMR, 1H NMR, EI-MS, NMR-2D, IR, GC-MS, TLC, ESI-MS, biological assays, UV, extraction, optical rotation measurement, CC, reversed-phase chromatography, cell growth, HR-ESI-MS, derivatization
  
   
  
  Fusarium sp. LN-11
  CSDB ID 45943 (all data & tools)

Show legend Show as text

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

• Article ID: 8239
  Tani Y, Amaishi Y, Funatsu T, Ito M, Itonori S, Hata Y, Ashida H, Yamamoto K "Structural analysis of cerebrosides from Aspergillus fungi: the existence of galactosylceramide in A. oryzae" - Biotechnology Letters 36(12) (2014) 2507-2513
  

  Glucosylceramide and galactosylceramide were detected in three Aspergillus species: Aspergillus oryzae, Aspergillus sojae and Aspergillus. awamori, using borate-coated TLC. The cerebrosides from A. oryzae were further purified by ion exchange and iatrobeads column chromatographies with or without borate, and determined the composition of sugar, fatty acid and sphingoid base by GC/MS, MALDI-TOF/MS and 1H-NMR. We identified them as β-glucosylceramide and β-galactosylceramide. The ceramide moiety of both cerebrosides consisted mainly of 2-hydroxystearic acid and either 9-methyl-octadeca-4, 8-sphingadienine or octadeca-4, 8-sphingadienine. To our knowledge, this is the first study to provide evidence for the presence of β-galactosylceramide in A. oryzae.

  glycosphingolipid, galactosylceramide, cerebroside, Aspergillus oryzae, filamentous fungus

  NCBI PubMed ID: 25129050
  Publication DOI: 10.1007/s10529-014-1631-1
  Journal NLM ID: 8008051
  Publisher: Kluwer Academic Publishers
  Correspondence: Ashida H
  Institutions: Graduate School of Biostudies, Kyoto University, Kyoto, Japan, Department of Bioscience and Bioinformatics, Ritsumeikan University, Kusatsu, Japan, Faculty of Liberal Arts and Education, Shiga University, Otsu, Japan, Gekkeikan Sake Co. Ltd, Research Institute, Kyoto, Japan, Faculty of Biology-Oriented Science and Technology, Kinki University, Kinokawa, Japan, Research Institute for Bioresources and Biotechnology, Ishikawa Prefectural University, Nonoichi, Japan
  Methods: 1H NMR, GC-MS, TLC, acid hydrolysis, GC, MALDI-TOF MS, methanolysis, ion-exchange chromatography, extraction, methylation analysis
  
   
  
  Aspergillus oryzae OSI1013
  CSDB ID 46557 (all data & tools)

Show legend Show as text

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

• Article ID: 8239
  Tani Y, Amaishi Y, Funatsu T, Ito M, Itonori S, Hata Y, Ashida H, Yamamoto K "Structural analysis of cerebrosides from Aspergillus fungi: the existence of galactosylceramide in A. oryzae" - Biotechnology Letters 36(12) (2014) 2507-2513
  

  Glucosylceramide and galactosylceramide were detected in three Aspergillus species: Aspergillus oryzae, Aspergillus sojae and Aspergillus. awamori, using borate-coated TLC. The cerebrosides from A. oryzae were further purified by ion exchange and iatrobeads column chromatographies with or without borate, and determined the composition of sugar, fatty acid and sphingoid base by GC/MS, MALDI-TOF/MS and 1H-NMR. We identified them as β-glucosylceramide and β-galactosylceramide. The ceramide moiety of both cerebrosides consisted mainly of 2-hydroxystearic acid and either 9-methyl-octadeca-4, 8-sphingadienine or octadeca-4, 8-sphingadienine. To our knowledge, this is the first study to provide evidence for the presence of β-galactosylceramide in A. oryzae.

  glycosphingolipid, galactosylceramide, cerebroside, Aspergillus oryzae, filamentous fungus

  NCBI PubMed ID: 25129050
  Publication DOI: 10.1007/s10529-014-1631-1
  Journal NLM ID: 8008051
  Publisher: Kluwer Academic Publishers
  Correspondence: Ashida H
  Institutions: Graduate School of Biostudies, Kyoto University, Kyoto, Japan, Department of Bioscience and Bioinformatics, Ritsumeikan University, Kusatsu, Japan, Faculty of Liberal Arts and Education, Shiga University, Otsu, Japan, Gekkeikan Sake Co. Ltd, Research Institute, Kyoto, Japan, Faculty of Biology-Oriented Science and Technology, Kinki University, Kinokawa, Japan, Research Institute for Bioresources and Biotechnology, Ishikawa Prefectural University, Nonoichi, Japan
  Methods: 1H NMR, GC-MS, TLC, acid hydrolysis, GC, MALDI-TOF MS, methanolysis, ion-exchange chromatography, extraction, methylation analysis
  
   
  
  Aspergillus oryzae OSI1013
  CSDB ID 46558 (all data & tools)

Show legend Show as text

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

• Article ID: 8239
  Tani Y, Amaishi Y, Funatsu T, Ito M, Itonori S, Hata Y, Ashida H, Yamamoto K "Structural analysis of cerebrosides from Aspergillus fungi: the existence of galactosylceramide in A. oryzae" - Biotechnology Letters 36(12) (2014) 2507-2513
  

  Glucosylceramide and galactosylceramide were detected in three Aspergillus species: Aspergillus oryzae, Aspergillus sojae and Aspergillus. awamori, using borate-coated TLC. The cerebrosides from A. oryzae were further purified by ion exchange and iatrobeads column chromatographies with or without borate, and determined the composition of sugar, fatty acid and sphingoid base by GC/MS, MALDI-TOF/MS and 1H-NMR. We identified them as β-glucosylceramide and β-galactosylceramide. The ceramide moiety of both cerebrosides consisted mainly of 2-hydroxystearic acid and either 9-methyl-octadeca-4, 8-sphingadienine or octadeca-4, 8-sphingadienine. To our knowledge, this is the first study to provide evidence for the presence of β-galactosylceramide in A. oryzae.

  glycosphingolipid, galactosylceramide, cerebroside, Aspergillus oryzae, filamentous fungus

  NCBI PubMed ID: 25129050
  Publication DOI: 10.1007/s10529-014-1631-1
  Journal NLM ID: 8008051
  Publisher: Kluwer Academic Publishers
  Correspondence: Ashida H
  Institutions: Graduate School of Biostudies, Kyoto University, Kyoto, Japan, Department of Bioscience and Bioinformatics, Ritsumeikan University, Kusatsu, Japan, Faculty of Liberal Arts and Education, Shiga University, Otsu, Japan, Gekkeikan Sake Co. Ltd, Research Institute, Kyoto, Japan, Faculty of Biology-Oriented Science and Technology, Kinki University, Kinokawa, Japan, Research Institute for Bioresources and Biotechnology, Ishikawa Prefectural University, Nonoichi, Japan
  Methods: 1H NMR, GC-MS, TLC, acid hydrolysis, GC, MALDI-TOF MS, methanolysis, ion-exchange chromatography, extraction, methylation analysis
  
   
  
  Aspergillus oryzae OSI1013
  CSDB ID 46559 (all data & tools)

Show legend Show as text

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

• Article ID: 8239
  Tani Y, Amaishi Y, Funatsu T, Ito M, Itonori S, Hata Y, Ashida H, Yamamoto K "Structural analysis of cerebrosides from Aspergillus fungi: the existence of galactosylceramide in A. oryzae" - Biotechnology Letters 36(12) (2014) 2507-2513
  

  Glucosylceramide and galactosylceramide were detected in three Aspergillus species: Aspergillus oryzae, Aspergillus sojae and Aspergillus. awamori, using borate-coated TLC. The cerebrosides from A. oryzae were further purified by ion exchange and iatrobeads column chromatographies with or without borate, and determined the composition of sugar, fatty acid and sphingoid base by GC/MS, MALDI-TOF/MS and 1H-NMR. We identified them as β-glucosylceramide and β-galactosylceramide. The ceramide moiety of both cerebrosides consisted mainly of 2-hydroxystearic acid and either 9-methyl-octadeca-4, 8-sphingadienine or octadeca-4, 8-sphingadienine. To our knowledge, this is the first study to provide evidence for the presence of β-galactosylceramide in A. oryzae.

  glycosphingolipid, galactosylceramide, cerebroside, Aspergillus oryzae, filamentous fungus

  NCBI PubMed ID: 25129050
  Publication DOI: 10.1007/s10529-014-1631-1
  Journal NLM ID: 8008051
  Publisher: Kluwer Academic Publishers
  Correspondence: Ashida H
  Institutions: Graduate School of Biostudies, Kyoto University, Kyoto, Japan, Department of Bioscience and Bioinformatics, Ritsumeikan University, Kusatsu, Japan, Faculty of Liberal Arts and Education, Shiga University, Otsu, Japan, Gekkeikan Sake Co. Ltd, Research Institute, Kyoto, Japan, Faculty of Biology-Oriented Science and Technology, Kinki University, Kinokawa, Japan, Research Institute for Bioresources and Biotechnology, Ishikawa Prefectural University, Nonoichi, Japan
  Methods: 1H NMR, GC-MS, TLC, acid hydrolysis, GC, MALDI-TOF MS, methanolysis, ion-exchange chromatography, extraction, methylation analysis
  
   
  
  Aspergillus oryzae OSI1013
  CSDB ID 46560 (all data & tools)

Show legend Show as text

Structure type: monomer ; 1187 [M]+
Compound class: ceramide
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_5

• Article ID: 8254
  Fujino Y, Ohnishi M "Structure of cerebroside in Aspergillus oryzae" - Biochimica et Biophysica Acta 486(1) (1977) 161-171
  

  Structural studies on cerebroside isolated from Aspergillus oryzae were carried out using mainly gas-liquid chromatography-mass spectrometry. The major component fatty acids were 2-hydroxystearic and 2-hydroxy-trans-octadecenoic acid; branched 17?-methyl nonadecasphingadienine isomers were the predominant long-chain bases. The component sugar was only glucose. The structure of the major cerebrosides was assumed to be N-2'-hydroxystearoyl-1-O-glucosyl-17?-methyl sphingadienine and N-2'-hydroxyoctadecenoyl-1-O-glucosyl-17?-methyl sphingadienine.

  cerebroside

  NCBI PubMed ID: 1009131
  Publication DOI: 10.1016/0005-2760(77)90080-7
  Journal NLM ID: 0217513
  Publisher: Elsevier
  Institutions: Department of Agricultural Chemistry, Obihiro University, Obihiro, Japan
  Methods: 1H NMR, GLC-MS, IR, TLC, acid hydrolysis, GLC, methanolysis, extraction, CC, alcaline hydrolysis
  
   
  
  Aspergillus oryzae IFO 4290
  CSDB ID 46591 (all data & tools)

Show legend Show as text

Structure type: monomer ; 1185 [M]+
Compound class: ceramide
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_5

• Article ID: 8254
  Fujino Y, Ohnishi M "Structure of cerebroside in Aspergillus oryzae" - Biochimica et Biophysica Acta 486(1) (1977) 161-171
  

  Structural studies on cerebroside isolated from Aspergillus oryzae were carried out using mainly gas-liquid chromatography-mass spectrometry. The major component fatty acids were 2-hydroxystearic and 2-hydroxy-trans-octadecenoic acid; branched 17?-methyl nonadecasphingadienine isomers were the predominant long-chain bases. The component sugar was only glucose. The structure of the major cerebrosides was assumed to be N-2'-hydroxystearoyl-1-O-glucosyl-17?-methyl sphingadienine and N-2'-hydroxyoctadecenoyl-1-O-glucosyl-17?-methyl sphingadienine.

  cerebroside

  NCBI PubMed ID: 1009131
  Publication DOI: 10.1016/0005-2760(77)90080-7
  Journal NLM ID: 0217513
  Publisher: Elsevier
  Institutions: Department of Agricultural Chemistry, Obihiro University, Obihiro, Japan
  Methods: 1H NMR, GLC-MS, IR, TLC, acid hydrolysis, GLC, methanolysis, extraction, CC, alcaline hydrolysis
  
   
  
  Aspergillus oryzae IFO 4290
  CSDB ID 46592 (all data & tools)