Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Organ / tissue: yeast,
mycelium
The structure was elucidated in this paperNCBI PubMed ID: 3555875Publication DOI: 10.1016/0009-3084(87)90012-0Journal NLM ID: 0067206Institutions: Department of Chemistry, Faculty of Science and Technology, Kinki University, Osaka, Japan, Department of Chemistry, Faculty of Science and Technology, Kinki University, Osaka, Japan, Department of Biochemistry, Gifu University School of Medicine, Gifu, Japan
Structural studies on the cerebroside isolated from the yeast form of a dimorphic pathogen, Candida albicans were carried out using fast atom bombardment mass spectrometry (FAB/MS), proton magnetic resonance spectrometry, gas chromatography-mass spectrometry and usual chemical methods. The component sugar was only glucose attached to ceramide in a beta-configuration. The major fatty acid was 2-hydroxystearic acid (62%). The predominant long chain base was identified as 9-methyl-C18-sphinga-4,8-dienine which is widely distributed in fungi and reported to be essential to the fruit-inducing activity of fungi. Therefore, the structure of the main molecular species of the cerebroside was determined to be N-2-hydroxystearoyl-1-O-beta-glucosyl-9-methyl-C18-sphinga-4,8-dienine. Cerebroside prepared from the mycelial form of C. albicans has the same structure.
glycolipid, Candida albicans, cerebroside, 9-methyl sphingadienine, branched long chain base, human pathogen
Structure type: monomer ; 754 [M-H]-
C
43H
80NO
9Location inside paper: p.8, p.10, fig.7, GL-1
Compound class: glycosphingolipid, cerebroside, ceramide
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_5
Methods: 1H NMR, methylation, IR, FAB-MS, GC-MS, TLC, acid hydrolysis, GLC, methanolysis, extraction, periodate oxidation, reduction, column chromatography, cell growth, derivatization, glycolipid detection, osmium tetroxide oxidation
Comments, role: no significant change occurs in glycolipid composition during the yeast-mycelial conversion of C. albicans
Related record ID(s): 40549, 40812, 40813, 40814, 42250, 42251, 42252, 42253, 42254, 42256, 42257, 42258, 42259, 42260, 42261, 42262, 42263, 42264, 42265, 42266, 42267, 42268, 42269, 42270, 42271, 42272, 42273, 42274, 42275, 42276, 42279, 42280, 42281, 42282, 42287, 42288, 43402, 43403, 43418, 43419, 43420, 43672, 43673, 43674, 43679, 43680, 43704
NCBI Taxonomy refs (TaxIDs): 5476
Show glycosyltransferases
NMR conditions: in vol 90%CHCl3 / vol 10%CH3COOH at 293(H) K
[as TSV]
1H NMR data: present in publication
|
There is only one chemically distinct structure:
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Organ / tissue: mycelium
The structure was elucidated in this paperNCBI PubMed ID: 3555875Publication DOI: 10.1016/0009-3084(87)90012-0Journal NLM ID: 0067206Institutions: Department of Chemistry, Faculty of Science and Technology, Kinki University, Osaka, Japan, Department of Chemistry, Faculty of Science and Technology, Kinki University, Osaka, Japan, Department of Biochemistry, Gifu University School of Medicine, Gifu, Japan
Structural studies on the cerebroside isolated from the yeast form of a dimorphic pathogen, Candida albicans were carried out using fast atom bombardment mass spectrometry (FAB/MS), proton magnetic resonance spectrometry, gas chromatography-mass spectrometry and usual chemical methods. The component sugar was only glucose attached to ceramide in a beta-configuration. The major fatty acid was 2-hydroxystearic acid (62%). The predominant long chain base was identified as 9-methyl-C18-sphinga-4,8-dienine which is widely distributed in fungi and reported to be essential to the fruit-inducing activity of fungi. Therefore, the structure of the main molecular species of the cerebroside was determined to be N-2-hydroxystearoyl-1-O-beta-glucosyl-9-methyl-C18-sphinga-4,8-dienine. Cerebroside prepared from the mycelial form of C. albicans has the same structure.
glycolipid, Candida albicans, cerebroside, 9-methyl sphingadienine, branched long chain base, human pathogen
Structure type: monomer ; 754 [M-H]-
Location inside paper: Fig.7, GL-1
Compound class: glycosphingolipid, cerebroside
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_5
Methods: 1H NMR, methylation, IR, FAB-MS, GC-MS, TLC, acid hydrolysis, GLC, methanolysis, extraction, periodate oxidation, reduction, column chromatography, cell growth, derivatization, glycolipid detection, osmium tetroxide oxidation
NCBI Taxonomy refs (TaxIDs): 5476
Show glycosyltransferases
NMR conditions: in 90%CDCl3 / 10%CD3OD at 298(H) K
[as TSV]
1H NMR data: present in publication
|
There is only one chemically distinct structure:
Found 
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