Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Host organism: Homo sapiens
Organ / tissue: cell cultureAssociated disease: infection due to Aspergillus fumigatus [ICD11:
XN5Z7 
]
The structure was elucidated in this paperNCBI PubMed ID: 8013053Publication DOI: 10.1016/0009-3084(94)90043-4Journal NLM ID: 0067206Institutions: Institut für Physiologische Chemie der Universität Bonn, Bonn, Germany, Departmento de Microbiologia Geral, Instituto de Microbiologia da Universidade Federal de Rio de Janeiro, Rio de Janeiro, Brasil
Ceramide monohexosides from Aspergillus fumigatus 2140 and 2109 strains and Aspergillus versicolor 550 strain, obtained by silica gel 60, and Iatrobeads chromatography were analysed using high-resolution 1D-, 2D-1H-NMR and 13C-NMR spectroscopy and fast atom bombardment mass spectrometry (FAB-MS). The ceramide monohexoside fraction (CMH) from A. fumigatus 2140 and A. versicolor 550 was identified as glucosylceramide, whereas glucose and galactose were present at a ratio of 1:1 in the CMH of A. fumigatus 2109. The major glycosphingolipid has a particular ceramide composition consisting of 9-methyl-4,8-sphingadienine linked to a 2-hydroxyoctadec-3-enoic acid. Although the structures presently described are similar to those of monohexosylceramides from other fungi, including edible ones, this is the first report on their occurrence in species pathogenic in humans.
FAB-MS, 13C-NMR spectroscopy, galactosylceramide, Aspergillus fumigatus, glucosylceramide, Aspergillus versicolor, 1H-NMR spectroscopy
Structure type: monomer
Location inside paper: p.17, fig.7, CMH, fig.4, fig.5, fig.6, table 1
Trivial name: glucosylceramide
Compound class: glycosphingolipid, cerebroside
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_5,SB_61
Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, FAB-MS, NMR-1D, methanolysis, HPLC, extraction, HPTLC, CC
Comments, role: acylated form
Related record ID(s): 40549, 40812, 40813, 40814, 42250, 42251, 42252, 42253, 42254, 42255, 42256, 42257, 42258, 42259, 42260, 42261, 42262, 42263, 42264, 42265, 42266, 42267, 42268, 42269, 42270, 42271, 42272, 42273, 42274, 42275, 42276, 42280, 42281, 42282, 42287, 42288, 43402, 43403, 43418, 43419, 43420, 43679, 43680
NCBI Taxonomy refs (TaxIDs): 746128,
46472
Show glycosyltransferases
NMR conditions: in CDCl3 at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19
1,2 Ac
1,3 Ac
1,4 Ac
1,6 Ac
1 bDGlcp 100.60 71.21 72.70 68.23 71.95 61.85
2,2 Ac
2 l?2HOC18={t3} 168.48 74.46 123.00 138.12 32.41-32.64 28.0-30.5 28.0-30.5 28.0-30.5 28.0-30.5 28.0-30.5 28.0-30.5 28.0-30.5 28.0-30.5 28.0-30.5 28.0-30.5 28.0-30.5 28.0-30.5 14.21
3 Ac
xXSR9b1SphdC19 67.15 50.83 73.25 124.51 136.90 32.41-32.64 27.47 123.00 136.31 39.79 28.1 28.0-30.5 28.0-30.5 28.0-30.5 28.0-30.5 28.0-30.5 28.0-30.5 14.21 16.06
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17 H18 H19
1,2 Ac
1,3 Ac
1,4 Ac
1,6 Ac
1 bDGlcp 4.47 4.95 5.18 5.08 3.68 4.13-4.23
2,2 Ac
2 l?2HOC18={t3} - 5.50 5.50 5.87 2.05 1.35 1.2-1.4 1.2-1.4 1.2-1.4 1.2-1.4 1.2-1.4 1.2-1.4 1.2-1.4 1.2-1.4 1.2-1.4 1.2-1.4 1.2-1.4 0.87
3 Ac
xXSR9b1SphdC19 3.61-3.92 4.29 5.30 5.39 5.81 2.05 2.05 5.07 - 1.94 1.35 1.2-1.4 1.2-1.4 1.2-1.4 1.2-1.4 1.2-1.4 1.2-1.4 0.87 1.56
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9 C10/H10 C11/H11 C12/H12 C13/H13 C14/H14 C15/H15 C16/H16 C17/H17 C18/H18 C19/H19
1,2 Ac
1,3 Ac
1,4 Ac
1,6 Ac
1 bDGlcp 100.60/4.47 71.21/4.95 72.70/5.18 68.23/5.08 71.95/3.68 61.85/4.13-4.23
2,2 Ac
2 l?2HOC18={t3} 74.46/5.50 123.00/5.50 138.12/5.87 32.41-32.64/2.05 28.0-30.5/1.35 28.0-30.5/1.2-1.4 28.0-30.5/1.2-1.4 28.0-30.5/1.2-1.4 28.0-30.5/1.2-1.4 28.0-30.5/1.2-1.4 28.0-30.5/1.2-1.4 28.0-30.5/1.2-1.4 28.0-30.5/1.2-1.4 28.0-30.5/1.2-1.4 28.0-30.5/1.2-1.4 28.0-30.5/1.2-1.4 14.21/0.87
3 Ac
xXSR9b1SphdC19 67.15/3.61-3.92 50.83/4.29 73.25/5.30 124.51/5.39 136.90/5.81 32.41-32.64/2.05 27.47/2.05 123.00/5.07 39.79/1.94 28.1/1.35 28.0-30.5/1.2-1.4 28.0-30.5/1.2-1.4 28.0-30.5/1.2-1.4 28.0-30.5/1.2-1.4 28.0-30.5/1.2-1.4 28.0-30.5/1.2-1.4 14.21/0.87 16.06/1.56
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 | H17 | H18 | H19 |
|---|
| 1,2 | Ac | |
| 1,3 | Ac | |
| 1,4 | Ac | |
| 1,6 | Ac | |
| 1 | bDGlcp | 4.47 | 4.95 | 5.18 | 5.08 | 3.68 | 4.13
4.23 | |
| 2,2 | Ac | |
| 2 | l?2HOC18={t3} |
| 5.50 | 5.50 | 5.87 | 2.05 | 1.35 | 1.2
1.4 | 1.2
1.4 | 1.2
1.4 | 1.2
1.4 | 1.2
1.4 | 1.2
1.4 | 1.2
1.4 | 1.2
1.4 | 1.2
1.4 | 1.2
1.4 | 1.2
1.4 | 0.87 | |
| 3 | Ac | |
| | xXSR9b1SphdC19 | 3.61
3.92 | 4.29 | 5.30 | 5.39 | 5.81 | 2.05 | 2.05 | 5.07 |
| 1.94 | 1.35 | 1.2
1.4 | 1.2
1.4 | 1.2
1.4 | 1.2
1.4 | 1.2
1.4 | 1.2
1.4 | 0.87 | 1.56 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 | C17 | C18 | C19 |
|---|
| 1,2 | Ac | |
| 1,3 | Ac | |
| 1,4 | Ac | |
| 1,6 | Ac | |
| 1 | bDGlcp | 100.60 | 71.21 | 72.70 | 68.23 | 71.95 | 61.85 | |
| 2,2 | Ac | |
| 2 | l?2HOC18={t3} | 168.48 | 74.46 | 123.00 | 138.12 | 32.41
32.64 | 28.0
30.5 | 28.0
30.5 | 28.0
30.5 | 28.0
30.5 | 28.0
30.5 | 28.0
30.5 | 28.0
30.5 | 28.0
30.5 | 28.0
30.5 | 28.0
30.5 | 28.0
30.5 | 28.0
30.5 | 14.21 | |
| 3 | Ac | |
| | xXSR9b1SphdC19 | 67.15 | 50.83 | 73.25 | 124.51 | 136.90 | 32.41
32.64 | 27.47 | 123.00 | 136.31 | 39.79 | 28.1 | 28.0
30.5 | 28.0
30.5 | 28.0
30.5 | 28.0
30.5 | 28.0
30.5 | 28.0
30.5 | 14.21 | 16.06 |
|
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
