Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting body
The structure was elucidated in this paperPublication DOI: 10.1016/S0040-4020(00)00548-2Journal NLM ID: 2984170RPublisher: Pergamon Press
Correspondence: ojika
agr.nagoya-u.ac.jp
Institutions: Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa-ku, Nagoya 464-8601, Japan
Four novel cerebrosides, termitomycesphins A–D, were isolated from the edible Chinese mushroom Termitomyces albuminosus (Berk.) Heim. (‘Jizong’ in Chinese), shown to induce neuronal differentiation in rat PC12 cells. The absolute stereostructures were elucidated by spectroscopic methods and chemical derivatization. These new cerebrosides have a unique C19 hydroxylated sphingosine base with branching around the middle. Termitomycesphins A and C possessing a C16 α-hydroxy fatty acid showed a higher neuritogenic activity than did termitomycesphins B and D possessing a C18 α-hydroxy fatty acid.
glycolipids, fungi, biologically active compounds
Structure type: monomer ; 766.5421 [M+Na]+
C
41H
77NO
10Location inside paper: fig. 1, termitomycesphin C
Trivial name: termitomycesphin C
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, FAB-MS, TLC, HPLC, HR-ESI-MS, DQF-COSY, HMBC, HMQC, bioassay, optical rotation
Biological activity: induces neuronal differentiation in rat PC12 cells
Related record ID(s): 40549, 40812, 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, 42279, 42280, 42281, 42282, 42287, 42288, 43418, 43419, 43420, 43672, 43673, 43674, 43679, 43680, 43704
NCBI Taxonomy refs (TaxIDs): 79931
Show glycosyltransferases
NMR conditions: in C5D5N
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
1 bDGlcp 105.5 75.0 78.4 71.5 78.5 62.6
2 lR2HOPam
Subst
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
1 bDGlcp 4.90 4.02 4.19 4.21 3.89 4.34-4.50
2 lR2HOPam
Subst
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
1 bDGlcp 105.5/4.90 75.0/4.02 78.4/4.19 71.5/4.21 78.5/3.89 62.6/4.34-4.50
2 lR2HOPam
Subst
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 1 | bDGlcp | 4.90 | 4.02 | 4.19 | 4.21 | 3.89 | 4.34
4.50 |
| 2 | lR2HOPam | |
| | Subst | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 1 | bDGlcp | 105.5 | 75.0 | 78.4 | 71.5 | 78.5 | 62.6 |
| 2 | lR2HOPam | |
| | Subst | |
|
There is only one chemically distinct structure:
Found 
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