Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Associated disease: infection due to Aspergillus [ICD11:
XN0WC 
]
NCBI PubMed ID: 25944534Publication DOI: 10.1038/ja.2015.43Journal NLM ID: 0151115Publisher: London: Nature Publishing Group
Correspondence: Shiomi K <shiomi
lisci.kitasato-u.ac.jp>; Ōmura S <omuras
insti.kitasato-u.ac.jp>
Institutions: Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Kyoto, Japan, Faculty of Pharmaceutical Sciences, University of Tokushima, Tokushima, Japan, Kitasato Institute for Life Sciences, Kitasato University, Tokyo, Japan, Department of Drug Discovery Sciences, Graduate School of Infection Control Sciences, Kitasato University, Tokyo, Japan, Department of Chemistry, School of Science, Kitasato University, Kanagawa, Japan, Research Organization for Infection Control Sciences, Kitasato University, Tokyo, Japan, Insect Growth Regulation Research Unit, National Institute of Agrobiological Sciences, Tsukuba, Japan, Institute for Genome Research, University of Tokushima, Tokushima, Japan
A mitochondrial respiration inhibitor 1 was isolated from the fungus Aspergillus sp., (strain FKI-6682) and its structure was elucidated to be a lanostane-type triterpenoid. Our data demonstrate that 1 inhibited the mitochondrial respiratory system in yeast, particularly yeast grown in glycerol medium.
Aspergillus, Saccharomyces cerevisiae, fungicidal activity, ascosteroside C
Structure type: monomer
Location inside paper: Table 1, ascosteroside A
Trivial name: ascosteroside A
Compound class: glycan, glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, ESI-MS/MS, biological assays, HPLC, UV, extraction, optical rotation measurement, CC, cell growth, HR-ESI-MS, cytotoxicity assay
Comments, role: atom enumeration is according to the Fig. 1, A in the paper
Related record ID(s): 45589, 45930, 47965
NCBI Taxonomy refs (TaxIDs): 1546023
Show glycosyltransferases
NMR conditions: in CD3OD
[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 C20 C21 C22 C23 C24 C25 C26 C27 C28 C29 C30
3,4 Me 60.8
3 aDGlcp 96.8 73.7 75.2 81.2 73.0 62.2
Subst 36.3 29.5 76.8 151.7 47.9 22.1 27.1 128.9 140.8 40.6 24.6 34.1 47.5 68.0 73.3 44.6 51.8 18.9 19.4 36.7 19.2 36.1 31.9 157.7 34.9 22.3 22.5 106.9 104.4 179.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17 H18 H19 H20 H21 H22 H23 H24 H25 H26 H27 H28 H29 H30
3,4 Me 3.55
3 aDGlcp 4.98 3.41 3.84 3.10 3.61 3.62-3.69
Subst 1.46-1.88 1.46-2.08 4.06 - 2.02 1.58-1.77 1.99-2.71 - - - 2.12-2.28 1.70-2.19 - - 4.60 1.49-2.66 1.44 1.11 0.93 1.60 0.96 1.16-1.57 1.92-2.10 - 2.24 1.03 1.03 4.65-4.72 4.65-5.19 -
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 C20/H20 C21/H21 C22/H22 C23/H23 C24/H24 C25/H25 C26/H26 C27/H27 C28/H28 C29/H29 C30/H30
3,4 Me 60.8/3.55
3 aDGlcp 96.8/4.98 73.7/3.41 75.2/3.84 81.2/3.10 73.0/3.61 62.2/3.62-3.69
Subst 36.3/1.46-1.88 29.5/1.46-2.08 76.8/4.06 47.9/2.02 22.1/1.58-1.77 27.1/1.99-2.71 24.6/2.12-2.28 34.1/1.70-2.19 73.3/4.60 44.6/1.49-2.66 51.8/1.44 18.9/1.11 19.4/0.93 36.7/1.60 19.2/0.96 36.1/1.16-1.57 31.9/1.92-2.10 34.9/2.24 22.3/1.03 22.5/1.03 106.9/4.65-4.72 104.4/4.65-5.19
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 | H17 | H18 | H19 | H20 | H21 | H22 | H23 | H24 | H25 | H26 | H27 | H28 | H29 | H30 |
|---|
| 3,4 | Me | 3.55 | |
| 3 | aDGlcp | 4.98 | 3.41 | 3.84 | 3.10 | 3.61 | 3.62
3.69 | |
| | Subst | 1.46
1.88 | 1.46
2.08 | 4.06 |
| 2.02 | 1.58
1.77 | 1.99
2.71 |
|
|
| 2.12
2.28 | 1.70
2.19 |
|
| 4.60 | 1.49
2.66 | 1.44 | 1.11 | 0.93 | 1.60 | 0.96 | 1.16
1.57 | 1.92
2.10 |
| 2.24 | 1.03 | 1.03 | 4.65
4.72 | 4.65
5.19 |
|
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 | C17 | C18 | C19 | C20 | C21 | C22 | C23 | C24 | C25 | C26 | C27 | C28 | C29 | C30 |
|---|
| 3,4 | Me | 60.8 | |
| 3 | aDGlcp | 96.8 | 73.7 | 75.2 | 81.2 | 73.0 | 62.2 | |
| | Subst | 36.3 | 29.5 | 76.8 | 151.7 | 47.9 | 22.1 | 27.1 | 128.9 | 140.8 | 40.6 | 24.6 | 34.1 | 47.5 | 68.0 | 73.3 | 44.6 | 51.8 | 18.9 | 19.4 | 36.7 | 19.2 | 36.1 | 31.9 | 157.7 | 34.9 | 22.3 | 22.5 | 106.9 | 104.4 | 179.3 |
|
There is only one chemically distinct structure:
Found 
report error
(previously named: Aspergillus flaschentraegeri FKI-6682)