Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Associated disease: infection due to Aspergillus fumigatus [ICD11:
XN5Z7 
]
NCBI PubMed ID: 30977375Publication DOI: 10.1021/acs.orglett.9b00984Journal NLM ID: 100890393Publisher: American Chemical Society
Correspondence: Liu H <liuhw
im.ac.cn>; Yin WB <yinwb
im.ac.cn>
Institutions: State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, China, Savaid Medical School, University of Chinese Academy of Sciences, Beijing, China, Department of Medical Microbiology and Immunology, University of Wisconsin-Madison, Madison, USA, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, China
A rare fungal hopane-type triterpenoid glycoside fumihopaside A was identified by genome mining in combination with HPLC-MS/MS in Aspergillus fumigatus. Combining genetic deletions in A. fumigatus with heterologous reconstitutions in Aspergillus nidulans of the afum gene cluster, we identified one fungal squalene hopane cyclase AfumA charging the cyclization of the hopene skeleton, one cytochrome P450, and one UDP-glycosyltransferase. Bioassays indicated that fumihopaside A plays important roles in protecting A. fumigatus against heat or ultraviolet stress.
Aspergillus fumigatus, triterpenoid glycoside, fumihopaside A
Structure type: monomer ; 633.4008 [M-H]-
C
36H
58O
9Location inside paper: Fig. 2, 2, supplementary material, Table S6, 2
Trivial name: fumihopaside B
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, DNA techniques, ESI-MS, ESI-MS/MS, gene expression, HPLC-ELSD, HPLC-MS/MS
Enzymes that release or process the structure: AfumA, AfumB, AfumC
Related record ID(s): 49639
NCBI Taxonomy refs (TaxIDs): 746128
Show glycosyltransferases
NMR conditions: in C5D5N
[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
24 bDGlcp 101.8 74.2 76.0 72.6 75.2 63.4
Subst 40.1 29.2 79.6 43.5 56.9 20.7 34.6 42.6 51.3 37.9 21.3 21.9 50.1 42.4 34.1 24.6 55.3 46.0 42.5 27.1 40.5 146.4 25.2 72.1 16.3 17.3 16.9 16.5 122.3 172.1
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
24 bDGlcp 5.28 4.19 4.61 4.27 4.44 4.43-4.52
Subst 0.98-1.70 1.90-2.09 3.55 - 0.87 1.50-1.98 1.15-1.35 - 1.25 - 1.67-2.00 1.31-1.51 1.38 - 1.13-1.38 1.40-1.50 1.46 - 1.07-1.68 1.99 3.81 - 1.48 3.81-4.55 1.09 1.02 0.90 0.77 5.76-6.61 -
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
24 bDGlcp 101.8/5.28 74.2/4.19 76.0/4.61 72.6/4.27 75.2/4.44 63.4/4.43-4.52
Subst 40.1/0.98-1.70 29.2/1.90-2.09 79.6/3.55 56.9/0.87 20.7/1.50-1.98 34.6/1.15-1.35 51.3/1.25 21.3/1.67-2.00 21.9/1.31-1.51 50.1/1.38 34.1/1.13-1.38 24.6/1.40-1.50 55.3/1.46 42.5/1.07-1.68 27.1/1.99 40.5/3.81 25.2/1.48 72.1/3.81-4.55 16.3/1.09 17.3/1.02 16.9/0.90 16.5/0.77 122.3/5.76-6.61
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 |
|---|
| 24 | bDGlcp | 5.28 | 4.19 | 4.61 | 4.27 | 4.44 | 4.43
4.52 | |
| | Subst | 0.98
1.70 | 1.90
2.09 | 3.55 |
| 0.87 | 1.50
1.98 | 1.15
1.35 |
| 1.25 |
| 1.67
2.00 | 1.31
1.51 | 1.38 |
| 1.13
1.38 | 1.40
1.50 | 1.46 |
| 1.07
1.68 | 1.99 | 3.81 |
| 1.48 | 3.81
4.55 | 1.09 | 1.02 | 0.90 | 0.77 | 5.76
6.61 |
|
|
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 |
|---|
| 24 | bDGlcp | 101.8 | 74.2 | 76.0 | 72.6 | 75.2 | 63.4 | |
| | Subst | 40.1 | 29.2 | 79.6 | 43.5 | 56.9 | 20.7 | 34.6 | 42.6 | 51.3 | 37.9 | 21.3 | 21.9 | 50.1 | 42.4 | 34.1 | 24.6 | 55.3 | 46.0 | 42.5 | 27.1 | 40.5 | 146.4 | 25.2 | 72.1 | 16.3 | 17.3 | 16.9 | 16.5 | 122.3 | 172.1 |
|
There is only one chemically distinct structure:
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