Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Host organism: Nemopilema nomurai
Associated disease: infection due to Aspergillus fumigatus [ICD11:
XN5Z7 
]
The structure was elucidated in this paperPublication DOI: 10.1016/j.tet.2014.11.063Journal NLM ID: 2984170RPublisher: Pergamon Press
Correspondence: Jung JH <jhjung
pusan.ac.kr>; Liu YH <yonghongliu
scsio.ac.cn>
Institutions: College of Pharmacy, Pusan National University, Busan, Korea, Key Laboratory of Tropical Marine Bio-resources and Ecology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, China, Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou, China
Three new pyrazinoquinazoline indole glucosides (1-3) were isolated from the fungus Aspergillus fumigatus derived from the jellyfish Nemopilema nomurai. Compounds 1-3 represent the first examples of glycosidated fumiquinzoline-type alkaloids from nature. The structures of the compounds were elucidated by spectroscopic methods and ECD/TDDFT calculations. A possible biogenetic pathway was proposed.
Aspergillus fumigatus, pyrazinoquinazoline indole glucosides, jellyfish-derived, ECD/TDDFT
Structure type: monomer ; 646.2120 [M+Na]+, 624.2305 [M+H]+
C
30H
33N
5O
10Location inside paper: Fig. 1, Fig. 4, structure 1, Table 1, 1
Trivial name: fumigatoside B
Compound class: glycoside
Methods: 13C NMR, 1H NMR, NMR-2D, IR, HPLC, extraction, optical rotation measurement, CD, CC, cell growth, HR-ESI-MS, antibacterial assay, cytotoxicity assay, DEPT, ECD
Biological activity: fumigatoside B shows no antibacterial activity and cytotoxicity
Comments, role: atom enumeration is according to the Fig. 1 in the paper
Related record ID(s): 47894, 47895
NCBI Taxonomy refs (TaxIDs): 746128
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
19 bDGlcp1N 90.4 71.5 78.0 70.0 78.3 61.4
Subst 173.3 84.7 149.6 146.5 127.5 134.6 127.5 125.9 120.2 160.8 53.1 38.1 19.0 80.5 88.8 57.8 170.6 135.9 115.3 129.0 125.2 126.1 138.4 19.0
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
19 bDGlcp1N 4.26 3.42 3.36 3.36 3.37 3.72-3.92
Subst - - - - 7.76 7.84 7.54 8.10 - - 5.62 2.14-2.85 1.94 - 5.57 4.55 - - 7.54 7.43 7.27 7.91 - 1.35
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
19 bDGlcp1N 90.4/4.26 71.5/3.42 78.0/3.36 70.0/3.36 78.3/3.37 61.4/3.72-3.92
Subst 127.5/7.76 134.6/7.84 127.5/7.54 125.9/8.10 53.1/5.62 38.1/2.14-2.85 19.0/1.94 88.8/5.57 57.8/4.55 115.3/7.54 129.0/7.43 125.2/7.27 126.1/7.91 19.0/1.35
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 |
|---|
| 19 | bDGlcp1N | 4.26 | 3.42 | 3.36 | 3.36 | 3.37 | 3.72
3.92 | |
| | Subst |
|
|
|
| 7.76 | 7.84 | 7.54 | 8.10 |
|
| 5.62 | 2.14
2.85 | 1.94 |
| 5.57 | 4.55 |
|
| 7.54 | 7.43 | 7.27 | 7.91 |
| 1.35 |
|
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 |
|---|
| 19 | bDGlcp1N | 90.4 | 71.5 | 78.0 | 70.0 | 78.3 | 61.4 | |
| | Subst | 173.3 | 84.7 | 149.6 | 146.5 | 127.5 | 134.6 | 127.5 | 125.9 | 120.2 | 160.8 | 53.1 | 38.1 | 19.0 | 80.5 | 88.8 | 57.8 | 170.6 | 135.9 | 115.3 | 129.0 | 125.2 | 126.1 | 138.4 | 19.0 |
|
There is only one chemically distinct structure:
Found 
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