Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Host organism: Saccharina cichorioides f. sachalinensis
Associated disease: infection due to Aspergillus [ICD11:
XN0WC 
]
The structure was elucidated in this paperNCBI PubMed ID: 31012585Publication DOI: 10.1021/acs.jnatprod.8b00744Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: Zhu H <zhuhucheng
hust.edu.cn>; Zhang Y <zhangyh
mails.tjmu.edu.cn>
Institutions: School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan, China, Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation and Department of Pharmacology, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, China, School of Pharmaceutical Sciences, Gannan Medical University, Ganzhou, China
A chemical investigation of the secondary metabolites of a marine-derived Aspergillus sp. led to the isolation and characterization of 13 phenolic compounds, including 10 new compounds (1-10). Seven new compounds (1-7) are unusual phenolic C-glycosides, while the other new compounds (8-10) are structurally related aglycones. The chemical structures of these new compounds were elucidated by 1D and 2D NMR and HRESIMS spectroscopic analyses. The absolute configurations of these new C-glycosides were determined by comparison of experimental electronic circular dichroism spectra with those of calculated ones. In addition, the anti-inflammatory activities of these compounds were evaluated, and compound 9 significantly inhibited nitric oxide production with an IC50 value of 6.0 ± 0.5 μM in lipopolysaccharide-induced RAW264.7 cells. Moreover, compound 9 also showed anti-inflammatory activity by inhibiting the NF-κB-activated pathway.
Aspergillus, phenolic glycoside, anti-inflammatory activities
Structure type: monomer ; 447.1631 [M+Na]+
C
21H
28O
9Location inside paper: Chart 1, 2, Table 1, 2, Table 2, 2
Trivial name: carnemycin D
Compound class: glycoside
Methods: 13C NMR, 1H NMR, NMR-2D, IR, SDS-PAGE, ELISA, Western blotting, HPLC, UV, extraction, optical rotation measurement, CC, immunofluorescence microscopy, RNA sequencing, HR-ESI-MS, determination of NO production, cytokine production, ECD
Comments, role: NMR temperature was not specified; Atom enumeration is according to the Chart 1, 1 in the paper
Related record ID(s): 49701, 49703, 49704, 49705, 49706, 49707, 49708, 49709
NCBI Taxonomy refs (TaxIDs): 5052
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
3 bD1dGlcp 76.1 73.0 80.1 71.6 82.6 62.7
7 Me 52.4
Subst 105.7 164.1 110.7 162.4 112.4 147.6 173.3 37.6 35.8 132.1 131.8 132.9 127.9 18.1
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14
3 bD1dGlcp 4.91 4.03 3.47 3.47 3.40 3.73-3.85
7 Me 3.91
Subst - - - - 6.27 - - 2.88 2.26 5.54 6.00 6.00 5.59 1.71
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
3 bD1dGlcp 76.1/4.91 73.0/4.03 80.1/3.47 71.6/3.47 82.6/3.40 62.7/3.73-3.85
7 Me 52.4/3.91
Subst 112.4/6.27 37.6/2.88 35.8/2.26 132.1/5.54 131.8/6.00 132.9/6.00 127.9/5.59 18.1/1.71
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 |
|---|
| 3 | bD1dGlcp | 4.91 | 4.03 | 3.47 | 3.47 | 3.40 | 3.73
3.85 | |
| 7 | Me | 3.91 | |
| | Subst |
|
|
|
| 6.27 |
|
| 2.88 | 2.26 | 5.54 | 6.00 | 6.00 | 5.59 | 1.71 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 |
|---|
| 3 | bD1dGlcp | 76.1 | 73.0 | 80.1 | 71.6 | 82.6 | 62.7 | |
| 7 | Me | 52.4 | |
| | Subst | 105.7 | 164.1 | 110.7 | 162.4 | 112.4 | 147.6 | 173.3 | 37.6 | 35.8 | 132.1 | 131.8 | 132.9 | 127.9 | 18.1 |
|
There is only one chemically distinct structure:
Found 
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