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: 33289426Publication DOI: 10.1080/14786419.2020.1851226Journal NLM ID: 101167924Publisher: Milton Park, UK : Taylor & Francis Health Sciences
Correspondence: Zhu H <zhuhucheng
hust.edu.cn>; Zhang Y <zhangyh
mails.tjmu.edu.cn>
Institutions: Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, China, School of Pharmaceutical Sciences, Gannan Medical University, Ganzhou, China, Guangdong Microbial Culture Collection Center (GDMCC), Guangdong Institute of Microbiology, Guangdong Academy of Sciences, Guangzhou, China, Jiangxi University of Traditional Chinese Medicine, Nanchang, China
Two new phenolic glucosides, including a new O-glycoside (1) and a new C-glycoside (2), were isolated from a marine-derived fungus Aspergillus sp. The structures of new compounds were elucidated through interpretations of spectroscopic evidence and high-resolution electrospray ionization mass spectrometry. The hexose unit of 1 was identified as β-D-glucose by comparison with an authentic sample via HPLC after acid hydrolysis and derivatization. All compounds were evaluated for their ability to inhibit LPS-induced NO production in RAW264.7 macrophages, but none of them displayed significant activity.
glucoside, Aspergillus sp., phenolic
Structure type: monomer ; 419.2052 [M+Na]+
C
21H
32O
7Location inside paper: Fig. 1, 1, supplementary materials, Table S1, 1
Trivial name: phenolic glucoside, 2-(hydroxymethyl)-6-(3-methylbut-2-en-1-yl)-3-propylphenyl-O-β-D-glucoside
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, IR, HPLC, UV, extraction, optical rotation measurement, CC, cell growth, RNA sequencing, HR-ESI-MS, evaporation, ECD, anti-inflammatory assays
Related record ID(s): 50588
NCBI Taxonomy refs (TaxIDs): 5052Reference(s) to other database(s): GenDB:2167894
Show glycosyltransferases
NMR conditions: in DMSO-d6
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15
1 bDGlcp 104.4 74.1 76.5 70.5 76.4 61.4
Subst 152.6 133.4 141.1 125.5 128.7 131.8 33.9 24.3 14.3 55.1 27.5 123.6 131.4 25.6 17.8
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15
1 bDGlcp 4.52 3.31 3.25 3.07 3.07 3.38-3.66
Subst - - - 6.92 6.99 - 2.64 1.55 0.93 4.45-4.73 3.45 5.26 - 1.69 1.67
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
1 bDGlcp 104.4/4.52 74.1/3.31 76.5/3.25 70.5/3.07 76.4/3.07 61.4/3.38-3.66
Subst 125.5/6.92 128.7/6.99 33.9/2.64 24.3/1.55 14.3/0.93 55.1/4.45-4.73 27.5/3.45 123.6/5.26 25.6/1.69 17.8/1.67
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 |
|---|
| 1 | bDGlcp | 4.52 | 3.31 | 3.25 | 3.07 | 3.07 | 3.38
3.66 | |
| | Subst |
|
|
| 6.92 | 6.99 |
| 2.64 | 1.55 | 0.93 | 4.45
4.73 | 3.45 | 5.26 |
| 1.69 | 1.67 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 |
|---|
| 1 | bDGlcp | 104.4 | 74.1 | 76.5 | 70.5 | 76.4 | 61.4 | |
| | Subst | 152.6 | 133.4 | 141.1 | 125.5 | 128.7 | 131.8 | 33.9 | 24.3 | 14.3 | 55.1 | 27.5 | 123.6 | 131.4 | 25.6 | 17.8 |
|
There is only one chemically distinct structure:
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