Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Organ / tissue: spores
The structure was elucidated in this paperPublication DOI: 10.1016/j.tet.2022.133067Journal NLM ID: 2984170RPublisher: Pergamon Press
Correspondence: S.H. Qi <shuhuaqi
scsio.ac.cn>
Institutions: CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou, 510301, Guangdong, Chin
Three new aromatic polyketides (±)-puniceusone A (1), (±)-2,3-dihydroxypropyl 6-ethyl-2,4-dihydroxy-3-methylbenzoate (2), (5-ethyl-3-hydroxy-2-methyl) phenyl-β-D-glucoside (3), and two new isoquinoline alkaloids puniceusine O (4) and (±)-puniceusine P (5), were isolated from the deep-sea-derived fungus Aspergillus puniceus SCSIO z021. Their structures were determined by spectroscopic analyses. Compound 1 contains an uncommon hydrogenated benzochromene scaffold, 3 and 4 are glycosides, and 5 is unexpectedly composed of a polysubstituted benzyl and an isoquinoline nucleus.
Structures, Aspergillus, polyketides, marine-derived fungi, isoquinoline alkaloids
Structure type: monomer ; 315.1438 [M+H]+
C
15H
23O
7Location inside paper: Fig. 1, table 1, table 2, compound 3
Trivial name: (5-ethyl-3-hydroxy-2-methyl)phenyl-β-D-glucoside
Compound class: aromatic polyketide
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, acid hydrolysis, HPLC, UV, extraction, optical rotation measurement, fermentation, HR-ESI-MS, antibacterial assay
Comments, role: NMR temperature was not specified
Related record ID(s): 51773
NCBI Taxonomy refs (TaxIDs): 41744
Show glycosyltransferases
NMR conditions: in DMSO-d6
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9
1 bDGlcp 101.2 73.4 77.0 69.8 76.8 60.8
Subst 156.5 110.3 155.6 108.2 ? 105.7 28.3 15.5 8.5
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9
1 bDGlcp 4.71 3.23 3.24 3.15 3.25 3.45-3.67
Subst - - - 6.32 - 6.42 2.43 1.11 1.96
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9
1 bDGlcp 101.2/4.71 73.4/3.23 77.0/3.24 69.8/3.15 76.8/3.25 60.8/3.45-3.67
Subst 108.2/6.32 105.7/6.42 28.3/2.43 15.5/1.11 8.5/1.96
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 |
|---|
| 1 | bDGlcp | 4.71 | 3.23 | 3.24 | 3.15 | 3.25 | 3.45
3.67 | |
| | Subst |
|
|
| 6.32 |
| 6.42 | 2.43 | 1.11 | 1.96 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 |
|---|
| 1 | bDGlcp | 101.2 | 73.4 | 77.0 | 69.8 | 76.8 | 60.8 | |
| | Subst | 156.5 | 110.3 | 155.6 | 108.2 | ? | 105.7 | 28.3 | 15.5 | 8.5 |
|
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
Found 
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