Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Host organism: Ramalina calicaris
The structure was elucidated in this paperNCBI PubMed ID: 22890540Publication DOI: 10.1055/s-0032-1315211Journal NLM ID: 0066751Publisher: George Thieme
Correspondence: Gao H <tghao
jnu.edu.cn>; Yao XS <tyaoxs
jnu.edu.cn>
Institutions: State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, China, Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou, China, National Center for Drug Screening and State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai, China, Department of Chemistry, Jinan University, Guangzhou, China
Three new azaphilones, chaetomugilin S (1), 7,5′-bis-epi-chaetoviridin A (2), and 7-epi-chaetoviridin E (3), and two new chlorinated phenolic glycosides, globosumoside A (4) and globosumoside B (5), were isolated from the crude extract of the fungal strain Chaetomium elatum No. 89–1–3–1. Their structures were determined by detailed NMR andMS spectroscopic analyses. The absolute configurations of C-7 in chaetomugilin S (1), 7,5′-bis-epi-chaetoviridin A (2), and 7-epi-chaetoviridin E (3) were assigned by CD experiments, and the absolute configurations of 1 and 2 were established by X-ray crystallography. Compounds 1–3 are the first examples of 7R-configurated azaphilones with a chlorinated isochromen from Chaetomium spp. In addition, compounds 1–3 showed inhibitory activity in the cysteine aspartyl-specific protease-3 (caspase-3) enzymatic assay, with IC50 values of 20.6, 10.9, and 7.9 μM, respectively
glycosides, Chaetomium elatum, Chaetomiaceae, azaphilones, chlorinated phenolic, caspase-3 inhibitors
Structure type: monomer ; 401 [M+Na]+; 377 [M–H]−,
C
16H
23ClO
8Location inside paper: Fig.1, structure 4, Table 3
Trivial name: globosumoside A
Compound class: chlorinated phenolic glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, X-ray, ESI-MS, UV, extraction, optical rotation measurement, column chromatography, RP-HPLC, ESI-TOF-MS, enzymatic assay, HMBC, COSY
Comments, role: NMR temperature was not specified; aglycon atom enumeration is in accordance with Fig. 1; strain No. 89–1–3–1 in the culture collection at the Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou
3D data: computer modelling
Related record ID(s): 43793
NCBI Taxonomy refs (TaxIDs): 5150
Show glycosyltransferases
NMR conditions: in DMSO-d6
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9
1,1 bDGlcp 106.3 73.9 76.1 69.4 77.3 60.6
1 Subst 137.6 148.9 99.0 152.1 110.7 135.4 29.5 22.0 14.1
Me 56.0
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9
1,1 bDGlcp 4.41 3.28 3.23 3.19 3.18 3.51-3.67
1 Subst - - 6.51 - - - 2.73-2.87 1.49 0.91
Me 3.75
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9
1,1 bDGlcp 106.3/4.41 73.9/3.28 76.1/3.23 69.4/3.19 77.3/3.18 60.6/3.51-3.67
1 Subst 99.0/6.51 29.5/2.73-2.87 22.0/1.49 14.1/0.91
Me 56.0/3.75
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 |
|---|
| 1,1 | bDGlcp | 4.41 | 3.28 | 3.23 | 3.19 | 3.18 | 3.51
3.67 | |
| 1 | Subst |
|
| 6.51 |
|
|
| 2.73
2.87 | 1.49 | 0.91 |
| | Me | 3.75 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 |
|---|
| 1,1 | bDGlcp | 106.3 | 73.9 | 76.1 | 69.4 | 77.3 | 60.6 | |
| 1 | Subst | 137.6 | 148.9 | 99.0 | 152.1 | 110.7 | 135.4 | 29.5 | 22.0 | 14.1 |
| | Me | 56.0 | |
|
There is only one chemically distinct structure:
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Host organism: Ramalina calicaris
The structure was elucidated in this paperNCBI PubMed ID: 22890540Publication DOI: 10.1055/s-0032-1315211Journal NLM ID: 0066751Publisher: George Thieme
Correspondence: Gao H <tghao
jnu.edu.cn>; Yao XS <tyaoxs
jnu.edu.cn>
Institutions: State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, China, Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou, China, National Center for Drug Screening and State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai, China, Department of Chemistry, Jinan University, Guangzhou, China
Three new azaphilones, chaetomugilin S (1), 7,5′-bis-epi-chaetoviridin A (2), and 7-epi-chaetoviridin E (3), and two new chlorinated phenolic glycosides, globosumoside A (4) and globosumoside B (5), were isolated from the crude extract of the fungal strain Chaetomium elatum No. 89–1–3–1. Their structures were determined by detailed NMR andMS spectroscopic analyses. The absolute configurations of C-7 in chaetomugilin S (1), 7,5′-bis-epi-chaetoviridin A (2), and 7-epi-chaetoviridin E (3) were assigned by CD experiments, and the absolute configurations of 1 and 2 were established by X-ray crystallography. Compounds 1–3 are the first examples of 7R-configurated azaphilones with a chlorinated isochromen from Chaetomium spp. In addition, compounds 1–3 showed inhibitory activity in the cysteine aspartyl-specific protease-3 (caspase-3) enzymatic assay, with IC50 values of 20.6, 10.9, and 7.9 μM, respectively
glycosides, Chaetomium elatum, Chaetomiaceae, azaphilones, chlorinated phenolic, caspase-3 inhibitors
Structure type: monomer ; 443 [M+Na]+; 419 [M–H]−
C
18H
25ClO
9Location inside paper: Fig.1, structure 5, Table 3
Trivial name: globosumoside B
Compound class: chlorinated phenolic glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, X-ray, ESI-MS, UV, extraction, optical rotation measurement, column chromatography, RP-HPLC, ESI-TOF-MS, enzymatic assay, HMBC, COSY
Comments, role: NMR temperature was not specified; aglycon atom enumeration is in accordance with Fig. 1; strain No. 89–1–3–1 in the culture collection at the Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, Guangzhou
Related record ID(s): 43792
NCBI Taxonomy refs (TaxIDs): 5150
Show glycosyltransferases
NMR conditions: in DMSO-d6
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9
1,1,6 Ac 170.0 20.5
1,1 bDGlcp 105.9 73.8 75.7 69.6 73.9 63.3
1 Subst 137.4 148.8 98.9 152.1 110.6 135.2 29.5 21.7 14.0
Me 56.0
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9
1,1,6 Ac - 2.00
1,1 bDGlcp 4.48 3.31 3.29 3.19 3.47 4.10-4.25
1 Subst - - 6.52 - - - 2.66-2.84 1.49 0.87
Me 3.75
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9
1,1,6 Ac 20.5/2.00
1,1 bDGlcp 105.9/4.48 73.8/3.31 75.7/3.29 69.6/3.19 73.9/3.47 63.3/4.10-4.25
1 Subst 98.9/6.52 29.5/2.66-2.84 21.7/1.49 14.0/0.87
Me 56.0/3.75
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 |
|---|
| 1,1,6 | Ac |
| 2.00 | |
| 1,1 | bDGlcp | 4.48 | 3.31 | 3.29 | 3.19 | 3.47 | 4.10
4.25 | |
| 1 | Subst |
|
| 6.52 |
|
|
| 2.66
2.84 | 1.49 | 0.87 |
| | Me | 3.75 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 |
|---|
| 1,1,6 | Ac | 170.0 | 20.5 | |
| 1,1 | bDGlcp | 105.9 | 73.8 | 75.7 | 69.6 | 73.9 | 63.3 | |
| 1 | Subst | 137.4 | 148.8 | 98.9 | 152.1 | 110.6 | 135.2 | 29.5 | 21.7 | 14.0 |
| | Me | 56.0 | |
|
There is only one chemically distinct structure:
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