Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Host organism: Excoecaria agallocha
Organ / tissue: mycelium
The structure was elucidated in this paperPublication DOI: 10.1007/s10600-013-0497-0Journal NLM ID: 0151571Publisher: Tashkent: Izdatelstvo Fan
Correspondence: Lei F <leifuhou
163.com>
Institutions: College of Chemistry and Ecology Engineering, Guangxi University for Nationalities, Nanning, China, Department of Chemistry and Engineering, Guilin Medical University, Guilin, China, College of Chemistry and Chemical Engineering, Sun Yat-Sen (Zhongshan) University, Guangzhou, China
A new xanthone O-glycoside, 3-O-(6-O-α-L-arabinopyranosyl)-β-D-glucopyranosyl-1,4-dimethoxyxanthone (1), together with three known compounds, phomapyrone D (2), 2-methoxy-3,4-methylenedioxybenzophenone (3), and cyclo(D-6-Hyp-L-Phe) (4), was isolated from the mangrove endophytic fungus, Phomopsis sp. (ZH76). Their structures were determined by analysis of spectroscopic data. Compound 1 inhibited HEp-2 and HepG2 cells with IC50 values of 9 and 16 μmol/mL, respectively.
structure elucidation, cytotoxic activity, mangrove endophytic fungus, xanthone O-glycoside
Structure type: monomer ; 565.1552 [M-H]-
C
26H
30O
14Location inside paper: compound 1, p. 27, Table 1
Compound class: phenolic glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, TLC, UV, optical rotation measurement, HMBC, HR-FAB-MS, HCl hydrolysis, FAB
Biological activity: compound 1 exhibited cytotoxicity against HEp-2 and HepG2 cells with IC50 values of 9 and 16 μg/mL, respectively
Comments, role: NMR temperature was not stratified, compound 1 was obtained from Phomopsis ZH76 mycelium; Phomopsis sp. ZH76 was isolated from the stem of E. agallocha
NCBI Taxonomy refs (TaxIDs): 34399
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
3,6 aLArap 103.4 70.5 72.7 67.3 64.8
3 bDGlcp 101.5 73.4 76.1 69.9 75.6 68.3
1 Me 56.3
4 Me 61.7
Subst 156.8 96.3 157.0 138.5 148.2 154.4 117.8 134.6 124.1 125.6 121.6 179.8 110.9
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13
3,6 aLArap 4.17 3.46 3.35 3.58 3.65
3 bDGlcp 4.97 3.35 3.37 3.23 3.62 3.55-3.96
1 Me 3.81
4 Me 3.85
Subst - 6.87 - - - - 7.64 7.78 7.42 8.09 - - -
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
3,6 aLArap 103.4/4.17 70.5/3.46 72.7/3.35 67.3/3.58 64.8/3.65
3 bDGlcp 101.5/4.97 73.4/3.35 76.1/3.37 69.9/3.23 75.6/3.62 68.3/3.55-3.96
1 Me 56.3/3.81
4 Me 61.7/3.85
Subst 96.3/6.87 117.8/7.64 134.6/7.78 124.1/7.42 125.6/8.09
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 |
|---|
| 3,6 | aLArap | 4.17 | 3.46 | 3.35 | 3.58 | 3.65 | |
| 3 | bDGlcp | 4.97 | 3.35 | 3.37 | 3.23 | 3.62 | 3.55
3.96 | |
| 1 | Me | 3.81 | |
| 4 | Me | 3.85 | |
| | Subst |
| 6.87 |
|
|
|
| 7.64 | 7.78 | 7.42 | 8.09 |
|
|
|
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 |
|---|
| 3,6 | aLArap | 103.4 | 70.5 | 72.7 | 67.3 | 64.8 | |
| 3 | bDGlcp | 101.5 | 73.4 | 76.1 | 69.9 | 75.6 | 68.3 | |
| 1 | Me | 56.3 | |
| 4 | Me | 61.7 | |
| | Subst | 156.8 | 96.3 | 157.0 | 138.5 | 148.2 | 154.4 | 117.8 | 134.6 | 124.1 | 125.6 | 121.6 | 179.8 | 110.9 |
|
There is only one chemically distinct structure:
Found 
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