Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Organ / tissue: mycelium
The structure was elucidated in this paperNCBI PubMed ID: 16755063Publication DOI: 10.1248/cpb.54.882Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Correspondence: Sona BW <sonbw
pknu.ac.kr>
Institutions: Department of Chemistry, Pukyong National University, Busan, Korea, College of Dentistry, Pusan National University, Busan, Korea, Department of Chemistry, Dongeui University, Busan, Korea
A new anthracene glycoside, asperflavin ribofuranoside (1), and the previously described polyketides, flavoglaucin (2), isodihydroauroglaucin (3), and citrinin (4) have been isolated from the marine-derived fungus Microsporum sp. The structure and absolute stereochemistry of a new compound (1) was assigned on the basis of physicochemical data. Compounds 1—3 exhibited a significant radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) with IC50 values of 14.2, 11.3, and 11.5 μM, respectively, which are more potent than the positive control, ascorbic acid (IC50, 20 μM). Compound 1 also showed a moderate antibacterial activity against the methicillin-resistant and multidrug-resistant Staphylococcus aureus (MRSA and MDRSA) with MIC value of 50 μg/ml.
radical scavenging activity, Microsporum sp., asperflavin ribofuranoside, flavoglaucin, isodihydroauroglaucin, citrinin
Structure type: monomer ; 421.4265 [M+H]+
C
21H
24O
9Location inside paper: p. 882, table 1, asperflavin ribofuranoside (1)
Trivial name: asperflavin ribofuranoside ((+)-6-O-(α-D-ribofuranosyl)-3,4-dihydro-3,6,9-trihydroxy-8-methoxy-3-methylanthracen-1(2H)-one)
Compound class: anthracene glycoside
Contained glycoepitopes: IEDB_149136
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, IR, GC-MS, sugar analysis, acid hydrolysis, HPLC, UV, extraction, antibacterial assay, radical scavenging assay, HR-FAB-MS, LR-FAB-MS
Biological activity: radical scavenging activity
Comments, role: the NMR temperature was not indicated. NMR atom numbering is as indicated in the paper. NMR solvent was specified as DMSO, probably implying DMSO-d6.
NCBI Taxonomy refs (TaxIDs): 34392
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 C16
3 aDRibf 99.9 71.5 69.2 86.5 61.5
Subst 203.7 51.5 69.4 28.8 42.7 138.1 102.2 159.4 98.7 160.6 55.8 109.5-109.6 164.5 109.5-109.6 116.5 141.0
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16
3 aDRibf 5.75 4.11 3.95 4.01 3.49
Subst - 2.64-2.86 - 1.27 2.91-3.02 - 6.84 - 6.58 - 3.87 - - - 6.91 -
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 C16/H16
3 aDRibf 99.9/5.75 71.5/4.11 69.2/3.95 86.5/4.01 61.5/3.49
Subst 51.5/2.64-2.86 28.8/1.27 42.7/2.91-3.02 102.2/6.84 98.7/6.58 55.8/3.87 116.5/6.91
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 |
|---|
| 3 | aDRibf | 5.75 | 4.11 | 3.95 | 4.01 | 3.49 | |
| | Subst |
| 2.64
2.86 |
| 1.27 | 2.91
3.02 |
| 6.84 |
| 6.58 |
| 3.87 |
|
|
| 6.91 |
|
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 |
|---|
| 3 | aDRibf | 99.9 | 71.5 | 69.2 | 86.5 | 61.5 | |
| | Subst | 203.7 | 51.5 | 69.4 | 28.8 | 42.7 | 138.1 | 102.2 | 159.4 | 98.7 | 160.6 | 55.8 | 109.5
109.6 | 164.5 | 109.5
109.6 | 116.5 | 141.0 |
|
There is only one chemically distinct structure:
Found 
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