Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Organ / tissue: myceliumAssociated disease: infection due to Aspergillus flavus [ICD11:
XN6B8 
]
The structure was elucidated in this paperNCBI PubMed ID: 21881265Publication DOI: 10.1248/cpb.59.1174Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Correspondence: sonbw
pknu.ac.kr
Institutions: Department of Chemistry, Pukyong National University, Busan, Korea, Department of Chemistry, Dongeui University, Busan, Korea, College of Dentistry, Pusan National University, Yangsan, Korea, College of Pharmacy, Kyung Hee University, Seoul, South Korea
Flavusides A (1) and B (2), two new antibacterial cerebroside derivatives, and the previously described phomaligol A (3), kojic acid (4), methyl kojic acid (5), and dimethyl kojic acid (6) have been isolated from the extract of a marine isolate of the fungus Aspergillus flavus. The structure and absolute stereochemistry of two cerebrosides were assigned on the basis of NMR and Tandem FAB-MS/MS experiments. Compounds 1, 2, and 3 exhibited a mild antibacterial activity against Staphylococcus aureus, methicillin-resistant S. aureus, and multidrug-resistant S. aureus. The minimum inhibitory concentration (MIC) values for each strain are as follows: compounds 1 and 2 showed 15.6 μg/ml for S. aureus and 31.2 μg/ml for methicillin-resistant S. aureus and multidrug-resistant S. aureus, and compound 3 exhibited 31.2 μg/ml for S. aureus and methicillin-resistant S. aureus and 62.5 μg/ml for multidrug-resistant S. aureus.
antibacterial activity, cerebroside, flavuside, marine-derived fungus, Aspergillus flavus
Structure type: monomer ; 776.5644 [M+Na]+
C
43H
79NO
9Location inside paper: flavuside B, p.1174, table 1
Trivial name: flavuside B
Compound class: glycosphingolipid, cerebroside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, FAB-MS, biological assays, FTIR, NMR-1D, methanolysis, HPLC, UV, extraction, optical rotation measurement, CC
Biological activity: flavuside exhibited a mild antibacterial activity; minimum inhibitory concentration values are: 15.6 μg/ml for Staphylococcus aureus and 31.2 m g/ml for methicillin-resistant Staphylococcus aureus and multidrug-resistant Staphylococcus aureus
Related record ID(s): 40549, 40812, 40813, 40814, 42250, 42251, 42252, 42253, 42254, 42255, 42256, 42257, 42258, 42259, 42260, 42261, 42262, 42263, 42264, 42265, 42266, 42267, 42268, 42269, 42270, 42271, 42272, 42273, 42274, 42275, 42276, 42279, 42280, 42281, 42282, 42287, 42288, 43402, 43403, 43419, 43420, 43679
NCBI Taxonomy refs (TaxIDs): 5059
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 C17 C18
1 bDGlcp
2 lR2HOC18={t3} 172.0 71.9 129.0 130.9 31.6 28.7-31.3 28.7-31.3 28.7-31.3 28.7-31.3 28.7-31.3 28.7-31.3 28.7-31.3 28.7-31.3 28.7-31.3 28.7-31.3 28.7-31.3 22.1 13.9
Subst 68.6 52.9 70.5 130.9 130.9 31.2 27.3 31.3 123.5 134.9 27.4 28.7-31.3 28.7-31.3 28.7-31.3 28.7-31.3 22.1 13.9 15.7
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17 H18 H19
1 bDGlcp 4.11 2.95 3.13 3.03 3.06 3.44-3.66
2 lR2HOC18={t3} - 4.29 5.43 5.67 1.95 1.23 1.23-1.95 1.23 1.23 1.23 1.23 1.23 1.23 1.23 1.23 1.23 1.23 0.84
Subst 3.50-3.93 3.79 3.98 5.36 5.56 1.91 1.93 1.95 5.09 - 1.90 1.32 1.23 1.23 1.23 1.23 1.23 0.84 1.54
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 C17/H17 C18/H18 C19/H19
1 bDGlcp NMR TSV error 2: unequal length of 13C and 1H datasets
2 lR2HOC18={t3} 71.9/4.29 129.0/5.43 130.9/5.67 31.6/1.95 28.7-31.3/1.23 28.7-31.3/1.23-1.95 28.7-31.3/1.23 28.7-31.3/1.23 28.7-31.3/1.23 28.7-31.3/1.23 28.7-31.3/1.23 28.7-31.3/1.23 28.7-31.3/1.23 28.7-31.3/1.23 28.7-31.3/1.23 22.1/1.23 13.9/0.84
Subst NMR TSV error 2: unequal length of 13C and 1H datasets
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 | H17 | H18 | H19 |
|---|
| 1 | bDGlcp | 4.11 | 2.95 | 3.13 | 3.03 | 3.06 | 3.44
3.66 | |
| 2 | lR2HOC18={t3} |
| 4.29 | 5.43 | 5.67 | 1.95 | 1.23 | 1.23
1.95 | 1.23 | 1.23 | 1.23 | 1.23 | 1.23 | 1.23 | 1.23 | 1.23 | 1.23 | 1.23 | 0.84 | |
| | Subst | 3.50
3.93 | 3.79 | 3.98 | 5.36 | 5.56 | 1.91 | 1.93 | 1.95 | 5.09 |
| 1.90 | 1.32 | 1.23 | 1.23 | 1.23 | 1.23 | 1.23 | 0.84 | 1.54 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 | C17 | C18 |
|---|
| 1 | bDGlcp | |
| 2 | lR2HOC18={t3} | 172.0 | 71.9 | 129.0 | 130.9 | 31.6 | 28.7
31.3 | 28.7
31.3 | 28.7
31.3 | 28.7
31.3 | 28.7
31.3 | 28.7
31.3 | 28.7
31.3 | 28.7
31.3 | 28.7
31.3 | 28.7
31.3 | 28.7
31.3 | 22.1 | 13.9 |
| | Subst | 68.6 | 52.9 | 70.5 | 130.9 | 130.9 | 31.2 | 27.3 | 31.3 | 123.5 | 134.9 | 27.4 | 28.7
31.3 | 28.7
31.3 | 28.7
31.3 | 28.7
31.3 | 22.1 | 13.9 | 15.7 |
|
There is only one chemically distinct structure:
report error
Found 1 record.
Displayed record 1
