Flavusides A and B, Antibacterial Cerebrosides from the Marine-Derived Fungus Aspergillus flavus
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 abs...
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| Published in: | Chemical & Pharmaceutical Bulletin Vol. 59; no. 9; pp. 1174 - 1177 |
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| Format: | Journal Article |
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Japan
The Pharmaceutical Society of Japan
2011
Pharmaceutical Society of Japan Japan Science and Technology Agency |
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| Abstract | 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. |
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| AbstractList | 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. 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. Marine microorganisms, particularly marine fungi, have recently gained prominence as an important source of biologically active secondary metabolites. 1) |
| Author | Kang, Jung Sook Yang, Guohua Kim, Gun-Do Son, Byeng Wha Sandjo, Louis Yun, Keumja Leutou, Alain Simplice Hong, Jongki Choi, Hong Dae |
| Author_xml | – sequence: 1 fullname: Yang, Guohua organization: Department of Chemistry, Pukyong National University – sequence: 2 fullname: Sandjo, Louis organization: Department of Chemistry, Pukyong National University – sequence: 3 fullname: Yun, Keumja organization: Department of Chemistry, Pukyong National University – sequence: 4 fullname: Leutou, Alain Simplice organization: Department of Chemistry, Pukyong National University – sequence: 5 fullname: Kim, Gun-Do organization: Department of Chemistry, Dongeui University – sequence: 6 fullname: Choi, Hong Dae organization: College of Dentistry, Pusan National University – sequence: 7 fullname: Kang, Jung Sook organization: College of Pharmacy, Kyung Hee University – sequence: 8 fullname: Hong, Jongki organization: Department of Chemistry, Pukyong National University – sequence: 9 fullname: Son, Byeng Wha organization: Department of Chemistry, Pukyong National University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/21881265$$D View this record in MEDLINE/PubMed |
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| SubjectTerms | Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - isolation & purification Anti-Bacterial Agents - pharmacology antibacterial activity Aquatic Organisms - microbiology Aspergillus flavus Aspergillus flavus - chemistry cerebroside Cerebrosides - chemistry Cerebrosides - isolation & purification Cerebrosides - pharmacology Drug Resistance, Bacterial - drug effects flavuside Glycosphingolipids - chemistry Glycosphingolipids - isolation & purification Glycosphingolipids - pharmacology Magnetic Resonance Spectroscopy marine-derived fungus Methicillin-Resistant Staphylococcus aureus - drug effects Microbial Sensitivity Tests Molecular Conformation Staphylococcus aureus - drug effects Tandem Mass Spectrometry |
| Title | Flavusides A and B, Antibacterial Cerebrosides from the Marine-Derived Fungus Aspergillus flavus |
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