Flavusides A and B, Antibacterial Cerebrosides from the Marine-Derived Fungus Aspergillus flavus

• Published in: Chemical & Pharmaceutical Bulletin Vol. 59; no. 9; pp. 1174 - 1177
• Main Authors: Yang, Guohua, Sandjo, Louis, Yun, Keumja, Leutou, Alain Simplice, Kim, Gun-Do, Choi, Hong Dae, Kang, Jung Sook, Hong, Jongki, Son, Byeng Wha
• Format: Journal Article
• Language: English
• Published: Japan The Pharmaceutical Society of Japan 2011; Pharmaceutical Society of Japan; Japan Science and Technology Agency
• Subjects: 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
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.59.1174

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.