Characterization of four new antifungal yanuthones from Aspergillus niger

Four new yanuthone analogs ( 1–4 ) were isolated from the filamentous fungus Aspergillus niger . The structures of the new compounds were elucidated on the basis of UHPLC-DAD-HRMS data and one-dimensional and two-dimensional NMR spectroscopy. Labeling studies with 13 C 8 -6-methylsalicylic acid iden...

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Bibliographic Details
Published in:Journal of antibiotics 2015-03, Vol.68 (3), p.201-205
Main Authors: Petersen, Lene M, Holm, Dorte K, Knudsen, Peter B, Nielsen, Kristian F, Gotfredsen, Charlotte H, Mortensen, Uffe H, Larsen, Thomas O
Format: Article
Language:English
Subjects:
631/1647/2258
631/326/22/1292
Antifungal Agents - chemistry
Antifungal Agents - isolation & purification
Antifungal Agents - pharmacology
Aspergillus niger - metabolism
Bacteriology
Biomedical and Life Sciences
Bioorganic Chemistry
Candida albicans - drug effects
Life Sciences
Magnetic Resonance Spectroscopy
Medicinal Chemistry
Microbiology
Organic Chemistry
original-article
Yeasts
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Summary:Four new yanuthone analogs ( 1–4 ) were isolated from the filamentous fungus Aspergillus niger . The structures of the new compounds were elucidated on the basis of UHPLC-DAD-HRMS data and one-dimensional and two-dimensional NMR spectroscopy. Labeling studies with 13 C 8 -6-methylsalicylic acid identified three class I yanuthones originating from the polyketide 6-methylsalicylic acid (yanuthone K, L and M ( 1–3 )) and a class II yanuthone, which was named yanuthone X 2 ( 4 ). The four new compounds were tested toward the pathogenic yeast Candida albicans and all displayed antifungal activity. Yanuthone X 2 represents the first example of a bioactive class II yanuthone, demonstrating the pharmaceutical potential of this class.
ISSN:0021-8820
1881-1469
DOI:10.1038/ja.2014.130