Reappraising the structures and distribution of metabolites from black aspergilli containing uncommon 2-benzyl-4H-pyran-4-one and 2-benzylpyridin-4(1H)-one systems
| Autor: | Jon C. Henrikson, Jarrod B. King, Robert H. Cichewicz, Trevor K. Ellis |
|---|---|
| Rok vydání: | 2011 |
| Předmět: |
Stereochemistry
Pharmaceutical Science Aspergillus flavus Fungus Microbial Sensitivity Tests Article Analytical Chemistry Aspergillus fumigatus chemistry.chemical_compound Drug Discovery Botany Benzopyrans Pyrroles Furans Candida Pharmacology Aspergillus biology Molecular Structure Organic Chemistry Aspergillus niger biology.organism_classification Complementary and alternative medicine chemistry Pyran Molecular Medicine |
| Zdroj: | Journal of natural products. 74(9) |
| ISSN: | 1520-6025 |
| Popis: | To date, natural products containing 2-benzyl-4H-pyran-4-one and 2-benzylpyridin-4(1H)-one substructures have been encountered in relatively few fungi outside of the black aspergilli clade. While exploring the occurrence of these compounds among Aspergillus spp., it was determined that the structures of the unusual furopyrrols tensidols A and B (5 and 6) and JBIR-86 and JBIR-87 (9 and 10) were incorrect and should be reassigned as 2-benzyl-4H-pyran-4-ones (7, 8, 11e, and 12, respectively). The origin of the unique N-phenyl groups in the 2-benzylpyridin-4(1H)-ones nygerones A and B (1 and 2) was also examined and it was established that N-phenylamides added to the culture medium were suitable substrates for generating these metabolites; however, this phenomenon remained limited to a single fungus in our collection (Aspergillus niger ATCC 1015). A variety of 2-benzyl-4H-pyran-4-ones and 2-benzylpyridin-4(1H)-ones were detected among the black aspergilli, but only pestalamide B (13) was found in all eleven of the tested strains. These metabolites, as well as a group of synthetic analogues demonstrated weak antifungal activity against several Candida strains, Aspergillus flavus, and Aspergillus fumigatus. |
| Databáze: | OpenAIRE |
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