Neobulgarones Revisited: Anti and Syn Bianthrones from an Australian Mud Dauber Wasp Nest-Associated Fungus, Penicillium sp. CMB-MD22
| Autor: | Zeinab G. Khalil, Paul V. Bernhardt, Robert J. Capon, Ahmed H. Elbanna |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
Pharmacology
Antifungal biology 010405 organic chemistry medicine.drug_class Chemistry Stereochemistry Organic Chemistry Pharmaceutical Science Fungus biology.organism_classification 01 natural sciences 0104 chemical sciences Analytical Chemistry Mud dauber 010404 medicinal & biomolecular chemistry Complementary and alternative medicine Drug Discovery Penicillium Molecular networking medicine Thermal equilibration Molecular Medicine Chemical defense Nest (protein structural motif) |
| Zdroj: | Journal of Natural Products. 84:762-770 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/acs.jnatprod.0c01035 |
| Popis: | We report on the chemical analysis of a mud dauber wasp nest-associated fungus, Penicillium sp. CMB-MD22, leading to the discovery and structure elucidation of three known (1-3) and two new (4 and 5) anthrones, and a family of new and known bianthrones, neobulgarones 6-23. Detection and structure elucidation of 1-23 was supported by detailed spectroscopic analysis, as well as chemical (thermal) transformations, and global natural products social (GNPS) molecular networking. An empirical approach using HPLC retention times was effective at differentiating anti from syn bianthrone isomers, while a facile thermal equilibration was shown to favor anti over syn isomers. The neobulgarones 6-23 are natural products, and a crude extract rich in 6-23 exhibits selective antifungal activity against a co-isolated mud dauber wasp nest-associated fungus, suggestive of a possible ecological role as an antifungal chemical defense. |
| Databáze: | OpenAIRE |
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