Spiroscytalin, a new tetramic acid and other metabolites of mixed biogenesis from Scytalidium cuboideum
| Autor: | Arlene A. Sy-Cordero, Nicholas H. Oberlies, Maria Elena Meza Avina, Cedric J. Pearce, Mitchell P. Croatt, Audrey F. Adcock, Mario Figueroa, Huzefa A. Raja, Mansukh C. Wani, David J. Kroll |
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| Rok vydání: | 2015 |
| Předmět: |
Circular dichroism
biology Chemistry Stereochemistry Organic Chemistry Absolute configuration Nuclear magnetic resonance spectroscopy Mass spectrometry biology.organism_classification Biochemistry Article Drug Discovery Candida albicans Cytotoxicity Antibacterial activity Two-dimensional nuclear magnetic resonance spectroscopy |
| Zdroj: | Tetrahedron. 71:8899-8904 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2015.09.073 |
| Popis: | Spiroscytalin (1), a new tetramic acid that possesses an uncommon spiro-ring fusion between a polyketide-derived octalin ring system and a 2,4-pyrrolidinedione, along with two known compounds, leporin B (2) and purpactin A (3), were isolated from a solid phase culture of the fungus Scytalidium cuboideum (MSX 68345). The molecular connectivity of 1–3 was determined using NMR spectroscopy and mass spectrometry. The relative configurations of 1 and 2 were determined by NOESY experiments. The absolute configuration of 1 was determined by electronic circular dichroism (ECD) via a combination of experimental measurements and computational calculations. While leporin B was known, it displayed activities that had not been reported previously, including cytotoxicity against three human tumor cell lines and antibacterial activity against Candida albicans and Staphylococcus aureus. |
| Databáze: | OpenAIRE |
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