Synthesis, characterisation, crystal structure and antimicrobial evaluation of novel 6-alkoxyergosta-4,6,8(14),22-tetraen-3-one derived from natural ergosta-5,7,22-trien-3β-ol
| Autor: | Vania Artigas, Carlos A. Escobar, Tiare Araya-Contreras, Mauricio Fuentealba, José Becerra, Mitchell Bacho, Aurelio San-Martín, Víctor Fajardo, Mauricio Bittner |
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| Rok vydání: | 2021 |
| Předmět: |
Staphylococcus aureus
Stereochemistry Plant Science Crystal structure 01 natural sciences Biochemistry Trientine Analytical Chemistry Acid catalysis chemistry.chemical_compound Spectroscopy Fourier Transform Infrared Escherichia coli Antibacterial agent Ergosterol biology 010405 organic chemistry Organic Chemistry Pseudomonas Antimicrobial biology.organism_classification 0104 chemical sciences Anti-Bacterial Agents 010404 medicinal & biomolecular chemistry chemistry Antibacterial activity Bacteria |
| Zdroj: | Natural product research. 37(1) |
| ISSN: | 1478-6427 |
| Popis: | In this study, we report a facile transformation starting from 5α-hydroxyergosta-7,22-dien-3,6-dione (1) to afford two novel compounds: 6-methoxyergosta-4,6,8(14),22-tetraen-3-one (2) and 6-ethoxyergosta-4,6,8(14),22-tetraen-3-one (3) using alcoholic acid catalysis. Their structures were elucidated using NMR experiments, FT-IR, MS and X-ray analysis. These compounds were evaluated for antibacterial activity using the disk and broth diffusion test. In those tests, compound 3 was found to be the most significant antibacterial agent. In general, compounds 1-3 showed inhibition zone in the range of 7.00-12.3 mm for S. aureus and S. mutans, meanwhile for Gram-negative bacteria E. coli and Pseudomonas sp. was found to be in the range of 7.00-8.00 mm. For the most active, compound 3, MIC was significantly lower than that reported for ergosterol, in a value of 160 µg/mL. Overall, these compounds were more active than their natural precursor. |
| Databáze: | OpenAIRE |
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