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

Mitchell Bacho, Vania Artigas, Tiare Araya-Contreras, Mauricio Bittner, Carlos A. Escobar, MAURICIO DANIEL FUENTEALBA CARRASCO, José Becerra, Victor Fajardo, Aurelio San-Martín

Resultado de la investigación: Contribución a una revistaArtículorevisión exhaustiva

Resumen

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.

Idioma originalInglés
PublicaciónNatural Product Research
DOI
EstadoAceptada/en prensa - 2021
Publicado de forma externa

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Profundice en los temas de investigación de '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'. En conjunto forman una huella única.

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