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. Issue 1 (2nd January 2023)

• Record Type: Journal Article
• Authors: Bacho, Mitchell; Artigas, Vania; Araya-Contreras, Tiare; Bittner, Mauricio; Escobar, Carlos A.; Fuentealba, Mauricio; Becerra, José; Fajardo, Victor; San-Martín, Aurelio
• Is Part Of: Natural product research. Volume 37:Issue 1(2023)
• Page Start: 16
• Page End: 23
• Publication Date: 2023-01-02
• Subjects: X-ray analysis -- sterol derivatisation -- antimicrobial activity -- alcoholic acid catalysis; Natural products -- Periodicals; Natural products -- Research -- Periodicals; Biological Factors -- Periodicals; Biological Products -- Periodicals; 547
• DOI: 10.1080/14786419.2021.1946534
• Languages: English
• ISSNs: 1478-6419

Abstract

Abstract: 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. Graphical Abstract: UF0001