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
- 1Universidad de Chile
- 2Pontificia Universidad Catolica de Valparaiso
- 3Universidad Andres Bello
- 4Universidad Autonoma de Chile
- 5Universidad de Concepcion
- 6
Journal
Natural Product Research
ISSN
1478-6419
1478-6427
Open Access
closed
Volume
37
Start page
16
End page
23
In this study, we report a facile transformation starting from 5 alpha-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 mu g/mL. Overall, these compounds were more active than their natural precursor.