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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.

natural product research

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