Wydział Chemii

Witold Gładkowski

Monika Siepka

Barbara Żarowska

Agata Białońska

Barbara Gawdzik

Mariusz Urbaniak

Czesław Wawrzeńczyk

2023

Molecules

28

3800/1-3800/18

10.3390/molecules28093800

Naukowa

Angielski

Artykuł

Four compounds with lactone moiety were synthesized from chalcone 1 in three- or four-step synthesis. γ-Bromo-δ-lactone 5 was the only product of bromolactonization of acid 4 whereas bromolactonization of ester 3, apart from lactone 5 also afforded its isomer 6 and two diastereoisomeric δ-hydroxy-γ-lactones 7 and 8. Lactone 8 was also obtained in 88% yield as a product of simultaneous dehalogenation and translactonization of γ-bromo-δ-lactone 5 by Penicillum frequentans AM 359. Chalcone-derived lactones 5–8 were subjected to the tests on antimicrobial activity and the results compared with activity of starting chalcone 1. Obtained lactones 5–8 in most cases limited the growth of tested bacterial and fungal strains. The highest activity was found for δ-hydroxy-γ-lactone 8 which completely inhibited the growth of Staphylococcus aureus, Fusarium graminearum, Aspergillus niger, and Alternaria sp. The introduction of lactone moiety into chalcone scaffold significantly improved antimicrobial activity of the compound: γ-bromo-δ-lactone 6 and δ-hydroxy-γ-lactone 8 were significantly stronger growth inhibitors of S. aureus and F. graminearum. In the case of the latter, a clear positive effect of the lactone function on the antifungal activity was also observed for γ-bromo-δ-lactone 5.

chalcone, bromolactonization, hydroxylactones, microbial dehalogenation, translactonization, antibacterial activity, antifungal activity

CC-BY

http://dx.doi.org/10.3390/molecules28093800

http://www.mdpi.com/journal/metals