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Antibacterial Prenylated Acylphloroglucinols from Psorothamnus fremontii
- Publication Year :
- 2015
-
Abstract
- Psorothatins A-C (1-3), three antibacterial prenylated acylphloroglucinol derivatives, were isolated from the native American plant Psorothamnus fremontii. They feature an unusual alpha,beta-epoxyketone functionality and a beta-hydroxy-alpha,beta-unsaturated ketone structural moiety. The latter forms a pseudo-six-membered heterocyclic ring due to strong intramolecular hydrogen bonding, as indicated by the long-range proton-carbon correlations in the NMR experiments. Psorothatin C (3) was the most active compound against methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus faecium, with IC50 values in the range 1.4-8.8 mu g/mL. The first total synthesis of 3 described herein permits future access to structural analogues with potentially improved antibacterial activities.
Details
- Database :
- OAIster
- Notes :
- English
- Publication Type :
- Electronic Resource
- Accession number :
- edsoai.on1233980340
- Document Type :
- Electronic Resource
- Full Text :
- https://doi.org/10.1021.acs.jnatprod.5b00721