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Antibacterial Prenylated Acylphloroglucinols from Psorothamnus fremontii
- Yu, Qian, Ravu, Ranga Rao, Xu, Qiong-Ming, Ganji, Suresh, Jacob, Melissa R., Khan, Shabana I., Yu, Bo-Yang, Li, Xing-Cong
- Journal of natural products 2015 v.78 no.11 pp. 2748-2753
- Enterococcus faecium, Psorothamnus, Staphylococcus aureus, active ingredients, antibacterial properties, antibiotic resistance, hydrogen bonding, indigenous species, methicillin, nuclear magnetic resonance spectroscopy, structure-activity relationships, synthesis
- Psorothatins A−C (1−3), three antibacterial prenylated acylphloroglucinol derivatives, were isolated from the native American plant Psorothamnus fremontii. They feature an unusual α,β-epoxyketone functionality and a β-hydroxy-α,β-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 IC(50) values in the range 1.4−8.8 μg/mL. The first total synthesis of 3 described herein permits future access to structural analogues with potentially improved antibacterial activities.