title: Antibacterial Prenylated Acylphloroglucinols from Psorothamnus fremontii.
abstract: 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 IC50 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.
authors.affiliation: Jiangsu Key Laboratory of TCM Evaluation and Translational Research, Department of Complex Prescription of TCM, China Pharmaceutical University , Nanjing, 211198, People's Republic of China.
authors.forename: Qian
authors.initials: Q
authors.lastname: Yu
authors.forename: Ranga Rao
authors.initials: RR
authors.lastname: Ravu
authors.forename: Qiong-Ming
authors.initials: QM
authors.lastname: Xu
authors.forename: Suresh
authors.initials: S
authors.lastname: Ganji
authors.forename: Melissa R
authors.initials: MR
authors.lastname: Jacob
authors.forename: Shabana I
authors.initials: SI
authors.lastname: Khan
authors.affiliation: Jiangsu Key Laboratory of TCM Evaluation and Translational Research, Department of Complex Prescription of TCM, China Pharmaceutical University , Nanjing, 211198, People's Republic of China.
authors.forename: Bo-Yang
authors.initials: BY
authors.lastname: Yu
authors.forename: Xing-Cong
authors.initials: XC
authors.lastname: Li
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D016984:Enterococcus faecium / Q000187:drug effects; D007887:Fabaceae / Q000737:chemistry*; D006801:Humans; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010696:Phloroglucinol / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D054876:Prenylation; D013329:Structure-Activity Relationship; D014589:Utah; D014640:Vancomycin / Q000494:pharmacology
chemical_list: D000900:Anti-Bacterial Agents; D014640:Vancomycin; D010696:Phloroglucinol