Antibacterial Prenylated Acylphloroglucinols from Psorothamnus fremontii

• 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.

Ämnesord

NATURVETENSKAP  -- Kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences (hsv//eng)

Nyckelord

Psorothamnus fermontii

phenyl proponoids

Medicinsk kemi

Medical Chemistry

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