Synthesis and antibacterial activity of hydrolytically stable (-)-epicatechin gallate analogues for the modulation of beta-lactam resistance in Staphylococcus aureus.
Hydrolytically more stable analogues of (-)-epicatechin gallate (ECg) have been synthesised from ECg where an amine or amide function has been substituted for the ester linkage that joins the C-ring with the galloyl D-ring. Sub-inhibitory concentrations (25 mg/L) of the amide analogue 7, possessing the natural C-3 stereochemistry, were able to reduce the resistance to oxacillin of three strains of methicillin resistant Staphylococcus aureus (BB 568, EMRSA-15 and EMRSA-16) comparable to levels achieved with ECg.
Anderson
James C
JC
School of Chemistry, University of Nottingham, Nottingham NG7 2RD, UK. j.anderson@nottingham.ac.uk
Headley
Catherine
C
Stapleton
Paul D
PD
Taylor
Peter W
PW
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002392:Catechin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006868:Hydrolysis; D008826:Microbial Sensitivity Tests
D000900:Anti-Bacterial Agents; D002392:Catechin; C062669:epicatechin gallate