Inhibition of electron transfer and uncoupling effects by emodin and emodinanthrone in Escherichia coli.
The anthraquinones emodin (1,3,delta-trihydroxy-6-methylanthraquinone) and emodinanthrone (1,3,8-trihydroxy-6-methylanthrone) inhibited respiration-driven solute transport at micromolar concentrations in membrane vesicles of Escherichia coli. This inhibition was enhanced by Ca ions. The inhibitory action on solute transport is caused by inhibition of electron flow in the respiratory chain, most likely at the level between ubiquinone and cytochrome b, and by dissipation of the proton motive force. The uncoupling action was confirmed by studies on the proton motive force in beef heart cytochrome oxidase proteoliposomes. These two effects on energy transduction in cytoplasmic membranes explain the antibiotic properties of emodin and emodinanthrone.
D000818:Animals; D000880:Anthraquinones / Q000494:pharmacology*; D001693:Biological Transport, Active / Q000187:drug effects; D002417:Cattle; D004579:Electron Transport / Q000187:drug effects; D003576:Electron Transport Complex IV / Q000378:metabolism; D004642:Emodin / Q000031:analogs & derivatives / Q000494:pharmacology*; D004926:Escherichia coli / Q000187:drug effects / Q000378:metabolism*; D066298:In Vitro Techniques; D008081:Liposomes / Q000378:metabolism; D009206:Myocardium / Q000378:metabolism; D011522:Protons; D014475:Uncoupling Agents
D000880:Anthraquinones; D008081:Liposomes; D011522:Protons; D014475:Uncoupling Agents; C049933:emodin anthrone; D003576:Electron Transport Complex IV; D004642:Emodin