Exiguaquinol: A Novel Pentacyclic Hydroquinone from Neopetrosia exigua that Inhibits Helicobacter pylori MurI
Organic Letters2008Vol. 10(12), pp. 2585–2588
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Priscila de Almeida Leone, Anthony R. Carroll, Leanne Towerzey, Gordon King, Bernadette M. McArdle, Günther Kern, Stewart L. Fisher, John N. A. Hooper, Ronald J. Quinn
Abstract
Bioassay-guided fractionation of the methanol extract of the Australian sponge Neopetrosia exigua led to the isolation of exiguaquinol (2), a new pentacyclic hydroquinone that inhibited Helicobacter pylori glutamate racemase (MurI) with an IC(50) of 4.4 microM. Its structure and relative configuration were assigned on the basis of spectroscopic data. Exiguaquinol (2), bearing a novel pentacyclic ring skeleton, is the first natural product to show inhibition of H. pylori MurI. Its protein-ligand modeling is also discussed.
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