1. Exiguaquinol: a novel pentacyclic hydroquinone from Neopetrosia exigua that inhibits Helicobacter pylori MurI.
- Author
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de Almeida Leone P, Carroll AR, Towerzey L, King G, McArdle BM, Kern G, Fisher S, Hooper JN, and Quinn RJ
- Subjects
- Animals, Anti-Bacterial Agents chemistry, Crystallography, X-Ray, Hydroquinones chemistry, Ligands, Molecular Structure, Protein Conformation, Amino Acid Isomerases antagonists & inhibitors, Anti-Bacterial Agents isolation & purification, Anti-Bacterial Agents pharmacology, Helicobacter pylori drug effects, Helicobacter pylori enzymology, Hydroquinones isolation & purification, Hydroquinones pharmacology, Porifera chemistry
- 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.
- Published
- 2008
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