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.
MeSH terms
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Amino Acid Isomerases / antagonists & inhibitors*
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Animals
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / isolation & purification*
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Anti-Bacterial Agents / pharmacology*
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Crystallography, X-Ray
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Helicobacter pylori / drug effects*
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Helicobacter pylori / enzymology*
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Hydroquinones / chemistry
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Hydroquinones / isolation & purification*
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Hydroquinones / pharmacology*
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Ligands
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Molecular Structure
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Porifera / chemistry*
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Protein Conformation
Substances
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Anti-Bacterial Agents
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Hydroquinones
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Ligands
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exiguaquinol
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Amino Acid Isomerases
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glutamate racemase