Exiguaquinol: a novel pentacyclic hydroquinone from Neopetrosia exigua that inhibits Helicobacter pylori MurI.
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.
de Almeida Leone
Priscila
P
Eskitis Institute, Griffith University, Brisbane, QLD, Australia.
Carroll
Anthony R
AR
Towerzey
Leanne
L
King
Gordon
G
McArdle
Bernadette M
BM
Kern
Gunther
G
Fisher
Stewart
S
Hooper
John N A
JN
Quinn
Ronald J
RJ
D000591:Amino Acid Isomerases / Q000037:antagonists & inhibitors*; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D016480:Helicobacter pylori / Q000187:drug effects* / Q000201:enzymology*; D006873:Hydroquinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D008024:Ligands; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D011487:Protein Conformation
D000900:Anti-Bacterial Agents; D006873:Hydroquinones; D008024:Ligands; C530467:exiguaquinol; D000591:Amino Acid Isomerases; C062292:glutamate racemase