Polyphenols based on isoflavones as inhibitors of Helicobacter pylori urease.
Twenty polyphenols were synthesized and evaluated for their effect on Helicobacter pylori urease. Among these compounds, 4-(p-hydroxyphenethyl)pyrogallol (15) (IC(50)=0.03 mM) and 7,8,4'-trihydroxyisoflavone (19) (IC(50)=0.14 mM) showed potent inhibitory activities, and inhibited Helicobacter pylori urease in a time-dependent manner. The structure-activity relationship of these polyphenols revealed: the two ortho hydroxyl groups were essential for inhibitory activity of polyphenol. When the C-ring of isoflavone was broken, the inhibitory activity markedly decreased. As for deoxybenzoin, the carboxyl group was clearly detrimental.
Xiao
Zhu-Ping
ZP
Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, PR China.
Shi
Da-Hua
DH
Li
Huan-Qiu
HQ
Zhang
Li-Na
LN
Xu
Chen
C
Zhu
Hai-Liang
HL
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001426:Bacterial Proteins / Q000037:antagonists & inhibitors*; D005419:Flavonoids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D016480:Helicobacter pylori / Q000187:drug effects* / Q000201:enzymology; D007529:Isoflavones / Q000737:chemistry; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D059808:Polyphenols; D013329:Structure-Activity Relationship; D014510:Urease / Q000037:antagonists & inhibitors*
D000900:Anti-Bacterial Agents; D001426:Bacterial Proteins; D005419:Flavonoids; D007529:Isoflavones; D010636:Phenols; D059808:Polyphenols; D014510:Urease