Highly selective antibacterial activity of novel alkyl quinolone alkaloids from a Chinese herbal medicine, Gosyuyu (Wu-Chu-Yu), against Helicobacter pylori in vitro.
To elucidate the antibacterial activity of Gosyuyu, the crude extract from the fruit of Evodia rutaecarpa, a Chinese herbal medicine, has been fractionated chromatographically, and each fraction was assayed for antibacterial activity against Helicobacterpylori (H. pylori) in vitro. As the result, a single spot having marked antibacterial activity against H. pylori was obtained and the chemical structure was analyzed. The isolated compound was revealed to be a novel alkyl quinolone alkaloid based on the solubility, IR spectra, NMR analysis and mass spectrometric data after purification by TLC of silica. We compared the antimicrobial activity of this compound with that of other antimicrobial agents and examined susceptibility of various intestinal pathogens. As the result, the new quinolone compounds obtained from Gosyuyu extracts were found to be a mixture of two quinolone alkaloids, 1-methyl-2-[(Z)-8-tridecenyl]-4-(1H)-quinolone and 1-methyl-2-[(Z)-7-tridecenyl]-4-(1H)-quinolone (MW: 339), reported previously. The minimum inhibitory concentration (MIC) of these compounds against reference strains and clinically isolated H. pylori strains were less than 0.05 microg/ml, which was similar to the MIC of amoxicillin and clarithromycin that are used worldwide for the eradication of H. pylori, clinically. Furthermore, it was noted that the antimicrobial activity of these compounds was highly selective against H. pylori and almost non-active against other intestinal pathogens. The above results showed that these alkyl methyl quinolone (AM quinolones) alkaloids were useful for the eradication of H. pylori without affecting other intestinal flora.
Hamasaki
N
N
Department of Bacteriology, Osaka City University Medical School, Osaka, Japan.
Ishii
E
E
Tominaga
K
K
Tezuka
Y
Y
Nagaoka
T
T
Kadota
S
S
Kuroki
T
T
Yano
I
I
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D005591:Chemical Fractionation; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D032086:Evodia; D005638:Fruit / Q000737:chemistry; D016480:Helicobacter pylori / Q000187:drug effects* / Q000302:isolation & purification; D006801:Humans; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010936:Plant Extracts; D011804:Quinolines / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D015363:Quinolones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D012997:Solvents; D013276:Stomach Ulcer / Q000382:microbiology
D000470:Alkaloids; D000890:Anti-Infective Agents; D004365:Drugs, Chinese Herbal; C406544:Gosyuyu; D010936:Plant Extracts; D011804:Quinolines; D015363:Quinolones; D012997:Solvents