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KMID : 0043320190420060505
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Archives of Pharmacal Research
2019 Volume.42 No. 6 p.505 ~ p.511
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A new anti-Helicobacter pylori juglone from Reynoutria japonica
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Khalil Atif Ali Khan
Park Woo-Sung
Lee Jee-Hoon
Kim Hye-Jin
Akter Kazi-Marjahan
Goo Young-Min
Bae Ji-Yeong
Chun Man-Seog
Kim Jung-Hwan
Ahn Mi-Jeong
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Abstract
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A 70% ethanol extract from the root portion of Reynoutria japonica afforded one new and three known juglone derivatives, namely, 2-methoxy-6-acetyl-7-methyljuglone (1), 2-ethoxy-6-acetyl-7-methyljuglone (2), 2-methoxy-7-acetonyljuglone (3), and 3-acetyl-7-methoxy-2-methyljuglone (4) together with two phenolics (5 and 6), an anthraquinone (7), a stilbene (8) and a phthalide (9). Their structures were elucidated on the basis of comprehensive spectroscopic studies including IR, MS, and 1H, 13C, 2D NMR spectra. Compound 3 is a new compound in nature, and compounds 4?6 have been isolated for the first time from R. japonica. The isolates were evaluated for their antibacterial activity against three strains (43504, 51, and 26695) of Helicobacter pylori. The four isolated juglone derivatives (1?4) showed potent growth inhibitory activity. Among them, compounds 1?3 exhibited stronger inhibitory activity than those of the positive controls, juglone and metronidazole, for the three strains and that of another reference, clarithromycin, for the 43504 and 51 strains. Specifically, the new juglone compound 3 displayed the most potent antibacterial activity against all three strains, 43504, 51, and 26695, with MIC values of 0.06, 0.06 and 0.13 μM, respectively, and MIC50 values of 0.14, 0.11 and 0.15 μM, respectively.
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KEYWORD
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Reynoutria japonica, Juglone derivatives, Anti-Helicobacter pylori activity
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