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A new anti-Helicobacter pylori juglone from Reynoutria japonica

Archives of Pharmacal Research volume 42, pages 505–511 (2019)Cite this article

Abstract

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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Acknowledgements

This study was carried out with the support of National Research Foundation of Korea (NRF) (NRF-2017R1A2B4008859), the Next-Generation BioGreen 21 Program (SSAC, Grant# PJ01318402), the Rural Development Administration, Republic of Korea and the Gyeongsang National University Fund for Professors on Sabbatical Leave, 2017.

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Author notes

  1. Atif Ali Khan Khalil, Woo Sung Park and Jeehoon Lee have contributed equally to this work.

Affiliations

  1. College of Pharmacy and Research Institute of Pharmaceutical Sciences, Gyeongsang National University, Jinju, Gyeongnam, 52828, South Korea

    Atif Ali Khan Khalil, Woo Sung Park, Jeehoon Lee, Hye-Jin Kim, Kazi-Marjahan Akter & Mi-Jeong Ahn

  2. Gyeongnam Oriental Anti-aging Institute, Sancheong, Gyeongnam, 52215, South Korea

    Young-Min Goo

  3. National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, Oxford, MS, 38677, USA

    Ji-Yeong Bae

  4. Korea Science Academy of KAIST, Busan, 47162, South Korea

    Man-Seog Chun

  5. Department of Pharmacology, School of Medicine, Institute of Health Sciences, Gyeongsang National University, Jinju, Gyeongnam, 52727, South Korea

    Jung-Hwan Kim

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  1. Atif Ali Khan Khalil
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  2. Woo Sung Park
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Correspondence to Mi-Jeong Ahn.

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Khalil, A.A.K., Park, W.S., Lee, J. et al. A new anti-Helicobacter pylori juglone from Reynoutria japonica. Arch. Pharm. Res. 42, 505–511 (2019). https://doi.org/10.1007/s12272-019-01160-x

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  • DOI: https://doi.org/10.1007/s12272-019-01160-x

Keywords

  • Reynoutria japonica
  • Juglone derivatives
  • Anti-Helicobacter pylori activity