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Archives of Pharmacal Research

, Volume 42, Issue 6, pp 505–511 | Cite as

A new anti-Helicobacter pylori juglone from Reynoutria japonica

  • Atif Ali Khan Khalil
  • Woo Sung Park
  • Jeehoon Lee
  • Hye-Jin Kim
  • Kazi-Marjahan Akter
  • Young-Min Goo
  • Ji-Yeong Bae
  • Man-Seog Chun
  • Jung-Hwan Kim
  • Mi-Jeong AhnEmail author
Research Article
  • 142 Downloads

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 46 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 (14) showed potent growth inhibitory activity. Among them, compounds 13 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.

Keywords

Reynoutria japonica Juglone derivatives Anti-Helicobacter pylori activity 

Notes

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.

Compliance with ethical standards

Conflict of interest

The authors declare no conflict of interest.

Supplementary material

12272_2019_1160_MOESM1_ESM.docx (22 mb)
Supplementary material 1 (DOCX 22521 kb)

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Copyright information

© The Pharmaceutical Society of Korea 2019

Authors and Affiliations

  • Atif Ali Khan Khalil
    • 1
  • Woo Sung Park
    • 1
  • Jeehoon Lee
    • 1
  • Hye-Jin Kim
    • 1
  • Kazi-Marjahan Akter
    • 1
  • Young-Min Goo
    • 2
  • Ji-Yeong Bae
    • 3
  • Man-Seog Chun
    • 4
  • Jung-Hwan Kim
    • 5
  • Mi-Jeong Ahn
    • 1
    Email author
  1. 1.College of Pharmacy and Research Institute of Pharmaceutical SciencesGyeongsang National UniversityJinjuSouth Korea
  2. 2.Gyeongnam Oriental Anti-aging InstituteSancheongSouth Korea
  3. 3.National Center for Natural Products Research, School of PharmacyUniversity of Mississippi, UniversityOxfordUSA
  4. 4.Korea Science Academy of KAISTBusanSouth Korea
  5. 5.Department of Pharmacology, School of MedicineInstitute of Health Sciences, Gyeongsang National UniversityJinjuSouth Korea

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