A new anti- Helicobacter pylori juglone from Reynoutria japonica
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Online ISSN 1976-3786 Print ISSN 0253-6269
RESEARCH ARTICLE
A new anti-Helicobacter pylori juglone from Reynoutria japonica Atif Ali Khan Khalil1 • Woo Sung Park1 • Jeehoon Lee1 • Hye-Jin Kim1 • Kazi-Marjahan Akter1 • Young-Min Goo2 • Ji-Yeong Bae3 • Man-Seog Chun4 Jung-Hwan Kim5 • Mi-Jeong Ahn1
•
Received: 22 January 2019 / Accepted: 25 April 2019 / Published online: 9 May 2019 Ó The Pharmaceutical Society of Korea 2019
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-7methyljuglone (1), 2-ethoxy-6-acetyl-7-methyljuglone (2), 2-methoxy-7-acetonyljuglone (3), and 3-acetyl-7-methoxy2-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, 13 C, 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
Atif Ali Khan Khalil, Woo Sung Park and Jeehoon Lee have contributed equally to this work.
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s12272-019-01160-x) contains supplementary material, which is available to authorized users. & Mi-Jeong Ahn [email protected] 1
College of Pharmacy and Research Institute of Pharmaceutical Sciences, Gyeongsang National University, Jinju, Gyeongnam 52828, South Korea
2
Gyeongnam Oriental Anti-aging Institute, Sancheong, Gyeongnam 52215, South Korea
3
National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, Oxford, MS 38677, USA
4
Korea Science Academy of KAIST, Busan 47162, South Korea
5
Department of Pharmacology, School of Medicine, Institute of Health Sciences, Gyeongsang National University, Jinju, Gyeongnam 52727, South Korea
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 lM, respectively, and MIC50 values of 0.14, 0.11 and 0.15 lM, respectively. Keywords Reynoutria japonica Juglone derivatives Anti-Helicobacter pylori activity
Introduction The medicinal plant Reynoutria japonica Houtt. (Polygonum cuspidatum Siebold & Zucc.) is a Japanese knotweed which belongs to the plant family Polygonaceae. It is a native perennial herb that is 1–2 m tall and is largely available in South Korea, Japan, China, North America and Europe (Shan et al. 2008; Patocka et al. 2017
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