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Khalil, Park, Kim, Akter, and Ahn: Anti-Helicobacter pylori Compounds from Polygonum cuspidatum
Original Article

Natural Product Sciences 2016;22(3):220-224.

Published online: 17 January 2016

DOI: https://doi.org/10.20307/nps.2016.22.3.220

Anti-Helicobacter pylori Compounds from Polygonum cuspidatum

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

College of Pharmacy and Research Institute of Pharmaceutical Sciences, Gyeongsang National University, Jinju 52828, Korea

∗Author for correspondence Mi-Jeong Ahn, College of Pharmacy and Research Institute of Pharmaceutical Sciences, Gyeongsang National University, Jinju 52828, Korea Tel: +82-55-772-2420; E-mail: amj5812@gnu.ac.kr

Both first authors contributed equally to this work.

Received 23 March 2016       Revised 26 April 2016       Accepted 2 May 2016

Copyright © 2016 The Korean Society of Pharmacognosy

This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/3.0) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

Anti-Helicobacter pylori activity guided fractionation led to the isolation of five anthraquinones, two stilbenes and one naphthoquinone from the EtOAc fraction of Polygonum cuspidatum, using silica gel column chromatography, Sephadex-LH20, MPLC and recrystallization. The chemical structures were identified to be physcion (1), emodin (2), anthraglycoside B (3), trans-resveratrol (4), anthraglycoside A (5), polydatin (6), 2-methoxy-6-acetyl-7-methyljuglone (7) and citreorosein (8) by UV,1 H-NMR,13 C-NMR and mass spectrometry. Anti-Helicobacter pylori activity including MIC values of each compound was evaluated. All of the isolates exhibited anti-H. pylori activity of which MIC values were lower than that of a positive control, quercetin. Compounds 2 and 7 showed potent growth inhibitory activity. Especially, a naphthoquinone, compound 7 displayed most potent antibacterial activity with MIC50 value of 0.30 µM and MIC90 value of 0.39 µM. Although anti-H. pylori activity of this plant was previously reported, this is the first report on that of compounds isolated from this species. From these findings, P. cuspidatum roots or its isolates may be useful for H. pylori infection and further study is needed to elucidate mechanism of action.

Keywords: Polygonum cuspidatum, Anti-Helicobacter pylori activity, Emodin, 2-Methoxy-6-acetyl-7-methyljuglone

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Fig. 1.
Chemical structures of compounds 1–8 isolated from the roots of Polygonum cuspidatum.
nps-22-220f1.tif
Table 1.
Anti-Helicobacter pylori activity of total extract and the fractions from P. cuspidatum
Sample DMSO Quercetin Total Ex. Hexane Fr. EtOAc Fr. BuOH Fr. Water Fr.
Clear zone (mm) – 11 16 19 21 12 10
Table 2.
13 C-NMR chemical shifts of compounds 1–8
C 1 2 3 4 5 6 7 8
1 165.2 164.9 162.2 139.7 161.2 139.8 179.1 161.9
2 121.3 120.9 124.6 104.7 124.7 103.2 161.0 121.2
3 148.5 148.7 147.3 159.0 147.6 159.4 109.6 153.2
4 124.5 124.6 119.7 102.2 119.8 105.2 190.3 117.5
5 108.2 109.4 109.1 159.0 107.0 158.8 158.1 109.3
6 162.5 161.9 165.5 104.7 165.2 107.7 130.5 165.0
7 106.8 108.4 108.9   108.7   143.5 108.4
8 166.6 166.3 161.7   162.2   121.6 166.3
9 190.8 190.6 186.7   187.0   136.7 190.0
10 182.1 181.8 182.7   182.4   112.4 181.9
4a 133.2 133.3 132.6   132.6     133.4
8a 110.3 109.3 113.4   115.0     109.5
9a 113.7 113.8 115.0   114.9     114.6
10a 135.3 135.5 136.9   136.8     135.6
a       126.1   125.7    
b       128.3   128.5    
1′       128.5   129.0    
2′       128.3   128.4    
3′       116.0   116.0    
4′       157.7   157.8    
5′       116.0   116.0    
6′       128.3   128.4    
1″     101.3   101.1 101.2    
2″     73.8   73.7 73.8    
3″     76.9   77.1 77.2    
4″     69.9   70.3 70.2    
5″     77.8   77.9 77.6    
6″     61.0   61.2 61.2    
6-OCH3 56.1       56.6      
3-CH3 22.2 22.0 21.9   21.9      
3-CH2 OH               62.5
2-OCH3             56.8  
6-COCH3             202.9  
6-COCH3             31.9  
7-CH3             20.0  
Table 3.
Anti-Helicobacter pylori activity of compounds 1–8
Samples Quercetin 1 2 3 4 5 6 7 8
MIC (µ M) 50 12.5 3.13 12.5 6.25 12.5 12.5 0.25 6.25
MIC50 (µ M) > 100 > 100 27.0 > 100 59.3 > 100 > 100 0.30 37.8
MIC90 (µ M) − − 48.8 − > 100 − − 0.39 100
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