Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지
DOI QR코드

DOI QR Code

Anti-Helicobacter pylori Activity of Compounds Isolated from Fraxinus mandshurica Bark

  • Akter, Kazi-Marjahan (College of Pharmacy and Research Institute of Pharmaceutical Sciences, Gyeongsang National University) ;
  • Kim, Hye-Jin (College of Pharmacy and Research Institute of Pharmaceutical Sciences, Gyeongsang National University) ;
  • Park, Woo Sung (College of Pharmacy and Research Institute of Pharmaceutical Sciences, Gyeongsang National University) ;
  • Khalil, Atif Ali Khan (College of Pharmacy and Research Institute of Pharmaceutical Sciences, Gyeongsang National University) ;
  • Ahn, Mi-Jeong (College of Pharmacy and Research Institute of Pharmaceutical Sciences, Gyeongsang National University)
  • Received : 2020.03.04
  • Accepted : 2020.03.26
  • Published : 2020.06.30
Download PDF
⟨ Previous Next ⟩

Abstract

Helicobacter pylori is a well-known pathogen that is responsible for gastric disorders. Overcoming of the antibiotic-resistance is a main barrier to treat H. pylori infection. In our search for anti-H. pylori compounds from natural resources, bioactivity-guided isolation on the ethyl acetate fraction of Fraxinus mandshurica bark that had shown anti-H. pylori activity gave twelve compounds (1 - 12) of six coumarins, three phenylethanoids, two secoiridoids, and a lignan using silica gel column chromatography, Sephadex-LH 20, and recrystallization. The chemical structures were identified by spectroscopic data analysis, including 1D, 2D NMR, and mass spectrometry. Among them, compounds 2, 10, and 11 showed moderate growth inhibitory activity against three strains of H. pylori, compared with positive controls of quercetin and metronidazole. Compounds 5, 6, 8, and 12 exhibited the inhibitory activity against strains 26695 or 43504. This is the first report on the anti-H. pylori activity of this plant and the isolated compounds.

Keywords

References

  1. Kobayashi, I.; Murakami, K.; Kato, M.; Kato, S.; Azuma, T.; Takahashi, S.; Uemura, N.; Katsuyama, T.; Fukuda, Y.; Haruma, K; Nasu, M; Fujioka, T. J. Clin. Microbiol. 2007, 45, 4006-4010. https://doi.org/10.1128/JCM.00740-07
  2. Gonzalez, A.; Salillas, S.; Velazquez-Campoy, A.; Angarica, V. E.; Fillat, A. F.; Sancho, J.; Lanas, A. Sci. Rep. 2019, 9, 11294. https://doi.org/10.1038/s41598-019-47746-9
  3. Kountouras, J.; Zavos, C.; Chatzopoulos, D. J. Cell. Mol. Med. 2005, 9, 196-207. https://doi.org/10.1111/j.1582-4934.2005.tb00349.x
  4. Francesco, V. D.; Giorgio, F.; Hassan, C.; Manes, G.; Vannella, L.; Panella, C.; Ierardi, E.; Zullo, A. J. Gastrointestin. Liver Dis. 2010, 19, 409-414.
  5. Khalil, A. A. K.; Park, W. S.; Kim, H. -J.; Akter, K. M.; Ahn, M. -J. Nat. Prod. Sci. 2016, 22, 220-224. https://doi.org/10.20307/nps.2016.22.3.220
  6. Park, W. S.; Bae, J. Y; Kim, H. J.; Kim, M. G.; Lee, W. K.; Kang, H. -L.; Baik, S. C.; Lim, K. M.; Lee, M. K.; Ahn, M. -J. Nat. Prod. Sci. 2015, 21, 49-53.
  7. Kong, D. M.; Shen, H. L.; Li, N. Afr. J. Biotechnol. 2013, 11, 120-125.
  8. Drenkhan, R.; Sander, H.; Hanso, M. Eur. J. For. Res. 2014, 133, 769-781. https://doi.org/10.1007/s10342-014-0811-9
  9. Chen, Y.; Xue, G.; Liu, F.; Gong, X. Bioengineered 2017, 8, 212-216. https://doi.org/10.1080/21655979.2016.1221023
  10. Tsukamoto, H.; Hisada, S.; Nishide, S. Chem. Pharm. Bull. 1984, 32, 4482-4489. https://doi.org/10.1248/cpb.32.4482
  11. Tsukamoto, H.; Hisada, S.; Nishibe, S,. Chem. Pharm. Bull. 1985, 33, 4069-4073. https://doi.org/10.1248/cpb.33.4069
  12. Kostova, I.; Iossifova, T. Fitoterapia 2007, 78, 85-106. https://doi.org/10.1016/j.fitote.2006.08.002
  13. Liao, J. C.; Wei, Z. X.; Zhao, C.; Ma, Z. P.; Cai, D. Z. Int. J. Mol. Med. 2018, 42, 1257-1264.
  14. Hadrich, F.; Garcia, M.; Maalej, A.; Moldes, M.; Isoda, H.; Feve, B.; Sayadi, S. Life Sci. 2016, 151, 167-173. https://doi.org/10.1016/j.lfs.2016.02.027
  15. Vandal, J.; Abou-Zaid, M. M.; Ferroni, G.; Leduc, L. G. Pharm. Biol. 2015, 53, 800-806. https://doi.org/10.3109/13880209.2014.942867
  16. Amin, M.; Anwar, F.; Naz, F.; Mehmood, T.; Saari, N. Molecules 2013, 18, 2135-2149. https://doi.org/10.3390/molecules18022135
  17. Yu, M.; Sun, A.; Zhang, Y.; Liu, R. J. chromatogr. Sci. 2014, 52, 1033-1037. https://doi.org/10.1093/chromsci/bmt153
  18. Takaya, Y.; Furukawa, T.; Miura, S.; Akutagawa, T.; Hotta, Y.; Ishikawa, N.; Niwa, M. J. Agric. Food Chem. 2007, 55, 75-79. https://doi.org/10.1021/jf062029d
  19. Lee, D. G.; Choi, J. S.; Yeon, S. W.; Cui, E. J.; Park, H. J.; Yoo, J. S.; Chung, I. S.; Beak, N. I. J. Korean Soc. Appl. Biol. Chem. 2010, 53, 371-374. https://doi.org/10.3839/jksabc.2010.057
  20. Murray, R. D. H.; Sutcliffe, M.; Hasegawa, M. Tetrahedron 1975, 31, 2966-2971. https://doi.org/10.1016/0040-4020(75)80320-6
  21. Jensen, S. R.; Nielsen, B. J. Phytochemistry 1976, 15, 221-223. https://doi.org/10.1016/S0031-9422(00)89092-5
  22. Casabuono, A. C.; Pomillo, A. B. Phytochemistry 1994, 35, 479-483. https://doi.org/10.1016/S0031-9422(00)94786-1
  23. Cavaca, L. A. S. New Synthetic Routes for the Valorization of Easily Accessible Bio-renewable Resources; University of Lisbon: Portugal, 2017, p 59.
  24. Kim, A. R.; Ko, H. J.; Chowdhury, M. A.; Chang, Y. S.; Woo, E. R. Arch. Pharm. Res. 2015, 38, 1059-1065. https://doi.org/10.1007/s12272-014-0543-x
  25. Keefover-Ring, K.; Holeski, L. M.; Bowers, M. D.; Clauss, A. D.; Lindroth, R. L. Phytochem. Lett. 2014, 10, 132-139. https://doi.org/10.1016/j.phytol.2014.08.016
  26. Kawase, M.; Tanaka, T.; Sohara, Y.; Tani, S.; Sakagami, H.; Hauer, H.; Chatterjee, S. S. In Vivo 2003, 17, 509-512.
  27. J ad hav, S . G.; Meshram, R . J.; Gond , D. S .; G acche, R. N. J. Pharm. Res. 2013, 7, 705-711. https://doi.org/10.1016/j.jopr.2013.09.002
  28. Temitope, O. L.; Kapil, K. S.; Brian, J. D.; Bolanle, A. A.; Gail, B. M. Curr. Bioact. Compd. 2012, 8, 266-276. https://doi.org/10.2174/157340712802762447
  29. Funatogawa, K.; Hayashi, S.; Shimomura, H.; Yoshida, T.; Hatano, T.; Ito, H.; Hirai, Y. Microbiol. Immunol. 2004, 48, 251-261. https://doi.org/10.1111/j.1348-0421.2004.tb03521.x
  30. Xiao, Z. P.; Ma, T. W.; Fu, W. C.; Peng, X. C.; Zhang, A. H.; Zhu, H. L. Eur. J. Med. Chem. 2010, 45, 5064-5070. https://doi.org/10.1016/j.ejmech.2010.08.015
  31. Sarfraz, I.; Rasul, A.; Jabeen, F.; Younis, T.; Zahoor, M. K.; Arshad, M.; Ali, M. Evid. Based Complement. Alternat. Med. 2017, 2017, 4269868. https://doi.org/10.1155/2017/4269868
  32. Amini, A.; Liu, M.; Ahmad, Z. Int. J. Biol. Macromol. 2017, 101, 153-164. https://doi.org/10.1016/j.ijbiomac.2017.03.087
  33. Liu, Y.; McKeever, L. C.; Malik, N. S. Front. Microbiol. 2017, 8, 113.
  34. Dong, Z.; Lu, X.; Tong, X.; Dong, Y.; Tang, L.; Liu, M. Molecules 2017, 22, 1466. https://doi.org/10.3390/molecules22091466
  35. Radev, R. J. Clin. Med. 2010, 3, 20-23.