Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
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Flavonoid Glycosides as Acetylcholinesterase Inhibitors from the Whole Plants of Persicaria thunbergii

  • Kim, Se Young (College of Pharmacy, Kangwon National University) ;
  • Park, Jun Young (College of Pharmacy, Kangwon National University) ;
  • Park, Pil Sung (College of Pharmacy, Kangwon National University) ;
  • Bang, Sang Ho (College of Pharmacy, Kangwon National University) ;
  • Lee, Kyung Min (College of Pharmacy, Kangwon National University) ;
  • Lee, Yu Ra (College of Pharmacy, Kangwon National University) ;
  • Jang, Yong Hyun (College of Pharmacy, Kangwon National University) ;
  • Kim, Myong Jo (Oriental Bio-Herb Research Institute, Kangwon National University) ;
  • Chun, Wanjoo (College of Medicine, Kangwon National University) ;
  • Heo, Moon Young (College of Pharmacy, Kangwon National University) ;
  • Kwon, Yongsoo (College of Pharmacy, Kangwon National University)
  • Received : 2014.06.03
  • Accepted : 2014.06.24
  • Published : 2014.09.30
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Abstract

The n-BuOH soluble fraction of the whole plant of Persicaria thungergii showed acetylcholinesterase inhibitory activity. Four flavonoid glycosides and a flavonoid were isolated from this fraction, and identified as quercitrin (1), luteolin-4'-O-${\beta}$-D-glucopyranoside (2), quercetin (3), quercetin-3-O-glucuronide (4), and isorahmnetin-3-O-glucuronid (5), by chromatographed and spectral data, respectively. All isolated compounds were showed acetylcholinesterase inhibitory activity, with $IC_{50}$ values of 243.1, 10.5, 39.1, 8.2 and $23.2{\mu}M$, respectively.

Keywords

References

  1. Prince, M.; Bryce, R.; Albanese, E.; Wimo, A.; Ribeiro W.; Ferri, C. P. Alzheimer Dementia, 2013, 9, 63-75. https://doi.org/10.1016/j.jalz.2012.11.007
  2. Roberson, R. M.; Harrell, E. L. Brain Res. Rev., 1997, 25, 50-69. https://doi.org/10.1016/S0165-0173(97)00016-7
  3. Mattson, P. M. J. Neurovirol. 2002, 8, 539-550. https://doi.org/10.1080/13550280290100978
  4. Akiyama, H.; Barger, S.; Barnum, S.; Bradt, B.; Bauer, J.; Cole, M. G; Cooter, R. N.; Eikelenboom, P.; Emmerling, M.; Fiebich, L. B.; Finch, E. C.; Frautschy, S.; Griffin, W. S. T.; Hampel, H.; Hull, M.; Landreth, G.; Lue, L. F.; Mrak, R.; Mackenzie, R. E.; McGeer, L. P.; O'Manion, M. K.; Pachter, J.; Painetti, G.; Plata-Salman, C.; Rogers, J.; Rydel, R.; Shen, Y.; Streit, W.; Strohmeyer, R.; Tooyoma, I.; Muiswinkel, V. L. F.; Veerhuis, R.; Walker, D.; Webster, S.; Wegrzyniak, B.; Wenk, G.; Wyss-Coray, T. Neurobiol. Aging, 2000, 21, 383-421. https://doi.org/10.1016/S0197-4580(00)00124-X
  5. Bartus, R. T.; Dean III, R. L.; Beer, B.; Lippa, A. S. Science, 1982, 217, 408-416. https://doi.org/10.1126/science.7046051
  6. Coyle, J. T.; Price, D. L.; DeLong, M. R. Science, 1983, 219, 1184-1190. https://doi.org/10.1126/science.6338589
  7. Mukherjee, P. K.; Kumar, V.; Mal, M.; Houhton, P. J. Phytomedicine, 2007, 14, 289-300. https://doi.org/10.1016/j.phymed.2007.02.002
  8. Houghton, P. J.; Ren, Y.; Howes, M. J. Nat. Prod. Rep. 2006, 23, 181-199. https://doi.org/10.1039/b508966m
  9. Anad, P.; Singh, B. Arch. Pharm. Res., 2013, 36, 375-399. https://doi.org/10.1007/s12272-013-0036-3
  10. Lee, W. T. Colored standard illustrations of Korean plants, Academy press: Seoul, 1996; p 79.
  11. Editorial Committee of Zhong Hua Ben Cao of State Administration of Traditional Chinese Medicine of People's Republic of China, Zhong Hua Ben Cao, Shanghai Science and Technology Press, Shanghai, 1999, Vol. 2, p 696.
  12. Lee, K. T.; Ku, C. H.; Eun, J. S.; Shin, T. Y.; Lim, J. P.; Eom, D. O.; Zee, O. P.; Kim, D. K. Yakhak Hoeji, 2001, 45, 611-616.
  13. Lee, K. S.; Kwon, B. M.; Baek, N. I.; Kim, S. H.; Lee, J. H.; Park, H. W.; Kim, J. S.; Moon, M. K.; Kim, D. K. Nat. Prod. Sci. 2006, 12, 214-216.
  14. Oh, M. H.; Kwon, B. M.; Baek, N. I.; Kim, S. H.; Chung, I. S.; Park, M. H.; Park. H. W.; Lee, J. H.; Park, H. W.; Kim, E. J.; Kim, D. K. Arch. Pharm. Res. 2005, 28, 169-171. https://doi.org/10.1007/BF02977709
  15. Ellman, L. G.; Courtney, K. D.; Andres Jr., V.; Featherstone, R. M. Biochem. Pharmacol. 1961, 7, 88-95. https://doi.org/10.1016/0006-2952(61)90145-9
  16. Dall'Acqua, S.; Maggi, F.; Minesso, P.; Salvagno, M.; Papa, F.; Vittor, S.; Innocenti, G. Fitoterapia, 2010, 81, 1208-1212. https://doi.org/10.1016/j.fitote.2010.08.003
  17. Kim, G. B.; Shin, K. S.; Kim, C. M.; Kwon, Y. Kor. J. Pharmacogn. 2006, 37, 177-183.
  18. Lee, M. H.; Son, Y. K.; Han, Y. N. Arch. Pharm. Res. 2002, 25, 842-850. https://doi.org/10.1007/BF02977002
  19. Jin, W.; Na, M. K.; An, R. B.; Lee, H. Y.; Bae, K.; Kang, S. S. Nat. Prod. Sci. 2002, 8, 129-132.
  20. Mabry, T. J.; Thomas, M. B. The systematic identification of Flavonoids, Springer-Verlag: New York, 1970; p 268.
  21. Agrawal P. K. Carbone-13 NMR of Flavonoids. Elsevier, Amsterdam, 1989, pp. 292-293.
  22. Mohle, B.; Heller, W.; Wellmann, E. Phytochemistry, 1985, 24, 465-467. https://doi.org/10.1016/S0031-9422(00)80748-7
  23. Granica, S.; Czerwinska, M. E.; Zyzynska-Granica, B.; Kiss, A. K. Fitotherapia, 2013, 91, 180-188. https://doi.org/10.1016/j.fitote.2013.08.026
  24. Kim, D. K. Arch. Pharm. Res. 2002, 25, 817-819. https://doi.org/10.1007/BF02976997
  25. Lopez, S.; Bastida, J.; Viladomat, F.; Codina, C. Life Sci. 2002, 71, 2521-2529. https://doi.org/10.1016/S0024-3205(02)02034-9
  26. Tang, X. C.; Kindel, G. H.; Kozikowski, A. P.; Hanin, I. J. Ethnopharamcol. 1994, 44, 147-155. https://doi.org/10.1016/0378-8741(94)01182-6
  27. Kim, D. K.; Lim, J. P.; Yang, J. H.; Yang, J. H..; Eom, D. O.; Eun, J. S.; Leem, K. H. Arch. Pharm. Res. 2002, 25, 856-859. https://doi.org/10.1007/BF02977004
  28. Kang, S. Y.; Lee, K. Y.; Sung, S. H.; Park, M. J.; Kim, Y. C. J. Nat. Prod. 2001, 64, 683-685. https://doi.org/10.1021/np000441w
  29. Tareq, M.; Khan H.; Orhan, I.; Senol, F. S.; Kartal, M.; Sener, B.; Dvorska, M.; Smejkal, K.; Slapetova, T. Chemic-Biological Interactions, 2009, 181, 383-389. https://doi.org/10.1016/j.cbi.2009.06.024
  30. Dohi, S.; Terasaki, M.; Makino, M. J. Agric. Food Chem. 2009, 57, 4313-4318. https://doi.org/10.1021/jf804013j
  31. Sim, J. Y.; Kim, M. A.; Kim, M. J.; Chun, W.; Kwon, Y. Nat. Prod. Sci. 2013, 20, 13-16.
  32. Uriarte-Pueyo, I.; Calvo, M. I. Curr. Med. Chem., 2011, 18, 5289-5302. https://doi.org/10.2174/092986711798184325
  33. Fan, P.; Hay, A. E.; Marston, A.; Hostettmann, K. Pharm. Biol. 2008, 46, 596-601. https://doi.org/10.1080/13880200802179592
  34. Kim, J. Y.; Lee, W. S.; Kim, Y. S.; Curtis-Long, M. J.; Lee, B. W.; Ryu, Y. B.; Park, K. H. J. Agric. Food Chem. 2011, 59, 4589-4596. https://doi.org/10.1021/jf200423g
  35. Hernadez, M. F.; Fale, P. L. V.; Araujo, M. E. M.; Serralheiro, M. L. M. Food Chem. 2010, 120, 1076-1082. https://doi.org/10.1016/j.foodchem.2009.11.055
  36. Katalinic, M.; Rusak, G.; Barovic, D. J.; Sinko, G.; Jelic, D.; Antolovic, R.; Kovarik, Z. Eur. J. Med. Chem. 2010, 45, 186-192. https://doi.org/10.1016/j.ejmech.2009.09.041
  37. Pohanka, M. Expert Opin. Ther. Patents, 2012, 22, 871-886. https://doi.org/10.1517/13543776.2012.701620
  38. Oinonen, P. P.; Jokela, K. J.; Hatakka, I. A.; Vuorela, M. P. Fitoterapia, 2006, 77, 429-434. https://doi.org/10.1016/j.fitote.2006.05.002