Cholinesterase Inhibitory Activities of Alkaloids from Corydalis Tuber

  • Hung, Tran Manh (Faculty of Chemistry, University of Natural Science, National University Hochiminh city) ;
  • Thuong, Phuong Thien (National Institute of Medicinal Materials) ;
  • Nhan, Nguyen Trung (Faculty of Chemistry, University of Natural Science, National University Hochiminh city) ;
  • Mai, Nguyen Thi Thanh (Faculty of Chemistry, University of Natural Science, National University Hochiminh city) ;
  • Quan, Tran Le (Faculty of Chemistry, University of Natural Science, National University Hochiminh city) ;
  • Choi, Jae-Sue (Faculty of Food Science and Biotechnolgy, Pukyoung National University) ;
  • Woo, Mi-Hee (College of Pharmacy, Catholic University of Daegu) ;
  • Min, Byung-Sun (College of Pharmacy, Catholic University of Daegu) ;
  • Bae, Ki-Hwan (College of Pharmacy, Chungnam National University)
  • Received : 2011.04.16
  • Accepted : 2011.05.10
  • Published : 2011.06.30

Abstract

Several isoquinoline alkaloids (1 - 18), which have basic chemical structures as protoberberine and aporphine skeletones, were evaluated for their inhibitory activities on AChE and BuChE. Among them, compounds 3, 4, 6, 8 and 12 showed the potent AchE activity with the $IC_{50}$ values ranging from $10.2{\pm}0.5\;{\mu}M$ to $24.5{\pm}1.6\;{\mu}M$, meanwhile, compound 14 - 17 exhibited strong inhibitory activity with $IC_{50}$ values from $2.1{\pm}0.2$ to $5.5{\pm}0.3\;{\mu}M$. Compounds 14 - 17 exhibited selective inhibition for AChE compared with BuChE. The isoquinoline alkaloid possesses aromatic methylenedioxy groups and quaternary nitrogen atoms are crucial for the anti-cholinesterase inhibitory activity.

Keywords

References

  1. Adsersen, A., Kjolbye, A., Dall, O., and Joger A.K., Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Corydalis cava Schweigg. & Kort. J. Ethnopharmacol. 113, 179-182 (2007). https://doi.org/10.1016/j.jep.2007.05.006
  2. Becker, R., Giacobini, E., Elble, R., McIlhany, M., and Sherman, K., Potential pharmacotherapy of Alzheimer disease. A comparison of various forms of physostigmine administration. Acta Neurologica Scandinavica. Supplementum 116, 19-32 (1988).
  3. Ellman, G.L., Courtney, K.D., Andres Jr, V., and Featherstone, R.M., A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 7, 88-90 (1961). https://doi.org/10.1016/0006-2952(61)90145-9
  4. Giacobini, E., The cholinergic system in Alzheimer disease. Prog. Brain Res. 84, 321-332 (1990).
  5. Giacobini, E., Cholinesterase inhibitors: from the calabar bean to Alzheimer therapy. eds. by Giacobini, E., Dunitz, M., Thonex-Geneva, pp. 181-226 (2000).
  6. Halbsguth, C., Meissner, O., and Haberlein H., Positive cooperation of protoberberine type 2 alkaloids from Corydalis cava on the GABA(A) binding site. Planta Med. 69, 305-309 (2003). https://doi.org/10.1055/s-2003-38869
  7. Houghton, P.J., Ren, Y., and Howes, M.J., Acetylcholinesterase inhibitors from plants and fungi. Nat. Prod. Rep. 23, 181-199 (2006). https://doi.org/10.1039/b508966m
  8. Hung, T.M., Na, M., Dat, N.T., Ngoc, T.M., Youn, U., Kim, H.J., Min, B.S., Lee, J., and Bae, K., Cholinesterase inhibitory and anti-amnesic activity of alkaloids from Corydalis turtschaninovii. J. Ethnopharmacol. 119, 74-80 (2008). https://doi.org/10.1016/j.jep.2008.05.041
  9. Hung, T.M., Na, M., Min, B.S., Zhang, X., Lee, I., Ngoc, T.M., Thuong, P.T., Sok, D.E., and Bae, K., Protective effect of magnoflorine isolated from coptidis rhizoma on $Cu2^+$-induced oxidation of human low density lipoprotein. Planta Med. 73, 1281-1284 (2007). https://doi.org/10.1055/s-2007-981615
  10. Hwang, S.Y., Chang, Y.P., Byun, S.J., Jeon, M.H., and Kim, Y.C., An acetylcholinesterase inhibitor isolated from Corydalis tuber and its mode of action. Kor. J. Pharm. 27, 91-95 (1996).
  11. Ito, C., Mizuno, T., Wu, T.S., and Furukawa, H., Alkaloids from Corydalis. Phytochemistry 29, 2044-2045 (1990). https://doi.org/10.1016/0031-9422(90)85070-V
  12. Kamigauchi, M. and Iwasa, K., Corydalis spp. VI: In vitro culture and the biotransformation of protoberberines. Vol. 26., eds. by Bajaj, Y.P.S., Springer-Verlag, Berlin Heidelberg, pp. 93-105 (1994).
  13. Kim, D.K., Inhibitory effect of corynoline isolated from the aerial parts of Corydalis incisa on the acetylcholinesterase. Arch. Pharm. Res. 25, 817-819 (2002). https://doi.org/10.1007/BF02976997
  14. Kim, S.R., Hwang, S.Y., Jang, Y.P., Park, M.J., Markelonis, G.J., and Oh, T.H., Protopine from Corydalis ternata has anticholinesterase and antiamnesic activities. Planta Med. 65, 218-221 (1999). https://doi.org/10.1055/s-1999-13983
  15. Kim, D.K., Lee, K.T., Baek, N.I., Kim, S.H., Park, H.W., Lim, J.P., Shin, T.Y., Eom, D.O., Yang, J.H., and Eun, J.S., Acetylcholinesterase inhibitors from the aerial parts of Corydalis speciosa. Arch. Pharm. Res. 27, 1127-1131 (2004). https://doi.org/10.1007/BF02975117
  16. Kiryakov, H.G., Iskrenova, E., Daskalova, E., Kuzmanov, B., and Evstatieva, L., Alkaloids of Corydalis slivenensis. Planta Med. 44, 168-170 (1982). https://doi.org/10.1055/s-2007-971432
  17. Lee, Y.L., Sagare, A.P., Lee, C.Y., Feng, H.T., Ko, Y.C, Shaw, J.F., and Tsay, H.S., Formation of protoberberine-type alkaloids by the tubers of somatic embryo-derived plants of Corydalis yanhusuo. Planta Med. 67, 839-842 (2001). https://doi.org/10.1055/s-2001-18853
  18. Miyazawa, M., Yoshio, K., Ishikawa, Y., and Kameoka. H., Insecticidal alkaloids from Corydalis bulbosa against Drosophila melanogaster. J. Agric. Food Chem. 46, 1914-1919 (1998). https://doi.org/10.1021/jf9701897
  19. Oh, M.H., Houghton, P.J., Whang, W.K., and Cho, J.H., Screening of Korean herbal medicines used to improve cognitive function for anticholinesterase activity. Phytomedicine 11, 544-548 (2004). https://doi.org/10.1016/j.phymed.2004.03.001
  20. Tang, W. and Eisenbrand, G., Corydalis turtschaninovii Bess. f. yanhusuo Y.H. Chou et C.C. Hsu, Chinese drugs of plant origin, chemistry, pharmacology, and use in traditional and modern medicine, eds. by Tang, W., Eisenbrand, G., Springer-Verlag, Berlin Heidelberg, pp. 377- 393 (1992).
  21. Thomsen, T., Zendeh, B., Fischer, J.P., and Kewitz, H. In vitro effects of various cholinesterase inhibitors on acetyl- and butyrylcholinesterase of healthy volunteers. Biochem. Pharmacol. 41, 139-141 (1991). https://doi.org/10.1016/0006-2952(91)90022-W
  22. Ulrichova, J., Walterova, D., Preininger, V., Slavk, J., Lenfeld, J., and Cushman M., Inhibition of acetylcholinesterase activity by some isoquinoline alkaloids. Planta Med. 48, 111-115 (1983). https://doi.org/10.1055/s-2007-969901
  23. Xu, X.H., Yu, G.D., and Wang, Z.T., Resource inv estigation and quality evaluation on wild Corydalis yanhusuo. Zhongguo Zhong Yao Za Zhi 29, 399-401 (2004).