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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)
Publication Information
Natural Product Sciences / v.17, no.2, 2011 , pp. 108-112 More about this Journal
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
Corydalis turtschaninovii; Papaveraceae; Isoquinoline alkaloids; Cholinesterase; Alzheimer's disease; Structures and activity relationship;
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1 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).   DOI   ScienceOn
2 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).   DOI
3 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).
4 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).   DOI   ScienceOn
5 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).   DOI   ScienceOn
6 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).   DOI   ScienceOn
7 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).
8 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).
9 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).   DOI
10 Kiryakov, H.G., Iskrenova, E., Daskalova, E., Kuzmanov, B., and Evstatieva, L., Alkaloids of Corydalis slivenensis. Planta Med. 44, 168-170 (1982).   DOI
11 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).   DOI   ScienceOn
12 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).   DOI
13 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).   DOI   ScienceOn
14 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).   DOI   ScienceOn
15 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).
16 Ito, C., Mizuno, T., Wu, T.S., and Furukawa, H., Alkaloids from Corydalis. Phytochemistry 29, 2044-2045 (1990).   DOI   ScienceOn
17 Giacobini, E., The cholinergic system in Alzheimer disease. Prog. Brain Res. 84, 321-332 (1990).
18 Houghton, P.J., Ren, Y., and Howes, M.J., Acetylcholinesterase inhibitors from plants and fungi. Nat. Prod. Rep. 23, 181-199 (2006).   DOI   ScienceOn
19 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).   DOI   ScienceOn
20 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).   DOI   ScienceOn
21 Giacobini, E., Cholinesterase inhibitors: from the calabar bean to Alzheimer therapy. eds. by Giacobini, E., Dunitz, M., Thonex-Geneva, pp. 181-226 (2000).
22 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).
23 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).   DOI   ScienceOn