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Isolation of Acetylcholinesterase Inhibitors from the Flowers of Chrysanthemum indicum Linne  

Lim, Soon-Sung (Regional Innovation Center, Hallym University)
Han, Sag-Myung (Department of Food Science and Nutrition, The Korean Institute of Nutrition, Hallym University)
Kim, Sun-Young (Department of Food Science and Nutrition, The Korean Institute of Nutrition, Hallym University)
Bae, Young-Soo (Department of Wood Science and Engineering, Kangwon National University)
Kang, Il-Jun (Department of Food Science and Nutrition, The Korean Institute of Nutrition, Hallym University)
Publication Information
Food Science and Biotechnology / v.16, no.2, 2007 , pp. 265-269 More about this Journal
Abstract
There is significant interest in finding new sources of acetylcholinesterase (AChE) inhibitors for use in treating Alzheimer's disease, since only a few AChE inhibitors are available for clinical use, such as galanthamine, physostigmine, and tacrine. The ethanol extract of Chrysanthemum indicum Linne flowers was analyzed and found to markedly decrease AChE activity. Acaciin and $acacetin-7-O-{\beta}-D-galactopyranoside$ were identified as the active compounds responsible for the AChE inhibition by using an activity-guided fractionation strategy. The relationship between structure and activity for five flavonoids (acaciin, $acacetin-7-O-{\beta}-D-galactopyranoside$, luteolin, and two other commercially available flavonoids, i.e., apigenin and acacetin) was also investigated, revealing that the presence of methoxy groups at C-4' in the B ring and a sugar at O-7 in ring A appear to be essential for the inhibition of AChE.
Keywords
acetylcholinesterase inhibitor; Chrysanthemum indicum; Acaciin; acacetin-7-O-$\beta$-D-galactopyranoside; luteolin;
Citations & Related Records
Times Cited By KSCI : 4  (Citation Analysis)
Times Cited By Web Of Science : 10  (Related Records In Web of Science)
Times Cited By SCOPUS : 11
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1 Yoshikawa M, Morikawa T, Murakami T, Toguchida I, Harima S, Matsuda H. Medicinal flowers. I. Aldose reductase inhibitors and three new eudesmane-type sesquiterpenes, kikkanols A, B, and C, from the flowers of Chrysanthemum indicum L. Chem. Pharm. Bull. 47: 340-345 (1999)   DOI   ScienceOn
2 Michael WW, Huang KC. The dried flower and petal of Chrysanthemum indicum L., C boreale Mak., and C.lavandulaefolium (Fisch.) Mak. p. 83. In: The Pharmacology of Chinese Herbs: 2nded. CRC Press, lnc., Boca Raton, FL, USA (1997)
3 Sugimoto H, Tsuchiya Y, Sugumi H, Higurashi K, Karibe N, Iimura Y, Sasaki A, Kawakami Y, Nakamura T, Araki S. Novel piperidine derivatives. Synthesis and anti-acetylcholinesterase activity of 1benzyl-4-[2-(N-benzoylamino)ethyl]piperidine derivatives. J. Med. Chem. 33: 1880-1887 (1990)   DOI
4 Jann MW. Rivastigmine, a new-generation cholinesterase inhibitor for the treatment of Alzheimer's disease. Pharmacotherapy 20: 1-12 (2000)   DOI   ScienceOn
5 Hana SY, Sweeneyb JE, Bachmanb ES, Schweigera EJ, Forlonic G, Coyleb JT, Davis BM, Joullie MM. Chemical and pharmacological characterization of galanthamine, an acetylcholinesterase inhibitor, and its derivatives. A potential application in Alzheimer's disease. Eur. J. Med. Chem. 27: 673-687 (1992)   DOI   ScienceOn
6 Loy C, Schneider L. Galantamine for Alzheimer's disease. Cochrane DB. Syst. Rev. 18: CD001747 (2004)
7 Cha JD, Jeong MR, Lee YE. Induction of apoptosis in human oral epidermoid carcinoma cells by essential oil of Chrysanthemum boreale Makino. Food Sci. BioTechnol. 14: 350-354 (2005)
8 Yoshikawa M, Morikawa T, Toguchida I, Harima S, Matsuda H. Medicinal flowers. II. Inhibitors of nitric oxide production and absolute stereostructures of five new germacrane-type sesquiterpenes, kikkanols D, D monoacetate, E, F, and F monoacetate from the flowers of Chrysanthemum indicum L. Chem. Pharm. Bull. 48: 651-656 (2000)   DOI   ScienceOn
9 Woo ER, Piao MS. Antioxidative constituents from Lycopus lucidus. Arch. Pharm. Res. 27: 173-176 (2004)   DOI   ScienceOn
10 Tabarrini O, Cecchetti V, Temperini A, Filipponi E, Lamperti MG, Fravolini A. Velnacrine thia-analogues as potential agents for treating Alzheimer's disease. Bioorgan. Med. Chem. 9: 2921-2928 (2001)   DOI   ScienceOn
11 Matsuda H, Morikawa T, Toguchida I, Harima S, Yoshikawa M. Medicinal flowers. VI. Absolute stereostructures of two new flavanone glycosides and a phenylbutanoid glycoside from the flowers of Chrysanthemum indicum L.: their inhibitory activities for rat lens aldose reductase. Chem. Pharm. Bull. 50: 972-975 (2002)   DOI   ScienceOn
12 Ingkaninan K, Temkitthawon P, Chuenchom K, Yuyaem T, Thongnoi W. Screening for acetylcholinesterase inhibitory activity in plants used in Thai traditional rejuvenating and neurotonic remedies. J. Ethnopharmacol. 89: 261-264 (2003)   DOI   ScienceOn
13 Fredj G, Dietlin F, Barbier G, Jasmin C, Bonhomme L, Esctein S, Misset JL, Meyer P, Kalifa D, Beugre T. Comparison oftacrine hepatotoxicity in patients with Alzheimer disease or AIDS. Therapie 47: 245-247 (1992)
14 Duh P, Tu Y, Yen G. Antioxidant activity of water extract of Harng Jyur (Chrysanthemum morifolium Ramat) Lebensm. -Wiss. Technol. 32: 269-277 (1999)   DOI   ScienceOn
15 Ellman GL, Lourtney DK, Andres V, Gmelin G A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 7: 88-95 (1961)   DOI   ScienceOn
16 Winkler J, Thai LJ, Gage FH, Fisher LJ. Cholinergic strategies for Alzheimer's disease. J. Mol. Med. 76: 555-567 (1998)   DOI
17 Nunomura A, Perry G, Aliev G, Hirai K, Takeda A, Balraj EK, Jones PK, Ghanbari H, Wataya T, Shimohama S, Chiba S, Atwood CS, Petersen RB, Smith MA. Oxidative damage is the earliest event in Alzheimer disease. J. Neuropath. Exp. Neur. 60: 759-767 (2001)   DOI
18 Bores GM, Huger FP, Petko W, Mutlib AE, Camacho F, Rush DK, Selk DE, Wolf V, Kosley RW Jr, Davis L, Vargas HM. Pharmacological evaluation of novel Alzheimer's disease therapeutics: acetylcholinesterase inhibitors related to galanthamine. J. Pharmacol. Exp. Ther. 277: 728-738 (1996)
19 Zhu S, Yang Y, Yu H, Ying Y, Zou G. Chemical composition and antimicrobial activity of the essential oils of Chrysanthemum indicum. J. Ethnopharmacol. 96: 151-158 (2005)   DOI   ScienceOn
20 Lane RM, Potkin SG, Enz A. Targeting acetylcholinesterase and butyrylcholinesterase in dementia. Int. J. Neuropsychoph. 9: 101-124 (2006)
21 Chatterjee A, Sarkar S, Saha SK. Acacetin 7-O-$\beta$-D-galactopyranoside from Chrysanthemum indicum. Phytochemistry 20: 1760-1761 (1981)   DOI   ScienceOn
22 Lleo A, Greenberg SM, Growdon JH. Current pharmacotherapy for Alzheimer's disease. Annu. Rev. Med. 57: 513-533 (2006)   DOI   ScienceOn
23 Wang ZG, Ren AN, Xu L, Sun XJ, Hua XB. The experimental study on the immunological and anti-inflammatory activities of Chrysanthemum indicum. Chinese J. Trad. Med. Sci. Technol. 2: 92-93 (2000)
24 Kim S, Cho J, Wee J, Jang M, Kim C, Rim Y, Shin S, Ma S, Moon J, Park K. Isolation and characterization of antioxidative compounds from the aerial parts of Angelica keiskei. Food Sci. Biotechnol. 14: 58-63 (2005)
25 Quinn DM. Acetylcholinesterase - enzyme structure, reaction dynamics, and virtual transition states. Chem. Rev. 87: 955-979 (1987)   DOI
26 Jeon JR, Park JR. Effects of Chrysanthemum boreale M. water extract on serum liver enzyme activities and Kupffer cells of carbon tetrachloride-induced rats. Food Sci. Biotechnol. 14: 290-296 (2005)
27 Wagner H, Aurnhammer G, Horammer L, Farkas L. Investigations on the glycosides of acacetin. II. Note on the identity of acaciin from Robinia pseudoacacia L. with Iinarin from Linaria vulgaris P. Mill. Chem. Ber. 102: 1445-1446 (1969)   DOI   ScienceOn
28 Duh P. Antioxidant activity of water extract of four Harng Jyur (Chrysanthemum morifolium Rarnat) varieties in soybean oil emulsion. Food Chem. 66: 471-476 (1999)   DOI   ScienceOn