Isolation and cholinesterase activity of amaryllidaceae alkaloids from Nerine bowdenii

Natural Product Communications

Volumn 6, Issue 12, 2011, Pages 1827-1830

  Cahlíková, Lucie ^a   Zavadil, Stanislav ^a   Macaḱová, Katerǐna ^a   Valterová, Irena ^b   Kulhańková, Andrea ^a   Hošt'álková, Anna ^a   Kuneš, Jiří ^b   Opletal, Lubomír ^a  

^a Charles University in Prague Faculty of Pharmacy   (Czech Republic)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

Acetylcholinesterase; Belladine; Butyrylcholinesterase; GC MS; Nerine bowdenii

Indexed keywords

11 O ACETYL 1,2 EPOXYAMBELLINE; 11 O ACETYLAMBELLINE; 3 ACETYLNERBOWDINE; ACETYLCHOLINESTERASE; ACETYLFALCATINE; ALKALOID; AMBELLINE; BELLADINE; BOWDENSINE; BUPHANAMINE; BUPHANIDRINE; BUPHANISINE; CARANINE; CHOLINESTERASE; CRINAMIDINE; CRINAMINE; CRININE; GALANTAMINE; HUPERZINE A; N DEMETHYLBELLADINE; NERINE BOWDENII EXTRACT; PLANT EXTRACT; POWELLINE; UNCLASSIFIED DRUG; UNDULATINE;

AMARYLLIDACEAE; ARTICLE; CHEMICAL COMPOSITION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG SCREENING; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME INHIBITION; ERYTHROCYTE GHOST; HUMAN; HUMAN CELL; IC 50; MASS FRAGMENTOGRAPHY; NERINE BOWDENII; NONHUMAN; PHYTOCHEMISTRY; PLANT BULB; THIN LAYER CHROMATOGRAPHY;

EID: 83455211112     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x1100601210     Document Type: Article

References (36)

1. Johnson N, Davis T, Bosanquet N. (2000) The epidemic of Alzheimer's disease; how can we manage the costs? Pharmacoeconomics, 18, 215-223.
2. (a) Lahiri DK, Farlow MR, Greig NH, Sambamurti K. (2002) Current drug targets for Alzheimer's disease treatment. Drug Development Research, 56, 267-281;
3. (b) Rahman AU, Choudhary MI. (2001) Bioactive natural products as a potential source of new pharmacophores a theory of memory. Pure and Applied Chemistry, 73, 555-560;
4. (c) Greig NH, Lahiri DK, Sambamurti K. (2002) Butyrylcholinesterase: an important new target in Alzheimer's disease therapy. International Psychogeriatrics, 14, 77-91;
5. (d) Fulton B, Benfield P. (1996) Galanthamine. Drugs & Aging, 9, 60-65;
6. (e) Lleó A. (2007) Current therapeutic options for Alzheimer's disease. Current Genomics, 8, 550-558;
7. (f) Recanatini M, Valenti P. (2004) Acetylcholinesterase inhibitors as a starting point towards improved Alzheimer's disease therapeutics. Current Pharmaceutical Design, 10, 3157-3166. (Pubitemid 39242910)
8. Bastida J, Lavilla R, Viladomat F. (2006) Chemical and biological aspects of Narcissus alkaloids. In The Alkaloids, Vol. 63, Cordell GA. (Ed.). Elsevier Scientific: Amsterdam, NL, pp. 87-179.
9. (a) Evidente A, Kornienko A. (2009) Anticancer evaluation of structurally diverse Amaryllidaceae alkaloids and their synthetic derivatives. Phytochemistry Reviews, 8, 449-459;
10. (b) Toriizuka Y, Kinoshita E, Kogure N, Kitajima M, Ishiyama A, Otoguro K, Yamada H, Ōmura S, Takayama H. (2008) New lycorine-type alkaloid from Lycoris traubii and evaluation of antitropanosomal and antimalarial activities of lycorine derivatives. Bioorganic & Medicinal Chemistry, 16, 10182-10189;
11. (c) Weniger B, Italiano L, Beck JP, Bastida J, Bergoñon S, Codina C, Lobstein A, Anton R. (1995) Cytotoxic activity of Amaryllidaceae alkaloids. Planta Medica, 61, 77-79;
12. (d) Zupkó I, Réthy B, Hohmann J, Molnár J, Ocsovczki I, Falaky G. (2009) Antitumor activity of alkaloids derived from Amaryllidaceae species. In Vivo, 23, 41-48;
13. (e) Lamoral-Theys D, Andolfi A, van Goietsenoven G, Cimmino A, Le Calvé B, Wauthoz N, Mégalizzi V, Gras T, Bruyère C, Dubois C, Mathieu V, Kornienko A, Kiss R, Evidente A. (2009) Lycorine, the main phenanthridine Amaryllidaceae alkaloid, exhibits significant antitumor activity in cancer cells that display resistance to proapoptotic stimuli: an investigation of structure-activity relationship and mechanistic insight. Journal of Medicinal Chemistry, 52, 6244-6256.
14. (a) Rhee IK, van de Meent M, Ingkaninan K, Verpoorte R. (2001) Screening for acetylcholinesterase inhibitors from Amaryllidaceae using silica gel thin-layer chromatography in combination with bioactivity staining. Journal of Chromatography A, 915, 217-223;
15. (b) Marston A, Kissling J, Hostettmann K. (2002) A rapid TLC bioautographic method for the detection of acetylcholinesterase and butyrylcholinesterase inhibitors in plants. Phytochemical Analysis, 13, 51-54. (Pubitemid 34126614)
16. Rix M, Phillips R. (1983) The bulb book: a photographic guide to over 800 hardy bulbs, Pan Books Ltd., London, GB, pp. 171.
17. (a) Rhee IK, Appels N, Hofte B, Karabatak B, Erkelens C, Stark LM, Flippin LA, Verpoorte R. (2004) Isolation of the acetylcholinesterase inhibitor ungeremine from Nerine bowdenii by preparative HPLC coupled on-line to a flow assay system. Biological & Pharmaceutical Bulletin, 27, 1804-1809;
18. (b) van Rijn RM, Rhee IK, Verpoorte R. (2010) Isolation of acetylcholinesterase inhibitory alkaloids from Nerine bowdenii. Natural Product Research, 24, 222-225.
19. (a) De Angelis G, Wildman W. (1969) Identification of Amaryllidaceae alkaloids using ORD and CD spectroscopy. Tetrahedron Letters, 9, 729-732;
20. (b) Eichhorn J, Takada T, Kita Y, Zenk MH. (1998) Biosynthesis of the Amaryllidaceae alkaloid galanthamine. Phytochemistry, 49, 1037-1047;
21. (c) Nair JJ, Campbell WE, Brun R, Viladomat F, Codina C, Bastida J. (2005) Alkaloids from Nerine filifolia. Phytochemistry, 66, 373-382;
22. (d) Jin Z. (2009) Amaryllidaceae and Sceletium alkaloids. Natural Product Reports, 26, 363-381.
23. (a) López S, Bastida J, Viladomat F, Codina C. (2002) Acetylcholinesterase inhibitory activity of same Amaryllidaceae alkaloids and Narcissus extracts. Life Sciences, 71, 2521-2529;
24. (b) Elgorashi EE, Stafford GI, van Staden J. (2004) Acetylcholinesterase enzyme inhibitory effects of Amaryllidaceae alkaloids. Planta Medica, 70, 258-260;
25. (c) Houghton PJ, Agbedahunsi JM, Adegbulugbe A. (2004) Choline esterase inhibitory properties of alkaloids from two Nigerian Crinum species. Phytochemistry, 65, 2893-2896;
26. (d) Houghton PJ, Ren Y, Howes MJ. (2006) Acetylcholinesterase inhibitors from plants and fungi. Natural Product Reports, 23, 181-189;
27. (e) Cahlíková L, Kulhánková A, Urbanová K, Valterová I, Macáková K, Kuneš J. (2010) Analysis of Amaryllidaceae alkaloids from Zephyranthes robusta by GC-MS and their cholinesterase activity. Natural Product Communications, 5, 1201-1204;
28. (f) Cahlíková L, Valterová I, Macáková K, Opletal L. (2011) Analysis of Amaryllidaceae alkaloids from Zephyranthes grandiflora by GC-MS and their cholinesterase activity. Revista Brasileira de Farmacognosia/Brazilian Journal of Pharmacognosy, 21, 575-580;
29. (g) Cahlíková L, Macáková K, Zavadil S, Jiroš P, Opletal L, Urbanová K, Jahodář L. (2011) Analysis of Amaryllidaceae alkaloids from Chlidanthus fragrans by GC-MS and their cholinesterase activity. Natural Product Communications, 6, 603-606.
30. (a) Kreh M, Matusch R, Witte L. (1995) Capillary gas chromatography-mass spectrometry of Amaryllidaceae alkaloids. Phytochemistry, 38, 773-776;
31. (b) Berkov S, Bastida J, Nikolova M, Viladomat F, Codina C. (2008) Rapid TLC/GC-MS identification of acetylcholinesterase inhibitors in alkaloid extract. Phytochemical Analysis, 19, 411-419;
32. (c) Viladomat F, Codina C, Bastida J, Mathee S, Campbell WE. (1995) Further alkaloids from Brunsvigia josephinae. Phytochemistry, 40, 961-965;
33. (d) Ghosal S, Shanthy A, Singh SK. (1988) Isocraugsodine, an N-arylidenephenethylamine from Crinum asiaticum and its E-Zisomerism. Phytochemistry, 27, 1849-1852;
34. (e) Machocho A, Chhabra SC, Viladomat F, Codina C, Bastida J. (1999) Alkaloids from Ammocharis tinneana. Phytochemistry, 51, 1185-1191.
35. (a) Steck TL, Kant JA. (1974) Preparation of impermeable ghosts and inside-out vesicles from human erythrocyte membranes. Methods in Enzymology, 31 (Pt A), 172-180;
36. (b) Ellman GL, Courtney KD, Andres V, Featherstone RM. (1961) A new rapid colorimetric determination of acetylcholinesterase activity. Biochemical Pharmacology, 7, 88-95.