Chemical composition of bioactive alkaloid extracts from some Narcissus species and varieties and their biological activity

Natural Product Communications

Volumn 9, Issue 8, 2014, Pages 1151-1155

  Havlasová, Jana ^a   Šafratová, Marcela ^b   Siatka, Tomáš ^c   Štěpánková, Šárka ^a   Novák, Zdeněk ^c   Ločárek, Miroslav ^b   Opletal, Lubomír ^b   Hrabinová, Martina ^d   Jun, Daniel ^d   Benešová, Nina ^b   Kuneš, Jiří ^c   Cahlíková, Lucie ^b  

^a UNIVERSITY OF PARDUBICE   (Czech Republic)

^b CHARLES UNIVERSITY   (Czech Republic)

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

^d UNIVERSITY OF DEFENCE   (Czech Republic)

Author keywords

Acetylcholinesterase; Alkaloids; Butyrylcholinesterase; GC MS; Narcissus; Prolyl oligopeptidase

Indexed keywords

ACETYLCHOLINESTERASE; ALKALOID; ALKALOID DERIVATIVE; CHOLINESTERASE; GALANTAMINE; INCARTINE; LYCORINE; PROLYL ENDOPEPTIDASE; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; CHEMICAL COMPOSITION; CHOLINESTERASE INHIBITION; DRUG IDENTIFICATION; DRUG INHIBITION; DRUG ISOLATION; IC 50; MASS FRAGMENTOGRAPHY; NARCISSUS; NARCISSUS JONQUILA; NARCISSUS NANUS; NONHUMAN; THIN LAYER CHROMATOGRAPHY;

ALKALOIDS; ENZYME INHIBITORS; NARCISSUS; PLANT EXTRACTS; SERINE ENDOPEPTIDASES;

EID: 84906688881     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x1400900823     Document Type: Article

References (41)

1. (a) Szlávik L, Gyuris Á, Minárovits J, Forgo P, Molnár J, Hohmann J. (2004) Alkaloids from Leucojum vernum and antiretroviral activity of Amaryllidaceae alkaloids. Planta Medica, 70, 871-873;
2. (b) Jitsuno M, Yokosuka A, Mimaki Y. (2009) Chemical constituents of the bulbs of Habranthus brychyandrus and their cytotoxic activities. Chemical & Pharmaceutical Bulletin, 57, 1153-1157;
3. (c) Kulhánková A, Cahlíková L, Novák Z, Macáková K, Kuneš J, Opletal L. (2013) Alkaloids from Zephyranthes robusta Baker and their acetylcholinesterase and butyrylcholinesterase inhibition activity. Chemistry & Biodiversity, 10, 1120-1127;
4. (d) Campbell WE, Nair JJ, Gammon DW, Bastida J, Codina C, Viladomat F, Smith PJ, Albrecht CF. (1998) Cytotoxic and antimalarial alkaloids from Brunsvigia littoralis. Planta Medica, 64, 91-93.
5. Hostettmann K, Borlotz A, Urbain A, Marston A. (2006) Natural product inhibitors of acetylcholinesterase. Current Organic Chemistry, 10, 825-847.
6. López S, Bastida J, Viladomat F, Codina C. (2002) Acetylcholinesterase inhibitory activity of some Amaryllidaceae alkaloids and Narcissus extracts. Life Sciences, 71, 2521-2529. (Pubitemid 35247960)
7. (a) Wimo A, Wimblad B, Stoffler A, Wirth Y, Mobius HJ. (2003) The magnitude of dementia occurrence in the world. Alzheimer Disease and Associated Disorders, 17, 63-67;
8. (b) Selkoe DJ. (1998) The cell biology of beta-amyloid precursor protein and presenilin in Alzheimer's disease. Trends in Cell Biology, 8, 447-453;
9. (c) Lahiri DK, Farlow MR, Greig NH, Sambamurti K. (2002) Current drug targets for Alzheimer's disease treatment. Drug Development Research, 56, 267-281;
10. (d) Moran MA, Mufson EJ, Gomez-Ramos P. (1993) Colocalization of cholinesterases with beta amyloid protein in aged and Alzheimer's brains. Acta Neuropathologica, 85, 362-369;
11. (e) Giacobini E. (2003) Cholinergic function and Alzheimer's disease. International Journal of Geriatric Psychiatry, 18, S1-S5.
12. (a) Polgár L. (2002) The prolyl oligopeptidase family. Cellular and Molecular Life Sciences, 59, 349-362;
13. (b) García-Horsman JA, Männistö PT, Venäläinen JI. (2007) On the role of prolyl oligopeptidase in health and disease. Neuropeptides, 41, 1-24;
14. (c) Puttonen KA, Lehtonen S, Raasmaja A, Männistö PT. (2006) A prolyl oligopeptidase inhibitor Z-Pro-Prolinal, inhibits glyceraldehyde-3- phosphate dehydrogenase translocation and production of reactive oxygen species in CV1-P cells exposed to 6-hydroxydopamine. Toxicoloxy in Vitro, 20, 1446-1454;
15. (d) Toide K, Shinoda M, Fujiwara T, Iwamoto Y. (1997) Effect of a novel prolyl endopeptidase inhibitor, JTP-4819, on spatial memory and central cholinergic neurons in aged rats. Pharmacology, Biochemistry and Behavior, 56, 427-434;
16. (e) Tarragó T, Kichik N, Claasen B, Prades R, Teixidó M, Giralt E. (2008) Baicalin, a prodrug able to reach the CNS, is a prolyl oligopeptidase inhibitor. Bioorganic & Medicinal Chemistry, 16, 7516-7524.
17. (a) Kington S. (2008) The international daffodil register and classified list 2008. Royal Horticultural Society, London;
18. (b) Pettit GR, Groszek G, Backhaus RA, Doubek DL, Barr RJ, Meerow AW. (1995) Antineoplastic agents, 301. An investigation of the Amaryllidaceae genus Hymenocallis. Journal of Natural Products, 58, 756-759;
19. (c) Pettit GR, Cragg GM, Singh SB, Duke JA, Doubek DL. (1990) Antineoplastic agents, 162. Zephyranthes candida. Journal of Natural Products, 53, 176-178;
20. (d) Bastida J, Lavilla R, Viladomat F. (2006) Chemical and biological aspects of Narcissus alkaloids. In The Alkaloids. Cordel GA. (Ed.). Elsevier, Chicago, 87-179.
21. Gorinova NI, Atanassov A, Stojanov D, Tencheva J. (1993) Influence of chemical composition of soil on the galanthamine content in Leucojum aestivum. Journal of Plant Nutrition, 16, 1631-1636.
22. Moraes-Cerdeira RM, Burandt CL, Bastos JK, Nanayakkara NPD, Mikell J, Thurn J, McChesney JD. (1997) Evaluation of four Narcissus cultivars as potential sources for galanthamine production. Planta Medica, 63, 472-474.
23. 1H NMR. Journal of Agricultural and Food Chemistry, 59, 3155-3161.
24. Ellman GL, Courtney KD, Andres V, Featherstone RM. (1961) A new rapid colorimetric determination of acetylcholinesterase activity. Biochemical Pharmacology, 7, 88-95.
25. Houghton P, Ren Y, Howes MJ. (2006) Acetylcholinesterase inhibitors from plants and fungi. Natural Product Reports, 23, 181-189.
26. Elgorashi EE, Stafford GI, van Staden J. (2004) Acetylcholinesterase enzyme inhibitory effects of Amaryllidaceae alkaloids. Planta Medica, 70, 260-262. (Pubitemid 38445195)
27. Nicolet Y, Lockridge O, Masson P, Fontecilla-Camps JC, Nachon F. (2003) Crystal structure of human butyrylcholinesterase and of its complexes with substrate and products. Journal of Biological Chemistry, 278, 41141-41147. (Pubitemid 37280939)
28. (a) Cahlíková L, Hrabinová M, Kulhá nková A, Benešová N, Chlebek J, Jun D, Novák Z, Macáková K, Kuneš J, Opletal L. (2013) Alkaloids from Chlidanthus fragrans and their acetylcholinesterase, butyrylcholinesterase and prolyl oligopeptidase activities. Natural Product Communications, 8, 1541-1544;
29. (b) Cahlíková L, Ločárek M, Benešová N, Kučera R, Chlebek J, Novák Z, Opletal L. (2013) Isolation and cholinesterase activity of Narcissus extracts and Amaryllidaceae alkaloid. Natural Product Communications, 8, 781-785;
30. (c) Cahlíková L, Zavadil S, Macáková K, Valterová I, Kulhánková A, Hošt'álková A, Kuneš J, Opletal L. (2011) Isolation and cholinesterase activity of Amaryllidaceae alkaloids from Nerine bowdenii. Natural Product Communications, 6, 1827-1830.
31. (a) Li H, Wang H, Chen JH, Wang LH, Zhang HS, Fan Y.(2003) Determination of amino acid neurotransmitters in cerebral cortex of rats administered with baicalin prior to cerebral ischemia by capillary electrophoresis-laser-induced fluorescence detection. Journal of Chromatography B, 788, 93-101;
32. (b) Lee H, Yang LL, Wang CC, Hu SY, Chang SF, Lee YH. (2003) Differential effects of natural polyphenols on neuronal survival in primary cultured central neurons against glutamate- and glucose deprivation-induced neuronal death. Brain Research, 986, 103-113.
33. Liu XS, Jiang J, Jiao XY, Wu YE, Lin JH, Cai YM. (2009) Lycorine induces apoptosis and down-regulation of Mc-1 in human leukemia cells. Cancer Letter, 274, 16-24.
34. (a) Jegorov A, Buchta M, Sedmera P, Kuzma M, Havlicek V. (2006) Accurate product ion mass spectra of galanthamine derivatives. Journal of Mass Spectrometry, 41, 544-548;
35. (b) Berkov S, Reyes-Chilpa R, Codina C, Viladomat F, Bastida J. (2007) Revised NMR data for incartine: an alkaloid from Galanthus elwesii. Molecules, 12, 1430-1435.
36. Kreh M, Matusch R, Witte L. (1995) Capillary gas chromatography-mass spectrometry of Amaryllidaceae alkaloids. Phytochemistry, 38, 773-776.
37. Berkov S, Viladomat F, Codina C, Suárez S, Revelo A, Bastida J. (2012) GC-MS of Amaryllidaceous galanthamine-type alkaloids. Journal of Mass Spectrometry, 47, 1065-1073.
38. Berkov S, Sidjimova B, Evstatieva L, Popov S. (2004) Instraspecific variability in the alkaloid metabolism of Galanthus elwesii. Phytochemistry, 65, 579-586. (Pubitemid 38328483)
39. de Andrade JP, Pigni NB, Torras-Claveria L, Berkov S, Codina C, Viladomat F, Bastida J. (2012) Bioactive alkaloid extracts from Narcissus broussonetti: Mass spectral studies. Journal of Pharmaceutical and Biomedical Analysis, 70, 13-25.
40. Youssef DTA. (1999) Further alkaloids from the flowers of Pancratium maritimum. Pharmazie, 54, 535-537.
41. Torres JC, Pinto AC, Garden SJ. (2004) Application of a catalytic palladium biaryl synthesis reaction, via C-H functionalization, to the total synthesis of Amaryllidaceae alkaloids. Tetrahedron, 60, 9889-9900. (Pubitemid 39296778)