Cholinesterase inhibitors from botanicals

Pharmacognosy Reviews

Volumn 7, Issue 14, 2013, Pages 121-130

  Ahmed, Faiyaz ^a   Ghalib, Raza ^b   Sasikala, P ^a   Mueen Ahmed, K ^c  

^a INDIAN INSTITUTE OF FOOD PROCESSING TECHNOLOGY   (India)

^b INTERNATIONAL ISLAMIC UNIVERSITY MALAYSIA   (Malaysia)

^c KING FAISAL UNIVERSITY   (Saudi Arabia)

Author keywords

Acetylcholinesterase; alkaloids; alzheimer s disease; butyrylcholinesterase; buxaceae

Indexed keywords

2 DEMETHOXY MONTANINE; 3 EPI HYDROXYBULBISPERMINE; ALKALOID; ALPHA SOLANINE; BULBOCAPNINE; BUXAMINE A; BUXAMINE B; CHOLINESTERASE INHIBITOR; CONYPODODIOL; CORONARIDINE; CORYDALINE; CORYDINE; CORYNOLIN; CRININE; CYCLOBUXOVIRIDINE; GALANTAMINE; HAEMANTHAMINE; LYCORINE; MOENJODARAMINE; N NOR GALANTHAMINE; PALMATINE; PHYSOSTIGMINE; PLANT EXTRACT; PROTOPINE; RUPICOLINE; SPIROFORNABUXINE; TAZETTINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VOACANGINE; VOACANGINE HYDROXYINDOLENINE;

AMARANTHACEAE; AMARYLLIDACEAE; APOCYNACEAE; BUXACEAE; DRUG ISOLATION; DRUG STRUCTURE; LAMIACEAE; LYCOPODIACEAE; MEDICINAL PLANT; NONHUMAN; PAPAVERACEAE; REVIEW;

EID: 84889608843     PISSN: 09737847     EISSN: 09762787     Source Type: Journal    
DOI: 10.4103/0973-7847.120511     Document Type: Review

References (76)

1. Bartolucci C, Perola E, Pilger C, Fels G, Lamba D. Three-dimensional structure of a complex of galanthamine (Nivalin) with acetylcholinesterase from Torpedo californica: Implications for The design of new anti-Alzheimer drugs. Proteins 2001;42:182-91. (Pubitemid 32047326)
2. Lahiri DK, Farlow MR, Greig NH, Sambamurti K. Current drug Targets for Alzheimer's disease Treatment. Drug Dev Res 2002;56:267-81. (Pubitemid 35168304)
3. Perry EK. The cholinergic hypothesis: Ten years on. Br Med Bull 1986;42:63-9.
4. Bartus BT, Dean RL, Beer B, Lippa AS. The cholinergic hypothesis of geriatric memory dysfunction. Science 1982;217:408-17. (Pubitemid 12048290)
5. Greig NH, Lahiri DK, Sambamurti K. Butyrylcholinesterase: An important new Target in Alzheimer's disease Therapy. Int Psychogeriatr 2002;14:77-91. (Pubitemid 36206092)
6. Shetty HG, Woodhouse K. Geriatrics. In: Walker R, Edwards C, editors. Clinical Pharmacy and Therapeutics. 2nd ed. Edinburgh: Churchill Livingstone; 1999.
7. Lopez S, Bastida J, Viladomat F, Codina C. Acetylcholinesterase inhibitory activity of some Amaryllidaceae alkaloids and Narcissus extracts. Life Sci 2002;71:2521-9. (Pubitemid 35247960)
8. Das A, Shanker G, Nath C, Pal R, Singh S, Singh HK. A comparative study in rodents of standardized extracts of Bacopa monniera and Ginkgo biloba anticholinesterase and cognitive enhancing activities. Pharmacol Biochem Behav 2002;73:893-900. (Pubitemid 35246239)
9. Orhan I, Sener B, Choudhary MI, Khalid A. Acetylcholinesterase and butyrylcholinesterase inhibitory activity of some Turkish medicinal plants. J Ethnopharmacol 2004;91:57-60. (Pubitemid 38270227)
10. Perry NS, Houghton PG, Theolad AE, Jenner P, Perry EK. In vitro inhibition of human erythrocyte acetylcholinesterase by Salvia lavandulaefolia essential oil and constituent Terpenes. J Pharm Pharmacol 2000;52:895-902. (Pubitemid 30461925)
11. Perry NS, Houghton PG, Sampson J, Theolad AE, Hart S, Lis-balchin M, et al. In vitro activities of Salvia lavandulaefolia (Spanish Sage) relevant To Treatment of Alzheimer's disease. J Pharm Pharmacol 2001;53:1347-56. (Pubitemid 32982251)
12. Mukherjee PK, Kumar V, Mal M, Houghtona PJ. Acetylcholinesterase inhibitors from plants. Phytomedicine 2007;14:289-300. (Pubitemid 46415622)
13. Orhan I, Sener B. Sustainable use of various Amaryllidaceae plants against Alzheimer's disease. Proc. WOCMAP III. In: Franz C, Máthé A, Craker LE, Gardner ZE, editors. Targeted Screening of MAPs, Economics and Law. vol. 4., Acta Hort 678, ISHS 2005.
14. Kim SR, Hwang SY, Jang YP, Park MJ, Markelonis GJ, Oh TH, et al. Protopine from Corydalis Ternata has anticholinesterase and antiamnesic activities. Planta Med 1999;65:218-21. (Pubitemid 29186073)
15. Khan I, Nisar M, Khan N, Saeed M, Nadeem S, Fazal-ur-Rehman, et al. Structural insights To investigate Conypododiol as a dual cholinesterase inhibitor from Asparagus adscendens. Fitoterapia 2010;81:1020-5.
16. Adsersen A, Kjolbye A, Dall O, Jager AK. Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Corydalis cava Schweigg and Kort. J Ethnopharmacol 2007;113:179-82. (Pubitemid 47077855)
17. Ata A, Iverson CD, Kalhari KS, Akhter S, Betteridge J, Meshkatalsadat MH, et al. Triterpenoidal alkaloids from Buxus hyrcana and Their enzyme inhibitory, anti-fungal and anti-leishmanial activities. Phytochemistry 2010;71:1780-6.
18. Choudhary MI, Atta-ur-Rahman, Freyer AJ, Shamma M. New alkaloids from Buxus papilosa. J Nat Prod 1987;50:84-8.
19. Atta-ur-Rahman, Nisa M, Farhi S. The isolation and structure of ''moenjodaramine'' and ''harappamine''-two new alkaloids from Buxus papilosa. Z Naturforsch C 1984;39B: 524-7.
20. Mokry P, Voticky Z. Buxus alkaloids. X X. Alkaloids of Buxus arborescens Mill. Chemicke Zvesti 1984;38:101-9.
21. Vassova A, Voticky Z, Cernik J, Tomko J. Buxus alkaloids. XVIII. Alkaloids of Buxus harlandi Hance. Chemicke Zvesti 1980;34:706-11.
22. Fourneau C, Hocquemiller R, Guedon D, Cave A. Spirofornabuxine, a novel Type of Buxus alkaloid. Tetrahedron Lett 1997;38:2965-8. (Pubitemid 27180241)
23. Roddick JG. The acetylcholinesterase inhibitory activity of steroidal glycoalkaloids and Their aglycones. Phytochemistry 1989;28:2631-4.
24. McGehee DS, Krasowski MD, Fung DL, Wilson B, Gronert GA, Moss J. Cholinesterase inhibition by potato glycoalkaloids slows mivacurium metabolism. Anesthesiology 2000;93:510-9. (Pubitemid 30620325)
25. Andrade MT, Lima JA, Pinto AC, Rezende CM, Carvalho MP, Epifanio RA. Indole alkaloids from Tabernaemontana australis (Muell. Arg) Miers That inhibit acetylcholinesterase enzyme. Bioorg Med Chem 2005;13:4092-5. (Pubitemid 40725042)
26. Karczmar A. Invited review: Anticholinesterases: Dramatic aspects of Their use and misuse. Neurochem Int 1998;32:401-11. (Pubitemid 28287192)
27. Kim DK. Inhibitory effect of corynoline isolated from The aerial parts of Corydalis incisa on The acetylcholinesterase. Arch Pharm Res 2002;25:817-9.
28. Kim DK, Lee KT, Baek NI, Kim SH, Park HW, Lim JP, et al. Acetylcholinesterase inhibitors from The aerial parts of Corydalis speciosa. Arch Pharm Res 2004;27:1127-31.
29. Halldorsdottir ES, Jaroszewski JW, Olafsdottir ES. Acetylcholinesterase inhibitory activity of lycopodane-type alkaloids from The Icelandic Lycopodium annotinum ssp. alpestre. Phytochemistry 2010;71:149-57.
30. Park CH, Kim SH, Choi W, Lee YJ, Kim JS, Kang SS, et al. Novel anticholinesterase and antiamnesic activities of dehydroevodiamine, a constituent of Evodia rutaecarpa. Planta Med 1996;62:405-9. (Pubitemid 26370329)
31. Tang XC, Kindel GH, Kozikowski AP, Hanin I. Comparison of The effects of natural and synthetic huperzine: A on rat brain cholinergic function in vitro and in vivo. J Ethnopharmacol 1994;44:147-55.
32. Ashani Y, Grunwald J, Kronman C, Velan B, Shafferman A. Role of Tyrosine 337 in The binding of huperzine A To The active site of human acetylcholinesterase. Mol Pharmacol 1994;45:555-60. (Pubitemid 24094947)
33. Rahman AU, Choudhary MI. Bioactive natural products as a potential source of new pharmacophores-A Theory of memory. Pure Appl Chem 2001;73:555-60.
34. Rhee IK, Meent MV, Ingkaninan K, Verpoorte R. Screening for acetylcholinesterase inhibitors from Amaryllidaceae using silica gel Thin-layer chromatography in combination with bioactivity staining. J Chromatogr A 2001;915:217-23. (Pubitemid 32289341)
35. Rizzi A, Schuh R, Bruckner A, Cvitkovich B, Kremser L, Jordis U, et al. Enantiomeric resolution of galantamine and related drugs used in anti-Alzheimer Therapy by means of capillary zone electrophoresis employing derivatized cyclodextrin selectors. J Chromatogr B 1999;730:167-75. (Pubitemid 29308882)
36. 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 2003;89:261-4. (Pubitemid 37378200)
37. Atta-ur-Rahman, Alam M, Nasir H, Dagne E, Yenesew A. Three steroidal alkaloids from Buxus hildebrandtii. Phytochemistry 1990;29:1293-6.
38. Loru F, Duval D, Aumelas A, Akeb F, Guedon D, Guedj R. Four steroidal alkaloids from The leaves of Buxus sempervirens. Phytochemistry 2000;54:951-7.
39. Guo H, Cai XH. Triterpenoid alkaloids from Buxus rugulosa. Chem Nat Comp 2008;44:206-7.
40. Khalid A, Zaheer-ul-Haq, Ghayur MN, Fareeda Feroz F, Atta-ur-Rahman, Gilanib AH, et al. Cholinesterase inhibitory and spasmolytic potential of steroidal alkaloids. J Steroid Biochem Mol Biol 2004;92:477-84. (Pubitemid 40187165)
41. Choudhary MI, Shahnaz S, Parveen S, Khalid A, Mesaik MA, Ayatollahi SAM, et al. New cholinesterase-inhibiting Triterpenoid alkaloids from Buxus hyrcana. Chem Biodivers 2006;3:1039-52.
42. Atta-ur-Rahman, Parveen S, Khalid A, Farooq A, Choudhary MI. Acetyl and butyrylcholinesterase-inhibiting Triterpenoid alkaloids from Buxus papillosa. Phytochemistry 2001;58:963-8.
43. Atta-ur-Rahman, Parveen S, Khalid A, Farooq A, Ayattollahi SA, Choudhary MI. Acetylcholinesterase inhibiting Triterpenoidal alkaloids from Buxus hyrcana. Heterocycles 1998;49:481-8.
44. Yan YX, Hu XD, Chen JC, Sun Y, Zhang XM, Qing C, et al. Cytotoxic Triterpenoid alkaloids from Buxus microphylla. J Nat Prod 2009;72:308-11.
45. Ahmed E, Nawaz SA, Malik A, Choudhary MI. Isolation and cholinesterase-inhibition studies of sterols from Haloxylon recurvum. Bioorg Med Chem Lett 2006;16:573-80. (Pubitemid 43014839)
46. Ozturk M, Kolak U, Topcu G, Oksuz S, Choudhary MI. Antioxidant and anticholinesterase active constituents from Micromeria cilicica by radical-scavenging activity-guided fractionation. Food Chem 2011;126:31-8.
47. Jung M, Park M. Acetylcholinesterase inhibition by flavonoids from Agrimonia pilosa. Molecules 2007;12:2130-9.
48. Orhan I, Senol FS, Kartal M, Dvorska M, Zemlicka M, Smejkal K, et al. Cholinesterase inhibitory effects of The extracts and compounds of Maclura pomifera (Rafin.) Schneider. Food Chem Toxicol 2009;47:1747-51.
49. Shahwar D, Shafiq-Ur-Rehman, Raza MA. Acetyl cholinesterase inhibition potential and antioxidant activities of ferulic acid isolated from Impatiens bicolor Linn. J Med Plant Res 2010;4:260-6.
50. Kivrak I, Mehmet Emin Duru ME, Ozturk M, Mercan N, Harmandar M, Topcu G. Antioxidant, anticholinesterase and antimicrobial constituents from The essential oil and ethanol extract of Salvia potentillifolia. Food Chem 2009;116:470-9.
51. Chung YK, Heo HJ, Kim EK, Kim HK, Huh TL, Lim Y, et al. Inhibitory effect of ursolic acid purified from Origanum majorana L on The acetylcholinesterase. Mol Cells 2001;11:137-43. (Pubitemid 33663351)
52. Menichini F, Tundis R, Loizzo MR, Bonesi M, Marrelli M, Statti GA, et al. Acetylcholinesterase and butyrylcholinesterase inhibition of ethanolic extract and monoterpenes from Pimpinella anisoides V Brig. (Apiaceae). Fitoterapia 2009;80:297-300.
53. Vorbrueggen H, Pakrashi SC, Djerassi C. Terpenoids. LIV. Studies on Indian medicinal plants. Arborinol, a new Triterpene Type. Justus Liebigs Annalen der Chemie 1963;668:57-76.
54. Orhan I, Terzioglu S, Sener B. á-onocerin: An acetylcholinesterase inhibitor from Lycopodium clavatum. Planta Med 2003;69:1-3.
55. Urbain A, Marston A, Queiroz EF, Ndjoko K, Hostettmann K. Xanthones from Gentiana campestris as new acetylcholinesterase inhibitors. Planta Med 2004;70:1011-4. (Pubitemid 39457816)
56. Sancheti S, Sanchet S, Um BH, Seo SY. 1,2,3,4,6-penta-O-g alloyl-â-d-glucose: A cholinesterase inhibitor from Terminalia chebula. S Afr J Bot 2010;76:285-8.
57. Lee KY, Sung SH, Kim YC. New acetylcholinesterase inhibitory pregnane glycosides of Cynanchum atratum roots. Helv Chim Acta 2003;86:474-83. (Pubitemid 36348398)
58. Sung SH, Kang SY, Lee KY, Park MJ, Kim JH, Park JH, et al. (+)-á-Viniferin, a stilbene Trimer from Caragana chamlague, inhibits acetylcholinesterase. Biol Pharm Bull 2002;25:125-7.
59. Riaz N, Malik A, Aziz-ur-Rehman, Muhammad P, Nawaz SA, Choudhary MI. Cholinesterase inhibiting withanolides from Ajuga brateosa. Chem Biodivers 2004;1:1289-95.
60. Von BM, Endress PK, Qiu Y-L. Phylogenetic relationships in Buxaceae based on nuclear internal Transcribed spacers and plastid ndhF sequences. Int J Plant Sci 2000;161:785-92.
61. Devkota KP, Lenta BN, Fokou PA, Sewald N. Terpenoid alkaloids of The Buxaceae family with potential biological importance. Nat Prod Rep 2008;25:612-30. (Pubitemid 351728057)
62. Vieira Pde B, Giordani RB, De Carli GA, Zuanazzi JA, Tasca T. Screening and bioguided fractionation of Amaryllidaceae species with anti-Trichomonas vaginalis activity. Planta Med 2011;77:1054-9.
63. Hostettmann K, Borloz A, Urbain A, Marston A. Natural product inhibitors of acetylcholinesterase. Curr Org Chem 2006;10:825-47.
64. Campbell WE, Nair JJ, Gammon DW, Bastida J, Codina C, Viladomat F, et al. Cytotoxic and antimalarial alkaloids from Brunsvigia littoralis. Planta Med 1988;64:91-3.
65. Hohmann J, Forgo P, Molnár J, Wolfard K, Molnár A, Thalhammer T, et al. Antiproliferative Amaryllidaceae alkaloids isolated from The bulbs of Sprekelia formosissima and Hymenocalisxfestalis. Planta Med 2002;68:454-7. (Pubitemid 34606692)
66. Szlávik L, Gyuris A, Minárovits J, Forgo P, Molnár J, Hohmann J. Alkaloids from Leucojum vernum and antiretroviral activity of Amaryllidaceae alkaloids. Planta Med 2004;70:871-3. (Pubitemid 39361759)
67. Park SY. Potential Therapeutic agents against Alzheimer's disease from natural sources. Arch Pharm Res 2010;33:1589-609.
68. Ortega MG, Agnese AM, Barboza GE, Cabrera JL. Seasonal study of The alkaloid pattern of Huperzia saururus with habitat in Cordoba province (Argentina). J Argent Chem Soc 2007;95:1-9.
69. Ma X, Gang DR. The Lycopodium alkaloids. Nat Prod Rep 2004;21:752-72. (Pubitemid 40033085)
70. Kawakami Y, Inoue A, Kawai T, Wakita M, Sugimoto H, Hopfinger AJ. The rationale for E2020 as a potent acetylcholinesterase inhibitor. Bioorg Med Chem Lett 1996;4:1429-46. (Pubitemid 26319994)
71. Kryger G, Silman I, Sussman JL. Structure of acetylcholinesterase complexed with E2020 (Aricept): Implications for The design of new anti-Alzheimer drugs. Structure 1999;7:297-307. (Pubitemid 29159689)
72. Nightingale SL. Donepezil approved for Treatment of Alzheimer's disease. JAMA 1997;277:10. (Pubitemid 27009028)
73. Greenblatt HM, Kryger G, Lewis T, Silman I, Sussman JL. Structure of acetylcholinesterase complexed with (-)-galanthamine at 2.3A resolution. FEBS Lett 1999;463:321-6. (Pubitemid 30001943)
74. Bar-On P, Millard CB, Harel M, Dvir H, Enz A, Sussman JL, et al. Kinetic and structural studies on The interaction of cholinesterases with The anti-Alzheimer drug rivastigmine. Biochemistry 2002;41:3555-64. (Pubitemid 34224667)
75. Bai DL, Tang XC, He XC. Huperzine A. A potential Therapeutic agent for Treatment of Alzheimer's disease. Curr Med Chem 2000;7:355-74. (Pubitemid 30396443)
76. Wang R, Yan H, Tang XC. Progress in studies of huperzine A, a natural cholinesterase inhibitor from Chinese herbal medicine. Acta Pharmacol Sin 2006;27:1-26. (Pubitemid 43051942)