The coumarin scopoletin potentiates acetylcholine release from synaptosomes, amplifies hippocampal long-term potentiation and ameliorates anticholinergic- and age-impaired memory

Neuroscience - Tập 197 - Trang 280-292 - 2011
A. Hornick1, A. Lieb1, N.P. Vo2, J.M. Rollinger3, H. Stuppner3, H. Prast1
1Institute of Pharmacy/Pharmacology and Toxicology, University of Innsbruck, Peter-Mayr-Str.1, A-6020 Innsbruck, Austria
2Pharmacology and Clinical Pharmacy Department, School of Pharmacy, Ho Chi Minh City University of Medicine and Pharmacy, 41 Dinh Tien Hoang Street, District 1, Ho Chi Minh City, Vietnam
3Institute of Pharmacy/Pharmacognosy and Center for Molecular Biosciences Innsbruck, University of Innsbruck, Innrain 52c, A-6020 Innsbruck, Austria

Tài liệu tham khảo

Alkondon, 1993, Diversity of nicotinic acetylcholine receptors in rat hippocampal neurons, J Pharmacol Exp Ther, 265, 1455 Alkondon, 2004, The nicotinic acetylcholine receptor subtypes and their function in the hippocampus and cerebral cortex, Prog Brain Res, 145, 109, 10.1016/S0079-6123(03)45007-3 Bartolini, 1996, Aniracetam restores object recognition impaired by age, scopolamine, and nucleus basalis lesions, Pharmacol Biochem Behav, 53, 277, 10.1016/0091-3057(95)02021-7 Bertholet, 1991, Spatial and non-spatial spontaneous alternation and hippocampal mossy fibre distribution in nine inbred mouse strains, Behav Brain Res, 43, 197, 10.1016/S0166-4328(05)80071-3 Blesa, 2003, Galantamine provides sustained benefits in patients with “advanced moderate” Alzheimer's disease for at least 12 months, Dement Geriatr Cogn Disord, 15, 79, 10.1159/000067974 Bliss, 1993, A synaptic model of memory: long-term potentiation in hippocampus, Nature, 361, 31, 10.1038/361031a0 Boess, 2007, The novel alpha7 nicotinic acetylcholine receptor agonist N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-[2-(methoxy)phenyl]-1-benzofuran-2-carboxamide improves working and recognition memory in rodents, J Pharmacol Exp Ther, 321, 716, 10.1124/jpet.106.118976 Bontempi, 2003, Cognitive enhancing properties and tolerability of cholinergic agents in mice: a comparative study of nicotine, donepezil, and SIB-1553A, a subtype-selective ligand for nicotinic acetylcholine receptors, Neuropsychopharmacology, 28, 1235, 10.1038/sj.npp.1300150 Brühlmann, 2001, Coumarin derivatives as dual inhibitors of acetylcholinesterase and momoamine oxidase, J Med Chem, 44, 3195, 10.1021/jm010894d Buckingham, 2009, Nicotinic acetylcholine receptor signalling: roles in Alzheimer's disease and amyloid neuroprotection, Pharmacol Rev, 61, 39, 10.1124/pr.108.000562 Calixto, 2003, Anti-inflammatory compounds of plant origin, Planta Med, 69, 973 Capone, 1999, Effects of the novel acetylcholinesterase inhibitor N-octyl-1,2,3, 4-tetrahydro-9-aminoacridine on locomotor activity and avoidance learning in mice, Neurobiol Learn Mem, 71, 301, 10.1006/nlme.1998.3883 Capron, 2006, The characteristics of LTP in hippocampal slices are dependent on slice-recovery conditions, Learn Mem, 13, 271, 10.1101/lm.135406 Carlsson, 1989, Marked locomotor stimulation in monoamine-depleted mice following treatment with atropine in combination with clonidine, J Neural Transm Park Dis Dement Sect, 1, 317, 10.1007/BF02263486 Chimenti, 2004, Inhibition of monoamine oxidases by coumarin-3-acyl derivatives: biological activity and computational study, Bioorg Med Chem Lett, 14, 3697, 10.1016/j.bmcl.2004.05.010 Delatour, 1996, Prelimbic cortex specific lesions disrupt delayed-variable response tasks in the rat, Behav Neurosci, 110, 1282, 10.1037/0735-7044.110.6.1282 Dember, 1990, The search for cues and motives, 73 Desgranges, 1996, Memory disorders in Alzheimer's disease and the organization of human memory, Cortex, 32, 387, 10.1016/S0010-9452(96)80001-3 Dodart, 1997, Scopolamine-induced deficits in a two-trial object recognition task in mice, Neuroreport, 8, 1173, 10.1097/00001756-199703240-00023 Duffy, 2009, Spatial and intracellular relationships between the alpha7 nicotinic acetylcholine receptor and the vesicular acetylcholine transporter in the prefrontal cortex of rat and mouse, Neuroscience, 161, 1091, 10.1016/j.neuroscience.2009.04.024 Egger, 1973, Ontogenetic aspects of central cholinergic involvement in spontaneous alternation behavior, Dev Psychobiol, 6, 289, 10.1002/dev.420060402 Einat, 1995, Perseveration without hyperlocomotion in a spontaneous alternation task in rats sensitized to the dopamine agonist quinpirole, Physiol Behav, 57, 55, 10.1016/0031-9384(94)00209-N Ennaceur, 1988, A new one-trial test for neurobiological studies of memory in rats, Behav Brain Res, 31, 47, 10.1016/0166-4328(88)90157-X Farah, 1992, Pharmacologically active phenylpropanoids from senra incana, Planta Med, 58, 14, 10.1055/s-2006-961380 Fernando, 1986, The role of dopamine in behavioral supersensitivity to muscarinic antagonists following cholinesterase inhibition, Life Sci, 39, 2169, 10.1016/0024-3205(86)90393-0 Flicker, 1985, Cognitive function in normal aging and early dementia, 2 Franklin, 1997 Froc, 2003, Reduced synaptic plasticity in the lateral perforant path input to the dentate gyrus of aged C57BL/6 mice, J Neurophysiol, 90, 32, 10.1152/jn.00105.2003 Fujii, 2001, Acute and chronic nicotine exposure reverse age-related declines in the induction of long-term potentiation in the rat hippocampus, Brain Res, 894, 347, 10.1016/S0006-8993(01)02057-1 Fujii, 2000, Inactivation of α7 ACh receptors and activation of non-α7 ACh receptors both contribute to long-term potentiation induction in the hippocampal CA1 region, Neurosci Lett, 286, 134, 10.1016/S0304-3940(00)01076-4 Fujioka, 1999, Antiproliferative constituents from umbelliferae plants, Chem Pharm Bull, 47, 96, 10.1248/cpb.47.96 Gainotti, 1998, Sensitivity and specificity of some neuropsychological markers of Alzheimer dementia, Alzheimer Dis Assoc Disord, 12, 152, 10.1097/00002093-199809000-00006 Garcia-Sanz, 2001, Superfusion of synaptosomes to study presynaptic mechanisms involved in neurotransmitter release from rat brain, Brain Res Brain Res Protoc, 7, 94, 10.1016/S1385-299X(00)00058-1 Ge, 2005, Nicotinic acetylcholine receptors at glutamate synapses facilitate long-term depression or potentiation, J Neurosci, 25, 6084, 10.1523/JNEUROSCI.0542-05.2005 Gerlai, 1998, A new continuous alternation task in T-maze detects hippocampal dysfunction in mice, Behav Brain Res, 95, 91, 10.1016/S0166-4328(97)00214-3 Hoerr, 2002, Ensaculin (KA-672 HCl): a multitransmitter approach to dementia treatment, CNS Drug Rev, 8, 143, 10.1111/j.1527-3458.2002.tb00220.x Hornick, 2008, Extracts and constituents of leontopodium alpinum enhance cholinergic transmission: brain ACh increasing and memory improving properties, Biochem Pharmacol, 76, 236, 10.1016/j.bcp.2008.04.015 Itoh, 1993, Dopaminergic involvement in the improving effects of dynorphin A-(1–13) on scopolamine-induced impairment of alternation performance, Eur J Pharmacol, 241, 99, 10.1016/0014-2999(93)90938-E Jones, 1999, Nicotinic receptors in the brain: correlating physiology with function, Trends Neurosci, 22, 555, 10.1016/S0166-2236(99)01471-X Kang, 1999, Scopoletin: an inducible nitric oxide synthesis inhibitory active constituent from artemisia feddei, Planta Med, 65, 400, 10.1055/s-1999-14014 Kim, 2007, Nodakenin, a coumarin compound, ameliorates scopolamine-induced memory disruption in mice, Life Sci, 80, 1944, 10.1016/j.lfs.2007.02.023 Kim, 1999, In vitro inducible nitric oxide synthesis inhibitory active constituents from fraxinus rhynchophylla, Planta Med, 65, 656, 10.1055/s-2006-960840 Kokkinidis, 1976, Interaction between cholinergic and catecholaminergic agents in a spontaneous alternation task, Psychopharmacology, 48, 261, 10.1007/BF00496859 Lagostena, 2008, The partial alpha7 nicotine acetylcholine receptor agonist S 24795 enhances long-term potentiation at CA3-CA1 synapses in the adult mouse hippocampus, Neuropharmacology, 54, 676, 10.1016/j.neuropharm.2007.11.016 Lee, 2003, Associative and recognition memory for novel objects in dementia: implications for diagnosis, Eur J Neurosci, 18, 1660, 10.1046/j.1460-9568.2003.02883.x Lilienfeld, 2000, Galantamine: additional benefits to patients with Alzheimer's disease, Dement Geriatr Cogn Disord, 11, 19, 10.1159/000051228 Lin, 2008, Structure-activity relationship of coumarin derivatives on xanthine oxidase-inhibiting and free radical-scavenging activities, Biochem Pharmacol, 75, 1416, 10.1016/j.bcp.2007.11.023 Liu, 2007, Dissecting the signaling pathway of nicotine-mediated neuroprotection in a mouse Alzheimer disease model, FASEB J, 21, 61, 10.1096/fj.06-5841com Lynch, 2002, Memory enhancement: the search for mechanism-based drugs, Nat Neurosci, 5, 1035, 10.1038/nn935 Maelicke, 2000, Allosterically potentiating ligands of nicotinic acetylcholine receptors as a treatment strategy for Alzheimer's disease, Behav Brain Res, 113, 199, 10.1016/S0166-4328(00)00214-X Mann, 2003, Novel modulatory mechanisms reveled by the sustained application of nicotine in the guinea-pig hippocampus in vitro, J Physiol, 551, 539, 10.1113/jphysiol.2003.045492 Marchi, 1999, Nicotinic receptors modulating ACh release in rat cortical synaptosomes: role of Ca2+ions and their function and desesnitization, Neurochem Int, 34, 319, 10.1016/S0197-0186(99)00015-7 Marchi, 1983, Is acetylcholine release from striatal nerve endings regulated by muscarinic autoreceptors?, Eur J Pharmacol, 91, 63, 10.1016/0014-2999(83)90362-X Martin, 2002, New life in an old idea: the synaptic plasticity and memory hypothesis revisited, Hippocampus, 12, 609, 10.1002/hipo.10107 Matsuyama, 2003, Epibatidine induces long-term potentiation (LTP) via activation of alpha4beta2 nicotinicacetylcholine receptors (nAChRs) in vivo in the intact mouse dentate gyrus: both alpha7 and alpha4beta2 nAChRs essential to nicotinic LTP, J Pharmacol Sci, 93, 180, 10.1254/jphs.93.180 McFarland, 1989, Effects of scopolamine, d-amphetamine, and apomorphine on alternation and position biases, Pharmacol Biochem Behav, 32, 723, 10.1016/0091-3057(89)90024-5 Meyers, 1964, The effect of cholinergic drugs on spontaneous alternation in rats, Arch Int Pharmacodyn, 150, 3 Moriguchi, 2009, Galantamine enhancement of long-term potentiation is mediated by calcium/calmodulin-dependent protein kinase II and protein kinase C activation, Hippocampus, 19, 844, 10.1002/hipo.20572 Muschietti, 2001, Phenolic compounds with anti-inflammatory activity from eupatorium buniifolium, Planta Med, 67, 743, 10.1055/s-2001-18355 Nakauchi, 2007, Nicotine gates long-term potentiation in the hipppocampal CA1 region via the activation of α2* nicotinic ACh receptors, Eur J Neurosci, 25, 2666, 10.1111/j.1460-9568.2007.05513.x Newhouse, 2001, Nicotinic treatment of Alzheimer's disease, Biol Psychiatry, 49, 268, 10.1016/S0006-3223(00)01069-6 Newman, 1999, The prevalence of depression in Alzheimer's disease and vascular dementia in a population sample, J Affect Disord, 52, 169, 10.1016/S0165-0327(98)00070-6 Onor, 2007, Rivastigmine in the treatment of Alzheimer's disease: an update, Clin Interv Aging, 2, 17, 10.2147/ciia.2007.2.1.17 Palmer, 1988, Possible neurotransmitter basis of behavioral changes in Alzheimer's disease, Ann Neurol, 23, 616, 10.1002/ana.410230616 Papke, 2008, Extending the analysis of nicotinic receptor antagonists with the study of α6 nicotinic receptor subunit chimeras, Neuropharmacology, 54, 1189, 10.1016/j.neuropharm.2008.03.010 Petersen, 2000, Memory and MRI-based hippocampal volumes in aging and AD, Neurology, 54, 581, 10.1212/WNL.54.3.581 Pichat, 2007, SSR180711, a novel selective alpha7 nicotinic receptor partial agonist: (II) efficacy in experimental models predictive of activity against cognitive symptoms of schizophrenia, Neuropsychopharmacology, 32, 17, 10.1038/sj.npp.1301188 Prut, 2003, The open field as a paradigm to measure the effects of drugs on anxiety-like behaviors: a review, Eur J Pharmacol, 463, 3, 10.1016/S0014-2999(03)01272-X Puma, 1999, Nicotine improves memory in an object recognition task in rats, Eur Neuropsychopharmacol, 9, 323, 10.1016/S0924-977X(99)00002-4 Qi, 2007, Neurochem Int, 51, 377, 10.1016/j.neuint.2007.04.002 Raiteri, 2000, Synaptosomes still viable after 25 years of superfusion, Neurochem Res, 25, 1265, 10.1023/A:1007648229795 Raiteri, 1974, A simple apparatus for studying the release of neurotransmitters from synaptosomes, Eur J Pharmacol, 25, 411, 10.1016/0014-2999(74)90272-6 Remy, 2005, Verbal episodic memory impairment in Alzheimer's disease: a combined structural and functional MRI study, Neuroimage, 25, 253, 10.1016/j.neuroimage.2004.10.045 Rispoli, 2006, Choline pivaloyl ester strengthened the benefit effects of tacrine and galantamine on electroencephalographic and cognitive performances in nucleus basalis magnocellularis-lesioned and aged rats, Pharmacol Biochem Behav, 84, 453, 10.1016/j.pbb.2006.06.009 Rollinger, 2004, Acetylcholinesterase inhibitory activity of scopolin and scopoletin discovered by virtual screening of natural products, J Med Chem, 47, 6248, 10.1021/jm049655r Roman, 2004, Potentiation effects of (+/-)huprine X, a new acetylcholinesterase inhibitor, on nicotinic receptors in rat cortical synaptosomes, Neuropharmacology, 46, 95, 10.1016/j.neuropharm.2003.08.005 Roncarati, 2009, Procognitive and neuroprotective activity of a novel alpha7 nicotinic acetylcholine receptor agonist for treatment of neurodegenerative and cognitive disorders, J Pharmacol Exp Ther, 329, 459, 10.1124/jpet.108.150094 Rosato-Siri, 2006, Nicotine-induced enhancement of synaptic plasticity at CA3-CA1 synapses requires GABAergic interneurons in adult anti-NGF mice, J Physiol, 576, 361, 10.1113/jphysiol.2006.114587 Sambeth, 2007, Cholinergic drugs affect novel object recognition in rats: relation with hippocampal EEG?, Eur J Pharmacol, 572, 151, 10.1016/j.ejphar.2007.06.018 Samochocki, 2003, Galantamine is an allosterically potentiating ligand of neuronal nicotinic but not of muscarinic acetylcholine receptors, J Pharmacol Exp Ther, 305, 1024, 10.1124/jpet.102.045773 Schoenmakers, 2009, Can pharmacological treatment of behavioural disturbances in elderly patients with dementia lower the burden of their family caregiver?, J Fam Pract, 26, 279, 10.1093/fampra/cmp024 Scott, 2000, Galantamine: a review of its use in Alzheimer's disease, Drugs, 60, 1095, 10.2165/00003495-200060050-00008 Shaw, 2003, Antioxidant properties of scopoletin isolated from sinomonium acutum, Phytother Res, 17, 823, 10.1002/ptr.1170 Shen, 2005, Synthesis and biological evaluation of functionalized coumarins as acetylcholinesterase inhibitors, Eur J Med Chem, 40, 1307, 10.1016/j.ejmech.2005.07.014 Sliwinski, 2004, Pregnenolone sulfate enhances long-term potentiation in CA1 in rat hippocampus slices through the modulation of N-methyl-d-aspartate receptors, J Neurosci Res, 78, 691, 10.1002/jnr.20332 Sonnen, 2008, Free radical-mediated damage to brain in Alzheimer's disease and its transgenic mouse models, Free Radic Biol Med, 45, 219, 10.1016/j.freeradbiomed.2008.04.022 Sonnen, 2009, Free radical damage to cerebral cortex in Alzheimer's disease, microvascular brain injury, and smoking, Ann Neurol, 65, 226, 10.1002/ana.21508 Spowart-Manning, 2004, The T-maze continuous alternation task for assessing the effects of putative cognition enhancers in the mouse, Behav Brain Res, 151, 37, 10.1016/j.bbr.2003.08.004 Stone, 1992, Glucose attenuation of scopolamine- and age-related deficits in spontaneous alternation behaviour and regional [3H]2-deoxy-glucose uptake in mice, Psychobiology, 20, 270, 10.3758/BF03332059 Storch, 1995, Physostigmine, galanthamine and codeine act as “noncompetitive nicotinic receptor agonists” on clonal rat pheochromocytoma cells, Eur J Pharmacol, 290, 207, 10.1016/0922-4106(95)00080-1 Stuppner, 2005 Syenkiewicz-Jarosz, 2000, The effects of physostigmine and cholinergic receptor ligands on novelty-induced neophobia, J Neural Transm, 107, 1403, 10.1007/s007020070004 Szerb, 1977, Release of [3H]acetylcholine from rat hippocampal slices: effect of septal lesions and graded concentrations of muscarinic agonists and antagonists, Brain Res, 128, 285, 10.1016/0006-8993(77)90995-7 Timmermann, 2007, An allosteric modulator of the alpha7 nicotinic acetylcholine receptor possessing cognition-enhancing properties in vivo, J Pharmacol Exp Ther, 323, 294, 10.1124/jpet.107.120436 Tiyagi, 2005, Synthesis of novel amino and acetyl-amino-4-methylcoumarins and evaluation of their antioxidant activity, Eur J Med Chem, 40, 413, 10.1016/j.ejmech.2004.09.002 Toda, 2002, Inhibitory effects of phenylpropanoid metabolites on copper-induced protein oxidative modification of mice brain homogenate, in vitro, Biol Trace Elem Res, 85, 183, 10.1385/BTER:85:2:183 Tzavara, 2003, Dysregulated hippocampal acetylcholine neurotransmission and impaired cognition in M2, M4 and M2/M4 muscarinic receptor knockout mice, Mol Psychiatry, 8, 673, 10.1038/sj.mp.4001270 Ukai, 1995, Cholinergic receptor antagonists inhibit pirenzepine-induced dysfunction of spontaneous alternation performance in the mouse, Gen Pharmacol, 26, 1529, 10.1016/0306-3623(95)00038-0 Wang, 2007, The allosteric potentiation of nicotinic acetylcholine receptors by galantamine ameliorates the cognitive dysfunction in beta amyloid25-35 i.c.v.-injected mice: involvement of dopaminergic systems, Neuropsychopharmacology, 32, 1261, 10.1038/sj.npp.1301256 Willig, 1987, Short-term memory, exploration and locomotor activity in aged rats, Neurobiol Aging, 8, 393, 10.1016/0197-4580(87)90033-9 Wishka, 2006, Discovery of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]furo[2,3-c]pyridine-5-carboxamide, an agonist of the alpha7 nicotinic acetylcholine receptor, for the potential treatment of cognitive deficits in schizophrenia: synthesis and structure-activity relationship, J Med Chem, 49, 4425, 10.1021/jm0602413 Woodruff-Pak, 2002, Neuronal nicotinic acetylcholine receptors: involvement in Alzheimer's disease and schizophrenia, Behav Cogn Neurosci Rev, 1, 5, 10.1177/1534582302001001002 Yun, 2001, Coumarins with monoamine oxidase inhibitory activity and antioxidative coumarino-lignans from hibiscus syriacus, J Nat Prod, 64, 1238, 10.1021/np0100946 Zhang, 2002, Characterization of central inhibitory muscarinic autoreceptors by the use of muscarinic acetylcholine receptor knock-out mice, J Neurosci, 22, 1709, 10.1523/JNEUROSCI.22-05-01709.2002 Zhao, 2009, Natural antioxidants protect neurons in Alzheimer's disease and Parkinson's disease, Neurochem Res, 34, 630, 10.1007/s11064-008-9900-9