An in silico guided identification of nAChR agonists from Withania somnifera

References

• Asthana R, Raina MK. 1989. Pharmacology of Withania somnifera (L.) Dunal-a review. Indian Drugs. 26:199–205.
   Google Scholar
• Atta-ur-Rahman, Abbas S, Dur-e-Shahwar, Jamal SA, Choudhary MI. 1993. New withanolides from Withania sp. J Nat Prod. 56:1000–1006. doi: 10.1021/np50097a003
   Web of Science ®Google Scholar
• Atta-ur-rahman, Jamal SA, Choudhary MI, Asif E. 1991. Two withanolides from Withania somnifera. Phytochemistry. 30:3824–3825. doi: 10.1016/0031-9422(91)80125-K
   Web of Science ®Google Scholar
• Bartus RT, Dean RL, Beer B, Lippa AS. 1982. The cholinergic hypothesis of geriatric memory dysfunction. Science. 217:408–417. doi: 10.1126/science.7046051
   PubMed Web of Science ®Google Scholar
• Bhattacharya SK, Kumar A, Ghosal S. 1995. Effects of glycowithanolides from Withania somnifera on an animal model of Alzheimer’s disease and perturbed central cholinergic markers of cognition in rats. Phytother Res. 9:110–113. doi: 10.1002/ptr.2650090206
   Web of Science ®Google Scholar
• Bhattacharya SK, Satyan KS, Ghosal S. 1997. Antioxidant activity of glycowithanolides from Withania somnifera. Indian J Exp Biol. 35:236–239.
   PubMedGoogle Scholar
• Brams M, Pandya A, Kuzmin D, Van Elk R, Krijnen L, Yakel JL, Tsetlin V, Smit AB, Ulens C. 2011. A structural and mutagenic blueprint for molecular recognition of strychnine and d-tubocurarine by different cys-loop receptors. Plos ONE Biology. 9:01034.
   Google Scholar
• Brejc K, van Dijk WJ, Klaassen RV, Schuurmans M, van Der Oost J, Smit AB, Sixma TK. 2001. Crystal structure of an ACh-binding protein reveals the ligand-binding domain of nicotinic receptors. Nature. 411:269–276. doi: 10.1038/35077011
   PubMed Web of Science ®Google Scholar
• Celie PHN, van Rossum-Fikkert SE, van Dijk WJ, Brejc K, Smit AB, Sixma TK. 2004. Nicotine and carbamylcholine binding to nicotinic acetylcholine receptors as studied in AChBP crystal structures. Neuron. 41:907–914. doi: 10.1016/S0896-6273(04)00115-1
   PubMed Web of Science ®Google Scholar
• Choudary MI, Abbas S, Jamal AS, Atta-ur-Rahman E. 1996. Withania somnifera – a source of exotic withanolides. Heterocycles. 42:555–563. doi: 10.3987/COM-94-6935
   Web of Science ®Google Scholar
• Coyle JT, Price DL, Delong MR. 1983. Alzheimer’s disease: a disorder of cortical cholinergic innervation. Science. 219:1184–1190. doi: 10.1126/science.6338589
   PubMed Web of Science ®Google Scholar
• D’Andrea MR, Nagele RG. 2006. Targeting the alpha 7 nicotinic acetylcholine receptor to reduce amyloid accumulations in Alzheimer’s disease pyramidal neurons. Curr Pharm Des. 12:677–684. doi: 10.2174/138161206775474224
   PubMed Web of Science ®Google Scholar
• Dani JA, Bertrand D. 2007. Nicotinic acetylcholine receptors and nicotinic cholinergic mechanisms of the central nervous system. Annu Rev Pharmacol. 47:699–729. doi: 10.1146/annurev.pharmtox.47.120505.105214
   Google Scholar
• Davies P, Feisullin S. 1981. Postmortem stability of -bungarotoxin binding sites in mouse and human brain. Brain Res. 216:449–454. doi: 10.1016/0006-8993(81)90148-7
   PubMed Web of Science ®Google Scholar
• Davies P, Maloney AJ. 1976. Selective loss of central cholinergic neurons in Alzheimer’s disease. Lancet. 2:1403–1404. doi: 10.1016/S0140-6736(76)91936-X
   PubMed Web of Science ®Google Scholar
• Dhuley JN. 2001. Retracted: nootropic-like effect of ashwagandha (Withania somnifera L.) in mice. Phytother Res. 15:524–528. doi: 10.1002/ptr.874
   PubMed Web of Science ®Google Scholar
• Elsakka M, Grigorescu E, Stanescu U. 1990. New data referring to chemistry of Withania somnifera species. Revista medico-chirurgicala a Societatii de Medici si Naturalisti din Iasi. 94:385–387.
   PubMedGoogle Scholar
• Fisher A. 2008. Cholinergic treatments with emphasis on M1 muscarinic agonists as potential disease-modifying agents for Alzheimer’s disease. Neurotherapeutics. 5:433–442. doi: 10.1016/j.nurt.2008.05.002
   PubMed Web of Science ®Google Scholar
• Gotti C, Clementi F. 2004. Neuronal nicotinic receptors: from structure to pathology. Prog Neurobiol. 6:363–396. doi: 10.1016/j.pneurobio.2004.09.006
   Web of Science ®Google Scholar
• Grimster NP, Stump B, Fotsing JR, Weide T, Talley TT, Yamauchi JG, Nemecz Kim C, Ho KY, Sharpless KB, Taylor P, Fokin VV. 2012. Generation of candidate ligands for nicotinic acetylcholine receptors via in situ click chemistry with a soluble acetylcholine binding protein template. J Am Chem Soc. 134:6732–6740. doi: 10.1021/ja3001858
   PubMed Web of Science ®Google Scholar
• Gupta GL, Rana AC. 2007. Withania somnifera (Ashwagandha): a review. Pharmacognosy Review. 1:129–136.
   Google Scholar
• Gupta SK, Dua A, Vohra BP. 2003. Withania somnifera (Ashwagandha) attenuates antioxidant defense in aged spinal cord and inhibits copper induced lipid peroxidation and protein oxidative modifications. Drug Metabol Drug Interact. 19:211–222. doi: 10.1515/DMDI.2003.19.3.211
   PubMedGoogle Scholar
• Hansen SB, Sulzenbacher G, Huxford T, Marchot P, Taylor P, Bourne Y. 2005. Structures of Aplysia AChBP complexes with nicotinic agonists and antagonists reveal distinctive binding interfaces and conformations. The EMBO Journal. 24:3635–3646. doi: 10.1038/sj.emboj.7600828
   PubMed Web of Science ®Google Scholar
• Hansen SB, Talley TT, Radic Z, Taylor P. 2004. Structural and ligand recognition characteristics of an acetylcholine-binding protein from Aplysia californica. J Biol Chem. 279:24197–24202. doi: 10.1074/jbc.M402452200
   PubMed Web of Science ®Google Scholar
• Heinrich M, Teoh HL. 2004. Galanthamine from snowdrop – the development of a modern drug against Alzheimer’s disease from local Caucasian knowledge. J Ethnopharmacol. 92:147–162. doi: 10.1016/j.jep.2004.02.012
   PubMed Web of Science ®Google Scholar
• Howes MJ, Perry E. 2011. The role of phytochemicals in the treatment and prevention of dementia. Drug Aging. 28:439–468. doi: 10.2165/11591310-000000000-00000
   PubMed Web of Science ®Google Scholar
• Ihara M, Okajima T, Yamashita A, Oda T, Hirata K, Nishiwaki H, Morimoto T, Akamatsu M, Ashikawa Y, Kuroda S, et al. 2008. Crystal structures of Lymnaea stagnalis AChBP in complex with neonicotinoid insecticides imidacloprid and clothianidin. Invertebr Neurosci. 8:71–81. doi: 10.1007/s10158-008-0069-3
   PubMedGoogle Scholar
• Itier V, Bertrand D. 2001. Neuronal nicotinic receptors: from protein structure to function. FEBS Letters. 504:118–125. doi: 10.1016/S0014-5793(01)02702-8
   PubMed Web of Science ®Google Scholar
• Jayaprakasam B, Padmanabhan K, Nair MG. 2010. Withanamides in Withania somnifera fruit protect PC-12 cells from beta-amyloid responsible for Alzheimer’s disease. Phytother Res. 24:859–863.
   PubMed Web of Science ®Google Scholar
• Jensen AA, Frolund B, Liljefors T, Krogsgaard-Larsen P. 2005. Neuronal nicotinic acetylcholine receptors: structural revelations, target identifications, and therapeutic inspirations. J Med Chem. 48:4707–4745. doi: 10.1021/jm040219e
   Web of Science ®Google Scholar
• Kapoor LD. 2001. Handbook of Ayurvedic medicinal plants. London: CRC Press; p. 337–338.
   Google Scholar
• Kar S, Slowikowski SP, Westaway D, Mount HT. 2004. Interactions between beta-amyloid and central cholinergic neurons: implications for Alzheimer’s disease. J. Psychiatry Neurosci. 29:427–441.
   PubMed Web of Science ®Google Scholar
• Kataria H, Wadhwa R, Kaul SC, Kaur G. 2012. Water extract from the leaves of Withania somnifera protect RA differentiated C6 and IMR-32 cells against Glutamate-induced excitotoxicity. PLoS ONE. 7:e37080. 10.1371/journal.pone.0037080. doi: 10.1371/journal.pone.0037080
   Google Scholar
• Kem WR. 2000. The brain nicotinic receptor may be an important therapeutic target for the treatment of Alzheimer’s disease: studies with DMXBA (GTS-21). Behavioural Brain Research. 113:169–181. doi: 10.1016/S0166-4328(00)00211-4
   PubMed Web of Science ®Google Scholar
• Krall WJ, Sramek JJ, Cutler NR. 1999. Cholinesterase inhibitors: a therapeutic strategy for Alzheimer disease. Ann Pharmacother. 33:441–450. doi: 10.1345/aph.18211
   PubMed Web of Science ®Google Scholar
• Kuboyama T, Tohda C, Komatsu K. 2005. Neuritic regeneration and synaptic reconstruction induced by withanolide A. Br J Pharmacol. 144:961–971. doi: 10.1038/sj.bjp.0706122
   PubMed Web of Science ®Google Scholar
• Kumar S, Harris RJ, Seal CJ, Okello EJ. 2012. An aqueous extract of Withania somnifera root inhibits amyloid β fibril formation in vitro. Phytother Res. 26:113–117. doi: 10.1002/ptr.3512
   PubMed Web of Science ®Google Scholar
• Kumar V. 2006. Potential medicinal plants for CNS disorders: an overview. Phytother Res. 20:1023–1035. doi: 10.1002/ptr.1970
   PubMed Web of Science ®Google Scholar
• Li SX, Huang S, Bren N, Noridomi K, Dellisanti CD, Sine SM, Chen L. 2011. Ligand-binding domain of an alpha 7-nicotinic receptor chimera and its complex with agonist. Nature Neurosci. 14:1253–1259. doi: 10.1038/nn.2908
   PubMed Web of Science ®Google Scholar
• Lindstrom JM. 2003. Nicotinic acetylcholine receptors of muscles and nerves: comparison of their structures, functional roles, and vulnerability to pathology. Ann N Y Acad Sci. 998:41–52. doi: 10.1196/annals.1254.007
   PubMed Web of Science ®Google Scholar
• Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. 2001. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev. 46:3–26. doi: 10.1016/S0169-409X(00)00129-0
   PubMed Web of Science ®Google Scholar
• Mahnir V, Lin B, Prokai-Tatrai K, Kem WR. 1998. Pharmacokinetics and urinary excretion of DMXBA (GTS-21), a compound enhancing cognition. Biopharm Drug Disp. 19:147–151. doi: 10.1002/(SICI)1099-081X(199804)19:3<147::AID-BDD77>3.0.CO;2-9
   PubMed Web of Science ®Google Scholar
• Martin LF, Kem WR, Freedman R. 2004. Alpha-7 nicotinic receptor agonists: potential new candidates for the treatment of schizophrenia. Psychopharmacology. 174:54–64. doi: 10.1007/s00213-003-1750-1
   PubMed Web of Science ®Google Scholar
• McKay BE, Placzek AN, Dani JA. 2007. Regulation of synaptic transmission and plasticity by neuronal nicotinic acetylcholine receptors. Biochem Pharmacol. 74:1120–1133. doi: 10.1016/j.bcp.2007.07.001
   PubMed Web of Science ®Google Scholar
• Meyer EM, King MA, Meyers C. 1998. Neuroprotective effects of 2,4-dimethoxybenzylidene anabaseine (DMXB) and tetrahydroaminoacridine (THA) in neocortices of nucleus basalis lesioned rats. Brain Res. 768:49–56. doi: 10.1016/S0006-8993(97)00536-2
   Web of Science ®Google Scholar
• Miroslav P. 2012. Alpha7 nicotinic acetylcholine receptor is a target in pharmacology and toxicology. Int J Mol Sci. 13:2219–2238. doi: 10.3390/ijms13022219
   PubMed Web of Science ®Google Scholar
• Pajouhesh H, Lenz GR. 2005. Medicinal chemical properties of successful central nervous system drugs. NeuroRx. 2:541–553. doi: 10.1602/neurorx.2.4.541
   PubMedGoogle Scholar
• Paterson D, Nordberg A. 2000. Neuronal nicotinic receptors in the human brain. Prog Neurobiol. 61:75–111. doi: 10.1016/S0301-0082(99)00045-3
   PubMed Web of Science ®Google Scholar
• Rastogi RP, Mehrotra BN. 1998. Compendium of Indian Medicinal Plants. New Delhi: Central Drug Research Institute.
   Google Scholar
• Ringman JM, Frautschy SA, Cole GM, Masterman DL, Cummings JL. 2005. A potential role of the curry spice curcumin in Alzheimer’s disease. Curr Alzheimer Res. 2:131–136. doi: 10.2174/1567205053585882
   PubMedGoogle Scholar
• Rosini M, Andrisano V, Bartolini M, Bolognesi ML, Hrelia P, Minarini A, Tarozzi A, Melchiorre C. 2005. Rational approach to discover multipotent anti-Alzheimer drugs. J. Med Chem. 48:360–363. doi: 10.1021/jm049112h
   PubMed Web of Science ®Google Scholar
• Russo A, Izzo AA, Cardile V, Borrelli F, Vanella A. 2001. Indian medicinal plants as antiradicals and DNA cleavage protectors. Phytomedicine. 8:125–132. doi: 10.1078/0944-7113-00021
   PubMed Web of Science ®Google Scholar
• Ryan EH, Gerlind S, Jianxin S, Todd TT, Sandrine C, William RK, Palmer T, Pascale M, Yves B. 2009. Structural determinants for interaction of partial agonists with acetylcholine binding protein and neuronal nicotinic acetylcholine receptor. EMBO Journal. 28:3040–3051. doi: 10.1038/emboj.2009.227
   PubMed Web of Science ®Google Scholar
• Sala F, Nistri A, Criado M. 2008. Nicotinic acetylcholine receptors of adrenal chromaffin cells. Acta Physiologica. 192:203–212. doi: 10.1111/j.1748-1716.2007.01804.x
   PubMed Web of Science ®Google Scholar
• Schliebs R, Liebmann A, Bhattacharya SK, Kumar A, Ghosal S, Bigl V. 1997. Systemic administration of defined extracts from Withania somnifera (Indian Ginseng) and Shilajit differentially affects cholinergic but not glutamatergic and GABAergic markers in rat brain. Neurochem Int. 30:181–190. doi: 10.1016/S0197-0186(96)00025-3
   PubMed Web of Science ®Google Scholar
• Scott BH, Gerlind S, Tom H, Pascale M, Palmer T, Yves B. 2005. Structures of Aplysia AChBP complexes with nicotinic agonists and antagonists reveal distinctive binding interfaces and conformations. The EMBO Journal. 24:3635–3646. doi: 10.1038/sj.emboj.7600828
   PubMed Web of Science ®Google Scholar
• Scott BH, Palmer T. 2007. Galanthamine and non-competitive inhibitor binding to ACh-binding protein: evidence for a binding site on non -subunit interfaces of heteromeric neuronal nicotinic receptors. J Mol Biol. 369:895–901. doi: 10.1016/j.jmb.2007.03.067
   PubMed Web of Science ®Google Scholar
• Selkoe D. 2001. Alzheimer’s disease: genes, proteins, and therapy. Physiol Rev. 81:741–766.
   PubMed Web of Science ®Google Scholar
• Shah ZA, Nada SE, Dore S. 2011. Heme oxygenase 1, beneficial role in permanent ischemic stroke and in Gingko biloba (EGb 761) neuroprotection. Neuroscience. 180:248–255. doi: 10.1016/j.neuroscience.2011.02.031
   PubMed Web of Science ®Google Scholar
• Singh S, Kumar S. 1999. Withania somnifera: the Indian ginseng Ashwagandha (Report). Lucknow, India: Central Institute of Medicinal and Aromatic Plants, 131–201.
   Google Scholar
• Small DH, Fodero LR. 2002. Cholinergic regulation of synaptic plasticity as a therapeutic target in Alzheimer’s disease. J Alzheimers Dis. 4:349–355.
   PubMedGoogle Scholar
• Smit AB, Syed NI, Schaap D, van Minnen J, Klumperman J, Kits KS, Lodder H, van der Schors RC, van Elk R, Sorgedrager B, et al. 2001. A glia-derived acetylcholine-binding protein that modulates synaptic transmission. Nature. 411:261–268. doi: 10.1038/35077000
   PubMed Web of Science ®Google Scholar
• Sugaya K, Giacobini E, Chiappinelli VA. 1990. Nicotinic acetylcholine receptor subtypes in human frontal cortex; changes in Alzheimer’s disease. J Neurosci Res. 27:349–359. doi: 10.1002/jnr.490270314
   PubMed Web of Science ®Google Scholar
• Todd TT, Michal H, Ryan EH, Zoran R, Motohiro T, John EC, Palmer T. 2008. Atomic interactions of neonicotinoid agonists with AChBP: molecular recognition of the distinctive electronegative pharmacophore. Proc Natl Acad Sci USA. 105:7606–7611. doi: 10.1073/pnas.0802197105
   PubMed Web of Science ®Google Scholar
• Tohda C, Kuboyama T, Komatsu K. 2005. Search for natural products related to regeneration of the neuronal network. Neurosignals. 14:34–45. doi: 10.1159/000085384
   PubMed Web of Science ®Google Scholar
• Ulens C, Hogg RC, Celie PH, Bertrand D, Tsetlin V, Smit AB, Sixma TK. 2006. Structural determinants of selective alpha-conotoxin binding to a nicotinic acetylcholine receptor homolog AChBP. Proc Natl Acad Sci USA. 103:3615–3620. doi: 10.1073/pnas.0507889103
   PubMed Web of Science ®Google Scholar
• Wevers A, Schröder H. 1999. Nicotinic acetylcholine receptors in Alzheimer’s disease. J Alzheimers Dis. 1:207–219.
   PubMedGoogle Scholar
• Wu PF, Zhang Z, Wang F, Chen JG. 2010. Natural compounds from traditional medicinal herbs in the treatment of cerebral ischemia/reperfusion injury. Acta Pharmacol Sin. 31:1523–1531. doi: 10.1038/aps.2010.186
   PubMed Web of Science ®Google Scholar
• Yves B, Zoran R, Rómulo A, Todd TT, Evelyne B, Denis S, Palmer T, Jordi M, Pascale M. 2010. Structural determinants in phycotoxins and AChBP conferring high affinity binding and nicotinic AChR antagonism. Proc Natl Acad Sci USA. 107:6076–6081. doi: 10.1073/pnas.0912372107
   PubMed Web of Science ®Google Scholar
• Zarei MM, Radcliffe KA, Chen D, Patrick JW, Dani JA. 1999. Distributions of nicotinic acetylcholine receptor alpha7 and beta2 subunits on cultured hippocampal neurons. Neuroscience. 88:755–764. doi: 10.1016/S0306-4522(98)00246-2
   PubMed Web of Science ®Google Scholar