Implication of coumarins towards central nervous system disorders

Pharmacological Research

Volumn 103, Issue , 2016, Pages 188-203

  Skalicka Woźniak, Krystyna ^a   Orhan, Ilkay Erdogan ^b   Cordell, Geoffrey A ^c,d   Nabavi, Seyed Mohammad ^e   Budzyńska, Barbara ^a  

^a MEDICAL UNIVERSITY OF LUBLIN   (Poland)

^b GAZI UNIVERSITY   (Turkey)

^c Natural Products Inc   (United States)

^d UNIVERSITY OF FLORIDA HEALTH   (United States)

^e BAQIYATALLAH UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

Benzodiazepine receptors; Central nervous system; Cholinesterase inhibitors; Coumarins; Monoamine oxidase (MAO) inhibitors; Aminobutyric acid (GABA)

Indexed keywords

4 AMINOBUTYRIC ACID; 4 METHOXY 7 PHENYL 7,8 DIHYDRO[1,3]DIOXOLO[4,5 G]ISOCHROMEN 5 ONE; ANSECULIN; BENZODIAZEPINE RECEPTOR; BERGAPTEN; BYAKANGELICOL; CNIDILIN; COLUMBIANEDIN; COLUMBIANETIN ACETATE; COUMARIN DERIVATIVE; DECURSIN; DECURSINOL; DOPAMINE RECEPTOR; DOPAMINE RECEPTOR STIMULATING AGENT; FRAXETIN; ISOPIMPINELLIN; LACINARTIN; METHOXSALEN; MONOAMINE OXIDASE A INHIBITOR; MONOAMINE OXIDASE B INHIBITOR; OSTHOLE; OSTRUTHOL; OXYPEUCEDANIN; PENTOSALEN; PHELLOPTERIN; PSORALEN; SCOPARONE; SEROTONIN AGONIST; SEROTONIN RECEPTOR; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ALZHEIMER DISEASE; ANXIETY DISORDER; BINDING AFFINITY; CENTRAL NERVOUS SYSTEM DISEASE; DEGENERATIVE DISEASE; DEPRESSION; DRUG EFFICACY; DRUG ISOLATION; DRUG MECHANISM; DRUG RECEPTOR BINDING; DRUG RESEARCH; DRUG STRUCTURE; ENZYME INHIBITOR INTERACTION; EPILEPSY; HUMAN; IC50; MENTAL DISEASE; NEUROPROTECTION; NEUROTOXICITY; NONHUMAN; PARKINSON DISEASE; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; REVIEW; SCHIZOPHRENIA; STRUCTURE ACTIVITY RELATION; ANIMAL; CENTRAL NERVOUS SYSTEM; CENTRAL NERVOUS SYSTEM DISEASES; DRUG EFFECTS; METABOLISM;

ANIMALS; CENTRAL NERVOUS SYSTEM; CENTRAL NERVOUS SYSTEM DISEASES; COUMARINS; HUMANS;

EID: 84949604050     PISSN: 10436618     EISSN: 10961186     Source Type: Journal    
DOI: 10.1016/j.phrs.2015.11.023     Document Type: Review

References (118)

1. A. Lacy, and R. O'Kennedy Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer Curr. Pharm. Design 10 2004 3797 3811
2. C. Kontogiorgis, A. Detsi, and D. Hadjipavlou-Litina Coumarin-based drugs: a patent review (2008 - present) Expert Opin. Ther. Pat. 22 2012 437 454
3. O. Ceska, S.K. Chaudhary, P.J. Warrington, and M.J. Ashwood-Smith Photoactive furocoumarins in fruits of some umbellifers Phytochemistry 26 1987 165 169
4. I.E. Orhan, and H.O. Gulcan Coumarins: auspicious cholinesterase and monoamine oxidase inhibitors Curr. Topics Med. Chem. 15 2015 1673 1682
5. A.M. Holbrook, J.A. Pereira, R. Labiris, H. McDonald, J.D. Douketis, M. Crowther, and P.S. Wells Systematic overview of warfarin and its drug and food interactions Arch. Intern. Med. 165 2005 1095 1106
6. T.J. Walsh, H.C. Standiford, A.C. Reboli, and et al. Randomized double-blinded trial of rifampin with either novobiocin or trimethoprim-sulfamethoxazole against methicillin-resistant Staphylococcus aureus colonization: prevention of antimicrobial resistance and effect of host factors on outcome Antimicrob. Agents Chemother. 37 1993 1334 1342
7. T. Ojala, P. Vuorela, J. Kiviranta, H. Vuorela, and R. Hiltunen A bioassay using Artemia salina for detecting phototoxicity of plant coumarins Planta Med. 65 1999 715 718
8. M. Lüftl, M. Röcken, G. Plewig, and K. Degitz PUVA inhibits DNA replication, but not gene transcription at nonlethal dosages J. Invest. Dermatol. 111 1998 399 405
9. A. Fallarero, P. Oinonen, S. Gupta, P. Blom, A. Galkin, C.G. Mohan, and P.M. Vuorela Inhibition of acetylcholinesterase by coumarins: the case of coumarin 106 Pharmacol. Res. 58 2008 215 221
10. K. Dekermendjian, J. Ai, M. Nielsen, O. Sterner, R. Shan, and M.R. Witt Characterization of the furanocoumarin phellopterin as a rat brain benzodiazepine receptor partial agonist in vitro Neurosci. Lett. 219 1996 151 154
11. A receptor modulators in Xenopus oocytes Fitoterapia 82 2011 434 440
12. A receptor modulating coumarins and furanocoumarins Eur. J. Pharmacol 668 2011 57 64
13. O. Bergendorff, K. Dekermendjian, M. Nielsen, R. Shan, R. Witt, J. Ai, and O. Sterner Furanocoumarins with affinity to brain benzodiazepine receptors in vitro Phytochemistry 44 1997 1121 1124
14. Y. Li, I. Plitzko, J. Zaugg, S. Hering, and M. Hamburger HPLC-based activity profiling for GABAA receptor modulators: a new Dihydroisocoumarin from Haloxylon scoparium J. Nat. Prod. 73 2010 768 770
15. M. Herrera-Ruiz, A. Gonzalez-Carranza, A. Zamilpa, E. Jimenez-Ferrer, M. Huerta-Reyes, and V.M. Navarro-Garcia The standardized extract of Loeselia mexicana possesses anxiolytic activity through the amino butyric acid mechanism J. Ethnopharmacol. 138 2011 261 267
16. J.J. Luszczki, K. Głowniak, and S.J. Czuczwar Time-course and dose-response relationships of imperatorin in the mouse maximal electroshock seizure threshold model Neurosci. Res. 59 2007 18 22
17. S.Y. Choi, E.M. Ahn, M.C. Song, D.W. Kim, J.H. Kang, O.S. Kwon, T.C. Kang, and N.I. Baek In vitro GABA-transaminase inhibitory compounds from the root of Angelica dahurica Phytother. Res. 19 2005 839 845
18. J.J. Luszczki, K. Głowniak, and S.J. Czuczwar Imperatorin enhances the protective activity of conventional antiepileptic drugs against maximal electroshock-induced seizures in mice Eur. J. Pharmacol. 574 2007 133 139
19. J.J. Łuszczki, E. Wojda, G. Raszewski, K. Głowniak, and S.J. Czuczwar Influence of imperatorin on the anticonvulsant activity and acute adverse-effect profile of lamotrigine in maximal electroshock-induced seizures and chimney test in mice Pharmacol. Rep. 60 2008 566 573
20. J.J. Łuszczki, M. Andres-Mach, M. Glensk, and K. Skalicka-Woźniak Anticonvulsant effects of four linear furanocoumarins, bergapten, imperatorin, oxypeucedanin, and xanthotoxin, in the mouse maximal electroshock-induced seizure model: a comparative study Pharmacol. Rep. 62 2010 1231 1236
21. J.P. Stables, and H.J. Kupferberg The NIH anticonvulsant drug development (ADD) program: preclinical anticonvulsant screening project G. Avanzini, G. Regesta, P. Tanganelli, M. Avoli, Molecular and Cellular Targets for Anti-Epileptic Drugs 1997 John Libbey London 191 198
22. D. Matosiuk, D. Gralak, and M. Ryznar Lipophilicityof natural coumarins Ann. UMCS Sectio DDD 24 2011 19 25
23. F. Tosun, C.A. Kizilay, K. Erol, F.S. Kiliç, M. Kürkçüoʇlu, and K.H.C. Başer Anticonvulsant activity of furanocoumarins and the essential oil obtained from the fruits of Heracleum crenatifolium Food Chem. 107 2008 990 993
24. K. Skalika-Woźniak, M. Zagaja, K. Głowniak, and J.J. Luszczki Purification and anticonvulsant activity of xanthotoxin (8-methoxypsoralen) Cent. Eur. J. Biol. 9 2014 431 436
25. J.J. Luszczki, E. Wojda, M. Andres-Mach, W. Cisowski, M. Glensk, K. Glowniak, and S.J. Czuczwar Anticonvulsant and acute neurotoxic effects of imperatorin, osthole and valproate in the maximal electroshock seizure and chimney tests in mice: a comparative study Epilepsy Res. 85 2009 293 299
26. M. Zagaja, D. Pyrka, K. Skalicka-Wozniak, K. Glowniak, M. Florek-Luszczki, M. Glensk, and J.J. Luszczki Effect of xanthotoxin (8-methoxypsoralen) on the anticonvulsant activity of classical antiepileptic drugs against maximal electroshock-induced seizures in mice Fitoterapia 105 2015 1 6
27. M. Zagaja, M. Andres-Mach, K. Skalicka-Woźniak, A.R. Rękas, M.W. Kondrat-Wróbel, M. Gleńsk, and J.J. Łuszczki Assessment of the combined treatment with umbelliferone and four classical antiepileptic drugs against maximal electroshock-induced seizures in mice Pharmacology 96 2015 175 180
28. D.C. Cooper, and F.J. White L-Type calcium channels modulate glutamate-driven bursting activity in the nucleus accumbens in vivo Brain Res. 880 2000 212 218
29. J.J. Luszczki, M. Andres-Mach, W. Cisowski, I. Mazol, K. Glowniak, and S.J. Czuczwar Osthole suppresses seizures in the mouse maximal electroshock seizure model Eur. J. Pharmacol. 607 2009 107 109
30. T.S. Woo, S.Y. Yoon, I.C. dela Pena, J.Y. Choi, H.L. Lee, Y.J. Choi, Y.S. Lee, J.H. Ryu, J.S. Choi, and J.H. Cheong Anticonvulsant effect of Artemisia capillaris Herba in mice Biomol. Ther. 19 2011 342 347
31. S. Genovese, F. Epifano, M. Curini, M. Dudra-Jastrzebska, and J.J. Luszczki Prenyloxyphenylpropanoids as a novel class of anticonvulsive agents Bioorg. Med. Chem. Lett. 19 2009 5419 5422
32. N. Siddiqui, M.F. Arshad, and S. Khan Synthesis of some new coumarin incorporated thiazolyl semicarbazones as anticonvulsants Acta Pol. Pharm. 66 2009 161 167
33. R.I. Shader, and D.J. Greenblatt Use of benzodiazepines in anxiety disorders New Engl. J. Med. 328 1993 1398 1405
34. L.H. Sternbach The benzodiazepine story Prog. Drug Res. 22 1978 229 266
35. B. Budzynska, M. Kruk-Slomka, K. Skalicka-Wozniak, G. Biala, and K. Glowniak The effects of imperatorin on anxiety and memory-related behavior in male Swiss mice Exp. Clin. Psychopharmacol. 20 2012 325 332
36. B. Budzynska, A. Boguszewska-Czubara, M. Kruk-Slomka, K. Skalicka-Wozniak, A. Michalak, I. Musik, G. Biala, and K. Glowniak Effects of imperatorin on nicotine-induced anxiety- and memory-related responses and oxidative stress in mice Physiol. Behav. 122 2013 46 55
37. D. Kumar, Z.A. Bhat, V. Kumar, and M.Y. Shah Coumarins from Angelica archangelica Linn, and their effects on anxiety-like behavior Prog. Neuropsychopharmacol. Biol. Psychiatry 40 2013 180 186
38. K.C. Wu, Y.H. Chen, K.S. Cheng, Y.H. Kuo, C.T. Yang, K.L. Wong, Y.K. Tu, P. Chan, and Y.M. Leung Suppression of voltage-gated Na channels and neuronal excitability by imperatorin Eur. J. Pharmacol. 721 2013 49 55
39. J. Wouters Structural aspects of monoamine oxidase and its reversible inhibition Curr. Med. Chem. 5 1998 137 162
40. P. Foley, M. Gerlach, M.B.H. Youdim, and P. Riederer MAO-B inhibitors: multiple roles in the therapy of neurodegenerative disorders? Parkinsonism Relat. D 6 2000 25 47
41. Y.S. Jo, T.L. Huong, K.H. Bae, M.K. Lee, and Y.H. Kim Monoamine oxidase inhibitory coumarin from Zanthoxylum schinifolium Planta Med. 68 2002 84 85
42. C.F. Hossain, E. Okuyama, and M. Yamazaki A new series of coumarin derivatives having monoamine oxidase inhibitory activity from Monascus anka Chem. Pharm. Bull. 44 1996 1535 1539
43. D.T.L. Huong, H.C. Choi, T.C. Rho, H.S. Lee, M.K. Lee, and Y.H. Kim Inhibitory activity of monoamine oxidase by coumarins from Peucedanum japonicum Arch. Pharm. Res. 22 1999 324 326
44. S.H. Jeong, X.H. Han, S.S. Hong, J.S. Hwang, J.H. Hwang, D. Lee, M.K. Lee, J.S. Ro, and B.Y. Hwang Monoamine oxidase inhibitory coumarins from the aerial parts of Dictammus albus Arch. Pharm. Res. 29 2006 1119 1124
45. L.D. Kong, R.X. Tan, A.Y.H. Woo, and C.H.K. Cheng Inhibition of rat brain monoamine oxidase activities by psoralen and isopsoralen: implications for the treatment of affective disorders Pharmacol. Toxicol. 88 2001 75 80
46. J.C. Capra, M.P. Cunha, D.G. Machado, A.D. Zomkowski, B.G. Mendes, A.R. Santos, M.G. Pizzolatti, and A.L. Rodrigues Antidepressant-like effect of scopoletin, a coumarin isolated from Polygala sabulosa (Polygalaceae) in mice: evidence for the involvement of monoaminergic systems Eur. J. Pharmacol. 643 2010 232 238
47. Q. Xu, Y. Pan, L.T. Yi, Y.C. Li, S.F. Mo, F.X. Jiang, C.F. Qiao, H.X. Xu, X.B. Lu, L.D. Kong, and H.F. Kung Antidepressant-like effects of psoralen isolated from the seeds of Psoralea corylifolia in the mouse forced swimming test Biol. Pharm. Bull. 31 2008 1109 1114
48. A. Carotti, A. Carrieri, S. Chimichi, M. Boccalini, B. Cosimelli, C. Gnerre, A. Carotti, P.A. Carrupt, and B. Testa Natural and synthetic geiparvarins are strong and selective MAO-B inhibitors. Synthesis and SAR studies Bioorg. Med. Chem. Lett. 12 2002 3551 3555
49. F. Chimenti, D. Secci, A. Bolasco, P. Chimenti, A. Granese, O. Befani, P. Turini, S. Alcaro, and F. Ortuso Inhibition of monoamine oxidases by coumarin-3-acyl derivatives: biological activity and computational study Bioorg. Med. Chem. Lett. 14 2004 3697 3703
50. F. Chimenti, D. Secci, A. Bolasco, P. Chimenti, A. Granese, L. Gagliardi, and D. De Orsi LC determination of coumarin-3-acyl derivatives for evaluation of the stability and monoamine oxidase inhibition mechanism Chromatographia 61 2005 519 522
51. M.J. Matos, D. Viña, E. Quezada, C. Picciau, G. Delogu, F. Orallo, L. Santana, and E. Uriarte A new series of 3-phenylcoumarins as potent and selective MAO-B inhibitors Bioorg. Med. Chem. Lett. 19 2009 3268 3270
52. M.J. Matos, C. Terán, Y. Pérez-Castillo, E. Uriarte, L. Santana, and D. Viña Synthesis and study of a series of 3-arylcoumarins as potent and selective monoamine oxidase B inhibitors J. Med. Chem. 54 2011 7127 7137
53. M.R. Loizzo, R. Tundis, F. Menichini, and F. Menichini Natural products and their derivatives as cholinesterase inhibitors in the treatment of neurodegenerative disorders: an update Curr. Med. Chem. 15 2008 1209 1228
54. K. Hostettmann, A. Borloz, A. Urbain, and A. Marston Natural product inhibitors of acetylcholinesterase Curr. Org. Chem. 10 2006 825 847
55. L. Piazzi, A. Cavalli, F. Colizzi, F. Belluti, M. Bartolini, F. Mancini, M. Recanatini, V. Andrisano, and A. Rampa Multi-target-directed coumarin derivatives: AChE and BACE1 inhibitors as potential anti-Alzheimer compounds Bioorg. Med. Chem. Lett. 18 2008 423 426
56. Q. Shen, Q. Peng, J. Shao, X. Liu, Z. Huang, X. Pu, L. Ma, Y.M. Li, A.S.C. Chan, and L. Gu Synthesis and biological evaluation of functionalized coumarins as acetylcholinesterase inhibitors Eur. J. Med. Chem. 40 2005 1307 1315
57. C. Brühlmann, F. Ooms, P.A. Carrupt, B. Testa, M. Catto, F. Leonetti, C. Altomare, and A. Carotti Coumarins derivatives as dual inhibitors of acetylcholinesterase and monoamine oxidase J. Med. Chem. 44 2001 195 198
58. C. Gnerre, M. Catto, F. Leonetti, P. Weber, P.A. Carrupt, C. Altomare, A. Carotti, and B. Testa Inhibition of monoamine oxidases by functionalized coumarin derivatives: biological activities, QSARs, and 3D-QSARs J. Med. Chem. 43 2000 4747 4758
59. J.M. Rollinger, A. Hornick, T. Langer, H. Stuppner, and H. Prast Acetylcholinesterase inhibitory activity of scopolin and scopoletin discovered by virtual screening of natural products J. Med. Chem. 47 2004 6248 6254
60. J.H. Lee, K.T. Lee, J.H. Yang, N.I. Baek, and D.K. Kim Acetylcholinesterase inhibitors from the twigs of Vaccinium oldhami Miquel Arch. Pharm. Res. 27 2004 53 56
61. I. Orhan, F. Tosun, and B. Şener Coumarin, anthraquinone and stilbene derivatives with anticholinesterase activity Z. Naturforsch. C 63 2008 366 370
62. S.Y. Kang, K.Y. Lee, S.H. Sung, M.J. Park, and Y.C. Kim Coumarins isolated from Angelica gigas inhibit acetylcholinesterase: structure-activity relationships J. Nat. Prod. 64 2001 683 685
63. S. Di Giovanni, A. Borloz, A. Urbain, A. Marston, K. Hostettmann, P.A. Carrupt, and M. Reist In vitro screening assays to identify natural or synthetic acetylcholinesterase inhibitors: thin layer chromatography versus microplate methods Eur. J. Pharm. Sci. 33 2008 109 119
64. M. Miyazawa, T. Tsukamoto, J. Anzai, and Y. Ishikawa Insecticidal effect of phthalides and furanocoumarins from Angelica acutiloba against Drosophila melanogaster J. Agric. Food Chem. 52 2004 4401 4405
65. K. Awang, G. Chan, M. Litaudon, N.H. Ismail, M.T. Martin, and F. Gueritte 4-Phenylcoumarins from Mesua elegans with acetylcholinesterase inhibitory activity Bioorg. Med. Chem. 18 2010 7873 7877
66. A. Urbain, A. Marston, and K. Hostettmann Coumarins from Peucedanum ostruthium as inhibitors of acetylcholinesterase Pharm. Biol. 43 2005 647 650
67. M.I. Choudhary, A. Khalid, A. Sultani, and S.Z. Atta-ur-Rahman A new coumarin from Murraya paniculata Planta Med. 68 2002 81 83
68. M.J. Matos, P. Janeiro, R.M. González Franco, S. Vilar, N.P. Tatonetti, L. Santana, E. Uriarte, F. Borges, J.A. Fontenla, and D. Viña Synthesis, pharmacological study and docking calculations of new benzo[f]coumarin derivatives as dual inhibitors of enzymatic systems involved in neurodegenerative diseases Fut. Med. Chem. 6 2014 371 383
69. F.S. Senol, K. Skalicka-Wozniak, M.T.H. Khan, I.E. Orhan, B. Sener, and K. Głowniak An in vitro and in silico approach to cholinesterase inhibitory and antioxidant effects of the methanol extract, furanocoumarin fraction, and major coumarins of Angelica officinalis L. fruits Phytochem. Lett. 4 2011 462 467
70. N. Wszelaki, K. Paradowsk, M.K. Jamróz, S. Granica, and A.K. Kiss Bioactivity-guided fractionation for the butyrylcholinesterase inhibitory activity of furanocoumarins from Angelica archangelica L. roots and fruits J. Agric. Food Chem. 59 2011 9186 9193
71. M. Alipour, M. Khoobi, A. Foroumadi, H. Nadri, A. Moradi, A. Sakhteman, M. Ghandi, and A. Shafiee Novel coumarin derivatives bearing N-benzyl pyridinium moiety: potent and dual binding site acetylcholinesterase inhibitors Bioorg. Med. Chem. 20 2012 7214 7222
72. L. Piazzi, A. Rampa, A. Bisi, S. Gobbi, F. Belluti, A. Cavalli, M. Bartolini, V. Andrisano, P. Valenti, and M. Recanatini 3-(4-{[Benzyl(methyl) amino]methyl}-phenyl)-6,7-dimethoxy-2H-2-chromenone (AP2238) inhibits both acetylcholinesterase and acetylcholinesterase-induced β-amyloid aggregation: a dual function lead for Alzheimer's disease therapy J. Med. Chem. 46 2003 2279 2282
73. L. Piazzi, A. Cavalli, F. Belluti, A. Bisi, S. Gobbi, S. Rizzo, M. Bartolini, V. Andrisano, M. Recanatini, and A. Rampa Extensive SAR and computational studies of 3-{4-[(benzylmethylamino) methyl]phenyl}-6,7-dimethoxy-2H-2-chromenone (AP2238) derivatives J. Med. Chem. 50 2007 4250 4254
74. X. Zhou, X.B. Wang, T. Wang, and L.Y. Kong Design, synthesis, and acetylcholinesterase inhibitory activity of novel coumarin analogues Bioorg. Med. Chem. 16 2008 8011 8021
75. C. Puma, O. Deschaux, R. Molimard, and J.C. Bizot Nicotine improves memory in an object recognition task in rats Eur. Neuropsychopharmacol. 9 1999 323 327
76. M. Tsuji, H. Takeda, and T. Matsumiya Modulation of passive avoidance in mice by the 5-HT1A receptor agonist flesinoxan: comparison with the benzodiazepine receptor agonist diazepam Neuropsychopharmacology 28 2003 664 674
77. A. Kanwal, J. Mehla, M. Kuncha, V.G.M. Naidu, Y.K. Gupta, and R. Sistla Anti-amnesic activity of Vitex negundo in scopolamine induced amnesia in rats Pharmacol. Pharm. 1 2010 1 8
78. B. Budzynska, A. Boguszewska-Czubara, M. Kruk-Slomka, K. Skalicka-Wozniak, A. Michalak, I. Musik, and G. Biala Effects of imperatorin on scopolamine-induced cognitive impairment and oxidative stress in mice Psychopharmacology (Berl) 232 2015 931 942
79. A. Hornick, A. Lieb, N.P. Vo, J.M. Rollinger, H. Stuppner, and H. Prast The coumarin scopoletin potentiates acetylcholine release from synaptosomes, amplifies hippocampal long-term potentiation and ameliorates anticholinergic- and age-impaired memory Neuroscience 197 2011 280 292
80. J.K. Kim, S.J. Choi, H. Bae, C.R. Kim, H.Y. Cho, Y.J. Kim, S.T. Lim, C.J. Kim, H.K. Kim, S. Peterson, and D.H. Shin Effects of methoxsalen from Poncirus trifoliata on acetylcholinesterase and trimethyltin-induced learning and memory impairment Biosci. Biotechnol. Biochem. 75 2011 1984 1989
81. D.H. Kim, Y. Kim, Y.C. Kim, J.W. Jung, S. Lee, B.H. Yoon, J.H. Cheong, Y.S. Kim, S.S. Kang, K.H. Ko, and J.H. Ryu Nodakenin, a coumarin compound, ameliorates scopolamine-induced memory disruption in mice Life Sci. 80 2007 1944 1950
82. Q. Gao, S.J. Jeon, H.A. Jung, H.E. Lee, S.J. Park, Y. Lee, Y. Lee, S.Y. Ko, B. Kim, J.S. Choi, and J.H. Ryu Nodakenin enhances cognitive function and adult hippocampal neurogenesis in mice Neurochem. Res. 40 2015 1438 1447
83. S.Y. Kang, K.Y. Lee, S.H. Sung, and Y.C. Kim Four new neuroprotective dihydropyranocoumarins from Angelica gigas J. Nat. Prod. 68 2005 56 59
84. S.Y. Kang, and Y.C. Kim Decursinol and decursin protect primary cultured rat cortical cells from glutamate-induced neurotoxicity J. Pharm. Pharmacol. 59 2007 863 870
85. S.J. Wang, T.Y. Lin, C.W. Lu, and W.J. Huang Osthole and imperatorin, the active constituents of Cnidium monnieri (L.) Cusson, facilitate glutamate release from rat hippocampal nerve terminals Neurochem. Int. 53 2008 416 423
86. J.K. Lee, S.S. Choi, H.K. Lee, K.J. Han, E.J. Han, and H.W. Suh Effects of ginsenoside Rd and decursinol on the neurotoxic responses induced by kainic acid in mice Planta Med. 69 2003 230 234
87. S.Y. Kang, K.Y. Lee, M.J. Park, Y.C. Kim, G.J. Markelonis, T.H. Oh, and Y.C. Kim Decursin from Angelica gigas mitigates amnesia induced by scopolamine in mice Neurobiol. Learn. Mem. 79 2015 11 18
88. J.J. Yan, D.H. Kim, Y.S. Moon, J.S. Jung, E.M. Ahn, N.I. Baek, and D.K. Song Protection against β-amyloid peptide-induced memory impairment with long-term administration of extract of Angelica gigas or decursinol in mice Prog. Neuro-psychoph. 28 2004 25 30
89. S.S. Choi, K.J. Han, J.K. Lee, H.K. Lee, E.J. Han, D.H. Kim, and H.W. Suh Antinociceptive mechanisms of orally administered decursinol in the mouse Life Sci. 73 2003 471 485
90. S.Y. Kang, and Y.C. Kim Neuroprotective coumarins from the root of Angelica gigas: structure-activity relationships Arch. Pharm. Res. 30 2007 1368 1373
91. M.F. Molina-Jimenez, M.I. Sanchez-Reus, and J. Benedi Effect of fraxetin and myricetin on rotenone-induced cytotoxicity in SH-SY5Y cells: comparison with N-acetylcysteine Eur. J. Pharmacol. 472 2003 81 87
92. F. Epifiano, M. Curini, L. Menghini, and S. Genovese Natural coumarins and a novel class of neuroprotective agents Mini Rev. Med. Chem. 9 2009 1262 1271
93. M.F. Molina-Jiménez, M.I. Sánchez-Reus, M. Cascales, D. Andrés, and J. Benedí Effect of fraxetin on antioxidant defense and stress proteins in human neuroblastoma cell model of rotenone neurotoxicity. Comparative study with myricetin and N-acetylcysteine Toxicol. Appl. Pharmacol. 209 2005 214 225
94. M.I. Sánchez-Reus, I.I. Peinado, M.F. Molina-Jiménez, and J. Benedí Fraxetin prevents rotenone-induced apoptosis by induction of endogenous glutathione in human neuroblastoma cells Neurosci. Res. 53 2005 48 56
95. F. Cheng, Z. Deng, Z. Guo, J. Chen, and K. Zou Machilusmarin, a new neuroprotective isocoumarin dimer from the stems of Machilus ichangensis Rehd. et Wils Nat. Prod. Res. 27 2013 1542 1547
96. E.C. Pereira, D.L. Lucetti, J.M. Barbosa-Filho, E.M. de Brito, V.S. Monteiro, M.C.A. Patrocínio, R.R. de Moura, L.K.A.M. Leal, D.S. Macedo, F.C.F. de Sousa, G.S. de Barros Viana, and S.M.M. Vasconcelos Coumarin effects on amino acid levels in mice prefrontal cortex and hippocampus Neurosci. Lett. 454 2009 139 142
97. H.J. Ji, J.F. Hu, Y.H. Wang, X.Y. Chen, R. Zhou, and N.H. Chen Osthole improves chronic cerebral hypoperfusion induced cognitive deficits and neuronal damage in hippocampus Eur. J. Pharmacol. 636 2010 96 101
98. Y. He, S. Qu, J. Wang, X. He, W. Lin, H. Zhen, and X. Zhang Neuroprotective effects of osthole pretreatment against traumatic brain injury in rats Brain Res. 1433 2012 127 136
99. X. Chao, J. Zhou, T. Chen, W. Liu, W. Dong, Y. Qu, X. Jiang, X. Ji, H. Zhen, and Z. Fei Neuroprotective effect of osthole against acute ischemic stroke on middle cerebral ischemia occlusion in rats Brain Res. 1363 2010 206 211
100. X. Mao, W. Yin, M. Liu, M. Ye, P. Liu, J. Liu, Q. Lian, S. Xu, and R. Pi Osthole, a natural coumarin, improves neurobehavioral functions and reduces infarct volume and matrix metalloproteinase-9 activity after transient focal cerebral ischemia in rats Brain Res. 1385 2011 275 280
101. C. Wang, A. Pei, J. Chen, H. Yu, M.L. Sun, C.F. Liu, and X. Xu A natural coumarin derivative esculetin offers neuroprotection on cerebral ischemia/reperfusion injury in mice J. Neurochem. 121 2012 1007 1013
102. F. Epifano, G. Molinaro, S. Genovese, R.T. Ngomba, F. Nicoletti, and M. Curini Neuroprotective effect of prenyloxycoumarins from edible vegetables Neurosci. Lett. 443 2008 57 60
103. S. Okuyama, S. Minami, N. Shimada, N. Makihata, M. Nakajima, and Y. Furukawa Anti-inflammatory and neuroprotective effects of auraptene, a citrus coumarin, following cerebral global ischemia in mice Eur. J. Pharmacol. 699 2013 118 123
104. J. Shi, C.J. Li, J.Z. Yang, Y.H. Yuan, N.H. Chen, and D.M. Zhang Coumarin glycosides and iridoid glucosides with neuroprotective effects from Hydrangea paniculata Planta Med. 78 2012 1844 1850
105. L. Yang, X.B. Li, Q. Yang, K. Zhang, N. Zhang, Y.Y. Guo, B. Feng, M.G. Zhao, and Y.M. Wu The neuroprotective effect of praeruptorin C against NMDA-induced apoptosis through down-regulating of GluN2B-containing NMDA receptors Toxicol. In Vitro 27 2013 908 914
106. W. He, W. Chen, Y. Zhou, Y. Tian, and F. Liao Xanthotoxol exerts neuroprotective effects via suppression of the inflammatory response in a rat model of focal cerebral ischemia Cell. Mol. Neurobiol. 33 2013 715 722
107. M. Sun, J. Hu, X. Song, D. Wu, L. Kong, Y. Sun, D. Wang, Y. Wang, N. Chen, and G. Liu Coumarin derivatives protect against ischemic brain injury in rats Eur. J. Med. Chem. 67 2013 39 53
108. W. Su, J. Zhao, M. Yang, H.W. Yan, T. Pang, S.H. Chen, H.Y. Huang, S.H. Zhang, X.C. Ma, D.A. Guo, I.A. Khan, and W. Wang A coumarin lignanoid from the stems of Kadsura heteroclita Bioorg. Med. Chem. Lett. 25 2015 1506 1508
109. G. Du, H. Tu, X. Li, A. Pei, J. Chen, Z. Miao, J. Li, C. Wang, H. Xie, X. Xu, and H. Zhao Daphnetin, a natural coumarin derivative, provides the neuroprotection against glutamate-induced toxicity in HT22 cells and ischemic brain injury Neurochem. Res. 39 2014 269 275
110. X. Jin, Y. Wang, X. Li, X. Tan, Z. Miao, Y. Chen, R.C. Hamdy, B.H.L. Chua, J. Kong, H. Zhao, and X. Xu 7,8-Dihydroxy-4-methylcoumarin provides neuroprotection by increasing hippocalcin expression Neurotoxicol. Res. 27 2015 268 274
111. D.E. Nichols, and C.D. Nichols Serotonin receptors Chem. Rev. 108 2008 1614 1641
112. J.H. Beaulieu, and R.R. Gainetdinov The physiology, signaling, and pharmacology of dopamine receptors Pharmacol. Rev. 63 2011 182 217
113. 2A receptors Bioorg. Med. Chem. Lett. 13 2003 175 178
114. 3 receptors Bioorg. Med. Chem. Lett. 8 1998 3567 3570
115. 2A receptors Eur. J. Med. Chem. 37 2002 503 510
116. Y.J. Yang, H.J. Lee, H.S. Huang, B.K. Lee, H.S. Choi, S.C. Lim, C.K. Lee, and M.K. Lee Effects of scoparone on dopamine biosynthesis and L-DOPA-induced cytotoxicity in PC12 cells J. Neurosci. Res. 87 2009 1929 1937
117. T. Fujimaki, S. Saiki, E. Tashiro, D. Yamada, M. Kitagawa, N. Hattori, and M. Imoto Identification of licopyranocoumarin and glycyrurol from herbal medicines as neuroprotective compounds for Parkinson's disease PLoS One 9 2014 e100395
118. R. Hoerr, and M. Noeldner Ensaculin (KA-672HCl): a multitransmitter approach to dementia treatment CNS Drug Rev. 8 2002 143 158