New insights into the biological properties of Crocus sativus L.: Chemical modifications, human monoamine oxidases inhibition and molecular modeling studies

European Journal of Medicinal Chemistry

Volumn 82, Issue , 2014, Pages 164-171

  De Monte, Celeste ^a   Carradori, Simone ^a   Chimenti, Paola ^a   Secci, Daniela ^a   Mannina, Luisa ^a,d   Alcaro, Francesca ^b   Petzer, Anél ^c   N'Da, Clarina I ^c   Gidaro, Maria Concetta ^b   Costa, Giosuè ^b   Alcaro, Stefano ^b   Petzer, Jacobus P ^c  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY MAGNA GRAECIA OF CATANZARO   (Italy)

^c NORTH WEST UNIVERSITY   (South Africa)

^d CNR   (Italy)

Author keywords

Crocin; Crocus sativus L.; Depression; hMAO inhibitors; Neurodegenerative disorders; Safranal

Indexed keywords

1 [(2,6,6 TRIMETHYLCYCLOHEXA 1,3 DIENYL)METHYLENE] 4 PHENYLTHIOSEMICARBAZIDE; 1 [(2,6,6 TRIMETHYLCYCLOHEXA 1,3 DIENYL)METHYLENE]SEMICARBAZIDE; 1 [(2,6,6 TRIMETHYLCYCLOHEXA 1,3 DIENYL)METHYLENE]THIOSEMICARBAZIDE; 1 [4 (3 NITROPHENYL)THIAZOL 2 YL] 2 [(2,6,6 TRIMETHYLCYCLOHEXA 1,3 DIENYL)METHYLENE]HYDRAZINE; 2 METHYL 1 [(2,6,6 TRIMETHYLCYCLOHEXA 1,3 DIENYL)METHYLENE]THIOSEMICARBAZIDE; 2 [2 [(2,6,6 TRIMETHYLCYCLOHEXA 1,3 DIENYL)METHYLENE]HYDRAZONO]THIAZOLIDIN 4 ONE; 2,6,6 TRIMETHYLCYCLOHEXA 1,3 DIENECARBALDEHYDE; 3 BENZYL 2 [2 [(2,6,6 TRIMETHYLCYCLOHEXA 1,3 DIENYL)METHYLENE]HYDRAZO]THIAZOLIDIN 4 ONE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; CROCIN; PLANT MEDICINAL PRODUCT; SAFRANAL; UNCLASSIFIED DRUG; AMINE OXIDASE (FLAVIN CONTAINING); CYCLOHEXENE DERIVATIVE; MONOAMINE OXIDASE INHIBITOR; TERPENE;

ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; CROCUS SATIVUS; DRUG MECHANISM; ENZYME INHIBITION; MOLECULAR DOCKING; MOLECULAR RECOGNITION; PHYSICAL CHEMISTRY; CHEMICAL STRUCTURE; CHEMISTRY; CROCUS; DOSE RESPONSE; HUMAN; ISOLATION AND PURIFICATION; METABOLISM; PLANT STRUCTURES; STRUCTURE ACTIVITY RELATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CROCUS; CRYSTALLOGRAPHY, X-RAY; CYCLOHEXENES; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; PLANT STRUCTURES; STRUCTURE-ACTIVITY RELATIONSHIP; TERPENES;

EID: 84902213282     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.05.048     Document Type: Article

References (41)

1. S. Carradori, M. D'Ascenzio, P. Chimenti, D. Secci, and A. Bolasco Mol. Divers. 18 2014 219 243
2. S. Carradori, D. Secci, A. Bolasco, P. Chimenti, and M. D'Ascenzio Expert Opin. Ther. Patents 22 2012 759 801
3. A. Bolasco, R. Fioravanti, and S. Carradori Expert Opin. Ther. Patents 15 2005 1763 1782
4. A. Bolasco, S. Carradori, and R. Fioravanti Expert Opin. Ther. Patents 20 2010 909 939
5. J. Sarris, A. Panossian, I. Schweitzer, C. Stough, and A. Scholey Eur. Neuropsychopharmacol. 21 2011 841 860
6. S.Z. Bathaie, and S.Z. Mousavi Crit. Rev. Food Sci. Nutr. 50 2010 761 786
7. B.A. Wani, A.K.R. Hamza, and F.A.J. Mohiddin Med. Plant. Res. 5 2011 2131 2135
8. Z.I. Linardaki, M.G. Orkoula, A.G. Kokkosis, F.N. Lamari, and M. Margarity Food Chem. Toxicol. 52 2013 163 170
9. M. Lechtenberg, D. Schepmann, M. Niehues, N. Hellenbrand, B. Wünsch, and A. Hensel Planta Med. 74 2008 764 772
10. A.A. Basti, E. Moshiri, A.A. Noorbala, A.H. Jamshidi, S.H. Abbasi, and S. Akhondzadeh Prog. Neuro-psychopharmacol. Biol. Psychiatry 31 2007 439 442
11. A.A. Noorbalaa, S. Akhondzadeh, N. Tahmacebi-Pour, and A.H. Jamshidi J. Ethnopharmacol. 97 2005 281 284
12. S. Akhondzadeh, H. Fallah-Pour, K. Afkham, A.H. Jamshidi, and F. Khalighi-Cigaroudi BMC Complement. Altern. Med. 4 2004 12 16
13. E. Moshiria, A.A. Bastib, A.A. Noorbalac, A.H. Jamshidid, S.H. Abbasie, and S. Akhondzadehc Phytomedicine 13 2006 607 611
14. L. Kashani, F. Raisi, S. Saroukhani, H. Sohrabi, A. Modabbernia, A.-A. Nasehi, A. Jamshidi, M. Ashrafi, P. Mansouri, P. Ghaeli, and S. Akhondzadeh Hum. Psychopharmacol. Clin. Exp. 28 2013 54 60
15. A. Modabbernia, H. Sohrabi, A.-A. Nasehi, F. Raisi, S. Saroukhani, A. Jamshidi, M. Tabrizi, M. Ashrafi, and S. Akhondzadeh Psychopharmacology 223 2012 381 388
16. M. Schmidt, G. Betti, and A. Hensel Wien. Med. Wochenschr. 157 2007 315 319
17. G. Georgiadoua, P.A. Tarantilis, and N. Pitsikas Neurosci. Lett. 528 2012 27 30
18. F. Di Marco, S. Romeo, C. Nandasena, S. Purushothuman, C. Adams, S. Bisti, and J. Stone Am. J. Neurodegener. Dis. 2 2013 208 220
19. M.A. Papandreou, C.D. Kanakis, M.G. Polissiou, S. Efthimiopoulos, P. Cordopatis, M. Margarity, and F.N. Lamari J. Agric. Food Chem. 54 2006 8762 8768
20. G.D. Geromichalos, F.N. Lamari, M.A. Papandreou, D.T. Trafalis, M. Margarity, A. Papageorgiou, and Z. Sinakos J. Agric. Food Chem. 60 2012 6131 6138
21. K.N. Westlund, R.M. Denney, R.M. Rose, and C.W. Abell Neuroscience 25 1988 439 456
22. D.E. Edmondson, C. Binda, J. Wang, A.K. Upadhayay, and A. Mattevi Biochemistry 48 2009 4220 4230
23. M.B.H. Youdim, D.E. Edmondson, and K.F. Tipton Nat. Rev. 7 2006 295 309
24. M. Bortolato, K. Chen, and J.C. Shih Adv. Drug. Deliv. Rev. 60 2008 1527 1533
25. S. Carradori, M. D'Ascenzio, C. De Monte, D. Secci, and M. Yáñez Arch. Pharm. Chem. Life Sci. 346 2013 17 22
26. M. D'Ascenzio, S. Carradori, D. Secci, L. Mannina, A.P. Sobolev, C. De Monte, R. Cirilli, M. Yáñez, S. Alcaro, and F. Ortuso Bioorg. Med. Chem. 22 2014 2887 2895
27. P. Chimenti, A. Petzer, S. Carradori, M. D'Ascenzio, R. Silvestri, S. Alcaro, F. Ortuso, J.P. Petzer, and D. Secci Eur. J. Med. Chem. 66 2013 221 227
28. S. Carradori, D. Secci, P. D'Ascenzio, and A. Bolasco J. Heterocycl. Chem. 2014 10.1002/jhet.1856
29. D. Secci, A. Bolasco, S. Carradori, M. D'Ascenzio, R. Nescatelli, and M. Yáñez Eur. J. Med. Chem. 58 2012 405 417
30. F. Chimenti, D. Secci, A. Bolasco, P. Chimenti, A. Granese, S. Carradori, M. Yáñez, F. Orallo, F. Ortuso, and S. Alcaro Bioorg. Med. Chem. 18 2010 5715 5723
31. H.M. Berman, J. Westbrook, Z. Feng, G. Gilliland, T.N. Bhat, H. Weissig, I.N. Shindyalov, and P.E. Bourne Nucleic Acids Res. 28 2000 235 242
32. S.Y. Son, J. Ma, Y. Kondou, M. Yoshimura, E. Yamashita, and T. Tsukihara Proc. Natl. Acad. Sci. U. S. A. 105 2008 5739 5744
33. C. Binda, J. Wang, L. Pisani, C. Caccia, A. Carotti, P. Salvati, D.E. Edmondson, and A. Mattevi J. Med. Chem. 50 2007 5848 5852
34. Maestro, Version 9.4, Schrödinger, LLC, New York, NY, 2013.
35. Glide, Version 5.9, Schrödinger, LLC, New York, NY, 2013.
36. LigPrep, Version 2.6, Schrödinger, LLC, New York, NY, 2013.
37. Prime, Version 3.3, Schrödinger, LLC, New York, NY, 2013.
38. L. Novaroli, M. Reist, E. Favre, A. Carotti, M. Catto, and P.-A. Carrupt Bioorg. Med. Chem. 13 2005 6212 6217
39. A. Petzer, A. Pienaar, and J.P. Petzer Drug Res. 63 2013 462 467
40. F. Chimenti, R. Fioravanti, A. Bolasco, F. Manna, P. Chimenti, D. Secci, O. Befani, P. Turini, F. Ortuso, and S. Alcaro J. Med. Chem. 50 2007 425 428
41. A. Gaspar, T. Silva, M. Yáñez, D. Vina, F. Orallo, F. Ortuso, E. Uriarte, S. Alcaro, and F. Borges J. Med. Chem. 54 2011 5165 5173