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New insights into the biological properties of Crocus sativus L.: chemical modifications, human monoamine oxidases inhibition and molecular modeling studies.
Eur J Med Chem. 2014 Jul 23; 82:164-71.EJ

Abstract

Although there are clinical trials and in vivo studies in literature regarding the anxiolytic and antidepressant activities of the components of Crocus sativus L., their effects on the human monoamine oxidases (hMAO-A and hMAO-B), enzymes which are involved in mental disorders and neurodegenerative diseases, have not yet been investigated. We have thus examined the hMAO inhibitory activities of crocin and safranal (the most important active principles in saffron) and, subsequently, designed a series of safranal derivatives to evaluate which chemical modifications confer enhanced inhibition of the hMAO isoforms. Docking simulations were performed in order to identify key molecular recognitions of these inhibitors with both isoforms of hMAO. In this regard, different mechanisms of action were revealed. This study concludes that safranal and crocin represent useful leads for the discovery of novel hMAO inhibitors for the clinical management of psychiatric and neurodegenerative disorders.

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Authors+Show Affiliations

De Monte C
Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza University of Rome, P.le A. Moro 5, 00185 Rome, Italy.
Carradori S
Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza University of Rome, P.le A. Moro 5, 00185 Rome, Italy. Electronic address: simone.carradori@uniroma1.it.
Chimenti P
Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza University of Rome, P.le A. Moro 5, 00185 Rome, Italy.
Secci D
Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza University of Rome, P.le A. Moro 5, 00185 Rome, Italy.
Mannina L
Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza University of Rome, P.le A. Moro 5, 00185 Rome, Italy; Istituto di Metodologie Chimiche, Laboratorio di Risonanza Magnetica "Annalaura Segre", CNR, via Salaria km 29.300, 00015 Monterotondo, Rome, Italy.
Alcaro F
Dipartimento di Scienze della Salute, "Magna Graecia" University of Catanzaro, Campus Universitario "S. Venuta", Viale Europa Loc. Germaneto, 88100 Catanzaro, Italy.
Petzer A
Pharmaceutical Chemistry and Centre of Excellence for Pharmaceutical Sciences, School of Pharmacy, North-West University, Private Bag X6001, Potchefstroom 2520, South Africa.
N'Da CI
Pharmaceutical Chemistry and Centre of Excellence for Pharmaceutical Sciences, School of Pharmacy, North-West University, Private Bag X6001, Potchefstroom 2520, South Africa.
Gidaro MC
Dipartimento di Scienze della Salute, "Magna Graecia" University of Catanzaro, Campus Universitario "S. Venuta", Viale Europa Loc. Germaneto, 88100 Catanzaro, Italy.
Costa G
Dipartimento di Scienze della Salute, "Magna Graecia" University of Catanzaro, Campus Universitario "S. Venuta", Viale Europa Loc. Germaneto, 88100 Catanzaro, Italy.
Alcaro S
Dipartimento di Scienze della Salute, "Magna Graecia" University of Catanzaro, Campus Universitario "S. Venuta", Viale Europa Loc. Germaneto, 88100 Catanzaro, Italy.
Petzer JP
Pharmaceutical Chemistry and Centre of Excellence for Pharmaceutical Sciences, School of Pharmacy, North-West University, Private Bag X6001, Potchefstroom 2520, South Africa. Electronic address: jacques.petzer@nwu.ac.za.

MeSH

CrocusCrystallography, X-RayCyclohexenesDose-Response Relationship, DrugHumansModels, MolecularMolecular StructureMonoamine OxidaseMonoamine Oxidase InhibitorsPlant StructuresStructure-Activity RelationshipTerpenes

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24904963

Citation

De Monte, Celeste, et al. "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, vol. 82, 2014, pp. 164-71.
De Monte C, Carradori S, Chimenti P, et al. New insights into the biological properties of Crocus sativus L.: chemical modifications, human monoamine oxidases inhibition and molecular modeling studies. Eur J Med Chem. 2014;82:164-71.
De Monte, C., Carradori, S., Chimenti, P., Secci, D., Mannina, L., Alcaro, F., Petzer, A., N'Da, C. I., Gidaro, M. C., Costa, G., Alcaro, S., & Petzer, J. P. (2014). 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, 82, 164-71. https://doi.org/10.1016/j.ejmech.2014.05.048
De Monte C, et al. New Insights Into the Biological Properties of Crocus Sativus L.: Chemical Modifications, Human Monoamine Oxidases Inhibition and Molecular Modeling Studies. Eur J Med Chem. 2014 Jul 23;82:164-71. PubMed PMID: 24904963.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - New insights into the biological properties of Crocus sativus L.: chemical modifications, human monoamine oxidases inhibition and molecular modeling studies. AU - De Monte,Celeste, AU - Carradori,Simone, AU - Chimenti,Paola, AU - Secci,Daniela, AU - Mannina,Luisa, AU - Alcaro,Francesca, AU - Petzer,Anél, AU - N'Da,Clarina I, AU - Gidaro,Maria Concetta, AU - Costa,Giosuè, AU - Alcaro,Stefano, AU - Petzer,Jacobus P, Y1 - 2014/05/22/ PY - 2014/01/29/received PY - 2014/05/13/revised PY - 2014/05/21/accepted PY - 2014/6/7/entrez PY - 2014/6/7/pubmed PY - 2015/3/31/medline KW - Crocin KW - Crocus sativus L. KW - Depression KW - Neurodegenerative disorders KW - Safranal KW - hMAO inhibitors SP - 164 EP - 71 JF - European journal of medicinal chemistry JO - Eur J Med Chem VL - 82 N2 - Although there are clinical trials and in vivo studies in literature regarding the anxiolytic and antidepressant activities of the components of Crocus sativus L., their effects on the human monoamine oxidases (hMAO-A and hMAO-B), enzymes which are involved in mental disorders and neurodegenerative diseases, have not yet been investigated. We have thus examined the hMAO inhibitory activities of crocin and safranal (the most important active principles in saffron) and, subsequently, designed a series of safranal derivatives to evaluate which chemical modifications confer enhanced inhibition of the hMAO isoforms. Docking simulations were performed in order to identify key molecular recognitions of these inhibitors with both isoforms of hMAO. In this regard, different mechanisms of action were revealed. This study concludes that safranal and crocin represent useful leads for the discovery of novel hMAO inhibitors for the clinical management of psychiatric and neurodegenerative disorders. SN - 1768-3254 UR - https://www.unboundmedicine.com/medline/citation/24904963 DB - PRIME DP - Unbound Medicine ER -
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