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Hippeastrum reticulatum (Amaryllidaceae): Alkaloid Profiling, Biological Activities and Molecular Docking

The Amaryllidaceae family has proven to be a rich source of active compounds, which are characterized by unique skeleton arrangements and a broad spectrum of biological activities. The aim of this work was to perform the first detailed study of the alkaloid constituents of Hippeastrum reticulatum (A...

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Autores principales: Tallini, Luciana R., Osorio, Edison H., dos Santos, Vanessa Dias, Borges, Warley de Souza, Kaiser, Marcel, Viladomat, Francesc, Zuanazzi, José Angelo S., Bastida, Jaume
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6149799/
https://www.ncbi.nlm.nih.gov/pubmed/29232852
http://dx.doi.org/10.3390/molecules22122191
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author Tallini, Luciana R.
Osorio, Edison H.
dos Santos, Vanessa Dias
Borges, Warley de Souza
Kaiser, Marcel
Viladomat, Francesc
Zuanazzi, José Angelo S.
Bastida, Jaume
author_facet Tallini, Luciana R.
Osorio, Edison H.
dos Santos, Vanessa Dias
Borges, Warley de Souza
Kaiser, Marcel
Viladomat, Francesc
Zuanazzi, José Angelo S.
Bastida, Jaume
author_sort Tallini, Luciana R.
collection PubMed
description The Amaryllidaceae family has proven to be a rich source of active compounds, which are characterized by unique skeleton arrangements and a broad spectrum of biological activities. The aim of this work was to perform the first detailed study of the alkaloid constituents of Hippeastrum reticulatum (Amaryllidaceae) and to determine the anti-parasitological and cholinesterase (AChE and BuChE) inhibitory activities of the epimers (6α-hydroxymaritidine and 6β-hydroxymaritidine). Twelve alkaloids were identified in H. reticulatum: eight known alkaloids by GC-MS and four unknown (6α-hydroxymaritidine, 6β-hydroxymaritidine, reticulinine and isoreticulinine) by NMR. The epimer mixture (6α-hydroxymaritidine and 6β-hydroxymaritidine) showed low activity against all protozoan parasites tested and weak AChE-inhibitory activity. Finally, a molecular docking analysis of AChE and BuChE proteins showed that isoreticulinine may be classified as a potential inhibitory molecule since it can be stabilized in the active site through hydrogen bonds, π-π stacking and hydrophobic interactions.
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spelling pubmed-61497992018-11-13 Hippeastrum reticulatum (Amaryllidaceae): Alkaloid Profiling, Biological Activities and Molecular Docking Tallini, Luciana R. Osorio, Edison H. dos Santos, Vanessa Dias Borges, Warley de Souza Kaiser, Marcel Viladomat, Francesc Zuanazzi, José Angelo S. Bastida, Jaume Molecules Article The Amaryllidaceae family has proven to be a rich source of active compounds, which are characterized by unique skeleton arrangements and a broad spectrum of biological activities. The aim of this work was to perform the first detailed study of the alkaloid constituents of Hippeastrum reticulatum (Amaryllidaceae) and to determine the anti-parasitological and cholinesterase (AChE and BuChE) inhibitory activities of the epimers (6α-hydroxymaritidine and 6β-hydroxymaritidine). Twelve alkaloids were identified in H. reticulatum: eight known alkaloids by GC-MS and four unknown (6α-hydroxymaritidine, 6β-hydroxymaritidine, reticulinine and isoreticulinine) by NMR. The epimer mixture (6α-hydroxymaritidine and 6β-hydroxymaritidine) showed low activity against all protozoan parasites tested and weak AChE-inhibitory activity. Finally, a molecular docking analysis of AChE and BuChE proteins showed that isoreticulinine may be classified as a potential inhibitory molecule since it can be stabilized in the active site through hydrogen bonds, π-π stacking and hydrophobic interactions. MDPI 2017-12-09 /pmc/articles/PMC6149799/ /pubmed/29232852 http://dx.doi.org/10.3390/molecules22122191 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Tallini, Luciana R.
Osorio, Edison H.
dos Santos, Vanessa Dias
Borges, Warley de Souza
Kaiser, Marcel
Viladomat, Francesc
Zuanazzi, José Angelo S.
Bastida, Jaume
Hippeastrum reticulatum (Amaryllidaceae): Alkaloid Profiling, Biological Activities and Molecular Docking
title Hippeastrum reticulatum (Amaryllidaceae): Alkaloid Profiling, Biological Activities and Molecular Docking
title_full Hippeastrum reticulatum (Amaryllidaceae): Alkaloid Profiling, Biological Activities and Molecular Docking
title_fullStr Hippeastrum reticulatum (Amaryllidaceae): Alkaloid Profiling, Biological Activities and Molecular Docking
title_full_unstemmed Hippeastrum reticulatum (Amaryllidaceae): Alkaloid Profiling, Biological Activities and Molecular Docking
title_short Hippeastrum reticulatum (Amaryllidaceae): Alkaloid Profiling, Biological Activities and Molecular Docking
title_sort hippeastrum reticulatum (amaryllidaceae): alkaloid profiling, biological activities and molecular docking
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6149799/
https://www.ncbi.nlm.nih.gov/pubmed/29232852
http://dx.doi.org/10.3390/molecules22122191
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