Chemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae)

Plant biodiversity is an important source of compounds with medicinal properties. The alkaloid galanthamine, first isolated from Galanthus woronowii (Amaryllidaceae), is approved by the FDA for the palliative treatment of mild to moderate Alzheimer’s disease due to its acetylcholinesterase (AChE) in...

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Autores:: Tallini, Luciana R
Osorio, Edison H.
Berkov, Strahil
Torras-Claveria, Laura
Rodríguez-Escobar, María L
Viladomat, Francesc
Meerow, Alan W.
Bastida, Jaume

Tipo de recurso:: Article of investigation

Fecha de publicación:: 2022

Institución:: Universidad de Ibagué

Repositorio:: Repositorio Universidad de Ibagué

Idioma:: eng

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dc.title.eng.fl_str_mv	Chemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae)
title	Chemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae)
spellingShingle	Chemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae) Rauhia Traub (Amaryllidaceae) - Encuesta química Acetylcholinesterase Alkaloids Alzheimer’s disease Amaryllidaceae Galanthamine Rauhia
title_short	Chemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae)
title_full	Chemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae)
title_fullStr	Chemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae)
title_full_unstemmed	Chemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae)
title_sort	Chemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae)
dc.creator.fl_str_mv	Tallini, Luciana R Osorio, Edison H. Berkov, Strahil Torras-Claveria, Laura Rodríguez-Escobar, María L Viladomat, Francesc Meerow, Alan W. Bastida, Jaume
dc.contributor.author.none.fl_str_mv	Tallini, Luciana R Osorio, Edison H. Berkov, Strahil Torras-Claveria, Laura Rodríguez-Escobar, María L Viladomat, Francesc Meerow, Alan W. Bastida, Jaume
dc.subject.armarc.none.fl_str_mv	Rauhia Traub (Amaryllidaceae) - Encuesta química
topic	Rauhia Traub (Amaryllidaceae) - Encuesta química Acetylcholinesterase Alkaloids Alzheimer’s disease Amaryllidaceae Galanthamine Rauhia
dc.subject.proposal.eng.fl_str_mv	Acetylcholinesterase Alkaloids Alzheimer’s disease Amaryllidaceae Galanthamine Rauhia
description	Plant biodiversity is an important source of compounds with medicinal properties. The alkaloid galanthamine, first isolated from Galanthus woronowii (Amaryllidaceae), is approved by the FDA for the palliative treatment of mild to moderate Alzheimer’s disease due to its acetylcholinesterase (AChE) inhibitory activity. Obtaining this active pharmaceutical ingredient, still sourced on an industrial scale from the Amaryllidaceae species, is a challenge for pharmaceutical companies due to its low natural yield and the high cost of its synthesis. The aim of this work was to determine the alkaloid profile of three different Rauhia (Amaryllidaceae) species collected in Peru, and to assess the potential application of their extracts for the treatment of Alzheimer’s disease. The alkaloids were identified by gas chromatography coupled to mass spectrometry (GC-MS), and the AChE inhibitory activity of the extracts was analyzed. Thirty compounds were quantified from the Rauhia species, the R. multiflora extract being the most interesting due to its high diversity of galanthamine-type structures. The R. multiflora extract was also the most active against AChE, with the half maximal inhibitory concentration (IC50) values of 0.17 ± 0.02 μg·mL−1 in comparison with the IC50 values of 0.53 ± 0.12 μg·mL−1 for galanthamine, used as a reference. Computational experiments were carried out on the activity of the galanthamine-type alkaloids identified in R. multiflora toward five different human AChE structures. The simulation of the molecules 3-O-acetylgalanthamine, 3-O-acetylsanguinine, narwedine, and lycoraminone on the 4EY6 crystal structure theoretically showed a higher inhibition of hAChE and different interactions with the active site compared to galanthamine. In conclusion, the results of this first alkaloid profiling of the Rauhia species indicate that R. multiflora is an important natural source of galanthamine-type structures and could be used as a model for the development of biotechnological tools necessary to advance the sustainable production of galanthamine.
publishDate	2022
dc.date.issued.none.fl_str_mv	2022-12
dc.date.accessioned.none.fl_str_mv	2025-08-21T21:47:31Z
dc.date.available.none.fl_str_mv	2025-08-21T21:47:31Z
dc.type.none.fl_str_mv	Artículo de revista
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dc.identifier.citation.none.fl_str_mv	Tallini, L., Osorio, E., Berkov, S., Torras-Claveria, L., Rodríguez-Escobar, M., Viladomat, F., Meerow, A. y Meerow, A. (2022). Chemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae). Plants, 11(24), 3549. DOI: 10.3390/plants11243549
dc.identifier.doi.none.fl_str_mv	10.3390/plants11243549
dc.identifier.issn.none.fl_str_mv	22237747
dc.identifier.uri.none.fl_str_mv	https://hdl.handle.net/20.500.12313/5517
identifier_str_mv	Tallini, L., Osorio, E., Berkov, S., Torras-Claveria, L., Rodríguez-Escobar, M., Viladomat, F., Meerow, A. y Meerow, A. (2022). Chemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae). Plants, 11(24), 3549. DOI: 10.3390/plants11243549 10.3390/plants11243549 22237747
url	https://hdl.handle.net/20.500.12313/5517
dc.language.iso.none.fl_str_mv	eng
language	eng
dc.relation.citationissue.none.fl_str_mv	24
dc.relation.citationstartpage.none.fl_str_mv	3549
dc.relation.citationvolume.none.fl_str_mv	11
dc.relation.ispartofjournal.none.fl_str_mv	Plants
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Torras-Claveria, L.; Berkov, S.; Codina, C.; Viladomat, F.; Bastida, J. Daffodils as potential crops of galanthamine. Assessment of more than 100 ornamental varieties for their alkaloid content and acetylcholinesterase inhibitory activity. Ind. Crops Prod. 2013, 43, 237–244. Morris, G.M.; Huey, R.; Lindstrom, W.; Sanner, M.F.; Belew, R.K.; Goodsell, D.S.; Olson, A.J. AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. J. Comput. Chem. 2009, 30, 2785–2791. Schrödinger Release 2022-3: Maestro; Schrödinger, Inc.: New York, NY, USA, 2021. Morris, G.M.; Goodsell, D.S.; Halliday, R.S.; Huey, R.; Hart, W.E.; Belew, R.K.; Olson, A.J. Automated docking using a Lamarckinan genetic algorithm and an empirical binding free energy function. J. Comput. Chem. 1999, 19, 1639–1662.
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spelling	Tallini, Luciana R2f4f4ff0-b0e3-4368-a41a-43b019651013-1Osorio, Edison H.087e0c0b-d49f-4915-b7fa-272d785c30af-1Berkov, Strahilf3ebf785-30b0-49d2-b1b3-d4070d85a0d2-1Torras-Claveria, Laurabe5ccdcb-b011-4d96-8194-9d68ede80dd7-1Rodríguez-Escobar, María L1267d0d3-247e-43c8-9cb7-315bcfad9c7f-1Viladomat, Francesc894d5ae3-1542-41a9-a0cd-2d5597df7d19-1Meerow, Alan W.f5860503-b817-4a6e-ac0f-0141af7ecf64-1Bastida, Jaume00ea29d6-11a2-48bd-bc9e-2dd48a2bc06e-12025-08-21T21:47:31Z2025-08-21T21:47:31Z2022-12Plant biodiversity is an important source of compounds with medicinal properties. The alkaloid galanthamine, first isolated from Galanthus woronowii (Amaryllidaceae), is approved by the FDA for the palliative treatment of mild to moderate Alzheimer’s disease due to its acetylcholinesterase (AChE) inhibitory activity. Obtaining this active pharmaceutical ingredient, still sourced on an industrial scale from the Amaryllidaceae species, is a challenge for pharmaceutical companies due to its low natural yield and the high cost of its synthesis. The aim of this work was to determine the alkaloid profile of three different Rauhia (Amaryllidaceae) species collected in Peru, and to assess the potential application of their extracts for the treatment of Alzheimer’s disease. The alkaloids were identified by gas chromatography coupled to mass spectrometry (GC-MS), and the AChE inhibitory activity of the extracts was analyzed. Thirty compounds were quantified from the Rauhia species, the R. multiflora extract being the most interesting due to its high diversity of galanthamine-type structures. The R. multiflora extract was also the most active against AChE, with the half maximal inhibitory concentration (IC50) values of 0.17 ± 0.02 μg·mL−1 in comparison with the IC50 values of 0.53 ± 0.12 μg·mL−1 for galanthamine, used as a reference. Computational experiments were carried out on the activity of the galanthamine-type alkaloids identified in R. multiflora toward five different human AChE structures. The simulation of the molecules 3-O-acetylgalanthamine, 3-O-acetylsanguinine, narwedine, and lycoraminone on the 4EY6 crystal structure theoretically showed a higher inhibition of hAChE and different interactions with the active site compared to galanthamine. In conclusion, the results of this first alkaloid profiling of the Rauhia species indicate that R. multiflora is an important natural source of galanthamine-type structures and could be used as a model for the development of biotechnological tools necessary to advance the sustainable production of galanthamine.application/pdfTallini, L., Osorio, E., Berkov, S., Torras-Claveria, L., Rodríguez-Escobar, M., Viladomat, F., Meerow, A. y Meerow, A. (2022). Chemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae). Plants, 11(24), 3549. DOI: 10.3390/plants1124354910.3390/plants1124354922237747https://hdl.handle.net/20.500.12313/5517engMDPISuiza24354911PlantsWorld Health Organization–Biodiversity and Health. Available online: https://www.who.int/news-room/fact-sheets/detail/biodiversity-and-health (accessed on 25 July 2022).Newman, D.; Cragg, G.M. Natural products as sources of new drugs over the nearly four decades from 01/1981 to 09/2019. J. Nat. 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Chem. 1999, 19, 1639–1662.© 2022 by the authors.info:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2Atribución-NoComercial 4.0 Internacional (CC BY-NC 4.0)https://creativecommons.org/licenses/by-nc/4.0/https://www.mdpi.com/2223-7747/11/24/3549Rauhia Traub (Amaryllidaceae) - Encuesta químicaAcetylcholinesteraseAlkaloidsAlzheimer’s diseaseAmaryllidaceaeGalanthamineRauhiaChemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae)Artículo de revistahttp://purl.org/coar/resource_type/c_2df8fbb1http://purl.org/coar/version/c_970fb48d4fbd8a85Textinfo:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionPublicationORIGINALArtículo.pdfArtículo.pdfapplication/pdf232876https://repositorio.unibague.edu.co/bitstreams/7a669028-533b-404d-b789-1bfe122d044f/download6a4ff52db40e7d364df1ebd69c020fa3MD51LICENSElicense.txtlicense.txttext/plain; charset=utf-8134https://repositorio.unibague.edu.co/bitstreams/4319d622-077f-43d4-89c9-65d339f8787f/download2fa3e590786b9c0f3ceba1b9656b7ac3MD52TEXTArtículo.pdf.txtArtículo.pdf.txtExtracted texttext/plain8220https://repositorio.unibague.edu.co/bitstreams/04788093-44f7-4dea-93d7-d26d05ea44bb/download13eb0bac136fd618a5c3da4b265d33c4MD53THUMBNAILArtículo.pdf.jpgArtículo.pdf.jpgIM Thumbnailimage/jpeg26790https://repositorio.unibague.edu.co/bitstreams/721fbc21-f1df-462f-be63-477cf1f7b7dd/downloadf75331d31e4ddd063ea4e2dbf757c1abMD5420.500.12313/5517oai:repositorio.unibague.edu.co:20.500.12313/55172025-08-22 03:03:09.93https://creativecommons.org/licenses/by-nc/4.0/© 2022 by the authors.https://repositorio.unibague.edu.coRepositorio Institucional Universidad de Ibaguébdigital@metabiblioteca.comQ3JlYXRpdmUgQ29tbW9ucyBBdHRyaWJ1dGlvbi1Ob25Db21tZXJjaWFsLU5vRGVyaXZhdGl2ZXMgNC4wIEludGVybmF0aW9uYWwgTGljZW5zZQ0KaHR0cHM6Ly9jcmVhdGl2ZWNvbW1vbnMub3JnL2xpY2Vuc2VzL2J5LW5jLW5kLzQuMC8=

Chemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae)

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