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 journal

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) 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.proposal.eng.fl_str_mv	Acetylcholinesterase Alkaloids Alzheimer’s disease Amaryllidaceae Galanthamine Rauhia
topic	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	2022-12-16
dc.date.accessioned.none.fl_str_mv	2023-10-17T20:48:27Z
dc.date.available.none.fl_str_mv	2023-10-17T20:48:27Z
dc.type.none.fl_str_mv	Artículo de revista
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dc.identifier.citation.none.fl_str_mv	Tallini, L.R.; Osorio, E.H.; Berkov, S.; Torras-Claveria, L.; Rodríguez-Escobar, M.L.; Viladomat, F.; Meerow, A.W.; Bastida, J. Chemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae). Plants 2022, 11, 3549. https://doi.org/10.3390/ plants11243549
dc.identifier.issn.none.fl_str_mv	2223-7747
dc.identifier.uri.none.fl_str_mv	https://hdl.handle.net/20.500.12313/3838
identifier_str_mv	Tallini, L.R.; Osorio, E.H.; Berkov, S.; Torras-Claveria, L.; Rodríguez-Escobar, M.L.; Viladomat, F.; Meerow, A.W.; Bastida, J. Chemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae). Plants 2022, 11, 3549. https://doi.org/10.3390/ plants11243549 2223-7747
url	https://hdl.handle.net/20.500.12313/3838
dc.language.iso.none.fl_str_mv	eng
language	eng
dc.relation.citationendpage.none.fl_str_mv	13
dc.relation.citationissue.none.fl_str_mv	3549
dc.relation.citationstartpage.none.fl_str_mv	1
dc.relation.citationvolume.none.fl_str_mv	11
dc.relation.ispartofjournal.none.fl_str_mv	Plants
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Alkaloids of Amaryllidaceae as inhibitors of cholinesterases (AChEs and BChEs): An integrated bioguided study. Phytochem. Anal. 2018, 29, 217–227 Trujillo-Chacón, L.M.; Alarcón-Enos, J.E.; Céspedes-Acuña, C.L.; Bustamante, L.; Baeza, M.; López, M.G.; Fernández-Mendívil, C.; Cabezas, F.; Pastene—Navarrete, E.R. Neuroprotective activity of isoquinoline alkaloids from Chilean Amaryllidaceae plants against oxidative stress-induced cytotoxicity on human neuroblastoma SH-SY5Y cells and mouse hippocampal slice culture. Food Chem. Toxicol. 2019, 132, 110665 Moreno, R.; Tallini, L.R.; Salazar, C.; Osorio, E.H.; Montero, E.; Bastida, J.; Oleas, N.H.; León, K.A. Chemical profiling and cholinesrerase inhibitory activity of five Phaedranassa Herb. (Amaryllidaceae) species from Ecuador. Molecules 2020, 25, 2092 Acosta, K.L.; Inca, A.; Tallini, L.R.; Osorio, E.H.; Robles, J.; Bastida, J.; Oleas, N.H. Alkaloids of Phaedranassa dubia (Kunth) J.F. 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Lett. 2013, 4, 1091–1096 Sierra, K.; de Andrade, J.P.; Tallini, L.R.; Osorio, E.H.; Yañéz, O.; Osorio, M.I.; Oleas, N.H.; García-Beltrán, O.; de Borges, W.S.; Bastida, J.; et al. In vitro and in silico analysis of galanthine from Zephyranthes carinata as an inhibitor of acetylcholinesterase. Biomed. Pharmacother. 2022, 150, 113016 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. 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spelling	Tallini, Luciana R.2f4f4ff0-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 L.1267d0d3-247e-43c8-9cb7-315bcfad9c7f-1Viladomat, Francesc894d5ae3-1542-41a9-a0cd-2d5597df7d19-1Meerow, Alan W.f5860503-b817-4a6e-ac0f-0141af7ecf64-1Bastida, Jaume00ea29d6-11a2-48bd-bc9e-2dd48a2bc06e-12023-10-17T20:48:27Z2023-10-17T20:48:27Z2022-12-16Plant 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 galanthamineapplication/pdfTallini, L.R.; Osorio, E.H.; Berkov, S.; Torras-Claveria, L.; Rodríguez-Escobar, M.L.; Viladomat, F.; Meerow, A.W.; Bastida, J. Chemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae). Plants 2022, 11, 3549. https://doi.org/10.3390/ plants112435492223-7747https://hdl.handle.net/20.500.12313/3838engSuiza133549111PlantsWorld 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. Prod. 2020, 83, 770–803Feher, M.; Schimidt, J.M. Property distributions: Differences between drugs, natural products, and molecules from combinatorial chemistry. J. Chem. Inf. Comput. Sci. 2003, 43, 218–227Lu, J.-J.; Bao, J.-L.; Chen, X.-P.; Huang, M.; Wang, Y.-T. Alkaloids isolated from natural herbs as the anticancer agents. Evid. Based. Compl. Alt. 2012, 2012, 485042Bastida, J.; Lavilla, R.; Viladomat, F. Chemical and biological aspects of Narcissus alkaloids. In The Alkaloids: Chemistry and Physiology; Cordell, G.A., Ed.; Elsevier: Amsterdam, The Netherlands, 2006; Volume 63, pp. 87–179Meerow, A.W.; Snijman, D.A. Amaryllidaceae. In Families and Genera of Vascular Plants; Kubitzki, K., Ed.; Springer: Berlin, Germany, 1998; Volume 3, pp. 83–110Konrath, E.L.; Passos, C.D.S.; Klein-Júnior, L.C.; Henriques, A.T. Alkaloids as a source of potential anticholinesterase inhibitors for the treatment of Alzheimer’s disease. J. Pharm. Pharmacol. 2013, 65, 1701–1725Traub, H.P. 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Chem. 1999, 19, 1639–1662This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https:// creativecommons.org/licenses/by/ 4.0/).info:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2Atribución 4.0 Internacional (CC BY 4.0)https://creativecommons.org/licenses/by-nc-nd/4.0/https://www.mdpi.com/2223-7747/11/24/3549AcetylcholinesteraseAlkaloidsAlzheimer’s diseaseAmaryllidaceaeGalanthamineRauhiaChemical survey of three species of the Genus rauhia traub (Amaryllidaceae)Artículo de revistahttp://purl.org/coar/resource_type/c_6501http://purl.org/coar/resource_type/c_2df8fbb1http://purl.org/coar/version/c_970fb48d4fbd8a85Textinfo:eu-repo/semantics/articlehttp://purl.org/redcol/resource_type/ARTinfo:eu-repo/semantics/publishedVersionPublicationTEXTChemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae) - plants-11-03549.pdf.txtChemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae) - plants-11-03549.pdf.txtExtracted texttext/plain4742https://repositorio.unibague.edu.co/bitstreams/d8a7c2ca-b62c-47a9-9863-43437be2f73c/downloadc1b290ec99b2cf54d5a83408a0931155MD53THUMBNAILChemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae) - plants-11-03549.pdf.jpgChemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae) - plants-11-03549.pdf.jpgGenerated Thumbnailimage/jpeg13776https://repositorio.unibague.edu.co/bitstreams/032ef354-f404-483b-bcc4-c5bbee30d6da/download1e9be5577b9d0be870dd09a2c8994619MD54LICENSElicense.txtlicense.txttext/plain; charset=utf-8134https://repositorio.unibague.edu.co/bitstreams/a6d321ba-eac4-49ec-8f5d-e9d29b1fea42/download2fa3e590786b9c0f3ceba1b9656b7ac3MD52ORIGINALChemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae) - plants-11-03549.pdfChemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae) - plants-11-03549.pdfapplication/pdf94683https://repositorio.unibague.edu.co/bitstreams/c5344b13-06c1-4e43-8606-07fa6e91fc21/download3d6b5ed11e187fd6cf3d4bcc017d5e2dMD5120.500.12313/3838oai:repositorio.unibague.edu.co:20.500.12313/38382023-10-18 03:00:38.418https://creativecommons.org/licenses/by-nc-nd/4.0/This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https:// creativecommons.org/licenses/by/ 4.0/).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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