Crinine-type alkaloids from Hippeastrum aulicum and H. calyptratum

An ongoing search for alkaloids in the Amaryllidaceae species using GC MS resulted in the identification of two crinine-type alkaloids, aulicine (1) and 3-O-methyl-epimacowine, (2) from the indigenous Brazilian species Hippeastrum aulicum and Hippeastrum calyptratum, respectively. In addition, two a...

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Autores: de Andrade, Jean Paulo, Guo, Y., Font Bardia, Ma. Mercedes, Calvet Pallàs, Maria Teresa, Dutilh, J. H., Viladomat Meya, Francesc, Codina Mahrer, Carles, Nair, Jerald J., Zuanazzi, José Ângelo Silveira, Bastida Armengol, Jaume
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2014
País:España
Institución:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/169248
Acceso en línea:https://hdl.handle.net/2445/169248
Access Level:acceso abierto
Palabra clave:Alcaloides
Radiocristal·lografia
Alkaloids
X-ray crystallography
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repository_id_str
spelling Crinine-type alkaloids from Hippeastrum aulicum and H. calyptratumde Andrade, Jean PauloGuo, Y.Font Bardia, Ma. MercedesCalvet Pallàs, Maria TeresaDutilh, J. H.Viladomat Meya, FrancescCodina Mahrer, CarlesNair, Jerald J.Zuanazzi, José Ângelo SilveiraBastida Armengol, JaumeAlcaloidesRadiocristal·lografiaAlkaloidsX-ray crystallographyAn ongoing search for alkaloids in the Amaryllidaceae species using GC MS resulted in the identification of two crinine-type alkaloids, aulicine (1) and 3-O-methyl-epimacowine, (2) from the indigenous Brazilian species Hippeastrum aulicum and Hippeastrum calyptratum, respectively. In addition, two alkaloids, 11-oxohaemanthamine (3) and 7-methoxy-O-methyllycorenine (4) were both isolated from H. aulicum. Furthermore, we provide here complete NMR spectroscopic data for the homolycorine analogues nerinine (5) and albomaculine (6). The absolute stereochemistry of the 5,10b-ethano bridge in the crinine variants was determined by circular dichroism and X-ray crystallographic analysis, thus presenting the first direct evidence for the presence of crinine-type alkaloids in the genus Hippeastrum.Elsevier Ltd2014info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttps://hdl.handle.net/2445/169248Articles publicats en revistes (Mineralogia, Petrologia i Geologia Aplicada)reponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglésVersió postprint del document publicat a: https://doi.org/10.1016/j.phytochem.2014.03.007Phytochemistry, 2014, vol. 103, p. 188-195https://doi.org/10.1016/j.phytochem.2014.03.007(c) Elsevier Ltd, 2014info:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/1692482026-05-27T06:46:51Z
dc.title.none.fl_str_mv Crinine-type alkaloids from Hippeastrum aulicum and H. calyptratum
title Crinine-type alkaloids from Hippeastrum aulicum and H. calyptratum
spellingShingle Crinine-type alkaloids from Hippeastrum aulicum and H. calyptratum
de Andrade, Jean Paulo
Alcaloides
Radiocristal·lografia
Alkaloids
X-ray crystallography
title_short Crinine-type alkaloids from Hippeastrum aulicum and H. calyptratum
title_full Crinine-type alkaloids from Hippeastrum aulicum and H. calyptratum
title_fullStr Crinine-type alkaloids from Hippeastrum aulicum and H. calyptratum
title_full_unstemmed Crinine-type alkaloids from Hippeastrum aulicum and H. calyptratum
title_sort Crinine-type alkaloids from Hippeastrum aulicum and H. calyptratum
dc.creator.none.fl_str_mv de Andrade, Jean Paulo
Guo, Y.
Font Bardia, Ma. Mercedes
Calvet Pallàs, Maria Teresa
Dutilh, J. H.
Viladomat Meya, Francesc
Codina Mahrer, Carles
Nair, Jerald J.
Zuanazzi, José Ângelo Silveira
Bastida Armengol, Jaume
author de Andrade, Jean Paulo
author_facet de Andrade, Jean Paulo
Guo, Y.
Font Bardia, Ma. Mercedes
Calvet Pallàs, Maria Teresa
Dutilh, J. H.
Viladomat Meya, Francesc
Codina Mahrer, Carles
Nair, Jerald J.
Zuanazzi, José Ângelo Silveira
Bastida Armengol, Jaume
author_role author
author2 Guo, Y.
Font Bardia, Ma. Mercedes
Calvet Pallàs, Maria Teresa
Dutilh, J. H.
Viladomat Meya, Francesc
Codina Mahrer, Carles
Nair, Jerald J.
Zuanazzi, José Ângelo Silveira
Bastida Armengol, Jaume
author2_role author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Alcaloides
Radiocristal·lografia
Alkaloids
X-ray crystallography
topic Alcaloides
Radiocristal·lografia
Alkaloids
X-ray crystallography
description An ongoing search for alkaloids in the Amaryllidaceae species using GC MS resulted in the identification of two crinine-type alkaloids, aulicine (1) and 3-O-methyl-epimacowine, (2) from the indigenous Brazilian species Hippeastrum aulicum and Hippeastrum calyptratum, respectively. In addition, two alkaloids, 11-oxohaemanthamine (3) and 7-methoxy-O-methyllycorenine (4) were both isolated from H. aulicum. Furthermore, we provide here complete NMR spectroscopic data for the homolycorine analogues nerinine (5) and albomaculine (6). The absolute stereochemistry of the 5,10b-ethano bridge in the crinine variants was determined by circular dichroism and X-ray crystallographic analysis, thus presenting the first direct evidence for the presence of crinine-type alkaloids in the genus Hippeastrum.
publishDate 2014
dc.date.none.fl_str_mv 2014
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/169248
url https://hdl.handle.net/2445/169248
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Versió postprint del document publicat a: https://doi.org/10.1016/j.phytochem.2014.03.007
Phytochemistry, 2014, vol. 103, p. 188-195
https://doi.org/10.1016/j.phytochem.2014.03.007
dc.rights.none.fl_str_mv (c) Elsevier Ltd, 2014
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) Elsevier Ltd, 2014
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Elsevier Ltd
publisher.none.fl_str_mv Elsevier Ltd
dc.source.none.fl_str_mv Articles publicats en revistes (Mineralogia, Petrologia i Geologia Aplicada)
reponame:Dipòsit Digital de la UB
instname:Universidad de Barcelona
instname_str Universidad de Barcelona
reponame_str Dipòsit Digital de la UB
collection Dipòsit Digital de la UB
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,301603

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