Biosynthesis of panaxynol and panaxydol in Panax ginseng

The natural formation of the bioactive C17-polyacetylenes (−)-(R)-panaxynol and panaxydol was analyzed by 13C-labeling experiments. For this purpose, plants of Panax ginseng were supplied with 13CO2 under field conditions or, alternatively, sterile root cultures of P. ginseng were supplemented with...

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Autores: Knispel, Nihat, Ostrozhenkova, Elena, Schramek, Nicholas, Huber, Claudia, Peña-Rodríguez, Luis M., Bonfill Baldrich, Ma. Mercedes, Palazón Barandela, Javier, Wischmann, Gesine, Cusidó Vidal, Rosa M., Eisenreich, Wolfgang
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2013
País:España
Institución:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/52923
Acceso en línea:https://hdl.handle.net/2445/52923
Access Level:acceso abierto
Palabra clave:Biosíntesi
Ginseng
Biosynthesis
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spelling Biosynthesis of panaxynol and panaxydol in Panax ginsengKnispel, NihatOstrozhenkova, ElenaSchramek, NicholasHuber, ClaudiaPeña-Rodríguez, Luis M.Bonfill Baldrich, Ma. MercedesPalazón Barandela, JavierWischmann, GesineCusidó Vidal, Rosa M.Eisenreich, WolfgangBiosíntesiGinsengBiosynthesisGinsengThe natural formation of the bioactive C17-polyacetylenes (−)-(R)-panaxynol and panaxydol was analyzed by 13C-labeling experiments. For this purpose, plants of Panax ginseng were supplied with 13CO2 under field conditions or, alternatively, sterile root cultures of P. ginseng were supplemented with [U-13C6]glucose. The polyynes were isolated from the labeled roots or hairy root cultures, respectively, and analyzed by quantitative NMR spectroscopy. The same mixtures of eight doubly 13C-labeled isotopologues and one single labeled isotopologue were observed in the C17-polyacetylenes obtained from the two experiments. The polyketide-type labeling pattern is in line with the biosynthetic origin of the compounds via decarboxylation of fatty acids, probably of crepenynic acid. The 13C-study now provides experimental evidence for the biosynthesis of panaxynol and related polyacetylenes in P. ginseng under in planta conditions as well as in root cultures. The data also show that 13CO2 experiments under field conditions are useful to elucidate the biosynthetic pathways of metabolites, including those from roots.MDPI Publishing2013info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://hdl.handle.net/2445/52923Articles publicats en revistes (Biologia, Sanitat i Medi Ambient)reponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglésReproducció del document publicat a: http://dx.doi.org/10.3390/molecules18077686Molecules, 2013, vol. 18, p. 7686-7698http://dx.doi.org/10.3390/molecules18077686cc-by (c) Knispel, Nihat et al., 2013http://creativecommons.org/licenses/by/3.0/esinfo:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/529232026-05-27T06:46:51Z
dc.title.none.fl_str_mv Biosynthesis of panaxynol and panaxydol in Panax ginseng
title Biosynthesis of panaxynol and panaxydol in Panax ginseng
spellingShingle Biosynthesis of panaxynol and panaxydol in Panax ginseng
Knispel, Nihat
Biosíntesi
Ginseng
Biosynthesis
Ginseng
title_short Biosynthesis of panaxynol and panaxydol in Panax ginseng
title_full Biosynthesis of panaxynol and panaxydol in Panax ginseng
title_fullStr Biosynthesis of panaxynol and panaxydol in Panax ginseng
title_full_unstemmed Biosynthesis of panaxynol and panaxydol in Panax ginseng
title_sort Biosynthesis of panaxynol and panaxydol in Panax ginseng
dc.creator.none.fl_str_mv Knispel, Nihat
Ostrozhenkova, Elena
Schramek, Nicholas
Huber, Claudia
Peña-Rodríguez, Luis M.
Bonfill Baldrich, Ma. Mercedes
Palazón Barandela, Javier
Wischmann, Gesine
Cusidó Vidal, Rosa M.
Eisenreich, Wolfgang
author Knispel, Nihat
author_facet Knispel, Nihat
Ostrozhenkova, Elena
Schramek, Nicholas
Huber, Claudia
Peña-Rodríguez, Luis M.
Bonfill Baldrich, Ma. Mercedes
Palazón Barandela, Javier
Wischmann, Gesine
Cusidó Vidal, Rosa M.
Eisenreich, Wolfgang
author_role author
author2 Ostrozhenkova, Elena
Schramek, Nicholas
Huber, Claudia
Peña-Rodríguez, Luis M.
Bonfill Baldrich, Ma. Mercedes
Palazón Barandela, Javier
Wischmann, Gesine
Cusidó Vidal, Rosa M.
Eisenreich, Wolfgang
author2_role author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Biosíntesi
Ginseng
Biosynthesis
Ginseng
topic Biosíntesi
Ginseng
Biosynthesis
Ginseng
description The natural formation of the bioactive C17-polyacetylenes (−)-(R)-panaxynol and panaxydol was analyzed by 13C-labeling experiments. For this purpose, plants of Panax ginseng were supplied with 13CO2 under field conditions or, alternatively, sterile root cultures of P. ginseng were supplemented with [U-13C6]glucose. The polyynes were isolated from the labeled roots or hairy root cultures, respectively, and analyzed by quantitative NMR spectroscopy. The same mixtures of eight doubly 13C-labeled isotopologues and one single labeled isotopologue were observed in the C17-polyacetylenes obtained from the two experiments. The polyketide-type labeling pattern is in line with the biosynthetic origin of the compounds via decarboxylation of fatty acids, probably of crepenynic acid. The 13C-study now provides experimental evidence for the biosynthesis of panaxynol and related polyacetylenes in P. ginseng under in planta conditions as well as in root cultures. The data also show that 13CO2 experiments under field conditions are useful to elucidate the biosynthetic pathways of metabolites, including those from roots.
publishDate 2013
dc.date.none.fl_str_mv 2013
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/52923
url https://hdl.handle.net/2445/52923
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Reproducció del document publicat a: http://dx.doi.org/10.3390/molecules18077686
Molecules, 2013, vol. 18, p. 7686-7698
http://dx.doi.org/10.3390/molecules18077686
dc.rights.none.fl_str_mv cc-by (c) Knispel, Nihat et al., 2013
http://creativecommons.org/licenses/by/3.0/es
info:eu-repo/semantics/openAccess
rights_invalid_str_mv cc-by (c) Knispel, Nihat et al., 2013
http://creativecommons.org/licenses/by/3.0/es
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv MDPI Publishing
publisher.none.fl_str_mv MDPI Publishing
dc.source.none.fl_str_mv Articles publicats en revistes (Biologia, Sanitat i Medi Ambient)
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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