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 [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.

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Main Authors: Nihat Knispel, Elena Ostrozhenkova, Nicholas Schramek, Claudia Huber, Luis Manuel Peña Rodríguez, Mercedes Bonfill, Javier Palazon, Gesine Wischmann, Rosa Maria Cusido, Wolfgang Eisenreich
Format: info:eu-repo/semantics/article biblioteca
Language:eng
Subjects:info:eu-repo/classification/Autores/PANAX GINSENG, info:eu-repo/classification/Autores/ARALIACEAE, info:eu-repo/classification/Autores/PANAXYNOL, info:eu-repo/classification/Autores/PANAXYDOL, info:eu-repo/classification/Autores/FALCARINOL, info:eu-repo/classification/Autores/POLYYNE, info:eu-repo/classification/Autores/CREPENYNIC ACID, info:eu-repo/classification/Autores/ISOTOPOLOGUE PROFILING, info:eu-repo/classification/Autores/13CO2, info:eu-repo/classification/cti/2, info:eu-repo/classification/cti/24, info:eu-repo/classification/cti/2407, info:eu-repo/classification/cti/240702,
Online Access:http://cicy.repositorioinstitucional.mx/jspui/handle/1003/1611
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spelling dig-cicy-1003-16112019-12-05T22:32:44Z Biosynthesis of panaxynol and panaxydol in Panax ginseng Nihat Knispel Elena Ostrozhenkova Nicholas Schramek Claudia Huber Luis Manuel Peña Rodríguez Mercedes Bonfill Javier Palazon Gesine Wischmann Rosa Maria Cusido Wolfgang Eisenreich 2013 info:eu-repo/semantics/article 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. info:eu-repo/classification/Autores/PANAX GINSENG info:eu-repo/classification/Autores/ARALIACEAE info:eu-repo/classification/Autores/PANAXYNOL info:eu-repo/classification/Autores/PANAXYDOL info:eu-repo/classification/Autores/FALCARINOL info:eu-repo/classification/Autores/POLYYNE info:eu-repo/classification/Autores/CREPENYNIC ACID info:eu-repo/classification/Autores/ISOTOPOLOGUE PROFILING info:eu-repo/classification/Autores/13CO2 info:eu-repo/classification/cti/2 info:eu-repo/classification/cti/24 info:eu-repo/classification/cti/2407 info:eu-repo/classification/cti/240702 info:eu-repo/classification/cti/240702 Molecules, 18(7), 7686-7698, 2013 http://cicy.repositorioinstitucional.mx/jspui/handle/1003/1611 info:eu-repo/semantics/datasetDOI/10.3390/molecules18077686  info:eu-repo/semantics/openAccess eng citation:Knispel, N., Ostrozhenkova, E., Schramek, N., Huber, C., Peña-Rodríguez, L., Bonfill, M., ... & Eisenreich, W. (2013). Biosynthesis of Panaxynol and Panaxydol in Panax ginseng. Molecules, 18(7), 7686-7698. http://creativecommons.org/licenses/by-nc-nd/4.0 info:eu-repo/semantics/publishedVersion application/pdf
institution CICY
collection DSpace
country México
countrycode MX
component Bibliográfico
access En linea
databasecode dig-cicy
tag biblioteca
region America del Norte
libraryname Biblioteca del CICY
language eng
topic info:eu-repo/classification/Autores/PANAX GINSENG
info:eu-repo/classification/Autores/ARALIACEAE
info:eu-repo/classification/Autores/PANAXYNOL
info:eu-repo/classification/Autores/PANAXYDOL
info:eu-repo/classification/Autores/FALCARINOL
info:eu-repo/classification/Autores/POLYYNE
info:eu-repo/classification/Autores/CREPENYNIC ACID
info:eu-repo/classification/Autores/ISOTOPOLOGUE PROFILING
info:eu-repo/classification/Autores/13CO2
info:eu-repo/classification/cti/2
info:eu-repo/classification/cti/24
info:eu-repo/classification/cti/2407
info:eu-repo/classification/cti/240702
info:eu-repo/classification/cti/240702
info:eu-repo/classification/Autores/PANAX GINSENG
info:eu-repo/classification/Autores/ARALIACEAE
info:eu-repo/classification/Autores/PANAXYNOL
info:eu-repo/classification/Autores/PANAXYDOL
info:eu-repo/classification/Autores/FALCARINOL
info:eu-repo/classification/Autores/POLYYNE
info:eu-repo/classification/Autores/CREPENYNIC ACID
info:eu-repo/classification/Autores/ISOTOPOLOGUE PROFILING
info:eu-repo/classification/Autores/13CO2
info:eu-repo/classification/cti/2
info:eu-repo/classification/cti/24
info:eu-repo/classification/cti/2407
info:eu-repo/classification/cti/240702
info:eu-repo/classification/cti/240702
spellingShingle info:eu-repo/classification/Autores/PANAX GINSENG
info:eu-repo/classification/Autores/ARALIACEAE
info:eu-repo/classification/Autores/PANAXYNOL
info:eu-repo/classification/Autores/PANAXYDOL
info:eu-repo/classification/Autores/FALCARINOL
info:eu-repo/classification/Autores/POLYYNE
info:eu-repo/classification/Autores/CREPENYNIC ACID
info:eu-repo/classification/Autores/ISOTOPOLOGUE PROFILING
info:eu-repo/classification/Autores/13CO2
info:eu-repo/classification/cti/2
info:eu-repo/classification/cti/24
info:eu-repo/classification/cti/2407
info:eu-repo/classification/cti/240702
info:eu-repo/classification/cti/240702
info:eu-repo/classification/Autores/PANAX GINSENG
info:eu-repo/classification/Autores/ARALIACEAE
info:eu-repo/classification/Autores/PANAXYNOL
info:eu-repo/classification/Autores/PANAXYDOL
info:eu-repo/classification/Autores/FALCARINOL
info:eu-repo/classification/Autores/POLYYNE
info:eu-repo/classification/Autores/CREPENYNIC ACID
info:eu-repo/classification/Autores/ISOTOPOLOGUE PROFILING
info:eu-repo/classification/Autores/13CO2
info:eu-repo/classification/cti/2
info:eu-repo/classification/cti/24
info:eu-repo/classification/cti/2407
info:eu-repo/classification/cti/240702
info:eu-repo/classification/cti/240702
Nihat Knispel
Elena Ostrozhenkova
Nicholas Schramek
Claudia Huber
Luis Manuel Peña Rodríguez
Mercedes Bonfill
Javier Palazon
Gesine Wischmann
Rosa Maria Cusido
Wolfgang Eisenreich
Biosynthesis of panaxynol and panaxydol in Panax 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.
format info:eu-repo/semantics/article
topic_facet info:eu-repo/classification/Autores/PANAX GINSENG
info:eu-repo/classification/Autores/ARALIACEAE
info:eu-repo/classification/Autores/PANAXYNOL
info:eu-repo/classification/Autores/PANAXYDOL
info:eu-repo/classification/Autores/FALCARINOL
info:eu-repo/classification/Autores/POLYYNE
info:eu-repo/classification/Autores/CREPENYNIC ACID
info:eu-repo/classification/Autores/ISOTOPOLOGUE PROFILING
info:eu-repo/classification/Autores/13CO2
info:eu-repo/classification/cti/2
info:eu-repo/classification/cti/24
info:eu-repo/classification/cti/2407
info:eu-repo/classification/cti/240702
info:eu-repo/classification/cti/240702
author Nihat Knispel
Elena Ostrozhenkova
Nicholas Schramek
Claudia Huber
Luis Manuel Peña Rodríguez
Mercedes Bonfill
Javier Palazon
Gesine Wischmann
Rosa Maria Cusido
Wolfgang Eisenreich
author_facet Nihat Knispel
Elena Ostrozhenkova
Nicholas Schramek
Claudia Huber
Luis Manuel Peña Rodríguez
Mercedes Bonfill
Javier Palazon
Gesine Wischmann
Rosa Maria Cusido
Wolfgang Eisenreich
author_sort Nihat Knispel
title Biosynthesis of panaxynol and panaxydol in Panax 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
url http://cicy.repositorioinstitucional.mx/jspui/handle/1003/1611
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