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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Format: | info:eu-repo/semantics/article biblioteca |
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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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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 |
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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 |
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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 |
work_keys_str_mv |
AT nihatknispel biosynthesisofpanaxynolandpanaxydolinpanaxginseng AT elenaostrozhenkova biosynthesisofpanaxynolandpanaxydolinpanaxginseng AT nicholasschramek biosynthesisofpanaxynolandpanaxydolinpanaxginseng AT claudiahuber biosynthesisofpanaxynolandpanaxydolinpanaxginseng AT luismanuelpenarodriguez biosynthesisofpanaxynolandpanaxydolinpanaxginseng AT mercedesbonfill biosynthesisofpanaxynolandpanaxydolinpanaxginseng AT javierpalazon biosynthesisofpanaxynolandpanaxydolinpanaxginseng AT gesinewischmann biosynthesisofpanaxynolandpanaxydolinpanaxginseng AT rosamariacusido biosynthesisofpanaxynolandpanaxydolinpanaxginseng AT wolfgangeisenreich biosynthesisofpanaxynolandpanaxydolinpanaxginseng |
_version_ |
1756089272105959424 |