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Biosynthesis of Panaxynol and Panaxydol in Panax ginseng
Lehrstuhl für Biochemie, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching, Germany
Laboratorio de Fisiología Vegetal, Facultad de Farmacia, Universidad de Barcelona, 08028 Barcelona, Spain
FloraFarm, Bockhorn, 29664 Walsrode-Bockhorn, Germany
These authors contributed equally to this work.
On sabbatical leave from Centro de Investigación Científica de Yucatán, Mérida, México
* Authors to whom correspondence should be addressed.
Received: 6 May 2013; in revised form: 13 June 2013 / Accepted: 28 June 2013 / Published: 2 July 2013
Abstract: 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.
Keywords: Panax ginseng; Araliaceae; panaxynol; panaxydol; falcarinol; polyyne; crepenynic acid; isotopologue profiling; 13CO2
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MDPI and ACS Style
Knispel, N.; Ostrozhenkova, E.; Schramek, N.; Huber, C.; Peña-Rodríguez, L.M.; Bonfill, M.; Palazón, J.; Wischmann, G.; Cusidó, R.M.; Eisenreich, W. Biosynthesis of Panaxynol and Panaxydol in Panax ginseng. Molecules 2013, 18, 7686-7698.
Knispel N, Ostrozhenkova E, Schramek N, Huber C, Peña-Rodríguez LM, Bonfill M, Palazón J, Wischmann G, Cusidó RM, Eisenreich W. Biosynthesis of Panaxynol and Panaxydol in Panax ginseng. Molecules. 2013; 18(7):7686-7698.
Knispel, Nihat; Ostrozhenkova, Elena; Schramek, Nicholas; Huber, Claudia; Peña-Rodríguez, Luis M.; Bonfill, Mercedes; Palazón, Javier; Wischmann, Gesine; Cusidó, Rosa M.; Eisenreich, Wolfgang. 2013. "Biosynthesis of Panaxynol and Panaxydol in Panax ginseng." Molecules 18, no. 7: 7686-7698.