Biosynthesis of Panaxynol and Panaxydol in Panax ginseng

Author： Knispel Nihat Ostrozhenkova Elena Schramek Nicholas Huber Claudia Peña-Rodríguez Luis M. Bonfill Mercedes Palazón Javier Wischmann Gesine Cusidó Rosa M. Eisenreich Wolfgang

Publisher： MDPI

E-ISSN： 1420-3049|18|7|7686-7698

ISSN： 1420-3049

Source： Molecules, Vol.18, Iss.7, 2013-07, pp. : 7686-7698

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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.