Biosynthesis of Panaxynol and Panaxydol in Panax ginseng

Knispel, Nihat; Ostrozhenkova, Elena; Schramek, Nicholas; Huber, Claudia; Peña‐Rodríguez, Luis M.; Bonfill, Mercedes; Palazón, Javier; Wischmann, Gesine; Cusidó, Rosa M.; Eisenreich, Wolfgang

doi:10.3390/molecules18077686

Cited by 21 publications

(20 citation statements)

References 56 publications

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“…1). Early intermediates of this pathway have been identified by radiochemical studies (Barley et al, 1988;Knispel et al, 2013), and the pathway has been examined in diverse campanulid lineages (Lee et al, 1998;Cahoon et al, 2003;Carlsson et al, 2004;Nam and Kappock, 2007;Busta et al, 2018). Linoleic acid is converted to crepenynic acid by installing the first acetylenic bond in the D 12 position (the 12 th carbon relative to the fatty acid head group; this notation is used consistently throughout).…”

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confidence: 99%

FAD2 Gene Radiation and Positive Selection Contributed to Polyacetylene Metabolism Evolution in Campanulids

et al. 2019

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Polyacetylenes (PAs) are bioactive, specialized plant defense compounds produced by some species in the eudicot clade campanulids. Early steps of PA biosynthesis are catalyzed by Fatty Acid Desaturase 2 (FAD2). Canonical FAD2s catalyze desaturation, but divergent forms can catalyze hydroxylation, conjugation, acetylenation, and epoxygenation. These alternate reactions give rise to valuable unusual fatty acids, including the precursors to PAs. The extreme functional diversity of FAD2 enzymes and the origin of PA biosynthesis are poorly understood from an evolutionary perspective. We focus here on the evolution of the FAD2 gene family. We uncovered a core eudicot-wide gene duplication event giving rise to two lineages: FAD2a and FAD2-b. Independent neofunctionalizations in both lineages have resulted in functionally diverse FAD2-LIKEs involved in unusual fatty acid biosynthesis. We found significantly accelerated rates of molecular evolution in FAD2-LIKEs and use this metric to provide a list of uncharacterized candidates for further exploration of FAD2 functional diversity. FAD2-a has expanded extensively in Asterales and Apiales, two main clades of campanulids, by ancient gene duplications. Here, we detected positive selection in both Asterales and Apiales lineages, which may have enabled the evolution of PA metabolism in campanulids. Together, these findings also imply that yet uncharacterized FAD2-a copies are involved in later steps of PA biosynthesis. This work establishes a robust phylogenetic framework in which to interpret functional data and to direct future research into the origin and evolution of PA metabolism.

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confidence: 99%

FAD2 Gene Radiation and Positive Selection Contributed to Polyacetylene Metabolism Evolution in Campanulids

et al. 2019

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“…In close similarity to the labeling pattern of the fatty acid residue of the lupeol derivative, a strict polyketide pattern was also observed for 13 CO 2 -labeled panaxynol and panaxydol from the plethora of secondary products formed by Panax ginseng [ 55 ]. Specifically, the number of 13 C atoms that had been imported jointly does not exceed two in any case.…”

Section: Polyacetylenes From Panax Ginsengmentioning

confidence: 79%

Decoding Biosynthetic Pathways in Plants by Pulse-Chase Strategies Using 13CO2 as a Universal Tracer

Bacher¹,

Chen²,

Eisenreich³

2016

Metabolites

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13CO2 pulse-chase experiments monitored by high-resolution NMR spectroscopy and mass spectrometry can provide 13C-isotopologue compositions in biosynthetic products. Experiments with a variety of plant species have documented that the isotopologue profiles generated with 13CO2 pulse-chase labeling are directly comparable to those that can be generated by the application of [U-13C6]glucose to aseptically growing plants. However, the application of the 13CO2 labeling technology is not subject to the experimental limitations that one has to take into account for experiments with [U-13C6]glucose and can be applied to plants growing under physiological conditions, even in the field. In practical terms, the results of biosynthetic studies with 13CO2 consist of the detection of pairs, triples and occasionally quadruples of 13C atoms that have been jointly contributed to the target metabolite, at an abundance that is well above the stochastic occurrence of such multiples. Notably, the connectivities of jointly transferred 13C multiples can have undergone modification by skeletal rearrangements that can be diagnosed from the isotopologue data. As shown by the examples presented in this review article, the approach turns out to be powerful in decoding the carbon topology of even complex biosynthetic pathways.

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“…The use of 13 CO 2 as a tracer is a powerful tool, since this strategy represents the possibility of studying metabolic pathways in plants by mimicking, as much as possible, their physiological growth conditions [ 40 , 41 , 42 ]. The labelling period (pulse) is followed by a chase period in which the plants grow under normal conditions and natural 13 CO 2 abundance for several hours/days.…”

Section: Introductionmentioning

confidence: 99%

Dynamics of Monoterpene Formation in Spike Lavender Plants

et al. 2017

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The metabolic cross-talk between the mevalonate (MVA) and the methylerythritol phosphate (MEP) pathways was analyzed in spike lavender (Lavandula latifolia Med) on the basis of 13CO2-labelling experiments using wildtype and transgenic plants overexpressing the 3-hydroxy-3-methylglutaryl CoA reductase (HMGR), the first and key enzyme of the MVA pathway. The plants were labelled in the presence of 13CO2 in a gas chamber for controlled pulse and chase periods of time. GC/MS and NMR analysis of 1,8-cineole and camphor, the major monoterpenes present in their essential oil, indicated that the C5-precursors, isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP) of both monoterpenes are predominantly biosynthesized via the MEP pathway. Surprisingly, overexpression of HMGR did not have significant impact upon the crosstalk between the MVA and MEP pathways indicating that the MEP route is the preferred pathway for the synthesis of C5 monoterpene precursors in spike lavender.

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Biosynthesis of Panaxynol and Panaxydol in Panax ginseng

Cited by 21 publications

References 56 publications

FAD2 Gene Radiation and Positive Selection Contributed to Polyacetylene Metabolism Evolution in Campanulids

FAD2 Gene Radiation and Positive Selection Contributed to Polyacetylene Metabolism Evolution in Campanulids

Decoding Biosynthetic Pathways in Plants by Pulse-Chase Strategies Using 13CO2 as a Universal Tracer

Dynamics of Monoterpene Formation in Spike Lavender Plants

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