Evaluation of the relation between the endogenous scopoletin and scopolin level of some solanaceous and papaver cell suspensions and their ability to bioconvert scopoletin to scopolin

Fliniaux, Marc‐André; Gillet-Manceau, F.; Marty, Danielle; Macek, Tomáš; Monti, Jean‐Pierre; Jacquin-Dubreuil, Annie

doi:10.1016/s0168-9452(96)04596-7

Cited by 22 publications

(9 citation statements)

References 18 publications

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“…2A) can be assigned to the methoxy groups of compounds such as phenolics and conjugated polyamines. Soluble phenolics are known to accumulate in cell-suspension cultures (Marty et al 1996;Fliniaux et al 1997) and conjugated polyamines are present at appreciable concentrations in this Fig. 3A, B Changes in peak intensity for the 13 C NMR signals numbered 1-6 ( Fig.…”

Section: Metabolism Of [ 13 C-methyl]nicotinementioning

confidence: 94%

Evidence for the involvement of tetrahydrofolate in the demethylation of nicotine by Nicotiana plumbaginifolia cell-suspension cultures

Mesnard

Roscher

Garlick

et al. 2002

Planta

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The conversion of nicotine to nornicotine by Nicotiana plumbaginifolia Viv. cells was investigated by analysing the redistribution of label during feeding experiments with (R,S)-[2H- methyl]nicotine, (R,S)-[13C- methyl]nicotine and (R,S)-[14C- methyl]nicotine, and the results show that the N-methyl group of nicotine can be recycled into primary metabolism. Nuclear magnetic resonance (NMR) analysis of ethanolic extracts of cells grown in the presence of (R,S)-[13C- methyl]nicotine, using 1H-13C correlation spectroscopy (HMQC, HMBC), revealed the presence of [3-13C]serine and [13C- methyl]methionine. Label was also identified in a cysteinyl derivative and in several methoxylated compounds, but no evidence was obtained with either NMR or ion-trap mass spectrometry for the presence of any intermediate between nicotine and nornicotine. However, experiments with (R,S)-[14C- methyl]nicotine indicated that 70-75% of the metabolised label was released as carbon dioxide. These results are consistent with a pathway in which the oxidative hydrolysis of the nicotine methyl produces an unstable intermediate, N'-hydroxymethylnornicotine, that breaks down spontaneously to nornicotine and formaldehyde, with the formaldehyde being metabolised either directly to formate and carbon dioxide, or through the tetrahydrofolate-mediated pathways of one-carbon metabolism. However since the key intermediate, N-hydroxymethylnornicotine, could not be detected, the possibility of a direct methyl group transfer to tetrahydrofolate cannot be excluded.

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Section: Metabolism Of [ 13 C-methyl]nicotinementioning

confidence: 94%

Evidence for the involvement of tetrahydrofolate in the demethylation of nicotine by Nicotiana plumbaginifolia cell-suspension cultures

Mesnard

Roscher

Garlick

et al. 2002

Planta

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“…fraction (7.6 g) was separated using the above HPLC conditions. A 7.1 (and a trace of a 27.4) min peak was detected, collected, concentrated and dissolved in MeOH (0.2 g/ml) and identified by high field NMR spectroscopy and HR MS (Fliniaux et al, 1997), in order to identify the unlabelled coumarin, scopolin (7 mg…”

Section: Extraction Purification and Characterisation Of Scopolin Anmentioning

confidence: 99%

Biosynthesis of scopoletin and scopolin in cassava roots during post-harvest physiological deterioration: The E-Z-isomerisation stage

et al. 2008

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Two to three days after harvesting, cassava (Manihot esculenta Crantz) roots suffer from post-harvest physiological deterioration (PPD) when secondary metabolites are accumulated. Amongst these are hydroxycoumarins (e.g. scopoletin and its glucoside scopolin) which play roles in plant defence and have pharmacological activities. Some steps in the biosynthesis of these molecules are still unknown in cassava and in other plants. We exploit the accumulation of these coumarins during PPD to investigate the E-Z-isomerisation step in their biosynthesis. Feeding cubed cassava roots with E-cinnamic-3,2',3',4',5',6'-d(5) acid gave scopoletin-d(2). However, feeding with E-cinnamic-3,2',3',4',5',6'-d(6) and E-cinnamic-2,3,2',3',4',5',6'-d(7) acids, both gave scopoletin-d(3), the latter not affording the expected scopoletin-d(4). We therefore synthesised and fed with E-cinnamic-2-d(1) when unlabelled scopoletin was biosynthesised. Solely the hydrogen (or deuterium) at C2 of cinnamic acid is exchanged in the biosynthesis of hydroxycoumarins. If the mechanism of E-Z-cinnamic acid isomerisation were photochemical, we would not expect to see the loss of deuterium which we observed. Therefore, a possible mechanism is an enzyme catalysed 1,4-Michael addition, followed by sigma-bond rotation and hydrogen (or deuterium) elimination to yield the Z-isomer. Feeding the roots under light and dark conditions with E-cinnamic-2,3,2',3',4',5',6'-d(7) acid gave scopoletin-d(3) with no significant difference in the yields. We conclude that the E-Z-isomerisation stage in the biosynthesis of scopoletin and scopolin, in cassava roots during PPD, is not photochemical, but could be catalysed by an isomerase which is independent of light.

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“…Of these, Ms12 and Ms15 are identical to the known compounds, dehydrosoyasaponin I [32] and soyasaponin βg [33], which have previously been structurally determined by spectroscopic analysis. Two sugar substitutes in Ms9−11 , deoxyribosyl and erythrosyl as determined by neutral losses of 116 and 102 Da [34], rarely appeared in the secondary metabolites of other tissues.…”

Section: Resultsmentioning

confidence: 99%

HPLC coupled with quadrupole time of flight tandem mass spectrometry for analysis of glycosylated components from the fresh flowers of two congeneric species: Robinia hispida L. and Robinia pseudoacacia L

Chen

et al. 2021

J of Separation Science

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Developing methods for the systematic and rapid identification of the chemical compositions of fresh plant tissues has long attracted the attention of phytochemists and pharmacologists. In the present study, based on highly efficient sample pretreatment and high‐throughput analysis of high‐performance liquid chromatography coupled with quadrupole time of flight tandem mass spectrometry data using molecular networks, a method was developed for systematically analyzing the chemical constituents of the fresh flowers of Robinia hispida L. and Robina pseudoacacia L., two congeneric ornamental species that lack prior consideration. A total of 44 glycosylated structures were characterized. And on the basis of establishing of the fragmentation pathways of 11 known flavonoid glycosides, together with the molecular networking analysis, 18 other ions of flavonoid glycosides in five classes were clustered. Moreover, 15 soyasaponins/triterpenoid glycosides were tentatively identified by comparison of their tandem mass spectrometry characteristic ions with those reported in the literature or the online Global Natural Product Social Molecular Networking database. The water extracts were separated by flash chromatography, which resulted in the discovery of one new compound, named rohispidascopolin, along with five known entities. The pharmacological targets were predicted by SwissTargetPrediction.

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Evaluation of the relation between the endogenous scopoletin and scopolin level of some solanaceous and papaver cell suspensions and their ability to bioconvert scopoletin to scopolin

Cited by 22 publications

References 18 publications

Evidence for the involvement of tetrahydrofolate in the demethylation of nicotine by Nicotiana plumbaginifolia cell-suspension cultures

Evidence for the involvement of tetrahydrofolate in the demethylation of nicotine by Nicotiana plumbaginifolia cell-suspension cultures

Biosynthesis of scopoletin and scopolin in cassava roots during post-harvest physiological deterioration: The E-Z-isomerisation stage

HPLC coupled with quadrupole time of flight tandem mass spectrometry for analysis of glycosylated components from the fresh flowers of two congeneric species: Robinia hispida L. and Robinia pseudoacacia L

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