Two-Dimensional NMR Identification of an Acetophenone Glycoside Isolated from Solanaceous Cell Suspensions

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

doi:10.1080/00387019608001592

Cited by 2 publications

(1 citation statement)

References 7 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: 96%

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: 96%

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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Two new acetoisovanillone glycosides from the water-soluble fraction of Paeonia ostii

Sun

Chen

et al. 2019

Natural Product Research

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The cortex root of Paeonia ostii, is used as a traditional Chinese medicine for treating female diseases.Phytochemical investigation of the water-soluble fraction of the plant led to the isolation of two new acetoisovanillone glycosides: acetoisovanillone-3-O-β-D-glucopyranoside (1) and 2-hydroxy-acetoisovanillone-3-O-β-D-glucopyranoside (2). Their structures were elucidated by extensive spectroscopic methods.

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Two-Dimensional NMR Identification of an Acetophenone Glycoside Isolated from Solanaceous Cell Suspensions

Cited by 2 publications

References 7 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

Two new acetoisovanillone glycosides from the water-soluble fraction of Paeonia ostii

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