Galloylated catechins and stilbene diglucosides in Vitis vinifera cell suspension cultures

Décendit, Alain; Waffo-Téguo, Pierre; Richard, Tristan; Krisa, Stéphanie; Vercauteren, Joseph; Monti, J. P.; Deffieux, Gérard; Mérillon, Jean Michel

doi:10.1016/s0031-9422(02)00149-8

Cited by 34 publications

(20 citation statements)

References 23 publications

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“…Up to now, it has been recognized that only small amounts of stilbenoids are usually found in Vitis plants and consequently it is of considerable interest to evaluate the possibility of obtaining trans ‐resveratrol and other stilbenoids from alternative matrices such as in vitro systems. Several authors have undertaken studies on V. vinifera cell cultures to investigate the factors that are able to induce and/or modify the biosynthesis of stilbenoidic compounds 4, 5, 24, 25. Within this field, one of the main targets is the optimization of the in vitro production of stilbenes.…”

supporting

confidence: 92%

“…These metabolites have been found in different parts of the plant (shoots, infected leaves, rachids), but their concentration is usually low and widely variable 2, 3. However, cell suspension cultures of Vitis , particularly after elicitation, have also shown the ability to biosynthesize stilbenoids 4. From these cells, besides trans ‐resveratrol, monomeric stilbene glucosides, cis ‐ and trans ‐astringin, cis ‐ and trans ‐resveratroloside,5 dimeric stilbene glucosides, resveratrol trans ‐dehydrodimer 11‐ O ‐β‐D‐glucopyranoside and resveratrol trans ‐dehydrodimer 11‐ O ‐β‐D‐glucopyranoside,6 were isolated.…”

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confidence: 99%

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High‐performance liquid chromatography/electrospray ionization tandem mass spectrometric investigation of stilbenoids in cell cultures of Vitis vinifera L., cv. Malvasia

Mulinacci

Innocenti

Santamaría

et al. 2010

Rapid Comm Mass Spectrometry

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Cell suspension cultures of Vitis vinifera L., particularly after elicitation, have shown the ability to biosynthesize several stilbenoids. In this work the application of specific tandem mass spectrometry (MS/MS) experiments and the integration with data from UV-vis spectra, available only for the main compounds of the extract, allowed the detection of over 20 different stilbenoids. Up to eight monoglicosides, both monomers and dimers, a high number of dimer forms (up to 17), belonging to the group of viniferins and to their oxidized derivatives, were identified in the extract of Malvasia cell cultures. Moreover, the selectivity and sensitivity of the method allowed detection also of a few cis derivatives (up to 3) present in very low concentrations and presumably produced by the light exposure during treatment of the sample. To the best of the authors' knowledge, there are no literature data on MS/MS experiments targeted to simultaneously study monomeric and dimeric stilbenoids, both as free and glycosilated forms, in a complex mixture from V. vinifera cell suspension cultures.

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confidence: 92%

mentioning

confidence: 99%

High‐performance liquid chromatography/electrospray ionization tandem mass spectrometric investigation of stilbenoids in cell cultures of Vitis vinifera L., cv. Malvasia

Mulinacci

Innocenti

Santamaría

et al. 2010

Rapid Comm Mass Spectrometry

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“…In addition to the piceids, the QTrap® hybrid instrument allowed the detection of resveratrol diglucoside as well as trans ‐ and cis ‐resveratrol acetylhexosides in transgenic Arabidopsis plants in this study. Recently, both trans ‐ and cis ‐resveratrol diglucosides were isolated from grape cell suspension cultures 23. To our knowledge, however, trans ‐ and cis ‐resveratrol acetylglucosides have not been reported elsewhere.…”

Section: Resultsmentioning

confidence: 90%

Detection, characterization, and quantification of resveratrol glycosides in transgenic arabidopsis over‐expressing a sorghum stilbene synthase gene by liquid chromatography/tandem mass spectrometry

Blanc

et al. 2007

Rapid Comm Mass Spectrometry

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Transgenic Arabidopsis plants were analyzed by liquid chromatography/tandem mass spectrometry (LC/MS/MS) to investigate the glycosylation patterns of resveratrol derived from expression of a sorghum stilbene synthase gene. In negative ionization mode, the different resveratrol derivatives fragmented to yield the diagnostic deprotonated resveratrol ion at m/z 227.2. The use of precursor ion scanning led to the identification of precursor ions for different resveratrol glycosides through rapid differentiation from other phytochemical constituents. Structural information was generated simultaneously from the low-collision-energy product ion spectra using hybrid linear ion-trap mass spectrometry. Three additional resveratrol-related metabolites - a resveratrol diglucoside (M1) and trans- and cis-resveratrol acetylhexosides (M2 and M3) - were detected in the crude plant extracts. The identities of M1, M2, and M3 were confirmed by accurate mass analysis on a quadrupole time-of-flight mass spectrometer as well as beta-glucosidase digestion or UV-induced isomerization. Quantitative analyses by LC/MS in multiple reaction monitoring mode revealed that resveratrol diglucoside and cis-resveratrol acetyhexoside accumulated up to 2.79 and 10.38 microg/g, respectively, while trans-resveratrol acetylhexoside was barely detectable. This study demonstrated the power of the hybrid linear ion-trap technology for simultaneous profiling and structural characterization of stilbene-related metabolites, which would be useful to understand how resveratrol is modified in sorghum and other plants.

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“…for C 26 H 32 O 13 Na: 575) to be deduced. The 1 H-NMR spec-trum of 1 showed two sets of signals characteristic of a resveratrol glucoside structure [4], [5], [6]. The former, between d = 7.10 and 6.30, composed of three systems of two olefinic and seven aromatic protons, was typical for resveratrol.…”

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New Stilbenoid Glucosides Isolated fromVitis viniferaCell Suspension Cultures (cv. Cabernet Sauvignon)

et al. 2005

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Three new monomeric stilbenoid glucosides, (Z)- and (E)-resveratrol 3,5- O-beta-diglucosides (1 and 2, respectively) and (Z)-resveratrol 3,5,4'- O-beta-triglucoside (3), were isolated from an extract of Vitis vinifera cell cultures (Cabernet Sauvignon) together with the known (E)- and (Z)-piceids and (E)- and (Z)-resveratrol 3,4'- O-beta-diglucosides that have already been identified in a Gamay cell culture extract. The structure determinations were based on spectroscopic data analysis.

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Galloylated catechins and stilbene diglucosides in Vitis vinifera cell suspension cultures

Cited by 34 publications

References 23 publications

High‐performance liquid chromatography/electrospray ionization tandem mass spectrometric investigation of stilbenoids in cell cultures of Vitis vinifera L., cv. Malvasia

High‐performance liquid chromatography/electrospray ionization tandem mass spectrometric investigation of stilbenoids in cell cultures of Vitis vinifera L., cv. Malvasia

Detection, characterization, and quantification of resveratrol glycosides in transgenic arabidopsis over‐expressing a sorghum stilbene synthase gene by liquid chromatography/tandem mass spectrometry

New Stilbenoid Glucosides Isolated fromVitis viniferaCell Suspension Cultures (cv. Cabernet Sauvignon)

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