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

Abstract

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.

Isorhapontigenin: A novel bioactive stilbene from wine grapes

“…However, the fragmentation pattern differed from previous descriptions (Pezet et al, 2003;Püssa et al, 2006). It might be tentatively identified as pallidol, which shows this mass fragmentation pattern (Mulinacci, Innocenti, Santamaria, la Marca, & Pasqua, 2010), and maximum wavelength at 280 nm, in agreement with literature (Vitrac, Monti, Vercauteren, Deffieux, & Merillon, 2002;Landrault et al, 2002). Fraction 4 (FF4) presented several unidentified compounds, whose mass spectral data could be related to oxidised dimeric stilbenes (Mulinacci et al, 2010).…”

Investigation of monomeric and oligomeric wine stilbenoids in red wines by ultra‐high‐performance liquid chromatography/electrospray ionization quadrupole time‐of‐flight mass spectrometry

“…[11] Although some of these compounds such as pallidol-3-O-glycoside (29) and ϵ-viniferin-glycoside (28) have been isolated in white wine, [24] we report ten dimers that have not yet been reported in wine but have been described in cell cultures of Vitis vinifera. [25] Many of these stilbenoid dimer derivatives have also been identified in other plant species as well as in the leaves and stems of Vitis vinifera. [26] The stilbenoid trimers and tetramers are also well represented in many different species of plants, including Vitis vinifera.…”

“…Although compounds that fit this description have been found in the literature, they have not been characterized. [25] Additional studies need to be performed about the oxidation products of resveratrol and its dimers including NMR studies.…”

“…[28] Other studies have identified multiple isomers in Vitis vinifera. [25] However, it was only very recently that a trimeric stilbene, ampelopsin C, was identified in wine by LC/NMR. [33]…”

Optimize, Modulate, and Scale-up Resveratrol and Resveratrol Dimers Bioproduction in Vitis labrusca L. Cell Suspension from Flasks to 20 L Bioreactor

“…Vitis cells cultivated in vitro not only produce resveratrol and piceid, but a large diversity of compounds, from monomers like piceatannol, astringin, resveratroloside, resveratrol di-and triglucosides, to dimers such as pallidol, ε-viniferin, δ-viniferin, and leachianols F and G [4,20,[28][29][30][31][32][33], and a new dimer named labruscol was recently identified in V. labrusca cell suspension [5]. Biological activities of resveratrol oligomers are attracting the attention of scientists, but their level of production in grapevine cell culture is low: In the order of milligrams per liter (mg/L) or milligrams per kilogram (mg/kg) of fresh weight [31,34,35].…”