Analysis of some stilbenes in Italian wines by liquid chromatography/tandem mass spectrometry

Abstract

Stilbenes from grapes and wines play a central role in the human diet because of their antioxidant, antimutagenic and anticarcinogenic properties. We describe a method for the direct determination of some stilbenes (cis- and trans-resveratrol, cis- and trans-resveratrol glucoside, cis- and trans-piceatannol, and cis- and trans-piceatannol glucoside) in wine by high-performance liquid chromatography/mass spectrometry using a triple quadrupole (QqQ) mass spectrometer, in multiple reaction monitoring (MRM) mode, acquiring two diagnostic product ions from the chosen precursor. All the target analytes were separated on a C-18 column using gradient elution, in a single run. Electrospray ionization (ESI) in negative ion mode gives higher sensitivity for all the target compounds than atmospheric pressure chemical ionization (APCI). For the identification of piceatannol glucoside (astringin), because of the lack of a suitable standard, an HPLC/TOFMS method was used. The method permits direct injection of samples and it is time-saving, removing the need for sample pre-treatment. The detection limits were 48.0 ng mL(-1) for cis- and trans-resveratrol and for cis- and trans-resveratrol glucoside, and 50.0 ng mL(-1) for cis- and trans-piceatannol. The procedure proved to be simple and suitable for routine and confirmatory purposes. A total of 19 red and 3 white Italian wines were analyzed and differences in the stilbene composition were found among these samples.

Isorhapontigenin: A novel bioactive stilbene from wine grapes

“…1; Table 1). The mass spectra agree with those previously described in literature (Buiarelli, Coccioli, Jasionowska, Merolle, & Terracciano, 2007;Pezet et al, 2003;Püssa, Floren, Kuldkepp, & Raal, 2006). As it can be observed in the DAD chromatogram (Fig.…”

Biosynthesis of the Major Tetrahydroxystilbenes in Spruce, Astringin and Isorhapontin, Proceeds via Resveratrol and Is Enhanced by Fungal Infection

“…S4). Similar fragmentation spectra have been previously described for resveratrol and piceatannol (Buiarelli et al, 2007;Lo et al, 2007), and the two 42-D molecules lost during fragmentation of these compounds have been identified as ketene molecules involving positions 3, 4, 5, and 6 on the stilbene skeleton (Supplemental Fig. S5).…”

The chemodiversity of wines can reveal a metabologeography expression of cooperage oak wood

“…Many of these metabolites (among which for example are isomers of quercetin, catechin and myricetin) are known to exist in red wines and are therefore a reliable validation of such database treatment of our raw sets of masses. Likewise, the peak at m/z 243.0662 corresponding to the [M-H] Ϫ ion with absolute mass formula [C 14 H 11 O 4 ] Ϫ , and which is found in the phenylpropanoid pathway as the antioxidant tetrahydroxystilbene piceatannol (see Table S1), a parent molecule of resveratrol, is known to be efficiently ionized in negative mode ESI (22 Ϫ and the possible attribution to afzelechin (flavonoid biosynthesis pathway), known as a secondary metabolite in grape leaves (23), would witness the presence of yet unreported antioxidant compounds in red wines. Applying a similar MassTRIX treatment to masses that discriminate the white wine leads to the identification of 21 distinct formulas that can be associated with 31 possible metabolites from the different annotated Vitis vinifera organism pathways (see Fig.…”