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Food Chemistry 278 (2019) 497–501

Contents lists available at ScienceDirect

Food Chemistry
journal homepage: www.elsevier.com/locate/foodchem

NMR-based systematic analysis of bioactive phytochemicals in red wine. T


First determination of xanthurenic and oleanic acids

Martino Forino , Angelita Gambuti, Luigi Moio
Department of Agricultural Sciences, University of Napoli “Federico II” – Oenology Sciences Section, Viale Italia, 83100 Avellino, Italy

A R T I C LE I N FO A B S T R A C T

Keywords: Experimental evidence suggests that moderate consumption of wine has health promoting properties that have
Vitis vinifera L. cv Aglianico been mainly attributed to the wine polyphenol content. However, a systematic analysis of the major healthy
Wine bioactive molecules molecules contained in wines has not been conducted yet. Our study explored the potential arsenal of beneficial
Xanthurenic acid molecules contained in wine from both a qualitative and quantitative perspective. The experimental approach
Oleanic acid
was based on chromatography and untargeted NMR spectroscopy. In addition to already known bioactive
NMR
molecules, for the first time, xanthurenic acid and oleanic acid were identified in wine in relatively high con-
centrations. On account of their many biological activities, these two molecules widen the range of potential
beneficial effects of wine and pave the way toward the evaluation of their still unexplored sensory properties.

1. Introduction platelet aggregation involved in atherosclerosis processes (Gresele


et al., 2011). The bioactivity spectrum of resveratrol is quite wide
Over the past years, the scientific community has long argued as to ranging from anti-inflammatory effects to cardio-, neuro- and chemo-
whether wine, and especially red wine, is to be regarded as beneficial or preventive properties (Brown et al., 2009). Nonetheless, the oral bioa-
detrimental to human health. The debate is still open, but there is a vailability of resveratrol, like that of polyphenols in general, is quite
growing body of experimental and clinical evidence that a moderate low, albeit it seems to be high enough to exert an efficient antioxidant
consumption of wine can have healthy effects. Wine chemical compo- activity (Stockley, Teissedre, Boban, Di Lorenzo, & Restani, 2012). It is
sition includes a vast selection of compounds that, either as such or reasonable hypothesizing that the entire profile of potential bioactive
synergistically with ethanol, are held responsible for red wine anti- compounds in wine extends far beyond polyphenols; but, this hypoth-
oxidant, anti-inflammatory cardio- and cyto-protective properties. esis can be verified only by a systematic phytochemical analysis that
Accordingly, many clinicians, on the basis of in vitro, in vivo and epi- has not been conducted yet. Therefore, with the purpose of contributing
demiological studies, contend that moderate wine assumption reduces to fill the knowledge gap on such an issue relevant to both consumers
the cardiovascular risk (Haseeb, Alexander, & Baranchuk, 2017) and is and wine producers, we analyzed samples of red wine obtained from
beneficial in important pathologies such diabetes, osteoporosis and Vitis vinifera L. cv Aglianico grapes harvested in the autumn of 2017.
perhaps neurological diseases as well (Artero, Artero, Tarin, & Cano, This is the most important black grape variety of Southern Italy used to
2015). These biological properties of red wine have been so far ascribed produce renowned red wines awarded the DOCG designation (De-
to its high content of polyphenols, a large family of compounds com- nominazione di Origine Controllata e Garantita), the national highest wine
monly divided into two groups: flavonoids and non-flavonoids. Flavo- classification. Our investigation was carried following an experimental
noids constituting up to 85% of the red wine polyphenols include fla- procedure based on chromatography and untargeted NMR spectro-
vones, anthocyanins and falvonols, among which quercetin is the most scopy. Chromatographic separations were instrumental for fractioning
abundant. The non-flavonoid family includes hydroxycinnamic acids, the several classes of metabolites in a complex organic matrix like wine
hydroxybenzoic acids and stilbenes such as resveratrol. Scientific stu- and, if necessary, purifying them for their structural elucidation. To this
dies aimed at ascertaining the beneficial effects of red wine have been aim, the untargeted NMR analysis, unlike any other targeted approach
focused essentially on quercetin and resveratrol. Quercetin is an effec- focused on the detection of specific compounds of interest, was selected
tive free radical scavenger and prevents systemic inflammation (Chang, on account of its suitability to allow a comprehensive chemical iden-
Tsai, Sheu, Hsieh, & Chiang, 2013). Additionally, it seems to inhibit tification of analytes from both a qualitative and quantitative point of


Corresponding author.
E-mail address: forino@unina.it (M. Forino).

https://doi.org/10.1016/j.foodchem.2018.11.103
Received 25 July 2018; Accepted 20 November 2018
Available online 22 November 2018
0308-8146/ © 2018 Elsevier Ltd. All rights reserved.
M. Forino et al. Food Chemistry 278 (2019) 497–501

view. Additionally, with the purpose of identifying potential precursors glucoside and quercetin-3-O-glucuronide, along with trace amounts of
of the healthy molecules detected in wine, samples of grapes used to kaempferol-3-O-glucoside) were isolated.
produce the analyzed wine were also investigated. The skin EtOAc extract was loaded on a 40-gr CombiFlash Silica
column and eluted with a gradient elution with changing ratio of
2. Materials and methods EtOAc:MeOH, from 100:0 to 50:50 in 60 min (3 mL/min flow). From
this separation the triterpenoid oleanic acid, catechin and epicatechin
2.1. General experimental procedures were isolated.
Both the seed butanol and EtOAc extracts were separated as re-
A linear ion trap LTQ Orbitrap XL hybrid Fourier Transform MS ported above for the skins. The butanol extract was found to contain the
(FTMS) instrument equipped with an ESI ION MAX source (Thermo- same carbohydrates and amino acids as those identified in the skins.
Fisher, Waltham, MA, USA) and coupled to an Agilent 1100 LC binary From the seed EtOAc extract, catechin and epicatechin were isolated.
system was used for Mass Spectrometry analyses. All the solvents were
of laboratory grade. 2.2.2. Wine
NMR experiments were run on a Varian Unity Inova 700 spectro- Red wine samples were kindly provided by Azienda Quintodecimo
meter equipped with a 13C Enhanced HCN Cold Probe and by using a (Mirabella Eclano, Avellino, Italy). The wine was obtained from grapes
Shigemi 5 mm NMR tubes. CD3OD (δH 3.31; δC 49.0) was selected as of which a sample had been analyzed as reported in Section 2.2.1.
deuterated solvent. Standard Varian pulse sequences were employed for 200 mL of wine were diluted in an equal volume of distilled water and
the respective classes of spectra. All NMR data reported in the text were loaded onto a glass column (100 cm × 2 cm) packed with 70 cm of
derived from 1D 1H and 13C NMR spectra and from 2D experiments Amberlite XAD-2. The resin had been washed with methanol, diethyl
including COSY, TOCSY, ROESY, HMBC, and HSQC. For quantitation ether and finally water. After loading the liquid sample, the column was
purposes, 5 μL of pyridine as an internal standard was added to the eluted with 300 mL of water (Fraction A′), followed, in the order, by
NMR tubes containing the analytes to be quantified and 1H NMR 300 mL of EtOAc (Fraction B′), and 300 mL of MeOH (Fraction C′).
spectra were acquired setting the d1 value at 7.0 s in order to allow a Fraction A′ contained amino acids (mainly, alanine, isoleucine, leucine,
complete relaxation of the pyridine standard to equilibrium. The T1 proline and valine), glycerol, carbohydrates (α-glucose, β-glucose,
(0.70 s) of pyridine was evaluated through the inversion-recovery T1 fructose) and polyols (sorbitol and mannitol), and organic acids (lactic
experiment. Quantitation of each compound was conducted by se- acid, pyruvic acid, succinic acid, acetic acid, citric acid and tartaric
lecting representative NMR signals and their areas determined by in- acid). Fraction B′ was further purified through a 40-gr CombiFlash Silica
tegration. column eluted with a gradient elution with changing ratio of EtOAc:-
MeOH, from 100:0 to 50:50 in 30 min (3 mL/min flow). In fractions
2.2. Biological material, extraction and separation collected from this column, gallic acid, syringic acid, catechin, epica-
techin, 2-phenylethanol, tyrosol, tryptophol, xanthurenic acid, oleanic
2.2.1. Grapes acid and caffeoyl tartaric acid were identified. Fraction C′ contained a
Vitis vinifera L. cv Aglianico grape was harvested from the vineyard complex mixture of polyphenol pigments, including malvidin-3-O-glu-
of Azienda Quintodecimo (Mirabella Eclano, Avellino, Italy) in late coside and condensed tannins.
September 2017. Berries were collected from different patches of the
vineyard to obtain a sample homogenous and representative of the 2.3. Identified bioactive compounds
cultivar. A voucher specimen (Ag-1-2017) is deposited at the
Department of Agricultural Sciences of the University of Napoli 2.3.1. Catechin
“Federico II” – Oenology Sciences Section. HRESIMS m/z 291.0866 [M+H]+ corresponding to C15H15O6. 1H
A large-scale extraction (2 kg of fresh product) was carried out. Skin NMR data in CD3OD at 25 °C (700 MHz): H2 4.57 (doublet J 7.4 Hz); H3
and seeds from each berry were manually separated, ground in a la- 3.97 (multiplet); H4a 2.50 (doublet of doublets J 16.5, 9.0 Hz); H4b
boratory blender and extracted twice at room temperature with 2,0 L of 2.86 (doublet of doublets J 16.5, 1.7 Hz); H6 5.86 (doublet J 2.2 Hz);
H2O:EtOH 2:8 (v/v) overnight. The dry weight of the extracted skins H8 5.92 (doublet J 2.2 Hz); H2′ 6.84 (doublet J 1.6 Hz); H5′ 6.76
was 280 gr, and the dry weight of the extracted seeds was 173 gr. The (doublet J 7.1 Hz); H6′ 6.71 (doublet of doublets J 7.1, 1.6 Hz).
hydroethanolic extracts of both skins and seeds were concentrated and
partitioned first against EtOAc and then n-butanol. All of the obtained 2.3.2. Epicatechin
extracts were fully evaporated. The final weight of the skin EtOAc ex- HRESIMS m/z 291.0862 [M+H] + corresponding to C15H15O6. 1H
tract was 5 gr; the skin butanol extract weighted 12 gr; the seed EtOAc NMR data in CD3OD at 25 °C (700 MHz): H3 4.18 (multiplet); H4a 2.74
extract 8 gr, and the seed butanol extract 7 gr. Preliminary NMR in- (doublet of doublets J 16.6, 1.5 Hz); H4b 2.84 (doublet of doublets J
vestigations of the aqueous layers and of the pulp led to the identifi- 16.6, 2.4 Hz); H6 5.93 (doublet J 2.3 Hz); H8 5.95 (doublet J 2.3 Hz);
cation of carbohydrates (α-glucose, β-glucose and fructose) and organic H2′ 6.97 (doublet J 1.6 Hz); H5′ 6.76 (doublet J 7.1 Hz); H6′ 6.80
acids (mainly malic and tartaric acids) and were not further analyzed. (doublet of doublets J 7.1, 1.6 Hz).
The skin butanol extract was separated through a 360-gr
CombiFlash C-18 column connected to a Teledyne Isco CombiFlash Rf 2.3.3. Gallic acid
chromatography system and eluted with H2O:MeOH whose ratio HRESIMS m/z 169.0147 [M−H]− corresponding to C7H5O5. 1H
changed from 1:1 to MeOH 100% in 60 min (5,0 mL/min flow). Two NMR data in CD3OD at 25 °C (700 MHz): H2/H6 7.05 (singlet).
fractions (A and B) were collected on the basis of their increasing li-
pophilicity. Fraction A contained carbohydrates (α-glucose, β-glucose 2.3.4. Olenic acid
and fructose) and organic acids (tartaric acid, malic acid and citric HRESIMS m/z 457.3670 [M+H]+ corresponding to C30H49O3. 1H
acid). Fraction B contained a complex mixture of metabolites and was NMR data in CD3OD at 25 °C (700 MHz): H1a 2.26 (triplet J 7.4 Hz);
further separated on a 40-gr CombiFlash Silica column eluted with a H1b 2.32 (triplet J 7.4 Hz); H2a 1.56 (overlapped); H2b 1.62 (over-
gradient elution with changing ratio of EtOAc:MeOH, from 100:0 to lapped); H3 3.14 (triplet J 7.3 Hz); H5 0.74 (broad singlet); H6a 1.41
50:50 in 30 min (3 mL/min flow). From this chromatographic separa- (overlapped); H6b 1.55 (overlapped); H27 1.30 (overlapped); H9 1.58
tion anthocyanins (mainly malvidin-3-O-glucoside), amino acids (ala- (overlapped); H211 1.89 (doublet of doublets J 8.9, 3.9 Hz); H12 5.23
nine, arginine, glutamic acid, leucine, isoleucine, phenylalanine, pro- (broad singlet); H15a 1.06 (overlapped); H15b 1.76 (overlapped); H16a
line, threonine, tryptophan and tyrosine) and flavonols (quercetin-3-O- 1.58 (overlapped); H16b 1.99 (overlapped); H18 2.84 (doublet of

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M. Forino et al. Food Chemistry 278 (2019) 497–501

doublets J 12.8, 3.8 Hz); H19a 1.13 (overlapped); H19b 1.68 (over- Table 1
lapped); H21a 1.19 (overlapped); H21b 1.38 (overlapped); H22a 1.52 Major bioactive metabolites identified in Aglianico
(overlapped); H22b 1.73 (overlapped); H323 0.97 (singlet); H324 0.77 wine.
(singlet); H325 0.93 (singlet); H326 0.81 (singlet); H327 1.15 (singlet); Compounds mg/L
H329 0.90 (singlet); H330 0.94 (singlet). 13C NMR data in CD3OD at
25 °C (700 MHz): C1 33.0; C2 26.4; C3 78.3; C4 38.3; C5 55.3; C6 18.0; Epicatechin 210
Catechin 180
C7 32.7; C8 38.9; C9 47.7; C10 36.8; C11 23.1; C12 122.2; C13 143.8;
2-phenylethanol 100
C14 41.3; C15 27.3; C16 22.8; C17 46.1; C18 41.4; C19 45.6; C20 30.1; Tyrosol 100
C21 33.5; C22 32.4; C23 27.2; C24 14.9; C25 14.5; C26 16.3; C27 25.0; Oleanic acid 30
C28 180.7; C29 32.1; C30 22.6. Caffeoyl tartaric acid 30
Gallic acid 20
Tryptophol 20
2.3.5. 2-phenylethanol Syringic acid 10
HRESIMS m/z 123.0810 [M+H]+ corresponding to C8H11O. 1H Xanthurenic acid 10
NMR data in CD3OD at 25 °C (700 MHz): H21 3.74 (triplet J 7.1 Hz);
H22 2.81 (triplet J 7.1 Hz); aromatic ring constituted by H2′/6′, H3′/5′,
H4′: overlapped resonances ranging from 7.15 to 7.33. hypotheses. To quantitate the identified analytes, 100 mL of wine were
first concentrated to reduce the ethanol content and then partitioned
2.3.6. Syringic acid against EtOAc. The organic layer was evaporated and the extract totally
HRESIMS m/z 197.0461 [M−H]− corresponding to C9H9O5. 1H solubilized in CD3OD and added with 5 μL of pyridine as a standard. 1H
NMR data in CD3OD at 25 °C (700 MHz): H22/6 7.33 (singlet); H6-OCH3 NMR spectrum of the obtained solution was run by setting the d1 value
3.88 (singlet). at 7.0 sec to allow a complete relaxation of the observed nuclei to
equilibrium. Quantitation of the wine compounds was conducted by
2.3.7. Tryptophol selecting representative NMR signals on the basis of resolution. The
HRESIMS m/z 162.0912 [M+H]+ corresponding to C10H12NO. 1H area of the chosen resonances was determined by integration, divided
NMR data in CD3OD at 25 °C (700 MHz): H2 7.06 (broad singlet); H4 by the number of the protons generating them, and finally converted
7.53 (doublet J 8.0 Hz); H5 6.98 (triplet of doublets J 7.6, 0.9 Hz); H6 into the relative number of moles by comparing the obtained area with
7.06 (triplet of doublets J 7.7, 0.8 Hz); H7 7.31 (doublet J 8.1 Hz); H28 that of the pyridine protons, for which the number of moles was known.
2.97 (triplet J 7.3 Hz); H29 3.80 (triplet J 7.3 Hz).
3.2. Bioactive compounds identified in wine
2.3.8. Tyrosol
HRESIMS m/z 139.0757 [M+H]+ corresponding to C8H11O2. 1H Our NMR-based quali-quantitative analysis defined a quite inter-
NMR data in CD3OD at 25 °C (700 MHz): H22/6 7.02 (doublet J 8.4 Hz); esting picture of bioactive molecules. Alongside typical wine specia-
H23/5 6.69 (doublet J 8.4 Hz); H27 2.71 (triplet J 7.2 Hz); H28 3.67 lized metabolites, namely catechin (180 mg/L), epicatechin (210 mg/
(triplet J 7.2 Hz). L), gallic acid (20 mg/L), syringic acid (10 mg/L) and caffeoyl tartaric
acid (30 mg/L) and anthocyanins/condensed tannins (1600 mg/L),
2.3.9. Xanthurenic acid some metabolites, namely tryptophol, tyrosol and 2-phenylethanol,
HRESIMS m/z 206.0452 [M+H]+ corresponding to C10H8NO4. 1H were found to be occurring in relatively high concentrations (Fig. 1).
NMR data in CD3OD at 25 °C (700 MHz): H3 7.05 (singlet); H5 7.44 The presence of these three compounds in wine is not unusual, as they
(doublet of doublets J 7.7, 0.6 Hz); H6 7.37 (triplet J 7.7 Hz); H7 7.30 are likely produced during fermentation from the precursors tyrosine,
(doublet J 8.0 Hz). tryptophan and 2-phenylalanine, respectively, via yeast metabolism
through the Ehrlich pathway. However, if the estimated concentration
2.4. Statistical analysis of 2-phenylethanol (100 mg/L) is just a little bit over the typical ranges
in red wines (Francis & Newton, 2005), concentrations of tyrosol
Statistical analyses were conducted by using GraphPad Prism 6.0. (100 mg/L) are two times higher than those detected by HPLC-MS by
All quantitative measurements were carried out in triplicates. Gris et al. (2011), even if a great variability of concentrations of such a
compound (1.00–60.00 mg/L wine) is reported in literature. Even
3. Results and discussion greater than that reported in literature is the calculated concentration
of tryptophol. Its concentration average range in red wines is between
3.1. Analytical strategy 0.51 and 2.2 mg/L (Bordiga et al., 2016), while in our wine samples
tryptophol turned out to be occurring at concentration approximately
A sample of Aglianico red wine, obtained from grapes harvested 10-fold higher (around 20 mg/L). The high concentration of tryptophol
during the autumn of 2017, was passed through an Amberlite XAD-2 is consistent with the unusual high amounts of tryptophan (0.07 mg/gr)
column and three fractions were collected on the basis of the eluents estimated in the grapes from which the analyzed wine had been ob-
that, in the order, were water (fraction A), EtOAc (fraction B) and tained. This datum can be explained by taking into account that the
MeOH (fraction C). Preliminary NMR investigations led to the identi- summer of 2017, after which the analyzed grapes where harvested, was
fication in fraction A of resonances attributed to aminoacids, carbo- a quite dry season. It has been reported that high amounts of trypto-
hydrates, polyols and organic acids, and in fraction B of signals typical phan were detected in grapes and musts in exceptionally dry years as
of anthocyanins, mainly malvidin-3-O-glucoside, and tannins. The opposed to relatively damp seasons when the concentration of free and
presence of a complex mixture of metabolites was detected in fraction bound tryptophan is significantly lower (Hoenicke, Simat, Steinhart,
B. Thus, it was further separated by CombiFlash column chromato- Kohler, & Schwab, 1999).
graphy on silica gel. The identity of the eluted specialized metabolites The presence of tryptophol and tyrosol in high concentrations is of
(Table 1) was ascertained by High Resolution Mass Spectrometry ana- great pharmacological interest on account of their several health en-
lysis and by cross-interpreting their 1D (1H- and 13C NMR) and 2D hancing properties, including antioxidant, anticarcinogenic, cardio-
(COSY, TOCSY, ROESY, HSQC and HMBC) NMR spectra. Comparison of preventive and even antimicrobial bioactivities (Covas et al., 2003).
the metabolites NMR spectroscopic properties with those available in Moreover, our study led to the identification for the first time in red
the metabolomics data repositories confirmed our structural wine of another intermediate of the yeast tryptophan metabolism:

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M. Forino et al. Food Chemistry 278 (2019) 497–501

Fig. 1. 1H NMR spectra of fractions containing resonances assigned to the major secondary metabolites identified in wine.

Fig. 2. 1H NMR spectra of oleanic acid (top) and of xanthurenic acid (bottom).

xanthurenic acid (Fig. 2). Its concentration was in the range of 10 mg/L class, natural compounds characterized by carbon skeletons consisting
and its occurrence widens the already large plethora of wine bioactive of successive inclusions of C5 isoprene units successively subjected to
phytochemicals. More specifically, recent evidence has shown that numerous chemical modifications, usually involving oxygen atom in-
xanthurenic acid can have impact on brain function and neuro- clusions (Fig. 2). The occurrence of terpenoids in wines is not unusual,
transmission by interaction with metabotropic glutamate receptors, given that several monoterpenoids and sesquiterpenoids, constituted by
even if it has been suggested that its bioactivity may be extending also 2 or 3 isoprene units respectively, are well known odorous molecules
to several others molecular targets. As a consequence, xanthurenic acid responsible for the typical wine aromas. However, never was a tri-
has been the focus of still in progress multidisciplinary researches terpenoid reported in wines. Oleanic acid is a pentacyclic triterpenoid
aimed at investigating its biological function, with the final purpose of deriving by successive inclusions of six isoprene units. It is widely
better understanding the sophisticated correlation between tryptophan distributed in plants and in grape berries it is a key constituent of the
metabolism and brain physiology. The outcome of such studies may be protective bloom covering the skin (Szakiel, Paczkowski, Pensec, &
the discovery of new potential targets to cure nervous system diseases. Bertsch, 2012). Oleanic acid was detected in the berry skins we ana-
Another interesting bioactive molecule we isolated and for the first lyzed at concentration of about 0.85 mg/gr, while in wine it was esti-
time identified in wine was oleanic acid belonging to the terpenoid mated to be occurring at the significant concentration of 30 mg/L.

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M. Forino et al. Food Chemistry 278 (2019) 497–501

Oleanic acid is an interesting bioactive compound displaying a wide Funding


selection of beneficial effects that range from antitumor and anti-in-
flammatory to antiviral and antibiotic properties (Lin, Wen, & Sun, This research did not receive any specific grant from funding
2016). From an enological standpoint, it is important to underline that agencies in the public, commercial, or not-for-profit sectors.
oleanic acid determines an increase of the number of viable yeasts
during fermentation (Larue, Lafon-Lafourcade, & Ribereau-Gayon, Declaration of interest
1980). As the lack of grape lipids can induce nutritional limitation of
yeast activities in musts with a concomitant deficiency in assimilable None.
nitrogen (Casalta, Cervi, Salmon, & Sablayrolles, 2013), it is possible
that the presence of oleanic acid in wine could be due to a regular References
fermentation in a medium rich of nutrients.
The presence of xanthurenic acid and oleanic acid in wine increases Artero, A., Artero, A., Tarin, J. J., & Cano, A. (2015). The impact of moderate wine
the number of health promoting molecules in red wines, while raising consumption on health. Maturitas, 80(1), 3–13.
Bordiga, M., Lorenzo, C., Pardo, F., Salinas, M. R., Travaglia, F., Arlorio, M., ... Garde-
questions about their possible sensorial implications for wine. In this Cerdán, T. (2016). Factors influencing the formation of histaminol, hydroxytyrosol,
regards, further studies will be conducted considering that secondary tyrosol, and tryptophol in wine: Temperature, alcoholic degree, and amino acids
metabolites play a key role in defining the unique specificity of high concentration. Food Chemistry, 197, 1038–1045.
Brown, L., Kroon, P. A., Das, D. K., Das, S., Tosaki, A., Chan, V., ... Feick, P. (2009). The
quality products. biological responses to resveratrol and other polyphenols from alcoholic beverages.
Alcoholism, Clinical and Experimental Research, 33, 1513–1523.
Casalta, E., Cervi, M. F., Salmon, J. M., & Sablayrolles, J. M. (2013). White wine fer-
4. Conclusions mentation: Interaction of assimilable nitrogen and grape solids on alcoholic fer-
mentation under oenological conditions. Australian Journal of Grape and Wine
Research, 19, 47–52.
For the first time a systematic quali-quantitative analysis of the Chang, Y. C., Tsai, M. H., Sheu, W. H. H., Hsieh, S. C., & Chiang, A. N. (2013). The
health promoting phytochemicals contained in wine was carried out. therapeutic potential and mechanisms of action of quercetin in relation to lipopoly-
The adopted analytical strategy was based on a combination of chro- saccharide-induced sepsis in vitro and in vivo. PLoS ONE, 2013(8), e80744.
Covas, M. I., Miro-Casas, E., Fito, M., Farre-Albadalejo, M., Gimeno, E., Marrugat, J., & De
matography and untargeted NMR investigation. The profile of wine
La Torre, R. (2003). Bioavailability of tyrosol, an antioxidant phenolic compound
bioactive molecules we defined turned out to be more complex and present in wine and olive oil, in humans. Drugs under Experimental and Clinical
diversified than previously reported. In addition to polyphenols that Research, 29, 203–206.
constitute the typical wine beneficial molecules, unusual high con- Francis, L., & Newton, J. L. (2005). Determining wine aroma from compositional data.
Australian Journal of Grape and Wine Research, 11(2), 114–126.
centrations of both tryptophol and tyrosol were detected. Even more Gresele, P., Cerletti, C., Guglielmini, G., Pignatelli, P., de Gaetano, G., & Violi, F. (2011).
interesting, two bioactive molecules, namely xanthurenic acid and Effects of resveratrol and other wine polyphenols on vascular function: An update.
oleanic acid, were discovered in wine for the first time. Xanthurenic The Journal of Nutritional Biochemistry, 22, 201–211.
Gris, E. F., Mattivi, F., Ferreira, E. A., Vrhovsek, U., Filho, D. W., Pedrosa, R. C., &
acid is a natural product of the tryptophan metabolism and has lately Bordignon-Luiz, M. T. (2011). Stilbenes and tyrosol as target compounds in the as-
been the focus of many scientific studies due to its interaction with the sessment of antioxidant and hypolipidemic activity of Vitis vinifera red wines from
brain function and in particular with the metabotropic glutamate re- southern Brazil. Journal of Agricultural and Food Chemistry, 59(14), 7954–7961.
Haseeb, S., Alexander, B., & Baranchuk, A. (2017). Wine and cardiovascular health a
ceptors. Oleanic acid, a triterpenoid naturally present on the berry comprehensive review. Circulation, 136, 1434–1448.
skins, is endowed with many biological properties ranging from anti- Hoenicke, K., Simat, T. J., Steinhart, H., Kohler, H. J., & Schwab, A. (1999).
tumor and anti-inflammatory to antiviral and antibiotic activities. Determination of free and conjugated indole-3-acetic acid, tryptophan, and trypto-
phan metabolites in grape must and wine. Journal of Agricultural and Food Chemistry,
In perspective, the adopted scientific approach will be applied to 49(11), 5494–5501.
wine samples obtained from other grape varieties to investigate their Larue, F., Lafon-Lafourcade, S., & Ribereau-Gayon, P. (1980). Relationship between the
chemical composition specifically in terms of specialized metabolites. sterol content of yeast cells and their fermentation activity in grape must. Applied and
Environmental Microbiology, 39(4), 808–811.
Such research line has the double goal of contributing to fill the
Lin, C., Wen, X., & Sun, H. (2016). Oleanolic acid derivatives for pharmaceutical use: A
knowledge gap about the profile of the beneficial compounds contained patent review. Expert opinion on therapeutic patents, 26(6), 643–655.
in wine, and of tracing back the possible viticultural variables that Stockley, C., Teissedre, P. L., Boban, M., Di Lorenzo, C., & Restani, P. (2012).
determine the accumulation of the bioactive phytochemicals in grapes, Bioavailability of wine-derived phenolic compounds in humans: A review. Food &
Function, 3, 995–1007.
with the ultimate purpose of understanding how to modulate their Szakiel, A., Paczkowski, C., Pensec, F., & Bertsch, C. (2012). Fruit cuticular waxes as a
transfer into wines by appropriate vinification procedures. source of biologically active triterpenoids. Phytochemistry Reviews, 11(2–3), 263–284.

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