Compounds with Antiviral, Anti-Inflammatory and Anticancer Activity Identified in Wine from Hungary's Tokaj Region via High Resolution Mass Spectrometry and Bioinformatics Analyses

Abstract

(1) Background: Wine contains a variety of molecules with potential beneficial effects on human health. Our aim was to examine the wine components with high-resolution mass spectrometry including high-resolution tandem mass spectrometry in two wine types made from grapes with or without the fungus Botrytis cinerea, or "noble rot". (2) For LC-MS/MS analysis, 12 wine samples (7 without and 5 with noble rotting) from 4 different wineries were used and wine components were identified and quantified. (3) Results: 288 molecules were identified in the wines and the amount of 169 molecules was statistically significantly different between the two wine types. A database search was carried out to find the molecules, which were examined in functional studies so far, with high emphasis on molecules with antiviral, anti-inflammatory and anticancer activities. (4) Conclusions: A comprehensive functional dataset related to identified wine components is also provided highlighting the importance of components with potential health benefits.

Keywords: LC-MS; functional food; high resolution mass spectrometry; metabolomics; wine.

Figure 1

Principal component analysis of “aszú” and “furmint” wine samples analyzed in positive panel (A) and negative panel (B) polarity mode. The “x” axis shows PC1 while the “y” axis shows PC2. The orange dots represent the “furmint” samples while the blue dots represent the “aszú” samples. The wineries are also indicated with numbering.

Figure 2

Hierarchical cluster analysis of the molecules identified in “aszú” and “furmint” wines registered in positive panel (A) and in negative panel (B) polarity mode. The green color indicates compounds with lower amount, while the red color shows compounds with higher amount in the comparison of “aszú” and “furmint” samples.

Figure 3

Comparative analysis of the identified compounds in “aszú” and “furmint” wines. The “x” axis represents the Log2 fold-change values, while the “y” axis indicates the –Log10 p values. The green box sows the compounds having statistically significantly higher level in “furmint” compared to “aszú”, while the red box indicates compounds with statistically significantly higher level in “aszú” compared to “furmint”. The top 10 components that showed the highest change in “furmint” and in “aszú”, repsepectively, are denoted with numbers (F1–F10 and A1–A10, respectively). F1: DL-isoleucyl-DL-isoleucyl-DL-histidine, F2: DL-alanyl-DL-isoleucyl-DL-isoleucyl-DL-threonine, F3: DL-leucyl-DL-leucyl-DL-leucine, F4: DL-valyl-DL-valyl-DL-valine, F5: L-phenylalanyl-L-leucine, F6: DL-tyrosyl-DL-prolyl-DL-isoleucine, F7: (2S)-2-[(2R)-7-(2-Methoxyethoxy)-5,8-dimethyl-1,2,3,4- tetrahydro-2-naphthalenyl]-1-(1-piperidinyl)-1-propanone, F8: DL-isoleucyl-DL-alpha-glutamyl-DL-lysine, F9: 1-(4-Methoxyphenyl)-N-[3-(4-morpholinyl)propyl]-5-oxo-3-pyrrolidinecarboxamide, F10: N-Isobutyrylglycylglycine, A1: Phenethylamine, A2: Perillartine, A3: DL-glutaminyl-DL-threonyl-DL-lysine, A4: N-Boc-Tyramine, A5: 4-(2,3-Dihydro-1,4-benzodioxin-6-yl)-4-oxobutanoic acid, A6: 1-Hydroxyhexane-1,2,6-tricarboxylate, A7: 2-Hydroxy-1-(6-hydroxy-2-isopropenyl-2,3-dihydro-1-benzofuran-5-yl)ethanone, A8: Rosin, A9: (2E)-3-(3,4-dimethoxyphenyl)prop-2-enoic acid, A10: N-[3-(4,11-Dimethyl-2-oxo-6,7,8,9-tetrahydro-2H-[1]benzofuro[3,2-g]chromen-3-yl)propanoyl]glycine.