Reactivity of wine polyphenols under oxidation conditions: Hemisynthesis of adducts between grape catechins or oak ellagitannins and odoriferous thiols

Petit, Emilie; Jacquet, Rémi; Pouységu, Laurent; Deffieux, Denis; Quideau, Stéphane

doi:10.1016/j.tet.2018.11.071

Cited by 12 publications

(8 citation statements)

References 84 publications

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“…The orientation of the hydroxyl group at the C1 position of the C -glycosidic ETs, such as vescalagin and castalagin, has been shown to affect both their physicochemical properties as well as bioactivities. ,,− In the present study, the orientation of the hydroxyl group at the anomeric carbon affected both the ICF AVER and the ICF INIT values as could be seen when comparing monomer pairs 17 versus 18 , 19 versus 20 , 21 versus 22 and the dimers 29 – 32 . In the monomers, α-orientation resulted in more efficient complex formation in all three pairs, the effect being greatest between 17 and 18 (ICF AVER 0.35 → 0.86, ICF INIT 0.51 → 0.27) and lower between 19 and 20 (ICF AVER 0.50 → 0.71, ICF INIT 0.50 → 0.37) and between 21 and 22 (ICF AVER 0.45 → 0.60, ICF INIT 0.41 → 0.36).…”

Section: Results and Discussionmentioning

confidence: 50%

Structural Features of Hydrolyzable Tannins Determine Their Ability to Form Insoluble Complexes with Bovine Serum Albumin

Engström

Arvola

Nenonen

et al. 2019

J. Agric. Food Chem.

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The ability of 32 purified and characterized hydrolyzable tannins to form insoluble complexes with model protein bovine serum albumin was investigated with a turbidimetric 96-well plate reader method. The results showed a clear relationship between the hydrolyzable tannin structure and the intensity of haze that formed during the tannin–protein complexation. In addition to molecular weight, structural features such as number of galloyl groups, degree of oxidative coupling between the galloyls, positional isomerism, and cyclic vs acyclic glucose core were the major structural features that affected the ability of the monomeric hydrolyzable tannins to form insoluble complexes with bovine serum albumin. While oligomers were superior to monomers in their capability to precipitate the model protein, their activity depended less on the functional groups, but mostly on their size and overall flexibility. These results allowed us to construct an equation that predicted the protein precipitation capacity of the studied hydrolyzable tannins with high accuracy.

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Section: Results and Discussionmentioning

confidence: 50%

Structural Features of Hydrolyzable Tannins Determine Their Ability to Form Insoluble Complexes with Bovine Serum Albumin

Engström

Arvola

Nenonen

et al. 2019

J. Agric. Food Chem.

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“…The analysis of 3MH and 4MMP in juices after sonication would have not, however, give a certain explanation. Both compounds have been reported to react with catechins [44,45], which concentration is, inter alia, enhanced by treatment. Moreover, the degradation of the sulfhydryl groups of the compounds formed cannot be excluded.…”

Section: Ultrasound Application On Grape Mustmentioning

confidence: 99%

Evidence of the Possible Interaction between Ultrasound and Thiol Precursors

Román

Tonidandel

Nicolini

et al. 2020

Foods

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The effect of ultrasound (20 kHz, 153 μm) on the prefermentation extraction mechanisms in Sauvignon Blanc grapes was studied, focusing on 3-mercaptohexan-1-ol (3MH) and 4-mercapto-4-methyl-pentan-2-one (4MMP) precursors linked to glutathione (GSH) and cysteine (Cys). The treatment determined a positive extraction trend between the duration (untreated, 3 and 5 min) and the conductivity or the concentration of catechins and total phenols, significantly differentiated after 5 min. Nevertheless, the concentration of the thiol precursors in grape juice not only remained undifferentiated, but that of 3-S-glutathionyl mercaptohexan-1-ol showed a negative trend with the treatment time applied (168 ± 43, 156 ± 36, and 149 ± 32 μg/L, respectively, for control, 3 and 5 min). The divergence on the effect between families of compounds suggests an interaction between the sonication treatment and thiol precursor molecules. In order to evaluate the possible degradation properly, ultrasound was applied in a model solution spiked with 3MH and 4MMP precursors, reproducing the conditions of grapes. Except for Cys-3MH, the mean concentration (n = 5) for the rest of the precursors was significantly lower in treated samples, predominantly in those linked to glutathione (~−22% and ~18% for GSH-3MH and GSH-4MMP) rather than to cysteine (~−6%~−8% for Cys-3MH and Cys-4MMP). The degradation of precursors was associated with a significant increase of 3MH and 4MMP. The formation of volatile thiols following sonication is interesting from a technological point of view, as they are key aroma compounds of wine and potentially exploitable in the wine industry through specific vinification protocols.

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“…2 Similar addition reactions also feature prominently in other biochemical pathways, including the metabolism of aromatic rings, 17 mussel adhesion, 18 and the aging of wine. 19 Relatively recent applications in chemical biology have also capitalized on quinone-thiol coupling reactions. 20 However, the transformation has received comparatively little attention from the synthetic community, with notable exception of Prota's pioneering work 21 investigating the pheomelanogenic pathway.…”

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confidence: 99%

“…The quinone-thiol coupling reaction in the early stages of pheomelanogenesis installs an aryl C–S bond in a selective fashion under uniquely mild and atom-economic conditions . Similar addition reactions also feature prominently in other biochemical pathways, including the metabolism of aromatic rings, mussel adhesion, and the aging of wine . Relatively recent applications in chemical biology have also capitalized on quinone-thiol coupling reactions …”

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confidence: 99%

“…Previous studies on the addition of thiols to ortho -quinones have been examined within a relatively narrow substrate scope. ,− We attribute this lack of development to many of the well-known challenges of working with ortho -quinones, including poor regioselectivity in addition reactions and their redox lability. ortho -Quinones are both electrophiles and oxidants, and the catechols that result from tautomerization following addition are electron rich (Scheme B).…”

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confidence: 99%

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A Bioinspired Synthesis of 1,4-Benzothiazines by Selective Addition of Sulfur Nucleophiles to ortho-Quinones

Halloran

Esguerra

et al. 2023

J. Org. Chem.

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Herein, we report a bioinspired approach to the synthesis of 1,4-benzothiazines by drawing inspiration from the biosynthesis of pheomelanin pigments (pheomelanogenesis). In this context, general conditions for the regioselective coupling reaction between ortho-quinones and thiols were developed. The mild conditions proved amenable to a wide scope of both thiol and ortho-quinone coupling partners while simultaneously suppressing redox-exchange. The utility of this methodology was demonstrated by a synthesis of 1,4-benzothiazines, following a biomimetic, oxidative cyclization.

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Reactivity of wine polyphenols under oxidation conditions: Hemisynthesis of adducts between grape catechins or oak ellagitannins and odoriferous thiols

Cited by 12 publications

References 84 publications

Structural Features of Hydrolyzable Tannins Determine Their Ability to Form Insoluble Complexes with Bovine Serum Albumin

Structural Features of Hydrolyzable Tannins Determine Their Ability to Form Insoluble Complexes with Bovine Serum Albumin

Evidence of the Possible Interaction between Ultrasound and Thiol Precursors

A Bioinspired Synthesis of 1,4-Benzothiazines by Selective Addition of Sulfur Nucleophiles to ortho-Quinones

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