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Review
. 2019 Oct 16;8(10):487.
doi: 10.3390/antiox8100487.

Chain Breaking Antioxidant Activity of Heavy (S, Se, Te) Chalcogens Substituted Polyphenols

Caterina Viglianisi  1 , Stefano Menichetti  2
Affiliations
Review

Chain Breaking Antioxidant Activity of Heavy (S, Se, Te) Chalcogens Substituted Polyphenols

Caterina Viglianisi et al. Antioxidants (Basel). .

Abstract

Polyphenols are probably the most important family of natural and synthetic chain-breaking antioxidants. Since long ago, chemists have studied how structural (bioinspired) modifications can improve the antioxidant activity of these compounds in terms of reaction rate with radical reactive oxygen species (ROS), catalytic character, multi-defence action, hydrophilicity/lipophilicity, biodistribution etc. In this framework, we will discuss the effect played on the overall antioxidant profile by the insertion of heavy chalcogens (S, Se and Te) in the phenolic skeleton.

Keywords: chain breaking antioxidants; polyphenols; selenium; sulfur; tellurium.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structure of model natural and synthetic phenolic antioxidants. BHT—butylated hydroxytoluene; HBA—butylated hydroxyanisole.
Figure 2
Figure 2
Electronic (red arrows) and intra-HB (green arrows) effects in modifying the ArO-H BDE value in substituted phenols. ED—electron-donating; EW—electron-withdrawing; BDE—Bond Dissociation Enthalpy.
Figure 3
Figure 3
Role of conformations on resonance stabilization of ArO•.
Figure 4
Figure 4
Effect of ring size on BDE of benzo-fused oxygen heterocycles.
Figure 5
Figure 5
Performances of Sulfur analogues of BHA 8, 9 and allrac-1-thio-α-tocopherol 10.
Figure 6
Figure 6
A selection of 2,3-dihydrobenzo[1,4]oxathiine multi-defence antioxidants.
Figure 7
Figure 7
Conformational and substitution considerations on intra-HB strength of acyclic and cyclic ortho-thioalkyl substituted phenols, and benzoxathiines 20–23 prepared to quantify the role of this phenomenon on kinh and ArO-H BDE.
Figure 8
Figure 8
Optimized benzoxathiines phenolic chain breaking antioxidants 24–26.
Figure 9
Figure 9
Hydroxy-2,3-dyhydrobenzo[b]thiophene antioxidants.
Figure 10
Figure 10
Effect of aromatization on chain breaking antioxidant activity of dihydrobenzo[b]furane/benzo[b]furane vs dihydrobenzo[b]thiophenes/benzo[b]thiophenes couples.
Figure 11
Figure 11
allrac-1-Seleno-α-tocopherol 36, and model chalcogen substituted polyphenols used to quantify the substitution contribution on chain breaking activity.
Figure 12
Figure 12
Heavy chalcogens (Se, Te) possible catalytic cycles (black frame, red frame and blue frame) in the presence of hydroperoxides or peroxyl radicals as oxidants and a sacrificial thiol as co-antioxidant.
Figure 13
Figure 13
A selection of potent Tellurium containing phenolic antioxidants prepared so far.
Figure 14
Figure 14
A selection of Selenium containing phenols prepared so far.
Figure 15
Figure 15
A selection of benzo[b]selenophenes antioxidants reported so far.
Figure 16
Figure 16
A selection of tocopherols analogues prepared so far.
Figure 17
Figure 17
Chalcogens containing ditocopherols prepared so far.
Figure 18
Figure 18
Role of intra-HB in δ,δ-ditocopheryl sulfide 79 and δ,δ-ditocopheryl disulfide 80.
See this image and copyright information in PMC

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