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. 2009 Nov 17;14(11):4669-81.
doi: 10.3390/molecules14114669.

New lipophilic piceatannol derivatives exhibiting antioxidant activity prepared by aromatic hydroxylation with 2-iodoxybenzoic acid (IBX)

Roberta Bernini  1 , Maurizio Barontini, Carmela Spatafora
Affiliations

New lipophilic piceatannol derivatives exhibiting antioxidant activity prepared by aromatic hydroxylation with 2-iodoxybenzoic acid (IBX)

Roberta Bernini et al. Molecules. .

Abstract

Piceatannol (E-3,5,3',4'-tetrahydroxystilbene) is a phytoalexin synthesized in grapes in response to stress conditions. It exhibits strong antioxidant and antileukaemic activities due to the presence of the catechol moiety. To modify some physical properties like solubility, and miscibility in non-aqueous media some new previously unreported piceatannol derivatives having lipophilic chains on the A-ring were prepared in good yields by a simple and efficient procedure. The key step was a chemo- and regioselective aromatic hydroxylation with 2-iodoxybenzoic acid (IBX). The new compounds showed antioxidant activity and seemed promising for possible applications as multifunctional emulsifiers in food, cosmetic and pharmaceutical fields.

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Figures

Figure 1
Figure 1
Chemical structure of natural stilbenes 1 and 2.
Figure 2
Figure 2
Chemical structure of 2-iodoxybenzoic acid (IBX).
Scheme 1
Scheme 1
Synthesis of 3,5-di-O-acetylresveratrol derivatives 4a-d.
Scheme 2
Scheme 2
Aromatic hydroxylation of 3,5-di-O-acyl resveratrol derivatives 4a-d.
Figure 4
Figure 4
13C-NMR spectrum (180-110 ppm region) of 3,5-di-O-acetyl piceatannol (5a).
Scheme 3
Scheme 3
Acetylation of 3,5-di-O-acyl piceatannol derivative 4a.
Figure 5
Figure 5
DPPH• scavenging activity of compounds 5a-d expressed as 100/SC50.
See this image and copyright information in PMC

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