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

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Roberta BerniniCarmela Spatafora

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.

Citations

Jan 29, 2011·Angewandte Chemie·Alexander Duschek, Stefan F Kirsch
Nov 19, 2013·Phytochemistry·Gloria CastellanoFrancisco Torrens
Mar 28, 2017·Bioscience, Biotechnology, and Biochemistry·Yasunobu YamashitaTakeshi Sugai
Jan 29, 2019·Mini Reviews in Medicinal Chemistry·Qing-Shan LiBan-Feng Ruan
Sep 8, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Luce M MattioAndrea Pinto
Dec 22, 2019·Scientific Reports·Luce M MattioStefania Arioli
Apr 4, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Hideyasu ChinaToshifumi Dohi
Jan 21, 2011·The Journal of Organic Chemistry·Viktor V Zhdankin

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