In the present study the esterification of the OH groups of resveratrol, caffeic acid, ferulic acid, and -sitosterol with an antioxidant polyconjugated fatty acid, (2E,4E,6E)-octa-2,4,6-trienoic acid, was achieved. As the selective esterification of OH groups of natural compounds can affect their biological activity, a selective esterification of resveratrol and caffeic acid was performed by an enzymatic approach. The new resulting compounds were characterized spectroscopically (FT-IR, NMR mono, and bidimensional techniques); when necessary the experimental data were integrated by quantum chemical calculations. The antioxidant, anti-inflammatory and proliferative activity was evaluated. The good results encourage the use of these molecules as antioxidant and/or anti-inflammatory agents in dermocosmetic application.

Synthesis and biological evaluation of new natural phenolic (2E,4E,6E)-Octa-2,4,6-trienoic esters / R. Gandolfi, A. Contini, D. Pinto, B. Marzani, S. Pandini, D. Nava, E.R.E. Pini. - In: CHEMISTRY & BIODIVERSITY. - ISSN 1612-1872. - 14:12(2017 Dec), pp. e1700294.1-e1700294.14. [10.1002/cbdv.201700294]

Synthesis and biological evaluation of new natural phenolic (2E,4E,6E)-Octa-2,4,6-trienoic esters

R. Gandolfi;A. Contini;S. Pandini;D. Nava;E.R.E. Pini
2017

Abstract

In the present study the esterification of the OH groups of resveratrol, caffeic acid, ferulic acid, and -sitosterol with an antioxidant polyconjugated fatty acid, (2E,4E,6E)-octa-2,4,6-trienoic acid, was achieved. As the selective esterification of OH groups of natural compounds can affect their biological activity, a selective esterification of resveratrol and caffeic acid was performed by an enzymatic approach. The new resulting compounds were characterized spectroscopically (FT-IR, NMR mono, and bidimensional techniques); when necessary the experimental data were integrated by quantum chemical calculations. The antioxidant, anti-inflammatory and proliferative activity was evaluated. The good results encourage the use of these molecules as antioxidant and/or anti-inflammatory agents in dermocosmetic application.
natural products; selective esterification; biocatalysis; antioxidant activity; anti-inflammatory activity
Settore CHIM/06 - Chimica Organica
Settore CHIM/11 - Chimica e Biotecnologia delle Fermentazioni
dic-2017
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/528505
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