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Synthesis and Biological Evaluation of New Natural Phenolic (2 E ,4 E ,6 E )‐Octa‐2,4,6‐trienoic Esters
Author(s) -
Gandolfi Raffaella,
Contini Alessandro,
Pinto Daniela,
Marzani Barbara,
Pandini Stefano,
Nava Donatella,
Pini Elena
Publication year - 2017
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201700294
Subject(s) - chemistry , caffeic acid , ferulic acid , resveratrol , antioxidant , organic chemistry , molecule , quantum chemical , fatty acid , carbon 13 nmr , phenols , caffeic acid phenethyl ester , stereochemistry , biochemistry
In the present study the esterification of the OH groups of resveratrol, caffeic acid, ferulic acid, and β ‐sitosterol with an antioxidant polyconjugated fatty acid, (2 E ,4 E ,6 E )‐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.