Synthesis and Biological Evaluation of New Natural Phenolic (2E,4E,6E)‐Octa‐2,4,6‐trienoic Esters

• Published in: Chemistry & biodiversity 2017-12, Vol.14 (12), p.n/a
• Main Authors: Gandolfi, Raffaella, Contini, Alessandro, Pinto, Daniela, Marzani, Barbara, Pandini, Stefano, Nava, Donatella, Pini, Elena
• Format: Article
• Language: English
• Subjects: Anti-inflammatory agents; Antioxidant activity; Antioxidants; Antioxidants - chemical synthesis; Antioxidants - chemistry; Antioxidants - pharmacology; Anti‐inflammatory activity; Biocatalysis; Biological activity; Caffeic acid; Caffeic Acids - chemical synthesis; Caffeic Acids - chemistry; Cell Line; Cell Proliferation - drug effects; Cell Survival - drug effects; Data processing; Esterification; Esters; Esters - chemical synthesis; Esters - chemistry; Esters - pharmacology; Fatty acids; Ferulic acid; Fourier transforms; Humans; Hydrogen Peroxide - toxicity; Inflammation; Keratinocytes - cytology; Keratinocytes - drug effects; Keratinocytes - metabolism; Lipopolysaccharides - toxicity; Magnetic Resonance Spectroscopy; Natural products; NMR; Nuclear magnetic resonance; Oxidative Stress - drug effects; Phenolic compounds; Phenols; Phenols - chemical synthesis; Phenols - chemistry; Phenols - pharmacology; Quantum chemistry; Quantum Theory; Resveratrol; Selective esterification; Spectroscopy, Fourier Transform Infrared; Stereoisomerism
• ISSN: 1612-1872; 1612-1880
• DOI: 10.1002/cbdv.201700294

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, (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.