Abstract
Phenolic acids and their derivatives found in nature are well-known for their potential biological activity. In this study, two amides derived from trans-caffeic/ferulic acid and dopamine were synthesized and characterized by Fourier-transform infrared spectroscopy (FTIR), mass spectrometry, proton and carbon-13 nuclear magnetic resonance spectroscopy. The compounds were tested for the inhibition of acetylcholinesterase (AChE) from Electrophorus electricus and for antioxidant activity by scavenging 2,2-diphenyl-1-pycrylhydrazyl free radical (DPPH•) and 2,2′-azinobis(3-ethylbenzothiazoline-6-sulphonic acid) radical cation (ABTS•+), reducing ferric ions, and ferrous ions chelation. N-trans-Feruloyldopamine displayed the highest inhibitory effect on AChE with half-maximal inhibitory concentration (IC50) values of 8.52 μM. In addition, an in silico study was done to determine the most favorable AChE cluster with the synthesized compounds. Further, these clusters were investigated for binding positions at the lowest free binding energy. Both synthesized hydroxycinnamates were found to be better antioxidants than the parent acids in in vitro tests applied. N-trans-Caffeoyldopamine showed the best antioxidant activity in the three tested methods—against non-biological stable free radicals IC50 5.95 μM for DPPH•, 0.24 μM for the ABTS•+ method, and for reducing power (ascorbic acid equivalent (AAE) 822.45 μmol/mmol)—while for chelation activity against Fe2+ ions N-trans-feruloyldopamine had slightly better antioxidant activity (IC50 3.17 mM).
Highlights
Phenolic acids constitute a family of natural compounds that can be found in a wide variety of plants and food [1]
Derivatives of phenolic acids, which primarily include esters, ethers, glycosides, and amides, were tested and showed various biological activities [9,10,11]. Some of these derivatives belong to clovamide type derivatives that can be found in nature [11,12] but have been synthesized [13]
Both synthesized derivatives are characterized by several instrumental methods and the obtained results were related to the proposed structures
Summary
Phenolic acids constitute a family of natural compounds that can be found in a wide variety of plants and food [1]. The compounds are known to have acetylcholinesterase (AChE)-inhibitory [2], antibacterial [3], anti-inflammatory [4], antioxidant [5,6], antiviral [7], and immunomodulatory [8] properties These properties are associated with either their properties as antioxidants and enzyme inhibitors or their binding activity with specific receptors. Derivatives of phenolic acids, which primarily include esters, ethers, glycosides, and amides, were tested and showed various biological activities [9,10,11] Some of these derivatives belong to clovamide type derivatives that can be found in nature [11,12] but have been synthesized [13]
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
