Antioxidant properties of several caffeic acid derivatives: A theoretical study

Abstract

Phenolic acids constitute a family of natural compounds that can be found in a wide variety of plants and food. Among them only ferulic, p-coumaric, chlorogenic, and caffeic acids were recently investigated. There are no data about antioxidant activity of single molecules of fertaric, coutaric, caftaric, dactylifric, and neochlorogenic acids and prenyl caffeate. In a continuation of our attempts to clarify their antioxidant activity, we present herein in silico studies concerning four mechanisms of interaction of phenolic antioxidants with free radicals: hydrogen atom transfer (HAT), (sequential proton loss electron transfer (SPLET), single electron transfer followed by proton transfer, and transition metals chelation, determining several parameters such as bond dissociation enthalpy; proton affinity; adiabatic ionization potential; highest occupied molecular orbital, lowest unoccupied molecular orbital, singly occupied molecular orbital; spin density; stabilization energy (DE ISO ); deprotonation enthalpy/energy (DH acidity and DG acidity ); and second-order perturbation energy E(2). We have proved that for all studied compounds the HAT mechanism was preferred in vacuum as well as in benzene and amyl acetate solvent media, whereas SPLET approach was significantly exposed especially in water. The most active antioxidants (according to the HAT approach) were compounds prenyl caffeate, methyl caffeate, and caffeic acid phenethyl ester, whereas the activity of trans and cis isomers of chicoric derivatives was related to the SPLET protocol. We also observed that trans isomers of caffeic, ferulic, and p-coumaric derivatives were not enough effective in all environments, when compared with other studied molecules. Moreover, we have noticed that the ortho position of the phenylic ring influenced profitably on antioxidant activity in all analyzed compounds.

Methyl Caffeate Isolated from the Flowers of Prunus persica (L.) Batsch Enhances Glucose-Stimulated Insulin Secretion

“…Interestingly, methyl caffeate ( 6 ) has a better effect than its free acid form, caffeic acid ( 5 ). Several studies on the biological activities of methyl caffeate ( 6 ) have reported its neuroprotective [ 36 ], anticancer [ 37 ], antioxidant [ 38 ], and anti-inflammatory effects [ 39 ] as well as antimicrobial and antimycobacterial activities [ 40 ]. Additionally, the induction of pancreatic islet β-cell regeneration by methyl caffeate ( 6 ) has also become clear [ 21 ], as its oral administration improved glucose tolerance in rats.…”

An In Silico Study of the Antioxidant Ability for Two Caffeine Analogs Using Molecular Docking and Quantum Chemical Methods

“…As well as molecular docking analysis, significant importance can be attributed to obtaining molecular descriptors and information obtained from chemical-quantum calculations. These data assist in the elucidation of various physical and chemical properties resulting from the different classes of existing compounds [ 10 ]. A study on the antioxidant activity of 4-hydroxyphenyl substituted thiopyrimidines has been performed using the Gaussian 9 program to obtain the energies of molecular orbitals (HOMO e LUMO) and evaluation of the electron donor and acceptor character of the chemical species under analysis [ 11 ].…”

Phytochemical content, antioxidant activity, and enzyme inhibition effect ofSalvia eriophoraBoiss. & Kotschy against acetylcholinesterase, α-amylase, butyrylcholinesterase, and α-glycosidase enzymes

“…Caffeic acid is one of the major hydroxycinnamic acids found in plants. In particular, it is one of the intensive phenolic acids found in potatoes, coffee, and wine, its derivatives have very good electron donating abilities (Urbaniak, Kujawski, Czaja, & Szelag, ), different caffeic acid derivatives have been stated as strong and selective matrix metalloproteinase‐9 (MMP‐9) inhibitors for the therapeutic treatment of cancer (Singh, Grewal, Pandita, & Lather, ).…”