The Study of Anti-/Pro-Oxidant, Lipophilic, Microbial and Spectroscopic Properties of New Alkali Metal Salts of 5-O-Caffeoylquinic Acid

Abstract

Lithium, sodium, potassium, rubidium and caesium salts of 5-O-caffeoylquinic acid (chlorogenic acid, 5-CQA) were synthesized and described by FT-IR (infrared spectroscopy), FT-Raman (Raman spectroscopy), UV (UV absorption spectroscopy), 1H (400.15 MHz), 13C (100.63 MHz) NMR (nuclear magnetic resonance spectroscopy). The quantum–chemical calculations at the B3LYP/6-311++G** level were done in order to obtain the optimal structures, IR spectra, NBO (natural bond orbital) atomic charges, HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) orbitals and chemical reactivity parameters for 5-CQA and Li, Na and K 5-CQAs (chlorogenates). The DPPH (α, α-diphenyl-β-picrylhydrazyl) and FRAP (ferric reducing antioxidant power) assays were used for the preliminary estimation of the antioxidant properties of alkali metal chlorogenates and chlorogenic acid. In the DPPH assay the EC50 parameter were equal to 7.39 μM for 5-CQA and was in the range of 4.50–5.89 μM for salts. The FRAP values for two different concentrations (5 and 2.5 μM) of the studied compounds were respectively 114.22 and 72.53 μM Fe2+ for 5-CQA, whereas for salts they were 106.92–141.13 and 78.93–132.00 μM Fe2+. The 5-CQA and its alkali metal salts possess higher antioxidant properties than commonly applied antioxidants (BHA, BHT, l-ascorbic acid). The pro-oxidant action of these compounds on trolox oxidation was studied in the range of their concentration 0.05–0.35 μM. The lipophilicity (logkw) of chlorogenates and chlorogenic acid was determined by RP-HPLC (reverse phase—high performance liquid chromatography) using five different columns (C8, PHE (phenyl), CN (cyano), C18, IAM (immobilized artificial membrane)). The compounds were screened for their in vitro antibacterial activity against E. coli, Bacillus sp., Staphylococcus sp., Streptococcus pyogenes and antifungal activity against Candida sp. The 5-CQA possessed lower antibacterial (minimal inhibitory concentration, MIC = 7.06 mM) and antifungal (MIC = 14.11 mM) properties than its alkali metal salts (MIC values: 6.46–2.63 mM and 12.91–5.27mM, respectively). The synthesized chlorogenates possessed better antioxidant, lipophilic, antimicrobial as well as lower pro-oxidant properties than the ligand alone. Moreover, a systematic change of the activity of alkali metal salts along the series Li→Cs suggests that there are correlations between the studied biological properties. The type of metal cation in the carboxylate group of chlorogenate is crucial for the activity of studied compounds.

Zn(II) Complex of Plant Phenolic Chlorogenic Acid: Antioxidant, Antimicrobial and Structural Studies

“…The wavenumbers, intesities and assignment of selected bands from the FT-IR spectra of zinc chlorogenate, sodium chlorogenate[10] and chlorogenic acid[12]; the symbols denote: ν-stretching vibrations, δ-deforming in plane and oop-out of plane bending vibrations; s-strong, m-medium, w-week, v-very, sh-on the slope.…”

Synthesis and Evaluation of New Coumarin Derivatives as Antioxidant, Antimicrobial, and Anti-Inflammatory Agents

“…Moreover, lipophilicity affects not only the pharmacodynamic profile of the drug, but also its pharmacokinetics [ 29 ]. However, increasing the lipophilicity of a compound facilitates microbial cell penetration, hence improving antimicrobial activity [ 30 , 31 ]. In fact, only compound 7b was inactive against all tested microorganisms and showed the lowest consensus Log P- value (1.05) amongst all tested compounds, which may be attributed to its low Log P- value.…”

Spectroscopic, Theoretical and Antioxidant Study of 3d-Transition Metals (Co(II), Ni(II), Cu(II), Zn(II)) Complexes with Cichoric Acid

“…This creates the possibility of application of CA and its metal complexes in bio-formulations or biopreparations as strong antioxidants. The metal compounds of CA may be of special interest because they possess different physico-chemical properties than the ligand alone (e.g., increased solubility in the case of sodium salt), better lipophilicity [ 38 ] and they are an additional source of macro- and microelements.…”