Włodzimierz Lewandowski

Apples: Content of phenolic compounds vs. variety, part of apple and cultivation model, extraction of phenolic compounds, biological properties

Apples are among the most popular fruits in the world. They are rich in phenolic compounds, pectin, sugar, macro- and microelements. Applying different extraction techniques it is possible to isolate a particular group of compounds or individual chemicals and then test their biological properties. Many reports point to the antioxidant, antimicrobial, anticancer and many other beneficial effects of apple components that may have potential applications in food, pharmaceutical and cosmetic industries. This paper summarizes and compiles information about apple phenolic compounds, their biological properties with particular emphasis on health-related aspects. The data are reviewed with regard to different apple varieties, part of apple, cultivation model and methods of extraction.

The role of natural polyphenols in cell signaling and cytoprotection against cancer development

The cytoprotective and anticancer action of dietary in-taken natural polyphenols has for long been attributed only to their direct radical scavenging activities. Currently it is well supported that those compounds display a broad spectrum of biological and pharmacological outcomes mediated by their complex metabolism, interaction with gut microbiota as well as direct interactions of their metabolites with key cellular signaling proteins. The beneficial effects of natural polyphenols and their synthetic derivatives are extensively studied in context of cancer prophylaxis and therapy. Herein we focus on cell signaling to explain the beneficial role of polyphenols at the three stages of cancer development: we review the recent proceedings about the impact of polyphenols on the cytoprotective antioxidant response and their proapoptotic action at the premalignant stage, and finally we present data showing how phenolic acids (e.g., caffeic, chlorogenic acids) and flavonols (e.g., quercetin) hamper the development of metastatic cancer.

Spectroscopic (FT-IR, FT-Raman, 1H and 13C NMR) and theoretical studies of p-coumaric acid and alkali metal p-coumarates

The evaluation of the electronic charge distribution in metal complexes enables more precise interpretation of mechanism by which particular metal ions affect biochemical properties of ligands [J. Inorg. Biochem. 99 (2005), 1407–1423, J. Mol. Struct. 919 (2009), 284–289]. In this paper we investigated the influence of alkali metal cations (lithium, sodium, potassium, rubidium and cesium) on the electronic structure of p-coumaric acid (p-CA). It allowed to observe the systematic changes in the spectra of investigated complexes depending on the position of the element in the periodic table. p-Coumaric acid is a derivative of cinnamic acid that occurs in several plant species. Li, Na, K, Rb and Cs p-coumarates were synthesized and the experimental and theoretical FT-IR, FT-Raman, 1H and 13C NMR spectra of p-coumaric acid and its salts were registered and analyzed. The structures, atomic charges, infrared and NMR spectra of p-coumaric acid and Li, Na, K salts were calculated by B3LYP/6-311

Vibrational spectra of 5-halogenouracils part II—solids

Abstract The selected regions of FTIR and FTRaman spectra of polycrystalline uracil and all 5-halogenouracils are compared and interpreted in view of their crystal structures, and ab initio HF and MP2 calculations. The linear correlation between frequencies (both experimental and theoretical) as well as theoretical IR intensities and theoretical Raman activities, and the electronegativity, Cartledge ionic potential, and inverse mass of the halogen was tested for all studied modes.

Spectroscopic (FT-IR, FT-Raman, 1H- and 13C-NMR), Theoretical and Microbiological Study of trans o-Coumaric Acid and Alkali Metal o-Coumarates

This work is a continuation of research on a correlation between the molecular structure and electronic charge distribution of phenolic compounds and their biological activity. The influence of lithium, sodium, potassium, rubidium and cesium cations on the electronic system of trans o-coumaric (2-hydroxy-cinnamic) acid was studied. We investigated the relationship between the molecular structure of the tested compounds and their antimicrobial activity. Complementary molecular spectroscopic techniques such as infrared (FT-IR), Raman (FT-Raman), ultraviolet-visible (UV-VIS) and nuclear magnetic resonance (1H- and 13C-NMR) were applied. Structures of the molecules were optimized and their structural characteristics were calculated by the density functional theory (DFT) using the B3LYP method with 6-311++G** as a basis set. Geometric and magnetic aromaticity indices, atomic charges, dipole moments and energies were also calculated. Theoretical parameters were compared to the experimental characteristics of investigated compounds. Correlations between certain vibrational bands and some metal parameters, such as electronegativity, ionization energy, atomic and ionic radius, were found. The microbial activity of studied compounds was tested against Escherichia coli, Bacillus subtilis, Pseudomonas aeruginosa, Staphylococcus aureus, Proteus vulgaris and Candida albicans.

The relationship between molecular structure and biological activity of alkali metal salts of vanillic acid: Spectroscopic, theoretical and microbiological studies

In this paper we investigate the relationship between molecular structure of alkali metal vanillate molecules and their antimicrobial activity. To this end FT-IR, FT-Raman, UV absorption and (1)H, (13)C NMR spectra for lithium, sodium, potassium, rubidium and caesium vanillates in solid state were registered, assigned and analyzed. Microbial activity of studied compounds was tested against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Proteus vulgaris, Bacillus subtilis and Candida albicans. In order to evaluate the dependence between chemical structure and biological activity of alkali metal vanillates the statistical analysis was performed for selected wavenumbers from FT-IR spectra and parameters describing microbial activity of vanillates. The geometrical structures of the compounds studied were optimized and the structural characteristics were determined by density functional theory (DFT) using at B3LYP method with 6-311++G** as basis set. The obtained statistical equations show the existence of correlation between molecular structure of vanillates and their biological properties.

Spectroscopic (FT-IR, FT-Raman, 1H, 13C NMR, UV/VIS), thermogravimetric and antimicrobial studies of Ca(II), Mn(II), Cu(II), Zn(II) and Cd(II) complexes of ferulic acid.

The molecular structure of Mn(II), Cu(II), Zn(II), Cd(II) and Ca(II) ferulates (4-hydroxy-3-methoxycinnamates) was studied. The selected metal ferulates were synthesized. Their composition was established by means of elementary and thermogravimetric analysis. The following spectroscopic methods were used: infrared (FT-IR), Raman (FT-Raman), nuclear magnetic resonance ((13)C, (1)H NMR) and ultraviolet-visible (UV/VIS). On the basis of obtained results the electronic charge distribution in studied metal complexes in comparison with ferulic acid molecule was discussed. The microbiological study of ferulic acid and ferulates toward Escherichia coli, Bacillus subtilis, Candida albicans, Pseudomonas aeruginosa, Staphylococcus aureus and Proteus vulgaris was done.

Theoretical and experimental 1H, 13C, 15N, and 17O NMR spectra of 5-nitro, 5-amino, and 5-carboxy uracils

Abstract Theoretical and experimental 1 H, 13 C, 15 N, and 17 O NMR spectral parameters of uracil and 5-nitro, 5-amino and 5-carboxy uracils were determined and analyzed. The theoretical spectra were calculated by the CHF-GIAO method using the polarized double zeta Hansen–Bouman basis set and the polarized triple zeta Sadlej basis set. For all the nuclei studied, the effect of substituents on the chemical shifts of 1 H, 13 C, 15 N, and 17 O nuclei of 5-substituted uracils was analyzed. All the carbon–proton and one-bond carbon–carbon spin–spin coupling constants were also measured.

Alkali metal salts of rutin - Synthesis, spectroscopic (FT-IR, FT-Raman, UV-VIS), antioxidant and antimicrobial studies

In this work several metal salts of rutin with lithium, sodium, potassium, rubidium and cesium were synthesized. Their molecular structures were discussed on the basis of spectroscopic (FT-IR, FT-Raman, UV-VIS) studies. Optimized geometrical structure of rutin was calculated by B3LYP/6-311++G(∗∗) method and sodium salt of rutin were calculated by B3LYP/LanL2DZ method. Metal chelation change the biological properties of ligand therefore the antioxidant (FRAP and DPPH) and antimicrobial activities (toward Escherichia coli, Staphylococcus aureus, Enterococcus faecium, Proteus vulgaris, Pseudomonas aeruginosa, Klebsiella pneumonia, Candida albicans and Saccharomyces cerevisiae) of alkali metal salts were evaluated and compared with the biological properties of rutin.

Spectroscopic and magnetic properties of Cu(II) complexes with selected biologically important ligands

The aim of this work was to study the spectroscopic and magnetic properties of copper(II) o-, m-, p-aminobenzoates, o-, m-, p-methoxybenzoates and o-, m- and p-nitrobenzoates. The complexes were synthesized and their compositions were evaluated by elementary analysis. The infrared and Raman spectra for Cu(II) aminobenzoates, methoxybenzoates and nitrobenzoates were recorded and assigned. The obtained data were compared with those previously published for aminobenzoic, methoxybenzoic and nitrobenzoic acids and their sodium salts. The structures of Cu(II) o-, m-, p-aminobenzoates, o-, m-, p-methoxybenzoates and o-, m- and p-nitrobenzoates as well as the change in the electronic charges distribution caused by Cu(II) complex formation were discussed.