Correlations between molecular structure and biological activity in "logical series" of dietary chromone derivatives. 2020

Włodzimierz Lewandowski, and Hanna Lewandowska, and Aleksandra Golonko, and Grzegorz Świderski, and Renata Świsłocka, and Monika Kalinowska
Department of Chemistry, Biology and Biotechnology, Bialystok University of Technology, Bialystok, Poland.

The research was conducted in the "logical series" of seven ligands: chromone, flavone, 3-hydroxyflavone, 3,7-dihydroxyflavone, galangin, kaempferol and quercetin. Each subsequent ligand differs from the previous one, among others by an additional hydroxyl group. The studied chromone derivatives are plant secondary metabolites which play an important role in growth, reproduction, and resistance to pathogens. They are important food ingredients with valuable pro-health properties. The studies of the relationships between their molecular structure and biological activity facilitate searching for new chemical compounds with important biological properties not by trial and error, but concerning the impact of specific changes in their structure on the compound properties. Therefore several pectroscopic methods (FT-IR, FT-Raman, 1H and 13C NMR) were applied to study the molecular structure of the compounds in the series. Moreover the quantum-chemical calculations at B3LYP/6-311++G** were performed to obtained the theoretical NMR spectra, NBO atomic charge, global reactivity descriptors and thermodynamic parameters. The antioxidant activity of the compounds was tested in the DPPH and FRAP assays and the mechanism of antioxidant activity was discussed based on the results on theoretical calculations. The cytotoxicity of the ligands toward human epithelial colorectal adenocarcinoma Caco2 cells was estimated and correlated with the lipophilicity of the compounds. The principal component analyses (PCA) and hierarchical cluster analysis were used to study the dependency between the molecular structure of ligands and their biological activity. The experimental data were related to the theoretical ones. The found regular changes in physicochemical properties correlated well with the systematic changes in antioxidant and biological properties.

UI MeSH Term Description Entries
D002867 Chromones 1,4-Benzopyrones,Chromone,1,4 Benzopyrones
D004032 Diet Regular course of eating and drinking adopted by a person or animal. Diets
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000077318 Density Functional Theory A theory that is used to describe the electronic ground state properties of matter. It forms the basis of methods in obtaining a solution to the Schrodinger equation for a many-body system, and to investigate the structural, magnetic, and electronic properties of molecules and materials. Density Functional Calculations,Density Functional Computations,Density Functional Theory Calculations,Density Functional Theory Computations,Td-DFT,Td-DFT Calculations,Td-DFT Computations,Time-Dependent Density Functional Theory,Time-Dependent Density Functional Theory Calculations,Time-Dependent Density Functional Theory Computations,DFT Calculations,KS-DFT,Kohn-Sham Density Functional Theory,Calculation, Density Functional,Calculation, Td-DFT,Computation, Density Functional,Computation, Td-DFT,DFT Calculation,Density Functional Calculation,Density Functional Computation,Density Functional Theories,Functional Calculation, Density,Functional Calculations, Density,Functional Computation, Density,Kohn Sham Density Functional Theory,Td DFT Calculations,Td DFT Computations,Td-DFT Calculation,Td-DFT Computation,Time Dependent Density Functional Theory,Time Dependent Density Functional Theory Calculations,Time Dependent Density Functional Theory Computations
D000970 Antineoplastic Agents Substances that inhibit or prevent the proliferation of NEOPLASMS. Anticancer Agent,Antineoplastic,Antineoplastic Agent,Antineoplastic Drug,Antitumor Agent,Antitumor Drug,Cancer Chemotherapy Agent,Cancer Chemotherapy Drug,Anticancer Agents,Antineoplastic Drugs,Antineoplastics,Antitumor Agents,Antitumor Drugs,Cancer Chemotherapy Agents,Cancer Chemotherapy Drugs,Chemotherapeutic Anticancer Agents,Chemotherapeutic Anticancer Drug,Agent, Anticancer,Agent, Antineoplastic,Agent, Antitumor,Agent, Cancer Chemotherapy,Agents, Anticancer,Agents, Antineoplastic,Agents, Antitumor,Agents, Cancer Chemotherapy,Agents, Chemotherapeutic Anticancer,Chemotherapy Agent, Cancer,Chemotherapy Agents, Cancer,Chemotherapy Drug, Cancer,Chemotherapy Drugs, Cancer,Drug, Antineoplastic,Drug, Antitumor,Drug, Cancer Chemotherapy,Drug, Chemotherapeutic Anticancer,Drugs, Antineoplastic,Drugs, Antitumor,Drugs, Cancer Chemotherapy
D000975 Antioxidants Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. Anti-Oxidant,Antioxidant,Antioxidant Activity,Endogenous Antioxidant,Endogenous Antioxidants,Anti-Oxidant Effect,Anti-Oxidant Effects,Anti-Oxidants,Antioxidant Effect,Antioxidant Effects,Activity, Antioxidant,Anti Oxidant,Anti Oxidant Effect,Anti Oxidant Effects,Anti Oxidants,Antioxidant, Endogenous,Antioxidants, Endogenous
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D057927 Hydrophobic and Hydrophilic Interactions The thermodynamic interaction between a substance and WATER. Hydrophilic Interactions,Hydrophilic and Hydrophobic Interactions,Hydrophilicity,Hydrophobic Interactions,Hydrophobicity,Hydrophilic Interaction,Hydrophilicities,Hydrophobic Interaction,Hydrophobicities,Interaction, Hydrophilic,Interaction, Hydrophobic,Interactions, Hydrophilic,Interactions, Hydrophobic
D018938 Caco-2 Cells Human colonic ADENOCARCINOMA cells that are able to express differentiation features characteristic of mature intestinal cells, such as ENTEROCYTES. These cells are valuable in vitro tools for studies related to intestinal cell function and differentiation. Caco 2 Cells,Caco-2 Cell,Cell, Caco-2,Cells, Caco-2

Related Publications

Włodzimierz Lewandowski, and Hanna Lewandowska, and Aleksandra Golonko, and Grzegorz Świderski, and Renata Świsłocka, and Monika Kalinowska
March 2012, Molecules (Basel, Switzerland),
Włodzimierz Lewandowski, and Hanna Lewandowska, and Aleksandra Golonko, and Grzegorz Świderski, and Renata Świsłocka, and Monika Kalinowska
October 1993, Carbohydrate research,
Włodzimierz Lewandowski, and Hanna Lewandowska, and Aleksandra Golonko, and Grzegorz Świderski, and Renata Świsłocka, and Monika Kalinowska
January 2014, Nucleosides, nucleotides & nucleic acids,
Włodzimierz Lewandowski, and Hanna Lewandowska, and Aleksandra Golonko, and Grzegorz Świderski, and Renata Świsłocka, and Monika Kalinowska
January 1977, Farmakologiia i toksikologiia,
Włodzimierz Lewandowski, and Hanna Lewandowska, and Aleksandra Golonko, and Grzegorz Świderski, and Renata Świsłocka, and Monika Kalinowska
June 1982, Journal of general microbiology,
Włodzimierz Lewandowski, and Hanna Lewandowska, and Aleksandra Golonko, and Grzegorz Świderski, and Renata Świsłocka, and Monika Kalinowska
March 1974, Acta pharmaceutica Hungarica,
Włodzimierz Lewandowski, and Hanna Lewandowska, and Aleksandra Golonko, and Grzegorz Świderski, and Renata Świsłocka, and Monika Kalinowska
November 1962, Nature,
Włodzimierz Lewandowski, and Hanna Lewandowska, and Aleksandra Golonko, and Grzegorz Świderski, and Renata Świsłocka, and Monika Kalinowska
February 1995, Genetika,
Włodzimierz Lewandowski, and Hanna Lewandowska, and Aleksandra Golonko, and Grzegorz Świderski, and Renata Świsłocka, and Monika Kalinowska
March 2021, Bioorganic & medicinal chemistry letters,
Włodzimierz Lewandowski, and Hanna Lewandowska, and Aleksandra Golonko, and Grzegorz Świderski, and Renata Świsłocka, and Monika Kalinowska
January 1955, Bulletin de l'Association francaise pour l'etude du cancer,
Copied contents to your clipboard!