Journal Article

Structural characterization and evaluation of antimicrobial and cytotoxic activity of six plant phenolic acids

Wydro, Urszula, Kalinowska, Monika, Jabłońska-Trypuć, Agata, Kozłowski, Maciej, Koronkiewicz, Kamila, Świsłocka, Renata, Piekut, Jolanta, Wołejko, Elżbieta, Lewandowski, Włodzimierz

2024

Overview

Phenolic acids still gain significant attention due to their potential antimicrobial and cytotoxic properties. In this study, we have investigated the antimicrobial of six phenolic acids, namely chlorogenic, caffeic, p -coumaric, rosmarinic, gallic and tannic acids in the concentration range 0.5–500 μM, against Escherichia coli and Lactobacillus rhamnosus . The antimicrobial activity was evaluated using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide colorimetric assay. Additionally, the cytotoxic effects of these phenolic acids on two cancer cell lines, the colorectal adenocarcinoma Caco-2 cell line and Dukes’ type C colorectal adenocarcinoma DLD-1 cell line was examined. To further understand the molecular properties of these phenolic acids, quantum chemical calculations were performed using the Gaussian 09W program. Parameters such as ionization potential, electron affinity, electronegativity, chemical hardness, chemical softness, dipole moment, and electrophilicity index were obtained. The lipophilicity properties represented by logP parameter was also discussed. This study provides a comprehensive evaluation of the antimicrobial and cytotoxic activity of six phenolic acids, compounds deliberately selected due to their chemical structure. They are derivatives of benzoic or cinnamic acids with the increasing number of hydroxyl groups in the aromatic ring. The integration of experimental and computational methodologies provides a knowledge of the molecular characteristics of bioactive compounds and partial explanation of the relationship between the molecular structure and biological properties. This knowledge aids in guiding the development of bioactive components for use in dietary supplements, functional foods and pharmaceutical drugs.

• Publisher: Public Library of Science
• Subject: Acids / Adenocarcinoma / Amino acids / Analysis / Anti-Infective Agents - chemistry / Anti-Infective Agents - pharmacology / Antimicrobial activity / Antimicrobial agents / Antioxidants / Apoptosis / Aromatic compounds / Bacteria / Bioactive compounds / Biological activity / Biological properties / Biology and Life Sciences / Bromides / Caco-2 Cells / Caffeic Acids - chemistry / Caffeic Acids - pharmacology / Cancer / Cell cycle / Cell death / Cell growth / Cell Line, Tumor / Cinnamates - chemistry / Cinnamates - pharmacology / Cinnamic acid / Colorectal cancer / Colorimetry / Coumaric Acids - chemistry / Coumaric Acids - pharmacology / Cytotoxicity / Dietary supplements / Dipole moments / E coli / Electron affinity / Electronegativity / Escherichia coli / Escherichia coli - drug effects / Ethylenediaminetetraacetic acid / Functional foods / Functional foods & nutraceuticals / Gallic Acid - chemistry / Gallic Acid - pharmacology / Gene expression / Herbs / Humans / Hydroxybenzoates - chemistry / Hydroxybenzoates - pharmacology / Hydroxyl groups / Ionization / Ionization potentials / Medicine and Health Sciences / Methicillin / Microbial Sensitivity Tests / Microorganisms / Molecular properties / Molecular structure / Parameters / Permeability / Phenolic acids / Phenols / Physical Sciences / Quantum chemistry / Research and Analysis Methods / Salmonella / Softness / Structural analysis / Tannic acid / Tea / Tumor cell lines