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Review
. 2020 Oct 8;13(19):4454.
doi: 10.3390/ma13194454.

Biologically Active Compounds of Plants: Structure-Related Antioxidant, Microbiological and Cytotoxic Activity of Selected Carboxylic Acids

Beata Godlewska-Żyłkiewicz  1 , Renata Świsłocka  2 , Monika Kalinowska  2 , Aleksandra Golonko  3 , Grzegorz Świderski  2 , Żaneta Arciszewska  1 , Edyta Nalewajko-Sieliwoniuk  1 , Monika Naumowicz  4 , Włodzimierz Lewandowski  2
Affiliations
Review

Biologically Active Compounds of Plants: Structure-Related Antioxidant, Microbiological and Cytotoxic Activity of Selected Carboxylic Acids

Beata Godlewska-Żyłkiewicz et al. Materials (Basel). .

Abstract

Natural carboxylic acids are plant-derived compounds that are known to possess biological activity. The aim of this review was to compare the effect of structural differences of the selected carboxylic acids (benzoic acid (BA), cinnamic acid (CinA), p-coumaric acid (p-CA), caffeic acid (CFA), rosmarinic acid (RA), and chicoric acid (ChA)) on the antioxidant, antimicrobial, and cytotoxic activity. The studied compounds were arranged in a logic sequence of increasing number of hydroxyl groups and conjugated bonds in order to investigate the correlations between the structure and bioactivity. A review of the literature revealed that RA exhibited the highest antioxidant activity and this property decreased in the following order: RA > CFA ~ ChA > p-CA > CinA > BA. In the case of antimicrobial properties, structure-activity relationships were not easy to observe as they depended on the microbial strain and the experimental conditions. The highest antimicrobial activity was found for CFA and CinA, while the lowest for RA. Taking into account anti-cancer properties of studied NCA, it seems that the presence of hydroxyl groups had an influence on intermolecular interactions and the cytotoxic potential of the molecules, whereas the carboxyl group participated in the chelation of endogenous transition metal ions.

Keywords: antibacterial; antioxidant; cytotoxic activity; hydroxyl groups; natural carboxylic acids; phenolic acids; structure-activity relationship.

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Conflict of interest statement

No conflicts of interest have been declared.

Figures

Figure 1
Figure 1
Chemical structures of reviewed natural carboxylic acids (NCA): benzoic acid (BA), cinnamic acid (CinA), p-coumaric acid (p-CA), caffeic acid (CFA), rosmarinic acid (RA), and chicoric acid (ChA).
Figure 2
Figure 2
Selected mechanism of antimicrobial action of plant-derived carboxylic acids. [Based on [131]] Anti-quorum sensing. The quorum-sensing communication system can be inhibited in several different ways: Inhibition of autoinducers synthesis and transport, antagonist activity for autoinducers-receptors, and also direct reaction or inhibition of autoinducer activity. Changes in membrane properties. Phenolic acids (especially hydrophobic compounds) affect the properties of cell membranes (charge, permeability) through changes in hydrophobicity, reduction of negative surface charge, and the formation of pores in the membranes and leakage of intracellular components [135,136]. Anti-biofilm formation. Limiting the formation of biofilm by phenolic acids involves limiting cell adhesion to the surface and inhibiting biofilm maturation, indirectly through anti-quorum sensing action and inhibition of the expression of genes involved in biofilm formation [137,138]. Interference with the ATP generating system. Phenolic acids, by increasing the permeability of cell membranes, leak ions and partially inhibit the activity of ATPase [139] and other proteins, including enzymatic (enzymes inhibition). Acids with strong nucleophilic properties (e.g., CA) can donate an electron pair to electrophilic functional group of plasma membrane proteins and lipids leading to the membrane destabilization [140].
Figure 3
Figure 3
Selected molecular mechanisms of action of carboxylic acids from food sources. (HDAC—histone deacetylase).
See this image and copyright information in PMC

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