Seven derivatives of plant-derived hydroxybenzoic acid (HBA)—including 2,3-dihydroxybenzoic (2,3-DHB, pyrocatechuic), 2,4-dihydroxybenzoic (2,4-DHB, β-resorcylic), 2,5-dihydroxybenzoic (2,5-DHB, gentisic), 2,6-dihydroxybenzoic (2,6-DHB, γ-resorcylic acid), 3,4-dihydroxybenzoic (3,4-DHB, protocatechuic), 3,5-dihydroxybenzoic (3,5-DHB, α-resorcylic), and 3,4,5-trihydroxybenzoic (3,4,5-THB, gallic) acids—were studied for their structural and biological properties. Anti-/pro-oxidant properties were evaluated by using DPPH^• (2,2-diphenyl-1-picrylhydrazyl), ABTS^•+ (2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid), FRAP (ferric-reducing antioxidant power), CUPRAC (cupric-reducing antioxidant power), and Trolox oxidation assays. Lipophilicity was estimated by means of experimental (HPLC) and theoretical methods. The antimicrobial activity against Escherichia coli (E. coli), Pseudomonas aeruginosa (P. aeruginosa), Staphylococcus aureus (S. aureus), Bacillus subtilis (B. subtilis), Salmonella enteritidis (S. enteritidis), and Candida albicans (C. albicans) was studied. The cytotoxicity of HBAs in MCF-7 and MDA-MB-231 cell lines was estimated. Moreover, the structure of HBAs was studied by means of experimental (FTIR, ¹H, and ¹³C NMR) and quantum chemical DFT methods (the NBO and CHelpG charges, electrostatic potential maps, and electronic parameters based on the energy of HOMO and LUMO orbitals). The aromaticity of HBA was studied based on the calculated geometric and magnetic aromaticity indices (HOMA, Aj, BAC, I6, NICS). The biological activity of hydroxybenzoic acids was discussed in relation to their geometry, the electronic charge distribution in their molecules, their lipophilicity, and their acidity. Principal component analysis (PCA) was used in the statistical analysis of the obtained data and the discussion of the dependency between the structure and activity (SAR: structure–activity relationship) of HBAs. This work provides valuable information on the potential application of hydroxybenzoic acids as bioactive components in dietary supplements, functional foods, or even drugs.

In many countries, apple pomace (AP) is one of the most produced types of agri-food waste (globally, it is produced at a rate of ~4 million tons/year). If not managed properly, such bio-organic waste can cause serious pollution of the natural environment and public health hazards, mainly due to the risk of microbial contamination. This review shows that AP can be successfully reused in different industrial sectors—for example, as a source of energy and bio-materials—according to the idea of sustainable development. The recovered active compounds from AP can be applied as preservatives, antioxidants, anti-corrosion agents, wood protectors or biopolymers. Raw or processed forms of AP can also be considered as feedstocks for various bioenergy applications such as the production of intermediate bioenergy carriers (e.g., biogas and pyrolysis oil), and materials (e.g., biochar and activated carbon). In the future, AP and its active ingredients can be of great use due to their non-toxicity, biodegradability and biocompatibility. Given the increasing mass of produced AP, the commercial applications of AP could have a huge economic impact in the future.

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.

Nitrosyl complexes of iron are formed in living species in the presence of nitric oxide. They are considered a form in which NO can be stored and stabilized within a living cell. Upon entering a topic in bioinorganic chemistry the researcher faces a wide spectrum of issues concerning synthetic methods, the structure and chemical properties of the complex on the one hand, and its biological implications on the other. The aim of this review is to present the newest knowledge on nitrosyl iron complexes, summarizing the issues that are important for understanding the nature of nitrosyl iron complexes, their possible interactions, behavior in vitro and in vivo, handling of the preparations etc. in response to the growing interest in these compounds. Herein we focus mostly on the dinitrosyl iron complexes (DNICs) due to their prevailing occurrence in NO-treated biological samples. This article reviews recent knowledge on the structure, chemical properties and biological action of DNICs and some mononitrosyls of heme proteins. Synthetic methods are also briefly reviewed.