Plant-Derived and Dietary Hydroxybenzoic Acids—A Comprehensive Study of Structural, Anti-/Pro-Oxidant, Lipophilic, Antimicrobial, and Cytotoxic Activity in MDA-MB-231 and MCF-7 Cell Lines

Nutrients

卷:13

Renata Świsłocka¹  Grzegorz Świderski¹  Mariola Samsonowicz¹  Ewelina Gołębiewska¹  Monika Kalinowska¹  Waldemar Priebe²  Adam Cudowski³  Anna Pietryczuk³  Aleksander Astel⁴  Anna Barbara Złowodzka⁵  Włodzimierz Lewandowski⁶  Sylwia Męczyńska-Wielgosz⁷  Hanna Lewandowska⁷ 

[1] Department of Chemistry, Biology and Biotechnology, Bialystok University of Technology, Wiejska 45E Street, 15-351 Bialystok, Poland;

[2] Department of Experimental Therapeutics, The University of Texas MD Anderson Cancer Center, 1901 East Rd., Houston, TX 77054, USA;

[3] Department of Water Ecology, Faculty of Biology, University of Bialystok, Ciolkowskiego 1J Street, 15-245 Bialystok, Poland;

[4] Environmental Chemistry Research Unit, Institute of Biology and Earth Sciences, Pomeranian University in Słupsk, Arciszewskiego 22a Street, 76-200 Słupsk, Poland;

[5] Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3 Street, 00-664 Warszawa, Poland;

[6] Institute of Agricultural and Food Biotechnology—State Research Institute, Rakowiecka 36 Street, 02-532 Warsaw, Poland;

[7] Institute of Nuclear Chemistry and Technology, 16 Dorodna Street, 03-195 Warsaw, Poland;

关键词: hydroxybenzoic acids;    antioxidant;    lipophilic;    antimicrobial;    MCF-7;    MDA-MB-231;   

DOI  :  10.3390/nu13093107

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown