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

被引:79
作者
Godlewska-Zylkiewicz, Beata [1 ]
Swislocka, Renata [2 ]
Kalinowska, Monika [2 ]
Golonko, Aleksandra [3 ]
Swiderski, Grzegorz [2 ]
Arciszewska, Zaneta [1 ]
Nalewajko-Sieliwoniuk, Edyta [1 ]
Naumowicz, Monika [4 ]
Lewandowski, Wlodzimierz [2 ]
机构
[1] Univ Bialystok, Dept Analyt Chem, Fac Chem, K Ciolkowskiego 1K, PL-15245 Bialystok, Poland
[2] Bialystok Tech Univ, Dept Chem Biol & Biotechnol, Wiejska 45E, PL-15351 Bialystok, Poland
[3] Inst Agr & Food Biotechnol, Rakowiecka 36, PL-02532 Warsaw, Poland
[4] Univ Bialystok, Dept Phys Chem, Fac Chem, K Ciolkowskiego 1K, PL-15245 Bialystok, Poland
关键词
phenolic acids; natural carboxylic acids; structure-activity relationship; hydroxyl groups; antibacterial; antioxidant; cytotoxic activity; RADICAL-SCAVENGING ACTIVITY; P-COUMARIC ACID; CAFFEIC ACID; ROSMARINIC ACID; PHENOLIC-COMPOUNDS; ANTIBACTERIAL ACTIVITY; OXIDATIVE STRESS; CHICORIC ACID; CHLOROGENIC ACID; ESSENTIAL OIL;
D O I
10.3390/ma13194454
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
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 similar to 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.
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页码:1 / 37
页数:37
相关论文
共 221 条
[11]   Fine-tuning of the hydrophobicity of caffeic acid: studies on the antimicrobial activity against Staphylococcus aureus and Escherichia coli [J].
Andrade, Mafalda ;
Benfeito, Sofia ;
Soares, Pedro ;
Magalhaes e Silva, Diogo ;
Loureiro, Joana ;
Borges, Anabela ;
Borges, Fernanda ;
Simoes, Manuel .
RSC ADVANCES, 2015, 5 (66) :53915-53925
[12]   Rosmarinic Acid Exhibits Anticancer Effects via MARK4 Inhibition [J].
Anwar, Saleha ;
Shamsi, Anas ;
Shahbaaz, Mohd ;
Queen, Aarfa ;
Khan, Parvez ;
Hasan, Gulam Mustafa ;
Islam, Asimul ;
Alajmi, Mohamed F. ;
Hussain, Afzal ;
Ahmad, Faizan ;
Hassan, Md Imtaiyaz .
SCIENTIFIC REPORTS, 2020, 10 (01)
[13]   Novel total antioxidant capacity index for dietary polyphenols and vitamins C and E, using their cupric ion reducing capability in the presence of neocuproine:: CUPRAC method [J].
Apak, R ;
Güçlu, K ;
Özyürek, M ;
Karademir, SE .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2004, 52 (26) :7970-7981
[14]   Absorption of chlorogenic acid and caffeic acid in rats after oral administration [J].
Azuma, K ;
Ippoushi, K ;
Nakayama, M ;
Ito, H ;
Higashio, H ;
Terao, J .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2000, 48 (11) :5496-5500
[15]   Does rosmarinic acid treatment have protective role against sepsis-induced oxidative damage in Wistar Albino rats? [J].
Bacanli, M. ;
Aydin, S. ;
Taner, G. ;
Goktas, H. G. ;
Sahin, T. ;
Basaran, A. A. ;
Basaran, N. .
HUMAN & EXPERIMENTAL TOXICOLOGY, 2016, 35 (08) :877-886
[16]   Antiproliferative and apoptotic effects of the oxidative dimerization product of methyl caffeate on human breast cancer cells [J].
Bailly, Fabrice ;
Toillon, Robert-Alain ;
Tomavo, Olympe ;
Jouy, Nathalie ;
Hondermarck, Hubert ;
Cotelle, Philippe .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (02) :574-578
[17]   LETHAL EFFECT OF METHYL AND PROPYL PARABENS AS RELATED TO STAPHYLOCOCCUS-AUREUS LIPID-COMPOSITION [J].
BARGIOTA, E ;
RICOMUNOZ, E ;
DAVIDSON, PM .
INTERNATIONAL JOURNAL OF FOOD MICROBIOLOGY, 1987, 4 (03) :257-266
[18]  
Barton D., 1979, COMPREHENSIVE ORGANI, V1st
[19]   Adsorption of Natural 3-Phenylpropenic Acids on Cerium Dioxide Surface [J].
Barvinchenko, V. N. ;
Lipkovskaya, N. A. ;
Kulik, T. V. ;
Kartel', N. T. .
COLLOID JOURNAL, 2019, 81 (01) :1-7
[20]   Thermodynamic and Mechanistic Study of the Electrochemical Oxidation of Rosmarinic Acid [J].
Beiginejad, Hadi ;
Moradi, Mohammad ;
Paziresh, Shadi ;
Farahani, Hadis .
JOURNAL OF THE ELECTROCHEMICAL SOCIETY, 2018, 165 (11) :11698-11704