ISSN 2146-8389
 

Original Research (Original Article) 


Kinetic measurements of peroxynitrite scavenging properties of hydroxybenzoates

Beata Velika, Beata Hubkova, Juraj Guzy.

Abstract
Objective: Hydroxybenzoic acids and their derivatives belongs to phenols, which are characterized by salubrious properties, leading to a reduction of the incidence of chronic diseases. The most significant health related features of hydroxybenzoic acids and their derivatives are their antioxidant properties. Peroxynitrite is a reactive nitrogen compound which can cause lipid peroxidation with subsequent cellular damage. The aim of the present work was to determine the peroxynitrite scavenging property of different hydroxybenzoates, with regard to their chemical structure.
Methods: In our study, we tested 14 hydroxybenzoic acids and a number of their derivatives in the reaction with peroxynitrite. The compounds were selected to have different number and different position of the hydroxyl group(s) attached to the benzene ring. In this way we ensured the study of different suitable model compounds by testing their antioxidant properties. The peroxynitrite scavenging properties of the model compounds were studied using kinetic spectrophotometric measurements. The reaction rate was calculated based on the decrease in peroxynitrite concentration.
Results: The most significant peroxynitrite scavenging properties based on the reaction rate were detected in compounds with hydroxyl groups substituted in the positions meta and para: 3,4-dihydroxybenzoic acid, gallic acid and caffeic acid. Also, increased reaction rates were recorded in the reaction of 2,4-dihydroxybenzoic acid, acetylsalicylic acid and 2-hydroxybenzoic acid with peroxynitrite.
Conclusion: Our results confirmed the thesis that the free radical scavenging properties are dependent on the position and the number of the hydroxyl group(s) in relation to the carboxylic functional group attached to the benzene ring. Better understanding of the relations between the structure and the action of these antioxidants may be helpful in their proper utilization during prevention and treatment of diseases.

Key words: Hydroxybenzoic acid, hydroxyl group, peroxynitrite, spectrophotometry


 
ARTICLE TOOLS
Abstract
PDF Fulltext
Print this article Print this Article
How to cite this articleHow to cite this article
Export to
Export to
Related Records
 Articles by Beata Velika
Articles by Beata Hubkova
Articles by Juraj Guzy
on Google
on Google Scholar
Article Statistics
 Viewed: 573
Downloaded: 157
Cited: 0

REFERENCES
1. Shahidi F, Janitha PK, Wanasundara PD. Phenolic antioxidants. Crit Rev Food Sci Nutr 1992; 32:67-103. [DOI via Crossref]    [Pubmed]   
2. Martin C, Zhang Y, Tonelli C, Petroni K. Plants, diet, and health. Annu Rev Plant Biol 2013; 64:19-46. [DOI via Crossref]    [Pubmed]   
3. Shahidi F, Ambigaipalan P. Phenolic compounds in foods, beverages and spices: antioxidant activity and health effects – a review. J Funct Foods 2015; 18: 820-97. [DOI via Crossref]   
4. Bilecova-Rabajdova M, Birkova A, Urban P, Gregova K, Durovcova E. Naturally occurring substances and their role in chemo-protective effects. Centr Eur J Public Health 2013; 21:213-9.
5. Velika B, Kron I. Antioxidant properties of phenols against superoxide radical. Chemical Monthly 2013; 144:1287-90. [DOI via Crossref]   
6. Szaba C, Ischiropoulos H, Radi R. Peroxynitrite: biochemistry, pathophysiology and development of therapeutics. Nat Rev Drug Discov 2007; 6:662-80. [DOI via Crossref]    [Pubmed]   
7. Pacher P, Beckman JS, Liaudet L. Nitric oxide and peroxynitrite in health and disease. Physiol Rev 2007; 87:315-424. [DOI via Crossref]    [Pubmed]    [PMC Free Fulltext]   
8. Bredt DS, Snyder SH. Nitric oxide, a novel neuronal messenger. Neuron 1992; 8:3-11. [DOI via Crossref]   
9. Prolo C, Alvarez MN, Radi R. Peroxynitrite, a potent macrophagederived oxidizing cytotoxin to combat invading pathogens. Biofactors 2014; 40:215-25. [DOI via Crossref]    [Pubmed]    [PMC Free Fulltext]   
10. Beckman JS, Koppenol WH. Nitric oxide, superoxide, and peroxynitrite: the good, the bad, and the ugly. Am J Physiol 1996; 271:C1424-37.
11. Beckman JS, Chen J, Ischiropoulos H, Crow JP. Oxidative chemistry of peroxynitrite. Methods Enzymol 1994; 223:229-40. [DOI via Crossref]   
12. Martin C, Zhang Y, Tonelli C, Petroni K. Plants, diet, and health. Ann Rev Plant Biol 2013; 64:19-46. [DOI via Crossref]    [Pubmed]   
13. Chen X, Chen H, Xu M, Shen J. Targeting reactive nitrogen species: a promising therapeutic strategy for cerebral ischemia-reperfusion injury. Acta Pharmacol Sin 2013; 34:67-77. [DOI via Crossref]    [Pubmed]    [PMC Free Fulltext]   
14. Heijnen CG, Haenen GR, van Acker FA, van der Vijgh WJ, Bast A. Flavonoids as peroxynitrite scavengers: the role of the hydroxyl groups. Toxicol in Vitro 2001; 15:3-6. [DOI via Crossref]   
15. Hubkova B, Velika B, Birkova A, Guzy J, Marekova M. Hydroxybenzoic acids and their derivatives as peroxynitrite scavengers. Free Radic Biol Med 2014; 75:S33-4.
16. Scientific Opinion on the substantiation of health claims related to various food(s)/food constituent(s) and protection of cells from premature aging, antioxidant activity, antioxidant content and antioxidant properties, and protection of DNA, proteins and lipids from oxidative damage pursuant to Article 13(1) of Regulation (EC) No 1924/2006. EFSA Journal 2010; 8:1489. [DOI via Crossref]   

How to Cite this Article
Pubmed Style

Velika B, Hubkova B, Guzy J. Kinetic measurements of peroxynitrite scavenging properties of hydroxybenzoates. Oxid Antioxid Med Sci. 2016; 5(1): 28-32. doi:10.5455/oams.230316.or.094


Web Style

Velika B, Hubkova B, Guzy J. Kinetic measurements of peroxynitrite scavenging properties of hydroxybenzoates. http://www.ejmoams.com/?mno=216648 [Access: May 22, 2018]. doi:10.5455/oams.230316.or.094


AMA (American Medical Association) Style

Velika B, Hubkova B, Guzy J. Kinetic measurements of peroxynitrite scavenging properties of hydroxybenzoates. Oxid Antioxid Med Sci. 2016; 5(1): 28-32. doi:10.5455/oams.230316.or.094



Vancouver/ICMJE Style

Velika B, Hubkova B, Guzy J. Kinetic measurements of peroxynitrite scavenging properties of hydroxybenzoates. Oxid Antioxid Med Sci. (2016), [cited May 22, 2018]; 5(1): 28-32. doi:10.5455/oams.230316.or.094



Harvard Style

Velika, B., Hubkova, B. & Guzy, J. (2016) Kinetic measurements of peroxynitrite scavenging properties of hydroxybenzoates. Oxid Antioxid Med Sci, 5 (1), 28-32. doi:10.5455/oams.230316.or.094



Turabian Style

Velika, Beata, Beata Hubkova, and Juraj Guzy. 2016. Kinetic measurements of peroxynitrite scavenging properties of hydroxybenzoates. Oxidants and Antioxidants in Medical Science, 5 (1), 28-32. doi:10.5455/oams.230316.or.094



Chicago Style

Velika, Beata, Beata Hubkova, and Juraj Guzy. "Kinetic measurements of peroxynitrite scavenging properties of hydroxybenzoates." Oxidants and Antioxidants in Medical Science 5 (2016), 28-32. doi:10.5455/oams.230316.or.094



MLA (The Modern Language Association) Style

Velika, Beata, Beata Hubkova, and Juraj Guzy. "Kinetic measurements of peroxynitrite scavenging properties of hydroxybenzoates." Oxidants and Antioxidants in Medical Science 5.1 (2016), 28-32. Print. doi:10.5455/oams.230316.or.094



APA (American Psychological Association) Style

Velika, B., Hubkova, B. & Guzy, J. (2016) Kinetic measurements of peroxynitrite scavenging properties of hydroxybenzoates. Oxidants and Antioxidants in Medical Science, 5 (1), 28-32. doi:10.5455/oams.230316.or.094





Most Viewed Articles
  • Low intensity radiofrequency radiation: a new oxidant for living cells
    Igor Yakymenko, Evgeniy Sidorik, Diane Henshel, Sergiy Kyrylenko
    Oxid Antioxid Med Sci. 2014; 3(1): 1-3
    » Abstract & References » doi: 10.5455/oams.240314.ed.002

  • Oxidants and antioxidants: friends or foes?
    Sukru Oter, Si Jin, Luca Cucullo, H.J. Damien Dorman
    Oxid Antioxid Med Sci. 2012; 1(1): 1-4
    » Abstract & References » doi: 10.5455/oams.080612.ed.001

  • Effects of free radicals and antioxidants on exercise performance
    Sikiru Lamina, Charles I. Ezema, Anele I. Theresa, Ezugwu U. Anthonia
    Oxid Antioxid Med Sci. 2013; 2(2): 83-91
    » Abstract & References » doi: 10.5455/oams.010413.rv.005

  • Effects of silymarin, N-acetylcysteine and selenium in the treatment of papulopustular acne
    Haidar Hamid Al-Anbari, Ahmed Salih Sahib, Ahmed R. Abu Raghif
    Oxid Antioxid Med Sci. 2012; 1(3): 201-207
    » Abstract & References » doi: 10.5455/oams.290912.or.019

  • Anticancer and free radical scavenging potency of Catharanthus roseus, Dendrophthoe petandra, Piper betle and Curcuma mangga extracts in breast cancer cell lines
    Wahyu Widowati, Tjandrawati Mozef, Chandra Risdian, Yellianty Yellianty
    Oxid Antioxid Med Sci. 2013; 2(2): 137-142
    » Abstract & References » doi: 10.5455/oams.100413.or.038

  • Antimicrobial and antioxidant properties of marine actinomycetes Streptomyces sp VITSTK7
    Mohankumar Thenmozhi, Krishnan Kannabiran
    Oxid Antioxid Med Sci. 2012; 1(1): 51-57
    » Abstract & References » doi: 10.5455/oams.270412.or.005

  • Is it oxidative or free radical stress and why does it matter?
    Boguslaw Lipinski
    Oxid Antioxid Med Sci. 2012; 1(1): 5-9
    » Abstract & References » doi: 10.5455/oams.130312.rv.001

  • Chemical properties of Monodora myristica and its protective potentials against free radicals in vitro
    Ochuko L. Erukainure, Oluwatoyin V. Oke, Folashade O. Owolabi, Funmi O. Kayode, Emmanuel E. Umanhonlen, Muhammad Aliyu
    Oxid Antioxid Med Sci. 2012; 1(2): 127-132
    » Abstract & References » doi: 10.5455/oams.080712.or.009

  • Cytotoxic and proapoptotic activities of gallic acid to human oral cancer HSC-2 cells
    Alyssa G. Schuck, Jeffrey H. Weisburg, Hannah Esan, Esther F. Robin, Ayelet R. Bersson, Jordana R. Weitschner, Tova Lahasky, Harriet L. Zuckerbraun, Harvey Babich
    Oxid Antioxid Med Sci. 2013; 2(4): 265-274
    » Abstract & References » doi: 10.5455/oams.220713.or.051

  • Phytochemical and in vitro antioxidant properties of the methanolic extract of fruits of Blighia sapida, Vitellaria paradoxa and Vitex doniana
    Rabiat U. Hamzah, Evans C. Egwim, Adamu Y. Kabiru, Mary B. Muazu
    Oxid Antioxid Med Sci. 2013; 2(3): 217-223
    » Abstract & References » doi: 10.5455/oams.090513.or.043

  • Most Downloaded
  • Low intensity radiofrequency radiation: a new oxidant for living cells
    Igor Yakymenko, Evgeniy Sidorik, Diane Henshel, Sergiy Kyrylenko
    Oxid Antioxid Med Sci. 2014; 3(1): 1-3
    » Abstract & References » doi: 10.5455/oams.240314.ed.002

  • Oxidants and antioxidants: friends or foes?
    Sukru Oter, Si Jin, Luca Cucullo, H.J. Damien Dorman
    Oxid Antioxid Med Sci. 2012; 1(1): 1-4
    » Abstract & References » doi: 10.5455/oams.080612.ed.001

  • The antioxidant capacity and immunomodulatory activity of stingless bee honeys proceeding from Costa Rica
    Gabriel Zamora, Kees Beukelman, Bert van den Berg, Maria Laura Arias, Eduardo Umana, Ingrid Aguilar, Linda Quarles van Ufford, Edwin van den Worm, Natalia Fallas, Rebeca Solorzano
    Oxid Antioxid Med Sci. 2015; 4(1): 49-55
    » Abstract & References » doi: 10.5455/oams.180415.or.084

  • Is it oxidative or free radical stress and why does it matter?
    Boguslaw Lipinski
    Oxid Antioxid Med Sci. 2012; 1(1): 5-9
    » Abstract & References » doi: 10.5455/oams.130312.rv.001

  • Antimicrobial and antioxidant properties of marine actinomycetes Streptomyces sp VITSTK7
    Mohankumar Thenmozhi, Krishnan Kannabiran
    Oxid Antioxid Med Sci. 2012; 1(1): 51-57
    » Abstract & References » doi: 10.5455/oams.270412.or.005

  • Anticancer and free radical scavenging potency of Catharanthus roseus, Dendrophthoe petandra, Piper betle and Curcuma mangga extracts in breast cancer cell lines
    Wahyu Widowati, Tjandrawati Mozef, Chandra Risdian, Yellianty Yellianty
    Oxid Antioxid Med Sci. 2013; 2(2): 137-142
    » Abstract & References » doi: 10.5455/oams.100413.or.038

  • Effects of free radicals and antioxidants on exercise performance
    Sikiru Lamina, Charles I. Ezema, Anele I. Theresa, Ezugwu U. Anthonia
    Oxid Antioxid Med Sci. 2013; 2(2): 83-91
    » Abstract & References » doi: 10.5455/oams.010413.rv.005

  • Protective properties of complex of quercetin, selenium, catechins and curcumin against DNA damage
    Jana Kadrabova, Marica Krajcovicova-Kudlackova, Alexander Madaric, Martina Valachovicova, Csilla Mislanova, Maria Korenovska
    Oxid Antioxid Med Sci. 2012; 1(3): 179-184
    » Abstract & References » doi: 10.5455/oams.180912.or.018

  • Airway antioxidant capacity and pH in chronic obstructive pulmonary disease
    Wei Lee, Hsien Loo, Paul S. Thomas
    Oxid Antioxid Med Sci. 2012; 1(3): 153-160
    » Abstract & References » doi: 10.5455/oams.300812.or.016

  • Heparin or EDTA; anticoagulant of choice in free radical estimation?
    Kuldeep Mohanty, Swetasmita Mishra, Jhumur Pani, Tarannum Hasan, Abhishek Purohit, Subhadra Sharma, Rima Dada
    Oxid Antioxid Med Sci. 2012; 1(1): 21-24
    » Abstract & References » doi: 10.5455/oams.130512.br.001

  • Most Cited Articles
  • Chemical properties of Monodora myristica and its protective potentials against free radicals in vitro
    Ochuko L. Erukainure, Oluwatoyin V. Oke, Folashade O. Owolabi, Funmi O. Kayode, Emmanuel E. Umanhonlen, Muhammad Aliyu
    Oxid Antioxid Med Sci. 2012; 1(2): 127-132
    » Abstract & References » doi: 10.5455/oams.080712.or.009
    Cited : 12 times [Click to see citing articles]

  • Role of free radicals and antioxidants in gynecological cancers: current status and future prospects
    Lokanatha Valluru, Subramanyam Dasari, Rajendra Wudayagiri
    Oxid Antioxid Med Sci. 2014; 3(1): 15-26
    » Abstract & References » doi: 10.5455/oams.201113.rv.011
    Cited : 10 times [Click to see citing articles]

  • Anticancer and free radical scavenging potency of Catharanthus roseus, Dendrophthoe petandra, Piper betle and Curcuma mangga extracts in breast cancer cell lines
    Wahyu Widowati, Tjandrawati Mozef, Chandra Risdian, Yellianty Yellianty
    Oxid Antioxid Med Sci. 2013; 2(2): 137-142
    » Abstract & References » doi: 10.5455/oams.100413.or.038
    Cited : 10 times [Click to see citing articles]

  • Silymarin and naringenin protects nicotine induced oxidative stress in young rats
    Anshu Jain, Nidhi Dwivedi, Rakesh Bhargava, Swaran J.S. Flora
    Oxid Antioxid Med Sci. 2012; 1(1): 41-49
    » Abstract & References » doi: 10.5455/oams.130412.or.004
    Cited : 9 times [Click to see citing articles]

  • Palm vitamin E reduces oxidative stress, and physical and morphological alterations of erythrocyte membranes in streptozotocin-induced diabetic rats
    Fatmah Ali Matough, Siti Balkis Budin, Zariyantey Abdul Hamid, Santhana Raj Louis, Nasar Alwahaibi, Jamaludin Mohamed
    Oxid Antioxid Med Sci. 2012; 1(1): 59-68
    » Abstract & References » doi: 10.5455/oams.300412.or.006
    Cited : 8 times [Click to see citing articles]

  • Peroxidative index as novel marker of hydrogen peroxide involvement in lipid peroxidation from coal dust exposure
    Nia Kania, Bambang Setiawan, Edi Widjajanto, Nurdiana Nurdiana, M. Aris Widodo, H.M.S. Chandra Kusuma
    Oxid Antioxid Med Sci. 2012; 1(3): 209-215
    » Abstract & References » doi: 10.5455/oams.031012.or.020
    Cited : 8 times [Click to see citing articles]

  • Phytochemical and in vitro antioxidant properties of the methanolic extract of fruits of Blighia sapida, Vitellaria paradoxa and Vitex doniana
    Rabiat U. Hamzah, Evans C. Egwim, Adamu Y. Kabiru, Mary B. Muazu
    Oxid Antioxid Med Sci. 2013; 2(3): 217-223
    » Abstract & References » doi: 10.5455/oams.090513.or.043
    Cited : 8 times [Click to see citing articles]

  • Heparin or EDTA; anticoagulant of choice in free radical estimation?
    Kuldeep Mohanty, Swetasmita Mishra, Jhumur Pani, Tarannum Hasan, Abhishek Purohit, Subhadra Sharma, Rima Dada
    Oxid Antioxid Med Sci. 2012; 1(1): 21-24
    » Abstract & References » doi: 10.5455/oams.130512.br.001
    Cited : 6 times [Click to see citing articles]

  • Antimicrobial and antioxidant properties of marine actinomycetes Streptomyces sp VITSTK7
    Mohankumar Thenmozhi, Krishnan Kannabiran
    Oxid Antioxid Med Sci. 2012; 1(1): 51-57
    » Abstract & References » doi: 10.5455/oams.270412.or.005
    Cited : 6 times [Click to see citing articles]

  • Cytotoxic and proapoptotic activities of gallic acid to human oral cancer HSC-2 cells
    Alyssa G. Schuck, Jeffrey H. Weisburg, Hannah Esan, Esther F. Robin, Ayelet R. Bersson, Jordana R. Weitschner, Tova Lahasky, Harriet L. Zuckerbraun, Harvey Babich
    Oxid Antioxid Med Sci. 2013; 2(4): 265-274
    » Abstract & References » doi: 10.5455/oams.220713.or.051
    Cited : 6 times [Click to see citing articles]