Evaluation of the potential of alkylresorcinols as superoxide anion scavengers and sox-regulon modulators using nitroblue tetrazolium and bioluminescent cell-based assays
-
Irina V. Gryazeva
Abstract
The antioxidant activities of five alkylresorcinol (AR) homologs with alkyl chains of 1, 3, 5 6 and 12 carbon atoms were studied using molecular and cellular assays for superoxide anions (O2.-). The effect of ARs as superoxide anion scavengers was assessed using the photochemical reaction of spontaneous photo-reduced flavin re-oxidation. In this system, ARs reaction with O2.- produced dye derivatives, as C6- and C12-AR prevented the O2.--induced conversion of nitroblue tetrazolium into formazan in AR-containing mixtures. The influence of ARs on soxS gene expression and bacterial cell viability was studied with the luminescent Escherichia coli K12 MG1655 psoxS’::luxCDABE-AmpR strain, showing low basal light emission. This increased significantly during paraquatinduced oxidative stress as a consequence of the simultaneous transcription of soxS-gene and lux-gene fusion. ARs with alkyl chains containing 5-12 carbon atoms at concentrations of 0.1-1.0 μM weakly induced soxS-gene expression, whereas 1-10 mM repressed it. This respectively increased or decreased the bacterial cell resistance to O2.- -related oxidative stress. AR derivatives lost their protective activity from reactions with superoxide anions, which required increased soxS gene expression for cell viability. These results show the dual nature of ARs, which possess direct antioxidant properties and the ability to indirectly regulate the activity of cellular antioxidative defense mechanisms.
References
1. El-Bahr, S.M. Biochemistry of free radicals and oxidative stress. Sci. Int. 1 (2013) 111-117.Search in Google Scholar
2. Imlay, J.A. Cellular defenses against superoxide and hydrogen peroxide Annu. Rev. Biochem. 77 (2008) 755-776.Search in Google Scholar
3. Imlay, J.A. Pathways of oxidative damage. Annu. Rev. Microbiol. 57 (2003) 395-418.10.1146/annurev.micro.57.030502.090938Search in Google Scholar PubMed
4. Miller, A.F. Superoxide dismutases: ancient enzymes and new insights. FEBS Lett. 586 (2012) 585-595. DOI: 10.1016/j.febslet.2011.10.048.10.1016/j.febslet.2011.10.048Search in Google Scholar PubMed PubMed Central
5. Broering, E.P., Truong, P.T., Gale, E.M. and Harrop, T.C. Synthetic analogues of nickel superoxide dismutase: a new role for nickel in biology. Biochemistry 52 (2013) 4-18. DOI: 10.1021/bi3014533.10.1021/bi3014533Search in Google Scholar PubMed
6. Demple, B. Redox signaling and gene control in the Escherichia coli soxRS oxidative stress regulon - a review. Gene 179 (1996) 53-57.Search in Google Scholar
7. Touati, D. Sensing and protecting against superoxide stress in Escherichia coli - how many ways are there to trigger soxRS response? Redox Rep. 5 (2000) 287-293.Search in Google Scholar
8. Krapp, A.R., Humbert, M.V. and Carrillo, N. The soxRS response of Escherichia coli can be induced in the absence of oxidative stress and oxygen by modulation of NADPH content. Microbiology 157 (2011) 957-965. DOI: 10.1099/mic.0.039461-0.10.1099/mic.0.039461-0Search in Google Scholar PubMed
9. Benov, L. How superoxide radical damages the cell. Protoplasma 217 (2001) 33-36.Search in Google Scholar
10. Kodali, V.P. and Sen, R. Antioxidant and free radical scavenging activities of an exopolysaccharide from a probiotic bacterium. Biotechnol. J. 3 (2008) 245-251.Search in Google Scholar
11. Pereira, D.M., Valentao, P., Pereira, J.A. and Andrade, P.B. Phenolics: from chemistry to biology. Molecules 14 (2009) 2202-2211. DOI:10.3390/molecules14062202.10.3390/molecules14062202Search in Google Scholar
12. Cyboran, S., Oszmianski, J. and Kleszczynska, H. Interaction between plant polyphenols and the erythrocyte membrane. Cell. Mol. Biol. Lett. 17 (2012) 77-88. DOI: 10.2478/s11658-011-0038-410.2478/s11658-011-0038-4Search in Google Scholar PubMed PubMed Central
13. Kozubek, A. and Tyman, J.H.P. Resorcinolic lipids, the natural nonisoprenoic amphiphiles and their biological activity. Chem. Rev. 99 (1999) 1-26.Search in Google Scholar
14. Stasiuk, M. and Kozubek, A. Biological activity of phenolic lipids. Cell. Mol. Life Sci. 67 (2010) 841-860.Search in Google Scholar
15. Singh, U.S., Scannell, R.T., An, H., Carter, B.J. and Hecht, S.M. DNA cleavage by di- and trihydroxyalkylbenzenes. Characterization of products and the roles of O2, Cu (II), and alkali. J. Am. Chem. Soc. 118 (1995) 12691-12699.10.1021/ja00156a005Search in Google Scholar
16. Nienartowicz, B. and Kozubek, A. Antioxidant activity of cereal bran resorcinolic lipids. Pol. J. Food Nutr. Sci. 2 (1993) 51-60.Search in Google Scholar
17. Struski, D.G. and Kozubek, A. Cereal grain alk(en)ylresorcinols protect lipids against ferrous ions-induced peroxidation. Z. Naturforsch. 47 (1992) 41-46.Search in Google Scholar
18. Kamnev, A.A., Dykman, R.L., Kovacs, K., Pankratov, A.N., Tugarova, A.V., Homonnay, Z. and Kuzmann, E. Redox interactions between structurally different alkylresorcinols and iron(III) in aqueous media: frozen-solution 57Fe Mössbauer spectroscopic studies, redox kinetics and quantum chemical evaluation of the alkylresorcinol reactivities. Struct. Chem. 25 (2014) 649-657. DOI: 10.1007/s11224-013-0367-1.10.1007/s11224-013-0367-1Search in Google Scholar
19. Deszcz, L. and Kozubek, A. Inhibition of soybean lipoxygenases by resorcinolic lipids from cereal bran. Cell. Mol. Biol. Lett. 2 (1997) 213-222.Search in Google Scholar
20. Deryabin, D.G., Davydova, O.K., Gryazeva, I.V. and El’-Registan, G.I. Involvement of alkylhydroxybenzenes in the Escherichia coli response to the lethal effect of UV irradiation. Microbiologiya 81 (2012) 168-177.Search in Google Scholar
21. Miche, L., Belkin, S., Rozen, R. and Balandreau, J. Rice seedling whole exudates and extracted alkylresorcinols induce stress-response in Escherichia coli biosensors. Environ. Microbiol. 5 (2003) 403-411.Search in Google Scholar
22. Konanykhina, I.A., Shanenko, E.F., Loiko, N.G., Nikolaev, Yu.A. and El-Registan G.I. Regulatory effect of microbial alkyloxybenzenes of different structure on the stress response of yeast. Appl. Biochem. Microbiol. 44 (2008) 518-522.Search in Google Scholar
23. Stepanenko, I.Iu., Strakhovskaia, M.G., Belenikina, N.S., Nikolaev, Yu.A., Miliukin, A.L., Kozlova, A.N., Revina, A.A. and El-Registan, G.I. Protection of Saccharomyces cerevisiae against oxidative and radiationcaused damage by alkyl hydroxybenzenes. Mikrobiologiya 73 (2004) 204-210.Search in Google Scholar
24. Giannopolitis, G.N. and Ries, S.K. In vitro production of superoxide radical from paraquat and its interactions with monuron and diuron. Weed Sci. 25 (1977) 298-303. Search in Google Scholar
25. Lu, J.-M., Lin, P.H., Yao, Q. and Chen, C. Chemical and molecular mechanisms of antioxidants: experimental approaches and model systems. J. Cell. Mol. Med. 14 (2010) 840-860.10.1111/j.1582-4934.2009.00897.xSearch in Google Scholar PubMed PubMed Central
26. Kotova, V.Yu., Manukhov, I.V. and Zavilgelskii, G.B. Lux-biosensors for detection of SOS-response, heat shock, and oxidative stress. Appl. Biochem. Microbiol. 46 (2010) 781-788.10.1134/S0003683810080089Search in Google Scholar
27. Kubo, I., Masuoka, N., Ha, T.J. and Tsujimoto, K. Antioxidant activity of anacardic acids. Food Chem. 99 (2006) 555-562.Search in Google Scholar
28. Korycinska, M., Czelna, K., Jaromin, A. and Kozubek, A. Antioxidant activity of rye bran alkylresorcinols and extracts from whole-grain cereal products. Food Chem. 116 (2009) 1013-1018.Search in Google Scholar
29. Parikka, K., Rowland, I.R., Welch, R.W. and Wahala, K. In vitro antioxidant activity and antigenotoxicity of 5-n-alkylresorcinols. J. Agric. Food Chem. 54 (2006) 1646-1650.Search in Google Scholar
30. Hladyszowski, J., Zubik, L. and Kozubek, A. Quantum mechanical and experimental oxidation studies of pentadecylresorcinol, olovetol, orcinol and resorcinol. Free Radical Res. 28 (1998) 359-368.10.3109/10715769809070804Search in Google Scholar PubMed
31. Trevisan, M.T.S., Pfundstein, B., Haubner, R., Wurtele, G., Spiegelhalder, B., Bartsch, H. and Owen, R.W. Characterization of alkylphenols in cashew (Anacardium occcidentale) products and assay of their antioxidant capacity. Food Chem. Toxicol. 44 (2006) 188-197.Search in Google Scholar
32. Rodrigues, F.H.A., Feitosa, J.P.A., Ricardo, N.M.P., de Franca, F.C.F. and Carioca, J.O.B. Antioxidant activity of cashew shell nut liquid (CNSL) derivatives on the thermal oxidation of synthetic cis-1, 4-polyisoprene. J. Braz. Chem. Soc. 17 (2006) 265-271. 10.1590/S0103-50532006000200008Search in Google Scholar
© 2015 University of Wrocław, Poland
Articles in the same Issue
- Identification of drought-induced transcription factors in Sorghum bicolor using GO term semantic similarity
- Evaluation of the potential of alkylresorcinols as superoxide anion scavengers and sox-regulon modulators using nitroblue tetrazolium and bioluminescent cell-based assays
- Cyclic phosphatidic acid induces G0/G1 arrest, inhibits AKT phosphorylation, and downregulates cyclin D1 expression in colorectal cancer cells
- Polymorphism of the APEX nuclease 1 gene in keratoconus and Fuchs endothelial corneal dystrophy
- FE65: Roles beyond amyloid precursor protein processing
- Single nucleotide polymorphisms in the STAT3 gene influence AITD susceptibility, thyroid autoantibody levels, and IL6 and IL17 secretion
- Antioxidant effect of a fermented powder of Lady Joy bean in primary rat hepatocytes
- Oncogene-dependent survival of highly transformed cancer cells under conditions of extreme centrifugal force – implications for studies on extracellular vesicles
- Changes in cell death of peripheral blood lymphocytes isolated from children with acute lymphoblastic leukemia upon stimulation with 7 Hz, 30 mT pulsed electromagnetic field
- Flow cytometric analysis of apoptosis in cryoconserved chicken primordial germ cells
- GGeneration of an efficient artificial promoter of bovine skeletal muscle alpha-actin gene (ACTA1) through addition of cis-acting element
Articles in the same Issue
- Identification of drought-induced transcription factors in Sorghum bicolor using GO term semantic similarity
- Evaluation of the potential of alkylresorcinols as superoxide anion scavengers and sox-regulon modulators using nitroblue tetrazolium and bioluminescent cell-based assays
- Cyclic phosphatidic acid induces G0/G1 arrest, inhibits AKT phosphorylation, and downregulates cyclin D1 expression in colorectal cancer cells
- Polymorphism of the APEX nuclease 1 gene in keratoconus and Fuchs endothelial corneal dystrophy
- FE65: Roles beyond amyloid precursor protein processing
- Single nucleotide polymorphisms in the STAT3 gene influence AITD susceptibility, thyroid autoantibody levels, and IL6 and IL17 secretion
- Antioxidant effect of a fermented powder of Lady Joy bean in primary rat hepatocytes
- Oncogene-dependent survival of highly transformed cancer cells under conditions of extreme centrifugal force – implications for studies on extracellular vesicles
- Changes in cell death of peripheral blood lymphocytes isolated from children with acute lymphoblastic leukemia upon stimulation with 7 Hz, 30 mT pulsed electromagnetic field
- Flow cytometric analysis of apoptosis in cryoconserved chicken primordial germ cells
- GGeneration of an efficient artificial promoter of bovine skeletal muscle alpha-actin gene (ACTA1) through addition of cis-acting element
