Research Article
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Year 2022, Volume: 9 Issue: 1, 29 - 36, 28.02.2022
https://doi.org/10.18596/jotcsa.952065

Abstract

References

  • 1. Ls R, Nja S. Anticancer Properties of Phenolic Acids in Colon Cancer – A Review. J Nutr Food Sci [Internet]. 2016 [cited 2021 Nov 29];06(02).
  • 2. Weng C-J, Yen G-C. Chemopreventive effects of dietary phytochemicals against cancer invasion and metastasis: Phenolic acids, monophenol, polyphenol, and their derivatives. Cancer Treatment Reviews. 2012 Feb;38(1):76–87.
  • 3. Tian R-R, Pan Q-H, Zhan J-C, Li J-M, Wan S-B, Zhang Q-H, et al. Comparison of Phenolic Acids and Flavan-3-ols During Wine Fermentation of Grapes with Different Harvest Times. Molecules. 2009 Feb 18;14(2):827–38.
  • 4. Badhani B, Sharma N, Kakkar R. Gallic acid: a versatile antioxidant with promising therapeutic and industrial applications. RSC Adv. 2015;5(35):27540–57.
  • 5. Sagdicoglu Celep AG, Demirkaya A, Solak EK. Antioxidant and anticancer activities of gallic acid loaded sodium alginate microspheres on colon cancer. Current Applied Physics. 2020 Jul;S1567173920301164.
  • 6. de Cristo Soares Alves A, Mainardes RM, Khalil NM. Nanoencapsulation of gallic acid and evaluation of its cytotoxicity and antioxidant activity. Materials Science and Engineering: C. 2016 Mar;60:126–34.
  • 7. Giardina P, Faraco V, Pezzella C, Piscitelli A, Vanhulle S, Sannia G. Laccases: a never-ending story. Cell Mol Life Sci. 2010 Feb;67(3):369–85.
  • 8. Su J, Noro J, Fu J, Wang Q, Silva C, Cavaco-Paulo A. Enzymatic polymerization of catechol under high-pressure homogenization for the green coloration of textiles. Journal of Cleaner Production. 2018 Nov;202:792–8.
  • 9. Su J, Castro TG, Noro J, Fu J, Wang Q, Silva C, et al. The effect of high-energy environments on the structure of laccase-polymerized poly(catechol). Ultrasonics Sonochemistry. 2018 Nov;48:275–80.
  • 10. Jiang Z, Yuan X, Yao K, Li X, Zhang X, Mu Z, et al. Laccase-aided modification: Effects on structure, gel properties and antioxidant activities of α-lactalbumin. LWT. 2017 Jul;80:355–63.
  • 11. Aljawish A, Chevalot I, Jasniewski J, Paris C, Scher J, Muniglia L. Laccase-catalysed oxidation of ferulic acid and ethyl ferulate in aqueous medium: A green procedure for the synthesis of new compounds. Food Chemistry. 2014 Feb;145:1046–54.
  • 12. Mattinen M-L, Hellman M, Permi P, Autio K, Kalkkinen N, Buchert J. Effect of Protein Structure on Laccase-Catalyzed Protein Oligomerization. J Agric Food Chem. 2006 Nov 1;54(23):8883–90.
  • 13. Livney YD. Milk proteins as vehicles for bioactives. Current Opinion in Colloid & Interface Science. 2010 Apr;15(1–2):73–83.
  • 14. Matsudomi N, Rector D, Kinsella JE. Gelation of bovine serum albumin and β-lactoglobulin; effects of pH, salts and thiol reagents. Food Chemistry. 1991 Jan;40(1):55–69.
  • 15. Božič M, Gorgieva S, Kokol V. Laccase-mediated functionalization of chitosan by caffeic and gallic acids for modulating antioxidant and antimicrobial properties. Carbohydrate Polymers. 2012 Mar;87(4):2388–98.
  • 16. Yu C, Liu X, Pei J, Wang Y. Grafting of laccase-catalysed oxidation of butyl paraben and p-coumaric acid onto chitosan to improve its antioxidant and antibacterial activities. Reactive and Functional Polymers. 2020 Apr;149:104511.
  • 17. Božič M, Štrancar J, Kokol V. Laccase-initiated reaction between phenolic acids and chitosan. Reactive and Functional Polymers. 2013 Oct;73(10):1377–83.
  • 18. Wolfenden BS, Willson RobinL. Radical-cations as reference chromogens in kinetic studies of ono-electron transfer reactions: pulse radiolysis studies of 2,2′-azinobis-(3-ethylbenzthiazoline-6-sulphonate). J Chem Soc, Perkin Trans 2. 1982;(7):805–12.
  • 19. Kim S, Cavaco-Paulo A. Laccase-catalysed protein–flavonoid conjugates for flax fibre modification. Appl Microbiol Biotechnol. 2012 Jan;93(2):585–600.
  • 20. Brand-Williams W, Cuvelier ME, Berset C. Use of a free radical method to evaluate antioxidant activity. LWT - Food Science and Technology. 1995;28(1):25–30.
  • 21. Arnao MB, Cano A, Alcolea JF, Acosta M. Estimation of free radical-quenching activity of leaf pigment extracts. Phytochem Anal. 2001 Mar;12(2):138–43.
  • 22. Grigoryan KR, Shilajyan HA. Analysis of the interaction of gallic acid and myoglobin by UV-vis absorption spectroscopy. Russ J Bioorg Chem. 2017 May;43(3):255–8.
  • 23. Grdadolnik J. Saturation effects in FTIR spectroscopy: intensity of amide I and amide II bands in protein spectra. Acta chimica slovenica. 2003;50(4):777–88.
  • 24. Fan Y, Liu Y, Gao L, Zhang Y, Yi J. Improved chemical stability and cellular antioxidant activity of resveratrol in zein nanoparticle with bovine serum albumin-caffeic acid conjugate. Food Chemistry. 2018 Sep;261:283–91.

Laccase-catalyzed conjugation of BSA mediated by gallic acid: Preparation, characterization, and antioxidant activity

Year 2022, Volume: 9 Issue: 1, 29 - 36, 28.02.2022
https://doi.org/10.18596/jotcsa.952065

Abstract

Laccase is one of the enzymes that catalyze the oxidation of phenolic and non-phenolic substrates and show encouraging potential as a biocatalyst in the synthesis of bioactive compounds. It is known that phenolic acids have an antioxidant effect. Bovine serum albumin (BSA) shows gelling activity, and nutraceutical binding ability but it does not show antioxidant activity. In this study, BSA which has no antioxidant activity using laccase, started to show antioxidant activity with gallic acid (GA) conjugation. The synthesized conjugates were analyzed by polyacrylamide gel electrophoresis (PAGE), ultraviolet–visible spectrophotometry (UV-Vis), and Fourier-transform infrared spectroscopy (FTIR). Radical scavenging capacity for antioxidant activity was measured. GA-functionalized-BSA displayed greatly improved 2,2'-azinobis-(3- ethylbenzothiazoline-6-sulfonic acid) (ABTS) and 1,1-diphenyl-2- picryl-hydrazyl (DPPH) radical scavenging capacities, compared with the untreated BSA. Protein–flavonoid conjugates can improve the natural properties of proteins, being promising products to be used in medical, food and polymer fields where antioxidant ability is an essential feature.

References

  • 1. Ls R, Nja S. Anticancer Properties of Phenolic Acids in Colon Cancer – A Review. J Nutr Food Sci [Internet]. 2016 [cited 2021 Nov 29];06(02).
  • 2. Weng C-J, Yen G-C. Chemopreventive effects of dietary phytochemicals against cancer invasion and metastasis: Phenolic acids, monophenol, polyphenol, and their derivatives. Cancer Treatment Reviews. 2012 Feb;38(1):76–87.
  • 3. Tian R-R, Pan Q-H, Zhan J-C, Li J-M, Wan S-B, Zhang Q-H, et al. Comparison of Phenolic Acids and Flavan-3-ols During Wine Fermentation of Grapes with Different Harvest Times. Molecules. 2009 Feb 18;14(2):827–38.
  • 4. Badhani B, Sharma N, Kakkar R. Gallic acid: a versatile antioxidant with promising therapeutic and industrial applications. RSC Adv. 2015;5(35):27540–57.
  • 5. Sagdicoglu Celep AG, Demirkaya A, Solak EK. Antioxidant and anticancer activities of gallic acid loaded sodium alginate microspheres on colon cancer. Current Applied Physics. 2020 Jul;S1567173920301164.
  • 6. de Cristo Soares Alves A, Mainardes RM, Khalil NM. Nanoencapsulation of gallic acid and evaluation of its cytotoxicity and antioxidant activity. Materials Science and Engineering: C. 2016 Mar;60:126–34.
  • 7. Giardina P, Faraco V, Pezzella C, Piscitelli A, Vanhulle S, Sannia G. Laccases: a never-ending story. Cell Mol Life Sci. 2010 Feb;67(3):369–85.
  • 8. Su J, Noro J, Fu J, Wang Q, Silva C, Cavaco-Paulo A. Enzymatic polymerization of catechol under high-pressure homogenization for the green coloration of textiles. Journal of Cleaner Production. 2018 Nov;202:792–8.
  • 9. Su J, Castro TG, Noro J, Fu J, Wang Q, Silva C, et al. The effect of high-energy environments on the structure of laccase-polymerized poly(catechol). Ultrasonics Sonochemistry. 2018 Nov;48:275–80.
  • 10. Jiang Z, Yuan X, Yao K, Li X, Zhang X, Mu Z, et al. Laccase-aided modification: Effects on structure, gel properties and antioxidant activities of α-lactalbumin. LWT. 2017 Jul;80:355–63.
  • 11. Aljawish A, Chevalot I, Jasniewski J, Paris C, Scher J, Muniglia L. Laccase-catalysed oxidation of ferulic acid and ethyl ferulate in aqueous medium: A green procedure for the synthesis of new compounds. Food Chemistry. 2014 Feb;145:1046–54.
  • 12. Mattinen M-L, Hellman M, Permi P, Autio K, Kalkkinen N, Buchert J. Effect of Protein Structure on Laccase-Catalyzed Protein Oligomerization. J Agric Food Chem. 2006 Nov 1;54(23):8883–90.
  • 13. Livney YD. Milk proteins as vehicles for bioactives. Current Opinion in Colloid & Interface Science. 2010 Apr;15(1–2):73–83.
  • 14. Matsudomi N, Rector D, Kinsella JE. Gelation of bovine serum albumin and β-lactoglobulin; effects of pH, salts and thiol reagents. Food Chemistry. 1991 Jan;40(1):55–69.
  • 15. Božič M, Gorgieva S, Kokol V. Laccase-mediated functionalization of chitosan by caffeic and gallic acids for modulating antioxidant and antimicrobial properties. Carbohydrate Polymers. 2012 Mar;87(4):2388–98.
  • 16. Yu C, Liu X, Pei J, Wang Y. Grafting of laccase-catalysed oxidation of butyl paraben and p-coumaric acid onto chitosan to improve its antioxidant and antibacterial activities. Reactive and Functional Polymers. 2020 Apr;149:104511.
  • 17. Božič M, Štrancar J, Kokol V. Laccase-initiated reaction between phenolic acids and chitosan. Reactive and Functional Polymers. 2013 Oct;73(10):1377–83.
  • 18. Wolfenden BS, Willson RobinL. Radical-cations as reference chromogens in kinetic studies of ono-electron transfer reactions: pulse radiolysis studies of 2,2′-azinobis-(3-ethylbenzthiazoline-6-sulphonate). J Chem Soc, Perkin Trans 2. 1982;(7):805–12.
  • 19. Kim S, Cavaco-Paulo A. Laccase-catalysed protein–flavonoid conjugates for flax fibre modification. Appl Microbiol Biotechnol. 2012 Jan;93(2):585–600.
  • 20. Brand-Williams W, Cuvelier ME, Berset C. Use of a free radical method to evaluate antioxidant activity. LWT - Food Science and Technology. 1995;28(1):25–30.
  • 21. Arnao MB, Cano A, Alcolea JF, Acosta M. Estimation of free radical-quenching activity of leaf pigment extracts. Phytochem Anal. 2001 Mar;12(2):138–43.
  • 22. Grigoryan KR, Shilajyan HA. Analysis of the interaction of gallic acid and myoglobin by UV-vis absorption spectroscopy. Russ J Bioorg Chem. 2017 May;43(3):255–8.
  • 23. Grdadolnik J. Saturation effects in FTIR spectroscopy: intensity of amide I and amide II bands in protein spectra. Acta chimica slovenica. 2003;50(4):777–88.
  • 24. Fan Y, Liu Y, Gao L, Zhang Y, Yi J. Improved chemical stability and cellular antioxidant activity of resveratrol in zein nanoparticle with bovine serum albumin-caffeic acid conjugate. Food Chemistry. 2018 Sep;261:283–91.
There are 24 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Merve Bat Özmatara 0000-0002-6912-8825

Fatma Ertan 0000-0002-9572-9392

Publication Date February 28, 2022
Submission Date June 14, 2021
Acceptance Date July 16, 2021
Published in Issue Year 2022 Volume: 9 Issue: 1

Cite

Vancouver Bat Özmatara M, Ertan F. Laccase-catalyzed conjugation of BSA mediated by gallic acid: Preparation, characterization, and antioxidant activity. JOTCSA. 2022;9(1):29-36.