Syntheses via phenolic oxidative coupling using crude peroxidase from Brassica juncea (L) Czern leaves and antioxidant evaluation of dimeric thymol

Authors

  • Yusnidar Yusuf Faculty of Pharmacy and Sciences, Universitas Muhammadiyah Prof. Dr. HAMKA, Islamic Center, Klender, 13460, Jakarta, Indonesia
  • Budi Arman Faculty of Pharmacy and Sciences, Universitas Muhammadiyah Prof. Dr. HAMKA, Islamic Center, Klender, 13460, Jakarta, Indonesia
  • Antonius H. Cahyana Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Indonesia, Kampus UI Depok, 16424, Jawa Barat, Indonesia

Abstract

The ability of a crude Brassica juncea (L) Czern peroxidase as green and edible catalyst for phenolic oxidative dimerization of thymol is presented.  Crude peroxidase was isolated and partially purified using precipitation method with gradient concentration of ammonium sulphate and dry ice-acetone combination as temperature regulator.  The crude peroxidase was then analyzed qualitatively and quantitatively using guaiacol as a model substrate and amino antypirin activity test, respectively, and the positive result was confirmed.  From the phenolic oxidative reaction, dimerization of thymol was carried out under extremely mild reaction condition in aqueous medium.  The product was checked by using Fourier Transform Infrared (FTIR) and Gas Chromatography-Mass Spectrometry (GC-MS).  Furthermore, the biological activity test using DPPH radical scavenging method was confirmed that the dimeric thymol showed 15 times greater than monomeric thymol in term of antioxidant capacity.

References

- P. Nagaraja, A. Shivakumar and A. K. Shrestha, J. Agric. Food Chem., 2009, 57, 5173-5177.

- J. B. Adams, J. Food Technol., 1978, 13, 281-297.

- J. R. Whitaker, Principles of enzymology for food sciences, 2nd ed., Dekker, New York, 1994, pp. 183-192, 288-293.

- C. Rodrigo, M. Rodrigo, A. Alvarruiz and A. Frigola, J. Food Prot., 1996, 59, 1065-1071.

- P. F. Dowd, D. A. Herms, M. A. Berhow and L. M. Lagrimini, Plant Peroxidase Newslett., 2000, 14, 93-101.

- T. Thongsook and D. M. Barrett, J. Agric. Food Chem., 2005, 53, 3206-3214.

- D. S. Robinson and N. A. M. Askin, Oxidative enzymes in foods, 1st ed., Elsevier Applied Science, London UK, 1991, pp. 1-37.

- S. S. Deepa and C. Arumughan, Phytochemistry, 2002, 61, 503-511.

- J. C. Leon, I. S. Alpeeva, T. A. Chubar, I. Yu. Galaev, E. Csoregi and I. Yu. Sakharov, Plant Sci., 2002, 163, 1011.

- R. R. Hamed, T. M. Maharem, M. M. A. Fatah and F. S. Ataya, Phytochemistry, 1998, 48, 1291.

- M. A. Duarte-Vazquez, B. E. Garcia-Almendarez, C. Regalado and J. R. Whitaker, J. Agric. Food Chem., 2001, 49, 4450-4456.

- J. N. Rodriguez-Lopez, J. C. Espin, F. del Amor, J. Tudela, V. Martinez, A. Cerda and F. Garcia-Canovas, J. Agric. Food Chem., 2000, 48, 1537.

- K. M. McLellan and D. S. Robinson, Food Chem., 1987, 23, 305-319.

- C. Regalado, O. P. Arvizu, B. E. G. Almendarez and J. R. Whitaker, J. Food Biochem., 1999, 23, 435.

- K. M. McLellan and D. S. Robinson, Food Chem., 1987, 26, 97-107.

- B. K. Kristensen, H. Bloch and S. K. Rasmussen, Plant Physiol, 1999, 120, 501.

- A. Yemenicioglu, M. Ozkan and B. Cemeroglu, J. Agric. Food Chem., 1998, 46, 4158.

- E. Clemente, Phytochemistry, 1998, 49, 29.

- M. Kvaratskhelia, C. Winkel and R. N. F. Thorneley, Plant Physiol, 1997, 114, 1237.

- F. Pomar, M. A. Bernal, J. Diaz and F. Merino, Phytochemistry, 1997, 46, 1313.

- A. R. Nair and A. M. Showalter, Biochem. Biophys. Res. Commun., 1996, 226, 254.

- I. G. Gazaryan and L. M. Lagrimini, Phytochemistry, 1996, 41, 1029.

- D. A. Converso and M. E. Fernandez, Phytochemistry, 1995, 40, 1341.

- A. A. Khan and D. S. Robinson, Food Chem., 1993, 46, 61.

- B. Halpin, R. Pressey, J. Jen and N. Mondy, J. Food Sci., 1989, 54, 644.

- H. C. Lee and B. P. Clein, J. Food Biochem., 1990, 14, 137.

- E. da Silva, E. J. Lourenco and V. A. Neves, Phytochemistry, 1990, 29, 1051.

- Z. El Shamei, the purification and properties of peroxidase in spinach. I. Isolation and purification. In Biotechnology and Food Industry, proceedings of international symposium held in Budapest, Hungary, Oct 5-9, 1987, edited by J. Hollow and D.

Torley, Akademiai Kiado, Budapest, 1988, pp. 257-265.

- P. H. Moulding, D. E. Singleton, K. M. McLellan and D. S. Robinson, Int. J. Food Sci. Technol., 1988, 23, 343, 351.

- H. Ito, N. Hiraoka, A. Ohbayashi and Y. Ohashi, Agric. Biol. Chem, 1991, 55, 2445, 2454.

- B. A. Triplett and J. E. Mellon, Plant Sci., 1992, 81, 147-154.

- R. N. Chibbar and R. B. van Huystee, Plant Physiol, 1984, 75, 956-958.

-J. J. Jen, A. Seo and W. H. Flurkey, J. Food Sci., 1980, 45, 60-63.

- A. Signored and J. Crouzed, Agric. Biol. Chem., 1982, 46, 459.

- Z. Wang and B. S. Luh, J. Food Sci., 1983, 48, 1412.

- P. M. Civello, G. A. Martinez, A. R. Chaves and M. C. Anon, J. Agric. Food Chem.,

, 43, 2596-2601.

- G. H. Onsa, N. Bin Saari, J. Selamat and J. Bakar, Food Chem., 2004, 85, 365-376.

- Y. Anita, G. Widiyarti and J. Abbas, J. Appl. Pharm. Sci., 2014, 4 (4), 62-65.

- J. Takebayashi, A. Tai and I. Yamamoto, Biol. Pharm. Bull., 2006, 29, 766-771.

- I. Gulcin, E. Bursal, M. H. Sehitoglu, M. Bilsel and A. C. Goren, Food and Chem.

Toxic., 2010, 48, 2227-2238.

- V. Roginsky and E. A. Lissi, Food Chem., 2005, 92, 235-254.

- J. Takebayashi, A. Tai and I. Yamamoto, Biol. Pharm. Bull., 2003, 26, 1368-1370.

-V. Fogliano, V. Verde, G. Randazzo and A. Ritieni, J. Agric. Food Chem., 1999, 47, 1035-1040.

- R. Apak, K. Guclu, M. Ozyurek, S. E. Karademir and E. Erca, Int. J. Food Sci. Nut., 2006, 57, 292-304.

- S. Karaman, E. Tutem, K. S. Baskan, R. Apak, Food Chem., 2010, 120, 1201-1209.

- T. C. P. Dinis, V. M. C. Madeira and L. M. Almeida, Arc. Biochem. Biophys., 1994, 315, 161-169.

- M. Blois, Nature, 1958, 181, 1199.

- T. Kiso, M. Shizuma, H. Murakami, T. Kiryu, K. Hozono, T. Terai and H. Nakano, J. Mol. Catal. B: Ezymatic, 2007, 45, 50-56.

Downloads

Published

2015-01-08

Issue

Section

Bioorganic Chemistry