Enzymatic Synthesis of Olive-Based Ferulate Esters: Optimization by Response Surface Methodology
Authors: S. Mat Radzi, N. J. Abd Rahman, H. Mohd Noor, N. Ariffin
Abstract:
Ferulic acid has widespread industrial potential by virtue of its antioxidant properties. However, it is partially soluble in aqueous media, limiting their usefulness in oil-based processes in food, cosmetic, pharmaceutical, and material industry. Therefore, modification of ferulic acid should be made by producing of more lipophilic derivatives. In this study, a preliminary investigation of lipase-catalyzed trans-esterification reaction of ethyl ferulate and olive oil was investigated. The reaction was catalyzed by immobilized lipase from Candida antarctica (Novozym 435), to produce ferulate ester, a sunscreen agent. A statistical approach of Response surface methodology (RSM) was used to evaluate the interactive effects of reaction temperature (40-80°C), reaction time (4-12 hours), and amount of enzyme (0.1-0.5 g). The optimum conditions derived via RSM were reaction temperature 60°C, reaction time 2.34 hours, and amount of enzyme 0.3 g. The actual experimental yield was 59.6% ferulate ester under optimum condition, which compared well to the maximum predicted value of 58.0%.
Keywords: Ferulic acid, Enzymatic Synthesis, Esters, RSM.
Digital Object Identifier (DOI): doi.org/10.5281/zenodo.1094130
Procedia APA BibTeX Chicago EndNote Harvard JSON MLA RIS XML ISO 690 PDF Downloads 2153References:
[1] R.R. Koraćand K.M. Khambholja."Potential of herbs in skin protection from ultraviolet radiation”. Phcog. Rev., vol. 5, pp. 164-173, 2011.
[2] E. Manová, N. Goetz, U. Hauri, C. Bogdal, and K. Hungerbuhler. "Organic UV filters in personal care products in Switzerland: a survey of occurrence and concentrations”. Int. J. Hyg. Environ. Health,vol. 216, pp. 508-514, 2013.
[3] S. Schalkaand V. M. S. Reis. "Sun protection factor: meaning and controversies”. An. Bras. Dermatol.,vol. 86(3), pp. 507-515, 2011.
[4] S. Gonzalez, Y. Gilaberte, N. Philips, and A. Juarranz, A. "Current trends in photoprotection – a new generation of oral photoprotectors” TODJ., vol. 5, pp. 6-14. 2011.
[5] F. Di Domenico, M. Perluigi, C. Foppoli, C. Blarzino, R. Coccia, F. De Marco, D. A. Butterfield and C. Cini, "Protective effect of ferulic acid ethyl ester against oxidative stress mediated by UVB irradiation in human epidermal melanocytes”. Free Radical Res.,vol. 1, pp. 1-11, 2009.
[6] C. Oresajo, T. Stephans, P. D. Hino, R. M. Law, M. Yatskayer, M., P. Foltis, S. Pillai and S. R. Pinnell. "Protective effects of a topical antioxidant mixture containing vitamin C, ferulic acid and phloretin against ultraviolet-induced photodamage in human skin”. J. Cosmet. Dermatol., vol. 7,pp. 290-297. 2008.
[7] C. Rossi, C., Schoubben, A., Ricci, M., Perioli, L., Ambrogia, V., Latterini, L., Aloisiand A. Rossi. "Intercalation of the radical scavenger ferulic acid in hydrotalcite-like anionic clays”.Int. J. Pharm.,vol. 295,pp. 47-55. 2005
[8] E. de Man and H. V. Peeke. "Dietary ferulic acid, biochanin A, and the inhibition of reproductive behaviour in Japanese quail (Coturnix coturnix)”. Pharmacol. Biochem. Behav.,vol. 17, pp. 405-411. 1982.
[9] N. G. Li, Z. H. Shi, Y. P. Tang, B. Q. Li, J. A. Duan. "Highly esterification of ferulic acid under microwave irradiation”. Molecules. vol. 14, pp. 2118-2126. 2009.
[10] T. Matsuo, T. Kobayashi, Y. Kimura, M. Tsuchiyama, T. Sakamoto and S. Adachi. "Synthesis of glycerylferulate by immobilized acid esterase”. Biotechnol. Lett. vol. 30,pp. 2151-2156. 2008.
[11] Y. Yoshida, Y. Kimura, M. Kadota, T. Tsunoand S. Adachi."Continuous synthesis of alkyl ferulate by immobilized Candida antarctica lipase at high temperature”. Biotectnol.Lett.,vol. 28,pp. 1471-1474. 2009.
[12] H. Stamatis, H. V. Seretiand F. N. Kolisis. "Enzymatic synthesis of hydrophobic derivatives of natural phenolic acids in organic media”. J. Mol. Catal. B: Enzymatic,vol. 11,pp. 323-328. 2001.
[13] H. Stamatis, V. Seretiand F. N. Kolisis. "Studies on the enzymatic synthesis of lipophilic derivatives of natural antioxidants”. J. Am. Oil Chem. Soc.,vol. 76,pp.1505-1510. 1999.
[14] J. Y. Xin, L. L. Chen, Y. X. Zhang, E. Zhang and C. G. Xia."Lipase catalyzed transesterification of ethyl ferulate with triolein in solvent-free medium”. Food Bioprod. Process,vol. 89,pp. 457-462. 2011.
[15] Z. Yang, M. Glasiusand X. Xu. "Enzymatic transesterification of ethyl ferulate with fish oil and reaction optimization by Response Surface Methodology”. Food Technol. Biotech.,vol. 50(1),pp. 88-97. 2012.
[16] J. Y. Xin, L. Zhang, L. L. Chen, Y. Zheng, X. M. Wu and C. G. Xia. "Lipase-catalyzed synthesis of ferulyloleins in solvent-free medium”. Food Chem. vol. 112,pp. 640-645. 2009.
[17] S. Karboune, R. St-Louisand S. Kermasha. "Enzymatic synthesis of structured phenolic lipids by acidolysis of flaxseed oil with selected phenolic acids”. J. Mol. Catal. B: Enzymatic,vol. 52-53, pp. 96-105. 2008.
[18] J. A. Laszlo and D. L. Compton. "Enzymatic glycerolysis and transesterification of vegetable oil for enhanced production of feruloylatedglycerols”. J. Am. Oil Chem. Soc.,vol. 83(9),pp. 765-770. 2006.
[19] V. Lavelliand L. Bondesan. "Secoiridoids, tocopherols, and antioxidant activity of monovarietal extra virgin olive oils extracted from destoned fruits”. J. Agric. Food Chem.vol. 53, pp. 1102-1107. 2005.
[20] J. Ullah, M. Hamayoun, T. Ahmad, M. Ayuband M. Zarafullah. "Effect of light, natural and synthetic antioxidants on stability of edible oils and fats”. Asian J. Plant Sci., vol. 2,pp.1192-1194. 2003.
[21] M. A. Ruiz, J. L. Arias and V. Gallardo and V. Olives, "Olive oil in health and disease prevention”. In skin creams made with olive oil, United States: Elsevier Inc., 2003, pp.1133-1141.
[22] M. Y. Noordin, V. C. Venkatesh, S. Sharif, S. Elting, S. and A. Abdullah. "Application of response surface methodology in describing the performance of coated carbide tools when turning AISI 1045 steel”. J. Mater. Process Tech. vol. 1(1),pp. 46-58. 2004.
[23] J. Vainionpaa. "Modelling of extrusion cooking cereal using Response Surface Methodology”. J. Food Eng.vol. 13, pp.1-26. 1991.
[24] M. S. R. C. Murthy, T. Swaminathan, S. K. Rakshit and Y. Kosugi. "Statistical optimization of lipase catalysed hydrolysis of methyloleate by response surface methodology”. Bioprocess Eng. vol. 22, pp. 35-39. 2000.
[25] S. Harikrisna, A. P. Sattur and N. G. Karant. "Lipase-catalyzed synthesis of isoamylisobutyrate optimization using composite rotatable design”. Process Biochem. vol. 37, pp. 9-16. 2003.
[26] S. E. Ashari, R. Mohamad, A. Ariff, M. Basriand A. B. Salleh. "Optimization of enzymatic synthesis of palm-based kojic acid ester using Response surface methodology”. J. Oleo Sci.vol. 58(10), pp. 503-510. 2009.
[27] E. R. Gunawan, M. Basri, M. B. Abdul Rahman, A. B. Sallehand R. N. Z. Abdul Rahman. "Lipase-catalyzed synthesis of palm-based wax esters”. J. Oleo Sci., vol. 53, pp. 471-477. 2004.
[28] D. L. Compton, J. A. Laszlo and M. A. Berhow. "Lipase-catalyzed synthesis of ferulate esters”. J. Am. Oil Chem. Soc.,vol. 77(5),pp. 513-519. 2000.