Enzymatic Synthesis Of Olive-Based Ferulate Esters: Optimization By Response Surface Methodology

• Main Authors: S. Mat Radzi, N. J. Abd Rahman, H. Mohd Noor, N. Ariffin
• Format: Text
• Language: English
• Published: Zenodo 2014
• Subjects: Ferulic acid; Enzymatic Synthesis; Esters; RSM.; Gonzalez; Manov; Antarc*; Antarctica
• Online Access: https://dx.doi.org/10.5281/zenodo.1094130; https://zenodo.org/record/1094130

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%. : {"references": ["R.R. Kora\u0107and K.M. Khambholja.\"Potential of herbs in skin protection from ultraviolet radiation\". Phcog. Rev., vol. 5, pp. 164-173, 2011.", "E. Manov\u00e1, 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.", "S. Schalkaand V. M. S. Reis. \"Sun protection factor: meaning and controversies\". An. Bras. Dermatol.,vol. 86(3), pp. 507-515, 2011.", "S. Gonzalez, Y. Gilaberte, N. Philips, and A. Juarranz, A. \"Current trends in photoprotection \u2013 a new generation of oral photoprotectors\" TODJ., vol. 5, pp. 6-14. 2011.", "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.", "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.", "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", "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.", "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.\n[10]\tT. 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.\n[11]\tY. 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.\n[12]\tH. 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.\n[13]\tH. 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.\n[14]\tJ. 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.\n[15]\tZ. 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.\t 2012.\n[16]\tJ. 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.\n[17]\tS. 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.\n[18]\tJ. 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.\n[19]\tV. 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.\n[20]\tJ. 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.\n[21]\tM. 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.\n[22]\tM. 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.\n[23]\tJ. Vainionpaa. \"Modelling of extrusion cooking cereal using Response Surface Methodology\". J. Food Eng.vol. 13, pp.1-26. 1991.\n[24]\tM. 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.\n[25]\tS. 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.\n[26]\tS. 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.\n[27]\tE. 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.\n[28]\tD. 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."]}