Lipase catalysed transesterification of palm stearin with ferulic acid in solvent-free media

References

• Alves JS, Vieira NS, Cunha AS, Silva AM, Zachia Ayub MA, Fernandez-Lafuente R, Rodrigues RC. 2014. Combi-lipase for heterogeneous substrates: a new approach for hydrolysis of soybean oil using mixtures of biocatalysts. RSC Adv. 4(14):6863–6868.
   Web of Science ®Google Scholar
• Barone E, Calabrese V, Mancuso C. 2009. Ferulic acid and its therapeutic potential as a hormetin for age-related diseases. Biogerontol J. 10(2):97–108.
   PubMed Web of Science ®Google Scholar
• Bellot JC, Choisnard L, Castillo E, Marty A. 2001. Combining solvent engineering and thermodynamic modeling to enhance selectivity during monoglyceride synthesis by lipase-catalyzed esterification. Enzyme Microb Technol. 28(4–5):362–369.
   PubMed Web of Science ®Google Scholar
• Bornscheuer UT. 2003. Immobilizing enzymes: how to create more suitable biocatalysts. Angew Chem Int Ed Engl. 42(29):3336–3337.
   PubMed Web of Science ®Google Scholar
• Choo W-S, Birch EJ. 2009. Radical scavenging activity of lipophilized products from lipase-catalyzed transesterification of triolein with cinnamic and ferulic acids. Lipids. 44(2):145–152.
   PubMed Web of Science ®Google Scholar
• Choo W-S, Birch EJ, Stewart I. 2009. Radical scavenging activity of lipophilized products from transesterification of flaxseed oil with cinnamic acid or ferulic acid. Lipids. 44(9):807–815.
   PubMed Web of Science ®Google Scholar
• Compton DL, Laszlo JA, Evans KO. 2012. Antioxidant properties of feruloyl glycerol derivatives. Ind Crops Prod. 36(1):217–221.
   Web of Science ®Google Scholar
• Domínguez de María P, Carboni-Oerlemans C, Tuin B, Bargeman G, Van der Meer A, Van Gemert R. 2005. Biotechnological applications of Candida antarctica lipase A: state-of-the-art. J Mol Catal B Enzym. 37(1–6):36–46.
   Google Scholar
• Giuliani s, Piana C, Setti L, Hochkoeppler A, Pifferi PG, Williamson G, Faulds CB. 2001. Synthesis of pentylferulate by a feruloyl esterase from Aspergillus niger using water-in-oil microemulsions. Biotechnol Lett. 23(4):325–330.
   Web of Science ®Google Scholar
• Hashem AI, Abou Elmagd WSI, Salem AE, El-Kasaby M, El-Nahas AM. 2013a. Conversion of some vegetable oils into synthetic lubricants via two successive transesterifications. Energy Sources Part A Recov Utiliz Environ Effects. 35(10):909–912.
   Web of Science ®Google Scholar
• Hashem AI, Abou Elmagd WSI, Salem AE, El-Kasaby M, El-Nahas AM. 2013b. Treatment of some vegetable oils with maleic anhydride, a route to synthetic lubricants. Energy Sources Part A Recov Utiliz Environ Effects. 35(15):1463–1466.
   Web of Science ®Google Scholar
• Hashem AI, Abou Elmagd WSI, Salem AE, El-Kasaby M, El-Nahas AM. 2013c. Conversion of some vegetable oils into synthetic lubricants. Energy Sources Part A Recov Utiliz Environ Effects. 35(5):397–400.
   Web of Science ®Google Scholar
• Hernández-Corroto E, Sánchez-Milla M, Sánchez-Nieves J, Javier de la Mata F, Luisa Marina M, Concepción García M. 2020. Immobilization of thermolysin enzyme on dendronized silica supports. Evaluation of its feasibility on multiple protein hydrolysis cycles. Int J Biol Macromol. 165(Pt B):2338–2348.
   PubMedGoogle Scholar
• Huang S-M, Wu P-Y, Chen J-H, Kuo C-H, Shieh C-J. 2018. Developing a high-temperature solvent-free system for efficient biocatalysis of octyl ferulate. Catalysts. 8(8):338.
   Web of Science ®Google Scholar
• Itagaki S, Kurokawa T, Nakata C, Saito Y, Oikawa S, Kobayashi M, Hirano T, Iseki K. 2009. In vitro and in vivo antioxidant properties of ferulic acid: a comparative study with other natural oxidation inhibitors. Food Chem. 114(2):466–471.
   Web of Science ®Google Scholar
• Karboune S, Safari M, Lue B-M, Yeboah FK, Kermasha S. 2005. Lipase-catalyzed biosynthesis of cinnamoylated lipids in a selected organic solvent medium. J Biotechnol. 119(3):281–290.
   PubMed Web of Science ®Google Scholar
• Kikuzaki H, Hisamoto M, Hirose K, Akiyama K, Taniguchi H. 2002. Antioxidant properties of ferulic acid and its related compounds. J Agric Food Chem. 50(7):2161–2168.
   PubMed Web of Science ®Google Scholar
• Kirk O, Christensen MW. 2002. Lipases from Candida antarctica: unique biocatalysts from a unique origin. Org Process Res Dev. 6(4):446–451.
   Web of Science ®Google Scholar
• Lee DH, Kim JM, Shin HY, Kang SW, Kim SW. 2006. Biodiesel production using a mixture of immobilized Rhizopus oryzae and Candida rugosa lipases. Biotechnol Bioproc Eng. 11(6):522–525.
   Web of Science ®Google Scholar
• Maharani CA, Suharti S, Wonorahardjo S. 2020. Optimizing the immobilization of lipase enzyme (Aspergillus oryzae) in the silica and silica-cellulose matrix by adsorption method. J Phys Conf Ser. 1595:12011.
   Google Scholar
• Minovska V, Winkelhausen E, Kuzmanova S. 2005. Lipase immobilized by different techniques on various support materials applied in oil hydrolysis. J Serb Chem Soc. 70(4):609–624.
   Web of Science ®Google Scholar
• Monteiro RRC, Virgen-Ortiz JJ, Berenguer-Murcia Á, da Rocha TN, dos Santos JCS, Alcántara AR, Fernandez-Lafuente R. 2021. Biotechnological relevance of the lipase A from Candida antarctica. Catal Today. 362:141–154.
   Web of Science ®Google Scholar
• Ngin P, Cho K, Han O. 2021. Immobilization of soybean lipoxygenase on nanoporous rice husk silica by adsorption: retention of enzyme function and catalytic potential. Molecules. 26(2):291.
   Web of Science ®Google Scholar
• Nuzul A, Guo Z, Xu X. 2008. Enzymatic interesterification of palm stearin and coconut oil by a dual lipase system. J Am Oil Chem Soc. 85(1):37–45.
   Web of Science ®Google Scholar
• Peres DD, Sarruf FD, Areias de Oliveira C, Velasco MVR, Baby AR. 2018. Ferulic acid photoprotective properties in association with UV filters: multifunctional sunscreen with improved SPF and UVA-PF. J Photochem Photobiol B Biol. 185:46–49.
   PubMed Web of Science ®Google Scholar
• Poppe JK, Matte CR, Fernandez-Lafuente R, Rodrigues RC, Ayub MAZ. 2018. Transesterification of waste frying oil and soybean oil by combi-lipases under ultrasound-assisted reactions. Appl Biochem Biotechnol. 186(3):576–589.
   PubMed Web of Science ®Google Scholar
• Rahman NJA, Radzi SM, Noor HM. 2015. Dual lipases system in transesterification of ethyl ferulate with olive oil: optimization by response surface methodology. Asian J Appl Sci. 3(1):173–179.
   Google Scholar
• Rodríguez D, Morales N, García LM, Godoy C, Toro Alzate EC. 2019. Novel Combi-lipase systems for fatty acid ethyl esters production. Catalysts. 9(6):546.
   Web of Science ®Google Scholar
• Sabally K, Karboune S, St-Louis R, Kermasha S. 2006a. Lipase-catalyzed transesterification of trilinolein or trilinolenin with selected phenolic acids. J Am Oil Chem Soc. 83(2):101–107.
   Web of Science ®Google Scholar
• Sabally K, Karboune S, St-Louis R, Kermasha S. 2006b. Lipase-catalyzed transesterification of dihydrocaffeic acid with flaxseed oil for the synthesis of phenolic lipids. J Biotechnol. 127(1):167–176.
   PubMed Web of Science ®Google Scholar
• Sharma RK, Gaba G, Kumar A, Puri A. 2013. Functionalized silica gel as a green material for metal remediation. In: Mishra A, Clark JH, editors. Green materials for sustainable water remediation and treatment. Cambridge: The Royal Society for Chemistry; p. 105–134.
   Google Scholar
• Silva TMS, dos Santos FP, Evangelista-Rodrigues A, da Silva EMS, da Silva GS, de Novais JS, dos Santos FdAR, Camara CA. 2013. Phenolic compounds, melissopalynological, physicochemical analysis and antioxidant activity of Jandaíra (Melipona subnitida) honey. J Food Compos Anal. 29(1):10–18.
   Web of Science ®Google Scholar
• Sorour N, Karboune S, Saint-Louis R, Kermasha S. 2012. Lipase-catalyzed synthesis of structured phenolic lipids in solvent-free system using flaxseed oil and selected phenolic acids as substrates. J Biotechnol. 158(3):128–136.
   PubMed Web of Science ®Google Scholar
• Sun S, Chen X, Jiang C. 2018. Enhanced synthesis of feruloylated acylglycerols by the lipase-catalyzed transesterification of glyceryl monoferulate with different acyl donors using ionic liquids as reaction solvents. J Biotechnol. 280:31–37.
   PubMed Web of Science ®Google Scholar
• Sun S, Hu B, Qin F, Bi Y. 2015. Comparative study of soybean oil and the mixed fatty acids as acyl donors for enzymatic preparation of feruloylated acylglycerols in ionic liquids. J Agric Food Chem. 63(32):7261–7269.
   PubMed Web of Science ®Google Scholar
• Sun S, Qin F, Bi Y, Chen J, Yang G, Liu W. 2013. Enhanced transesterification of ethyl ferulate with glycerol for preparing glyceryl diferulate using a lipase in ionic liquids as reaction medium. Biotechnol Lett. 35(9):1449–1454.
   PubMed Web of Science ®Google Scholar
• Sun S, Song F, Bi Y, Yang G, Liu W. 2012. Solvent-free enzymatic transesterification of ethyl ferulate and monostearin: optimized by response surface methodology. J Biotechnol. 164(2):340–345.
   PubMed Web of Science ®Google Scholar
• Sun S, Wang P, Zhu S. 2017. Enzymatic incorporation of caffeoyl into castor oil to prepare the novel castor oil-based caffeoyl structured lipids. J Biotechnol. 249:66–72.
   PubMed Web of Science ®Google Scholar
• Sun S, Yaping L, Zhu S. 2019. Influence of ionic liquid on Novozym 435-catalyzed the transesterification of castor oil and ethyl caffeate. 3 Biotech. 9(1):34.
   PubMedGoogle Scholar
• Sun S, Zhu S, Bi Y. 2014. Solvent-free enzymatic synthesis of feruloylated structured lipids by the transesterification of ethyl ferulate with castor oil. Food Chem. 158:292–295.
   PubMed Web of Science ®Google Scholar
• Yang Z, Glasius M, Xu X. 2012. Enzymatic transesterification of ethyl ferulate with fish oil and reaction optimization by response surface methodology. Food Technol Biotechnol. 50:88–97.
   Web of Science ®Google Scholar
• Yildiz H, Ozyilmaz E, Bhatti AA, Yilmaz M. 2017. Enantioselective resolution of racemic flurbiprofen methyl ester by lipase encapsulated mercapto calix[4]arenes capped Fe3O4 nanoparticles. Bioprocess Biosyst Eng. 40(8):1189–1196.
   PubMed Web of Science ®Google Scholar
• Yilmaz E. 2012. Enantioselective enzymatic hydrolysis of racemic drugs by encapsulation in sol–gel magnetic sporopollenin. Bioprocess Biosyst Eng. 35(4):493–502.
   PubMed Web of Science ®Google Scholar
• Yilmaz E, Sezgin M, Yilmaz M. 2009. Immobilized copper-ion affinity adsorbent based on a cross-linked β-cyclodextrin polymer for adsorption of Candida rugosa lipase. Biocatal Biotransform. 27(5–6):360–366.
   Web of Science ®Google Scholar
• Zheng Y, Quan J, Ning X, Zhu L-M. 2008. Enhancement in the synthesis of novel feruloyl lipids (feruloyl butyryl glycerides) by enzymatic biotransformation using response surface methodology. J Agric Food Chem. 56(23):11493–11498.
   PubMed Web of Science ®Google Scholar
• Zheng Y, Wu X-M, Branford-White C, Quan J, Zhu L-M. 2009. Dual response surface-optimized process for feruloylated diacylglycerols by selective lipase-catalyzed transesterification in solvent free system. Bioresour Technol. 100(12):2896–2901.
   PubMed Web of Science ®Google Scholar
• Zoumpanioti M, Merianou E, Karandreas T, Stamatis H, Xenakis A. 2010. Esterification of phenolic acids catalyzed by lipases immobilized in organogels. Biotechnol Lett. 32(10):1457–1462.
   PubMed Web of Science ®Google Scholar