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Production of Omega-3 Fatty Acids Acylglycerides by Lipase-Catalyzed Glycerolysis of Sardine Oil in Different Reaction Media

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Production of Omega-3 Fatty Acids Acylglycerides by Lipase-Catalyzed Glycerolysis of Sardine Oil in Different Reaction Media UNIVERSIDAD DE BURGOS Departamento de Biotecnología y Ciencia de los Alimentos Production of omega-3 fatty acids acylglycerides by lipase-catalyzed glycerolysis of sardine oil in different reaction media TESIS DOCTORAL Ángela García Solaesa Burgos, 2017 Production of omega-3 fatty acids acylglycerides by lipase-catalyzed glycerolysis of sardine oil in different reaction media Memoria que para optar al grado de Doctor por la Universidad de Burgos en el programa Avances en Ciencia y Biotecnología Alimentarias presenta ÁNGELA GARCÍA SOLAESA Burgos, 2017 UNIVERSIDAD DE BURGOS Departamento de Biotecnología y Ciencia de los Alimentos Dña. MARÍA TERESA SANZ DIEZ y Dña. SAGRARIO BELTRÁN CALVO, Profesoras del Departamento de Biotecnología y Ciencia de los Alimentos de la Universidad de Burgos, CERTIFICAN: Que la licenciada Dña. Ángela García Solaesa ha realizado bajo su dirección el trabajo titulado “Production of omega-3 fatty acids acylglycerides by lipase-catalyzed glycerolysis of sardine oil in different reaction media”, cuyo título en castellano es: “Producción de acilglicéridos de ácidos grasos omega-3 mediante glicerolisis de aceite de sardina catalizada por lipasas en diferentes medios de reacción”. Considerando que dicho trabajo reúne los requisitos exigidos para ser presentado como Tesis Doctoral, expresan su conformidad con dicha presentación. Para que conste, firman el presente certificado. En Burgos, a 28 de Agosto de 2017 Fdo. María Teresa Sanz Diez Fdo. Sagrario Beltrán Calvo UNIVERSIDAD DE BURGOS Departamento de Biotecnología y Ciencia de los Alimentos D. JOSÉ MANUEL BENITO MORENO, coordinador del programa de doctorado “Avances en Ciencia y Biotecnología Alimentarias de la Universidad de Burgos, CERTIFICA: Que la memoria titulada “Production of omega-3 fatty acids acylglycerides by lipase- catalyzed glycerolysis of sardine oil in different reaction media” presentada por Dña. Ángela García Solaesa, Licenciada en Ciencia y Tecnología de los Alimentos y Máster en Seguridad y Biotecnologia Alimentarias, ha sido realizada en el Departamento de Biotecnología y Ciencia de los Alimentos bajo la dirección de las Dras. María Teresa Sanz Diez y Sagrario Beltrán Calvo, y en representación de la Comisión Académica del Programa de Doctorado, autoriza su presentación para ser defendida como Tesis Doctoral. Para que conste, y surta los efectos oportunos, firmo el presente certificado. En Burgos, a 28 de Agosto de 2017 Fdo. José Manuel Benito Moreno Coordinador del Programa de Doctorado Este trabajo ha sido realizado en el marco de los siguientes proyectos de Investigación desarrollados en el seno del Grupo de investigación Biotecnología Industrial y Medioambiental, reconocido por la UBU (GIR-UBU BIOIND) y por la Junta de Castilla y León como Unidad de Investigación Consolidada UIC-128. • PROCESOS CON FLUIDOS SUPERCRITICOS APLICADOS A LA PRODUCCION Y SEPARACION DE ACILGLICERIDOS ENRIQUECIDOS EN OMEGA-3, financiado por el Ministerio de Economía y Competitividad y el Fondo Europeo de Desarrollo Regional (CTQ2012-39131-C02-01) • APLICACIÓN DE TECNOLOGÍAS EMERGENTES A LA FORMULACIÓN DE COMPUESTOS BIOACTIVOS DE INTERÉS PARA LA INDUSTRIA ALIMENTARIA, financiado por la Junta de Castilla y León y el Fondo Europeo de Desarrollo Regional (BU055U16) AGRADECIMIENTOS A la Universidad de Burgos por financiar mi contrato predoctoral y al MINECO, la JCyL y Fondos FEDER por financiar los proyectos CTQ2012-39131-C02-01 y BU055U16 en los que he trabajado. A mis directoras de Tesis. A Tere, por su dedicación, su comprensión y su infinita ayuda. Por ser mucho más que una directora de tesis, por haber estado siempre ahí como una compañera y amiga. A Sagrario, por la confianza que un día puso en mí para comenzar este proyecto. Por sus consejos y su generosidad, y por haber contado conmigo en tantas ocasiones. A todos los compañeros del Área de Ingeniería Química que han colaborado en esta Tesis. En especial agradecer a Beti todo lo que me ha enseñado, la ayuda que siempre me ha brindado y su confianza. También agradecer a Rodrigo toda su ayuda y disposición con los montajes “supercríticos”; y a Sarai, por haberme echado una mano en esta última etapa, por su disposición y su amistad. Al Prof. Zheng Guo de la Universidad de Aarhus y a la Dra. Sara Cunha de la Universidad de Oporto, por aceptarme en sus grupos de investigación para realizar mis estancias predoctorales y enseñarme tanto en tan poco tiempo. A mis amigas Andrea, Raquel, Gloria y Helen; por haber estado ahí, por su interés y por el apoyo que me han brindado. Y por último, mi más profundo agradecimiento a mis padres, que me lo han dado todo, a mi hermana Virginia y a David, por apoyarme siempre y darme tan buenos consejos. A Dani, por animarme cada día, por su comprensión y por la admiración que me transmite. GENERAL INDEX GENERAL INDEX SUMMARY OF THE THESIS ................................................................................................. 1 INTRODUCTION …………………………………………………………………………………………………………….5 OBJECTIVES ...................................................................................................................... 25 RESULTS ........................................................................................................................... 29 Chapter 1: Liquid–liquid equilibria for systems glycerol + sardine oil + tert-alcohols ........................... 33 Chapter 2: Glycerolysis of sardine oil catalyzed by a water dependent lipase in different tert-alcohols as reaction medium.............................................................................................................. 59 Chapter 3: Kinetic study and kinetic parameters of lipase‐catalyzed glycerolysis of sardine oil in a homogeneous medium ........................................................................................................ 83 Chapter 4: Production and concentration of monoacylglycerols rich in omega-3 polyunsaturated fatty acids by enzymatic glycerolysis and molecular distillation ................................................115 Chapter 5: Substrates emulsification process to improve lipase-catalyzed sardine oil glycerolysis in different systems. Determination of lipid oxidation of the reaction products ..................137 Chapter 6: Effect of temperature on oxidation kinetics and adsorption capacity of commercial immobilized lipases supports to reduce oxidation products in sardine oil ........................161 CONCLUSIONS ................................................................................................................191 Appendix A: Characterization of triacylglycerol composition of sardine oil by using chromatographic techniques ..........................................................................................................................195 Appendix B: Analytical methods .............................................................................................................217 REFERENCES ...................................................................................................................239 SUMMARY / RESUMEN Summary SUMMARY OF THE THESIS Production of omega-3 polyunsaturated fatty acids (n-3 PUFA) concentrates is of great interest for both the pharmaceutical and the food industries. It is well known that the main n-3 PUFA, eicosapentaenoic (EPA) and docosahexaenoic (DHA) acids, have beneficial effects on the prevention and reduction of cardiovascular and inflammatory diseases. However, not all the chemical forms of n-3 PUFA are equal. The bioavailability and susceptibility to oxidation of n-3 PUFA concentrates depend on their molecular structure. Monoacylglycerides and diacylglycerides (MAG and DAG) containing n-3 PUFA present good bioavailability and oxidation stability. Moreover, they present excellent emulsifying properties, being widely used in the food, cosmetic and pharmaceutical industries. Taking into account these considerations and the advantages of enzymatic technology in the formation of this kind of products, this Thesis is focused on the production of MAG rich in n-3 PUFA by a lipase-catalyzed glycerolysis reaction in different reaction systems. The main drawback of this process is the immiscibility of the substrates, therefore the main challenge of this thesis is the evaluation of different possibilities to improve the contact between sardine oil and glycerol to achieve high yields of the reaction products. The use of tert-alcohols, surfactants, supercritical CO2 and a substrate emulsification process are the different alternatives studied in this thesis to carry out the lipase-catalyzed glycerolysis. The effect of different operating variables such as type of lipase, lipase loading, temperature and substrate mole ratio on the kinetic parameters was investigated in the different reaction systems. In addition to the study of the lipase-catalyzed glycerolysis reaction, in this PhD Thesis a molecular distillation process to fractionate the reaction products and concentrate the MAG rich in n-3 PUFA has been optimized. Different evaporation temperatures were evaluated to maximize the MAG recovery at high purity in the distillate product. In the final part of this work, the lipid oxidation of sardine oil and reaction products has been evaluated. In this sense, immobilized commercial lipases have showed good adsorption capacity of the oxidation products formed during the glycerolysis reaction. 3 Resumen RESUMEN DE LA TESIS La producción de concentrados de ácidos grasos poliinsaturados omega 3 (AGPI n-3) continúa
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