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Biotechnological Production of Rosmarinic Acid and Ruscogenins

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Biotechnological Production of Rosmarinic Acid and Ruscogenins Biotechnological production of rosmarinic acid and ruscogenins. Scaling up the optimized processes to benchtop bioreactors Abbas Khojasteh ADVERTIMENT. La consulta d’aquesta tesi queda condicionada a l’acceptació de les següents condicions d'ús: La difusió d’aquesta tesi per mitjà del servei TDX (www.tdx.cat) i a través del Dipòsit Digital de la UB (diposit.ub.edu) ha estat autoritzada pels titulars dels drets de propietat intelꞏlectual únicament per a usos privats emmarcats en activitats d’investigació i docència. No s’autoritza la seva reproducció amb finalitats de lucre ni la seva difusió i posada a disposició des d’un lloc aliè al servei TDX ni al Dipòsit Digital de la UB. No s’autoritza la presentació del seu contingut en una finestra o marc aliè a TDX o al Dipòsit Digital de la UB (framing). Aquesta reserva de drets afecta tant al resum de presentació de la tesi com als seus continguts. En la utilització o cita de parts de la tesi és obligat indicar el nom de la persona autora. ADVERTENCIA. La consulta de esta tesis queda condicionada a la aceptación de las siguientes condiciones de uso: La difusión de esta tesis por medio del servicio TDR (www.tdx.cat) y a través del Repositorio Digital de la UB (diposit.ub.edu) ha sido autorizada por los titulares de los derechos de propiedad intelectual únicamente para usos privados enmarcados en actividades de investigación y docencia. No se autoriza su reproducción con finalidades de lucro ni su difusión y puesta a disposición desde un sitio ajeno al servicio TDR o al Repositorio Digital de la UB. No se autoriza la presentación de su contenido en una ventana o marco ajeno a TDR o al Repositorio Digital de la UB (framing). Esta reserva de derechos afecta tanto al resumen de presentación de la tesis como a sus contenidos. En la utilización o cita de partes de la tesis es obligado indicar el nombre de la persona autora. WARNING. On having consulted this thesis you’re accepting the following use conditions: Spreading this thesis by the TDX (www.tdx.cat) service and by the UB Digital Repository (diposit.ub.edu) has been authorized by the titular of the intellectual property rights only for private uses placed in investigation and teaching activities. Reproduction with lucrative aims is not authorized nor its spreading and availability from a site foreign to the TDX service or to the UB Digital Repository. Introducing its content in a window or frame foreign to the TDX service or to the UB Digital Repository is not authorized (framing). Those rights affect to the presentation summary of the thesis as well as to its contents. In the using or citation of parts of the thesis it’s obliged to indicate the name of the author. FACULTAT DE FARMACIA I CIENCIES DE L’ALIMENTACIÓ BIOTECHNOLOGICAL PRODUCTION OF ROSMARINIC ACID AND RUSCOGENINS . SCALING UP THE OPTIMIZED PROCESSES TO BENCHTOP BIOREACTORS ABBAS KHOJASTEH 2019 UNIVERSITAT DE BARCELONA FACULTAT DE FARMACIA I CIENCIES DE L’ALIMENTACIÓ DOCTORADO EN BIOTECNOLOGIA BIOTECHNOLOGICAL PRODUCTION OF ROSMARINIC ACID AND RUSCOGENINS. SCALING-UP THE OPTIMIZED PROCESSES TO BENCHTOP BIOREACTORS Memoria presentada por Abbas Khojasteh para optar al título de doctor por la Universidad de Barcelona Dr. Javier Palazón Dra. Regine Eibl Director Directora Abbas Khojasteh Doctorando Abbas Khojasteh 2019 Dedication To the human brain Acknowledgements: I want to express my deepest gratitude to: The Ministerio Español de Ciencia e Innovación and FEDER, projects BIO2014- 51861-R and BIO2017-82374-R, for the financial support for the research performed in the University of Barcelona. My supervisors, Professors Javier Palazon from the University of Barcelona and Professor Regine Eibl from the ZHAW School of Life Sciences and Facility Management. The members of the Laboratory of Plant Physiology of the Faculty of Pharmacy of the University of Barcelona and especially Professor Rosa M. Cusidó, Dr. Mercedes Bonfill and Dr. Elisabeth Moyano. Dr. Metón from the Laboratory of Biochemistry of the Faculty of Pharmacy and the professor responsible of the cancer bioassays. My labmates in Wädenswill and Barcelona. My family in Iran and my friends in Switzerland, Spain, USA and Iran. To all the people who have contributed in one way or another to achieve this great goal. Keywords: • Caspases • Ciclodextrines • Coronatine • HepG2 cancer cell line • MCF-7 cancer cell line • Methyl jasmonate • Neoruscogenin • Plant cell cultures • Root-rhizome cultures • Rosmarinic acid • Ruscogenin • Ruscus aculeatus • Satureja khuzistanica Abstract ____________________________________________________________________________________ Abstract: Rosmarinic acid (RA), an ester of caffeic acid and 3,4-dihydroxyphenyl lactic acid, is widely distributed in the plant kingdom, including Satureja khuzistanica , a threatened Iranian plant species. Interest in RA is growing due to its biological activities, including cognitive-enhancing effects, slowing the development of Alzheimer’s disease, cancer chemoprotection and anti-inflammatory activity. In order to meet the increasing demand for this compound and preserve its natural sources, a new biotechnological platform based on cell suspension cultures of S. khuzistanica was developed. The results show that cell suspensions of this plant species synthesized high amounts of RA, which accumulated mainly inside the cells. In order to improve the system’s biotechnological production, the effect of three elicitors, methyl jasmonate (MeJA), cyclodextrin (CD) and coronatine (COR) were tested. The obtained results demonstrate the effectiveness of MeJA and COR in improving the RA production of the S. khuzistanica cell cultures and also that the time course of growth and RA production can change with the age of the cell line and the number of subcultures. In contrast, the effects of CD were found to be insignificant. In this pipeline, the scale up of the biotechnological system to a benchtop bioreactor demonstrated the adaptability of the S. khuzistanica cell cultures to the scaling-up process and that the elicitors MeJA and COR also effectively improved the production at bioreactor level. Concerning the biological activity of S. khuzistanica , we demonstrated that an enriched RA extract was able to reduce the viability of cancer cell lines, increasing the sub-G0/G1 cell population and the activity of caspase-8 in MCF-7 cells, which suggests that S. khuzistanica extracts can induce apoptosis of MCF-7 cells through activation of the extrinsic pathway. In addition, our findings indicate that other compounds of the extract may act synergistically to potentiate the anticancer activity of RA. Similarly to S. khuzistanica , Ruscus aculeatus is a threatened medicinal plant. Its main bioactive components, the steroid saponins ruscogenin and neoruscogenin, have long been used in the treatment of hemorrhoids and varicose veins, but recently demonstrated activity against some types of cancer have stimulated interest in R. aculeatus extracts. Thus, plant cell biofactories could constitute an alternative to the whole plant as a source of these bioactive compounds. In our work, despite the in vitro recalcitrance of R. aculeatus , after many attempts in which we tested more than 70 different culture media, we developed friable R. aculeatus calli and their derived plant cell suspensions. Their ruscognenin production was compared with that of organized in i Abstract ____________________________________________________________________________________ vitro plantlet and root-rhizome cultures. Root-rhizomes showed a higher capacity for biomass and ruscogenin production than the cell suspensions and the yields were greatly improved by elicitation with COR, as in other plant in vitro cultures. The final total ruscogenin content was higher than 1.8 mg g DW -1, after 4 weeks of culture. Although ruscogenins accumulate in plants mainly in the root-rhizome, it was demonstrated that the aerial part could play an important role in their biosynthesis, because production was higher in the whole plant than in the root-rhizome cultures. The most productive biotechnological system, COR-elicited root rhizome cultures, was scaled up to a benchtop bioreactor without losing its capacity for biomass and ruscogenin production. ii Abstract ____________________________________________________________________________________ Resumen: El ácido rosmarínico (RA), un éster del ácido caféico y el ácido 3,4-dihidroxifenil-láctico, se distribuye ampliamente en el reino vegetal, incluida Satureja khuzistanica , una especie vegetal iraní amenazada. El interés por el RA está incrementando actualmente debido a sus actividades biológicas, incluidos los efectos de mejora cognitiva y la desaceleración del desarrollo de la enfermedad de Alzheimer, quimioprotección del cáncer y su actividad antiinflamatoria, entre otros. Con el fin de satisfacer la creciente demanda de este compuesto y preservar sus fuentes naturales, se ha desarrollado una nueva plataforma biotecnológica basada en cultivos de células en suspensión de S. khuzistanica . Los resultados muestran que las suspensiones celulares de esta especie vegetal sintetizan altas cantidades de RA, que se acumula principalmente en el interior de las células. Para mejorar la producción biotecnológica del sistema, se probó el efecto de tres elicitores, jasmonato de metilo (MeJA), ciclodextrina (CD) y coronatina (COR). Los resultados obtenidos demostraron la efectividad de MeJA y COR para incrementar la producción de RA de los cultivos celulares de S. khuzistanica y también
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