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Functional Characterization of Prenyltransferases Involved in the Biosynthesis of Polycyclic Polyprenylated Acylphloroglucinols in the Genus Hypericum

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Functional Characterization of Prenyltransferases Involved in the Biosynthesis of Polycyclic Polyprenylated Acylphloroglucinols in the Genus Hypericum Functional characterization of prenyltransferases involved in the biosynthesis of polycyclic polyprenylated acylphloroglucinols in the genus Hypericum Von der Fakultät für Lebenswissenschaften der Technischen Universität Carolo-Wilhelmina zu Braunschweig zur Erlangung des Grades eines Doktors der Naturwissenschaften (Dr. rer. nat.) genehmigte D i s s e r t a t i o n von Mohamed Mamdouh Sayed Nagia aus Kalyobiya/ Ägypten 1. Referent: Professor Dr. Ludger Beerhues 2. Referent: Professor Dr. Alain Tissier eingereicht am: 30.07.2018 mündliche Prüfung (Disputation) am: 15.10.2018 Druckjahr 2018 „Gedruckt mit Unterstützung des Deutschen Akademischen Austauschdienstes“ „Und sag: O mein Herr, mehre mein Wissen“ Der Edle Qur’an [20: 114] Vorveröffentlichungen der Dissertation Teilergebnisse aus dieser Arbeit wurden mit Genehmigung der Fakultät für Lebenswissenschaften, vertreten durch den Mentor der Arbeit, in folgenden Beiträgen vorab veröffentlicht: Publikationen Nagia, M., Gaid, M., Biedermann, E., Fiesel, T., El-Awaad, I., Haensch, R., Wittstock, U., and Beerhues, L. Sequential regiospecific gem-diprenylation of tetrahydroxyxanthone by prenyltransferases from Hypericum sp. (Submitted). Nagia, M., Gaid, M., Beuerle, T., and Beerhues, L. Successive xanthone prenylation in Hypericum sampsonii. Planta Medica International Open 4, Tu-SL-01 (2017). doi: 10.1055/s-0037-1608308 Tagungsbeiträge A. Vorträge Nagia M., Gaid M., Biedermann E., Beuerle T., Beerhues L., Successive xanthone prenylation in Hypericum sampsonii, 65th Annual Meeting of the Society for Medicinal Plant and Natural Product Research, Basel, Switzerland, 3. – 7. September 2017. Nagia M., Gaid M., Behrends S., Beerhues L., Novel PPAP-related prenyltransferases, 4. SynFoBiA -Kolloquium des Pharmaverfahrenstechnik (PVZ), Braunschweig, Germany, 26. February 2016. Nagia M., Gaid M., Beurele T., Biedermann E., Beerhues L., Aromatic Prenyltransferases from Hypericum sampsonii, Postgraduate workshop of the section „Natural Products“ German Society for Plant Sciences (DBG), Meisdorf, Germany , 11. – 13. September 2016. Nagia M., Gaid M., Biedermann E., Beuerle T., Beerhues L., Aromatic Prenyltransferases from Hypericum sampsonii, 5. SynFoBiA (Neuartige Synthese- und Formulierungsverfahren für schwerlösliche Arzneistoffe und empfindliche Biopharmazeutika) Meeting, Braunschweig, Germany, 10. October 2016 B. Posterbeiträge Nagia M., Gaid M., Bartels J., Beurele T., Behrends S., Beerhues L., Aromatic prenyltransferases from Hypericum sampsonii, Braunschweig International Symposium on Pharmaceutical Engineering Research (SPhERe), Braunschweig, Germany, 19.-20. October 2015. Nagia M., Gaid M., Fiesel T., Beerhues L., Heterologous expression and functional analysis of novel prenyltransferases from the medicinal plant Hypericum sampsonii, 7th International PhD Symposium, organised by the Helmholtz International Graduate School for Infection Research, Braunschweig, Germany, 11. December 2014. ACKNOWLEDGMENT All gratitude to the almighty GOD for the blessings, wellbeing, and giving me the knowledge and patience to complete this work. I would like to express my sincere praise to my supervisor Prof. Dr. Ludger Beerhues for giving me the opportunity to join his workgroup to work on this interesting research point. I immensely thank him also for his patience, motivation, and immense knowledge. He provided the group members with a suitable environment that supports the growth of Creative ideas and Scientific discussions on a friendly-cooperative (FC) medium. His smooth and friendly way of guidance and suggesting creative comments that motivate us to work and overcome the scientific challenges arise during the research work are highly appreciated. I have learned from him how to face the scientific problems in a confident way. Finally, I’d like to thank him also for his pleasant character and for keeping a sense of humor when I had lost mine due to the work stress. I find the German word “Doktorvater” suits him better than the English word “supervisor”. Many thanks for Prof. Dr. Alain Tissier for his interest in this research work, time, and efforts to referee my dissertation. I also appreciate the acceptance of Prof. Dr. Stephan Scherneck to be the chairman of my Ph.D. committee and Prof. Dr. Ute Wittstock as an examiner during the Ph.D. defense. Thanks to Prof. Dr. Robert Hänsch for his support of the localization studies done during the Ph.D. and for Prof. Dr. Sönke Behrends for the co-operation by insect-cells expression. My deep thanks go to Dr. Mariam Gaid for her sincere guidance, scientific support, and caring throughout the course of the practical work and the revision of the thesis. Her maddening attention to details gleam the importance of such a research item and drove me to finally learn to punctuate prose. Constructive discussion held with her, as well as her scientific experience, facilitate the way to beat the challenges facing me and helped me to find solutions to the tricks of biological systems and molecular biology methods during the accomplishment of my Ph.D. I am grateful to Dr. Till Beuerle for supporting me through the analytical work with Mass spectroscopy and GC-MS, his patience to clarify and discuss all aspects belong to these parts. His sarcastic way of dealing with life helped in relieving the work stress. Many thanks to his kind and friendly guidance during my supervision for the undergraduates’ biochemistry courses. I am also thankful to Dr. Rainer Lindigkeit for the technical support and valuable discussions. I’m very thankful to Dr. Islam Elawaad, the first person I have met in Braunschweig, who introduced me to the group. His presence accelerated and facilitated my adaptation in the group. His calm attitude in life equalized my dynamic character. His team spirit, sharing of ideas, and tips helped me going through a lot of obstacles. I thank him also for the work-off times we spent together and the shared cheering memories. Sincere appreciation for my former colleagues Dr. Eline Biedermann for her support by the subcellular localization work done in this study and her pleasant character; and Dr. Tobias Fiesel, who provided me with the primers of prenyltransferases cloned previously from other Hypericum sp. for homology-based cloning of prenyltransferases from my plant H. sampsonii. I’d like to thank my current and former lab mates. Dr. Benye Liu for his welcoming approachable personality, kindness, valuable ideas, and co-operation, Dr. Marco Grull, Ibtisam Ali, Rabeia Ali, Sara Nassar, Philipp Koch, Christian Bunzel and Poonam Singh for the comfortable and friendly atmosphere, valuable and inspiring scientific discussions and continuous encouragement. Special thanks go to Dr. Mina Noshy and Hisham Mohamed for the work-off times I spent with each of them conducting conversations and laughing to get out of the stringent scientific life for some time. Extended Thanks for all members of the working group of Prof. U. Wittstock, I’m really happy to meet you all. Bettina Böttner, Doris Glindemann, and Ines Rahaus are acknowledged for their efforts that aid and support every day’s work of all IPB members. For all departed and present colleagues in IPB, I will always remember our happy and joyful conversations and laughter during events and birthday celebrations. I have learned a lot during my stay at our institute at the personal as well as professional levels. I acknowledge German Academic Exchange Service (DAAD) and the Egyptian Ministry of Higher Education (MOHE) for granting me this scholarship in the frame of the German-Egyptian Research Long-Term Scholarship (GERLS), which expanded and developed my skills, knowledge and scientific experience and made me acquainted with a new culture. From the deep of my heart, I’d like to thank Rania Elmahdy, my beloved wife, who shares with me every moment of success achieved since more than 10 years ago. Her responsibility, moral support, and love during the ups and downs offered me an excellent and productive atmosphere, alleviated the obstacles from my way, and facilitated my life. Further, I made use of her professional comments and advice that enlighten some ideas concerning the work as she was the first auditor of my seminars and talks. She is the most precious gift from the GOD. Many thanks to my dear sons Mazen and Marawan. They were doing always their best to draw the smile on my face with their out of the box ideas and kid’s logic-solutions for every problem. Their little smiling faces remove all the tiredness and stress after a work-full day. There are not enough words to thank and express my sincere appreciation and great indebtedness to my Parents who expected this day more than 30 years ago. I wished that they were with me now to see one more success added to their stock. They provided me with care, trust, affection, everlasting love, and of course prayers. May GOD rest the soul of my father in peace and give my mother a long healthy life. I owe them all the success I achieved in my life. My hearty gratitude to my brother and sister for their encouragement and help at every moment. It is absolutely a happy moment to express those feelings to all family members and colleagues. I hope that the words have transferred those feelings in the right way. To the soul of my father To my mother To Rania, Mazen, and Marawan Contents Table of Contents 1 Introduction ............................................................................................................................. 1 1.1 The genus Hypericum ....................................................................................................
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