Identification and functional characterization of the first two aromatic prenyltransferases implicated in the biosynthesis of furanocoumarins and prenylated coumarins in two plant families: Rutaceae and Apiaceae Fazeelat Karamat To cite this version: Fazeelat Karamat. Identification and functional characterization of the first two aromatic prenyl- transferases implicated in the biosynthesis of furanocoumarins and prenylated coumarins in two plant families: Rutaceae and Apiaceae. Agronomy. Université de Lorraine, 2013. English. NNT : 2013LORR0029. tel-01749560 HAL Id: tel-01749560 https://hal.univ-lorraine.fr/tel-01749560 Submitted on 29 Mar 2018 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. AVERTISSEMENT Ce document est le fruit d'un long travail approuvé par le jury de soutenance et mis à disposition de l'ensemble de la communauté universitaire élargie. Il est soumis à la propriété intellectuelle de l'auteur. Ceci implique une obligation de citation et de référencement lors de l’utilisation de ce document. D'autre part, toute contrefaçon, plagiat, reproduction illicite encourt une poursuite pénale. Contact : [email protected] LIENS Code de la Propriété Intellectuelle. articles L 122. 4 Code de la Propriété Intellectuelle. articles L 335.2- L 335.10 http://www.cfcopies.com/V2/leg/leg_droi.php http://www.culture.gouv.fr/culture/infos-pratiques/droits/protection.htm UNIVERSITE DE LORRAINE Ecole doctorale Sciences et Ingénierie des Ressources, Procédés, Produits, Environnement THESE Présentée et soutenue publiquement pour l’obtention du titre de Docteur de l’Université de Lorraine Mention « Sciences Agronomiques » par Fazeelat KARAMAT Identification and functional characterization of the first two aromatic prenyltransferases implicated in the biosynthesis of furanocoumarins and prenylated coumarins in two plant families: Rutaceae and Apiaceae Soutenue publiquement le 21 mai 2013 Membres du jury: Rapporteurs : Mme Nathalie Guivarc'h Professeur, Université François-Rabelais de Tours, Tours M. Bilal Camara Professeur, Université de Strasbourg, Strasbourg Examinateurs : M. Laurent Legendre Professeur, Université Jean Monnet de Saint Etienne, Saint-Etienne M. Alexandre OLRY Ingénieur de Recherche, Université de Lorraine M. Frédéric BOURGAUD Professeur, Université de Lorraine M. Alain HEHN Maître de conférences, Université de Lorraine UMR1121 Université de Lorraine - INRA, Laboratoire Agronomie et Environnement, 2 avenue Forêt de Haye TSA 40602, 54518 - VANDOEUVRE CEDEX Dedicated to my beloved mother Aknowledgement First of all to I would like to thank Higher Education Commission (HEC) of Pakistan for giving me this opportunity of studying abroad and supporting my Doctorate studies which were carried out in the laboratory “Laboratoire d’Agronomie et Environnement” (LAE), under the supervision of Dr. Alain Hehn and the co-supervision of Pr. Frederic Bourgaud and Dr. Alexandre Olry. I would like to mention with high gratitude that the overseas scholarship scheme of HEC Pakistan has proved to be a marvelous initiative for bringing well-deserved opportunities to the youth of Pakistan. I strongly look forward that this study of mine shall contribute its fair part to explore new research avenues and strengthen HEC’s efforts for a better human resource development in Pakistan with a strong support from friendly countries like France. I would like to thank Pr. Frederic Bourgaud, for allowing me to continue in his laboratory after masters and providing me an opportunity to work with his team. I am also thankful to his fruitful deeds and suggestions he provided to improve my research project. I am very grateful to my supervisor, Dr. Alain Hehn, for accepting me to work with him, for his supervision, his understanding, his support, his confidence in me and his precious time throughout my thesis. His optimism, his punctuality, his joy of life, his kind heartedness, his scientific approach, and his hardworking attitude will always guide me throughout my professional as well as my personal life. The energy he transmitted to me while working with me will always serve as the fuel for my future endeavors. Merci Alain. I am also thankful to Dr. Alexander Olry for his very kind co-supervision. I really cherish each and every moment I passed in his company. I feel that I was very lucky to have a chance to work with “Alex” for such a long time. I really appreciate his style of work, his attitude towards others and above all his intelligence. I always liked his attitudes to tackle the scientific problems and still grateful to him for providing me the suggestions and help that unblocked me and my experimental work several times during my thesis. I would like to thanks all the members of jury; Mme Nathalie Guivarc'h, Mr. Bilal Camara and Mr. Laurent Legendre for evaluating this research work. I would like to thank the members of jury of “mindmap sessions” Mr. Christophe Robin, Mr. Sylvain Plantureux, Mr. Frederic Bourgaud, Mr. Alain Hehn and Mr. Alexander Olry to find the time form their busy schedules and to organize these sessions. As these sessions helped me lot to understand my research project very clearly. I am also thankful to M. Romain Larbat for his kind suggestions and positive attitude. I would like to thank my office colleagues also. I am also thankful to Guilhem who helped me a lot in the beginning to understand the things that were complicated because of my in- competency for French language. I am also thankful to Mathilde, Celia and Nicolas for their kindness and positive attitude and to be always available to make things easy for me. I am really and deeply grateful to the persons of PAT SAS for their kind attitudes. I appreciate the nice and friendly nature of Benoit. I would like to thanks, especially Sissi, Estelle, Flore and Cindy for their friendly and unconditional helping attitudes for me to sort out the problems. I would like thanks to my pakistani colleagues present with in France. I will always appreciate and remember the supporting attitude of Maira that helped me a lot in the beginning to settle in Nancy. Your “petit genie” is a magic and is really helpful for me also to come out stressed conditions. Thank you very much Sandly, for doing everything for me. I will always remember the tours that we made together here to explore things. I want to say a lot of thanks to Samina, Zeeshan, Abdur Rahman, Farhan for providing your company and making a small family here in France. I am also thankful to Faiza Zaidan who helped me a lot to make the final version of thesis. I am also thankful to my family, Abu ji, Aoun, Aroob, Asim, Qasim, Farwa and Ali for helping me to reach up to this stage of life. Bundles of thanks for your love, unconditional availability, and prayers which were always with me. I would also thanks to my in laws family who were more than supportive in all this time of my studies. And at the end, I am really so deeply thankful to my husband, Wasif Ali who always supported me during tough times. I would like to say it was never ever possible without your support that I can make up this goal of life. I could never forget your patience and will always be thankful to you for all your efforts, love, sincerity, confidence, you provided me time to time during my Ph.D. Love you….!!! Table of contents Aknowledgement ....................................................................................................................... 5 Table of contents ........................................................................................................................ 9 List of figures ........................................................................................................................... 19 List of tables ............................................................................................................................. 25 List of abbreviations ................................................................................................................. 27 List of species cited in the manuscript ..................................................................................... 28 Introduction .............................................................................................................................. 33 1 Phenylpropanoids .............................................................................................................. 33 1.1 Biosynthetic pathway of phenylpropanoids .............................................................. 34 1.2 Coumarins and furanocoumarins ............................................................................... 35 1.2.1 Coumarins .......................................................................................................... 35 1.2.2 Biosynthetic pathway of coumarins ................................................................... 38 1.3 Furanocoumarins ....................................................................................................... 41 1.3.1 Distribution of furanocoumarins in the plant