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Dissertation DISSERTATION Titel der Dissertation Exudate flavonoids in Primulaceae: comparative studies of chemodiversity aspects Verfasserin Mag. rer. nat. Tshering Doma Bhutia angestrebter akademischer Grad Doktorin der Naturwissenschaften (Dr. rer. nat.) Wien, 2013 Studienkennzahl lt. Studienblatt: A 091 438 Dissertationsgebiet lt. Studienblatt: Botanik Betreuerin / Betreuer: Ao. Univ. Prof. Dr. Karin Valant-Vetschera Acknowledgements It is my great pleasure to thank all those who, with their help and support, have contributed to the completion of this thesis. First and foremost I would like to express my sincere and heartfelt gratitute to my supervisor Assoc. Prof. Dr. Karin Valant‐Vetschera for giving me the opportunity to join the “Chemodiversity Group”. I thank her for assuming the dual role of supervisor and mentor. During the years of my diploma and doctoral theses she has continuously offered me the best guidance, support and advice I could have asked for. I am very grateful to Dr. Lothar Brecker for the characterization and identification of the isolated compounds. Additionally, I thank him for his constant encouragement, support and valuable suggestions. In the lab I have always received invaluable technical support from Mag. Johann Schinnerl, for which I extend him my earnest thanks and appreciation. Prof. Dr. Harald Greger has been very kind and supportive throughout the years, which I gratefully appreciate. Thanks are also due to Prof. Dr. Irene Lichtscheidl and Dr. Wolfram Adlassnig for providing access to their laboratory equipment and for their excellent guidance. I am deeply indebted to Prof. Eckhard Wollenweber (Institut für Botanik der TU Darmstadt, Germany) for the constant supply of authentic flavonoid samples, which made my lab life a lot easier. i Adriane, Andrea, Andreas, Birgit, Celine, Christian, David, Flo, Grace, Markus, Rupi, Sigi, Sonja and Stefan: Thank you all for the wonderful company and nice time in the lab. I have not only enjoyed working with you but also relished the leasure time, barbecues and Christmas parties and will forever cherish these moments. Thanks to Grace for her joyful company and the uncountable laughs we shared while working in the lab. She could always bring a smile on my face. I adore Mata for her kind and selfless nature and for her warm spirit. Thank you for being my friends. I thank my “lunch friends” Anne‐Caroline, Diego, Eva, Grace, Jalil, Khatere, Mata and Tae‐ Soo for the wonderful (and funny) discussions on the fifth floor, which I always looked forward to with joy. Additional thanks to Jalil for giving me the permission to use his beautiful Dionysia pictures. I would like to thank my dear friends in Austria and around the world for making my life enjoyable. I thank them for their understanding, for being there for me whenever I needed them, and for the confidence and strength they gave me. My genuine thanks go to my family for being my energy, confidence and balance. Their love, affection, faith and patience have carried me through my life and educational journeys. I thank my little niece Woeser Doma for being my sunshine. My special and deepest thanks go to my husband Thomas, for always being so caring and supportive. I thank you for making my life beautiful! Finally, I gratefully acknowledge the financial support for part of this doctoral thesis by the "Hochschuljubiläumsstiftung der Stadt Wien" and the "Gesellschaft zur Förderung der Pflanzenwissenschaften". ii Table of contents Abstract ................................................................................................................................................ 1 Zusammenfassung ............................................................................................................................... 2 Co‐Authorship Statement ................................................................................................................... 3 Introduction ......................................................................................................................................... 4 Secondary metabolites (SM) .............................................................................................................. 4 Flavonoids ................................................................................................................................. 4 Exudate flavonoids and glandular trichomes ............................................................................ 7 Model Systems ..................................................................................................................................... 8 Primula ..................................................................................................................................... 8 Dionysia .................................................................................................................................... 9 Aims and outline of the thesis .......................................................................................................... 12 References .......................................................................................................................................... 14 Chapter 1: Exudate flavonoids of Primula spp.: Structural and biogenetic chemodiversity ...... 24 Chapter 2: Chemodiversity of exudate flavonoids in Dionysia (Primulaceae): a comparative study ................................................................................................................................................... 42 Chapter 3: Unusual compounds from exudates of Dionysia diapensifolia and D. gaubae var. megalantha (Primulaceae) ............................................................................................................... 76 Chapter 4: Diversification of exudate flavonoid profiles in further Primula spp. ........................ 91 Chapter 5: Flavonoids in selected Primula spp.: Bridging micromorphology with chemodiversity ................................................................................................................................ 103 Chapter 6: Antifungal orphan flavonoids and dihydrochalcones from Primula exudates ........ 125 General Conclusion and Perspectives ............................................................................................ 146 Curriculum Vitae ............................................................................................................................. 148 iii Abstract Exudate flavonoids can be defined as secondary metabolites that are accumulated on aerial surfaces of plants, as a result of excretions associated with the presence of glandular trichomes. Exudate flavonoids are common on alpine plants such as Primula L. and Dionysia Fenzl., two plant genera dealt with in this thesis. These genera are closely related and their distinction on the generic level is a subject of debate. According to the newest molecular results Dionysia should be placed within Primula sensu lato. One of the characters of Primula and Dionysia that catches the eye is the production of mealy or woolly farina. Oily excretions are just as common but not relevant as a character. These excretions, whether mealy, woolly or oily, consist of aberrant flavonoids such as unsubstituted flavone, 2'‐OH‐flavone, 3',4'‐diOH‐flavone and 8,2'‐diOH‐flavone, which vary from the usual flavonoids regarding their substitution pattern and are hence assumed to follow a different and yet unknown biosynthetic pathway. Dionysia, however, also exhibits flavonoids in its exudates that arise from the regular biosynthetic pathway. This thesis aims at isolation and identification of exudate flavonoids of these two genera and comparison of their chemosystematics on the behalf of exudate flavonoids. The isolated compounds are further tested for their antifungal properties. Chapters one, four, five and six mainly focus on exudates of Primula and discuss their chemodiversity. In chapter five micromorphology is combined with glandular trichome chemistry to study the localization of exudate flavonoids. Chapters two and three on the other hand deal with Dionysia and its relationship with Primula. 1 Zusammenfassung Als Exkretflavonoide kann man jene Sekundärmetabolite bezeichnen, die mittels Drüsenhaare auf der Oberfläche oberirdischer Pflanzenteile akkumuliert werden. Exkretflavonoide kommen häufig bei alpinen Pflanzen vor, wie z.B. Primula L. und Dionysia Fenzl, den beiden in dieser Arbeit behandelten Pflanzengattungen. Letztere sind eng verwandt und ihre Unterscheidung auf Gattungsebene bleibt umstritten. Nach neuesten molekularen Ergebnissen sollte Dionysia innerhalb Primula sensu lato platziert werden. Zu den augenfälligsten Eigenschaften von Primula und Dionysia gehört die Produktion von mehligem oder wolligem Belag. Ölige Exsudate sind ebenso häufig, aber nicht relevant als Merkmal. Diese mehligen, wolligen oder öligen Exsudate bestehen aus aberranten Flavonoiden wie unsubstituiertes Flavon, 2'‐OH‐Flavon, 3',4'‐diOH‐Flavon und 8,2'‐diOH‐ Flavon. Diese unterscheiden sich hinsichtlich ihrer Substitutionsmuster von üblichen Flavonoiden, weshalb davon ausgegangen wird, dass ihre Entstehung auf einem anderen und noch unbekannten Biosyntheseweg erfolgt. Die Gattung Dionysia weist jedoch auch Flavonoide in ihren Exsudaten auf, die aus dem regulären Biosyntheseweg entstehen. Die vorliegende Dissertation hat das Ziel, Exkretflavonoide dieser beiden Gattungen zu isolieren und identifizieren, und auf dieser Grundlage ihre Chemosystematik zu vergleichen.
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