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Distribution and Metabolism of Constituents and Metabolites of a Standardized Maritime Pine Bark Extract (Pycnogenol®) in Human

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Distribution and Metabolism of Constituents and Metabolites of a Standardized Maritime Pine Bark Extract (Pycnogenol®) in Human Distribution and metabolism of constituents and metabolites of a standardized maritime pine bark extract (Pycnogenol®) in human serum, blood cells and synovial fluid of patients with severe osteoarthritis DISSERTATION zur Erlangung des naturwissenschaftlichen Doktorgrades der Julius-Maximilians-Universität Würzburg vorgelegt von Melanie Mülek aus Aschaffenburg Würzburg 2015 Eingereicht bei der Fakultät für Chemie und Pharmazie am: ……………………............. Gutachter der schriftlichen Arbeit: 1. Gutachter ……………………............. 2. Gutachter ……………………............. Prüfer des öffentlichen Promotionskolloquiums: 1. Prüfer ……………………............. 2. Prüfer ……………………............. 3. Prüfer ……………………............. Datum des öffentlichen Promotionskolloquiums: ……………………............. Doktorurkunde ausgehändigt am: ……………………............. Die vorliegende Arbeit wurde auf Anregung und unter Anleitung von Frau Prof. Dr. Petra Högger am Lehrstuhl für Pharmazeutische Chemie des Instituts für Pharmazie und Lebensmittelchemie der Julius-Maximilians-Universität Würzburg angefertigt. PAPERS INCLUDED IN THIS THESIS This thesis is divided into five publications, which are referred to in the text by their numbers 1-5. 1 Facilitated uptake of a bioactive metabolite of maritime pine bark extract (Pycnogenol) into human erythrocytes Kurlbaum, M., Mülek, M. and Högger P. PLoS One, 2013. 8: e63197 DOI: 10.1371/journal.pone.0063197 2 Highly sensitive analysis of polyphenols and their metabolites in human blood cells using dispersive SPE extraction and LC-MS/MS Mülek, M. and Högger, P. Anal Bioanal Chem, 2015. 407: 1885-1899 DOI 10.1007/s00216-014-8451-y 3 Profiling a gut microbiota-generated catechin metabolite’s fate in human blood cells using a metabolomic approach Mülek, M., Fekete, A., Wiest, J., Holzgrabe, U., Mueller, MJ. and Högger, P. J Pharm Biomed Anal, 2015. 114: 71-81 DOI: 10.1016/j.jpba.2015.04.042 4 Development of LC-ESI/MS/MS methods for quantification of polyphenols in human plasma and serum with particular consideration of matrix effects Mülek, M. and Högger, P. in preparation (unpublished) 5 Distribution of constituents and metabolites of maritime pine bark extract (Pycnogenol®) into serum, blood cells and synovial fluid of patients with severe osteoarthritis Mülek, M., Seefried, L., Genest, F. and Högger, P. in preparation (unpublished) CONFERENCE CONTRIBUTIONS Poster Presentations The importance of matrix effect investigations in human biological matrices for accurate and sensitive quantification of polyphenols with LC-ESI/MS/MS Mülek, M. and Högger, P. 20th International Mass Spectrometry Conference (IMSC), August 24-29, 2014, Geneva, Switzerland Sensitive quantification of selected polyphenols and drugs in human complex biological matrices with LC-ESI/MS/MS Mülek, M., Scherf-Clavel, M. and Högger P. Chemie Symposium der Studierenden Mainfrankens (ChemSystm), December 02, 2014, Würzburg, Germany Awards Travel grant from the International Mass Spectrometry Foundation (IMSF) for attending 20th International Mass Spectrometry Conference (IMSC), August 24-29, 2014, Geneva, Switzerland DANKSAGUNG Mein besonderer Dank gehört denjenigen Personen, die mich auf vielfältigste Weise bei der Durchführung und erfolgreichen Fertigstellung dieser Arbeit unterstützt haben: Ich möchte allen voran Frau Prof. Dr. Petra Högger für die freundliche Aufnahme in Ihren Arbeitskreis, die interessanten und motivierenden Gespräche sowie für das stets in mich gesetzte Vertrauen bedanken. Vielen Dank für Ihre Unterstützung und Hilfe in jeder Phase der Erstellung dieser Dissertationsarbeit. Auch für das entgegengebrachte Vetrauen im Rahmen der Lehrtätigkeit und Studentenbetreuung im Fach Biochemie und klinische Chemie möchte ich mich ganz herzlich bedanken. Mein großer Dank gilt den Ärzten und Mitarbeitern der Orthopädischen Klinik König-Ludwig Haus, Würzburg, für die erfolgreiche Kooperation bei der Durchführung der Osteoarthritis Studie. Hier möchte ich insbesondere Herrn Dr. Lothar Seefried, Jasmin Baumann und Ursula Hellwich für Ihren stets tatkräftigen Einsatz und für Ihre Unterstützung danken. Ich möchte auch allen Patienten ein „Danke“ schenken, die dazu bereit waren, an den Tagen vor den Blutentnahmen Ihre Ernährungsgewohnheiten umzustellen und alle entnommenen Proben zu Forschungszwecken zur Verfügung zu stellen. Bei Herrn Dr. Bruno Pasurka und den fleißigen Helfern seiner Arztpraxis sowie bei Herrn Prof. Dr. Bernd Engels möchte ich mich recht herzlich für das Sammeln von Gelenkflüssigkeitsproben bedanken. In diesem Zusammenhang möchte ich mich auch bei allen „Freiwilligen“ bedanken, welche den Kiefernrindenextrakt eingenommen haben um mir anschließend Blutproben für analytische Zwecke zur Verfügung stellen zu können. Dies war sehr hilfreich für meine Untersuchungen. Bei Herrn Prof. Fritz Sörgel, Leiter des Instituts für Biomedizinische und Pharmazeutische Forschung (IBMP), möchte ich mich besonders für die Möglichkeit bedanken, meine ersten Erfahrungen an Tandem-Massenspektrometrie mit Hilfe seines sehr kompetenten Teams zu sammeln. Ein großes Dankeschön geht hier an Frau Dr. Martina Kinzig und an Christoph Stelzer. In diesem Zusammenhang möchte ich mich auch bei Herrn Dr. Frank Heckel und seinem Team der Tetra Holdings GmbH, Stuttgart, bedanken. Vielen lieben Dank für Eure zahlreichen und motivierenden Diskussionen und für die guten Ratschläge. Das mit Eurer Hilfe aufgebaute Wissen war für meine späteren eigenen Projekte am institutseigenen Gerät sehr wertvoll. Herrn Prof. Dr. Martin J. Müller und Frau Dr. Agnes Fekete aus der Pharmazeutischen Biologie, Würzburg, möchte ich ein großes Dankeschön schenken für die Kooperation bezüglich des sekundären M1-Metabolismus. Vielen lieben Dank, Agi, für Deinen stets unermüdlichen Einsatz und Deiner Hilfe bei der Interpretion der qTOF-Messungen, den zahlreichen wissenschaftlichen Diskussionen, aber auch für die lustigen Sushi-Abende. Bei Dr. Johannes Wiest möchte ich mich recht herzlich für die NMR-Aufnahme des M1-Glutathion Addukts und auch für die Interpretation und Diskussion diesbezüglich bedanken. Einen großen Dank möchte ich ebenso an Frau Prof. Dr. Ulrike Holzgrabe aussprechen, ohne Ihre enorme Unterstützung wäre es nicht möglich gewesen, meine LC-MS/MS Messungen am Institut erfolgreich zu beenden. Vielen Dank für Ihr Vertrauen, dass Sie mir bei der Geräteverantwortung entgegen gebracht haben. In diesem Zusammenhang möchte ich mich auch bei Herrn Dr. Bernd Reyer bedanken. Vielen lieben Dank, Bernd, für Deine stets geduldige Unterstützung und für Dein Engagement bei allen Angelegenheiten rund um Hard- und Software. Bei Frau Dr. Petra Kapková möchte ich mich für die Einweisung am LC-MS/MS System bedanken. Ich möchte mich auch noch bei Frau Ebner und Frau Möhler für Ihre große Hilfsbereitschaft und die stets angenehmen Gespräche bedanken. Ein großes Dank und Lob geht an die Mitarbeiter der institutseigenen Werkstatt, Georg Walter, Matthias Völker, Karl Vollmuth, und den Auszubildenden, welche mich durch Ihre Hilfe in den letzten Jahren sehr unterstützt haben. Der Firma Horphag Research, Hersteller von Pycnogenol®, möchte ich für die finanzielle Unterstützung danken. Den ehemaligen und aktuellen Mitgliedern des Arbeitskreises, Dr. Beatrice Trammer, Dr. Max Kurlbaum, Dr. Klaus Uhlenhut, Dr. Frederic Vollmers, Martin Haas, Lisa Schaaf, Steffen Jeßberger, Maike Scherf-Clavel, Stoyan Dirimanov, Andreas Pospiech, Linda Volpp, Roswitha Scheblein sowie Dr. Jianbo Xiao und Hui Ciao danke ich für die stets angenehme Arbeitsatmosphäre. Vielen lieben Dank, Martin, für unsere zahlreichen Laborgespräche und analytische Diskussionen, aber auch für die schönen (Tanz-)Abende. Steffen, bei Dir möchte ich mich für die gute Zusammenarbeit innerhalb der Studie bedanken. Wir waren ein echt gutes Team und das gemeinsame „Verarbeiten“ der Probandenproben bleibt mir noch heute in Erinnerung. Meinen allergrößten Dank möchte ich Dir, Maike, schenken. Dein Zugang in unseren Arbeitskreis hat meine restliche Zeit der Promotion wesentlich bereichert. Nicht nur, dass wir uns in wissenschaftlicher und analytischer Hinsicht stets kompromisslos unterstützt haben, sondern auch privat ging es weit über den Unialltag hinaus. Danke Dir für die großartige Zeit, unsere vielen gemeinsamen Aktivitäten und Ausflüge, unsere gemeinsamen Spinning-/Sport- und Kochabende, aber auch für Deine Unterstützung und Hilfe in sämtlichen Lebenslagen. Ich vermisse jetzt schon die schöne gemeinsame Zeit in Würzburg und denke oft an einige unvergessliche Momente zurück. Herrn Dr. Anagnostis Valotis danke ich für die vielen wissenschaftliche Gespräche und den stets abwechslungsreichen Besuchen im Labor. Noti, ich möchte Dir für Deine überdurchschnittliche Hilfsbereitschaft danken, die Du mir jederzeit geschenkt hast. Bei den Assistenten des Praktikums des 5. Semesters, Diana, Daniel, Klaus, Fredi, Steffi, Maike, David, Daniela und Stoyan möchte ich mich für die gute Zusammenarbeit während der Studentenbetreuung bedanken. Die lustigen Essensabende und Weinverkostungen werden mir noch lange in freudiger Erinnerung bleiben. Steffi, danke Dir für die super Stimmung während unserer gemeinsamen Aufsicht, aber auch für die vielen motivierenden Diskussionen und Deine Hilfe im MS-Raum. László Tölgyesi möchte ich für das aufmerksame Korrekturlesen, die Unterstützung und auch für die stetige Bereitschaft für analytische Diskussionen danken. Birgit, Werner und Marie Schober, Euch danke ich für Eure stetige Herzlichkeit, Eure motivierenden Zusprüche und für die schöne gemeinsame Zeit. Danke,
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