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In Vitro Bioactivities of Dietary Anthocyanins and Proanthocyanidins: Implications for Bioavailability, Neuroprotection and Safety

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In Vitro Bioactivities of Dietary Anthocyanins and Proanthocyanidins: Implications for Bioavailability, Neuroprotection and Safety In vitro bioactivities of dietary anthocyanins and proanthocyanidins: implications for bioavailability, neuroprotection and safety Dissertation zur Erlangung des naturwissenschaftlichen Doktorgrades der Julius-Maximilians-Universität Würzburg vorgelegt von Andrea Dreiseitel aus Illertissen Würzburg 2011 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: ……………………………… […] one's title […] says very little about how well one's life has been led -- that no matter how much you've done, or how successful you've been, there's always more to do, always more to learn, and always more to achieve. Barack Obama Danksagung Die vorliegende Arbeit entstand von November 2006 bis Oktober 2009 am Lehrstuhl für Lebensmittelchemie der Universität Würzburg und an der Klinik und Poliklinik für Psychiatrie, Psychosomatik und Psychotherapie der Universität Regensburg unter Anleitung von Prof. Dr. Peter Schreier. An dieser Stelle möchte ich allen Personen herzlich danken, die zum Gelingen dieser Arbeit beigetragen haben, insbesondere bei • Prof. Dr. Peter Schreier für die Vermittlung des interessanten Themas, für sein entgegengebrachtes Vertrauen, für die wertvollen Anregungen und die Möglichkeit die Promotion erfolgreich abzuschließen. • Dr. Philipp Sand für die engagierte Betreuung, für die Freiheiten die er mir überlassen hat, für seine Hilfestellungen, stete Diskussionsbereitschaft und Unterstützung in jeder Hinsicht. • Anett für die Durchführung der LC-MS/MS-Messungen. • beim Bundesministerium für Bildung und Forschung für die finanzielle Unterstützung. • allen beteiligten Projektteilnehmern für die Ratschläge und wertvollen Diskussionen. • der Firma SOLVO Biotechnology für die angenehme Zusammenarbeit. • Gabi für die praktische Einarbeitung in der Anfangsphase. • Martina, Petra, Gabi, Martin und Julia für die moralische Unterstützung, Motivation und die Ablenkung von der Arbeit. Mein größter Dank gilt meinen Eltern, meiner Oma, Marion und Wolfgang, die immer an mich geglaubt haben und für mich da waren, mich ertragen haben wenn ich unausstehlich war, und mich in jeglicher Art und Weise unterstützt haben. Publications Dreiseitel A, Schreier P, Oehme A, Locher S, Rogler G, Piberger H, Hajak G, Sand PG (2008) Inhibition of proteasome activity by anthocyanins and anthocyanidins. Biochem Biophys Res Commun 372(1): 57-61. Dreiseitel A, Schreier P, Oehme A, Locher S, Hajak G, Sand PG (2008) Anthocyanins and their metabolites are weak inhibitors of cytochrome P450 3A4. Mol Nutr Food Res 52(12): 1428-1433. Dreiseitel A, Schreier P, Oehme A, Locher S, Rogler G, Piberger H, Hajak G, Sand PG (2009) Anthocyanins and anthocyanidins are poor inhibitors of CYP2D6. Methods Find Exp Clin Pharmacol 31(1): 3-9. Dreiseitel A, Korte G, Schreier P, Oehme A, Locher S, Domani M, Hajak G, Sand PG (2009) Berry anthocyanins and their aglycons inhibit monoamine oxidases A and B. Pharmacol Res 59(5): 306-311. Dreiseitel A, Korte G, Schreier P, Oehme A, Locher S, Hajak G, Sand PG (2009) sPhospholipase A2 is inhibited by anthocyanidins. J Neural Transm 116(9): 1071-1077. Dreiseitel A, Oosterhuis B, Vukman KV, Schreier P, Oehme A, Locher S, Hajak G, Sand PG (2009) Berry anthocyanins and anthocyanidins exhibit distinct affinities for efflux transporters BCRP and MDR1. Br J Pharmacol 158(8): 1942-1950. Korte G, Dreiseitel A, Schreier P, Oehme A, Locher S, Hajak G, Sand PG (2009) An examination of anthocyanins' and anthocyanidins' affinity for cannabinoid receptors. J Med Food 12(6): 1407-1410. Sand PG, Dreiseitel A, Stang M, Schreier P, Oehme A, Locher S, Hajak G (2010) Cytochrome P450 2C19 inhibitory activity of common berry constituents. Phytother Res 24(2): 304-307. Korte G, Dreiseitel A, Schreier P, Oehme A, Locher S, Geiger S, Heilmann J, Sand PG (2010) Tea catechins’ affinity for human cannabinoid receptors. Phytomedicine 17(1): 19-22. Piberger H, Schreier P, Oehme A, Krammer G, Dreiseitel A, Sand PG, Schoelmerich J, Obermeier F, Rogler G. Bilberries and their anthocyanins ameliorate experimental colitis. In prep. Posters Dreiseitel A, Schreier P, Hajak G, Sand PG, Flavonoid-drug interactions: effects of anthocyanins and anthocyanidins on CYP2D6. 25. Symposium der Arbeitsgemeinschaft für Neuropsychopharmakologie und Pharmakopsychiatrie (AGNP), Munich, October 3 - 6, 2007. Dreiseitel A, Korte G, Schreier P, Hajak G, Sand PG, Proteasom-Hemmung durch Anthocyane als potentieller neuroprotektiver Mechanismus. Kongress der Deutschen Gesellschaft für Psychiatrie, Psychotherapie und Nervenheilkunde (DGPPN), Berlin, November 21 - 24, 2007. Dreiseitel A, Korte G, Schreier P, Hajak G, Sand PG, CYP2D6-Hemmung durch Anthocyane mit Bezug auf den Arzneistoffmetabolismus. Kongress der Deutschen Gesellschaft für Psychiatrie, Psychotherapie und Nervenheilkunde (DGPPN), Berlin, November 21 - 24, 2007. Index I Index ABBREVIATIONS ............................................................................................. V SUMMARY......................................................................................................... X ZUSAMMENFASSUNG.................................................................................. XIII 1 INTRODUCTION ........................................................................................ 1 2 STATE OF KNOWLEDGE.......................................................................... 3 2.1 The family of flavonoids ......................................................................................................... 3 2.2 Stability, bioavailability and metabolism............................................................................ 7 2.2.1 Anthocyanins .......................................................................................................................... 7 2.2.1.1 Anthocyanin stability .................................................................................................... 7 2.2.1.2 Anthocyanin bioavailability and metabolism............................................................. 9 2.2.1.3 Anthocyanin brain bioavailability .............................................................................. 13 2.2.2 Proanthocyanidins ............................................................................................................... 15 2.2.2.1 Proanthocyanidin stability.......................................................................................... 15 2.2.2.2 Proanthocyanidin bioavailability and metabolism .................................................. 15 2.2.2.3 Proanthocyanidin brain bioavailability ..................................................................... 16 2.2.3 Transport theories................................................................................................................ 17 2.3 Health benefits of anthocyanins and proanthocyanidins ............................................ 19 2.3.1 General health benefits ....................................................................................................... 19 2.3.1.1 Clinical and preclinical observations........................................................................ 19 2.3.1.2 Cellular functionalities................................................................................................ 19 2.3.2 Neuroprotection.................................................................................................................... 21 2.3.2.1 Neuroprotective effects.............................................................................................. 21 2.3.2.1.1 Target pathologies................................................................................................ 21 2.3.2.1.2 Neuroprotection mediated by anthocyanins and proanthocyanidins ............ 21 2.3.2.2 Neuroprotective mechanisms ................................................................................... 23 2.3.2.2.1 Pathomechanisms of neurodegenerative diseases and aging ...................... 23 2.3.2.2.2 Neuroprotection mediated by anthocyanins and proanthocyanidins ............ 26 2.3.2.2.2.1 Antioxidative mechanisms........................................................................... 26 2.3.2.2.2.2 Antiinflammatory mechanisms.................................................................... 27 2.3.2.2.2.3 Further candidate mechanisms .................................................................. 28 II Index 2.3.2.2.2.4 Monoamine oxidases inhibition................................................................... 29 2.3.2.2.2.5 Induction of hypoxia inducible factor (HIF) expression ........................... 31 2.3.2.2.2.6 Proteasome inhibition................................................................................... 33 2.3.2.2.2.7 Phospholipase A2 inhibition ......................................................................... 35 2.4 Toxicology and safety ........................................................................................................... 36 2.4.1 Legal classification and EU safety assessment strategies ............................................ 36 2.4.2 Safety assessment............................................................................................................... 39 2.4.2.1 Anthocyanin toxicity...................................................................................................
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