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Einfluss Von Lignin Und Ferulasäurederivaten Auf Die Adsorptionseigenschaften Von Ballaststoffen Und Den Fermentativen Abbau Durch Die Menschliche Darmflora

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Einfluss Von Lignin Und Ferulasäurederivaten Auf Die Adsorptionseigenschaften Von Ballaststoffen Und Den Fermentativen Abbau Durch Die Menschliche Darmflora Einfluss von Lignin und Ferulasäurederivaten auf die Adsorptionseigenschaften von Ballaststoffen und den fermentativen Abbau durch die menschliche Darmflora Dissertation zur Erlangung des Doktorgrades des Fachbereiches Chemie der Universität Hamburg aus dem Institut für Biochemie und Lebensmittelchemie Abteilung für Lebensmittelchemie vorgelegt von Carola Funk aus Hamburg Hamburg 2007 Die vorliegende Arbeit wurde in der Zeit von April 2003 bis Oktober 2006 unter der Leitung von Herrn Prof. Dr. Dr. H. Steinhart am Institut für Biochemie und Lebensmittelchemie, Abtei- lung für Lebensmittelchemie, der Universität Hamburg angefertigt. 1. Gutachter: Prof. Dr. Dr. H. Steinhart 2. Gutachter: Prof. Dr. B. Bisping Tag der Disputation: 21.12.2007 Prüfungskommission: Prof. Dr. Dr. H. Steinhart Prof. Dr. E. Stahl-Biskup Dr. M. Körs Danksagung Zuallererst möchte ich mich herzlichst bei meinem Doktorvater Prof. Dr. Dr. Hans Steinhart für die Betreuung und Unterstützung meiner Doktorarbeit bedanken. Prof. Dr. Bernward Bisping danke ich für die bereitwillige Durchsicht meiner Arbeit als Zweit- gutachter. Mein ganz besonderer Dank gilt Prof. Dr. Mirko Bunzel, dem ich nicht nur das Thema meiner Doktorarbeit zu verdanken habe, sondern der mich und meine Arbeit auch maßgeblich ge- prägt hat. Ich habe durch ihn eine großartige wissenschaftliche Unterstützung erfahren. Ebenso schätze ich sehr seinen Humor und die Freundschaft, die sich im Laufe unserer ge- meinsamen Jahre an der Universität Hamburg entwickelt hat. Sehr dankbar bin ich ihm für die unvergesslichen USA-Forschungsaufenthalte, die er mir ermöglicht hat. Bei Ella Allerdings, Andreas Heinze, Reiko Yonekura und ganz besonders bei Diane Dob- berstein und Diana Gniechwitz bedanke ich mich für eine tolle gemeinsame Laborzeit. Es ist viel Wert, wenn im Labor nicht nur alle fachlichen Fragen diskutiert werden können, sondern die Arbeit ebenso mit so guten Freundschaften - auch über das Labor hinaus - eng verbun- den ist. Ebenso bedanke ich mich bei allen anderen Kolleginnen und Kollegen der Lebensmittelche- mie Hamburg für die schönen Jahre, insbesondere bei Sabine Gremmel, mit der ich einen langen Weg gemeinsam gegangen bin. Zu großem Dank bin ich Patrick Weber, Janina Thilker und Juliane Peters verpflichtet, die diese Arbeit mit viel Engagement unterstützt haben. Es war eine sehr schöne Zeit mit ihnen. Special thanks go to Prof. Dr. John H. Grabber, Christy Davidson, Prof. Dr. John and Sally Ralph for supervising and helping me with my research studies at the U.S. Dairy Forage Re- search Center in Madison and for being so great hosts. I also thank Dr. Ronald Hatfield, Dr. Jane Marita, Dr. Hoon Kim and Dr. Fachuang Lu for the kind support. Der H. Wilhelm-Schaumann-Stiftung danke ich für die finanzielle Unterstützung beider For- schungsaufenthalte am U.S. Dairy Forage Research Center in Madison, USA. Des Weiteren danke ich Dr. Annett Braune, die mir die Durchführung der Fermentationsstu- dien am Deutschen Institut für Ernährungsforschung Potsdam-Rehbrücke ermöglicht hat, für die gute Zusammenarbeit. Ein ganz großes Dankeschön geht an meine Familie, auf deren Unterstützung und Hilfe ich mich jederzeit verlassen konnte. Schließlich sei allen fleißigen Korrektur-Lesern dieser Arbeit gedankt! Meinen drei Funken INHALTSVERZEICHNIS A. Abkürzungsverzeichnis ..................................................................................................III B. Gefahrstoffliste...............................................................................................................VI 1 EINLEITUNG ..................................................................................................................1 2 ALLGEMEINER TEIL......................................................................................................2 2.1 Ballaststoffe ...............................................................................................................2 2.1.1 Definition von Ballaststoffen ..................................................................................2 2.1.2 Ballaststoffe im menschlichen Gastrointestinaltrakt ..............................................2 2.1.2.1 Ballaststoffe im Dünndarm .......................................................................................... 2 2.1.2.2 Ballaststoffe im Dickdarm ............................................................................................ 3 2.2 Pflanzenzellwände .....................................................................................................4 2.2.1 Aufbau von Pflanzenzellwänden ...........................................................................5 2.2.1.1 Kohlenhydratzusammensetzung ................................................................................. 5 2.2.1.2 Zellwandgebundene Ferulasäure................................................................................ 7 2.2.1.3 Lignin .........................................................................................................................12 2.2.2 Zellwand-Modellsysteme .....................................................................................17 2.3 Heterozyklische aromatische Amine........................................................................18 2.3.1 Struktur und Vorkommen.....................................................................................18 2.3.2 Mutagenität und Kanzerogenität..........................................................................20 2.3.3 Adsorption an Ballaststoffe..................................................................................22 2.4 Gallensäuren............................................................................................................23 2.4.1 Struktur und Vorkommen.....................................................................................23 2.4.2 Physiologische Eigenschaften von Gallensäuren................................................26 2.4.3 Adsorption an Ballaststoffe..................................................................................27 2.5 Zielsetzung der Arbeit ..............................................................................................28 2.6 Literatur....................................................................................................................30 3 ERGEBNISSE...............................................................................................................41 3.1 Isolierung und Strukturcharakterisierung der 8-O-4/8-O-4- und 8-8/8-O-4- gekoppelten Dehydrotriferulasäuren aus Maiskleie .................................................41 3.2 Untersuchung des Einflusses zellwandgebundener Ferulasäure sowie von Di- und Triferulasäuren auf den Abbau von Maiszellwänden durch die humane Darmmikrobiota........................................................................................................56 3.3 Bestimmung des Einflusses der Lignifizierung und des Gehaltes an Ferula- säurederivaten von Maiszellwänden auf die Adsorption von heterozyklischen aromatischen Aminen ..............................................................................................69 3.4 Studien zum Abbau lignifizierter Zellwände durch die menschliche Darmflora und Einfluss auf die Adsorption heterozyklischer aromatischer Amine ...................86 3.5 Untersuchung eines möglichen Einflusses der Lignifizierung von Maiszell- wänden auf die Adsorption von Gallensäuren .........................................................99 I 4 ZUSAMMENFASSENDE DISKUSSION.....................................................................112 4.1 Ferulasäure und ihre oligomeren Verbindungen....................................................112 4.1.1 Strukturanalyse oligomerer Ferulasäureverbindungen......................................112 4.1.2 Einfluss von Ferulasäure und Diferulasäure-Cross-Links auf die Adsorption von heterozyklischen aromatischen Aminen an Ballaststoffe............................116 4.1.3 Einfluss von Ferulasäure und Diferulasäure-Cross-Links auf den fermen- tativen Zellwandabbau durch die humane Darmmikrobiota ..............................119 4.2 Lignin .....................................................................................................................122 4.2.1 Einfluss von Lignin auf die Adsorption von heterozyklischen aromatischen Aminen an Ballaststoffe.....................................................................................122 4.2.2 Einfluss von Lignin auf die Adsorption von Gallensäuren an Ballaststoffe........125 4.2.3 Einfluss von Lignin auf den fermentativen Zellwandabbau durch die humane Darmmikrobiota .................................................................................................127 4.3 Literatur..................................................................................................................129 5 ZUSAMMMENFASSUNG ...........................................................................................136 SUMMARY..................................................................................................................139 6 ANHANG.....................................................................................................................142 6.1 Liste der Publikationen...........................................................................................142 6.2 Liste der Vorträge ..................................................................................................143 6.3 Liste der Poster......................................................................................................143
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