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Dissertation Diane Dobberstein Charakterisierung der Zellwandstrukturkomponenten von Maisrestpflanzen als mögliche Einflussfaktoren der ruminalen Zellwandabbaubarkeit Dissertation zur Erlangung des Doktorgrades des Departments Chemie der Fakultät für Mathematik, Informatik und Naturwissenschaften der Universität Hamburg aus dem Institut für Biochemie und Lebensmittelchemie - Abteilung für Lebensmittelchemie - vorgelegt von Diane Dobberstein aus Hamburg Hamburg 2009 Die vorliegende Arbeit wurde in der Zeit von Mai 2004 bis Oktober 2007 unter der Leitung von Herrn Prof. Dr. Dr. H. Steinhart am Institut für Biochemie und Lebensmittelchemie, Abteilung Lebensmittelchemie, der Universität Hamburg angefertigt. 1. Gutachter: Prof. Dr. Dr. H. Steinhart 2. Gutachter: Prof. Dr. B. Bisping Tag der Disputation: 28.07.2009 Begutachtende der Disputaion: Prof. Dr. Dr. H. Steinhart Prof. Dr. E. Stahl-Biskup Dr. A. Paschke DANKSAGUNGEN Herrn Prof. Dr. Dr. H. Steinhart und Herrn Prof. Dr. Mirko Bunzel möchte ich für die Bereitstellung des Themas und die Betreuung dieser Arbeit danken. Herrn Prof. Dr. B. Bisping danke ich für die Übernahme des Koreferats. Neben den Mitarbeitern der Abteilung Lebensmittelchemie, möchte ich besonders Herrn Prof. Dr. Mirko Bunzel sowie allen ehemaligen und derzeitigen Mitgliedern seiner Arbeitsgruppe, insbesondere Frau Dr. Carola Funk, Frau Dr. Diana Bunzel und Herrn Heinze, für die stete Unterstützung und vor allem auch für die schöne Zeit danken. Mein Dank gilt auch Herrn Christian Gillot, Frau Sabrina Ment, Frau Caroline Indorf, Frau Anne Freudenstein und Herrn Tim Lubinus, die mit ihrer tatkräftigen Unterstützung zum Gelingen dieser Arbeit beigetragen haben. Frau Dr. Diana Bunzel und Herrn Dr. Michael Wigotzki danke ich für die Durchsicht des Skriptes. Bei Herrn Prof. F.J. Schwarz und Frau Dr. F. Zeller von der Abteilung für Tierernährung der Technischen Universität München, bedanke ich mich für die gute Zusammenarbeit, die Bereitstellung der Untersuchungsmaterialien und die vielen angeregten Diskussionen. Herrn Prof. Dr. John Ralph danke ich für die Aufnahme zum Teil zeitaufwendiger NMR-Spektren. Mein ganz besonderer Dank gilt Frau Carola Göldnitz für eine wunderbare Freundschaft und meinen Eltern, deren Rückhalt und Unterstützung ich mir stets sicher sein durfte. Diese Arbeit wurde von der Monsanto Agrar Deutschland GmbH sowie von der H. Wilhelm Schaumann Stiftung finanziell gefördert. Meinen Eltern ABKÜRZUNGSVERZEICHNIS 0 h 0 h Material, wasserunlöslicher Pflanzenrückstand 24 h Rückstand nach 24 h ruminaler Inkubation AA Alditol acetate AACC Association of American Cereal Chemists ABSL Acetylbromidlösliches Lignin ( acetyl bromide soluble lignin) ACN Ac eto nitril ADF acid detergent fiber ADL acid detergent lignin AM Ausgangs material ANOVA Varianzanalyse ( an alysis of va riance) AOAC Association of Official Analytical Chemists Ara Ara binose (in Abbildungen) Ara f Ara bino furanose 2-Ara f in O-2-Position glykosidisch verknüpfte Ara bino furanose T-Ara f terminale Ara bino furanose AX neutrale Arabino xylane A/X Arabinose /X ylose-Verhältnis BG Bestimmungs grenze BSTFA N,O-Bis-trimethyl silyl-tri fluor acetamid c cyclisch C3H p-Cumarsäure-3-Hydroxylase C4H Zimtsäure-4-Hydroxylase ( Cinnamic acid-4-hydroxylase) CAD Zimtalkohol-Dehydrogenase ( Cinnamic alcohol dehydrogenase) CAld-5H Conifer ald ehyd-5-Hydroxylase CAld-OMT 5-Hydroxy conifer ald ehyd-O-Methyl transferase CCoAOMT Kaffeoyl-CoA-O-Methyltransferase (Caffeoyl-CoA -O-methyl transferase) CC p-Cumarsäure- p -Cumarsäure-Cyclobutandimer (in Abbildungen und Tabellen) CCR Cinnamoyl-CoA-Reduktase CCRC Complex Carbohydrate Research Center CF p-Cumarsäure-Ferulasäure-Cyclobutandimer (in Abbildungen und Tabellen) 4CL 4-Cumarsäure:CoA-Ligase COMT Kaffeesäure-O-Methyltransferase ( Caffeic acid-O-methyl transferase) COSY correlated spectroscop y CV Verfahrensvariationskoeffizent ( coefficient of variation) d Dublett (in Tabellen) DAD Dioden array detektion dc decarboxyliert dd Dublett vom Dublett (in Tabellen) DFRC derivatization followed by reductive cleavage DFS Dehydrodi ferula säure DMSO Dimethyl sulf oxid DWD Deutscher Wetter dienst E.C.R. effective carbon response EI Elektronenstoß-Ionisierung ESI Elektro spray-Ionisierung EtOH Ethanol EZP bzw.E Erntezeitpunkt (Abbildungen und Tabellen) F5H Ferulat-5-Hydroxylase FAX O-β-D-Xylopyranosyl-(1 →2)-[5-O-(trans -feruloyl)-L-arabinofuranose] FF Ferulasäure-Ferulasäure-Cyclobutandimer (in Abbildungen und Tabellen) FID Flammen ionisations detektor FID NMR freier Induktionsabfall ( Free Induction Declay) - NMR-Spektroskopie FS Ferula säure FS est est ergebundene Ferula säure (in Abbildungen) FS eth eth ergebundene Ferula säure (in Abbildungen) FS-CA FS -Coniferyl alkohol-Kreuzprodukt G Guaiacyl-Einheit 5-OH-G 5-Hydroxy guaiacyleinheit Gal Gal actose (in Abbildungen) T-Gal p terminale Gal acto pyranose Gal pA Galactopyranuronsäure ( Gal acto pyranuronic acid) (in Abbildungen) GAX Glucurono arabino xylane GC Gas chromatographie GK Grund kalibrierung Glc Gl ucose (in Abbildungen) Glc p Gl ucopyranose (in Abbildungen) 4-Glc p 1→4 glykosidisch verknüpfte Gl ucopyranose T-Glc p terminale Gl ucopyranose Glc pA Gluc opyranuronsäure ( glu co pyranuronic acid) H p-Hydroxyphenyl-Einheit 4-HBA 4-Hydroxy benz aldehyd 4-HBS 4-Hydroxy benzoe säure HCT p-Hydroxycinnamoyl-CoA:Shikimisäure Hydroxycinnamoyltransferase hh head-to-head HMBC heteronuclear multiple bond correlation HMQC heteronuclear multiple quantum coherence 4-HPES 4-Hydroxy phenyl essig säure HPLC Hochleistungsflüssigkeitschromatographie ( high performance liquid chromatography) 4-HPPS 4-Hydroxyphenyl propion säure HSD tatsächliche/wahre signifikante Abweichung ( honestly significant difference) ht head-to-tail ID Innendurchmesser IS Interner Standard K Körner (in Tabellen) KF Korrektur faktor (in Tabellen) KL Klason-Lignin KS Kaffee säure LSD geringste signifikante Abweichung ( least significant difference) m/z Masse/Ladungs-Verhältnis Man Man nose (in Abbildungen) MeI Me thyl iodid MEL Mono epoxy lignanolide (8-β-gekoppelte Ferulasäure-Coniferylalkohol-Kreuzprodukte mit Pinoresinolstruktur) MeOH Methanol Mio. Millionen MK Matrix kalibrierung MS Massen spektrometrie NADPH Nicotinamid adenin dinucleotid ph osphat nc nicht cyclisch NDF neutral detergent fiber NIRS near infra red spectroscopy NMR Kernresonanzspektroskopie ( nuclear magnetic resonance) NOE Kern-Overhauser-Effekt ( nuclear overhauser enhancement) NOESY nuclear overhauser enhancement spectroscop y NWG Nach weis grenze PAL Phenylalanin-Ammonium-Lyase pCS p-Cumar säure pCS est est ergebundene p-Cumar säure (in Abbildungen) PCS Phenol carbon säuren Ph Ph enolische Einheit (in Abbildungen) PMAA per methylierte Alditol acetate Rha p Rha mno pyranose (in Abbildungen) RP Umkehrphase ( reversed phase) RPf Rest pf lanze (in Tabellen) RRT Relative Retentionszeit ( relative retention time) RT Raum temperatur s Singulett S Syringyl-Einheit SAD Sinapyl alkohol-Dehydrogenase SD Standardabweichung ( standard deviation) SMA Standard methylierungs analyse S/N Signal/Rausch-Verhältnis ( signal-to-noise) SPE Festphasenextraktion ( solid phase extraction) SRZ Silo reife zahl (in Tabellen) SS Sinapin säure SyA Sy ring aldehyd SyS Sy ringa säure TetraFS Dehydro tetraf erula säure TFA Trifluoressigsäure ( tri fluoracetic acid) THF Tetra hydro furan TFS Dehydro tri ferula säure TIC total ion chromatogram TMS Tri methyl silan TS Trocken substanz TUM Technische Universität München U/min Umdrehung pro Min ute UBS unlösliche Ballast stoffe USDA United States Department of Agriculture UV Ultra violett VN Va nillin VS Vanillin säure WFR Wieder findungs rate Xyl Xyl ose (in Abbildungen) Xyl p Xyl opyranose (in Abbildungen) 4-Xyl p 1→4 glykosidisch verknüpfte Xyl opyranose T-Xyl p terminale Xyl opyranose 3,4-Xyl p 1→4 und 3 → glykosidisch verknüpfte Xyl opyranose 2,4-Xyl p 1→4 und 2 → glykosidisch verknüpfte Xyl opyranose 2,3,4-Xyl p 1→4 , 2 → und 3 → glykosidisch verknüpfte Xyl opyranose Symbole t1 Evolutionsphase/-zeit t2 Detektionsphase/-zeit δ chemische Verschiebung I Spinquantenzahl J Kopplungskonstante λ Detektionswellenlänge INHALTSVERZEICHNIS 1 Einleitung und Allgemeiner Teil 1 1.1 Allgemeiner Aufbau von Pflanzenzellwänden 2 1.1.1 Zellwandpolysaccharide 2 1.1.1.1 Cellulose 3 1.1.1.2 Hemicellulosen 3 1.1.1.3 Pektine 5 1.1.2 Zellwandgebundene Phenolcarbonsäuren 6 1.1.2.1 Monomere Phenolcarbonsäuren 7 1.1.2.2 Dimere und höhere Oligomere der Phenolcarbonsäuren 8 1.1.2.3 Cross-Linking von Zellwandpolymeren durch Phenolcarbonsäuren 12 1.1.3 Lignin 14 1.2 Grundlagen zum ruminalen Verdau von Futtermitteln 17 1.2.1 Allgemeiner Aufbau des Magenssystems des Wiederkäuers 17 1.2.2 Einfluss der Zellwandstrukturkomponenten auf die ruminale Futtermittelver- daubarkeit 18 1.3 Problemstellung 21 2 Material und Methoden 23 2.1 Material 23 2.1.1 Ausgangsmaterial 24 2.1.2 Wasserunlösliche Faserbestandteile - 0 h-Material 24 2.1.3 24 h ruminal inkubiertes Material 24 2.2 Methoden 25 2.2.1 Methoden zur Bestimmung der ruminalen Abbaubarkeit, des Auswaschver- lustes, des Rohproteins und der Rohasche 25 2.2.1.1 Bestimmung der ruminalen Abbaubarkeit 25 2.2.1.2 Bestimmung des Auswaschverlustes 26 2.2.1.3 Bestimmung des Rohproteins und der Rohasche in den Rohmaterialien 27 2.2.2 Methoden zur Bestimmung der Kohlenhydrate 27 2.2.2.1 Bestimmung der Gesamtkohlenhydratgehalte 27 2.2.2.2 Bestimmung der Gehalte an freier Glucose in den Ausgangsmaterialien 28 2.2.2.3 Bestimmung der Monosaccharidzusammensetzung der Polysaccharide 28 2.2.2.4 Bestimmung der Bindungsverhältnisse der Monosaccharid-Einheiten
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