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Klonierung Von Cytochrom P450-Abhängigen

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Klonierung Von Cytochrom P450-Abhängigen Klonierung von Cytochrom P450-abhängigen Monooxygenasen aus Ammi majus L. und funktionelle Expression der Zimtsäure 4-Hydroxylase Dissertation zur Erlangung des Doktorgrades der Naturwissenschaften (Dr. rer. nat.) dem Fachbereich Pharmazie der Philipps-Universität Marburg vorgelegt von Silvia Specker aus Venedig (Italien) Marburg/Lahn 2004 Vom Fachbereich Pharmazie der Philipps-Universität Marburg als Dissertation angenommen am 14.1.2004. Erstgutachter: Prof. Dr. U. Matern Zweitgutachter: Prof. Dr. Alfred Batschauer Tag der mündlichen Prüfung: 14.1.2004 Wesentliche Auszüge dieser Arbeit wurden in der folgenden Publikation veröffentlicht: Hübner, S. , Hehmann, M., Schreiner, S., Lukačin, R. , Matern, U., 2003. Functional expression of cinnamate 4-hydroxylase from Ammi majus L. Phytochemistry 64, 445-452. Inhaltsverzeichnis I Inhaltsverzeichnis 1. EINLEITUNG ________________________________________________1 1.1 Die Furanocumarine ___________________________________________________ 1 1.1.1 Chemie der Furanocumarine _______________________________________________________ 1 1.1.2 Vorkommen____________________________________________________________________ 2 1.1.3 Bedeutung für die Pflanze – Grundlagen induzierter pflanzlicher Pathogenabwehr_____________ 2 1.1.4 Reaktionen von Petroselinum crispum nach Infektion mit Phytophthora sojae ________________ 6 1.1.5 Bioaktivitäten der linearen Furanocumarine ___________________________________________ 7 1.1.6 Anwendung der Furanocumarine in Medizin und Forschung _____________________________ 10 1.1.7 Interaktion zwischen Furanocumarinen und Insekten ___________________________________ 11 1.2 Die Biosynthese der linearen Furanocumarine ____________________________ 12 1.2.1 Der generelle Phenylpropanweg ___________________________________________________ 12 1.2.1.1 Wichtige Schritte der Phenylpropanbiosynthese_____________________________________ 12 1.2.2 Die Biosynthese des Umbelliferons ________________________________________________ 13 1.2.3 Die Prenylierung des Umbelliferons ________________________________________________ 14 1.2.4 Die Bildung von Marmesin _______________________________________________________ 16 1.2.5 Die Psoralensynthase____________________________________________________________ 17 1.2.6 Produkte aus Psoralen ___________________________________________________________ 18 1.2.7 Induzierbarkeit der Furanocumarinbiosynthese _______________________________________ 21 1.3 Ammi majus L. - Inhaltsstoffe und Bedeutung _____________________________ 21 1.4 Cytochrom P450 Enzyme ______________________________________________ 23 1.4.1 Einteilung und Nomenklatur ______________________________________________________ 24 1.4.2 Der Reaktionszyklus der Cyt P450 _________________________________________________ 25 1.4.3 Die Struktur eukaryotischer Cyt P450_______________________________________________ 27 1.4.4 Cyt P450 in Pflanzen____________________________________________________________ 30 1.4.5 Die Bedeutung der Cyt P450 für den Menschen _______________________________________ 31 1.4.6 Die NADPH-Cytochrom P450 Reduktase ___________________________________________ 32 1.4.7 „Mechanism-based enzyme inactivation” von Cyt P450 ________________________________ 33 1.5 Die Zimtsäure 4-Hydroxylase __________________________________________ 34 1.6 Regulation der Enzyme des Phenylpropanwegs____________________________ 35 1.7 Zielsetzung der Arbeit ________________________________________________ 37 2. MATERIAL UND METHODEN________________________________39 2.1 Material ____________________________________________________________ 39 2.1.1 Chemikalien und Verbrauchsmaterialien ____________________________________________ 39 2.1.2 Radiochemikalien ______________________________________________________________ 40 2.1.3 Substrate und Kosubstrate________________________________________________________ 40 2.1.4 Enzyme ______________________________________________________________________ 40 2.1.5 Reaktionssysteme und Kits _______________________________________________________ 40 2.1.6 Bakterien- und Hefestämme ______________________________________________________ 41 2.1.6.1 E.coli ______________________________________________________________________ 41 2.1.6.2 Hefe_______________________________________________________________________ 41 2.1.7 Vektoren _____________________________________________________________________ 42 2.1.7.1 E. coli-Vektoren _____________________________________________________________ 42 2.1.7.2 Hefeexpressionsvektoren_______________________________________________________ 42 2.1.8 Puffer und sonstige Lösungen _____________________________________________________ 43 Inhaltsverzeichnis II 2.1.9 Medien ______________________________________________________________________ 46 2.1.9.1 Bakterienmedien _____________________________________________________________ 46 2.1.9.2 Hefemedien _________________________________________________________________ 46 2.1.9.3 Zellkulturmedien _____________________________________________________________ 46 2.1.10 Dünnschichtplatten und Laufmittel _________________________________________________ 47 2.1.11 Geräte _______________________________________________________________________ 47 2.2 Methoden ___________________________________________________________ 48 2.2.1 Gewinnung des Pflanzenmaterials _________________________________________________ 48 2.2.1.1 Anzucht der Zellen ___________________________________________________________ 48 2.2.1.2 Induktion mit Elicitoren _______________________________________________________ 48 2.2.1.3 Ernte ______________________________________________________________________ 48 2.2.2 Molekularbiologische Methoden___________________________________________________ 48 2.2.2.1 RNA-Isolierung______________________________________________________________ 48 2.2.2.1.1 Isolierung von Gesamt-RNA (Methode A) _____________________________________ 48 2.2.2.1.2 Isolierung von Gesamt-RNA nach Giuliano (Methode B) __________________________ 48 2.2.2.1.3 Isolierung von poly(A)+-RNA _______________________________________________ 49 2.2.2.2 Reverse Transkription _________________________________________________________ 49 2.2.2.3 Polymerase-Ketten-Reaktion (PCR) ______________________________________________ 50 2.2.2.3.1 Synthese von Oligonukleotiden ______________________________________________ 50 2.2.2.3.2 Standard PCR ____________________________________________________________ 50 2.2.2.3.3 Cyt P450 spezifisches Differential Display (DD-RT-PCR) _________________________ 50 2.2.2.3.4 Cytochrom P450 spezifische PCR nach Fischer et al. (2001) _______________________ 51 2.2.2.3.5 PCR zur Amplifizierung der cDNA der CPR____________________________________ 53 2.2.2.4 Rapid Amplification of cDNA Ends (RACE) _______________________________________ 54 2.2.2.4.1 3’-RACE________________________________________________________________ 54 2.2.2.4.2 5’-RACE mit A- und C-Tailing ______________________________________________ 54 2.2.2.4.3 RLM-RACE _____________________________________________________________ 55 2.2.2.4.4 Mutagenese-PCR_____________________________________________________________ 57 2.2.2.5 Präparation von DNA _________________________________________________________ 58 2.2.2.5.1 Präparation von Plasmid DNA _______________________________________________ 58 2.2.2.5.1.1 Methode A___________________________________________________________ 58 2.2.2.5.1.2 Methode B ___________________________________________________________ 59 2.2.2.5.2 Isolierung von genomischer DNA __________________________________________ 59 2.2.2.6 DNA-Sequenzanalyse _________________________________________________________ 59 2.2.2.7 Northern Hybridisierung (Dot Blot) ______________________________________________ 59 2.2.2.7.1 Radioaktiven Markierung von DNA-Fragmenten ________________________________ 59 2.2.2.7.2 Blotting_________________________________________________________________ 60 2.2.2.7.3 Hybridisierung ___________________________________________________________ 60 2.2.2.8 Expression in Hefe ___________________________________________________________ 60 2.2.2.8.1 Klonierung in den Hefeexpressionsvektor pYeDP60______________________________ 60 2.2.2.8.2 Anzucht von Saccharomyces cerevisiae________________________________________ 60 2.2.2.8.3 Transformation von Saccharomyces cerevisiae __________________________________ 60 2.2.2.8.4 Induktion von transformierten Saccharomyces cerevisiae __________________________ 61 2.2.2.8.5 Isolierung der Hefemikrosomen ______________________________________________ 61 2.2.3 Biochemische Methoden_________________________________________________________ 61 2.2.3.1 Test auf C4H-Aktivität ________________________________________________________ 61 2.2.3.2 Test auf Marmesinsynthase-Aktivität _____________________________________________ 61 2.2.3.3 Test auf C3H-Aktivität ________________________________________________________ 62 2.2.3.3.1 4-Cumarsäure ____________________________________________________________ 62 2.2.3.3.2 Umsatz von Cumarsäuremethylester __________________________________________ 62 2.2.3.4 Proteinbestimmung ___________________________________________________________ 62 2.2.3.5 Nachweis der Aktivität der CPR in Hefemikrosomen_________________________________ 62 2.2.4 Sonstiges _____________________________________________________________________ 63 2.2.4.1 Radioaktivitätsmessungen______________________________________________________ 63 Inhaltsverzeichnis III 3. ERGEBNISSE _______________________________________________64
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