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Untersuchungen Zum Metabolismus, Zur Bioverfügbarkeit Und Zur Antioxidativen Wirkung Von Anthocyanen

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Untersuchungen Zum Metabolismus, Zur Bioverfügbarkeit Und Zur Antioxidativen Wirkung Von Anthocyanen Untersuchungen zum Metabolismus, zur Bioverfügbarkeit und zur antioxidativen Wirkung von Anthocyanen Zur Erlangung des akademischen Grades eines DOKTORS DER NATURWISSENSCHAFTEN (Dr. rer. nat.) der Fakultät für Chemie und Biowissenschaften der Universität Karlsruhe (TH) vorgelegte DISSERTATION von Diplom-Lebensmittelchemiker Jens Fleschhut aus Heilbronn Dekan: Prof. Dr. Manfred M. Kappes Referent: Prof. Dr. Sabine E. Kulling Korreferent: Prof. Dr. Stefan Bräse Tag der mündlichen Prüfung: 25. Oktober 2004 Die vorliegende Arbeit wurde zwischen Juli 2001 und September 2004 im Institut für Ernährungsphysiologie der Bundesforschungsanstalt für Ernährung, Karlsruhe angefertigt. Frau Prof. Dr. Sabine E. Kulling danke ich für die Überlassung des interessanten Themas, ihre sehr wohlwollende und allzeit freundliche Unterstützung sowie für die großzügig gewährten Freiräume bei der Durchführung dieser Arbeit. Für meinen Opa INHALTSVERZEICHNIS Inhaltsverzeichnis 1 Einleitung und theoretische Grundlagen 1 1.1 Allgemeines . 1 1.2 Die Familie der Flavonoide . 1 1.3 Chemische Eigenschaften der Anthocyane . 2 1.3.1 Chemische Struktur . 2 1.3.2 Strukturelle Veränderungen in Abhängigkeit vom pH-Wert . 4 1.3.3 Zerfall der Anthocyanidine . 5 1.3.4 Bildung von Metallkomplexen . 6 1.4 Physikalische Eigenschaften der Anthocyane . 7 1.4.1 Absorptions-Spektren der Anthocyane . 7 1.4.2 Copigmentierung von Anthocyanen . 7 1.5 Natürliches Vorkommen der Anthocyane und Gehalte in Lebensmitteln . 8 1.6 Physiologische Eigenschaften der Anthocyane . 10 1.6.1 Antioxidative Eigenschaften . 11 1.6.2 Schutz vor koronaren Herzerkrankungen . 13 1.6.3 Schutz vor Krebserkrankungen . 15 1.6.4 Antibakterielle und antivirale Wirkung, Verbesserung der Nachtsicht und sonstige Effekte . 17 1.7 Bisherige Erkenntnisse zur Bioverfügbarkeit und zum Metabolismus der An- thocyane . 19 1.7.1 Aufnahme mit der Nahrung . 19 1.7.2 Bioverfügbarkeitsstudien . 20 1.7.3 Untersuchungen zum Metabolismus und den Aufnahme- und Vertei- lungsmechanismen . 22 2 Problemstellung 24 3 Ergebnisse 26 3.1 Entwicklung und Etablierung geeigneter analytischer Methoden . 26 3.1.1 Etablierung einer geeigneten Festphasenextraktion . 26 3.1.2 Etablierung einer geeigneten Flüssig-Flüssig-Extraktion . 27 3.1.3 Etablierung einer geeigneten HPLC-Methode . 27 3.1.4 Etablierung einer LC/MS-Methode und Strukturaufklärung verschie- dener natürlicher Anthocyane . 27 3.1.4.1 Strukturaufklärung . 28 i INHALTSVERZEICHNIS 3.1.4.2 Massenübersicht . 30 3.1.5 Etablierung einer GC/MS-Methode zum Nachweis phenolischer Säuren 31 3.1.6 Einfluss dreiwertiger Metallkationen auf die enzymatische Spaltung . 32 3.2 Allgemeine Untersuchungen zu Anthocyanen . 34 3.2.1 Stabilität der Aglykone bei unterschiedlichen pH-Werten und Einfluss dreiwertiger Metallkationen auf die Stabilität . 34 3.2.2 Verhalten der Anthocyane bei enzymatischen Umsetzungen . 36 3.2.2.1 Spaltung mit β-Glucuronidase . 36 3.2.2.2 Spaltung mit β-Glucosidase . 37 3.3 in vitro-Untersuchungen zum Metabolismus . 37 3.3.1 Phase I-Reaktionen . 37 3.3.1.1 Cytochrom P450-abhängige Oxidationen . 37 3.3.1.2 Intestinaler Metabolismus . 38 3.3.2 Phase II-Reaktionen . 41 3.3.2.1 Methylierung . 41 3.3.2.2 Glucuronidierung . 43 3.4 in vivo-Untersuchungen . 48 3.4.1 Tierexperimentelle Studien an Ratten . 48 3.4.1.1 Aufnahme von phenolischen Säuren . 48 3.4.1.2 Aufnahme von Anthocyanen . 52 3.4.2 Humanversuch – Pilotversuch . 60 3.4.2.1 Urin . 60 3.4.2.2 Plasma . 63 3.5 Antioxidative Eigenschaften der Anthocyane und ihrer Metabolite . 68 3.5.1 Trolox Equivalent Antioxidant Capacity (TEAC)-Assay . 68 3.5.1.1 Reaktionskinetiken und Methodenoptimierung . 68 3.5.1.2 Bestimmung der TEAC-Werte . 70 3.5.1.3 Synergismusuntersuchungen . 71 3.5.2 Ferric Reducing/Antioxidant Power (FRAP)-Assay . 71 3.5.2.1 Reaktionskinetiken und Methodenoptimierung . 71 3.5.2.2 Kalibrierung . 73 3.5.2.3 Bestimmung der EC1-Werte . 73 3.5.2.4 Synergismusuntersuchungen . 75 3.5.3 Oxygen Radical Absorbance Capacity (ORAC)-Assay . 76 3.5.3.1 Berechnung der Trolox-Äquivalente . 76 3.5.3.2 Vergleich der Ergebnisse der beiden Fluoreszenzfarbstoffe . 77 3.5.3.3 Synergismusuntersuchungen . 78 ii INHALTSVERZEICHNIS 3.5.4 Vergleich der Ergebnisse . 78 3.5.5 Messung einer Modell-Plasmalösung . 79 4 Diskussion 81 4.1 Stabilität und Optimierung der analytischen Methoden . 81 4.2 Metabolismus, Bioverfügbarkeit und Pharmakokinetik der Anthocyane . 82 4.2.1 in vitro-Untersuchungen . 82 4.2.2 in vivo-Untersuchungen . 85 4.2.3 Zusammenfassende Erkenntnisse aus den in vitro- und in vivo- Untersuchungen . 90 4.2.4 Weiterer Forschungsbedarf . 92 4.3 Biologische Wirkung . 94 4.3.1 Antioxidative Eigenschaften . 94 4.3.1.1 Gegenüberstellung der eingesetzten Testsysteme . 94 4.3.1.2 Struktur-Wirkungs-Beziehungen . 95 4.3.1.3 Synergismusuntersuchungen . 98 4.3.2 Beurteilung der biologischen Wirkung und gesundheitsprotektiven Re- levanz einer anthocyanreichen Ernährung . 98 5 Zusammenfassung 102 6 Experimenteller Teil 105 6.1 Geräte und Chemikalien . 105 6.1.1 Liste der verwendeten Geräte . 105 6.1.2 Liste der verwendeten Chemikalien und Verbrauchsmaterialien . 106 6.1.2.1 Allgemeine Chemikalien . 106 6.1.2.2 in vitro-Untersuchungen . 108 6.1.2.3 in vivo-Untersuchungen . 109 6.1.2.4 Untersuchungen zur antioxidativen Wirkung . 109 6.2 Methoden . 111 6.2.1 Analytik . 111 6.2.1.1 Gewinnung von Lebensmittelextrakten . 111 6.2.1.2 Isolierung von Anthocyanen mittels HSCCC . 111 6.2.1.3 Festphasenextraktion . 111 6.2.1.4 Flüssig-Flüssig-Extraktion . 112 6.2.1.5 HPLC/DAD und HPLC/MS . 112 6.2.1.6 GC/MS . 114 6.2.2 Allgemeine Untersuchungen . 115 iii INHALTSVERZEICHNIS 6.2.2.1 Stabilitätsuntersuchungen . 115 6.2.2.2 Enzymatische Inkubationen mit β-Glucosidase und β- Glucuronidase . 115 6.2.3 in vitro-Metabolismus-Assays . 116 6.2.3.1 Mikrosomale Umsetzung . 116 6.2.3.2 Anaerobe Inkubation mit Fäzes-Suspensionen . 119 6.2.3.3 Methylierung durch Inkubation mit COMT/SAM . 120 6.2.3.4 Glucuronidierungsreaktionen . 121 6.2.4 in vivo-Studien . 122 6.2.4.1 Tierversuche . 122 6.2.4.2 Humanversuch . 127 6.2.5 Antioxidativitäts-Assays . 131 6.2.5.1 TEAC-Assay . 131 6.2.5.2 FRAP-Assay . 133 6.2.5.3 ORAC-Assay . 135 6.2.5.4 Synergismusuntersuchungen . 139 6.2.5.5 Statistische Methoden zur Signifikanzüberprüfung . 139 A Anhang 141 A.1 Übersichtsdaten . 141 A.2 Massenspektren . 143 A.3 Sonstiges . 145 B Abbildungsverzeichnis 146 C Tabellenverzeichnis 150 D Literaturverzeichnis 152 E Publikationsliste 176 F Danksagungen 178 iv WISSENSCHAFTLICHE ABKÜRZUNGEN Wissenschaftliche Abkürzungen ∗ signifikant mit P < 0,05 ∗∗ signifikant mit P < 0,01 aA acyliertes Anthocyan ABAP 2,2-Azobis(2-amidinopropan) Dihydrochlorid ABTS 2,2’-Azino-bis(3-ethylbenzothiazolin-6-sulfonsäure) Diammoniumsalz AC Anthocyan AM Abweichung vom Mittelwert ANOVA analysis of variance (Varianzanalyse) AP-1 Activator protein-1 API-ES atmospheric pressure ionisation electrospray ASC Ascorbinsäure AUC Area under the curve (Fläche unter der Kurve) bidest. bidestilliert BMI Body Mass Index BSA bovine serum albumin (Rinderserumalbumin) BSTFA N ,O-bis(Trimethylsilyl)trifluoracetamid CCC Countercurrent Chromatography COMT Catechol-O-methyltransferase COX Cyclooxigenase (Prostaglandin-Endoperoxid H-Synthase) CS Cumarsäure Cy Cyanidin Cy3ara Cyanidin-3-O-β-D-arabinosid Cy3glc Cyanidin-3-O-β-D-glucosid (Kuromanin) Cy3gal Cyanidin-3-O-β-D-galactosid (Idaein) Cy3rut Cyanidin-3-O-β-D-rutinosid Cy3sam Cyanidin-3-O-β-D-sambubiosid Cy35d-glc Cyanidin-3,5-O-β-D-diglucosid (Cyanin) Cy-rut/glc Cyanidin-3-rutinosid-5-glucosid Cy-sam/glc Cyanidin-3-sambubiosid-5-glucosid CYP-450 Cytochrom P-450 DAD Diodenarraydetektor Del Delphinidin Del3glc Delphinidin-3-O-β-D-glucosid Del3rut Delphinidin-3-O-β-D-rutinosid v WISSENSCHAFTLICHE ABKÜRZUNGEN DP degeneration product (Abbauprodukt) DNA Desoxyribonukleinsäure EGC(g) Epigallocatechin(gallat) EGFR Epidermal Growth-factor Receptor EI electron impact (Elektronenstoß) ER Endoplasmatisches Retikulum ERK Extrazelluläre Signal-regulierte Kinase FIA Fließmittelinjektionsanalyse FL Fluorescein FRAP Ferric Reducing Activity of Plasma oder Ferric Reducing/Antioxidant Power FS Ferulasäure GC Gaschromatographie glc Glucose HDL high density lipoproteins (Lipoproteine hoher Dichte) HEPES 4-(2-Hydroxyethyl)-piperazin-1-ethansulfonsäure HPLC Hochleistungsflüssigchromatographie HSCCC High Speed Countercurrent Chromatography Hkt Hämatokrit-Wert IS Interner Standard JNK/SAPK c-Jun N-terminale Kinase/Stress-aktivierte Protein-Kinase KG Körpergewicht KS Kaffeesäure LC Liquid Chromatography LDL low density lipoproteins (Lipoproteine niedriger Dichte) M Molekulargewicht m/z Masse / Ladungsverhältnis Mal Malvidin MAL Malonsäure Mal3glc Malvidin-3-O-β-D-glucosid (Oenin) Mal35d-glc Malvidin-3,5-O-β-D-diglucosid (Malvin) MAP mitogen-activated protein (Mitogen-aktiviertes Protein) mAU milli absorption units (Milliabsorptionseinheiten) MeOH Methanol MS Massenspektrometrie MW arithmetischer Mittelwert NADH reduziertes Nicotinamid-Adenin-Dinucleotid NADPH reduziertes Nicotinamid-Adenin-Dinucleotid-Phosphat vi WISSENSCHAFTLICHE ABKÜRZUNGEN NMR Nuclear Magnetic Resonance (Magnetische Kernresonanz) ORAC Oxygen Radical Absorbance Capacity PBS-Puffer Phosphate Buffered Saline (Phosphatpuffer mit 0,15 M NaCl, pH 7,3) PE R-Phycoerythrin Pel Pelargonidin Pel3ara Pelargonidin-3-O-β-D-arabinosid Pel3glc Pelargonidin-3-O-β-D-glucosid (Callistephin) Pel-soph/glc Pelargonidin-3-sophorosid-5-glucosid Peo Peonidin Peo3glc Peonidin-3-O-β-D-glucosid Peo35d-glc Peonidin-3,5-O-β-D-diglucosid Pet Petunidin Pet3glc Petunidin-3-O-β-D-glucosid
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