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Dissertation Charakterisierung von oligomeren Kakao- Proanthocyanidinen: Extraktion und chromatographische Trennung mit simultaner Bestimmung der antioxidativen Kapazität Vasilisa Pedan 2017 Charakterisierung von oligomeren Kakao-Proanthocyanidinen: Extraktion und chromatographische Trennung mit simultaner Bestimmung der antioxidativen Kapazität Dissertation zur Erlangung des naturwissenschaftlichen Doktorgrades (Dr. rer. nat.) des Fachbereichs Chemie, Fakultät für Mathematik, Informatik und Naturwissenschaften der Universität Hamburg vorgelegt von Dipl. LMChem Vasilisa Pedan Hamburg März 2017 Die vorliegende Arbeit wurde in der Zeit von November 2012 bis März 2017 unter der Leitung von Herrn Prof. Dr. Sascha Rohn, Institut für Lebensmittelchemie der Universität Hamburg, angefertigt. Die praktischen Arbeiten erfolgten an der Zürcher Hochschule für Angewandte Wissenschaften in Wädenswil in der Schweiz unter der Betreuung von Herrn Dr. Norbert Fischer. Tag der Disputation: 30.10.2017 1. Gutachter der Dissertation: Prof. Dr. Sascha Rohn 2. Gutachter der Dissertation: Prof. Dr. Bernward Bisping Kein zweites Mal hat die Natur solche Fülle der wertvollsten Nährstoffe auf einem so kleinen Raum zusammengedrängt wie gerade bei der Kakaobohne. Alexander von Humboldt Veröffentlichungen Publikationen Pedan V, Weber, C, Do T, Fischer N, Reich E, Rohn S (2017) HPTLC fingerprint profile analysis of cocoa proanthocyanidins depending on origin and genotype. Food Chemistry. In press Pedan V, Fischer N, Bernath K, Hühn T, Rohn S (2017) Determination of oligomeric proanthocyanidins and their antioxidant activity from different chocolate manufacturing stages using the NP-HPLC-online-DPPH methodology. Food Chemistry, 214, 523-532. Pedan V, Fischer N, & Rohn S (2016) Extraction of cocoa proanthocyanidins and their fractionation by sequential centrifugal partition chromatography and gel permeation chromatography. Analytical and Bioanalytical Chemistry, 408, 5905-5914. Pedan V, Fischer N, & Rohn S (2016) An online NP-HPLC-DPPH method for the determination of the antioxidant activity of condensed polyphenols in cocoa. Food Research International, 89, 890-900. Vorträge Pedan V, Weber C, Do T, Fischer N, Reich E, Rohn S (2016) High performance thin layer chromatography: Determination of oligomeric proanthocyanidins during different chocolate manufacturing stages. The 1st Food Chemistry Conference, 30. Oktober - 1 November 2016, Amsterdam, Niederlande. Pedan V, Fischer N, Rohn S (2015) An online NP-HPLC-DPPH method for the determination of the antioxidant activity of condensed polyphenols in cocoa. 3rd International Congress on Cocoa Coffee and Tea, 22.-24. Juni 2015, Aveiro, Portugal. Pedan V, Fischer N, Rohn S (2015) An online NP-HPLC-DPPH method for the determination of the antioxidant activity of condensed polyphenols from different chocolate manufacturing stages. 4th International Conference and Exhibition on Food Processing & Technology, 10.- 12. August 2015. In: Proceedings of 4th International Conference and Exhibition on Food Processing & Technology 6 (8), ISSN: 2157-7110: 100. Pedan V, Fischer N, Rohn S (2015) Monitoring of condensed polyphenols and their antioxidant activity in cocoa processing. 29th EFFoST International Conference, 28.-30. i November, Athen, Griechenland. In: Proceedings of 29th EFFoST International Conference, ISBN: 978-618-82196-1-8: 82-85. Pedan V, Weber C, Muthusamy A, Fischer N, Rohn S (2015) HPTLC determination of cocoa polyphenols from different chocolate manufacturing stages, Lebensmittel 4.0, Wädenswiler Lebensmitteltagung, 9. November 2015, Wädenswil, Schweiz. Poster Pedan V, Weber, C, Do T, Reich E, Rohn S (2017) HPTLC fingerprint profile analysis of cocoa proanthocyanidins depending on origin and genotype. International Symposium for High-Performance Thin-Layer Chromatography, 4.-8. Juli, Berlin, Deutschland. Pedan V, Fischer N, Rohn S (2015) An online NP-HPLC-DPPH method for the determination of the antioxidant activity of condensed polyphenols in cocoa, 3rd International Congress on Cocoa Coffee and Tea, 22.-24. Juni 2015, Aveiro, Portugal. Pedan V, Fischer N, Rohn S (2015) Preparative isolation of cocoa alkaloids and polyphenols using sequential centrifugal partition chromatography, 18th Edition of EuroAnalysis, the European Conference on Analytical Chemistry, 6.-7. September 2015, Bordeaux, Frankreich. Pedan V, Fischer N, Rohn S (2015) Fractionation of condensed cocoa polyphenols using semi-preparative NP-HPLC. 44. Deutscher Lebensmittelchemikertag, 14.-16. September 2015, Karlsruhe, Deutschland. ISBN 978-3-936028-93-5: 119. Pedan V, Fischer N, Rohn S (2015) An online NP-HPLC-DPPH method for the determination of the antioxidant activity of condensed polyphenols from different chocolate manufacturing stages, 44. Deutscher Lebensmittelchemikertag, 14.-16. September 2015, Karlsruhe, Deutschland. ISBN 978-3-936028-93-5: 120. Pedan V, Weber C, Muthusamy A, Fischer N, Rohn S (2015) HPTLC determination of cocoa polyphenols from different chocolate manufacturing stages, Lebensmittel 4.0, 9. November 2015, Wädenswiler Lebensmitteltagung, Wädenswil, Schweiz. Huber P, Merola S, Pedan V, Fischer N, Perugini P, Capra P (2015) Study of polyphenol penetration from organic-aqueous cocoa extracts - antioxidant activity, The International Federation of Societies of Cosmetic Chemists, 21-23. September 2015, Zürich, Schweiz. ii Inhaltsverzeichnis ABKÜRZUNGSVERZEICHNIS ................................................................................................... VI KURZFASSUNG................................................................................................................................ 1 ABSTRACT ......................................................................................................................................... 3 1. EINLEITUNG .......................................................................................................................... 5 2. THEORETISCHER HINTERGRUND ............................................................................. 7 2.1. Sekundäre Pflanzenstoffe des Kakaos ...................................................................................... 7 2.2. Die Biosynthese von Polyphenolen in Kakao ......................................................................... 21 2.3. Verarbeitung von Theobroma cacao Linné ............................................................................. 26 2.3.1. Genetik .............................................................................................................................. ............. 26 2.3.2. Fermentation .............................................................................................................................. ... 28 2.3.3. Trocknung .............................................................................................................................. ........ 30 2.3.4. Rösten .............................................................................................................................. .............. 31 2.3.5. Alkalisierung .............................................................................................................................. .... 32 2.3.6. Conchieren .............................................................................................................................. ...... 33 2.3.7. Schokolade .............................................................................................................................. ...... 33 2.4. Kolorimetrische Messmethoden ............................................................................................... 33 2.4.1. Gesamtpolyphenolbestimmung mittels FOLIN-CIOCALTEU-Assay .......................................... 34 2.4.2. Gesamtflavonoidbestimmung mittels Aluminiumchlorid-Assay ............................................. 35 2.4.3. Proanthocyanidinbestimmung mittels Butanol-HCl-Assay ..................................................... 35 2.5. Antioxidative Kapazität von Polyphenolen ............................................................................. 37 2.5.1. Bestimmung der antioxidative Kapazität mittels DPPH .......................................................... 38 2.6. Verwendung chromatographischer Trenntechniken für die Matrix Kakao ......................... 39 2.6.1. Bestimmung der antioxidativen Kapazität oligomerer Proanthocyanidine mittels NP-LC- online-DPPH .............................................................................................................................. ... 39 2.6.2. Fraktionierung oligomerer Proanthocyanidine mittels semipräparativer NP-LC ................. 40 2.6.3. Fraktionierung phenolischer Substanzen mittels SCPC ......................................................... 41 2.6.4. Isolierung individueller oligomerer PA mittels Gelpermeationschromatographie ................ 43 2.6.5. Identifizierung monomerer Polyphenole mittels LC-DAD-ESI-MS ........................................ 44 2.6.6. Quantifizierung monomerer Polyphenole mittels LC-DAD-ESI-MS ...................................... 45 3. PROBLEMSTELLUNG UND ZIELSETZUNG .......................................................... 46 4. KUMULATIVER TEIL DER DISSERTATION ........................................................... 48 4.1. Extraktion von Kakaoproanthocyanidinen und deren Fraktionierung mittels Gegenstromverteilungschromatographie und Gelpermeationschromatographie ........... 49 iii 4.1.1. Abstract .............................................................................................................................
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