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Table of Contents DISSERTATION Dianthus versicolor FISCH. – Phytochemical and biological investigations of a traditional Mongolian medicinal plant angestrebter akademischer Grad Doktorin der Naturwissenschaften (Dr. rer.nat.) Verfasserin: Astrid Obmann Dissertationsgebiet (lt. Pharmazie Studienblatt): Betreuerin / Betreuer: Ao. Univ. Prof. Mag. Dr. Sabine Glasl-Tazreiter Wien, im Dezember 2010 Danksagung Univ. Prof. Mag. Dr. Dr. hc. Brigitte Kopp danke ich für die Bereitstellung des Arbeitsplatzes am Department für Pharmakognosie im WS 2005/2006. Univ.-Prof. Dr. Verena Dirsch danke ich für die Bereitstellung des Arbeitsplatzes am Department für Pharmakognosie von SS 2006 bis WS 2010/2011. Ganz besonderer Dank gebührt ao. Univ. Prof. Mag. Dr. Sabine Glasl-Tazreiter für die interessante Themenstellung und vor allem für die ausgezeichnete Betreuung. In ihr hatte ich nicht nur jederzeit eine kompetente Ansprechpartnerin in fachlichen Fragen, sondern auch eine Mentorin, die mich stets motiviert hat. Danke für alles, Sabine! Ass. Prof. Mag. Dr. Christa Kletter danke ich für die angenehme Zusammenarbeit, sowie für zahlreiche Hintergrundinformationen und Diskussionen zum „Mongolei- Projekt“. Herzlichen Dank an Ass. Prof. Mag. Dr. Armin Presser, für die Aufnahme der NMR- Spektren und die Unterstützung bei der Auswertung. Bei ao. Univ.-Prof. Dr. Theresia Thalhammer und ihrer Arbeitsgruppe bedanke ich mich für die Durchführung der Leberperfusionen. Ein großes Dankeschön an Dr. Martin Zehl für die Unterstützung im Rahmen der MS- ESI-IT-Analysen und die für mich sehr lehrreiche Zusammenarbeit im Rahmen der gemeinsamen Publikationen. Ao. Univ. Prof. Mag. Dr. Gottfried Reznicek danke ich für zahlreiche Tipps bei der Bearbeitung analytischer Fragestellungen. Vielen Dank an Mag. Tina Radovic, Mag. Zita Swoboda und Mag. Birgit Weisz-Pecher, die im Rahmen ihrer Diplomarbeit zum Gelingen dieser Dissertation beigetragen haben. Allen Kolleginnen und Kollegen danke ich für zahlreiche heitere Stunden im und außerhalb des Labors. Es war eine tolle Zeit! Großer Dank gebührt meiner Familie, die mich während des gesamten Studiums unterstützt hat. Lieber Ludwig, danke, dass du in den letzten Jahren immer für mich da warst und mir stets den Rücken freigehalten hast! This thesis is based on the following publications: 1. Obmann, A., Tsendayush, D., Thalhammer, T., Zehl, M., Vo, T.P.N., Purevsuren, S., Narantuya, S., Kletter, C., Glasl, S. Extracts from the Mongolian traditional medicinal plants Dianthus versicolor FISCH. and Lilium pumilum DELILE stimulate bile flow in an isolated perfused rat liver model J. Ethnopharmacol. 2010, 131, 555-561 2. Obmann, A., Werner, I., Presser, A., Zehl, M., Purevsuren, S., Narantuya, S., Kletter, C., Glasl, S. Flavonoid C- and O-glycosides from the Mongolian Medicinal Plant Dianthus versicolor FISCH. Chem. Pharm. Bull., 2010, in preparation 3. Obmann, A., Zehl, M., Purevsuren, S., Narantuya, S., Reznicek, G., Kletter, C., Glasl, S. Quantification of flavonoid glycosides from the traditional Mongolian medicinal plant Dianthus versicolor FISCH., Journal of Separation Science, accepted for publication on 17th November 2010 4. Astrid Obmann, Sodnomtseren Purevsuren, Martin Zehl, Christa Kletter, Gottfried Reznicek, Samdan Narantuya, Sabine Glasl HPLC Determination of flavonoid glycosides in Mongolian Dianthus versicolor FISCH. (Caryophyllaceae) compared to quantification by UV- spectrophotometry Phytochemical Analysis, 2010, in preparation Table of Contents 1 Introduction ................................................................................................... 3 1.1 Traditional Mongolian Medicine ................................................................ 3 1.1.1 Historical background of TMM ........................................................... 3 1.1.2 Principles of Traditional Mongolian Medicine ..................................... 5 1.1.3 Traditional Mongolian medicinal preparations.................................... 6 1.1.4 The Mongolian health care system .................................................... 8 1.1.5 Health situation in Mongolia ............................................................... 9 1.2 Liver and bile flow................................................................................... 11 1.3 Dianthus versicolor FISCH. ...................................................................... 14 1.4 Aim of the thesis and overview of publications ....................................... 17 2 Material and methods ................................................................................. 18 2.1 Plant material.......................................................................................... 18 2.2 Extraction, fractionation and isolation ..................................................... 19 2.2.1 Preparation of the aqueous extract (OWE) ...................................... 19 2.2.2 Solid phase extraction (SPE) ........................................................... 20 2.2.3 Centrifugal partition chromatography (CPC) .................................... 20 2.2.4 Column chromatography (CC) ......................................................... 21 2.2.5 Semipreparative high performance liquid chromatography (HPLC) . 22 2.3 Analytical methods ................................................................................. 24 2.3.1 Thin layer chromatography (TLC) .................................................... 24 2.3.2 High performance liquid chromatography (HPLC)............................ 25 2.3.3 Gas chromatography-mass spectrometry (GC-MS)......................... 25 2.3.4 UV-spectrophotometry (UV)............................................................. 26 2.3.5 Mass-spectrometry (MS).................................................................. 26 2.3.6 Nuclear magnetic resonance spectroscopy (NMR).......................... 26 2.4 Biological methods ................................................................................. 27 2.4.1 Isolated perfused rat liver................................................................. 27 2.4.2 Isolated organ preparations ............................................................. 27 3 Results ......................................................................................................... 29 3.1 Preparative section................................................................................. 29 3.2 Analytical section.................................................................................... 86 3.3 Biological section.................................................................................. 126 3.4 Additional analyses and optimization of methods ................................. 134 3.4.1 TLC ................................................................................................ 134 3.4.2 Optimization of HPLC-methods...................................................... 138 3.4.2.1 Establishment of an analytical HPLC-method ......................... 138 3.4.2.2 Quantification of flavonoids by HPLC-UV ................................ 146 3.4.3 Determination of sugar moieties .................................................... 147 4 Discussion and Conclusion ..................................................................... 151 5 Summary.................................................................................................... 155 1 6 Zusammenfassung.................................................................................... 156 7 References ................................................................................................. 157 8 Curriculum vitae & List of publications................................................... 162 Appendi x .......................................................................................................165 2 1 Introduction Traditional medicinal systems, especially of Asian origin, have become more interesting in Western countries during the last decades. Traditional Chinese Medicine, Ayurveda and Traditional Tibetan Medicine are popular ones, which are often applied to patients in many European countries as alternative (complementary) medical treatment. Rather unknown is the Traditional Mongolian Medicine (TMM). Considering the Mongolian history there has been an increasing interest in traditional Mongolian medicine since the beginning of the 1990s. This led to scientific investigations in this ancient medical system not only within Mongolia, but also together with foreign academic institutions in Asian and Western countries. Among the new academic partners were also various universities in Austria, and one of them is the Department of Pharmacognosy in Vienna [1]. 1.1 Traditional Mongolian Medicine Literature about TMM is scarce and mostly written in Mongolian or Russian. However, some books are also edited in English and some interesting information about the Mongolian health system and the use of traditional medicine during the last decade is compiled in reports available in online- databases [2, 3, 4, 5]. The next chapters provide a comprehensive overview about the available literature and refer to the following topics: Historical background of TMM, principles of TMM, traditional medicinal preparations, the Mongolian health care system, and the health situation in Mongolia. 1.1.1 Historical background of TMM TMM developed from Mongolian folk medicine and was highly influenced by the Traditional Tibetan Medicine and Ayurveda. During the 13th century, Mongolia came under the missionary influence of Lamaism.
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