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INAUGURAL DISSERTATION Florian Herrmann

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INAUGURAL DISSERTATION Florian Herrmann INAUGURAL DISSERTATION submitted to the Combined Faculties for the Natural Sciences and for Mathematics of the Ruperto-Carola University of Heidelberg, Germany for the degree of Doctor of Natural Sciences Presented by Florian Herrmann Apotheker (Staatsexamen) born in Karlsruhe, Germany Oral examination: 12.10.2011 TCM Plants: DNA Barcoding, Cytotoxic and Trypanocidal Properties of Drugs and Their Active Constituents This work was carried out in the Department of Biology, Institute for Pharmacy and Molecular Biotechnology (IPMB), Im Neuenheimer Feld 364, 69120 Heidelberg at the Ruprecht-Karls-University of Heidelberg between February 2006 and August 2011. Head of division: Prof. Dr. Michael Wink Supervisor: Prof. Dr. Michael Wink Department of Biology, IPMB Ruprecht-Karls-University Heidelberg 1st Referee: Prof. Dr. Michael Wink Department of Biology, IPMB Ruprecht-Karls-Universiität Heidelberg 2nd Referee: Prof. Dr. Thomas Efferth Institute for Pharmacy and Biochemistry Johannes Gutenberg-Universität Mainz 2 Publications F. Herrmann , R. Hamoud, F. Sporer, A. Tahrani, M. Wink: Carlina oxide – a natural polyacetylene from Carlina acaulis (Asteraceae) with potent antitrypanosomal and antimicrobial properties! In press, Planta Medica; published online June 15, 2011 DOI http://dx.doi.org/10.1055/s-0031-1279984 F. Herrmann , M. Wink: Synergistic interactions of saponins and monoterpenes in HeLa cells, Cos7 cells and in erythrocytes In press, Phytomedicine F. Herrmann , F. Sporer, A. Tahrani, M. Wink: Antitrypanosomal properties of Panax ginseng CA Meyer – new possibilities for a remarkable traditional drug! Submitted, Phytotherapy Research F. Herrmann , M. Wink: Cytotoxicity of structurally diverse ginsenosides from Panax ginseng in HeLa cells is linked to membrane disturbances Submitted, Journal of Pharmacy and Pharmacology F Herrmann , M. R. Romero, A.G. Blazquez, D. Kaufmann, M. L. Ashour, S. Kahl, J.J.G. Marin, T. Efferth, M. Wink: Cytotoxicity, antiviral and antitrypanosomal screening of 82 plants from Chinese and European phytomedicine Submitted, Diversity F. Herrmann , M. Wink: Use of rbc L sequences for DNA barcoding and authentication of plant drugs used in Traditional Chinese Medicine Submitted, Zeitschrift für Naturforschung N.Z. Mamadalieva §, F. Herrmann §, M.Z. El-Readi, A. Tahrani, R. Hamoud, D. Egamberdieva, Sh.S. Azimova, M. Wink: Flavonoids in Scutellaria immaculata and S. ramosissima and their biological activities In press, Journal of Pharmacy and Pharmacology §Equal distributed authors 3 T. Efferth, F. Herrmann , A. Tahrani, M. Wink: Cytotoxic activity towards cancer cells of arteanuine B, artemisitene, scopoletin and 1.8-cineole derived from Artemisia annua L. in comparison to artemisinin In press, Phytomedicine 2011 DOI 10.1016/j.phymed.2011.06.008 D. Hamdan, M. Z. El-Readi, A. Tahrani, F. Herrmann , D. Kaufmann, N. Farrag, A. El-Shazly, M. Wink: Chemical composition and biological activity of Citrus jambhiri Lush. Food Chemistry 2011, 127: 394-403 D. Hamdan, M. Z. El-Readi, A. Tahrani, F. Herrmann , D. Kaufmann, N. Farrag, A. El-Shazly, M. Wink: Secondary metabolites of ponderosa lemon (Citrus pyriformis Hassk) and their antioxidant, anti-inflammatory and cytotoxic activities In press, Zeitschrift für Naturforschung 2011 S. Mulyaningsih, M. Youns, M. Z. El-Readi, M. L. Ashour, E. Nibret, F. Sporer, F. Herrmann , J. Reichling, M. Wink: Biological activity of the essential oil of Kadsura longipedunculata (Schisandraceae) and its major components Journal of Pharmacy and Pharmacology 2010, 62: 1037–1044 4 Table of Contents Summary ………………...………………………………………………………………..….…....7 Summary (German) ……………………………………………………………………...………..8 1. General Introduction …………………………………………...………...…………….………9 1.1 Traditional Chinese Medicine……………………………………………….………..9 1.1.1 Traditional Chinese Medicine…………………………………….……………...9 1.1.2 Chinese herbal medicine………………………………………………………..11 1.2 Secondary metabolites………………………………………………………………12 1.2.1 Ecological function…………………………………………………………...12 1.2.2 Biosynthesis…………………………………………………………………..12 1.2.3 Storage………………………………………………………………………..12 1.2.4 Classes of secondary metabolites……………………………………………….13 1.2.5 Mode of action………………………………………………………………..14 1.3 African Trypanosomiasis……………………………………………………………17 1.3.1 Epidemiology…………………………………………………………………17 1.3.2 Classification……………………………………………………………………17 1.3.3 Biology………………………………………………………………………..17 1.3.4 Control………………………………………………………………………..19 1.3.5 Targets……...………...……………………………………………………….21 1.4 References…………………………………………………………………………...24 2. Use of rbc L sequences for DNA barcoding and authentication of plant drugs used in Traditional Chinese Medicine ………………..………………………...……………………….31 2.1 Abstract……………………………………………………………………………...31 2.2 Introduction………………………………………………………………………….31 2.3 Material and Methods……………………………………………………………….34 2.4 Results……………………………………………………………………………….34 2.5 Discussion…………………………………………………………………………...36 2.6 References…………………………………………………………………………...42 3. Cytotoxicity, antitrypanosomal and antiviral screening of 82 plants from Chinese and European phytomedicine ………………………..………………………………………………45 3.1 Abstract……………………………………………………………………………...45 3.2 Introduction………………………………………………………………………….45 3.3 Material and Methods……………………………………………………………….48 3.4 Results and Discussion……………………………………………………………...56 3.5 References…………………………………………………………………………...74 5 4. Cytotoxicity of 12 structurally diverse ginsenosides from Panax ginseng in HeLa cells is linked to membrane disturbance …………………………...………...…………………………81 4.1 Abstract……………………………………………………………………………...81 4.2 Introduction………………………………………………………………………….81 4.3 Material and Methods……………………………………………………………….84 4.4 Results……………………………………………………………………………….85 4.5 Discussion…………………………………………………………………………...85 4.6 References…………………………………………………………………………...91 5. Antitrypanosomal properties of Panax ginseng CA Meyer – new possibilities for a remarkable traditional drug! .......................................................................................................95 5.1 Abstract……………………………………………………………………………...95 5.2 Introduction………………………………………………………………………….95 5.3 Material and Methods……………………………………………………………...101 5.4 Results…………………………………………………………………………..….105 5.5 Discussion……………………………………………………………………….....107 5.6 References………………………………………………………………………….116 6. Carlina oxide – a natural polyacetylene from Carlina acaulis (Asteraceae) with potent antitrypanosomal and antimicrobial properties! ......................................................................126 6.1 Abstract…………………………………………………………………………….136 6.2 Introduction………………………………………………………………………...126 6.3 Material and Methods……………………………………………………………...127 6.4 Results……………………………………………………………………………...132 6.5 Discussion………………………………………………………………………….133 6.6 References………………………………………………………………………….138 7. Synergistic Interactions of Saponins and Monoterpenes in HeLa cells, Cos7 Cells and in Erythrocytes .…………………...…………………………………...…………………………..141 7.1 Abstract…………………………………………………………………………….141 7.2 Introduction………………………………………………………………………...141 7.3 Material and Methods……………………………………………………………...144 7.4 Results……………………………………………………………………………...146 7.5 Discussion………………………………………………………………………….148 7.6 References………………………………………………………………………….157 8. General conclusion and outlook ………………………………………..…………………...160 9. Acknowledgements …..………………………………………………..……………………..163 10. Appendix ………………………………………………………………………..…………...165 6 Summary Our extensive screening of 82 herbal drugs used in traditional Chinese and European Phytomedicine revealed the great potential still hidden in this field of research. The correct authentication of plants used in research on traditional medicinal systems such as TCM is crucial before any serious research can be started. DNA barcoding offers a reliable, fast possibility to overcome this obstacle. Only one adulteration could be detected where Arctium lappa was wrongly labelled Fraxinus rhynchophylla . After screening 246 extracts of herbal drugs against a variety of targets such as trypanosomes, viruses and cancer cells we were able to select several highly promising plants for further research. We decided to focus our research on Panax ginseng , Araliaceae, a well known herbal medicine of international fame and a long history of traditional use. Our experiments revealed that ginsenosides, a highly variable group of saponins, disturb the biomembrane of cells, while the exact position of the sugar moieties and the resulting ability to be incorporated into the lipid bilayer of the cell membrane explain the great differences in their cytotoxicity. The membrane activity of the ginsenosides however was not responsible for the trypanocidal effect of ginseng revealed in our screening. Panaxynol, the major polyacetylene of ginseng was with an IC 50 concentration of 0.01 µg/ml and a selectivity index of 858 three times as selective against Trypanosoma brucei brucei as established antitrypanosomal drugs like suramin. We were able to discover with Carlina oxide isolated from Carlina acaulis , Asteraceae, a second polyacetylene highly selective in its cytotoxicity against T. b. brucei with an IC 50 of 1.0 µg/ ml and a selectivity index of 446. We suggest that the inhibition of the trypanothione reductase, essential for the resistance of the parasite against oxidative stress and unique to trypanosomes, is the primary principle of this selectivity. Our previous results obtained from the activity of ginsenosides had shown us the efficacy, but also the structure dependency of the membrane effects
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