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Phytochemical Research on Two Ancistrocladus Species

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Phytochemical Research on Two Ancistrocladus Species Phytochemical Research on Two Ancistrocladus Species, Semi-Synthesis of Dimeric Naphthylisoquinoline Alkaloids, and Structure Optimization of Antitumoral Naphthoquinones Phytochemische Untersuchungen an zwei Ancistrocladus-Arten, Semi-Synthese dimerer Naphthylisochinolin-Alkaloide und Strukturoptimierung von antitumoralen Naphthochinonen Doctoral thesis for a doctoral degree at the Graduate School of Life Sciences, Julius-Maximilians-Universität Würzburg, Section: Infection and Immunity submitted by Guoliang Zhang from Jingmen, China Würzburg 2012 Submitted on: ______________________________________ Members of the Promotionskomitee: Chairperson: Prof. Dr. Thomas Dandekar Primary Supervisor: Prof. Dr. Dr. h.c. Gerhard Bringmann Supervisor (Second): Prof. Dr. Ulrike Holzgrabe Supervisor (Third): Prof. Dr. med. Ralf Bargou Date of Public Defence: ___________________________________________ Date of Receipt of Certificates: ___________________________________________ Die vorliegende Arbeit wurde in der Zeit von August 2008 bis Juli 2012 am Institut für Organische Chemie der Universität Würzburg angefertigt. Herrn Prof. Dr. Dr. h.c. G. Bringmann danke ich für die hervorragende Unterstützung bei dieser Arbeit, die freundliche Atmosphäre und die exzellenten Arbeitsbedingungen. Teile der im Rahmen dieser Arbeit erzielten Ergebnisse waren bereits Gegenstand von Publikationen sowie von Posterpräsentationen und Vorträgen. Dedicated to my family Contents General Introduction .......................................................................................... 1 1 Introduction .................................................................................................... 1 1.1 Natural Product Chemistry ................................................................................................. 1 1.2 Ancistrocladaceae and Dioncophyllaceae .......................................................................... 3 2 Multiple Myeloma and Naphthoquinones ................................................... 7 Results and Discussion ...................................................................................... 16 3 Isolation and Characterization of Naphthylisoquinoline Alkaloids from the Chinese Ancistrocladus tectorius Species ............................................ 16 3.1 Naphthylisoquinoline Alkaloids from A. tectorius .......................................................... 16 3.2 Results and Discussion ..................................................................................................... 18 3.3 Conclusion ....................................................................................................................... 29 4 Isolation and Characterization of Naphthylisoquinoline Alkaloids from a Congolese Ancistrocladus Species .............................................................. 30 4.1 Naphthylisoquinoline Alkaloids from an African Ancistrocladus Species ...................... 30 4.2 Results and Discussion ..................................................................................................... 31 4.3 Conclusion ....................................................................................................................... 36 4.4 Bioactivities of the New Naturally Occurring Alkaloids ................................................. 37 5 Semi-synthesis of Unprecedented Dimeric Naphthylisoquinoline Alkaloids ....................................................................................................... 40 5.1 Synthesis of Jozimine A2 (85) and its 3'-epi-Atropo-diastereomer (3'-epi-85) ............... 41 5.2 Synthesis of Jozimine A3 (93) ......................................................................................... 43 5.3 One-step Synthesis of Dioncotetralones A (94a) and B (94b) ......................................... 45 5.4 Further Semi-Syntheses from Dioncophylline A (6) ........................................................ 47 5.5 Bioactivities of the Synthetic Alkaloids ........................................................................... 48 6 Isolation and Characterization of Naphthoquinones from Cell Cultures of Triphyophyllum peltatum ......................................................................... 50 6.1 Compounds Isolated from Cell Cultures of T. peltatum .................................................. 50 6.2 T. peltatum ....................................................................................................................... 50 6.3 Results and Discussion ..................................................................................................... 51 6.4 Conclusion ....................................................................................................................... 54 7 Phytochemical Investigations on Nepenthaceae ....................................... 55 7.1 Introduction and Results .................................................................................................. 55 7.2 Conclusion ....................................................................................................................... 56 8 Synthesis of Dioncoquinones B (10) and C (102), and their Analogs ...... 57 8.1 Synthesis of Dioncoquinones B (10) and C (102) ........................................................... 57 8.2 Synthesis of Analogs of Dioncoquinone B (10) ............................................................... 61 8.3 SAR Studies of Prepared Naphthoquinones .................................................................... 64 8.4 Conclusion ....................................................................................................................... 67 9 Synthesis of Epoxides and SAR Studies ..................................................... 68 10 Total Synthesis of Triphoquinone (187a) ................................................. 71 10.1 Introduction .................................................................................................................... 71 10.2 Retrosynthetic Analysis .................................................................................................. 71 10.3 Synthesis of Biaryls ....................................................................................................... 72 10.4 Conclusion ..................................................................................................................... 77 11 Cyclodysidins A−D, Cyclic Lipopeptides from the Streptomyces Strain RV15 Derived from a Marine Sponge ..................................................... 78 11.1 Cyclic Peptides from Streptomyces Strain...................................................................... 78 11.2 Results and Discussion ................................................................................................... 78 11.3 Conclusion ...................................................................................................................... 82 12 Summary ..................................................................................................... 83 13 Zusammenfassung ..................................................................................... 92 Experimental Section ...................................................................................... 101 1 General Aspects .......................................................................................... 101 1.1 Analytical Apparatuses .................................................................................................. 101 1.2 Other Apparatuses ......................................................................................................... 102 1.3 Chromatographical Methods ......................................................................................... 103 1.4 Chemicals ...................................................................................................................... 103 1.5 Cell Cultures of T. peltatum .......................................................................................... 104 2 Phytochemical Investigation on A. tectorius ............................................ 106 2.1 Extraction and Isolation ................................................................................................. 106 2.2 Ancistectorine A1 (60) ................................................................................................... 108 2.3 N-Methylancistectorine A1 (61) ..................................................................................... 109 2.4 Ancistectorine A2 (62a) ................................................................................................. 110 2.5 5-epi-Ancistectorine A2 (62b) ....................................................................................... 111 2.6 4'-O-Demethylancistectorine A2 (63) ............................................................................ 112 2.7 Ancistectorine A3 (64) ................................................................................................... 113 2.8 Ancistectorine B1 (65) ................................................................................................... 114 2.9 Ancistectorine C1 (66) ................................................................................................... 115 2.10 5-epi-Ancistrolikokine D (67) ...................................................................................... 116 2.11 Known Alkaloids .........................................................................................................
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