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Isolation and Synthesis of Bioactive Compounds from Plants Alexander L. Eaton Dissertation submitted to the faculty of the Virginia Polytechnic Institute and State University in partial fulfillment of the requirements for the degree of Doctor of Philosophy In Chemistry David G. I. Kingston Paul R. Carlier Richard D. Gandour Webster L. Santos September 21, 2015 Blacksburg, VA Keywords: Natural Products, Antiproliferative, Antimalarial, Anti-inflammatory, Trihydroxyalkylcyclohexenones, Diterpene, Triterpene, Bis-5-alkylresorcinol, Synthesis Isolation and Synthesis of Bioactive Compounds from Plants Alexander L. Eaton ABSTRACT As a part of a continuing search for bioactive compounds with the International Cooperative Biodiversity Group (ICBG), and in collaboration with the Natural Products Discovery Institute of the Institute for Hepatitis and Virus Research (IHVR), twelve plant extracts were investigated for their antiproliferative activity against the A2780 cell line, three plant extracts were investigated for their antimalarial activity against Plasmodium falciparum, and three plant extracts were investigated for their anti-inflammatory activity (PPAR- inhibition). Bioassay-guided fractionation of extracts led to the identification of four new antiproliferative compounds (2.1–2.3, 3.1), five new anti-inflammatory compounds (6.4a, 6.5a–b, 6.6a, 6.6c), and twenty-eight known compounds from eight of the extracts. In addition, mallotojaponin C, an antimalarial natural product, and derivatives were synthesized and investigated for their antimalarial activity. ACKNOWLEDGEMENTS Firstly, I would like to thank my advisor, Dr. David G. I. Kingston, for his invaluable mentorship and encouragement. He has helped me become a better scientist and support my career goals, while being an example of a Christian leader. I would also like to thank Dr. Liva Harinantenaina, who provided mentorship and assistantship in the laboratory. He taught me the basics of natural products isolation and structure elucidation. Also, I am very grateful to Peggy Brodie for the many assays she performed and for teaching me how to perform an assay and maintain a cell line. Thank you to Dr. Maria Belen Cassera and her group for performing the antimalarial assays discussed within. Thank you to Dr. Josep Bassaganya-Riera and his group for PPAR- assays. I would also like to thank the many other collaborators who assisted with the collection, identification, and extraction of the plants investigated. This work would not have been possible without the Virginia Tech Analytical Services Department. I would also like to thank my parents for their unwavering support from across the country and Xinyan Leng for her support and encouragement. During my time at Virginia Tech I have made many friendships that I am grateful for and I hope they continue. These include those I have met in the chemistry department, at Intervarsity Christian Fellowship, and members of the Kingston group iii Table of Contents ABSTRACT ................................................................................................................................... iii ACKNOWLEDGEMENTS ........................................................................................................... iii Table of Contents ........................................................................................................................... iv List of Figures ............................................................................................................................ xviii List of Tables .............................................................................................................................. xxii List of Schemes .......................................................................................................................... xxiv Chapter 1: Introduction ................................................................................................................... 1 1.1 Importance of Natural Products ....................................................................................... 1 1.1.1 Anticancer Agents ..................................................................................................... 2 1.1.2 Antimalarial Agents .................................................................................................. 3 1.1.3 Anti-inflammatory Agents ........................................................................................ 6 1.2 Sources of Natural Products ............................................................................................. 8 1.2.1 Madagascar ICBG Project ........................................................................................ 8 1.2.2 Merck Collection at NPDI ........................................................................................ 8 1.3 Isolation of Bioactive Compounds ................................................................................... 9 1.3.1 Bioassay-guided Fractionation.................................................................................. 9 1.3.2 Antiproliferative Bioassay ........................................................................................ 9 1.3.3 Antimalarial Bioassay ............................................................................................. 10 1.3.4 Anti-inflammatory Bioassay ................................................................................... 11 1.3.5 Isolation Methods.................................................................................................... 11 1.3.6 Structure Elucidation .............................................................................................. 11 1.3.7 Problems ................................................................................................................. 12 1.4 Dereplication Strategies ................................................................................................. 12 1.4.1 Development of Dereplication ................................................................................ 12 iv 1.4.2 Solid Phase Extraction ............................................................................................ 12 1.4.3 Mass Spectrometry.................................................................................................. 13 1.4.4 Nuclear Magnetic Resonance Spectroscopy ........................................................... 14 1.4.5 High Performance Liquid Chromatography ........................................................... 17 1.4.6 HPLC Detection Methods ....................................................................................... 19 1.4.7 Database Searches ................................................................................................... 22 1.5 Synthetic Approaches ..................................................................................................... 23 1.6 References ...................................................................................................................... 25 Chapter 2: Antiproliferative Trihydroxyalkylcyclohexenones from Pleiogynium timoriense ..... 36 2.1 Introduction .................................................................................................................... 36 2.1.1 Abstract ................................................................................................................... 36 2.1.2 Author Contributions .............................................................................................. 37 2.1.3 Previous Investigations of Pleiogynium timoriense ................................................ 37 2.1.4 Chemical Investigation of Pleiogynium timoriense ................................................ 37 2.2 Results and Discussion ................................................................................................... 38 2.2.1 Isolation of Compounds from Pleiogynium timoriense .......................................... 38 2.2.2 Structure Elucidation .............................................................................................. 39 2.2.3 Antiproliferative Activity........................................................................................ 44 2.3 Experimental Section ..................................................................................................... 44 2.3.1 General Experimental Procedures ........................................................................... 44 2.3.2 Plant Material .......................................................................................................... 45 2.3.3 Extraction and Isolation .......................................................................................... 45 2.3.4 Antiproliferative Bioassay ...................................................................................... 45 2.3.5 Spectroscopic Properties ......................................................................................... 46 2.4 References ...................................................................................................................... 49 v Chapter 3: Bioactive Diterpene Glycosides from Molinaea retusa from the Madagascar Dry Forest ....................................................................................................................................................... 53 3.1 Introduction .................................................................................................................... 53 3.1.1 Abstract ..................................................................................................................
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