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Table of Contents Bioactive Constituents of Two Medicinal Plants from Indonesia Dissertation Presented in Partial Fufillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School of The Ohio State University By Ye Deng, M.S. Graduate Program in Pharmacy The Ohio State University 2010 Dissertation Committee: A. Douglas Kinghorn, Advisor Esperanza Carcache de Blanco James R Fuchs Pui-Kai Li 1 Copyright by Ye Deng 2010 2 Abstract Natural products have played an important role in anticancer drug development for many decades. A recent review analyzing clinically approved anticancer drugs in Western countries and Japan during a twenty-five year period from 1981 to 2006 showed that, under the class of ―non-biologicals/vaccines‖, 63 of 81 (77.8%) anticancer drugs were either natural products or their derivatives, or synthesized molecules based on natural product pharmacophores. As part of a collaborative, multi-disciplinary approach to the discovery of new naturally occurring anticancer drugs, two medicinal plants, namely, Hyptis brevipes and Vitex quinata, collected in Indonesia, were selected for further investigation. The chloroform-soluble extract of a sample of the entire plant of H. brevipes showed activity against the MCF-7 human breast cancer cell line. Bioassay-guided fractionation and purification of the CHCl3-soluble extract of H. brevipes led to the isolation of six new 5,6-dihydropyrone derivatives, namely, brevipolides A-F (342-346), together with seven known compounds. Brevipolides A-F (342-346), and a previously ii ii known 5,6-dihydropyrone derivative (347), were assigned with the absolute configuration, 5R, 6S, 7S, and 9S, as elucidated by analysis of data obtained from their CD spectra and by Mosher ester reactions. Brevipolides B and D, as well as compound 347 exhibited ED50 values of 6.1, 6.7 and 3.6 M against MCF-7 cells. Brevipolides A, B, and F, and compound 349 (the known 5,6,3-trihydroxy-3,7,4-trimethoxyflavone) gave ED50 values of 5.8, 6.1 7.5, and 3.6 M against HT-29 cells, respectively. However, no significant cytotoxicity was found against Lu1 cells for any of the compounds isolated. When these compounds were subjected to evaluation in a panel of mechanism-based in vitro assays, compound 347 were found to be active in an enzyme-based ELISA NF-B p50 assay, with an ED50 value of 15.3 M. In a mitochondrial transmembrane potential assay, brevioplide C, compounds 348 and 349 showed ED50 values of 8.5, 75, and 310 nM, respectively. However, no potent activity was found in a proteasome inhibition assay for any of the isolated compounds. A phytochemical investigation of the chloroform-soluble and ethyl acetate-soluble extracts of the leaves of V. quinata led to the isolation of a new -truxinate derivative (378) and a new prostaglandin-like octadecanoid (379), together with 12 known compounds including flavonoids and quinic acid derivatives. All the isolates were tested iii iii in a panel of human cancer cells, and (S)-5-hydroxy-7,4-dimethoxyflavanone (384) was found to be an active principle with ED50 values of 6.7, 4.7, and 1.1 M against LNCaP (hormone-dependent prostate cancer), Lu1 (human lung cancer), and MCF-7 (human breast cancer) cell lines, respectively. Compounds 382 and 384-390 were tested in an enzyme-based ELISA NF-B p65 assay to evaluate their potential in inhibiting the binding of NF-B to DNA. Compounds 382, 384, 385, and 390 showed activity, with ED50 values of 22.8, 54.3, 17.8, 10.3 M, respectively. iv iv This dissertation is dedicated to my parents, my wife and son, and all of my family members who have encouraged and supported me to accomplish this work. v v Acknowledgments First of all, I would like to sincerely thank my advisor, Dr. A. Douglas Kinghorn, for his encouragement, generosity, guidance and support during the course of this study. I really appreciate for all the advice, help, and opportunities he has given to me. I also would like to thank Drs. Esperanza J. Carcache de Blanco, James R. Fuchs, and Pui-Kai Li for serving as members of my dissertation defense committee and for reviewing this dissertation. I would like to express my gratitude to Drs. Esperanza Carcache de Blanco and Heebyung Chai for providing data related to the NF-κB, mitochondrial transmembrane potential, and cytotoxicity assays used, as well as helping me to learn related bioassay techniques. I am grateful to Dr. Steven M. Swanson of the University of Illinois at Chicago for the result using the proteasomal inhibition assay. I wish to thank Drs. Young-Won Chin and Bao-Ning Su for training on the various instrumentation or bioassays, as well as guiding research and discussing problems. I also thank Drs. Angela A. Salim and Soyoung Kim who spent a lot of time to teach me the vi vi NMR instrumentation methods. One of the plants studied in this dissertation research was transferred from Dr. Marcy J. Balunas, formerly of the University of Illinois at Chicago. I am grateful to her for providing me the valuable sample and for completing some initial phytochemical work. This dissertation study was supported by grants U19 CA52956 and P01 CA125066 awarded to Dr. A Douglas Kinghorn, from the National Cancer Institute, National Institutes of Health (NCI, NIH), Bethesda, MD. The plant Hyptis brevipes was collected through grant P01 CA48112 awarded to Dr. John M. Pezzuto, formerly of the University of Illinois at Chicago, by NCI, NIH. All plant collections were supported through formal befefit sharing agreements that were approved by the U.S. National Cancer Institute. This research was also supported by the Raymond W. Doskotch Graduate Fellowship Fund in Medicinal Chemistry and Pharmacognosy from The Ohio State University. Other funding sources throughout my graduate work include teaching and research assistantships from the Division of Medicinal Chemistry and Pharmacognosy, The Ohio State University. I thank Mr. J. Fowble, College of Pharmacy, The Ohio State University, for facilitating the acquisition of the 300 and 400 MHz NMR spectra. We are grateful to the Mass Spectrometry and Proteomics Facility of the OSU CCIC, for the mass spectra. vii vii I am grateful to my friends and colleagues in the College of Pharmacy, especially former and present members of Dr. Kinghorn’s lab, Drs. Ah-Reum Han, William Jones, and Alison Pawlus, and Ms. Lynette Bueno, Mr. Mark Bahar, Mr. Josh Fletcher, Mr. Jie Li, and Mr. Patrick Still. My deepest gratitude and appreciation go to my parents for their love, inspiration, encouragement, and always supporting me. Words can not adequately express my gratitude towards my wife, Dr. Li Pan, who endured many sacrifices during my graduate study period and helped as a colleague in resolving various research problems together. I am grateful to my son, Yihan (Russell), for filling my life with joy and motivation. Furthermore, I wish to thank my brother, sister, and the rest of my family for their support and encouragement. viii viii Vita EDUCATION 1991-1994…………. A.E. Chemical Engineering, Hunan University of Science and Technology, Xiangtan, People’s Republic of China 1998-2001…………. M.S. Chengdu Institute of Biology, The Chinese Academy of Sciences, Chengdu, People’s Republic of China 2002-2004…………. Graduate student, Hong Kong Baptist University, Hong Kong SAR, People’s Republic of China 2004-2010…………. Graduate student, College of Pharmacy, The Ohio State University CAREER EXPERIENCE: 1994-1997…… Researcher, Guangli Resin Chemical Co. Ltd., Guang Dong, People’s Republic of China 1997-1998…… Teacher, the Affiliated Middle School of Hunan University of Science and Technology, Xiangtan, People’s Republic of China 2001-2002…… Associate Lecturer, Hunan University of Science and Technology, Xiangtan, People’s Republic of China. AWARDS AND HONORS 1. General Travel Grant, 2009, American Society of Pharmacognosy. 2. Raymond W. Doskotch Fellowship, 2007-2008, College of Pharmacy, The Ohio State University. 3. Nature Sunshine Travel Grant, 2007, American Society of Pharmacognosy. 4. Jack L. Beal Graduate Student Award, 2006, College of Pharmacy, The Ohio State University. 5. Liu Yongling Award, 2001, Chinese Academy of Sciences. 6. Excellent Student Award, 1994, Hunan University of Science and Technology. 7. Excellent Student Award, 1993, Hunan University of Science and Technology. 8. Excellent Student Award, 1992, Hunan University of Science and Technology. ix ix NATIONAL MEETING PRESENTATIONS 1. Y. Deng, M.J. Balunas, J.-A. Kim, D.D. Lantvit, Y.-W. Chin, H. Chai, S. Sugiarso, L.B.S. Kardono, H.H.S. Fong, J.M. Pezzuto, S.M. Swanson, E.J. Carcache de Blanco, A.D. Kinghorn. ―Bioactive 5,6-dihydropyrone derivatives from Hyptis brevipes‖. 50th Anniversary Meeting of American Society of Pharmacognosy; Honolulu, Hawaii, June 2009; oral presentation. 2. Y. Deng, Y.-W. Chin, H. Chai, W.J. Keller, A.D. Kinghorn. ―New benzophenone derivatives from Morinda citrifolia (Noni) roots‖. 48th Annual Meeting of American Society of Pharmacognosy; Portland, Maine, July 2007; poster presentation. 3. Y. Deng, H. Chai, Y.-W. Chin, L.B.S. Kardono, S.Riswan, N.R. Farnsworth, A.D. Kinghorn. ―New prostaglandin-like octadecanoid and cytotoxic flavonoids from the leaves of Vitex quinata‖. 47th Annual Meeting of American Society of Pharmacognosy; Arlington, VA, July 2006; poster presentation. Publications 1. Y. Deng, M.J. Balunas, J.-A. Kim, D.D. Lantvit, Y.-W. Chin, H. Chai, S. Sugiarso, L.B.S. Kardono, H.H.S. Fong, J.M. Pezzuto, S.M. Swanson, E.J. Carcache de Blanco, A.D. Kinghorn. Bioactive 5,6-dihydropyrone derivatives from Hyptis brevipes. Journal of Natural Products 2009, 72, 1165-1169. 2. M. Bahar, Y. Deng, J.N. Fletcher, A.D. Kinghorn. Plant-derived natural products. In drug discovery and development: an overview.
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