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Biological and Chemical Investigation of Panamanian Plants for Potential Utility Against Metabolic Syndrome

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Biological and Chemical Investigation of Panamanian Plants for Potential Utility Against Metabolic Syndrome University of Mississippi eGrove Electronic Theses and Dissertations Graduate School 1-1-2016 Biological and Chemical Investigation of Panamanian Plants for Potential Utility against Metabolic Syndrome Yelkaira Vasquez University of Mississippi Follow this and additional works at: https://egrove.olemiss.edu/etd Part of the Pharmacy and Pharmaceutical Sciences Commons Recommended Citation Vasquez, Yelkaira, "Biological and Chemical Investigation of Panamanian Plants for Potential Utility against Metabolic Syndrome" (2016). Electronic Theses and Dissertations. 1507. https://egrove.olemiss.edu/etd/1507 This Dissertation is brought to you for free and open access by the Graduate School at eGrove. It has been accepted for inclusion in Electronic Theses and Dissertations by an authorized administrator of eGrove. For more information, please contact [email protected]. BIOLOGICAL AND CHEMICAL INVESTIGATION OF PANAMANIAN PLANTS FOR POTENTIAL UTILITY AGAINST METABOLIC SYNDROME A Dissertation presented in partial fulfillment of requirements for the degree of Doctor of Philosophy in the Department of BioMolecular Sciences Division of Pharmacognosy The University of Mississippi by YELKAIRA VASQUEZ August 2016 Copyright © 2016 by Yelkaira Vasquez ALL RIGHTS RESERVED ABSTRACT Metabolic syndrome (MetS) affects approximately 25% of the adult population of the world and represents a public health concern with high socioeconomic impact worldwide. Latin American populations exhibit a high prevalence of MetS, similar or even higher than developed countries. This complex and progressive disorder can develop over many years as a cluster of conditions characterized by a constellation of metabolic abnormalities. Specific guidelines have not yet been established for the treatment of MetS per se. The increased prevalence of MetS has been associated with a greater risk of developing type 2 diabetes mellitus (T2DM) and cardiovascular disease (CVD). In fact, new anti-diabetic drugs that do not display undesirable side effects, such as hepatotoxicity, edema and weight gain, are in great demand. For these reasons, the overall goal of this study was centered on four molecular targets: peroxisome proliferator-activated receptors (PPARs), liver X receptors (LXRs), nuclear factor-κB (NF-κB), and inducible nitric oxide synthase (iNOS) which are key regulators of various processes leading to metabolic disorder and inflammation. As a part of inflammatory pathway, activation of NF-κB leads to insulin resistance and by blocking this pathway, insulin resistance and the resultant T2DM can be prevented. In contrast, activators of PPAR and PPAR are effective in lowering blood lipids and sugar and have been considered useful in the treatment of obesity and diabetes. Like the PPARs, LXR suppresses production of inflammatory mediators in a manner reciprocal to its regulation of lipid metabolism. In order to explore natural products working through these ii specific pathways this dissertation was focused on Panamanian flora as a primary source. A total of 75 plant species belonging to 71 genera and 41 families were screened for their effects on the selected targets trough cellular assays. Due to a lack of literature available on the biological activity towards MetS and lack of the phytochemical characterization, two plants (Talisia nervosa and Odontadenia puncticulosa) were selected for bioassay-guided fractionation through PPARα and PPARγ activation assay. The current study relied on Panamanian flora as a source of new therapeutic agents directed toward the mitigation of metabolic abnormalities. iii DEDICATION This dissertation is dedicated in memory of my mother, Paulina de Vasquez, who always gave me her unconditional love and encouraged me to follow my dreams. To my dad Ramiro Vasquez, who raised us alone and has been my source of inspiration. To my siblings Paulina and Ramiro who have been so supportive and courageous. To my Lord God for the unlimited blessings. iv LIST OF ABBREVIATIONS AND SYMBOLS °C Degrees Celsius AACE American Association of Clinical Endocrinology AF Activation Function AHA/NHLBI American Heart Association/National Heart, Lung, and Blood Institute ASE Accelerated Solvent Extractor ATCC American Type Culture Collection BCS Bovine Calf Serum BuOH Butanol CHCl3 Chloroform CIFLORPAN Center for Pharmacognostic Research on Panamanian Flora CO2 Carbon Dioxide COSY Correlation Spectroscopy CVD Cardiovascular Disease CYTED Iberoamerican Program of Science and Technology for Development DBD DNA Binding Domain DMEM Dulbecco's Modified Eagle's Medium DMSO Dimethyl Sulfoxide DNA Deoxyribonucleic Acid v EGCG Epigallocatechin Gallate EGIR European Group for the Study of Insulin Resistance eNOS Endothelial NOS EPA Eicosapentaenoic Acid EtOAc Ethyl Acetate EtOH Ethanol FAD Flavin Adenine Dinucleotide FBS Fetal Bovine Serum FDA Food and Drug Administration FI Fluorescence Intensity FMN Flavin Mononucleotide FXR Farnesoid X Receptor g. Gram GC-MS Gas Chromatography-Mass Spectrometry H2O Water H2SO4 Sulfuric Acid h. Hour HDL High-Density Lipoprotein HepG2 Human Hepatoma HMBC Heteronuclear Multiple-Bond Correlation Spectroscopy vi HPTLC High-Performance Thin-Layer Chromatography HRESITOFMS High-Resolution Electrospray Ionization Time of Flight Mass Spectrometry HSQC Heteronuclear Single-Quantum Correlation Spectroscopy IC50 Inhibitory Concentration, 50% IDF International Diabetes Federation IFN- γ Interferon-γ IKK IκB Kinase IL Interleukin iNOS Inducible Nitric Oxide Synthase IκB Inhibitors of NF-κB LBD Ligand Binding Domain LDL Low-Density Lipoprotein LPS Lipopolysaccharide LXREs LXR-Response Elements LXRs Liver X Receptors MeOH Methanol MetS Metabolic syndrome mg Milligram MHz Megahertz vii min. Minute mL Milliliter mM Millimole msec. Millisecond NADPH Nicotinamide-Adenine-Dinucleotide Phosphate NCEP:ATPIII National Cholesterol Education Program Adult Treatment Panel III NCNPR National Center for Natural Products Research NF-κB Nuclear Factor-κB NHANES National Health and Examination Survey NHR Nuclear Hormone Receptor nM Nanomole nm Nanometer NMR Nuclear Magnetic Resonance nNOS Neuronal NOS NO Nitric Oxide NOS Nitric oxide synthases NSAIDs Non-Steroidal Anti-Inflammatory PBS Phosphate-Buffered Saline PMA Phorbol 12-Myristate 13-Acetate PPARs Peroxisome Proliferator-Activated Receptors viii PPREs Peroxisome Proliferator Response Elements PXR Pregnane X Receptor RAW 264.7 Mouse Macrophage Rel Reticuloendotheliosis ROESY Rotating Frame Nuclear Overhauser Effect Spectroscopy ROS Reactive Oxygen Species RPMI Medium Roswell Park Memorial Institute Medium RXR Retinoid X Receptor Sp1 Specificity Protein 1 SW1353 Human Chondrosarcoma T2DM Type 2 Diabetes Mellitus TNFα Tumor Necrosis Factor-α VLDL Very-Low-Density Lipoprotein WHO World Health Organization µg Microgram µL Microliter µM Micromole 2-NBDG 2-[N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl) amino]-2-deoxy-D-glucose 3T3-L1 Mouse Embryo Preadipocyte ix ACKNOWLEDGEMENTS This dissertation would not have been possible without the help, guidance, and love of many people throughout my academic and personal experience here at the University of Mississippi. First and foremost, I would like to express my deepest gratitude to my advisor and mentor, Dr. Ikhlas A. Khan, for giving me the wonderful opportunity to work in his multidisciplinary research group, as well as for his invaluable guidance, constant support, endless encouragement, infinite patience, and for believing I could complete this exceptional journey that I had dreamed several years ago even when I doubted without him I could not have been able to achieve this goal. I would also like to thank my co-advisor Dr. Shabana I. Khan, for her precious orientation in my research work, warm kindness, immense care, always available to help me anytime, as well as her huge input that have allowed me to develop my scientific skills and critical thinking. It was a great honor to work with them and I am forever grateful. A special appreciation is due to my committee members: Dr. Stephen J. Cutler, who always offered me his helpful comments, advice, constructive guidance and trust in my capability to finish this Ph. D. program; Dr. Larry A. Walker, for his charming personality, warm encouragement, and valuable insights; Dr. Jordan K. Zjawiony, for his timely suggestions, interest and ready availability when I needed him. Thanks to all of them for sharing their valuable knowledge and precious time with me. I would like to express my deepest appreciation to Dr. Mahabir Gupta for his believe in x my capacity and his guidance, as well as his constant support that was a big motivation for me. Thank you from the bottom of my heart for all your care, kindliness, and concern about my future during all these years. I could not be here without you. I have no words to thank Dr. Amar Chittiboyina for his patience, guidance, and friendship during this entire journey and for being available all the time I needed him. My sincere appreciation goes to Dr. Jon Parcher for his support and constant help on my writing, as well as his valuable friendship. I would like to express my heartfelt appreciation to the faculty members in the Division of Pharmacognosy: Dr. Daneel Ferreira, Dr. Mark T. Hamann, Dr. Marc Slattery, Dr. Dale G. Nagle, and Dr. Yu-Dong Zhou for sharing their valuable knowledge and providing constant support. I wish to also extend thanks to the professors, staff and students, both past and present, in the BioMolecular Science department for providing me a welcoming, supportive and meaningful
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