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Separation and Identification of Bioactive Compounds from Oplopanax Horridus Christina Nicole Bailey Clemson University

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Separation and Identification of Bioactive Compounds from Oplopanax Horridus Christina Nicole Bailey Clemson University Clemson University TigerPrints All Theses Theses 5-2015 Separation and Identification of Bioactive Compounds from Oplopanax horridus Christina Nicole Bailey Clemson University Follow this and additional works at: https://tigerprints.clemson.edu/all_theses Recommended Citation Bailey, Christina Nicole, "Separation and Identification of Bioactive Compounds from Oplopanax horridus" (2015). All Theses. 2090. https://tigerprints.clemson.edu/all_theses/2090 This Thesis is brought to you for free and open access by the Theses at TigerPrints. It has been accepted for inclusion in All Theses by an authorized administrator of TigerPrints. For more information, please contact [email protected]. SEPARATION AND IDENTIFICATION OF BIOACTIVE COMPOUNDS FROM OPLOPANAX HORRIDUS A Thesis Presented to the Graduate School of Clemson University In Partial Fulfillment of the Requirements for the Degree Master of Science Food, Nutrition and Culinary Science by Christina Nicole Bailey May 2015 Accepted by: Dr. Feng Chen, Committee Chair Dr. Gregory Batt Dr. Elliot Jesch ABSTRACT For centuries, natural products, such as plants, have been used for the prevention and treatment of diseases and ailments. Modern science is now working to identify the beneficial compounds from these sources to implement into pharmaceutical drugs, vitamins or supplements in an area of study called nutraceuticals. The plant Oplopanax horridus, or Devil’s Club is a member of the ginseng family and has over 30 documented uses for spiritual and medicinal purposes. The few studies that have been carried out on this plant are limited to the volatile chemicals present. Few studies have determined the plant possesses antifungal, antioxidant and antimicrobial properties but without confirmation of the chemical compounds responsible for these properties. The purpose of this study was to fractionate compounds from a crude sample of Oplopanax horridus by solid phase extraction (SPE) with the assistance of high pressure liquid chromatography (HPLC). These fractions were subjected to antioxidant testing where bioactivity guided further fractionation and analysis by mass spectrometry (MS). The data collected from the mass spectrophotometer was used to propose the chemical compounds present in the antioxidant active samples. Successful separation of natural products was completed by Soxhlet extraction, liquid-liquid extraction, SPE, and HPLC. Three sample sub-fractions were found to be bioactive after the assessment of antioxidant activity with two variations of assays. Mass spectrum data produced ion chromatograms that were useful in the prediction of chemical structures. ii DEDICATION I would like to dedicate herein to my family for their unconditional love and support throughout my life. To my parents, David and Linda Bailey, for instilling in me the values of education, determination and hard-work; without these traits I would not be where I am today. Mom and dad you have always encouraged me to achieve my dreams and you’ve always stood by me as I’ve made my way through life. To my sister, Stephanie Hiett, for paving the way for me to become a scientist and for your wisdom of lessons and advice learned through your experiences. You have always been my sister but through the years you have become my friend. THANKFUL. iii ACKNOWLEDGMENTS First, I’d like to acknowledgement Dr. Feng Chen, my research advisor, for allowing me to be a part of his research group as a creativity inquiry and graduate student. I appreciate the opportunity you gave me to further my education in the field of food science. I would like to thank the other members of my committee for their time and assistance, Dr. Greg Batt and Dr. Elliot Jesch. I would like the acknowledge Dr. Gregory Jones for all of his assistance and guidance throughout my research progress. I greatly appreciate the time you spent training and educating me about instruments and research methods. Thank you for convincing me to return to school and for countless other matters. I want to say thank you to those who assisted in data analysis including Benjamin Sharp, the director of the statistics and mathematics consulting center. And David Hiett for answering my questions about Excel over the years. iv TABLE OF CONTENTS Page TITLE PAGE .................................................................................................................... i ABSTRACT ..................................................................................................................... ii DEDICATION ................................................................................................................ iii ACKNOWLEDGMENTS .............................................................................................. iv LIST OF TABLES ......................................................................................................... vii LIST OF FIGURES ........................................................................................................ ix CHAPTER I. Literature Review........................................................................................... 1 Oplopanax horridus ................................................................................. 1 Natural products ....................................................................................... 2 Polyphenols .............................................................................................. 3 Antioxidants ............................................................................................. 3 Antioxidant testing ................................................................................... 4 Sample preparation .................................................................................. 7 Soxhlet extraction .................................................................................... 8 Liquid-liquid extraction ........................................................................... 9 Solid phase extraction .............................................................................. 9 High pressure liquid chromatography .................................................... 11 Mass spectrometry ................................................................................. 16 Research Objectives ............................................................................... 18 References .............................................................................................. 20 II. Sample Preparation ...................................................................................... 24 Introduction ............................................................................................ 24 Experimental .......................................................................................... 26 Results .................................................................................................... 31 Discussion .............................................................................................. 44 References .............................................................................................. 50 III. Antioxidant Testing ..................................................................................... 52 Introduction ............................................................................................ 52 v Table of Contents (Continued) Page Experimental .......................................................................................... 55 Results .................................................................................................... 58 Discussion .............................................................................................. 73 References .............................................................................................. 78 IV. Analytical Methods ...................................................................................... 80 Introduction ............................................................................................ 80 Experimental .......................................................................................... 82 Results .................................................................................................... 84 Discussion ............................................................................................ 106 References ............................................................................................ 117 vi LIST OF TABLES Table Page 2.1 LLE fractionation of crude methanol ........................................................... 31 2.2 Fraction concentrations from crude ethyl acetate ........................................ 31 2.3 Separation method used for HLB-SPE cartridge ......................................... 32 2.4 Separation method used for WCX-SPE cartridge ........................................ 32 2.5 SPE fractionation of EtOAc fraction 1 (Et-1) .............................................. 33 2.6 SPE fractionation of EtOAc fraction 2 (Et-2) .............................................. 34 2.7 SPE fractionation of EtOAc fraction 3 (Et-3) .............................................. 35 2.8 SPE fractionation of EtOAc fraction 4 (Et-4) .............................................. 36 2.9 SPE fractionation of EtOAc fraction 5 (Et-5) .............................................. 37 2.10 SPE fractionation of EtOAc fraction 6 (Et-6) .............................................. 38 2.11 SPE fractionation of EtOAc fraction 7 (Et-7) .............................................
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