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Identifying Bioactive Phytochemicals in Spent Coffee Grounds for Cosmetic Application Through Global Metabolite Analysis

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Identifying Bioactive Phytochemicals in Spent Coffee Grounds for Cosmetic Application Through Global Metabolite Analysis IDENTIFYING BIOACTIVE PHYTOCHEMICALS IN SPENT COFFEE GROUNDS FOR COSMETIC APPLICATION THROUGH GLOBAL METABOLITE ANALYSIS _______________________________________ A Thesis Presented to the Faculty of the Graduate School University of Missouri-Columbia _______________________________________________________ In Partial Fulfillment of the Requirements for the Degree Master of Science _____________________________________________________ by JIHYUN PARK Dr. Chung-Ho Lin, Thesis Supervisor DECEMBER 2017 The undersigned, appointed by the dean of the Graduate School, have examined the thesis entitled: IDENTIFYING BIOACTIVE PHYTOCHEMICALS IN SPENT COFFEE GROUNDS FOR COSMETIC APPLICATION THROUGH GLOBAL METABOLITE ANALYSIS presented by JIHYUN PARK a candidate for the degree of Master of Science and hereby certify that in their opinion it is worthy of acceptance Professor Chung-Ho Lin Professor Shibu Jose Professor Gary Stacey Professor Minviluz Stacey ACKNOWLEDGEMENTS I would like to thank my advisor, Professor Chung-Ho Lin about his guidance with huge effort, and the Center for Agroforestry, without their considerable assistant, I could not have done this research. Conducting this project provided me a great opportunity to meet and work with many people who have a comprehensive mind and passion. It is very pleasure for me to offer thanks to them. In addition, my thesis committee members, Dr. Shibu Jose, Gary Stacey, and Bing Stacey, were the most responsible professors in their field and they leading me to focus on this research. They realized the novelty of my thesis topics paying attention to this project and encouraging me to accomplish the experiment on time. Also I would like to say thanks to Nahom Taddese Ghile who gave me the first help beginning this project and the laboratory members Van Ho, Danh Vu, Phuc Vo, who provided assistance in several steps of my experiment with familiarity. Special thanks to many capable professionals Zhentian Lei, Lloyd Summer, Michael Greenlief, Brian P. Mooney in metabolomics center and department of chemistry. Lastly I would like to thank to my family and friends who continuously supported me with their love. ii TABLE OF CONTENTS ACKNOWLEDGEMENTS ............................................................................................................. ii LIST OF TABLES ........................................................................................................................... v LIST OF FIGURES ........................................................................................................................ vi Chapter 1. Identifying the bioactive compounds in SCG through global metabolomics analysis (XCMS) ............................................................................................................................ 1 1. Introduction .............................................................................................................................. 2 2. Objectives .............................................................................................................................. 11 3. Materials and Methods ........................................................................................................... 11 3.1. Sample preparation ..............................................................................................12 3.2. LCMS Analysis ...................................................................................................12 3.3 Global metabolite profiling using XCMS and METLIN Library ........................15 4. Results .................................................................................................................................... 18 4.1. Multi-group Comparison between three SCG cultivars using low resolution data .............................................................................................................................19 4.2. Identified bioactive compounds through global metabolomics analysis using high resolution data ....................................................................................................28 5. Discussion .............................................................................................................................. 42 5.1. Global metabolomics approach (XCMS Online) vs traditional analytical techniques ...................................................................................................................42 5.2. Phenolic acids and caffeine in SCG ....................................................................45 5.3. Glycosylated form of flavonoids and their activity .............................................47 5.4. Flavonoids (flavonols, flavones, isoflavones, flavanones, anthocyanidins, and flavanols) in SCG for cosmetic application ................................................................48 6. Conclusion ............................................................................................................................. 54 Chapter 2. Isolation of the antioxidant and antimicrobial compounds with bioassay-guided fractionation ................................................................................................................................. 56 1. Introduction ............................................................................................................................ 57 2. Objectives .............................................................................................................................. 67 3. Materials and Methods ........................................................................................................... 67 3.1. Explore new application (antioxidant and antimicrobial activities) through bioassay-guided purification ......................................................................................70 3.2. Determination of anti-oxidant activities ..............................................................73 iii 3.3. Anti-bacterial analysis .........................................................................................73 3.4. High resolution (HR) metabolomics analysis......................................................74 3.5. Statistical analysis ...............................................................................................76 4. Results .................................................................................................................................... 76 4.1 Antioxidant study .................................................................................................76 4.2 Antibacterial activity against Methicillin-resistant Staphylococcus aureus (MRSA) ......................................................................................................................89 5. Discussion .............................................................................................................................. 93 5.1. Antioxidant activity of SCG for cosmetic application ........................................93 5.2. Antimicrobial activity of SCG for cosmetic application .....................................96 5.3. Importance of anti-inflammatory and anti-carcinogenesis activity in cosmetics 99 5.4. High resolution metabolomics analysis followed by bioassay guided purification ...............................................................................................................100 6. Conclusion ........................................................................................................................... 101 References ................................................................................................................................... 103 Appendix A. ................................................................................................................................ 123 Appendix B. ................................................................................................................................ 147 1. Introduction .......................................................................................................................... 147 2. Objectives ............................................................................................................................ 150 3. Materials and Methods ......................................................................................................... 150 4. Results and discussion ......................................................................................................... 151 iv LIST OF TABLES Table Page 1.1. Major compounds exist in natural resources that have biological function related to skin care. The list of bioactive compounds have been reported, showing antioxidant, Anti-fungal, skin-whitening, anti-inflammatory, anti-aging, and antimicrobial properties or other skin-care applications…………………………………………………….............8 2.1. Antioxidant activity of SCG methanol extracts of three cultivars including Ethiopian Yirgacheffe, Costa Rican Tarrazu, and Hawaiian Kona ....................................................79 2.2. Identified compounds in purified fraction 14 through XCMS Online HR metabolomics analysis. Each row indicates feature, compound name, m/z, retention time, maximum intensity and its known bioactivity. Using XCMS Online platform, chemical profiling was compiled. .....................................................................................................85 2.3. FeCl2 concentration (µM) of bioactive compounds which were reported
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