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Effects of Added Flavor on Extraction and Antioxidant Behaviors of Catechins from Green Tea Leaves

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Effects of Added Flavor on Extraction and Antioxidant Behaviors of Catechins from Green Tea Leaves EFFECTS OF ADDED FLAVOR ON EXTRACTION AND ANTIOXIDANT BEHAVIORS OF CATECHINS FROM GREEN TEA LEAVES A Thesis Presented to the Faculty of California State Polytechnic University, Pomona In Partial Fulfillment Of the Requirements for the Degree Master of Science In Chemistry By Yue Zhou 2016 SIGNATURE PAGE THESIS: EFFECTS OF ADDED FLAVOR ON EXTRACTION AND ANTIOXIDANT BEHAVIORS OF CATECHINS FROM GREEN TEA LEAVES AUTHOR: Yue Zhou DATE SUBMITTED: Winter 2016 Chemistry and Biochemistry Department Dr. Yan Liu Thesis Committee Chair Chemistry and Biochemistry Dr. Gregory A. Barding, Jr. Chemistry and Biochemistry Dr. Olive Y. Li College of Agriculture ii ACKNOWLEDGMENTS Foremost, I would like to express my sincere gratitude to my advisor, Dr. Yan Liu, for his continuous support throughout this study. His guidance helped me go through the research project and the thesis writing. I am also thankful to the rest of my thesis committee: Dr. Gregory Barding and Dr. Olive Li, for their time, encouragement and insightful comments. Last, I would like to thank my family: my parents, my husband and my daughters for supporting me spiritually throughout writing this thesis and my life in general. This project was supported by the Chemistry and Biochemistry Department at California State Polytechnic University. Moreover, I greatly appreciate the Goldstein Graduate Research Fellowship Program at the Chemistry and Biochemistry Department for the additional support. iii ABSTRACT Catechins, a group of phenolic compounds present in green tea leaves, can eliminate damaging free radicals inside organisms and are the main contributors to green tea’s antioxidation benefits. Different flavors are often added to the tea brewing process to increase the taste of tea drinks. In this project, green tea extracts with salty and sweet flavor were analyzed by a reversed-phase HPLC method using a C18 column and a mixture of methanol/water (30:70) as the mobile phase with the spectrophotometric detection wavelength at 280 nm. Three major catechins, Epigallocatechin, Epigallocatechin gallate, and Epicatechin, were observed in the green tea extract. The introduction of salt to the brewing process greatly increased the extraction efficiency for all three catechins, while the introduction of sugar affected the extraction differently on individual catechins. The results from the Fenton assay with spectrophotometric detection demonstrated the effect of salt on antioxidation power of catechins from green tea leaves. When employing the Fenton Assay to determine the effect of sugar on antioxidation power of catechins in GTE, both catechins and sugar had the potentials to contribute to the radical scavenging through different routes. More studies are still desired to elucidate the reaction mechanisms. iv TABLE OF CONTENTS Signature Page .............................................................................................................. ii Acknowledgements ....................................................................................................... iii Abstract ......................................................................................................................... iv List of Tables ............................................................................................................... vii List of Figures .............................................................................................................. viii Chapter 1: Introduction .............................................................................................. 1 1.1 Structures of Catechins Present in Tea ..................................................... 1 1.2 Antioxidation Behaviors of Catechins ....................................................... 4 1.3 Applications of Tea Catechins ................................................................... 7 1.4 Extraction of Catechins from Green Tea ................................................... 8 1.5 Separation Analysis ................................................................................... 12 1.6 Determination of Catechin Antioxidation Activity .................................... 15 1.7 Objectives of Project ................................................................................. 20 Chapter 2: Materials and Methodology ..................................................................... 21 2.1 Materials ................................................................................................... 21 2.2 Preparation of the Fenton Reagents ........................................................ 21 2.3 Preparation of Standard Solutions of Catechins ....................................... 22 2.4 Preparation of Green Tea Extract ............................................................. 22 2.5 Optimization of H2O2 Volume ................................................................... 22 2.6 Spectrophotometric Analysis of GTE and Fenton Reagent Mixture ......... 23 2.7 HPLC Analysis ............................................................................................ 25 Chapter 3: Results and Discussion .............................................................................. 26 3.1 HPLC Analysis of GTE ................................................................................. 26 3.2 The Effect of NaCl on Extracting Catechins ............................................... 27 3.3 Antioxidation Behavior ............................................................................. 32 3.4 The effect of NaCl on Antioxidant Activity of Catechins ........................... 34 v 3.5 The Effect of Sucrose on Extraction .......................................................... 38 3.6 The Effect of Sugar on Antioxidant Activity of Catechins ......................... 41 Chapter 4: Summary ................................................................................................... 44 Chapter 5: Future work ............................................................................................... 46 References .................................................................................................................. 47 vi LIST OF TABLES Table 1 Concentration of Standard Solution of Catechins .................................... 22 Table 2 Solution recipes for the mixture of GTE and the Fenton Reagents .......... 23 Table 3 Solution recipes for the mixture of GTE with NaCl and the Fenton reagents ................................................................................................... 24 Table 4 Solution recipes for the mixture of GTE with sugar and the Fenton Reagents ................................................................................................... 24 Table 5 Quantification of the three catechins from GTE ......................................... 26 Table 6 Signals of catechins in GTE with added NaCl ........................................... 29 Table 7 Increase in catechin contents with Introduction of NaCl ......................... 29 Table 8 The antioxidant activity of GTE with NaCl ............................................... 37 Table 9 Signals of catechins in GTE with sugar ...................................................... 39 Table 10 Changes in catechin contents in GTE with sugar ...................................... 40 vii LIST OF FIGURES Figure 1 General molecular structure of catechins .................................................. 2 Figure 2 Molecular structures of common free catechins ....................................... 2 Figure 3 Molecular structures of common esterified catechins ............................... 3 Figure 4 Potential chelating structure between catechin and metal ions ............... 5 Figure 5 Free radical scavenging reaction ................................................................ 6 Figure 6 Schematics of the on-line HPLC-DPPH assay .............................................. 18 Figure 7 The principle of ORAC assay ....................................................................... 19 Figure 8 Representative HPLC chromatogram of GTE .............................................. 27 Figure 9 HPLC chromatogram of GTE (a) without and (b) with NaCl ....................... 28 Figure 10 The effect of NaCl on extraction of total three catechins from tea leaves .................................................................................................................... 30 Figure 11 Structure of pectin and pigment of theaflavin in green tea ....................... 31 Figure 12 Torsion of B, D-rings of EGCG ..................................................................... 32 Figure 13 Effects of H2O2 on the absorbance of the mixture of salicylic acid and Fenton reagents ........................................................................................ 33 Figure 14 HPLC chromatogram of (a) the Fenton reagent with salicylic acid, (b) GTE with the Fenton reagents and salicylic acid, and (c) GTE ........................... 34 Figure 15 Spectra of the mixture of … salicylic acid, GTE with salt, and the Fenton reagents, — salicylic acid, and the Fenton reagents, and --- salicylic acid, GTE, and the Fenton reagent .................................................................... 35 Figure 16 Spectra of the Fenton reagent … with NaCl , — without NaCl ................. 36 viii Figure 17 Effects of added salt on the antioxidant activity of GTE ........................... 38 Figure 18 Representative HPLC chromatogram of (a) pure GTE and (b) GTE with Sugar
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