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The Effects of Gynura Procumbens Extracts on Drug Metabolizing Enzymes

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The Effects of Gynura Procumbens Extracts on Drug Metabolizing Enzymes THE EFFECTS OF GYNURA PROCUMBENS EXTRACTS ON DRUG METABOLIZING ENZYMES ATIQAH BINTI AFANDI UNIVERSITI SAINS MALAYSIA 2015 THE EFFECTS OF GYNURA PROCUMBENS EXTRACTS ON DRUG METABOLIZING ENZYMES by ATIQAH BINTI AFANDI Thesis submitted in fulfillment of the requirements for the degree of Master of Science July 2015 ACKNOWLEDGEMENT First and foremost, all praise be to Allah, the Almighty, the Benevolent for His blessing and guidance for giving me the patience and facilitate the completion of my thesis. I would like to express my gratitude to Prof. Dr. Sharif Mahsufi Mansor, Director of Centre for Drug Research, for giving me the opportunity to continue my master study in this Centre as a full research master’s student and also providing me with facilities vital to the completion of my master study. I would like to extend my appreciation to my supervisor, Assoc. Prof. Dr. Sabariah Ismail for her constructive criticism, guidance, understanding and endless support during the completion of my study. I am thankful to all lab assistants and staffs of Centre for Drug Research for their assistance during the research, especially Nuraziah Hanapi, Nur Sabrina Mohd Yusof and Aznorhaida Ramli for their continuous encouragement. I would like to express my special appreciation to all who have helped in one way or another, especially my dearest lab mates and friends, Nurul Afifah Mohd Salleh, Nor Liyana Mohd Salleh, Zulhilmi Husni and Munirah Haron for their sound judgements and moral support during my study. My special gratitude to the USM Graduate Assistant Scheme, My Brain 15 by the Ministry of Higher Education Malaysia and Short Term Grant Scheme (Modulation of Drug Metabolizing Enzyme Activity by Gynura procumbens Standardized Extracts) for their financial support in these two years. Finally, I owe deepest gratitude to my dear husband Mohd Halimhilmi Zulkiffli, who supports me, giving me strength to finish up my thesis and also to my lovely parents, brothers and sisters for their endless love, prayers and moral support. I am indebted and grateful to those who indirectly contributed to this research. ii Last but not least, I would like to thank my son, Ahmad Luthfi Hakim bin Mohd Halimhimi (3 months old), who being such a good son while I’m doing my thesis correction. Thank you very much. Atiqah binti Afandi USM, July, 2015 TABLE OF CONTENTS Page Acknowledgement ii Table of Contents iii List of Tables viii List of Figures x List of Symbols xviii List of Abbreviations xix List of Appendices xix Abstrak xxiv Abstract xxvi CHAPTER ONE – INTRODUCTION 1 1.1 Background of the study 1 1.2 The Problem Statement of the Study 8 1.3 The purpose of the study 8 1.4 The objectives of the study 9 CHAPTER TWO - LITERATURE REVIEWS 2.1 Description of Gynura procumbens 10 2.2 Taxonomy of Gynura procumbens 11 2.3 Pharmacological potentials of Gynura procumbens 12 2.4 Phytochemical constituents of Gynura procumbens 13 2.5 Phytochemical analysis of Gynura procumbens 14 iii 2.6 Drug metabolism 15 2.7 Phase I drug metabolizing enzymes 17 2.8 CYP3A4 Isoform 19 2.9 CYP1A2 Isoform 23 2.10 P450-GloTM screening system 26 2.11 Phase II drug metabolizing enzymes 27 2.12 UDP-Glucuronosyltransferases (UGTs) 27 2.13 Glutathione S-transferases (GSTs) 30 2.14 In-vitro tools in herb-drug interaction studies 33 CHAPTER THREE - MATERIALS AND METHODS 36 3.1 Chemicals and reagents 36 3.2 Equipment and Instruments 37 3.3 Extraction process of Gynura procumbens 38 3.3.1 Gynura procumbens leaves collection 38 3.3.2 Preparation of Gynura procumbens Methanol Extract 38 3.3.3 Preparation of Gynura procumbens Ethanol Extract 38 3.3.4 Preparation of Gynura procumbens Aqueous Extract 39 3.4 HPLC profiling of Gynura procumbens extracts 39 3.4.1 Preparation of sample and standard solution 39 3.4.2 Chromatographic conditions 40 3.4.3 Quantification of kaempferol-3-O-rutinoside and 40 astragalin in Gynura procumbens extracts 3.5 Antioxidant studies on Gynura procumbens extracts 40 iv 3.5.1 Determination of total phenolic content of Gynura 40 procumbens extracts 3.5.2 Determination of total flavonoid content of Gynura 41 procumbens extracts 3.5.3 Evaluation of antioxidant activity of Gynura procumbens 42 extracts 3.6 Phase I CYP450 enzymes inhibition assay 43 3.6.1 Preparation of plant extracts samples and positive controls 43 3.6.2 Generating a D-luciferin standard curve 44 3.6.3 Evaluation on the effect of Gynura procumbens extracts 45 and known inhibitors on CYP450 enzyme activity 3.7 Determination of protein content in RLM and RLCF 48 3.8 Preparation of plant extracts samples and positive controls 49 3.9 Phase II UGT enzymes inhibition assay 49 3.9.1 Preparation of p-nitrophenol (pNP) standard curve 49 3.9.2 Optimization of UGT enzyme assay parameters 50 3.9.2 (a) Linearity of incubation time 50 3.9.2 (b) Linearity of protein concentration 51 3.9.3 (c) Optimization of triton X-100 52 3.9.3 Determination of maximal velocity of reaction (Vmax) and 52 Michaelis constant (Km) of pNP glucuronidation 3.9.4 Evaluation on the effect of Gynura procumbens extracts 53 and known inhibitors on UGT enzyme activity 3.10 Phase II GST enzymes inhibition assay 55 3.10.1 Linearity of incubation time and protein concentration 55 v 3.10.2 Evaluation on the effect of Gynura procumbens extracts 56 and known inhibitor on GST enzyme activity 3.11 Statistical Analysis 57 CHAPTER FOUR - RESULT 58 4.1 Extraction process of dried leaves of Gynura procumbens 58 4.2 Quantification of Kaemperol-3-O-rutinoside and astragalin in 58 Gynura procumbens extracts 4.3 Antioxidant properties of Gynura procumbens extracts 64 4.3.1 Total phenolic content of Gynura procumbens extracts 64 4.3.2 Total flavonoid content of Gynura procumbens extracts 65 4.3.2 DPPH Free Radical Scavenging Capacity of Gynura 67 procumbens extracts 4.4 Phase I CYP450 enzymes inhibition assay 68 4.4.1 D-Luciferin Standard Curve 68 4.4.2 The effect of known CYP450 inhibitors on CYP450 70 isoforms activity 4.4.3 The effect of Gynura procumbens ethanol extract on 71 CYP450 isoforms 4.4.4 The effect of Gynura procumbens methanol extract 73 on CYP450 Isoforms 4.4.5 The effect of Gynura procumbens aqueous extract 75 on CYP450 isoforms 4.5 Determination of protein content in RLM and RLCF 77 4.6 Phase II UGT enzyme inhibition assay 79 4.6.1 p-nitrophenol (pNP) standard curve 79 vi 4.6.2 Optimization of UGT enzyme assay parameters 80 4.6.2 (a) Incubation time 80 4.6.2 (b) Protein concentration 81 4.6.2 (c) Optimization of triton X-100 82 4.6.3 Determination of maximal reaction velocity (Vmax) and 83 Michaelis constant (Km) of UGT enzyme inhibition assay 4.6.4 The effect of known UGT inhibitor and Gynura 84 procumbens extracts on UGT enzyme activity 4.7 Phase II GST enzyme inhibition assay 87 4.7.1 Optimization of incubation time and protein concentration 87 4.7.2 The effect of known GST inhibitor and Gynura 89 procumbens extracts on GST enzyme activity 3.7.2 Inhibitory Effect of Known Inhibitor (Tannic Acid) on 75 GST Enzyme Assay 3.7.3 Inhibitory Effect of Gynura procumbens Extracts on 76 GST Enzyme Assay CHAPTER FIVE - DISCUSSION 92 5.1 Extraction process of Gynura procumbens and quantification of 92 its marker compounds 5.2 Total phenolic content, total flavonoid content and antioxidant 94 activity of Gynura procumbens extracts 5.3 The effect of Gynura procumbens extracts on human CYP3A4 96 and CYP1A2 enzyme activity using recombinant enzymes 5.4 The effect of Gynura procumbens extracts on rat UGT enzyme 102 activity using RLM vii 5.5 The effect of Gynura procumbens extracts on rat GST enzyme 105 activity using RLCF CHAPTER SIX - CONCLUSION 109 REFERENCES 111 APPENDICES 126 LIST OF PUBLICATIONS 131 viii LIST OF TABLES Page Table 1.1 Interactions between herbal medicines and drug 3 metabolizing enzymes. Table 2.1 List of factors that affect the activity of drug metabolizing 16 enzymes Table 2.2 List of CYP3A4 substrates 22 Table 2.3 List of CYP1A2 substrates 25 Table 4.1 Type of extract and percentages of yield obtained for each 58 extraction method. Table 4.2 Retention time of standard marker compound in Gynura 59 procumbens extracts. Table 4.3 The amount of kaempferol-3-O-rutinoside and astragalin in 63 Gynura procumbens extracts. Table 4.4 Total phenolic content of Gynura procumbens extracts. 65 Table 4.5 Total flavonoid content of Gynura procumbens extracts. 66 Table 4.6 IC50 values for DPPH scavenging activity of Gynura 68 procumbens extracts. Values are expressed as mean in microgram per milliliter of Gynura procumbens extracts ± SEM for four replicates (n=4). Table 4.7 IC50 values of positive controls of CY1A2 and CYP3A4 70 enzymes. ix Table 4.8 The half maximal inhibitory concentration (IC50) of Gynura 77 procumbens extracts on the metabolism mediated by CYP3A4 and CYP1A2. Table 4.9 Concentration of protein in rat liver microsome (RLM) and 78 rat liver cytosolic fraction (RLCF) for male Sprague Dawley rats. Table 4.10 Enzyme kinetic parameters for UGT enzyme-mediated pNP 84 glucuronidation in RLM. Table 4.11 Relative activity of UGT enzyme after incubated with 86 Gynura procumbens extracts and diclofenac at three different concentrations of 10, 100 and 1000µg/mL. Table 4.12 IC50 values for Gynura procumbens extracts and tannic acid 91 showing inhibition towards 1-chloro-dinitrobenzene (CDNB) conjugation reaction catalyzed by GST enzyme.
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