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Phenolic Acid Rich Fraction of Gynura Procumbens As Potential Antihyperlipidemic and Antioxidant Agents

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Phenolic Acid Rich Fraction of Gynura Procumbens As Potential Antihyperlipidemic and Antioxidant Agents PHENOLIC ACID RICH FRACTION OF GYNURA PROCUMBENS AS POTENTIAL ANTIHYPERLIPIDEMIC AND ANTIOXIDANT AGENTS KISANTINI A/P MURUGESU UNIVERSITI SAINS MALAYSIA 2018 PHENOLIC ACID RICH FRACTION OF GYNURA PROCUMBENS AS POTENTIAL ANTIHYPERLIPIDEMIC AND ANTIOXIDANT AGENTS by KISANTINI A/P MURUGESU Thesis submitted in fulfillment of the requirements for the degree of Master of Science June 2018 ACKNOWLEDGEMENT Foremost, I am grateful to the Almighty Superior God for the good health and well being that were crucial for the completion of this thesis. I am extremely indebted to my advisor, Prof. Dr. Amirin Sadikun for many insightful conversations, encouragement and sincere advice that have been extended to me from the beginning of study until his retirement day. He was always available for me whenever I had questions about my research and consistently shared his expertise whenever he thought I needed it. I could not have imagined of having a better advisor for my research. Besides my advisor, I would like to thank my main supervisor, Assoc. Prof. Dr. Vikneswaran Murugaiyah and co-supervisor, Prof. Dr. Mohd Zaini Bin Asmawi for their valuable guidance, immense knowledge and useful comments throughout my Masters study period. Their patience and clarity when giving information have helped me a lot during my research and thesis writing. To my advisor and supervisors, thank you for steering me in the right direction. Next, I wish to thank my fellow colleagues, Dr. Sultan, Dr. Mohammad Ali, Ida, Hidayah, Farhana, Syafinaz, Shahrul, Chung Wan Jie, Liew Wai Lam, Saiful and Mathew for their sincere assistance and generosity in sharing knowledge during the study. In particular, I am grateful to Dr. Sultan for his valuable contribution, advice and enlightenment to the success of this research. ii I take this opportunity to thank the department staffs, science officers and technicians for their patience in entertaining our complaints, continuous guidance in handling equipment and for giving access to the research facilities. Without their support and cooperation it would not be possible to conduct this research. Last but not least, a million thanks to my parents, siblings and my partner for unfailing support and enduring love throughout my years of study. Thank you for being there for me during my hard times, I will be thankful forever for your love. Without you all, I wouldn’t have achieved this position in my life. I wish you all the happiness in the world. iii TABLE OF CONTENTS ACKNOWLEDGEMENT ii TABLE OF CONTENTS iv LIST OF TABLES xi LIST OF FIGURES xiv LIST OF APPENDICES xviii LIST OF ABBREVIATIONS xxi LIST OF SYMBOLS xxv ABSTRAK xxvi ABSTRACT xxviii CHAPTER 1 - INTRODUCTION 1.1 Background 1 1.2 Problem statement 4 1.3 Hypothesis 5 1.4 Research objectives 5 CHAPTER 2 - LITERATURE REVIEW 2.1 The genus Gynura 8 2.2 Gynura procumbens (Lour.) Merr. 8 2.2.1 Description of Gynura procumbens (Lour.) Merr. 8 2.2.2 Chemical constituents of Gynura procumbens (Lour.) Merr. 11 2.2.3 Pharmacological activities of Gynura procumbens (Lour.) Merr. 21 2.2.3(a) Wound healing activity 21 2.2.3(b) Anticancer activity 21 iv 2.2.3(c) Antiulcerogenic activity 21 2.2.3(d) Cardiovascular activity 22 2.2.3(e) Ultraviolet (UV) protective activity 22 2.2.3(f) Immunomodulatory activity 22 2.2.3(g) Antihypertensive activity 23 2.2.3(h) Anti-inflammatory activity 23 2.2.3(i) Antiherpetic activity 24 2.2.3(j) Antidiabetic activity 24 2.2.3(k) Antioxidant activity 25 2.2.3(l) Antiplasmodial activity 25 2.2.3(m) Toxicity 25 2.3 Caffeoylquinic acids 26 2.4 Standardization 28 2.4.1 Preliminary screening and chemical group quantification 31 2.4.2 Phytochemical fingerprint profiling 32 2.5 Hyperlipidemia 33 2.5.1 Lipids 33 2.5.2 Classifications of hyperlipidemia 35 2.5.3 Risk factors and clinical symptoms of hyperlipidemia 37 2.5.4 Biosynthesis of lipids 38 2.5.5 Management of hyperlipidemia 41 2.5.6 Laboratory animal models of acute hyperlipidemia 45 2.5.7 High fat diet-induced chronic hyperlipidemic model 46 2.5.8 Natural products in the treatment of hyperlipidemia 47 2.6 Reactive oxygen species and antioxidants 49 v CHAPTER 3 - MATERIALS AND METHODS 3.1 Materials and equipment 55 SECTION I - CHEMISTRY 3.2 Preparation and characterization of extract and fractions of Gynura procumbens 59 3.2.1 Extraction and fractionation of Gynura procumbens leaves 59 3.2.2 Qualitative analysis of ethanolic extract and fractions of Gynura procumbens 61 3.2.2(a) Thin layer chromatography 61 3.2.2(b) Ultraviolet-visible spectroscopy 61 3.2.2(c) Fourier transform infra-red spectroscopy 61 3.2.3 Sub-fractionation of 50 % methanolic fraction 62 3.3 Isolation of chlorogenic acid 63 3.3.1 Spectroscopic & physical characterization of chlorogenic acid 65 3.3.1(a) Nuclear magnetic resonance spectroscopy 65 3.3.1(b) Liquid chromatography–mass spectrometry 65 3.3.1(c) Melting point 66 3.4 Determination of phenolic and flavonoid contents of ethanolic extract and fractions of Gynura procumbens 66 3.4.1 Total phenolic content 66 3.4.2 Total flavonoid content 67 3.5 Evaluation of antioxidant activities of ethanolic extract and fractions of Gynura procumbens and chlorogenic acid 68 3.5.1 Ferric reducing antioxidant power assay 68 3.5.2 DPPH free radical scavenging assay 69 3.5.3 ABTS radical scavenging assay 70 vi 3.6 Development and validation of a HPLC method for quantification of phenolic acids and standardization of Gynura procumbens plant samples 72 3.6.1 Method development 72 3.6.1(a) Chromatographic conditions 72 3.6.2 Sample preparation 72 3.6.2(a) Preparation of standard solutions of phenolic acids 72 3.6.2(b) Preparation of 50 % methanolic fraction of Gynura procumbens ethanolic extract 73 3.6.3 Parameters investigated during method development 73 3.6.4 Peak purity 74 3.6.5 Method validation 74 3.6.5(a) Linearity, limit of detection (LOD) and limit of quantification (LOQ) 74 3.6.5(b) Precision, accuracy and recovery 75 3.6.5(c) Quantification of samples 76 SECTION II - PHARMACOLOGY 3.7 Antihyperlipidemic evaluation of Gynura procumbens 77 3.7.1 Experimental animals 77 3.7.2 Antihyperlipidemic evaluation of standardized ethanolic extract, fractions and chlorogenic acid of Gynura procumbens in poloxamer-407-induced hyperlipidemic rats 77 3.7.2(a) Induction of hyperlipidemia 77 3.7.2(b) Experimental design 78 3.7.2(c) Collection of blood sample 79 3.7.2(d) Analysis of lipid parameters 80 vii 3.7.3 Antihyperlipidemic evaluation of standardized 50 % methanolic fraction of Gynura procumbens in high fat diet-induced hyperlipidemic rats 81 3.7.3(a) Induction of hyperlipidemia 81 3.7.3(b) Experimental design 82 3.7.3(c) Collection of biological samples 82 3.7.4 Statistical analysis 83 3.8 Evaluation of mechanism of antihyperlipidemic activity of standardized 50 % methanolic fraction and chlorogenic acid of Gynura procumbens 84 3.8.1 Evaluation of inhibitory activity of standardized 50 % methanolic fraction and chlorogenic acid of Gynura procumbens on HMG-CoA reductase and pancreatic lipase enzymes 84 3.8.1(a) Preparation of standardized 50 % methanolic fraction and chlorogenic acid 84 3.8.1(b) HMG-CoA reductase inhibitory activity 84 3.8.1(c) Pancreatic lipase inhibitory activity 85 3.8.2 Evaluation of effect of standardized 50 % methanolic fraction of Gynura procumbens on lipids and bile acids excretions 86 3.8.2(a) Liver lipids estimation 86 3.8.2(b) Fecal lipids estimation 87 3.8.2(c) Fecal bile acids estimation 87 3.8.3 Statistical analysis 88 3.9 Toxicological evaluation of standardized 50 % methanolic fraction and chlorogenic acid of Gynura procumbens 88 3.9.1 In vitro cytotoxicity evaluation of standardized 50 % methanolic fraction and chlorogenic acid of Gynura procumbens 88 viii 3.9.1(a) Cell culture 88 3.9.1(b) MTT assay 89 3.9.2 Acute toxicity evaluation of standardized 50 % methanolic fraction of Gynura procumbens 90 3.9.2(a) Animals 90 3.9.2(b) Treatment dose 91 3.9.2(c) Observations 91 CHAPTER 4 - RESULTS & DISCUSSION SECTION I - CHEMISTRY 4.1 Extraction and fractionation of Gynura procumbens leaves 92 4.2 Isolation of chlorogenic acid 96 4.3 Polyphenolics content of ethanolic extract and fractions of Gynura procumbens 110 4.4 Antioxidant activities of ethanolic extract, fractions and chlorogenic acid of Gynura procumbens 111 4.5 Development and validation of a HPLC method for standardization of Gynura procumbens extracts and fractions 118 SECTION II - PHARMACOLOGY 4.6 Antihyperlipidemic effect of standardized ethanolic extract, fractions and chlorogenic acid of Gynura procumbens in poloxamer-407 induced hyperlipidemic rats 141 4.7 Antihyperlipidemic effect of standardized 50 % methanolic fraction of Gynura procumbens in high fat diet-induced hyperlipidemic rats 156 4.8 Mechanism of antihyperlipidemic activity of standardized 50 % methanolic fraction and chlorogenic acid of Gynura procumbens 178 ix 4.8.1 Inhibitory activity of standardized 50 % methanolic fraction and chlorogenic acid of Gynura procumbens on HMG-CoA reductase and pancreatic lipase enzymes 178 4.8.2 Effect of standardized 50 % methanolic fraction of Gynura procumbens on lipids and bile acids secretion 185 4.9 Toxicity of standardized 50 % methanolic fraction and chlorogenic acid of Gynura procumbens 190 4.9.1 Cytotoxicity 190 4.9.2 Acute toxicity 193 4.10 Summary of results 196 CHAPTER 5 - CONCLUSION 5.1 Conclusion 198 5.2 Limitations 201 5.3 Suggestions for future studies 201 REFERENCES 202 APPENDICES x LIST OF TABLES Page Table 2.1 Taxonomic classification of Gynura procumbens (Lour.) Merr 9 Table 2.2 Properties and functions
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