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Phytochemical Isolation and Standardization of Orthosiphon Stamineus Benth

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Phytochemical Isolation and Standardization of Orthosiphon Stamineus Benth PHYTOCHEMICAL ISOLATION AND STANDARDIZATION OF ORTHOSIPHON STAMINEUS BENTH. LEAF EXTRACT FROM DIFFERENT LOCATIONS AND SELECTED ANTIOXIDANT AND TOXICITY STUDIES NUR FARAH AMALINA BINTI MUGHNI UNIVERSITI SAINS MALAYSIA 2014 PHYTOCHEMICAL ISOLATION AND STANDARDIZATION OF ORTHOSIPHON STAMINEUS BENTH. LEAF EXTRACT FROM DIFFERENT LOCATIONS AND SELECTED ANTIOXIDANT AND TOXICITY STUDIES by NUR FARAH AMALINA BINTI MUGHNI Thesis submitted in fulfillment of the requirements for the degree of Master of Science February 2014 PENGASINGAN FITOKIMIA DAN PEMIAWAIAN EKSTRAK DAUN ORTHOSIPHON STAMINEUS BENTH. DARI LOKASI YANG BERBEZA UNTUK KAJIAN ANTIOKSIDAN DAN TOKSISIITI oleh NUR FARAH AMALINA BINTI MUGHNI Tesis yang diserahkan untuk memenuhi keperluan bagi Ijazah Sarjana Sains Februari 2014 ACKNOWLEDGEMENTS First and foremost praise to Allah the almighty who gave me the knowledge, strength and the determination to finish my thesis successfully. This success and final outcome of this project required a lot of guidance and assistance from many people. I am extremely fortunate to have gotten this along the completion of my project work. I would like to express the deepest appreciation to my supervisors Prof. Dr. Zhari Ismail for his commitment and invaluable guidance throughout the study. I offer my sincerest gratitude to my co-supervisor Associate Prof. Dr Nornisah Mohamed, without her invaluable assistance and support, this study would not have been completed. I express my special thanks to Majlis Amanah Rakyat (MARA) for providing financial support and scholarship. I am also grateful to School of Pharmaceutical Science , USM for providing a good research environment and all of the staff at this school for their kindness help and contribution in this study. My sincere thanks to Dr Abdul Rahim and Dr Beh for helping me and give many ideas for completing my research and Dr Lee Chong Yew for helping me elucidate NMR structure. My sincere appreciation goes to all of my friends and lab mates especially Fatin Fathiah for their constant encouragement and investing their time and energies in this project. ii TABLE OF CONTENTS ACKNOWLEDGEMENT ii TABLE OF CONTENTS iii LIST OF TABLES x LIST OF FIGURES xii LIST OF ABBREVIATION xv ABSTRAK xvii ABSTRACT xx CHAPTER 1 – INTRODUCTION 1.1 General Introduction 1 1.2 Justification of the Study 4 1.3 Objectives of the Study 6 CHAPTER 2 – LITERATURE REVIEW 2.1 Orthosiphon stamineus 7 2.1.1 Classification and Description 7 2.1.2 Botanical Description 8 2.1.3 Plant Habitat and Cultivation 10 2.1.4 Chemical Constituents 10 2.1.5 Traditional uses of Orthosiphon stamineus 17 2.1.6 Review of Biological Activity of 17 Orthosiphon stamineus iii 2.2 Antioxidant 27 2.2.1 Types of Antioxidant 28 2.2.2 Natural Antioxidants 28 2.2.3 Antioxidant Assays for Plant 29 2.2.4 Literature Study of Antioxidant Activity 29 2.2.5 Analysis and Quantification of Phenolic Compounds 30 2.3 Cytotoxicity 30 2.4 Malaysian Herbal Monograph 32 2.5 The Challenges of Standardizing Herbs 2.5.1 The Plant Physiology 32 2.5.2 Variability on Individual Plant 33 2.5.3 Adulteration and Deterioration 35 CHAPTER 3 – EXPERIMENTAL METHODOLOGY 3.1 Materials and Chemicals 37 3.2 Apparatus and Instrumentation 37 3.2.1 High Performance Liquid Chromatography 37 3.2.2 Ultra Violet (UV) Spectroscopy 38 3.2.3 Fourier Transform Infrared (FTIR) Spectroscopy 38 3.2.4 High Performance Thin Layer Chromatography (HPTLC) 38 3.2.5 Extraction 38 3.2.5 Nuclear Magnetic Resonance (NMR) 38 3.3 Procurement of Raw Material 3.3.1 The Source of Orthosiphon stamineus leaf 39 iv 3.4 Phytochemical Screening 3.4.1 Alkaloids 41 3.4.2 Terpenes 41 3.4.3 Flavonoids 42 3.4.4 Anthraquinones 42 3.4.5 Tannins 42 3.4.6 Saponins 43 3.5 Quality Control Analysis 3.5.1 Ash Content 43 3.5.1.1 Total Ash 43 3.5.1.2 Acid Insoluble Ash 44 3.5.2 Extractive Values (Hot extraction) 3.5.2.1 Water 44 3.5.2.2 Ethanol 44 3.5.3 Extractive Value (Cold Maceration) 3.5.3.1 Water 45 3.5.3.2 Ethanol 45 3.5.4 Loss of Drying 45 3.5.5 Nutritive Value 46 3.5.5.1 Protein 46 3.5.5.2 Fat 49 3.5.6 Determination of Heavy Metals 49 3.5.6.1 Preparation of samples 49 v 3.5.7 Microbial Limit Test (MLT) of Orthosiphon stamineus 49 Leaf 3.5.7.1 Procedure for Total Aerobic Microbial, 50 Yeast and Mold Count (via pour plate) 3.5.7.2 Procedures for Specific Microorganism Test 50 3.6 Plant Extraction 51 3.7 Chemical Profiling 3.7.1 High Performance Thin Layer Chromatography (HPTLC) 52 3.7.2 High Performance Liquid Chromatography 53 3.7.2.1 Preparation of Standards and Test Samples 53 3.7.2.2 Chromatographic Condition 53 3.7.3 Ultra violet-Visible (UV-Vis) Spectrophotometry 53 3.7.4 Attenuated Total Reflection-Fourier Transform Infrared (ATR-FTIR) Spectrophotometry 54 3.8 Chemometric Classification of Orthosiphon stamineus by Fourier Transform Infrared (FT-IR) 54 3.8.1 Sample Analysis 54 3.8.2 Data Analysis 55 3.9 Isolation of Chemical Components 56 3.9.1 Extraction 56 3.9.2 Separation of Chemical Components from 57 Chloroform Extract 3.9.3 Qualitative Analysis of F1 using Spectroscopic 58 and Chromatographic Techniques vi 3.9.4 Development of High Performance Liquid Chromatography (HPLC) Methanol of F1 Compound in Water Extract of Orthosiphon stamineus Leaf 59 3.9.5 Validation of HPLC Method 60 3.9.6 Quantification of F1 Compound in Methanol Extract of Orthosiphon stamineus Leaf by HPLC Method 61 3.10 Antioxidant activity 62 3.10.1 Chemicals and Apparatus 62 3.10.2 Plant Samples 62 3.10.3 Assay for Total Phenolic 62 3.10.4 Assay for Total Flavonoids 63 3.10.5 Scavenging Effect on 1,1-diphenyl-2-picrylhydrazyl 64 (DPPH) 3.10.6 Antioxidant Assay Using a β-carotene-linoleate 64 Model System 3.11 Toxicity Assay 65 3.12 Statistical Analysis 66 CHAPTER 4 – RESULTS AND DISCUSSION 4.1 Phytochemical Screening 67 4.2 Quality Control Analysis 68 4.2.1 Ash Content 68 4.2.2 Loss of Drying 70 vii 4.2.3 Extractive Values 71 4.2.4 Nutritive Value 75 4.2.5 Determination of Heavy Metals 76 4.2.6 Microbial Limit Test (MLT) of Orthosiphon stamineus 77 Leaf 4.3 Chemical Profiling 80 4.3.1 High Performance Thin Layer Chromatography (HPTLC) 80 4.3.2 High Performance Liquid Chromatography 81 4.3.3 Ultra violet-Visible (UV-VIS) Spectrophotometry 86 4.3.4 Attenuated Total Reflectance-Fourier Transform Infrared (ATR-FTIR) spectroscopy 87 4.4 Chemometric Classification of Orthosiphon stamineus by Fourier Transform Infrared FT-IR 92 4.5 Environmental Effects 101 4.6 Isolation using Aqueous Extract of Orthosiphon stamineus Leaf 115 4.7 Antioxidant Activity 131 4.7.1 Total Phenolic 131 4.7.2 Total Flavonoids 132 4.7.3 Scavenging Effect on 1,1-diphenyl-2-picrylhydrazyl 136 (DPPH) 4.7.4 Antioxidant Assay Using a β-carotene-linoleate 140 Model System 4.7.5 Statistical Analysis 145 4.8 Toxicity using Brine Shrimp Lethality Assay 146 viii CHAPTER 5 – CONCLUSION 5.1 Conclusion 150 5.2 Suggestion for Further Studies 152 REFERENCES 153 APPENDICES 168 LIST OF PUBLICATION 197 ix LIST OF TABLES Pages Table 1.1 Products Orthosiphon stamineus registered under National Pharmaceutical Control Bureau (NPCB) 4 Table 1.2 Patents published based on the World International Property Organization (WIPO) 5 Table 2.1 Chemical constituents of Orthosiphon stamineus 12 Table 2.2 Summary of scientific studies on the Orthosiphon stamineus from the reviewed literature 22 Table 3.1 Orthosiphon stamineus from various localities used in this study 39 Table 3.2 Microwave digestion setting 49 Table 4.1 Preliminary phytochemical test of leaves of dried powder Orthosiphon stamineus 68 Table 4.2 Summary of physicochemical analysis of leaf of Orthosiphon stamineus 74 Table 4.3 Nutritive value (energy, carbohydrate, protein and fat) of dried powder leaf of Orthosiphon stamineus Benth. 75 Table 4.4 Heavy metal content of Orthosiphon stamineus leaf 77 Table 4.5 Contamination of microbial in the leaf of Orthosiphon stamineus 79 Table 4.6 Percentage of marker content in of Orthosiphon stamineus leaf 85 Table 4.7 Major characteristic IR absorbtion bands of Orthosiphon stamineus 91 Table 4.8 Type of soil for 10 different locations of Orthosiphon stamineus plant 102 x Table 4.9 Temperature of location for the samples of Orthosiphon stamineus collected 104 Table 4.10 Percentage of humidity of the samples from ten different locations 105 Table 4.11 Altitude of the samples collected from ten different locations 107 13 Table 4.12 Comparison C NMR (CDCl3) spectral data of F1 compound 119 Table 4.13 Precision of the HPLC methods for the determination of F1 compound in Orthosiphon stamineus leaf water extract 126 Table 4.14 Percentage F1 compound in the water extract of Orthosiphon stamineus in different locations 127 Table 4.15 IC50 values of different extracts of Orthosiphon stamineus in DPPH scavenging assay 138 Table 4.16 Correlation berween total phenolic, total flavonoid, DPPH scavenging assay and β-carotene linoleic acid 145 Table 4.17 Toxicity activity using brine shrimp assay 148 xi LIST OF FIGURES Pages Figure 2.1 Picture of Orthosiphon stamineus leaf 8 Figure 2.2 Flower of Orthosiphon stamineus 9 Figure 2.3 Chemical structure of Orthosiphon stamineus (diterpenes) 13 Figure 2.4 Chemical structure of Orthosiphon stamineus (triterpenes) 14 Figure 2.5 Chemical structure of Orthosiphon stamineus (flavones) 15 Figure 2.6 Chemical structure of Orthosiphon stamineus (phenolic acid) 16 Figure 2.7 Chemical structure of Orthosiphon stamineus (benzochromene) 16 Figure 3.1 Orthosiphon stamineus from various localities use in this study 40 Figure 3.2 Scheme of extraction of Orthosiphon stamineus dried leaves 56 Figure
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