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Phytochemical and Biological Investigation of Jatropha Pelargoniifolia Roots Native to the Kingdom of Saudi Arabia

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Phytochemical and Biological Investigation of Jatropha Pelargoniifolia Roots Native to the Kingdom of Saudi Arabia Phytochemical and Biological Investigation of Jatropha pelargoniifolia Roots Native to the Kingdom of Saudi Arabia Zur Erlangung des akademischen Grades eines Dr. rer. nat. von der Fakultät Bio- und Chemieingenieurwesen der Technischen Universität Dortmund genehmigte Dissertation vorgelegt von Hanan Yahya Aati aus Riyadh, Königreich Saudi Arabien Tag der mündlichen Prüfung: 05.12.2018 1. Gutachter/-in: Prof. Dr. Oliver Kayser 2. Gutachter/-in: Prof. Dr. Albert Sickmann Dortmund, 2018 I I The research described in this thesis was conducted at the Department of Pharmacognosy (Pharmacy College, King Saud University, Kingdom Saudi Arabia) according to the requirements of the External joint supervision program for PhD degree (King Saud University) and at the Department of Biochemical and Chemical Engineering, Chair of Technical Biochemistry, TU Dortmund University. I Dedication I wish to dedicate this thesis to My wonderful parents (Yahya & Fatimah) For their endless love, continued support and encouragement. My husband (Hamad) who has been a constant source of support and encouragement during the challenges of life. My lovely children They are five flowers in my life (Shahad, Abdulmalik, Fares, Taleen & Zeyad) I do not forget to send a bunch of thanks and gratitude For my love friend (Jwaher Al-Qahtani) For my sisters (Amal & Amoon) For my brothers (Sultan, Salman & Abdulrahman) II Acknowledgements In the name of Allah, most gracious, most merciful. All praise and glory to Allah the almighty who alone made this objective to be accomplished. My deep appreciation goes to my thesis supervisors, Dr. Oliver Kayser, Professor of the Chair Technical Biochemistry, TU Dortmund University, Germany and Dr. Ali A. El-Gamal, Professor of Pharmacognosy, College of Pharmacy, King Saud University whose gave me a lot of their expertise and research insight. They gave me a lot of their time and helped me go through the hard way with constant encouragement and influential discussions. I am deeply grateful to their valuable guidance and advices. It would have never been possible for me to complete this work without their incredible support and encouragement. I would like to express my deep gratitude and respect to Dr. Omar Basudan, Assistant Professor of Pharmacognosy, King Saud University who advice and gave me great help in practical work. My thanks also extend to my colleagues in Pharmacognosy Department, King Saud University and in Technical Biochemistry Department, TU Dortmund for continuous support and valuable advice. Last but not the least, I wish to express my heartfelt gratitude to my parents for their continuous support. They taught me how to be patient, strong and sincere in my work. No words can express my appreciation to my dear husband Hamad Aati and my children (Shahad, Abdulmalik, Fares, Taleen & Zeyad) for their love that give me strength to move forward and make our dream come true. Furthermore, I wish to express my thanks to my brothers (Sultan, Salman and Abdulrahman), sisters (Amal and Amoon), for their support and constant love. Finally, this dissertation is really dedicated to my family. III Table of contents Abstract 1-2 Chapter 1 Introduction 3 1.1. Background 4 1.2. Scope and objective of thesis 5-6 1.3. Family Euphorbiaceae 7 1.4. Genus Jatropha 7 1.5. Jatropha pelargoniifolia Courb. 7-9 1.6. Taxonomic classification of J. pelargoniifolia 7-9 1.7. Some reported biological activities of various Jatropha 10-12 species 1.8. Phytochemical investigation of different Jatropha species 12-18 1.9. References 19-21 Chapter 2 Comparative study of the biological activities of Jatropha 22 pelargoniifolia and Jatropha glauca native to Saudi Arabia 2.1. Abstract 23 2.2. Introduction 24 2.3. Materials and methods 25-30 2.4. Statistical analysis 31 2.5. Results 31-38 2.6. Discussion 39-43 2.7. Conclusion 43 2.8. References 44-47 Chapter 3 Chemical composition and biological activity of the essential 48 oil from the roots of Jatropha pelargoniifolia Courb. native to Saudi Arabia 3.1. Abstract 49 3.2. Introduction 50 3.3. Materials and methods 51-56 IV 3.4. Results and discussion 57-65 3.5. Conclusion 66 3.6. References 67-69 Chapter 4 Comparative study of the chemical composition of essential 70 oils of Jatropha pelargoniifolia and Jatropha glauca native to Saudi Arabia 4.1. Abstract 71 4.2. Introduction 72 4.3. Materials and methods 73-74 4.4. Results and discussion 74-80 4.5. Conclusion 81 4.6. References 82-83 Chapter 5 The phytochemical and biological investigation of Jatropha 84 pelargoniifolia roots native to the Kingdom of Saudi Arabia 5.1. Abstract 85 5.2. Introduction 86 5.3. Results and discussion 87-95 5.4. Materials and methods 95-100 5.5. Conclusion 101 5.6. References 102-105 Chapter 6 Traditional use of ethnomedicinal native plants in Kingdom of 106 Saudi Arabia 6.1. Abstract 107 6.2. Introduction 108-111 6.3. Materials and methods 111 6.4. Results and discussion 112-118 6.5. Conclusions 118-119 6.6. References 120-125 V Chapter 7 Disscusion, summary and outlook 126-132 Chapter 8 8.1. Appendix A: Glossary of abbreviations 132-134 8.2. Appendix B: Supplementary material for chapter 3 135-140 8.3. Appendix C: Supplementary material for chapter 4 141-144 8.4. Appendix D: Supplementary material for chapter 5 145-155 8.5. Appendix E: Supplementary material for chapter 6 156-191 8.6. Appendix F: List of original contributions 192-194 8.7. Appendix G: Curriculum vitae 195-198 VI Abstract Reviewing the current literature for the phytochemical importance of the plants belonging to genus Jatropha revealed broad range of secondary metabolites isolated such as, diterpenoids, triterpenoids, non-conventional coumarino-lignoids, alkaloids, coumarins, flavonoids, cyclic peptides and steroids. This is indeed a reflection on the versatility of the enzymatic system present in the plants belonging to the family Euphorbiaceae but nothing was reported regarding pelargoniifolia species. Thus, it was of interest to explore the active constituents and biological importance for the titled plant which is used traditionally to cure ulcers and wounds in Ethiopia and Saudi Arabia. In vivo and in vitro studies were carried out to evaluate the potential hepatoprotective, antinociceptive, anti-inflammatory and antidiabetic/hypoglycemic effects of the total alcoholic extracts of aerial parts and roots of J. pelargoniifolia and J. glauca species in comparison to those of standard clinical drugs. As the result, the roots of J. glauca showed higher hepatoprotective and antinociceptive (63.85%) activities in comparison to indomethacin (69.87%). In addition, the root extracts from J. pelargoniifolia exhibited greater anti-inflammatory (50.63%) and hypoglycemic (37.98%) activities when compared with phenylbutazone (64.63%) and glibenclamide (51.57%), respectively. Finally, extracts from the aerial parts of J. glauca showed significantly higher anti-diabetic activity in mice with alloxan-induced diabetes (39.93%) when compared with glibenclamide (47.13%). Moreover, the chemical composition of the essential oil separated from J. pelargoniifolia roots was determined via GC-FID, resulting in isolation of 80 compounds representing 99.99% of the total oil constituents. Among these, 77.31% were sesquiterpenes, 14.62% were fatty acids, 7.21% were other components (i.e., phenolics, hydrocarbons, etc.), and 0.85% were monoterpenes. Then, the essential oil was evaluated for its potency as an anti-inflammatory, antioxidant, antipyretic, and antinociceptive agent by in vivo and in vitro models. The obtained results demonstrated that the investigated essential oil of J. pelargoniifolia roots could be used as a natural remedy for their anti-inflammatory, antinociceptive, antipyretic, and antioxidant effects. 1 Additionally, the chemical composition of the essential oil isolated from roots of J. pelargoniifolia was compared with the essential oils isolated from aerial parts of the same plant as well with different Jatropha species, J. glauca aerial parts and roots. Oxygenated sesquiterpenes and fatty acids were predominant chemical classes in oil isolated from roots of both species. On the other hand, oils from aerial parts were high in oxygenated diterpenes (35.30% in J. glauca and 32.23% in J. pelargoniifolia). Oils from J. pelargoniifolia aerial parts were high in oxygenated sesquiterpenes followed by fatty acids, while those from J. glauca were rich in fatty acids and other phenolics (hydrocarbons/cyclic). J. glauca and J. pelargoniifolia have similar morphology, except for leaf surface (hairy in J. pelargoniifolia and smooth in J. glauca) and fruit color (darker in J. pelargoniifolia), and these species are therefore often confused by native people in southern Saudi Arabia. This study clarified chemotaxonomic characters of J. glauca and J. pelargoniifolia via chemical composition analysis of essential oils of roots and aerial parts. Finally, extensive phytochemical study for different fractions of J. pelargoniifolia, resulted in the isolation and identification of a total twenty-two compounds belonging to different chemical classes of secondary metabolites by using different chromatographic techniques. Two new compounds belong to coumarin glucoside and alkaloid; 6-hydroxy-8-methoxycoumarin-7-O-β-D-glycopyranoside and 2-hydroxymethyl-N-methyltryptamine, respectively were isolated and identified for the first time from a natural source. The anti-inflammatory, antinociceptive, antipyretic and antioxidant activities were evaluated for some isolated compounds which are available in good yields. Compound 2-hydroxymethyl-N-methyltryptamine can be used as starting material for semi synthesis of related analogous aiming to produce new drug leads used for treatment of contemporary disease such as; depression, anxiety, pain, obesity and many more. The roots of J. pelargoniifolia showed also significant antinociceptive, anti-inflammatory, antipyretic and free radical scavenging activities may be due to its content of many bioactive constituents belong to various chemical classes and those results were support the efficient use of this plant in Saudi Traditional Medicine as remedy for pain relieve and curing many inflammatory conditions.
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