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Isolation of Bioactive Constituents from Kigelia Africana and Phlomis Stewartii; the Medicinal Plants of Pakistan

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Isolation of Bioactive Constituents from Kigelia Africana and Phlomis Stewartii; the Medicinal Plants of Pakistan BISMILLAH Isolation of Bioactive Constituents from Kigelia africana and Phlomis stewartii; The Medicinal Plants of Pakistan A Dissertation Submitted for The Fulfillment of The Requirement for The Award of Degree of Doctor of Philosophy in Chemistry By Bushra Jabeen Department of Chemistry The Islamia University of Bahawalpur, Bahawalpur-63100, Pakistan 2014 DECLARATION DECLARATION I Bushra Jabeen, hereby declare that the research work, “Isolation of Bioactive Constituents from Kigelia africana and Phlomis stewartii; The Medicinal Plants of Pakistan” was carried out in the Department of Chemistry, The Islamia University of Bahawalpur, Pakistan. All the work has been published by us in peer reviewed journals. I undertake that I did not submit the same work to any other institution or university for the degree of Doctor of Philosophy (Ph. D) and shall not, in future, be submitted for obtaining similar degree to any other university. BUSHRA JABEEN CERTIFICATE CERTIFICATE It is certified that Bushra Jabeen D/O Muhammad Mushtaq has carried out the research work, embodied in this thesis, under my supervision in the Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur, Pakistan. The thesis entitled, “Isolation of Bioactive Constituents from Kigelia africana and Phlomis stewartii; The Medicinal Plants of Pakistan” submitted by her has been evaluated by us and is found appropriate to fulfill the requirement for the degree of Doctor of Philosophy (Ph. D) in Chemistry. Dr. Naheed Riaz Chairman (Research Supervisor) Department of Chemistry Associate Professor The Islamia University of Bahawalpur Department of Chemistry Pakistan The Islamia University of Bahawalpur Pakistan DEDICATION Dedicated to My Respected and Beloved Father and Mother Who Supported Me with Their Love Prayers and Guidance Also To My Ever Loving Sister and Brothers CONTENTS CONTENTS Acknowledgment i Summary iii Chapter # 1: Introduction (Part A) 1 1.1 Family Bignoniaceae 3 1.2 The Genus Kigelia 3 1.3 Kigelia africana 3 1.3.1 Pharmaceutical Importance of Kigelia africana 3 1.3.2 Literature Survey on Kigelia africana 4 1.4.1 Introduction of limonoids 13 1.4.2 Characteristics 13 1.4.3 Classification 13 1.4.3.1 Ring Intact Limonoids 15 1.4.3.1.1 Azadirone-Class 15 1.4.3.1.2 Cedrelone-Class 16 1.4.3.1.3 Havanensin-Class 16 1.4.3.1.4 Trichilin-Class 16 1.4.3.1.5 Vilasinin-Class 16 1.4.3.1.6 Others 16 1.4.3.2 Ring-seco Limonoids 17 1.4.3.2.1 Demolition of a Single Ring 18 1.4.3.2.2 Demolition of Two Rings 18 1.4.3.2.3 Demolition of Three Rings (Rings A,B,D-seco Group) 18 1.4.3.3 Rearranged Limonoids 18 1.4.3.3.1 1,n-Linkage Group 18 1.4.3.3.2 2,30-linkage Group 19 1.4.3.3.3 8,11-Linkage Limonoids (Trijugin-Class) 20 1.4.3.3.4 10,11-Linkage Limonoids (Cipadesin-Class) 20 1.4.3.3.5 Other Linkages Group 20 1.4.3.4 Limonoids Derivatives 20 CONTENTS 1.4.3.4.1 Pentanortriterpenoids, Hexanortriterpenoids, Eptanortriterpenoids, Octanortriterpenoids, and Enneanortriterpenoids Derivatives 20 1.4.3.4.2 Simple Degraded Derivatives 21 1.4.3.4.3 N-Containing Derivatives 21 1.4.4 Occurrence 23 1.4.5 Biological Activities 26 1.4.6 Biosynthesis of Limonoids 29 Chapter # 2: Results and Discussion 33 2.1 Structure Elucidation of New Compounds 35 2.1.1 1-O-Deacetyl-2α-methoxykhayanolide E (158) 35 2.1.2 Structure Elucidation of Kigelianolide (159) 40 2.2 Structure Elucidation of Known Compounds 42 2.2.1 Structure Elucidation of Deacetylkhayanolide E (160) 42 2.2.2 Structure Elucidation of 1-O-Deacetyl-2α-hyroxykhayanolide E (161) 44 2.2.3 Structure Elucidation of Khayanolide B (162) 46 2.2.4 Structure Elucidation of β-Sitosterol (5) 47 2.2.5 Structure Elucidation of β-Sitosterol 3-O-β-D-glucopyranoside (163) 49 2.2.6 Structure Elucidation of Oleanolic acid (164) 50 2.2.7 Structure Elucidation of Quercitrin (165) 52 2.2.8 Structure Elucidation of 1-O-methyl-D-chiro-inositol (166) 54 2.3 AChE, BChE and LOX inhibitory activities of compounds 158-162 55 Chapter # 3: Experimental 56 3.1 General Experimental Procedures 57 3.2 Plant Material 59 3.3 Extraction and Isolation 59 3.4.1 Characterization of 1-O-Deacetyl-2-α-methoxykhayanolide E (158) 61 3.4.2 Characterization of Kigelianolide (159) 62 3.4.3 Characterization of Deacetylkhayanolide E (160) 63 3.4.4 Characterization of 1-O-Deacetyl-2α-hyroxykhayanolide E (161) 64 3.4.5 Characterization of Khayanolide B (162) 65 3.4.6 Characterization of β-Sitosterol (5) 66 CONTENTS 3.4.7 Characterization of β-Sitosterol 3-O-β-D-glycopyranoside (163) 67 3.4.8 Characterization of Oleanolic Acid (164) 69 3.4.9 Characterization of Quercitrin (165) 70 3.4.10 Characterization of 1-O-Methyl-D-chiro-inositol (166) 71 Chapter # 4: Introduction (Part B) 72 4.1 The Family Labiatae 74 4.2 The Genus Phlomis 74 4.3 Phlomis stewartii 74 4.4 Ethnobotanical Importance of the Genus Phlomis 74 4.5 Pharmacological Importance of Genus Phlomis 75 4.6 Literature Survey on Genus Phlomis 75 4.7 Biosynthesis of 28-Nortriterpenoids 80 Chapter # 5: Results and Discussion 85 5.1 New Compounds Isolated from Phlomis stewartii 87 5.1.1 Structure Elucidation of Stewartiiside (186) 87 5.1.2 Structure Elucidation of Stewertiisin A (187) 91 5.1.3 Structure Elucidation of Stewertiisin B (188) 94 5.1.4 Structure Elucidation of Stewertiisin C (189) 97 5.2 Structure Elucidation of Known Compounds 99 5.2.1 Structure Elucidation of Notohamosin A (190) 99 5.2.2 Structure Elucidation of Phlomispentanol (191) 101 5.2.3 Structure Elucidation of Oleanolic acid (164) 102 5.2.4 Structure Elucidation of 2-Hydroxybenzoic acid (192) 104 5.2.5 Structure Elucidation of 4-Hydroxybenzoic acid (193) 105 5.2.6 Structure Elucidation of Caffeic acid (194) 106 5.2.7 Structure Elucidation of Tiliroside (195) 107 5.2.8 Structure Elucidation of Isorhamnetin 3-(6-p-coumaroyl)-β-D- glucopyranoside (196) 109 5.2.9 Structure Elucidation of Lunariifolioside (197) 111 5.3 α-Glucosidase Inhibition of Compounds 164, 186-197 113 CONTENTS Chapter # 6: Experimental 115 6.1 Plant Material 116 6.2 Extraction and Isolation 116 6.3 Acid Hydrolysis of Compounds 186 and 197 118 6.4 α-Glucosidase Inhibition Assay 118 6.5.1 Characterization of Stewartiiside (186) 119 6.5.2 Characterization of Stewertiisin A (187) 121 6.5.3 Characterization of Stewertiisin B (188) 122 6.5.4 Characterization of Stewertiisin C (189) 123 6.5.5 Characterization of Notohamosin A (190) 124 6.5.6 Characterization of Phlomispentanol (191) 125 6.5.7 Characterization of Oleanolic acid (164) 126 6.5.8 Characterization 2-Hydroxybenzoic acid (192) 127 6.5.9 Characterization 4-Hydroxybenzoic acid (193) 128 6.5.10 Characterization Caffeic acid (194) 129 6.5.11 Characterization of Tiliroside (195) 130 6.5.12 Characterization of Isorhamnetin 3-(6-p-coumaroyl)-β-D- glucopyranoside (196) 131 6.5.13 Characterization of Lunariifolioside (197) 132 Chapter # 7: References 133 List of Publications 148 ACKNOWLEDGEMENT ACKNOWLEDGEMENT All praises to ALMIGHTY ALLAH, the most Beneficial, the most Merciful Who provided me not only this golden opportunity to enhance my skills, but also give me power and wisdom to work. I offer my humblest thanks from the core of my heart to the HOLY PROPHET (Peace be upon him) who is forever a model of guidance and knowledge for humanity. Foremost, I would like to express my sincere gratitude to my research supervisor Dr. Naheed Riaz for his continuous support, patience, motivation, enthusiasm, and immense knowledge during the completion of this work. His guidance, keen interest and constructive criticism were the real source of inspiration. I would like to thank the rest of all my teachers especially Prof. Dr. Abdul Jabbar, Dr. Muhammad Saleem, Prof. Dr. Faiz Ul Hassan Nasim, Dr. Muhammad Ashraf, Dr. Abdul Rauf, Dr. Shafquat Hussain and Dr. Muhammad Ashraf for their support, guidance, timely help, cooperation, encouragement and insightful comments during the completion of this work. I would like to acknowledge the support of the Higher Education Commission (HEC), particularly in the award of Indigenous 5000 Ph. D Fellowship program and International Research Support Initiative Program that provided the necessary financial support for this research. I also thankful to Dean of Science, Chairman, Department of Chemistry, Staff Library IUB, Technical and Non-technical staff of the Department of Chemistry for their support and assistance during the course of this study. Page i ACKNOWLEDGEMENT I would like to acknowledge of the best wishes to my friends especially Ansa Madeeha Zafar and special thanks are extended to my lab fellows Sara Mussadiq, Asia Tabussum, M. Akram Naveed, M. Imran Tousif, Nusrat Shafiq, Jallat Khan, Basharat Ali, Abdul Gaffar, my seniors and juniors for their valuable suggestions and encouragement during my stay at IUB. Last but not the least I owe my deep gratitude to my loving Father and Mother who educated me and enabled me what I am today, May Allah bless them with His best in this world and life after. I am also thankful to my Brothers and my Sister for their encouragement and being always there cheering me up and stood by me through the good and bad times. BUSHRA JABEEN Page ii SUMMARY SUMMARY The history of natural products is as ancient as human being and these are used to cure man since life started.
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