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E-Copy Thesis Hajara Alfa.Pdf (11.03Mb) Faculty of Health and Life Sciences Leicester School of Pharmacy Phytochemical Investigation and Bioactivity Assessment of Medicinal Plant from Northern Nigeria A thesis submitted in partial fulfilment of the requirements for the degree of Doctor of Philosophy (Ph.D) in Natural Product Chemistry HAJARA HUSSAINI ALFA Supervisors Prof. Randolph Arroo Dr Ketan Ruparelia Dr Avninder Bhambra Prof. Adrian Slater October 2018 DEDICATION I want to dedicate this work to HIM whose hands alone hold sustenance, blessings and mercy. Page | i ABSTRACT Boswellia dalzielii (Burseraceae) has ethnopharmacological importance and is claimed to have anti-infection and immunomodulatory effects. In the Northern part of Nigeria, a region with a tropical dry climate, an aqueous infusion of this plant is used in the treatment of infections and tumours. The traditional formulation method was mimicked under laboratory conditions, and the effect of temperature and the impact of endophytic microbes present in aqueous infusion of B. dalzielii was also investigated. Activity-guided fractionation against Staphylococcus aureus and its methicillin-resistant strain resulted in the identification of two antibacterial compounds namely gallic acid and pyrogallol. The Minimum Inhibitory Concentration for pyrogallol and gallic acid against S. aureus growth are 508 and 753 µM, while against MRSA growth are 254 and 2032 µM, respectively. A growth Inhibition assay showed the activity of gallic acid as bacteriostatic, and pyrogallol as bacteriocidal against tested microorganisms. Interestingly, the bacteriocidal compound was found to arise by conversion of gallic acid by the endophyte Enterobacter cloacae. In addition, Pantoea spp was also isolated from the bark of B. Dalzielii. The sequences of both E. cloacae and Pantoea spp are deposited in the GenBank nucleotide database under the accession number MH764584 and MH764583, respectively. Similarly, activity-guided fractionation of B. Dalzielii bark against breast cancer cell line (MCF7) using MTT cytotoxicity assay resulted in the identification of a cytotoxic compound, catechol, and the half maximal effective concentration (EC50) observed was Page | ii 86µM. The growth inhibition effect of catechol was observed to be time- and concentration- dependent. Endophytic Klebsiella pneumonia species (strain A and B) were shown to be responsible for bioconversion of protocatechuic acid to catechol. In addition, Pantoea agglomerans was also isolated from the bark of B. dalzielii. The sequences of Klebsiella pneumonia A, Klebsiella pneumonia B and Pantoea agglomerans are deposited in the GenBank nucleotide database under the accession number MH762022, MH762023 and MH762024, respectively. All isolated compounds were identified using HPLC, TLC, NMR, FTIR and HRMS. Page | iii ACKNOWLEDGEMENT All praises and thanks to Allah, Lord of `Al-min for giving me the opportunity to conduct this study and peace be upon the most beloved messenger, Prophet Muhammad (S.A.W). I want to thank my first supervisor Dr. Arroo Randolph, for his unreserved patience, whose advice and encouragement were critical throughout the entire study. My gratitude goes to Dr Susannah Walsh, Dr Laura Smith, Dr. K. Ruparelia, Dr K. Beresford and Dr A. Bhambar for their patience and dedication in aiming to produce a fine researcher. And the entire laboratory technicians (especially Richard Smith and Abdul Razaaq) of the microbiology and chemical laboratory suites for putting up with me in their working environment and most importantly for their kind support and advice. I want to thank Gill Stephen and Alan Hogg for their professional advice and friendly support. Special thanks goes to the Tertiary Education Trust Fund (TETFUND) and the institute of Ibrahim Badamasi Babangida University for partially funding this study. I want to thank DMU maintenance and DMU security officials for making my work easier by providing me a clean and secure environment to conduct my research. My special regards go to my parents (Hussaini Alfa, Hauwa Sulaiman and Hauwa Muhammad Nagidi) for being there for me, making every phase of my life easy, supporting me with all their affection and making sure I understand the importance of knowledge. I would like to thank all of Siblings: Ibrahim, Fatima, Muhammad and Yakubu for their support, prayers and motivation. I will like to extend my gratitude to Prof. Baba Page | iv Alfa and Muhammad Suleyman for their advice and support during my research work. A special thanks to my cousin, Hassan Umar, for his support in ensuring the completion of this study. I thank all my family for their support and prayers. To Attiyyah Omerjee, Saman Yaqub, Aveen Hajj Man, Aminah Bugrara, Hanan Makki Zakari, Haafizah Hussaini, Rubab Talpur, Enrica Mancini, Maimuna Usman, Falila Bardi and Salamatu bint Yusuf, thank you for being part of my family, and for taking the responsibility of me being your sister. Shabnum Ahmed, I thank you for your time, listening ears and motivation, and Saman, words alone are not enough to emphasise your role during my study, all I can say is thank you. Ali Alqahtani and John Ogwu, I am grateful to have found brothers in a foreign land. I want to extend my regards and thanks to my friends and their family, Attiyyah Omerjee, Bruna Alvarez and Johanna Kostenzer. I want to thank Pat Adkin and all my friends for their contributions and support. Finally, a special thanks to Khaleed Algabbani, for his generous support, without your support I would not have completed my study. To my research colleagues, it was a great opportunity to have worked and studied alongside you all. Page | v CONFERENCES AND SYMPOSIUM ATTENDED Synergistic effect of Medicinal plants on micro-organisms and cancer cells. Alfa, H. et al. (2015). East Midlands Universities Conference, University of Lincoln, UK, September, 3rd, 2015. (Poster Presentation). Natural Research and The Post-antibiotic era: Identification and characterization of antimicrobials agents to control bacterial infection. Ianniella, F and Alfa, H (2016). Graduate Student Conference, De Montfort University, UK. (Oral Presentation) The antimicrobial efficacy of isolated compounds isolated against Staphylococcus aureus. Alfa, H. et al. (2016). 9th Joint Natural Product Conference, Copenhagen, Denmark, July 24th - 27th, 2016. (Oral Presentation) Pyrogallol is the main antibacterial compound in the aqueous extract of Boswellia dalzielii bark. Alfa, H. et al. (2017). Trends in Natural Product Research – PSE Young Scientists’ Meeting Lille 2017 Natural Products in Health, Agro-Food and Cosmetics – June 28th - July 1st, 2017. (Oral Presentation) Bioactivity of Medicinal Plants: Is it the Plant, Endophyte or Both? Alfa, H. et al. (2018). The 30th International Symposium on the Chemistry of Natural Products and the 10th International Congress on Biodiversity (ISCNP30 & ICOB10), Athens, Greece – November 25th - 29th, 2018. (Oral Presentation) Page | vi Table of Contents Contents DEDICATION ..................................................................................................................................... i ABSTRACT ....................................................................................................................................... ii ACKNOWLEDGEMENT .................................................................................................................... iv CONFERENCES AND SYMPOSIUM ATTENDED ................................................................................. vi Table of Contents .......................................................................................................................... vii Table of Figures ............................................................................................................................ xiii Table of Tables ............................................................................................................................ xvii 1 1 INTRODUCTION .............................................................................................................................. 1 SYNOPSIS ................................................................................................................... 2 BACKGROUND ........................................................................................................... 2 ETHNOPHARMACOLOGY ........................................................................................... 3 PLANT AS MEDICINE .................................................................................................. 5 CLINICAL APPLICATIONS OF HERBAL MIXTURES ................................................... 9 PERCEIVED DRAWBACKS ..................................................................................... 10 Boswellia dalzielii .................................................................................................... 13 PHYTOCHEMISTRY ............................................................................................... 15 PHARMACOLOGY ................................................................................................ 17 ISOLATION OF MEDICINAL COMPOUNDS ............................................................... 21 EXTRACTIONS ...................................................................................................... 21 PURIFICATION ..................................................................................................... 23 SPECTROSCOPY AND SPECTROMETRY ...............................................................
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