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Phytochemical and Antimicrobial Studies of the Leaves PHYTOCHEMICAL AND ANTIMICROBIAL STUDIES OF THE LEAVES EXTRACT OF PILIOSTIGMA THONNINGII SCHUM Milne - Redh (FABACEAE) BY FRIDAY ADIH ECHU DEPARTMENT OF PHARMACEUTICAL AND MEDICINAL CHEMISTRY, FACULTY OF PHARMACEUTICAL SCIENCES, AHMADU BELLO UNIVERSITY, ZARIA NIGERIA DECEMBER, 2014 i PHYTOCHEMICAL AND ANTIMICROBIAL STUDIES OF THE LEAVES EXTRACT OF PILIOSTIGMA THONNINGII SCHUM Milne – Redh (FABACEAE) BY Friday Adih ECHU (B. Pharm., A.B.U. 1997) M. Sc/PHARM. SCI/22426/2012 – 2013 BEING A THESIS SUBMITTED TO THE SCHOOL OF POSTGRADUATE STUDIES AHMADU BELLO UNIVERSITY, ZARIA IN PARTIAL FULFILMENT FOR THE AWARD OF MASTER OF SCIENCE IN PHARMACEUTICAL AND MEDICINAL CHEMISTRY DEPARTMENT OF PHARMACEUTICAL AND MEDICINAL CHEMISTRY, FACULTY OF PHARMACEUTICAL SCIENCES AHMADU BELLO UNIVERSITY, ZARIA – NIGERIA. DECEMBER, 2014 ii DECLARATION I declare that the work in this thesis entitled “PHYTOCHEMICAL AND ANTIMICROBIAL STUDIES OF THE LEAVES EXTRACT OF PILIOSTIGMA THONNINGII SCHUM. Milne – Redh (FABACEAE) has been performed by me in the Department of Pharmaceutical and Medicinal Chemistry under the supervision of Dr (Mrs.) H.S. Hassan and Prof. M.I. Sule. The information derived from the Literature has been dully acknowledged in the text and a list of references provided. No part of this dissertation was previously presented for another degree or diploma at any other University. Friday Adih ECHU …………………….. ……………….. Signature Date iii CERTIFICATION This dissertation entitled” PHYTOCHEMICAL AND ANTIMICROBIAL STUDIES OF THE LEAVES EXTRACT OF PILIOSTIGMA THONNINGII SCHUM. Milne – Redh (FABACEAE) by Friday Adih ECHU meets the regulations governing the award of Master of Science in Pharmaceutical and Medicinal Chemistry of Ahmadu Bello University, Zaria and is approved for its contributions to knowledge and literary presentation. Dr. (Mrs.) H.S. Hassan ………………….. .………………….. Chairman Supervisory Committee Signature Date Prof. M.I. Sule ………………….. ………………….. Member Supervisory Committee Signature Date Dr. Aliyu M. Musa ………………… ………………….. HOD Pharmaceutical and Medicinal Chemistry, Signature Date Ahmadu Bello University, Zaria.. Prof. A. H. Zoaka .. ..…………………… ….………………. Dean, School of Postgraduate Studies Signature Date Ahmadu Bello University, Zaria. iv DEDICATION This research work is dedicated first to GOD Almighty for the opportunity He had given me again to achieve this level of education and to my wife, Mrs. (Dcns) OJONUGWA D. ECHU and Children, OGECHA, OMA-AJUMA, ONENYI, OJIMA and OJONIMI. v ACKNOWLEDGEMENT I would like to express my sincere gratitude to my supervisors Dr. (Mrs.) H.S. Hassan and Prof. M.I. Sule for supervising this work and for their sincere advice, encouragements and corrections in the course of this work. I appreciate all you have both done to see the success of this work. My heartfelt thanks also to Bashar Bawa, Njinga Stanly, Sani Yahaya, Dr. Aliyu Musa (HOD Pharmaceutical and Medicinal Chemistry A.B.U. Zaria), Musa Yahaya Maikafi, Iliyasu Salisu., Mr Obeta Francis., Mr. Williams A., Joy Biko., Umar Usman Umar, Nafiu Garba, Ms Veronica Odinkemere and all other staff of the Department, all my brothers, sisters and their families lead by Mr. Bernard Onuche. My profound gratitude goes to Prof. Agunu Abdulkareem, Kamilu Mahmoud and Kabiru Ibrahim, all of Department of Pharmacognosy and Drugs Development A. B. U. Zaria, Dr. Busayo Olayinka, Department of Pharmaceutics and Pharmaceutical Microbiology both of Faculty of Pharmaceutical Sciences, A.B.U. Zaria, Prof. Augustin Ahmadu, Niger Delta University, Yenagoa – Bayelsa State, Prof. Iliya Ibrahim Faculty of Pharmacy, University of Maiduguri, Dr. (Pastor) David Abolude, Department of Biological Sciences, A.B.U. Zaria, Prof. M.D. Alegbejo, Department of Crop Protection, Institute for Agricultural Research, A.B.U. Zaria, Mal. Umar Hanwa, Samaru College of Agriculture, Division of Agricultural Colleges A. B. U. Zaria and my former H.O.D. General Hospital, Birnin Gwari Pharm. Mahmoud Muhammed, for his encouragement and contributions to the success of this work, I will forever be grateful to you. vi ABSTRACT The plant Piliostigma thonningii which is used in ethno - medicine for the treatment of wounds, ulcers and gingivitis was investigated for its chemical constituents and antimicrobial activity. The leaf of the plant was subjected to extraction procedures to obtain ethanol and n – hexane extracts. The n – hexane extract which was then subjected to preliminary phytochemical screening to revealed the presence of alkaloids, anthraquinones, flavonoids, reducing sugars, saponins, tannins and steroids/terpenes. The phytochemical technique employed was column chromatography. The antimicrobial activity of the n – hexane and ethanol extracts were studied using hospital isolates of ten pathogenic microorganismmms. Extensive chromatographic separation of the n – hexane fraction using silica gel column chromatography led to the isolation of a steroid. Stigmast-5-en-ol (β – Sitosterol), the structure was determined by spectral analysis including 1D and 2D NMR. In the antimicrobial studies, the extracts exhibit activity against six of the ten microorganisms with zone of inhibition ranging from 13 – 16 mm for n – hexane extract and 20 – 27 mm for ethanol extract while the zone of inhibition for the standard antibacterial drug sparfloxacin ranged from 40 – 46 mm and the zone of inhibition for the standard antifungal drug fluconazole ranged from 34 – 37 mm. The results obtained from this study suggest that the fractions of Piliostigma thonningii leaves extracts posses some compounds with antimicrobial activity and validate the ethnomedicinal use of the plant in the treatment of microbial infections. vii TABLE OF CONTENTS Content Page Cover page… … … … … … … … … … i Title page… … … … … … … … … … ii Declaration… … … … … … … … … … iii Certification … … … … … … … … … iv Dedication… … … … … … … … … … v Acknowledgement… … … … … … … … … vi Abstract… … … … … … … … … … vii Table of Contents… … … … … … … … … viii List of Tables …… … … … … … … … … xiii List of Figures …… … … … … … … … … xiv List of plates …… … … … … … … … … xvi List of Appendices … … … … … … … … … xvii List of Abbreviations …… … … … … … … … xviii CHAPTER 1: Introduction 1.1 General Introduction…. …… … … … … … … 1 1.2 Statement of Research Problems…… … … … … … 14 1.3 Justification … … … … … … … … … 14 1.4 Aim and Objectives of the Study… … … … … … 15 1.5 Research Hypothesis … … … … … … … … 15 viii CHAPTER 2: Literature Review 2.1 Botanical classification …… … … … … … 16 2.1.1 Common names …… … … … … … … … 16 2.1,2 Morphology of Piliostigma thonningii …… … … … … 17 2.2 Ethno - medicinal (Traditional) uses of Piliostigma thonningii …… … 18 2.3 Phytochemistry of Piliostigma thonningii and other species in the genus… 19 CHAPTER 3: Materials and Methods 3.1 Materials…… … … … … … … … … 22 3.1.1 Solvents and reagents… …… … … … … … … 22 3.1.2 Equipments… … … …… … … … … … 22 3.1.3 Collection, identification and preparation of plant material… …… … 22 3.2 Methods 3.2.1 Extraction…… … … … … … … … … 22 3.2.2 Preliminary phytochemical screening…… … … … … 24 3.2.2.1 Test for alkaloids… … … …… … … … … 24 3.2.2.2 Test for anthraquinones… …… … … … … … 24 3.2.2.3 Test for carbohydrates/reducing sugars … …… … … … 25 3.2.2.4 Test for flavonoids… … … …… … … … … 25 3.2.2.5 Test for glycosides… … … …… … … … … 26 3.2.2.6 Test for saponins… … … …… … … … … 26 3.2.2.7 Test for steroids/terpenes… … …… … … … … 27 3.2.2.8 Test for tannins… … …… … … … … … 27 3.2.3 Chromatographic Procedure/separation of n - hexane extract…… … 28 3.2.3.1 Column chromatography of n - hexane extract… … …… … 28 3.2.3.2 Solubility of compound B … … … … … …… … 29 ix 3.2.3.3 Chemical tests on compound B ….. … … … … … 29 3.2.3.4 Spectral analysis … … … …… … … … … 29 3.2.4 Antimicrobial Screening… … …… … … … … 30 3.2.4.1 Test microorganism… … …… … … … … 30 3.2.4.2 Preliminary antimicrobial studies… … …… … … … 30 3.2.4.3 Minimum inhibitory concentration (MIC)… … …… … … 31 3.2.4.4 Minimum bactericidal concentration/minimum fungicidal concentration (MBC/MFC) …… … … …… … … … … … 31 CHAPTER 4: Results 4.1 Percentage yields …… … … … … … … … 33 4.2 Results of Preliminary Phytochemical Studies .. … … … 34 4.3 Fractions of n – hexane extract chromatography …… … … … 35 4.4 Fractions of the merged fractions 12 & 13 chromatography……… … 36 4.5 Thin layer chromatography of compound B… … …… … … 37 4.6 Results of chemical tests … … … … …… … … 38 4.7 FTIR spectrum of compound B … … … …… … … 39 4.8 Proton nuclear magnetic resonance of compound B… … …… … 40 4.9 Carbon-13 nuclear magnetic resonance of compound B… …….. … 41 5.10 Distortionless enhancement by polarization transfer (Dept) of compound B…42 5.11 Results of susceptibility tests… … … … … … …… 43 4.8.2 The MIC and the MBC/MFC of the ethanol and n – hexane extracts of the leaves of P. thonningii on the test microorganisms … … … … … …… 44 x CHAPTER 5: Discussion 5.0 Extraction … …… … … … … … … … 45 CHAPTER 6: Summary, Conclusion, Recommendations and Contributions. 6.1 Summary… …… … … … … … … … 49 6.2 Conclusion… …… … … … … … … … 49 6.3 Recommendations …… … … … … … … … 50 References… … … …… … … … … … … 51 xi LIST OF TABLES Table 4.1: Percentage yields of n – hexane and ethanol extracts of P. thonningii… 33 Table 4.2: Preliminary screening of ethanol and n – hexane extracts of leaves of P. thonningii … … …… … … … … … … … 34 Table 4.3: Column chromatography of the n – hexane extract …… … … 35 Table 4.4: Column chromatography of fractions 12 and 13 … …… … 36 Table
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