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Academiejaar 2002-2003 Academiejaar 2002-2003 ISOLATION AND STRUCTURAL ELUCIDATION OF NATURAL PRODUCTS FROM PENTAS BUSSEI K. Krause, PENTAS LANCEOLATA (Forsk.) Deflers AND PENTAS PARVIFOLIA Hiern (RUBIACEAE) ISOLATIE EN STRUCTUURBEPALING VAN NATUURPRODUCTEN UIT PENTAS BUSSEI K. Krause, PENTAS LANCEOLATA (Forsk.) Deflers EN PENTAS PARVIFOLIA Hiern (RUBIACEAE) door JACQUES BUKURU Thesis submitted in fulfilment of the requirements for the degree of Doctor (Ph.D.) in Applied Biological Sciences: Chemistry Proefschrift voorgedragen tot het bekomen van de graad van doctor in de Toegepaste Biologische Wetenschappen: Scheikunde Op gezag van Rector: Prof. Dr. A. DE LEENHEER Promotoren: Decaan: Prof. Dr. ir. N. DE KIMPE Prof. Dr. ir. H. VAN LANGENHOVE Dr. L. VAN PUYVELDE COPYRIGHT The author and the promoter give the authorisation to consult and to copy parts of this work for personal use only. Any other use is limited by the Laws of Copyright. Permission to reproduce any material contained in this work should be obtained from the author or promoter. De auteur en de promotor geven de toelating dit doctoraatswerk voor consultatie beschikbaar te stellen, en delen ervan te kopiëren voor persoonlijk gebruik. Elk ander gebruik valt onder de beperkingen van het auteursrecht, in het bijzonder met betrekking tot de verplichting uitdrukkelijk de bron te vermelden bij het aanhalen van de resultaten uit dit werk. June 2003, Ghent, Belgium De auteur: Jacques BUKURU De promotor: Prof. Dr. ir. N. De KIMPE To my brothers T. Ngarukiyinka, J. Murengerantwari and A. Butoyi. Dedicated to all the Burundians for their hunger for peace, science and development. Examination committee Promoters • Prof. Dr. ir. N. De Kimpe Department of Organic Chemistry, Faculty of Agricultural and Applied Biological Sciences, Ghent University, Ghent, Belgium • Dr. L. Van Puyvelde Project Leader-TIBOTEC Natural Products Drug Discovery, Cau Glay – Hanoi – Vietnam Chairman • Prof. Dr. ir. J. Viaene Department of Agricultural Economy, Faculty of Agricultural and Applied Biological Sciences, Ghent University, Ghent, Belgium Members • Prof. Dr. L. Pieters Laboratory of Pharmacognosy and Phytochemistry, Department of Pharmaceutical Sciences, University of Antwerp, Antwerp, Belgium • Prof. Dr. ir. P. Van Damme Department of Plant Production, Faculty of Agricultural and Applied Biological Sciences, Ghent University, Ghent, Belgium • Prof. Dr. T. van Beek Laboratory of Organic Chemistry, Phytochemical Section, Wageningen University, Wageningen, The Nederlands • Prof. Dr. ir. C. Stevens Department of Organic Chemistry, Faculty of Agricultural and Applied Biological Sciences, Ghent University, Ghent, Belgium • Prof. Dr. ir. W. Steurbaut Department of Crop Protection, Faculty of Agricultural and Applied Biological Sciences, Ghent University, Ghent, Belgium • Dr. P. Wigerinck TIBOTEC, Mechelen, Belgium Preface It may be considered as a common thing, which is not more than a habit, to express gratitude at the end of a PhD research work like mine. However, let me wish all the individual persons and all the institutions mentioned here to find, through the following lines, a sincere and deep expression of what I have and I feel in my heart about them, upon the termination of my PhD thesis. First of all, my deepest appreciation is expressed to my promoters, Prof. Dr. ir. N. De Kimpe and Dr. L. Van Puyvelde, for their guidance and continuous help throughout the course of my doctororate studies. The supervision and criticism of Prof. Dr. ir. N. De Kimpe have been very crucial. Under his guidance, I have learnt science and I have made my real first steps in widely sharing knowledge, as attested by the high quality publications we have made together. I am grateful to him for having shared with me his high level scientific skill. The long experience of Dr. L. Van Puyvelde in the isolation of natural products, together with his long stay in Africa (Rwanda) have been beneficial to me from both the technical and the human point of vue. I am very thankful to him. Nothing could have been done without the financial support of my country throughout these years of hard work. I am highly grateful to The Republic of Burundi for this financial support. May the University of Ghent (Commission of Scientific Research of the Faculty of Agricultural and Applied Biological Sciences) also find here my gratitude for a two-months financial support at the very end of my studies. This support has been of a great rescue for me and my whole family. With all respect and gratitude, I refer to Prof. Dr. N. Schamp, the former head of the Department of Organic Chemistry, for having played a key role which lead to my admission at Ghent University. Through the collaboration I had with the late Prof. Dr. H. L. De Pooter since 1991, I knew Prof. Dr. N. Schamp only indirectly. After my Master Degree in Pharmaceutical Sciences at the Catholic University of Louvain in 1998, he welcomed me and introduced me to Prof. Dr. ir. N. De Kimpe. My special thanks also go to Prof. Dr. ir. H. Van Langenhove, the dean of the Faculty of Agricultural and Applied Biological Sciences, for his concern about me. I am very much grateful to Prof. Dr. ir. R. Verhé, the head of the Department of Organic Chemistry for his kindness and encouragement. I would like to thank the members of the reading committee: Prof. Dr. ir. C. Stevens, Prof. Dr. L. Pieters, Prof. Dr. T. van Beek, Dr. L. Van Puyvelde and Prof. Dr. ir. N. De Kimpe for their critical evaluation of my thesis. The contribution of the examination committee including Prof. Dr. ir. J. Viaene, Prof. Dr. ir. P. Van Damme, Prof. Dr. ir. W. Steurbaut and Dr. P. Wigerinck is also highly appreciated. I also appreciate the key contribution of Mr. Simon G. Mathenge and Mr. Francis P. Mudida (Botany Department, University of Nairobi, P. O. Box 30197, Nairobi, Kenya, and TRAMEDA, P. O. Box 66514, Nairobi, Kenya) for providing all the plant materials used for this research. I am thankful to Dr. Tuyen Van Nguyen from Vietman for his crucial contribution to my research work, particulary for all the time we spent together discussing my results, even Saturday. I will always remember positively his contribution to the articles I wrote. I would not forget to thank all the people of the Department of Organic Chemistry, Secretaries, Scientific staff, PhD students and students from Belgium and elsewhere, for their kind help and friendly cooperation. My heartfelt thanks go to my dear wife Evelyne. Her understanding, tolerance and love during so many years when most of the time I was away from home are deeply appreciated for the rest of my life. Had I known before the heavy sacrifices she was going to suffer of and endure, I am afraid that I would have hesitated to start the PhD studies! I wish her to consider that this research work is also hers! Last not the least, I would like to thank my daughters Rachel and Aurore, although not yet old enough to read and understand what I am writing at this moment. They often knocked on the door of my home office at the moments I needed silence around me, bringing to me, however, the nice and funny drawings they had been making all the day long and saying: “Open the door! We have our own works to show you!” Probably unaware of that, they provided me with a psychological refreshment, and I have learnt from them what is responsibility. I wish them to do more than I have done and to succeed where I failed! Should there be anyone I failed to acknowledge, my sincere regret, my apology and my thanks go to him/her too. Jacques BUKURU Ghent, June 2003 TABLE OF CONTENT Chapter I. GENERAL INTRODUCTION ............................................................................. 1 I.1. Nature: An Invaluable Source of Useful Chemical Agents ............................................... 3 I.1.1. Survey of Plant-derived Drugs .................................................................................... 4 I.1.1.1. Infectious Diseases Area ........................................................................................ 5 I.1.1.2. Neurological Diseases Area ...................................................................................8 I.1.1.3. Cardiovascular and Metabolic Diseases Area ....................................................... 9 I.1.1.4. Immunological, Inflammatory, and Related Diseases Area .................................. 9 I.1.1.5. Oncological Diseases Area .................................................................................... 11 I.1.2. Agrochemicals of Plant Origin .................................................................................... 12 I.1.2.1. General Overview .................................................................................................. 12 I.1.2.2. Few Examples of Plant-derived Insecticides ......................................................... 14 I.2. Rubiaceous Plants in African Folk Medicine .................................................................... 19 I.2.1. Biologically Active Species ......................................................................................... 19 I.2.2. Studies on Plant Species of the Genus Pentas ............................................................. 21 I.2.2.1. Phytochemical Investigation of Pentas longiflora Oliver ..................................... 22 I.2.2.2. Phytochemical Investigation of Pentas zanzibarica (Klotsch) Vatke ................... 25 I.3. Purpose and Goal of the Present Research .......................................................................
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