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Phytochemical Investigations on Boswellia Species

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Phytochemical Investigations on Boswellia Species PHYTOCHEMICAL INVESTIGATIONS ON BOSWELLIA SPECIES Comparative Studies on the Essential Oils, Pyrolysates and Boswellic Acids of Boswellia carterii Birdw., Boswellia serrata Roxb., Boswellia frereana Birdw., Boswellia neglecta S. Moore and Boswellia rivae Engl. Dissertation for the Fulfillment of the Requirements for the Degree of Dr. rer. nat. by Simla Basar Istanbul (Turkey) Hamburg 2005 1. Gutachter: Prof. Dr. Dr. h. c. Wittko Francke Institut für Organische Chemie, Universität Hamburg 2. Gutachter: Prof. Dr. Chris Meier Institut für Organische Chemie, Universität Hamburg 1. Prüfer Prof. Dr. Dr. h.c. Wittko Francke Institut für Organische Chemie, Universität Hamburg 2. Prüfer Prof. Dr. Uli Hahn Institut für Biochemie, Universität Hamburg 3. Prüfer Prof. Dr. Johannes Westendorf Institut für Toxikologie, Universitätkrankenhaus Eppendorf Tag der Disputation: 18 März 2005 The presented work was performed from February 2000 to September 2003 at the University of Hamburg, Institute of Organic Chemistry under the supervision of Prof. Dr. Wilfried A. König. I would like to express my sincere gratitude to Prof. Dr. Wilfiried A. König† for his constructive supervision, his scientific support as well as his indefinite motivation throughout this work. Dear Prof. Dr. Dr. h.c. Wittko Francke, I greatly appreciate your help and support during the preparation of the last version of the thesis. For my parents Sevim & Ercan Başar Acknowledgments First of all, I would like to express my sincere gratitude to my dear “Doktorvater”, Prof. Dr. Wilfried A. König†, who deceased at 19th November 2004. Throughout this work, I appreciated his guidance, financial and scientific support, and I am very grateful for the chance he gave me to work with him and learn from him. I thank Prof. Dr. Dr. h.c. Wittko Francke for his invaluable advise, support and efforts during the revision of the thesis. Thanks to all professors in the Institute for Organic Chemistry and in the Department of Chemistry for giving me the possibility to study at the University of Hamburg. Sincere thanks to Dr. Angelika Koch for her cooperation on this interesting topic. I gratefully appreciate financial and scientific support, her guidance, and her patience all the time. Dr. Hans-Peter Hanssen’s support during the correction of the thesis is gratefully acknowledged. I like to thank the members of AK König for creating a friendly atmosphere in the working group. Especially, I would like to thank Dr. Detlev H. Hochmuth for his guidance and immediate help at any time. I very much enjoyed the team work during the organisation of ISCD-14 as well as his scientific supervision. I also thank Dr. Claudia Paul for her constructive support and help starting from the first minute that I joined AK König. I like to thank my dear friends Dr. Julia Pruns, Dr. Iris Altug, and Minoo Khedmati for the pleasant time that we had. I like to thank my labor partner Rita Richter for the harmony she brought to the working place. I am thankful to my colleagues in AK Francke, especially Sven Possner and Karsten Fehler for their friendship. Invaluable help by Annegret Meiners and Manfred Preuße who measured infinite numbers of samples without any delay is gratefully acknowledged. Ganz herzlich danke ich meinen Freunden – die eigentlich meine Familie in Deutschland sind – der Familie Kalyoncu; besonders Selda und Bahadır Kalyoncu sowie Sigrid und Baki Kalyoncu, Ilka und Baha Kalyoncu mit Devin und Linda, Sevim und Şerifali Kalyoncu; für das Gefühl, das sie mir gegeben haben, zu Hause zu sein. Liebe Selda und lieber Bahadır, ich werde eure Unterstützung, Verständnis, Herzlichkeit und Liebe, die ihr mir gezeigt habt, niemals in meinem Leben vergessen. Besonders danke ich Zeynep Yunt für die Motivation und herzliche Liebe, die sie mir jede Minute entgegen brachte. Liebe Zeynep, ohne dein Lächeln wäre diese Zeit unerträglich gewesen! Michael Maurer, dem ersten ehrlichen Mann in meinem Leben, danke ich herzlich für den Sonnenschein, den er mitgebracht hat, für seine liebevolle Führung und die Erfahrung, die er übertragen hat, und für das Lächeln, das er immer bei sich hat. Ich danke dir. Thanks to my brother, Semih Başar, who proved during the last years that he can work intercontinental as an IT-manager. One forgets the word, “loneliness”, as soon as your voice is on the phone. I like to specifically thank my beloved parents, Sevim and Ercan Başar, for their love, understanding and support from the moment that I was born. Without the peaceful atmosphere at home that they created, I would have not reached this point in my life. They have done the greatest work during these five years with their patience, with their energy they have sent to me, and with their prays. Contents 1 Introduction ................................................................................................................ 1 2 Aim of the Study ........................................................................................................ 5 3 General Part................................................................................................................ 7 3.1 Plant Metabolites........................................................................................................ 7 3.2 Isoprenoids: Terpenes, Terpenoids and Steroids........................................................ 9 3.2.1 Biosynthesis of Isoprenoids ..................................................................................... 13 3.2.1.1 Biosynthesis of Isopentenyl diphosphate via Acetate-Mevalonate Pathway ........... 13 3.2.1.2 Biosynthesis of Isopentenyl diphosphate via the Deoxyxylulose Phosphate Pathway .................................................................................................................... 15 3.2.1.3 Biosynthesis of Isoprenoids from Isopentenyl diphosphate..................................... 20 3.2.1.4 Biological Significance of Terpenoids and Other Secondary Metabolites .............. 23 3.3 Essential Oils............................................................................................................ 24 3.4 Natural Resins.......................................................................................................... 25 4 Methods Used for The Analysis of Plant Extracts ................................................... 29 5 Chemical Investigations on Boswellia Species ........................................................ 35 5.1 Botanical Aspect of Boswellia ................................................................................. 35 5.2 The Chemical History of Olibanum......................................................................... 36 5.3 Investigated Material................................................................................................ 41 5.4 Essential oil of Olibanum......................................................................................... 41 5.4.1 Essential Oil of Boswellia carterii Birdw. ............................................................... 42 5.4.1.1 Isolation and Identification of Verticilla-4(20),7,11-triene (1)................................ 44 5.4.1.2 Isolation and Identification of Incensyl acetate (2).................................................. 52 5.4.2 Essential Oil of Boswellia serrata Roxb.................................................................. 59 5.4.2.1 Isolation and Identification of 5,5-Dimethyl-1-vinylbicyclo-[2.1.1]hexane (3) ...... 62 5.4.2.2 Isolation of m-Camphorene (4) and p-Camphorene (5)........................................... 67 5.4.2.2 Identification of m-Camphorene (4) ........................................................................ 68 5.4.2.3 Identification of p-Camphorene (5).......................................................................... 75 5.4.3 Essential Oil of Boswellia frereana Birdw. ............................................................. 81 5.4.3.1 Dimer of α-phellandrene (7) .................................................................................... 84 5.4.4 Essential Oils of Boswellia neglecta S. Moore and Boswellia rivae Engl............... 91 5.4.5 Comparison of Essential Oils of Boswellia Species................................................. 94 5.5 Headspace-SPME Studies on Boswellia Species..................................................... 97 5.5.1 Headspace-SPME experiments with Boswellia carterii Birdw. .............................. 98 5.5.2 Headspace-SPME experiments with Boswellia serrata Roxb. .............................. 101 5.5.3 Headspace-SPME experiments with Boswellia frereana Birdw............................ 103 5.6 Comparative Studies on the Acid Fraction of Olibanum ....................................... 107 5.6.1 Boswellic Acids...................................................................................................... 107 5.6.1.1 Leukotriene Biosynthesis, The Inhibitiory Role of Boswellic Acids and Their Additional Medicinal Effects........................................................................ 108 5.6.2 Comparison of the Extraction Methods of Boswellic Acids.................................. 114 5.6.2.1 Detection of the Boswellic Acids........................................................................... 114 5.6.2.2 Analysis of Acid Fractions of B. carterii and B. serrata Determined by The Use of Different Basic Extractions ................................................................ 132 5.6.3 Stability Testing of Boswellic acids......................................................................
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