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People's Democratic Republic of Algeria Ministry of Higher Education and Scientific Research Mentouri Brothers University Constantine 1 Faculty of Exact Sciences Department of Chemistry Ranking No:……… Serial No:…………. Thesis Submitted for Doctorate Degree in Science In Organic Chemistry Option: Phytochemistry By Labib Ali Saeed Noman Secondary metabolic components and biological effectiveness study on two species Thymelaea microphylla and Gnidia somalensis Members of jury: Prof. Akkal Salah Mentouri Brothers University Constantine President Prof. Zellagui Amar Larbi Ben Mhidi - Oum El Bouaghi University Supervisor Prof. Rhouati Salah Mentouri Brothers University Constantine Co-Supervisor Prof. Gherraf Noureddine Larbi Ben Mhidi - Oum El Bouaghi University Examiner Prof. Seddik Khennouf Ferhat Abbas setif university Examiner 2017 DEDICATION I dedicate my thesis to my loving parent souls, whose words encourage me. Thank you both for giving me strength to reach for the stars and chase my dreams. You have successfully made me the person i am becoming. You will always be remembered. My brothers have never left my side. My dearest wife, who leads me through the valley of darkness with light of hope and support. I also dedicate this dissertation to my many friends and church family who have supported me throughout the research. My beloved kids, whom i can't force myself to stop loving and my wonderful son Raed for been there to replace me and for inspire him to complet his study. To my long-time friends; Abderrahmane Mezrag, Redoun, Mohamed Zabat, Omar, Ahmed, Farid, Amar, Seif, Abbey Andreas, Siham, Majdah, Fayroz, Hanan, Loisa for their support, friendship and encouragement. I dedicate my thesis to all researchers who have concern. Acknowledgements I would like to thank all the people who assisted me with their expertise, work or emotional support in the completion of this thesis. First, I would like to thank my supervisor, Professor Amar Zellagui for giving me the opportunity to undertake this study and for all his encouragement and assistance throughout the study period. I wish to express my appreciation to my “second” supervisor, Professor. Salah Rhouati, for his support throughout the course of this research. I have special thanks to jury members, Professor Salah Akkal, Professor Gherraf Noureddine and Professor Seddik Khennouf for accept to discuss and correct my thesis. I had a special word of thanks goes to Professor Ibrahim Demirtaş from Laboratory of Plant Research, Department of Chemistry, Faculty of Science, Uluyazi Campus, Karatekin University, Cankiri, Turkey and Dr. Susana M Cardoso, from Department of Chemistry & QOPNA, University of Aveiro, Portugal for excellent technical information and discussion, for being a real mentor to me and for finding the answers to every “difficult question”, they were a great source of optimism and passion of this part of chemistry. I would like also to acknowledge other postgraduate students and staff members in Chemistry Department, I would also like to thank my lab-team and my lab neighbors. Glossary of Abbreviations AREA : Agricultural Research and Extension Authority. CC : Column Cromatography. C : Collective. COSY : COrrelation SpectroscopY (NMR). C6 cells : rat brain tumor. 13C-NMR : 13C Nuclear Magnetic Resonance. d : doublet. dd : doublet of doublet. DAD : Diode Array Detector, UV. DEPT : Distorsionless Enhancement by Polarization Transfer (NMR). DMEM : Dulbecco’s modified eagle medium. diCQA : di-O-caffeoylquinic acid. DMSO-d6 : DiMethyl Sulf Oxyde hexa deuterated (NMR) ES : Electro Spray. F : Fraction. FBS : Fetal bovine serum. G : Gnidia. HeLa celles : Henrietta Lacks cells. Hetcore : Heteronuclear correlation spectroscopy. HMBC : Heteronuclear Multiple Bond Correlation. HMQC : Heteronuclear Multiple Quantum Correlation. 1H-NMR : 1H Nuclear Magnetic Resonance. HPLC-TOF : Liquide Chromatography/Time-of-Flight. Mass Spectrometry. Hz : Hertz. J: Coupling constant. LC-MS: Liquid chromatography–mass spectrometry. m : multiplet. MHI : Muller Hinton medium. MS : Mass Spectrometry. MSn : Multiple stage tandem MS. m/z : mass-to-charge ratio ppm : parts per million. Rt : Retention time. s : singlet. T : Thymelaea. TLC : Thin layer chromatography. UV : Ultraviolet. W : Waste. δ : chemical deplacement (NMR). Table of Contents Chapter 1 Summary ……….……….……………………………… …………………………………………… 1. Phenolic Compounds…………….……………………………… ……………………………… 01 1.1.Flavonoids………….………………………………………………………………......... 01 1.1.2. Structures and Classification of Flavonoids………………………...………………… 01 1.1.3. Chalcons …………………………….………………………………………………... 04 1.1.4. Flavones ……………………………….……………………………………………… 05 1.1.5. Flavanones………………………...…………..………………………………………. 06 1.1.6. Flavonols……………….……………………………………………………………... 07 1.1.7. Isoflavonoids………………………..……………………………………...………..... 07 1.1.8. Anthocyanins…………………………….……………………………………………. 08 1.2. 09 Coumarins………..……………………………..……………………………………….. 1.2.1. Classification and therapeutic applications of Coumarins……………………………. 10 1.3. Lignans………………………….………………………………………………………. 12 1.4. Spiro compounds……………………………………………………….……………….. 14 1.4.1. Nomenclature of Spiro compounds………………………………….………………... 14 1.5. Phenolic acids………………………………………..………………………………….. 15 1.6. Bioassays ……………… …………..………...…………….…...................................... 19 1.6.1. anti-cancer activity ……………… ………….……………………………………….. 19 1.6.2 Cancer and types ……………..…………….………………………………….. 20 1.6.3. Type of cancer……...….……………….……………………………………………... 21 1.6.4 Plant Derived Anti-Cancer Drugs…………………………………………………… 21 Chapter 2 2. Thymelaeaceae family ……………………………………………………………….….. 23 2.1. Classification of Thymelaeaceae family …………………...………………..…….......... 24 2.2. Thymelaeaceae family morphology ……..…………………….……………………….. 24 2.3. Phytochemical Aspects …………….…………………………………...……………… 25 2.3.1. Essential oils…………….……………………………….…………………………… 25 2.3.2. Terpenes…………....………………………………………. ………………………… 26 2.3.2.1. Monoterpenes …......................................................................................................... 26 2.3.2.2. Diterpenes ……….…………………………………………….……………………. 27 2.3.3. Coumarins ……………………………………………………….................................. 28 2.3.3.1. Simple Coumarins ……………………………...…………………………………... 29 2.3.3.2. Furanocoumarins …………………………………………………………………… 29 2.3.3.3. Bicoumarins ……………………………………..………………………………….. 29 2.3.3.4. Bicoumarin dibenzofuranic derivative ………………………………………...…… 30 2.3.3.5. Tricoumarins ……………………………………...………………………………… 31 2.3.4. Flavonoides ………………………………………….…............................................... 32 2.3.5. Lignans ………………………………………………………...........………………... 33 2.3.6. Spiro lactone…………………………………………………………….…………..... 34 2.3.7. Phenolic acid……………………………………………………………….................. 35 2.4. Biological Aspects ……………………………………………………………………… 36 2.5. Thymelaea genus ……………………………………….................................................. 37 2.5.1. Thymelaea genus Uses ……………………………………………….......................... 38 2.5.2. phytochemical of Thymelaea genus……………………………………….………….. 38 2.5.3. Thymelaea genus in Algeria………………………………………………...………… 39 2.5.4. Classification of Thymellaea microphylla Coss. et Dur.……………………..……...... 39 2.5.5. Thymellaea microphylla Coss. et Dur morphology...…..........................................…... 40 2.6. Gnidia genus …………………………………….………….…………………….…….. 40 2.6.1. Gnidia genus Uses …..………………………….. ...…………………………………. 43 2.6.2 phytochemical of Gnidia genus ……………….………………………………………. 43 2.6.3 Gnidia genus in Yemen……………………………………………………………...… 44 2.6.4. Classification of Gnidia somalensis Gilg. var.sphaerocephala (Bak.)Gastald ...……. 45 2.6.5. Gnidia somalensis Gilg. var.sphaerocephala (Bak.) Gastald. Morphology …………. 45 Chapter 3 3. Material and Methods ………………………………………………………….………. 46 3.1. Plant materiel of Thymelaea microphylla Coss. et Dur……………………..…………... 46 3.1.1. collection ……………………………………………………...…................................ 46 3.1.2. Preparation of extract ……...............................................………………………...…... 46 3.1.3. Separation and compounds purification …...…………..........................................…... 46 3.2. Plant material and methods of Gnidia somalensis Gilg. var.sphaerocephala (Bak.)Gastald. Extract………………………………………………………………….......... 51 3.2.1. collection ……………...………………………….. .....….….….................................. 51 3.2.2. Preparation of extract ……………...………….....……..………….……………….…. 51 3.2.3. Separation and HPLC-DAD-MS analyses ….....…...……............................................ 51 3.3. NMR measurements ……………...…….………………………………………..……... 52 3.4. HPLC-TOF-MS spectroscopy…………………………………………………………... 52 3.5. Bioassays …………...……….....………………..……………………………...……..... 54 3.5.1. Antiproliferative assay ………………..……………….……………………..……..... 53 3.5.1.1. Preparation the stock solutions ………..……………………………………..…....... 53 3.5.1.2. Cell lines and cell culture …….……..……………………………………..…......... 53 3.5.1.3. Cell proliferation assay ……...………………………………..………………..….... 53 3.5.1.4. Statistical analyses ……...………………………………….……...………..……..... 54 3.5.1.5. xCELLigence assay…………...……………………………………………………. 54 Chapter 4 4. Results and Discussion…………………………………………………………………... 56 4.1. Identification of compounds isolated from Thymelaea microphylla Coss. et Dur. …...... 56 4.1.1. Identification of Compound 1 ……...…………….....…..……...................................... 56 4.1.2. Identification of Compound 2 ……...……………...........…………………………….. 63 4.1.3. Identification of Compound 3 ……...……………...........……….…………………..... 72 4.1.4. Identification of Compound
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