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UNIVERSITY of NAPLES “FEDERICO II” DEPARTMENT of PHARMACY Ph.D. THESIS in “PHARMACEUTICAL SCIENCE”

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UNIVERSITY of NAPLES “FEDERICO II” DEPARTMENT of PHARMACY Ph.D. THESIS in “PHARMACEUTICAL SCIENCE” UNIVERSITY OF NAPLES “FEDERICO II” DEPARTMENT OF PHARMACY Ph.D. THESIS IN “PHARMACEUTICAL SCIENCE” Phytochemical and synthetic studies on bioactive secondary metabolites from Apiaceae plants growing in Mediterranean and Middle-East regions Supervisor: Coordinator: Prof. Daniela Rigano Prof. Maria Valeria D’Auria Candidate: Dr. Carmina Sirignano XXXI cycle 2015/2018 Look up at the stars and not down at your feet. Try to make sense of what you see, and wonder about what makes the universe exist. Be curious. (Stephen Hawking) Table of contents Table of contents Abstract ............................................................................................................... i Publications of the candidate during the PhD period ................................... ii CHAPTER 1 ...................................................................................................... 1 NATURAL PRODUCTS: A NEVER-ENDING INSPIRATION FOR DRUG DISCOVERY ........................................................................................ 1 1.1 Plants as a source of natural products ................................................................. 2 1.2 The role of synthetic chemistry in the natural products field ............................. 3 References ............................................................................................................. 7 CHAPTER 2 ........................................................................................................ TECHNIQUES AND METHODS EMPLOYED IN THIS STUDY ............ 9 2.1 Isolation procedures ............................................................................................ 9 2.2 Mass spectrometry ............................................................................................ 10 2.3 Nuclear Magnetic Resonance ............................................................................ 12 2.4 Determination of stereochemistry .................................................................... 14 2.4.1 Determination of relative configuration ................................................. 14 2.4.1.1 Murata’s Method ............................................................................. 15 2.4.2 Determination of absolute configuration ............................................... 17 2.4.2.1 Marfey’s Method ............................................................................. 17 2.4.2.2 Mosher’s Method ............................................................................ 17 2.4.2.3 Electronic circular dichroism ............................................................ 19 2.5 General Experimental Section for this PhD thesis ............................................. 20 References ........................................................................................................... 21 CHAPTER 3: ....................................................................................................... TRPA1 MODULATING C14 POLYACETYLENES FROM THE IRANIAN ENDEMIC PLANT ECHINOPHORA PLATYLOBA ................ 23 3.1 The Apiaceae family ........................................................................................... 23 3.1.1 Echinophora genus .................................................................................. 25 3.2 Polyacetylenes from Apiaceae family and their biosynthesis ........................... 28 3.3 Polycetylenes from Echinophora platyloba ....................................................... 31 3.4 Activity on transient receptor potential ion channels ....................................... 33 3.5 Experimental section ......................................................................................... 37 3.5.1 Plant material, extraction and isolation .................................................. 37 3.5.2 Spectroscopic data for the isolated compound ...................................... 38 3.5.3 Thermo TRPs Receptor Assays ................................................................ 38 Table of contents References ........................................................................................................... 40 CHAPTER 4: ....................................................................................................... PLASMODIUM TRANSMISSION BLOCKING AND ANTIPROLIFERATIVE METABOLITES FROM DAUCUS VIRGATUS, A TUNISIAN ENDEMIC PLANT ................................................................ 44 4.1 Daucus genus ..................................................................................................... 45 4.2 Malaria: a still alarming global burden .............................................................. 47 4.2.1 Plants traditionally used to treat malaria ............................................... 50 4.3 The biosynthesis of Daucus sesquiterpenes ...................................................... 52 4.4 Isolation and structural elucidation of angeloylated germacranolides with Plasmodium transmission-blocking activity ............................................................. 58 4.5 Absolute configuration of daucovirgolides ........................................................ 64 4.6 Plasmodium transmission-blocking activity ....................................................... 68 4.7 Antiproliferative metabolites from Daucus virgatus apolar extract .................. 72 4.7.1 Structural elucidation of the isolated metabolites ................................. 72 4.8 Antiproliferative activity .................................................................................... 77 4.9 Experimental section ......................................................................................... 79 4.9.1 Plant material, extraction and isolation .................................................. 79 4.9.2 Spectroscopic data for the isolated compounds .................................... 81 4.9.3 Evaluation of Transmission Blocking Activity .......................................... 84 4.9.4 Antiproliferative activity ......................................................................... 86 4.9.5 Computational Calculations .................................................................... 86 References ........................................................................................................... 88 CHAPTER 5: ....................................................................................................... STUDIES TOWARDS THE TOTAL SYNTHESIS OF DAUCOVIRGOLIDE G ................................................................................. 93 5.1 Total synthesis of germacrane sesquiterpenes ................................................. 93 5.1.1 The first total synthesis of a germacranolide: (+)-dihydrocostunolide... 93 5.1.2 The total synthesis of (+)-costunolide..................................................... 95 5.1.3 Total synthesis of (±)-acoragermacrone ................................................. 98 5.1.4 Baran’s approach to the formation of the germacranolides’ ten- membered carbocycle ..................................................................................... 99 5.2 Retrosynthetic analysis of daucovirgolide G .................................................... 100 5.3 Synthesis of daucovirgolide G .......................................................................... 101 5.3.1 Preparation of (2E,6E)-8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl acetate ....................................................................................................................... 101 Table of contents 5.3.2 Preparation of (2E,6E)-8-((tert-butyldimethylsilyl) oxy)-3,7-dimethylocta- 2,6-dien-1-ol (53) ........................................................................................... 102 5.3.3 Preparation of (2E,6E)-8-((tert-butyldimethylsilyl)oxy)-3,7-dimethylocta- 2,6-dienal (50) ................................................................................................ 103 5.3.4 Preparation of ethyl (2S,3R,4E,8E)-3,10-dihydroxy-5,9-dimethyl-2-(prop 1-en-2-yl)deca-4,8-dienoate (anti-55a) ......................................................... 104 5.3.5 Attempted synthesis of (2R,3R,4E,8E)-3,10-bis((tert- butyldimethylsilyl)oxy)-5,9-dimethyl-2-(prop-1-en-2-yl)deca-4,8-dien-1-ol (60). ................................................................................................................ 106 5.3.6 Preparation of (2R,3R,4E,8E)-3,10-bis((tert-butyldimethylsilyl)oxy)-5,9- dimethyl-2-(prop-1-en-2-yl)deca-4,8-dien-1-ol from anti-β-Hydroxy-ester and attempted oxidation to aldehyde. ................................................................. 107 5.4 Experimental section ....................................................................................... 108 References ......................................................................................................... 112 CHAPTER 6 ........................................................................................................ CONCLUSIONS ........................................................................................... 114 CHAPTER 7 ........................................................................................................ SPECTRAL DATA ....................................................................................... 116 Spectral data for CHAPTER 3 .................................................................................. 116 Spectral data for CHAPTER 4 .................................................................................. 118 Spectral data
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