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Synthesis of Natural and Non-Natural Diarylheptanoids and Evaluation of Their Neuroprotective Activity

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Synthesis of natural and non-natural diarylheptanoids and evaluation of their neuroprotective activity Dissertation zur Erlangung des Doktorgrades der Naturwissenschaften (Dr. rer. nat.) der Fakultät für Chemie und Pharmazie der Universität Regensburg vorgelegt von Petr Jirásek aus Prag 2014 Gedruckt mit Unterstützung des Deutschen Akademischen Austauschdienstes Die vorliegende Arbeit wurde im Zeitraum vom Januar 2011 bis September 2014 unter der Leitung von Prof. Dr. Jörg Heilmann und PD Dr. Sabine Amslinger am Lehrstuhl für Pharmazeutische Biologie und am Institut für Organische Chemie der Universität Regensburg angefertigt. Das Promotionsgesuch wurde eingereicht am: Tag der mündlichen Prüfung: 29.09.2014 Prüfungsausschuss: Prof. Dr. Jörg Heilmann (Erstgutachter) PD Dr. Sabine Amsliger (Zweitgutachter) Prof. Dr. Sigurd Elz (dritter Prüfer) Prof. Dr. Siavosh Mahboobi (Vorsitzender) Danksagung An dieser Stelle möchte ich mich bei allen Personen bedanken, die zum Gelingen dieser Arbeit beigetragen haben: bei Prof. Dr. Jörg Heilmann für die Vergabe dieses spannenden Themas, für viele wertvolle Anregungen, sein Vertrauen und für die schöne Jahre in seiner Arbeitsgruppe; bei PD Dr. Sabine Amslinger für die lehrreiche Zeit in Ihrem Umfeld, für all die Hilfe in Sachen organischer Chemie und für die herzliche Aufnahme in Ihrem Arbeitskreis; mein besonderer Dank gilt dem Deutschen Akademischen Austauschdienst für die Finanzierung meiner Promotion; bei allen jetzigen und ehemaligen Kolleginen und Kollegen am Lehrstuhl für Pharmazeutische Biologie möchte ich mich für das besonders freundliche Arbeitsklima und ihre Hilfsbereitschaft ganz herzlich bedanken; mein Dank gilt natürlich auch meinen Laborkolleginen und Laborkollegen von AK Amslinger für die angenehme Laborzeit und viele anregende Disskusionen; bei Frau Gabriele Brunner für ihre Geduld und Hilfe bei allen praktischen Aspekten der alltägigen Laborarbeit, genauso wie bei Frau Anne Grashuber für ihre unabdingbare und freundliche Unterstützung bei der Betreung der Praktika; weiterhin möchte ich mich bei Dr. Daniel Bücherl, Dr. Sebastian Schmidt, Monika Untergehrer und Markus Löhr für die Hilfsbereitschaft beim Erklären aller Laborgeräte recht herzlich bedanken; Beata Kling und Dr. Hannelore Rücker gilt mein Dank für das Einführen in die Zellkultur, ihre freundliche Unterstützung und zahlreiche Tipps, ebenso wie Fulya Suzan Kücükoktay für ihre wertvolle Hilfe beim Durchführen mancher Zelltests; bei Dr. Paul Baumeister, Andreas Kreuzer, Anas Rasras, Dr. Ludwig Pilsl und Michel Leonhardt für die hilfreichen Disskusionen über organische Synthese; mein Dank geht auch an die NMR-spektroskopische Abteilung der Universität Regensburg, insbesonderen an Herrn Fritz Kastner, für das Aufnehmen zahlreicher Spektren und stets nette Hilfe bei allen Fragen; Herrn Josef Kiermaier und Herrn Wolfgang Söllner von der massenspektrometrischer Abteilung der Universität Regensburg danke ich für die Ermittlung aller MS-Daten; bei der Abteilung für Röntgenstrukturanalyse der Universität Regensburg möchte ich mich auch ganz herzlich bedanken; bei allen meinen Freunden möchte ich mich dafür bedanken, dass sie mir die Zeit in Regensburg unvergeslich gemacht haben und stets für die nötige Ablenkung gesorgt haben; bei meiner Nina möchte ich mich für ihre warme Unterstützung und ihre Geduld mit mir bedanken. Mein größter Dank geht an meine Familie, vor allem an meine Schwester Tereza und an meine Eltern Ivana und Petr, weil sie mir mein Studium und meine Promotion ermöglicht haben, an mich geglaubt haben und mich stets unterstützt haben. Ihnen widme ich diese Arbeit. List of abbreviations 1D one-dimensional 2D two-dimensional Aβ amyloid beta AD Alzheimer’s disease APCI atmospheric pressure chemical ionization aq. aqueous B2(pin)2 pinacolato diboron CAPE caffeic acid phenethyl ester CC column chromatography γ-GCS gamma-glutamoylcysteine synthase cGMP cyclic guanosine monophosphate CoA coenzyme A COSY correlation spectroscopy COX-2 cyclooxygenase-2 DIBAl-H diisobutyl aluminum hydride DIPEA diisopropyl ethyl amine DMAP 4-dimethylaminopyridine DMF N,N-dimethylformamide DMSO dimethyl sulfoxide dppf 1,1’-bis(diphenylphosphino)ferrocene EDC 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide EI electron-impact ionization eq. equivalent ERα estrogen receptor alpha ERK extracellular-signal regulated kinase ESI electro-spray ionisation EtOAc ethyl acetate EtOH ethanol eV electron volt FCS fetal calf serum GC gas chromatography Glc -D-glucose Glu glutamate GSH glutathione GTP guanosine triphosphate HCl hydrochloric acid HMBC heteronuclear multiple-bond correlation HMEC human microvascular endothelial cells HO-1 heme oxygenase 1 HPLC high-performance liquid chromatography HR high resolution HSQC heteronuclear single-quantum correlation IC50 half maximal inhibitory concentration IFN interferone IκBα inhibitor of kappa B, alpha IKK IκB kinase IL interleukin JNK c-Jun N-terminal kinase iNOS inducible nitric oxide synthase KOAc potassium acetate 12-LOX arachidonate 12-lipoxygenase LPS lipopolysaccharide MAPK mitogen activated protein kinase MAXIM. (Karl) Maximowicz MeOD methanol-d4 MeOH methanol Me2SO4 dimethyl sulfate MOM methoxymethyl MS mass spectrometry MTT 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide MW microwave irradiation NADH nicotinamide adenine dinucleotide NADPH nicotinamide adenine dinucleotide phosphate n-BuLi n-butyl lithium N-Cbz N-carboxybenzyl NF-κB nuclear factor-kappa B NMDA N-methyl-D-aspartat NMR nuclear magnetic resonance NOESY nuclear Overhauser effect spectroscopy NP normal phase Nrf2 nuclear factor-erythroid-2-related factor 2 p53 protein 53 PD Parkinson’s disease Pd/C palladium on charcoal PE petroleum ether (boiling point: 40-60 °C) Ph2S diphenyl sulfide PI3K/Akt phosphatidylinositol-4,5-phosphate 3-kinase/Akt PPh3 triphenylphosphine ppm parts per million p-TsOH para-toluenesulfonic acid R2 coefficient of determination Rf retardation factor ROS reactive oxygen species RP reversed phase r.t. room temperature s-GC soluble guanylyl cyclase SDS sodium dodecyl sulfate SN2 bi-molecular substitution SOD superoxide dismutase t-BuOOH tert-butyl hydroperoxide TFA trifluoroacetic acid TLC thin layer chromatography TNF tumor necrosis factor TPA 12-O-tetradecanoylphorbol-13-acetate tR retention time UV ultraviolet Content 1 Introduction ....................................................................................................................................................... 1 1.1 General classification of diarylheptanoids ......................................................................................... 1 1.2 Occurrence and structure of diarylheptanoids ................................................................................ 1 1.3 Biosynthesis of diarylheptanoids ........................................................................................................... 7 1.4 Synthesis of diarylheptanoids ............................................................................................................... 10 1.5 Biological activity of diarylheptanoids ............................................................................................... 18 1.5.1 Anticarcinogenic and anticancer effects ........................................................................................ 18 1.5.2 Anti-inflammatory activity ...................................................................................................................... 19 1.5.3 Antioxidant activity .................................................................................................................................... 21 1.5.4 Antimicrobial activity ................................................................................................................................ 21 1.5.5 Estrogenic activity ..................................................................................................................................... 22 1.5.6 Hepatoprotective activity........................................................................................................................ 23 1.5.7 Neuroprotective activity .......................................................................................................................... 23 2 Aim of the project ........................................................................................................................................ 25 3 Results and discussion ............................................................................................................................ 27 3.1 Synthesis of linear diarylheptanoids ................................................................................................. 27 3.1.1 Retrosynthetic approach towards linear diarylheptanoids .................................................... 27 3.1.2 Formation of the C6-C3 building block ............................................................................................. 28 3.1.3 Construction of the C6-C6 ketones .................................................................................................... 29 3.1.4 Synthesis of linear diarylheptanoids via Claisen-Schmidt condensation ...................... 30 3.1.5 Modifications of the aliphatic chain ................................................................................................... 31 3.1.6 Synthesis of further curcumin analogues ...................................................................................... 32 3.1.7 Synthesis of single
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  • Supplementary Material

    Supplementary Material

    Xiang et al., Page S1 Supporting Information Fig. S1. Examples of the diversity of diaspore shapes in Fagales. Fig. S2. Cladogram of Fagales obtained from the 5-marker data set. Fig. S3. Chronogram of Fagales obtained from analysis of the 5-marker data set in BEAST. Fig. S4. Time scale of major fagalean divergence events during the past 105 Ma. Fig. S5. Confidence intervals of expected clade diversity (log scale) according to age of stem group. Fig. S6. Evolution of diaspores types in Fagales with BiSSE model. Fig. S7. Evolution of diaspores types in Fagales with Mk1 model. Fig. S8. Evolution of dispersal modes in Fagales with MuSSE model. Fig. S9. Evolution of dispersal modes in Fagales with Mk1 model. Fig. S10. Reconstruction of pollination syndromes in Fagales with BiSSE model. Fig. S11. Reconstruction of pollination syndromes in Fagales with Mk1 model. Fig. S12. Reconstruction of habitat shifts in Fagales with MuSSE model. Fig. S13. Reconstruction of habitat shifts in Fagales with Mk1 model. Fig. S14. Stratigraphy of fossil fagalean genera. Table S1 Genera of Fagales indicating the number of recognized and sampled species, nut sizes, habits, pollination modes, and geographic distributions. Table S2 List of taxa included in this study, sources of plant material, and GenBank accession numbers. Table S3 Primers used for amplification and sequencing in this study. Table S4 Fossil age constraints utilized in this study of Fagales diversification. Table S5 Fossil fruits reviewed in this study. Xiang et al., Page S2 Table S6 Statistics from the analyses of the various data sets. Table S7 Estimated ages for all families and genera of Fagales using BEAST.