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Biosynthesis and Transport of Flavonol Sophorosides in Arabidopsis Thaliana Anthers

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Biosynthesis and Transport of Flavonol Sophorosides in Arabidopsis Thaliana Anthers Biosynthesis and transport of flavonol sophorosides in Arabidopsis thaliana anthers Dissertation zur Erlangung des Doktorgrades der Naturwissenschaften (Dr. rer. nat.) der Naturwissenschaftlichen Fakultät I – Biowissenschaften – der Martin-Luther-Universität Halle-Wittenberg, vorgelegt von Herrn Stephan Grunewald geb. am 10.05.1989 in Berlin Gutachter: 1. PD. Dr. Thomas Vogt 2. Prof. Dr. Ingo Heilmann 3. Prof. Dr. Enrico Martinoia Verteidigungsdatum: 18.01.2021 II Table of contents Table of contents List of abbreviations ....................................................................................... V List of tables ................................................................................................. VII List of figures............................................................................................... VIII 1 Introduction ............................................................................................. 1 1.1 The role of transport in plant secondary metabolism ............................................................ 1 1.2 Transporters of specialized metabolites ................................................................................. 2 1.2.1 ABC-transporters ............................................................................................................. 2 1.2.2 MATE-transporters .......................................................................................................... 3 1.2.3 The nitrate/peptide family (NPF-transporters) ............................................................... 4 1.3 Flavonoids: highly diverse compounds ................................................................................... 5 1.4 Biosynthesis of flavonol-3-O-sophorosides in A. thaliana ...................................................... 6 1.5 Flavonoid glycosylation ........................................................................................................... 8 1.5.1 Biological relevance of flavonoid glycosylation ............................................................... 8 1.5.2 Plant glycosyltransferases ............................................................................................... 9 1.5.3 Flavonol sophorosides ..................................................................................................... 9 1.6 Tapetum and pollen – A special relationship ........................................................................ 10 1.6.1 Angiosperm pollen development .................................................................................. 10 1.6.2 A special cell layer: the tapetum ................................................................................... 11 1.6.3 Composition of the pollen wall ..................................................................................... 13 1.7 Flavonoid transport in plants ................................................................................................ 14 1.8 Aim of this investigation ........................................................................................................ 17 2 Materials and methods ........................................................................... 18 2.1 Materials ................................................................................................................................ 18 2.1.1 Chemicals and biochemical reagents ............................................................................ 18 2.1.2 Media ............................................................................................................................. 18 2.1.3 Vectors ........................................................................................................................... 18 2.1.4 Bacterial strains ............................................................................................................. 19 2.1.5 Preparation of electrocompetent cells ......................................................................... 20 2.1.6 Plants and growth conditions ........................................................................................ 20 2.1.7 Isolation of T-DNA insertion lines .................................................................................. 20 2.2 Molecular methods ............................................................................................................... 21 I Table of contents 2.2.1 Isolation of genomic DNA .............................................................................................. 21 2.2.2 Isolation of plasmid DNA ............................................................................................... 21 2.2.3 Polymerase chain reaction (PCR) .................................................................................. 21 2.2.4 Agarose gel electrophoresis .......................................................................................... 22 2.2.5 RNA extraction and cDNA synthesis .............................................................................. 22 2.2.6 Quantitative real-time polymerase chain reaction (qRT-PCR) ...................................... 23 2.2.7 Classical cloning for recombinant protein expression .................................................. 24 2.2.8 Golden Gate Cloning ...................................................................................................... 25 2.2.9 Restriction analysis ........................................................................................................ 28 2.2.11 Site-directed mutagenesis ............................................................................................. 29 2.2.12 Sequencing and in silico analysis ................................................................................... 29 2.2.13 Transformation of electrocompetent cells ................................................................... 30 2.2.14 Generation of transgenic Arabidopsis lines .................................................................. 30 2.3 Microscopic methods ............................................................................................................ 31 2.3.1 Subcellular localization .................................................................................................. 31 2.3.2 Transient expression in N. benthamiana leaves ........................................................... 31 2.3.3 Isolation of protoplasts ................................................................................................. 32 2.3.4 Transformation of protoplasts ...................................................................................... 33 2.3.5 Promotor-GFP localization ............................................................................................ 33 2.3.6 Immunolabelling of anther cross-sections .................................................................... 34 2.3.7 Transmission electron microscopy (TEM) ..................................................................... 35 2.4 Protein biochemical methods ............................................................................................... 35 2.4.1 Protein concentration determination ........................................................................... 35 2.4.2 SDS-PAGE ....................................................................................................................... 35 2.4.3 Immunoblot analysis ..................................................................................................... 36 2.4.4 Heterologous expression and partially purification of glycosyltransferases ................ 37 2.4.5 Standard flavonol glycosyltransferase assays ............................................................... 38 2.4.6 Preparation of 14C-labelled flavonol glucosides ............................................................ 38 2.4.7 Transporter uptake assays with 14C-labelled flavonol glucosides ................................. 39 2.5 Analytical methods ................................................................................................................ 40 2.5.1 Harvesting of pollen material from Arabidopsis ........................................................... 40 2.5.2 Preparation of pollen and anther extracts .................................................................... 40 2.5.3 High performance thin-layer chromatography ............................................................. 40 2.5.4 High performance liquid chromatography .................................................................... 41 2.5.5 Gas chromatography-mass spectrometry ..................................................................... 41 II Table of contents 2.6 Biological assays .................................................................................................................... 41 2.6.1 Pollen viability assay ...................................................................................................... 41 2.6.2 In vitro pollen germination assay .................................................................................. 42 3 Results .................................................................................................... 43 3.1 The flavonoid glycosyltransferases UGT78D2 and UGT79B6 ................................................ 43 3.3 Transport and biosynthesis of flavonol sophorosides........................................................... 45 3.3.1 UGT79B6 is highly expressed in tapetal cells ...............................................................
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