Carotenoid Oxygenases from Camellia sinensis, Osmanthus fragrans, and Prunus persica nucipersica
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1 Carotenoid Oxygenases from Camellia sinensis, Osmanthus fragrans, and Prunus persica nucipersica - Kinetics and Structure - Von der Fakultatfur Lebenswissenschaften der Technischen Universitat Carolo-Wilhelmina zu Braunschweig zur Erlangung des Grades einer Doktorin der Naturwissenschaften (Dr. rer. nat.) genehmigte Dissertation von aus Susanne Baldermann Heiligenstadt
2 1. Intention 9 2. Background Camellia sinensis Carotenoid composition Flavor composition Enzymes Prunus persica nucipersica Flavor composition Carotenoid composition Osmanthus fragrans Flavor composition Carotenoid composition Carotenoids Flavor compounds formed by carotenoid degradation Carotenoid cleavage enzymes Enzymes Occurrence Classes and characteristics Particularities Biological functions of volatile carotenoid cleavage products Are carotenoid cleavage enzymes monooxygenases or dioxygenases? Structural aspects Location of carotenoid cleavage enzymes Characterization of the kinetics Proteins and protein purification Proteins Posttranslational modifications Extraction of proteins Precipitation of proteins Precipitation of proteins with organic solvents Isoelectric focusing Enzyme isolation by preparative chromatography Size exclusion chromatography Ion exchange chromatography Density gradient centrifugation Protein analysis Protein quantification 32
3 Polyacryl amide gel electrophoresis Detection of protein bands Mass spectrometry MALDI-TOF Edman degradation Special analytical techniques CCC CPC Results and Discussion Enzymatic assays Isolation of carotenoid cleavage enzymes Introduction Prunus persica nucipersica Camellia sinensis Isolation of tea enzymes by centrifugal precipitation chromatography Osmanthus fragrans aurantiacus Summary Kinetic characteristics Introduction Determination of the main carotenoids Camellia sinensis Osmanthus fragrans aurantiacus Prunus persica Temperature optima Activation energy ph-optimum Time course Km and v, Summary Structural aspects of the enzymes Introduction Isoelectric points Structural aspects of tea samples with different harvest times Determination of the molecular mass bysds-page Nectarines Determination of the molecular mass of enyzmes from spring and autumn tea 71
4 3.4.5 Determination of the exact molecular mass by MALDI-TOF Structural information resulting from MALDI-TOF experiments after digestion with trypsin Edman-degradation Summary Substrate specificity Introduction Osmanthus fragrans Prunus persica nucipersica Camellia sinensis Isolation of all-frans-lycopene by HSCCC Isolation of 9'-c/s-neoxanthin by HSCCC Specificity of the enzymes isolated from Camellia sinensis Influence of the carotenoid end group (a-carotene, p-carotene, lycopene) Influence of the substitution of a p-ring (p-carotene, zeaxanthin, canthaxanthin, astaxanthin) Lutein, 9'-c/s neoxanthin Structure activity relationship Determination of reaction products Summary Experimental Preparation of crude enzyme extracts Prunus persica nucipersica Camellia sinensis Osmanthus fragrans aurantiacus Preparation of acetone powder Isolation of carotenoid oxygenases from tea (Camellia sinensis) Isoelectric focusing (IEF) Size exclusion chromatography on Sephadex Centrifugal precipitation chromatography Determination of the osmosis rate between sample and solvent channel Determination of the critical solvent concentration Bradford assay for the determination of the critical solvent concentration Isolation of carotenoid oxygenases from nectarines (Prunus persica nucipersica) Density centrifugation with Percoll Anion exchange chromatography 111
5 4.4.3 Ultra filtration Isoelectric focusing Isolation of carotenoid oxygenases from Osmanthus fragrans Quantification of carotenoids by UV-spectroscopy Determination of the purity of carotenoid standards by HPLC-DAD Isolation and clean up of carotenoid standards p-carotene and a-carotene Zeaxanthin, astaxanthin, canthaxanthin Zeaxanthin, astaxanthin Canthaxanthin Lutein Isolation of all-jrans-lycopene by HSCCC Isolation of 9'-c/s-neoxanthin by HSCCC Enzymatic setups Determination of the main carotenoids in Japanese Green Tea Determination of the main carotenoids in Osmanthus fragrans HPLC-MS Preparation of the substrates Determination of the detection wavelength for the enzymatic assay Calculation of relative activities Calibration of carotenoid/tween 40 solutions Determination of enzymatic activity Activity screening in CPC output fractions Michaelis-Menten Kinetics Determination of the optimum temperature Calculation of the activation energy Detection of the optimal ph for the enzymatic reaction Determination of enzyme structure SDS-PAGE Coomassie Brilliant Blue Staining Coomassie Brilliant Blue Staining of PVDF membranes after Western blotting Silver Staining MALDI-TOF In gel digest Data base search Western Blot 133
6 4.17 Determination of the reaction products Determination after absorption on Bio-Beads SPME Chemicals Experimental Devices Photometer ph-meters Centrifuges Fast protein liquid chromatography (FPLC) instruments Preparative isoelectric focusing Eletrophoresis equiment Shaker Blotting High performance liquid chromatography (HPLC) instruments Mass spectrometry MALDI-TOF-MS High performance liquid chromatography mass spectrometry (HPLC-MS) High-speed counter-current chromatography (HSCCC) Centrifugal precipitation chromatography (CPC) Gas Chromatography (GC) Gas Chromatography mass spectrometry (GC-MS) Summary and Conclusion Zusammenfassung 145 Appendix 149 I LC-MS chromatograms of p-carotene at different NH 4Ac concentrations 149 II SDS-PAGE of spring and autumn tea samples after CPC 150 III Calibration of carotenoids/tween 40 solutions 0 1 g L ' 150 a-carotene/tween p-carotene/tween Zeaxanthin/Tween Lutein/Tween Astaxanthin/Tween Canthaxanthin/Tween Neoxanthin/Tween Lycopene/Tween IV PVDF membranes used for Edman degradation 154
7 V Data obtained by Edman degradation 155 VI Mass spectra of p-ionone 155 VII Structures and abbreviations of biogene amino acids 156 Literature Cited 157
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