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Quantification of Karrikins in Smoke Water Using Ultra-High Performance Liquid Chromatography-Tandem Mass Spectrometry

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Quantification of Karrikins in Smoke Water Using Ultra-High Performance Liquid Chromatography-Tandem Mass Spectrometry PALACKÝ UNIVERSITY IN OLOMOUC Faculty of Science Laboratory of Growth Regulators & Department of Chemical Biology New methods for karrikin analysis Ph.D. thesis Author : Mgr. Jakub Hrdlička Study programme: P1527 / Biology Study branch: 1501V019 / Experimental Biology Supervisor: Mgr. Karel Doležal, Dr., DSc. Consultant: Doc. Mgr. Ondřej Novák, Ph.D. Bibliographical identification Author’s first name and surname Mgr. Jakub Hrdlička Title of thesis New methods for karrikin analysis Type of thesis Ph.D. Department Laboratory of Growth Regulators Supervisor Mgr. Karel Doležal, Dr., DSc. The year of presentation 2021 Abstract Karrikins (KARs), chemically butenolide derivatives, are plant growth regulators that promote seed germination and the subsequent growth and development of seedlings of many plant species in extremely low concentration. This thesis presents a method development of a new analytical approach for quantification of KARs using ultra-high performance liquid chromatography with tandem mass spectrometry. Due to the employment of liquid chromatography-mass spectrometry using reverse phase-based separation and quantification by multiple reaction monitoring we developed, validated and applied a fast, specific and sensitive method which will give us the possibility to study these new interesting class of biostimulants in more detail. Keywords Karrikins, UHPLC–ESI-MS/MS, UniSpray Number of pages 48 Number of supplements 3 Language English 2 Acknowledgement This research was performed at the Laboratory of Growth Regulators and Department of Chemical Biology by Palacký University in Olomouc under the supervision of Mgr. Karel Doležal, Dr., DSc.. His support, understanding, patience and encouragement are greatly appreciated. This work would not exist without the excellent scientific supervision and great help of doc. Mgr. Ondřej Novák, Ph.D. Many thanks go to Dr. Tomáš Gucký and Dr. Martin Pošta for the synthesis of all available standards used in this thesis. I am also very grateful to Prof. Johannes Van Staden and his group from Research Centre for Plant Growth and Development, University of KwaZuluNatal Pietermaritzburg, South Africa for biological and smoke water samples. My special thanks go to Prof. Dr. Harro J. Bouwmeester, who supported my internship abroad at University of Amsterdam, Netherlands. I would like to thanks to all my lab colleagues for their assistance during my experiments and friendly atmosphere. Finally, I would like to thank to my family and my wife Eva for never-ending support to finish my studies. This work was supported by the IGA_PrF_2020_010. 3 Declaration Hereby I declare that this thesis summarizes original results obtained during my Ph.D. under the supervision of Mgr. Karel Doležal, Dr., DSc. and doc. Mgr. Ondřej Novák, Ph.D. using the literature sources listed in the References section. In Olomouc, Mgr. Jakub Hrdlička 4 Content List of papers ........................................................................................................................................... 6 Contribution report ................................................................................................................................. 7 Abbreviations .......................................................................................................................................... 8 1. Introduction ................................................................................................................................... 10 2. Aim and scopes .............................................................................................................................. 11 3. Literature review ........................................................................................................................... 12 3.1. Plant growth substances ....................................................................................................... 12 3.2. Karrikins ................................................................................................................................. 12 3.2.1. Origin of karrikins in nature ............................................................................................... 13 3.2.2. Karrikin signaling in Arabidopsis ........................................................................................ 14 3.2.3. Biological activities of karrikin ........................................................................................... 16 3.2.3.1. Seed germination .......................................................................................................... 16 3.2.3.2. Development of root system ......................................................................................... 17 3.2.3.3. Abiotic stress responses ................................................................................................ 17 3.2.4. Karrikin crosstalk with phytohormones ............................................................................ 18 3.3. Phytohormone analysis ......................................................................................................... 18 3.3.1. Sample preparation ........................................................................................................... 19 3.3.2. Chromatographic analysis ................................................................................................. 21 3.3.3. Mass spectrometry ............................................................................................................ 22 3.3.4. Quantification approaches ................................................................................................ 24 3.3.5. Method validation ............................................................................................................. 25 4. Materials and methods ................................................................................................................. 26 4.1. Chemicals and materials ........................................................................................................ 26 4.2. Biological materials ............................................................................................................... 26 4.3. Instrumentation .................................................................................................................... 27 4.4. Stability test ........................................................................................................................... 28 4.5. Extraction and purification method development ................................................................ 28 4.6. Validation experiments ......................................................................................................... 28 4.7. Sample preparation ............................................................................................................... 30 4.8. UHPLC-MS/MS conditions ..................................................................................................... 30 4.9. UniSpray optimization and validation ................................................................................... 31 5. Survey of results ............................................................................................................................ 32 5.1. UHPLC-ESI-MS/MS method development (Supplement I and III) ......................................... 32 5.2. Development of isolation protocol (Supplement I and III) .................................................... 33 5.3. Analytical method validation (Supplement I and III) ............................................................. 35 5.4. Karrikin quantification (Supplement I – III) ............................................................................ 36 5.5. Improvement in ionization of analytes (unpublished data) .................................................. 38 6. Conclusion and perspectives ......................................................................................................... 41 7. Reference ...................................................................................................................................... 42 5 List of papers This thesis is based on the following papers which are referred in the text by Roman numerals. The papers are attached at the end of the thesis in the Supplement section. I. Hrdlička J, Gucký T, Novák O, Kulkarni MG, Gupta S, Van Staden J, Doležal K (2019). Quantification of karrikins in smoke water using ultra-high performance liquid chromatography-tandem mass spectrometry. Plant Methods 15, 81. II. Gupta S, Hrdlička J, Ngoroyemoto N, Nemahunguni NK, Gucký T, Novák O, Kulkarni MG, Doležal K, Van Staden J (2020). Preparation and standardisation of smoke- water for seed germination and plant growth stimulation. Journal of Plant Growth Regulation volume 39, 338–345. III. Hrdlička J, Gucký T, Van Staden J, Novák O, Doležal K (2021). A stable isotope dilution method for a highly accurate analysis of karrikins. Plant Methods (accepted, 21. 3. 2021). 6 Contribution report I. As a first author, JH developed a separation and detection method, performed the experiments, validated the analytical methods and analyzed the karrikins in smoke waters. JH also wrote the manuscript. II. As a co-author, JH optimized the identification and quantification method and analyzed the karrikins and TMB in smoke waters. III. As a first author, JH developed a purification method and performed the experiments, validated the analytical methods
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