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Ergosterol Biosynthesis in Green Algae and Its Phylogenetic Implications

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Ergosterol Biosynthesis in Green Algae and Its Phylogenetic Implications Ergosterol Biosynthesis in Green Algae and its Phylogenetic Implications by Matthew B. Miller, B.S. A Thesis In INTERDISCIPLINARY STUDIES Submitted to the Graduate Faculty of Texas Tech University in Partial Fulfillment of the Requirements for the Degree of MASTER OF SCIENCE Approved Committee: Dr. W. David Nes Chair of the Committee Dr. Robert W. Shaw Mark Sheridan Dean of the Graduate School August, 2014 Copyright 2014, Matthew B. Miller Texas Tech University, Matthew B. Miller, August 2014 ACKNOWLEDGMENTS Enormous gratitude goes to my mentor, Dr. W. David Nes. His guidance, knowledge and advice have been appreciated well beyond this thesis. I would like to thank Dr. Bard for the gift of the KD7 and KD21 C. reinhardtii mutants. I would also like to thank our collaborators, Dr. William Snell and Dr. Qian Wang for growing, modifying and maintaining all of the cultures provided to us. Many thanks to my laboratory co- workers, especially Dr. Brad Haubrich, Crista Thomas, Alicia Howard, Dr. Garrett Mohr, and Presheet Patkar. Working with you all was a pleasure, and your willingness to share your knowledge was much appreciated. To my mother and Father, I can’t imagine what the road would have been like if I didn’t have your unwavering support. Thank you for instilling in me a drive to succeed, and a stern hand when I needed it. Most of all, thank you for teaching me that if you want something, you had better be willing to work for it. ii Texas Tech University, Matthew B. Miller, August 2014 TABLE OF CONTENTS ACKNOWLEDGMENTS ................................................................................................. iii ABSTRACT ......................................................................................................................... v LIST OF TABLES ............................................................................................................ vii LIST OF FIGURES ........................................................................................................ viiii ABBREVIATIONS ........................................................................................................... ix CHAPTERS 1. STEROLS ....................................................................................................................... 1 1.1 Introduction ............................................................................................................... 1 1.2 Background ............................................................................................................... 1 1.3 Sterol Structure .......................................................................................................... 2 1.4 Sterol Nomenclature .................................................................................................. 3 1.5 Fungal and Algal Sterols ........................................................................................... 4 2. ISOLATION, IDENTIFICATION AND PURIFICATION OF STEROLS IN THE ALGA Chlamydomonas reinhardtii ................................................................................... 6 2.1 Materials and Methods .............................................................................................. 6 2.2 Extraction (NSF) ....................................................................................................... 6 2.3 GC ............................................................................................................................. 7 2.4 GC-MS ...................................................................................................................... 8 2.5 RP-HPLC .................................................................................................................. 9 2.6 NMR ........................................................................................................................ 10 3. RESULTS ..................................................................................................................... 12 3.1 Sterols of Chlamydomonas reinhardtii ................................................................... 14 3.2 Strengthening proposed the pathway ...................................................................... 16 3.3 Mutant studies ......................................................................................................... 17 3.4 25-Thialanosterol Inhibitor Study ........................................................................... 20 3.5 Isotopic labeling ...................................................................................................... 21 4. DISCUSSION ............................................................................................................... 24 4.1 Photosynthetic lineage............................................................................................. 27 4.2 Evolutionary Divergence......................................................................................... 28 BIBLIOGRAPHY ............................................................................................................. 30 APPENDIX iii Texas Tech University, Matthew B. Miller, August 2014 A. MASS SPECTROMETER ANALYSIS ..................................................................... 33 iv Texas Tech University, Matthew B. Miller, August 2014 ABSTRACT The green algae Chlamydomonas reinhardtii synthesizes the protosterol cycloartenol and converts it to ergosterol (C24-methyl) and 7-dehydroporiferasterol (C24-ethyl) through a highly conserved sterol C24- methylation-C25-reduction (25(27)- olefin) pathway that is distinct from the well described acetate-mevalonate pathway to fungal lanosterol and its conversion to ergosterol by the 24(28)-olefin pathway. 23 sterols were isolated and characterized by a combination of GC-MS and proton nuclear magnetic resonance spectroscopy analysis from a set of mutant, wild-type, and 25-thialanosterol- treated cells. The structure and stereochemistry of the final C24-alkyl sterol side chains possessed different combinations of 24-methyl/ethyl groups and 22(23)E and 25(27)- 2 double bond constructions. When incubated with [methyl- H3]methionine, cells incorporated three (into ergosterol) or five (into 7-dehydroporiferasterol) deuterium atoms into the newly biosynthesized 24-alkyl sterols, consistent only with a 25(27)- olefin pathway. Thus, our findings demonstrate that two separate isoprenoid-24-alkyl sterol pathways evolved in fungi and green algae, both of which converge to yield a common membrane insert ergosterol. v Texas Tech University, Matthew B. Miller, August 2014 LIST OF TABLES 3.1. Sterol composition of Chlamydomonas reinhardtii cells ...........................................13 3.2. Diagnostic signals for sterols submitted for 1HNMR from Chlamydomonas reinhardtii ..............................................................................................18 4.1. Detected sterols with chromatographic and spectral properties from Chlamydomonas reinhardtii ..............................................................................................25 vi Texas Tech University, Matthew B. Miller, August 2014 LIST OF FIGURES 1.1. Some known functions of sterols among cells ..............................................................2 1.2. The common tetracyclic sterol frame with the 1,2-cyclopentanoperhydro- phenanthrene ring system ............................................................................................3 1.3. A generic sterol structure showing the 4 domains ........................................................3 1.4. The two most common naming systems used for sterols .............................................4 1.5. Proposed biosynthetic route to ergosterol in Chlamydomonas reinhardtii ..................5 2.1. Dose Response of cholesterol on GC............................................................................8 2.2. Dose Response curve of ergosterol on analytical HPLC ............................................10 3.1. Capillary GC trace of Chlamydomonas reinhardtii wild-type cells ...........................15 3.2. Mass spectra of ergosterol, 7-dehydroporiferasterol and cycloartenol .......................16 3.3. Mass spectra and compound structures for cyclolaudenol and 24(28)- methylenecycloartenol ................................................................................................20 3.4. High end mass spectra of ergosterol and 7-dehydroporiferasterol incubated with 3 [methyl-2H ]-methionine.............................................................................................22 3.5. The sterol C24-alkylation/reduction pathways to alkylated products.........................23 4.1. Proposed sterol pathway from cycloartenol to end products in Chlamydomonas reinhardtii ...................................................................................................................26 A.1. Ergosta-5,7,22,25(27)-tetraenol .................................................................................33 A.2. Ergosta-5,7,22-trienol ................................................................................................34 A.3. Ergosta-5,7,25(27)-trienol ..........................................................................................35 A.4. Ergosta-5,7-dienol ......................................................................................................36 A.5. Ergosta-7,25(27)-dienol .............................................................................................37 A.6. Poriferasta-5,7,25(27)-trienol.....................................................................................38
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