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Biologically-Active Secondary Metabolites of Foliar Endophytes of Conifers and the Understory Species Rhododendron Groenlandicum from the Acadian Forest

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Biologically-Active Secondary Metabolites of Foliar Endophytes of Conifers and the Understory Species Rhododendron Groenlandicum from the Acadian Forest BIOLOGICALLY-ACTIVE SECONDARY METABOLITES OF FOLIAR ENDOPHYTES OF CONIFERS AND THE UNDERSTORY SPECIES RHODODENDRON GROENLANDICUM FROM THE ACADIAN FOREST Natasha Claudia Prince A thesis submitted to the Faculty of Graduate Studies in partial fulfillment of the requirements for a degree of Master of Science Department of Chemistry Carleton University August 2015 Abstract Cronartium ribicola, the causative agent of white pine blister rust is damaging to all five-needle pine species. Existing methods of treatment are largely ineffective, resulting in the need of more innovative approaches. Research has shown that some conifer endophytes produce compounds that display potent antifungal activity, including towards haploid cultures of C. ribicola. Two conifer and one understory endophytes were studied here. Compounds 1 – 4, (1’Z)- dechloromycorrhizin A (1), mycorrhizin A (2), chloromycorrhizin A (3) and the new natural product 3-chloro-4-[(1Z)-1’-chloroprop-1’-en-1’-yl]-9-hydroxy-8,8-dimethyl-9,4,5,8-tetrahydro- 2H-1-benzopyran-5,2-dione (4) were isolated from L. papyraceum. Compounds 5 and 6 were produced by D. celastrina and were both identified as phomosolide A and a stable C10 pyrone respectively. The remaining compounds 2-(7-methoxy-2,5,6-trimethyl-4-oxo-4 H- benzo[d][1,3]dioxin-2-yl)propanoic acid (7), (E)-6-((3’-carboxybut-2’-en-2’-yl)oxy)-4-methoxy- 2,3-dimethylbenzoic acid (8) and 2-(6-(hydroxymethyl)-7-methoxy-2,5-dimethyl-4-oxo-4H- benzo[d][1,3]dioxin-2-yl)propanoic acid (9) were isolated from Seimatosporium sp. and are novel metabolites. All compounds possessed antimicrobial activity in B. subtilis, E. coli, S. cerevisiae and M. violaceum assays. i Acknowledgements Firstly, I give God thanks for His guidance and strength throughout the years of my graduate degree. Secondly, to my supervisor Dr. David Miller, thank you for the immeasurable support shown, as well as guidance concerning future educational paths. I must thank Dr. Tienabe Nsiama for his hard work and encouragement, as well as colleagues Dr. David McMullin for all his contribution and Blake Green mainly for his hard work as lab Dj. Many thanks to Dr. Keith Seifert, Dr. Joey Tanney and Dr. Allison Walker for their aid in providing and identifying the strains. Many thanks to Dr. Justin Renaud and Dr. Kevin Burgess for all their contribution in the chemical characterization of the compounds. Thirdly, a special thanks to the people who see me at my best and worst: my family and friends. Thanks to my family for their love and support. Thank you to my good friends Judy Chang, Corina Lim and Elisabeth Mantil for their prayers, support and for being my family away from home. This work was funded by the National Research Council of Canada, Industrial Research Assistance Program, the Natural Science and Engineering Research Council and JD Irving, Limited. ii Table of Contents Abstract ...................................................................................................................................................................i Acknowledgements ........................................................................................................................................ ii List of Figures .................................................................................................................................................... v List of Tables.................................................................................................................................................... vii List of reagents and supplies ..................................................................................................................ix Glossary ............................................................................................................................................................... xii 1. Introduction ...................................................................................................................................... 1 1.1 Fungi and plants ............................................................................................................................................ 1 1.1.1 Fungal endophytes ....................................................................................................................................... 1 1.1.2 Endophytes and conifers .............................................................................................................................. 5 1.1.3 Endophytes as mutualistic symbionts .......................................................................................................... 6 1.2 Primary and secondary metabolism ......................................................................................................... 8 1.2.1 Primary and secondary metabolites in plants ............................................................................................... 8 1.2.2 Primary and secondary metabolites in fungi ................................................................................................ 9 1.3 Pathogens and defense mechanisms in higher plants ......................................................................... 13 1.3.1 Conifer pathogens ...................................................................................................................................... 13 1.3.2 Endophytic secondary metabolites and host defense ................................................................................. 16 1.3.3 Endophyte mediated tolerance in conifers ................................................................................................. 17 1.4 Project Aim ................................................................................................................................................... 20 2. Materials and Methods ........................................................................................................................ 21 2.1 Fermentation ................................................................................................................................................. 21 2.2 Extraction, isolation and purification of metabolites .......................................................................... 24 2.2.1 Extraction ................................................................................................................................................... 24 2.2.2 Analysis ..................................................................................................................................................... 24 2.3 Biological activity assays ............................................................................................................................ 26 3. Results .............................................................................................................................................................. 28 3.1 Secondary metabolites from the Lachnum papyraceum strain ......................................................... 28 3.2 Secondary metabolites from the Diaporthe celastrina strain ............................................................. 38 3.3 Secondary metabolites from the Seimatosporium sp. strain .............................................................. 43 3.4 Antimicrobial assay results ....................................................................................................................... 55 3.4.1 B. subtilis ................................................................................................................................................... 56 3.4.1 E. coli ......................................................................................................................................................... 58 iii 3.4.3 S. cerevisiae ............................................................................................................................................... 59 3.4.4 M. violaceum .............................................................................................................................................. 60 4. Discussion ...................................................................................................................................................... 62 5. Conclusion ..................................................................................................................................................... 73 5. References ..................................................................................................................................................... 75 6. Appendix .......................................................................................................................................... 82 A: Identification of the strains grown in bulk ............................................................................................. 82 B: Spectroscopic data for compounds 1-9 .................................................................................................... 84 C: Bioassay graphs for compounds 1-9 ......................................................................................................... 99 D: Strain collection sites and preliminary bioassay screening results. ................................................ 112 iv List of Figures Figure Title Page Figure 1.1 A simple schematic of the general organization of fungi 1 Figure 1.2 A common needle endophyte Diaporthe sp., in photo is seen sporulating on 2 spruce twigs as they
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