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Industrial Applications of Plant Secondary Metabolites Dissertation Industrial Applications of Plant Secondary Metabolites Dissertation Presented in Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School of The Ohio State University By Yun Lin Graduate Program in Horticulture and Crop Science The Ohio State University 2017 Dissertation Committee: Dr. Joshua Blakeslee, Advisor Dr. Joseph Scheerens Dr. John Cardina Dr. Thaddeus Ezeji Dr. Stephanie Strand Copyright by Yun Lin 2017 Abstract Plant secondary metabolites (PSMs) constitute a broad range of compounds produced by plants both as part of normal developmental processes and in response to environmental stimuli. While plants produce PSMs to aid in their own growth and development (or as part of adaptive growth responses, PSMs have been co-opted by humans for use in multiple industries. For example, PSMs are heavily used in the food, pharmaceutical, and agricultural industries. Because of this, there is increasing demand for the isolation and identification of novel PSMs for industrial use. The work presented here details efforts to identify and characterize novel PSMs for used in the pharmaceutical and agricultural industries, as well as efforts to apply new methods developed for PSM research to the biomedical field. The first part of the research presented here details work investigating the medicinal properties of burdock extracts, which have traditionally been used in the Amish community to treat burn wounds. Our data indicate that extracts from two burdock species, A. lappa and A. minus exhibit significant anti-microbial activity against seven burn wound-associated pathogens in three types of anti-bacterial assays. Additionally, we used metabolomic profiling (spectrophotometric assays, HPLC, LC-MS/MS, and GC-MS) to identify putative anti-microbial compounds. Our results indicate that, while leaf extracts of both species exhibited anti-microbial effects against all the seven pathogens, A. ii minus extracts were in general more effective. Consistent with this, A. minus extracts contained more phenolic compounds, specifically flavonoids and hydroxylcinnamic acids than did corresponding A. lappa extracts. Potential anti-microbial compounds were putatively identified, including hydroxycinnamic acids, flavonoids, and fatty acids. Further work was focused on optimizing agriculture applications of PSMs. Chapter 3 details the development of a portable, field-deployable, and weather resistant 2,4-D drift detection system exhibiting high sensitivity to the target herbicide. The detector can be set with crops in field and collected for LC-MS/MS analysis when potential symptoms of 2,4-D damage are observed. The detection system was sensitive enough to detect 2,4-D 300 feet away from the spray swath. Five types of matrices were tested, and one of these was ultimately selected for its ability to partially resist ran, fully resist UV light, and fully resist long-term exposure to the greenhouse environment. In chapter 4, a fast, sensitive, and cost efficient LC-MS/MS quantification method for a potential pesticide compound (2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one) was developed and used to screen maize parental lines. While previous efforts to quantify DIMBOA have used a complex, multi-step purification process, the method developed here uses a straightforward two- step 90% methanol extraction and was used to successfully detect and quantify DIMBOA from 25 maize parental lines. Finally, chapter 5 describes the application of metabolomic (analytical chemistry) techniques developed during the course of our PSM research to characterize biomarkers associated with human diseases. Protocols to extract, isolate, identify, and quantify phospholipids, fatty acids, and cholesterol, were developed using three model plant iii organisms (guayule, moringa, burdock, respectively). The developed methods were then successfully adapted to screen murine tissues for selected lipid-type metabolites potentially of interest as early cancer biomarkers. iv Acknowledgements I would like to thank my advisor Dr. Joshua J. Blakeslee for all the help and support during the course of my Ph.D. life. Thank you for all the smart ideas and always having the answer to all types of questions I have. I’d also like to thank my SAC member Dr. Joseph C. Scheerens for the great plant secondary metabolite class, the kindness to share equipment, and all the advises he has patiently provided. Dr. Stephanie Strand, another SAC member of mine and a very encouraging person, taught me a lot in the area of microbiology and provided great suggestions for my research writing. I’d also like to acknowledge Dr. Thaddeus Ezeji for asking questions that lead me think and proposing valid concerns about my projects. My SAC member, Dr. John Cardina has been very helpful providing great advices about my research and also very kind and supportive. My gratitude also goes to Dr. Ann Chanon, who has patiently taught me a lot of lab techniques and constantly help me with everything in the lab. I’d also like thank Jinshan Lin, who taught me a lot about analytical techniques and LC-MS/MS knowledge. My lab mate, Eun Hyang (Grace) Han has been very supportive, provided me with experimental tips, helped me with the messes I made, and shared depressed moments with me. Dominic Petrella, has provided great help with my English writing, the class I am teaching, and providing answers to a broad range of question I ask. I’d also like to thank Lisa Robbins for working with me on the burdock project and all the help she kindly v provided. My gratitude also goes to Rachel Medina, who worked with me for the DIMBOA project. Caroline Gormley helped me with burdock project and Annelise Bay helped me with Moringa project. At last, I’d like to thank Dr. Wenshuang Xie for all the help he has kindly provided in the past five years. vi Vita 2012 …………………................................B.S. Applied Biological Science, Zhejiang University 2012 to present ……………………….……..Ph.D. Horticulture and Crop Science, The Ohio State University Fields of Study Major Field: Horticulture and Crop Science vii Table of Contents Abstract ............................................................................................................................... ii Acknowledgements ............................................................................................................. v Vita .................................................................................................................................... vii Table of Contents ............................................................................................................. viii List of Tables ................................................................................................................... xiv List of Figures ................................................................................................................... xv Chapter 1 Introduction ........................................................................................................ 1 Chemistry and biosynthesis of plant secondary metabolites (PSM) ............................... 2 Phenolic Compounds ................................................................................................... 2 Terpenoids and Steroids .............................................................................................. 4 Alkaloids...................................................................................................................... 5 Sites of PSM biosynthesis and storage ........................................................................ 6 The functions of PSM ..................................................................................................... 6 PSM as defense molecules .......................................................................................... 7 PSMs as signaling molecules .................................................................................... 12 Other functions of PSMs (abiotic stress, nitrogen-storage) ....................................... 13 viii Industrial applications of PSMs .................................................................................... 14 Medicinal application ................................................................................................ 14 Agricultural applications of PSMs ............................................................................ 18 Other industrial application ....................................................................................... 20 Summary of thesis chapters: Development of PSMs for industrial use ........................ 21 Medicinal applications of PSMs ................................................................................ 22 Agricultural applications of PSMs ............................................................................ 23 Model organisms for animal research ....................................................................... 24 Reference ....................................................................................................................... 26 Chapter 2 Anti-microbial activity and metabolite composition of burdock (Arctium lappa and Arctium minus) extracts ............................................................................................. 42 Introduction ................................................................................................................... 42 Materials and Methods .................................................................................................
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