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Evaluating the Chemical Diversity and Biological Activity of Plant Extracts for Commercialization

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Evaluating the Chemical Diversity and Biological Activity of Plant Extracts for Commercialization Evaluating the chemical diversity and biological activity of plant extracts for commercialization A DISSERTATION SUBMITTED TO THE FACULTY OF UNIVERSITY OF MINNESOTA BY Amanda C. Martin IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY Adviser: Dr. Adrian D. Hegeman, Co-adviser: Dr. Donald L. Wyse November 2014 © Amanda C. Martin 2014 All Rights Reserved Acknowledgements Many people helped me in the process of earning my PhD. First, thank you to my advisors Dr. Adrian Hegeman and Dr. Donald Wyse and to my committee members Dr. Florence Gleason, Dr. Jerry Cohen, and Dr. Chengguo Xing for their support and encouragement to apply myself in the field and lab – and to apply for fellowship opportunities. Thank you to Kevin Betts, Marnie Plunkett, and all of the Wyse group undergraduates for their endless help in the field. Particular thanks to Marnie for sticking with me for three years as an undergraduate assistant. Thank you to Dr. Alison Pawlus for taking me under her wing and teaching me to ins and outs of discovery in the lab and for being a great friend throughout my ups and downs. Thank you to Dr. Cindy Angerhofer, Tim Kapsner, and the Botanicals Research team at Aveda for believing in an supporting this project. Thank you to Dr. Dana Freund for her constant stream of pep- talks that fueled the last year and a half of graduate school for me. Thank you to Ed Johnston for graciously opening up his home to me in Hawaii and never giving up on the kava study. Thank you to Gail Kalli for her endless administrative and strategic support and for being a friend whose door was always open to me and all PBS graduate students. Thank you to Lisa Wiley and Linda Hermanson for being there for me during the more personally challenging times in graduate school. Thank you to Noro Andriamanalina and the Community of Scholars Program for bringing together a tight knit scholarly community of people who might otherwise feel hopelessly out of place. Thank you to Northland College for giving me the space to become the person I was meant to be and to the professors who gave me the tools and drive to achieve my goals including Drs. Young Kim, Rick Dowd, Brian-Nowak-Thompson, and David Saetre. Thank you to all of my friends for reminding me about life outside of the lab including Kelsey Imbertson, Rachel Anderson, and Karen Anderson. Thank you to my parents Debra and Leo Martin Jr. for creating a strong and stable foundation for me and my brother, Victor, and sister, Sarah. Finally, thank you to my amazingly supportive and loving husband Colin. i Dedication This thesis is dedicated to my grandparents, Carol and Berenice Handy and Mildred and Leo Martin Sr. for their eternal guidance and inspiration. ii Abstract Perennial plants are a manageable natural resource with the potential to provide both highly valuable biologically active chemicals and ecosystem services. Ecosystem services include various benefits that are provided by an ecosystem such as food, fuel, recreation, as well as water, air, and land quality for society. Biologically active chemicals from plants have a long history of use by humans in botanical medicines and pharmaceuticals, food and dietary supplements, agricultural inputs, and home and personal care products. There are different strategies that can be used to incorporate plants into an economic and ecosystem service role. Method development and application studies were used to facilitate use of plant derived bioactive compounds for commercial use. Methodological studies, using the technique of metabolic fingerprinting, resulted in the determination of extraction conditions that maximize chemical diversity and yield. Maximum chemical diversity in a plant extract was most efficiently approached if solvent partitioning was performed on an extract made with 70 percent ethanol. Additionally, strategies to integrate extract chemical analysis with information regarding extract quality, such as cytotoxicity measurements, were developed and used to evaluate commercial kava samples obtained from multiple sources. These approaches were then applied to two different perennial plant species ( Comptonia peregrina , and Glycyrrhiza lepidota ) with the aim of developing their commercial value based on their extractable chemical composition. These studies resulted in the isolation of two small molecules from C. peregrina with strong antimicrobial activity and the identification of two G. lepidota populations with the potential to be developed into a cultivar with optimal characteristics for the cultivation of biologically active compounds. iii Table of Contents List of Tables……………………………………………………………………..….……v List of Figures………………………………………………………………………....….vi List of Abbreviations……………………………………………………………………..ix Chapter 1………………………………………………………………………………pg. 1 Introduction Chapter 2………………………………………………………………….………...…pg. 6 Evaluating solvent extraction systems using metabolomics approaches Chapter 3…………………………………………………………………………..…pg. 36 Measuring the chemical and cytotoxic variability of commercially available kava ( Piper methysticum G. Forster) Chapter 4…………………………………………………………………………..…pg. 60 Antimicrobial constituents of Comptonia peregrina (L.) J.M. Coulter (Sweet Fern) Chapter 5…………………………………………………………………………..…pg. 75 Developing American licorice ( Glycyrrhiza lepidota (Nutt.) Pursh) germplasm for the cultivation of biologically active compounds Conclusions……………………………………………………………………........pg. 111 Bibliography………………………………………………………………………..pg. 112 Appendix A……………………………………………………………………....…pg. 128 Spectral data for compounds isolated from C. peregrina Appendix B………………………………………………………………………….pg.141 Compounds found in plants of the Glycyrrhiza (licorice) genus Appendix C………………………………………………………...……………….pg. 169 Minnesota Plant Collection Permits iv List of Tables Chapter 3 Table 1. Kava exports from Fiji, Tonga and Vanuatu: 2008 through 2013. (pg. 47) Table 2. Commercial kava sources. (pg. 50) Table 3. Average concentration (ppm) of compounds from dry powder commercial kava sources. (pg. 52) Table 4. Average concentration (ppm) of compounds from liquid commercial kava sources. (pg. 54) Chapter 4 Table 1. Antimicrobial activity of methanolic Comptonia peregrina extract partitions, fractions and isolated compounds. (pg. 73) Chapter 5 Table 1. Minnesota Glycyrrhiza lepidota seed collection locations (pg. 102) Appendix B Table 1. Compounds found in plants of the Glycyrrhiza (licorice) genus (pg. 142) v List of Figures Chapter 2 Figure 1. Schematic of workflows for A) parallel single-solvent extractions and B) extraction partitioning. (pg. 25) Figure 2. Comparison of extraction efficiency for extracts prepared from 8 parallel single-solvent extractions. (pg. 26) Figure 3. Comparison of extraction efficiency for extracts prepared from parallel single-solvent extractions. (pg. 27) Figure 4. Scatterplots showing the distribution of features detected from metabolic fingerprints of extracts. (pg. 28) Figure 5. Representative principal components analysis of L. salicaria parallel single-solvent extractions. (pg. 29) Figure 6. Comparison of extraction efficiency via chemical complexity for combinations of two and three parallel single-solvent extractions. (pg. 30) Figure 7. Comparison of extraction efficiency via chemical complexity of combinations of three parallel single-solvent extractions and extraction partitions of R. typhina leaf, berry, and stem tissue. (pg. 31) Figure 8. Photographs of representative extractions. (pg. 32) Figure 9. Representative principal components analysis of R. typhina berry extraction partitions and hexanes single-solvent extraction. (pg. 33) Figure 10. Representative principal components analysis of R. typhina berry extraction partitions and dichloromethane single-solvent extraction. (pg. 34) Figure 11. Representative principal components analysis of R. typhina berry extraction partitions and 70% ethanol, methanol, and water single- solvent extraction. (pg. 35) Chapter 3 Figure 1. Histograms showing the distribution of concentrations of compounds found in commercial kava preparations. (pg. 48) vi Figure 2. Comparison of relative cell viability to flavokawain (FLK) A and B concentrations. (pg. 49) Figure 3. Principal components analysis (PCA) of commercial kava preparations. (pg. 56) Figure 4. Principal components analysis (PCA) of commercial kava preparations. (pg. 57) Figure 5. Correlation between relative cell viability and Flavokawain A concentration. (pg. 58) Figure 6. Correlation between relative cell viability and Flavokawain B concentration. (pg. 59) Chapter 4 Figure 1. Solvent extraction scheme used for the aerial tissues of Comptonia peregrina . (pg. 72) Figure 2. Structures of the compounds isolated from C. peregrina above ground parts. 1) galangin, 2) pinocembrin, and 3) pinosylvin monomethyl ether. (pg. 74) Chapter 5 Figure 1. Compounds isolated from plants belonging to the genus Glycyrrhiza . (pg. 101) Figure 2. Three-year survival rate for nine Minnesota native populations of Glycyrrhiza lepidota . (pg. 103) Figure 3. Total above and below ground biomass for six Minnesota native populations of Glycyrrhiza lepidota . (pg. 104) Figure 4. Average number of inflorescences and seed pods for six Minnesota native populations of Glycyrrhiza lepidota . (pg. 105) Figure 5. Average seed traits for six Minnesota native populations of Glycyrrhiza lepidota . (pg. 106) Figure 6. Average percent seed viability for six Minnesota native populations of Glycyrrhiza lepidota . (pg. 107) vii Figure 7. Average antimicrobial
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