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View This Dissertation Isolation, Identification, and Biological Evaluation of Potential Flavor Modulatory Flavonoids from Eriodictyon californicum Dissertation Presented in Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy in the Graduate School of The Ohio State University By Joshua Nehemiah Fletcher Graduate Program in Pharmacy The Ohio State University 2011 Dissertation Committee: A. Douglas Kinghorn, Advisor Esperanza J. Carcache de Blanco Steven. J. Schwartz Werner Tjarks Copyright by Joshua Nehemiah Fletcher 2011 Abstract The avoidance of bitter-tasting substances and a preference for sweet-tasting substances have deep roots in the evolutionary history of mankind. With the advent of agriculture, and more recent advancements in food production the necessity of these preferences has diminished somewhat. In fact, the evolutionary biases of humanity can be considered responsible for certain heath problems in the modern world. It is against this backdrop that the present study of Eriodictyon californicum Decne. (Hydrophyllaceae) for bitterness-masking and sweetness-enhancing activity, in collaboration with Givaudan Flavors Corporation, Cincinnati, OH, was commenced. In this dissertation study, ten flavonoids were isolated from E. californicum, with two of these having been publisheed previously presented without defined stereochemistry and another with incomplete spectroscopic and physical data to confirm its structure. Additionally, this is the first time that the natural absolute configuration of flavanones from E. californicum has been resolved. Four of the isolated compounds and an additional purchased compound were evaluated for sweetness-enhancing activity in a chimeric cell-based assay. All ten compounds isolated were tested for bitterness-masking activity in a cell-based assay employing the bitterness receptor hTAS2R31. The use of cell-based assays for taste research is a very recent development in the field, with access ii to these techniques generally exclusive to the industrial sector due to the patenting of the taste receptors. It was determined that hesperetin (44) and sakuranetin (72) from E. californicum and the purchased compound, 3,2'-dihydroxy-4,4',6'-trimethoxychalcone (105), are potential sweetness-enhancing compounds, due to their in vitro activity in the sweetness- enhancing assay employed. The results of the in vitro bitterness-masking assay showed the flavone, jaceosidin (66), and the flavanones sakuranetin (72) and 6- methoxysakuranetin (98) to be potential bitterness-masking components of the leaves of E. californicum. When taken together, these results strongly indicate that flavonoids with different A-ring functionalities may have a role in potential in taste modulation applications. iii Dedication This dissertation is dedicated to my family, and all those who aided me along the way. iv Acknowledgments I would like to extend a heartfelt thanks to my advisor Dr. A. Douglas Kinghorn, for giving me the opportunity to conduct research in his laboratory. Without his support and influence this work would not have been possible. I would like to thank my dissertation defense committee Drs. Esperanza J. Carcache de Blanco, Steven. J. Schwartz, and Werner Tjarks for sacrificing their valuable time in order to review this dissertation. I wish to thank the members of the Kinghorn laboratory that I have had the honor of studying with during my tenure as student in the College of Pharmacy. I wish to extend special thanks to Drs. Marcy J. Balunas, William P. Jones, and Young-Won Chin, who all served as mentors in my growth as a researcher. I would also like to especially thank Mr. Mark Bahar for being a constant friend. I would like to thank our collaborators at the Givaudan Flavors Corporation, Cincinnati, OH for funding this dissertation project and for conducting the sweetness- enhancing and bitterness-masking cell-based assays used in this work. I am especially grateful to Drs. Zhonghua Jia and Jay P. Slack for their mentorship and efforts in support of this project. v I am grateful to Dr. Karl A. Werbovetz for initially suggesting that I investigate Eriodictyon californicum, and Dr. John M. Cassady for donating the plant material used in this research. Dr. Richard Spjut, World Botanical Associates, Laurel, MD, is acknowledged for collecting this plant material. I would like to thank Mr. J. Fowble for his service in maintaining many of the analytical instruments used at the College of Pharmacy, and the Central Campus Instrument Center for the use of its mass spectrometry facilities. I am extremely grateful for the financial support that I was given as a graduate student through the Chemistry and Biology Interface Training Program (NIH) (2003- 2005), the Raymond W. Doskotch Fellowship (2009-2010), the Jack L. Beal Award (2010), and as a Teaching Assistant (2005-2008, 2009-2010) and a Research Assistant (2008-2009, 2011). I am especially thankful to the Givaudan Flavors Corporation for funding me as a Research Assistant (2011). I would like to sincerely thank all who contributed to my education; from my grade school teachers at Steubenville City Schools, to each professor that I have learned from at The Ohio State University. I would like to thank my friends and family for their loving support throughout my life. I especially thank my mother, Linda (a key collaborator on many successful science fair projects), my father, Herbert, my siblings, Christopher and Nicholas, and my wife, Gwyndolyn. Lastly, I would like to thank the Creator, for the wonderful world in which I have the pleasure of conducting research. vi Vita 1999. Steubenville High School 2003. B.S. Arts & Sciences (Chemistry), The Ohio State University 2003-2011. Graduate Student, College of Pharmacy, The Ohio State University Awards and Honors Jack L. Beal. Award, The Ohio State University, College of Pharmacy, 2010. Raymond W. Doskotch Graduate Student Fellowship, The Ohio State University, College of Pharmacy, 2009-2010. Chemistry-Biology Interface Training Program Fellowship, National Institutes of Health, 2003-2005. Meyers Math and Physical Sciences Scholarship, The Ohio State University, College of Arts and Physical Sciences 2001-2003. Trustees Scholarship, The Ohio State University, 1999-2003. Office of Minority Affairs Excellence Scholarship, The Ohio State University, 1999- 2003. Ella Stafford Scholarship, Steubenville High School, 1999. vii Poster Presentations Fletcher J. N., Kinghorn, A. D., Slack, J. P., Odley, A., Jia Z. Evaluation of Potential Bitterness-Masking Flavonoids from Eriodictyon californicum. Presented at the 51st Annual American Society of Pharmacognosy Meeting, St. Petersburg, FL, July 2010. Fletcher J. N., Kinghorn A. D., Slack J. P., Jia Z. Evaluation of Flavonoids from Eriodictyon californicum as Potential Taste Modifiers in a Cell-Based Assay. Presented at the 50th Annual American Society of Pharmacognosy Meeting, Honolulu, HI, June 2009. Fletcher J. N.; Chin, Y.-W.; Bahar M.; Werbovetz, K. A.; Kinghorn, A. D. Antileishmanial Activity of Some Naturally Occurring Phenolics. Presented at the 40th Annual Central Regional Meeting of the American Chemical Society, Columbus, OH, June 2008. Fletcher, J. N.; Doskotch, R. W.; Werbovetz, K. A.; Kinghorn, A. D. Anti-leishmanial Bioactivity-Guided Fractionation of Ficus elastica. Presented at the 48th Annual American Society of Pharmacognosy Meeting, Portland, ME, July 2007. Fletcher J. N.; Bahar M.; Werbovetz K. A.; Kinghorn, A. D. Antileishmanial Activity of Some Naturally Occurring Flavonoids. Presented at the 39th Annual Mid- Atlantic Graduate Student Symposium in Medicinal Chemistry, Columbus, OH, June 2006. viii Publications Bahar M.; Deng Y.; Fletcher, J. N.; Kinghorn A. D. Plant-Derived Natural Products in Drug Discovery and Development: an Overview. In Selected Topics in the Chemistry of Natural Products, Ikan, R., Ed.; World Scientific Publications: Singapore, 2008, pp 11-48. Kinghorn A. D.; Pan L.; Fletcher J. N.; Chai, H. The relevance of higher plants in lead compound discovery programs. J. Nat. Prod. 2011, 74, 1539–1555. Fletcher, J. N.; Kinghorn, A. D.; Slack, J. P.; McCluskey, T. S.; Odley, A.; Jia Z. In vitro evaluation of flavonoids from Eriodictyon californicum for antagonist activity against the bitterness receptor hTAS2R31. Published on the Web Nov. 8, 2011 in J. Agric. Food Chem. DOI: 10.1021/jf204359q Fields of Study Major Field: Pharmacy ix Table of Contents Abstract . ii Dedication . iv Acknowledgments . v Vita . vii Table of Contents . x List of Tables . xv List of Figures . xvi List of Abbreviations . xxi Chapter 1: Overview of the Field of Taste Perception and Its Relevance to Health. 1 A. Overview of the Biological Role and Mechanism of Taste Perception. .1 1. Evolutionary Basis for Taste . 1 2. Current Debates in the Field of Taste . 2 3. Recent Scientific Advances in the Field of Taste Perception. 5 3.1 Elucidation of the bitter and sweet signal transduction pathways. 5 3.2 Discovery of sweet taste and umami taste receptors. 9 3.3 Discovery of bitter receptors. 11 B. Negative Health Effects Associated with Taste Preferences . 12 x 1. Bitterness and "functional foods". 13 1.1. Examples of “functional foods” containing bitter components – soy. 17 1.2. Examples of "functional foods" containing bitter components – citrus juices. 18 1.3. Examples of "functional foods" containing bitter components – cruciferous vegetables . 19 1.4. Examples of "functional foods" containing bitter components – cocoa . 21 2. The Search for Healthy Sugar Substitutes
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