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Isolation, Identification, and Biological Evaluation of Potential Flavor Modulatory Flavonoids from Eriodictyon californicum

Fletcher, Joshua Nehemiah
http://rave.ohiolink.edu/etdc/view?acc_num=osu1322496872

Abstract Details

2011, Doctor of Philosophy, Ohio State University, Pharmacy.
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 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.
A. Douglas Kinghorn, PhD (Advisor)
Werner Tjarks, PhD (Committee Co-Chair)
Esperanza Carcache de Blanco, PhD (Committee Member)
Steven Schwartz, PhD (Other)
177 p.
Food Science; Pharmacy Sciences
Eriodictyon californicum; taste; bitterness masking; sweetness enhancing; pharmacognosy

Recommended Citations

Citations

  • Fletcher, J. N. (2011). Isolation, Identification, and Biological Evaluation of Potential Flavor Modulatory Flavonoids from Eriodictyon californicum [Doctoral dissertation, Ohio State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=osu1322496872

    APA Style (7th edition)

  • Fletcher, Joshua. Isolation, Identification, and Biological Evaluation of Potential Flavor Modulatory Flavonoids from Eriodictyon californicum. 2011. Ohio State University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=osu1322496872.

    MLA Style (8th edition)

  • Fletcher, Joshua. "Isolation, Identification, and Biological Evaluation of Potential Flavor Modulatory Flavonoids from Eriodictyon californicum." Doctoral dissertation, Ohio State University, 2011. http://rave.ohiolink.edu/etdc/view?acc_num=osu1322496872

    Chicago Manual of Style (17th edition)

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This open access ETD is published by The Ohio State University and OhioLINK.