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Abstract Condensed Tannin Characterization by Ft-Icr ABSTRACT CONDENSED TANNIN CHARACTERIZATION BY FT-ICR MALDI MASS SPECTROMETRY AND SEPARATION WITH SAW-TOOTH GRADIENT HPLC by Savanah Gail Reeves Condensed tannins (CT) are high molecular weight compounds, comprised of flavan-3-ol monomers stabilized by C-C interflavan bonds. They are found in plants and affect food astringency, protein availability, and biogeochemical cycles. Tannins are highly sorptive, making them difficult to analyze using existing methods. Recently, we developed methods using Fourier Transform Ion Cyclotron Resonance Matrix Assisted Laser Desorption/Ionization mass spectrometry (FT-ICR MALDI-MS) to obtain exact masses of polymer species. Using CT from Sorghum grain, we obtained spectra that exhibited peaks consistent with the (epi)catechin composition, previously proposed. However, the spectra also exhibited peaks that suggested the tannin contained ester groups. Using thiolysis, methanolysis, NMR, and Fourier Transform Infrared Spectroscopy (FTIR), we confirmed that the tannin does not contain ester groups. Instead, we propose that the MALDI matrix 2,5-dihydroxy benzoic acid forms adducts with the procyanidin that survive ionization and yield misleading MS peaks. To further characterize CT, we are developing reversed phase High Performance Liquid Chromatography (RP-HPLC) methods that separate polymers based on molecular weight. This is an improvement over previous methods that give a “hump” for most tannin extracts. Combining MALDI analysis with better HPLC methods will improve the potential to establish the roles of CT in diverse environments. CONDENSED TANNIN CHARACTERIZATION BY FT-ICR MALDI MASS SPECTROMETRY AND SEPARATION WITH SAW-TOOTH GRADIENT HPLC Thesis Submitted to the Faculty of Miami University in partial fulfillment of the requirements for the degree of Master of Science by Savanah Gail Reeves Miami University Oxford, Ohio 2020 Advisor: Dr. Ann E. Hagerman Reader: Dr. Neil D. Danielson Reader: Dr. Andrea N. Kravats Reader: Dr. Heeyoung Tai ©2020 Savanah Gail Reeves This thesis titled CONDENSED TANNIN CHARACTERIZATION BY FT-ICR MALDI MASS SPECTROMETRY AND SEPARATION WITH SAW-TOOTH GRADIENT HPLC by Savanah Gail Reeves has been approved for publication by College of Arts and Science and Department of Chemistry and Biochemistry ____________________________________________________ Dr. Ann E. Hagerman ______________________________________________________ Dr. Neil D. Danielson _______________________________________________________ Dr. Andrea N. Kravats _______________________________________________________ Dr. Heeyoung Tai Table of Contents Chapter 1: Introduction ………………………………………..……….………...… pg. 1 Chapter 2: Characterization of high molecular weight polyphenols by FT-ICR-MALDI-MS and HPLC …………………...…...…………….…………… pg. 11 Chapter 3: Improving RP-HPLC separation of condensed tannins ..….................… pg. 32 Chapter 4: Conclusion ………………………………………………………............ pg. 52 iii List of Tables Table 1. Thiolysis and HSQC NMR structural data for condensed tannin from Sorghum bicolor, Neptunia lutea, and cocoa. ….…………………...… pg. 25 Table 2. FT-ICR MALDI-MS data for condensed tannin from Sorghum bicolor, Neptunia lutea, and cocoa. ………………..…………..………… pg. 26 Table 3. FT-ICR ESI-MS/MS data of the peak at 864.69266 m/z for condensed tannin from Sorghum bicolor. …………………...…………….…… pg. 27 Table 4. Preliminary analysis of main peaks for Cocoa and Sorghum CT separated by three HPLC solvent methods. ……………………...…... pg. 48 Table 5. Thiolysis data of Sorghum CT HPLC fractions. ………………………….. pg. 49 iv List of Figures Figure 1. Condensed and hydrolyzable tannins. ………………………….……...... pg. 5 Figure 2. Diversity of condensed tannins. .………………………...………....……. pg. 6 Figure 3. FTIR spectra of EGCg, Neptunia lutea CT, catechin, cocoa CT, and Sorghum CT. ………..………………………………………..…….. pg. 22 Figure 4. Methanolysis HPLC Chromatogram. ………....……...……..………...…. pg. 23 Figure 5. 1H NMR spectra of DHB and DHB-Sorghum CT mixture. ....................... pg. 24 Figure 6. Chromatogram of cocoa CT separated by Method 1 with solvent gradient profile. ………………………………………….…………… pg. 41 Figure 7. Chromatogram of Sorghum CT separated by Method 1 with solvent gradient profile. ………………………………………………….....… pg. 42 Figure 8. Chromatogram of cocoa CT separated by Method 2 with solvent gradient profile. ……………………………………………….....…… pg. 43 Figure 9. Chromatogram of Sorghum CT separated by Method 2 with solvent gradient profile. ……………………………………………….....…… pg. 44 Figure 10. Chromatograms of reinjected fractions of Sorghum CT, analyzed by Method 2 with solvent gradient profile. …....………………........…… pg. 45 Figure 11. Chromatogram of cocoa CT separated by Method 3 with solvent gradient profile. …………………………………………….....……… pg. 46 Figure 12. Chromatogram of Sorghum CT separated by Method 3 with solvent gradient profile. …………………………………………….....……… pg. 47 v Dedication I dedicate my thesis work to my family and friends who helped me along the way. I am grateful for the support and encouragement of my loving parents. They always push me to achieve my very best. I want to thank my family, with a special thanks to Macie. Thank you to Brayden for always believing in me. I also want to thank my wonderful roommates. I also dedicate this work to my advisor, Dr. Ann E. Hagerman. Without her mentorship, none of this would have been possible. I am so appreciative for her guidance and her patience throughout this process. I’m so lucky to have had the opportunity to learn from her. vi Acknowledgements Dr. Ann E. Hagerman Dr. Arpad Somogyi Dr. Wayne Zeller Dr. Theresa Ramelot Dr. Neil D. Danielson Dr. Andrea N. Kravats Dr. Heeyoung Tai Dr. Andre J. Sommers Rosie Magro Mai Nguyen vii Chapter 1: Introduction As the fourth most abundant biochemical produced by plants, tannins play a large role in plant metabolism and interactions with other organisms1, 2. Tannins are a broad class of “water- soluble phenolic compounds having molecular weights between 500 and 3000 [Da ... with] the ability to precipitate alkaloids, gelatin and other proteins”3. The basic properties of tannins include antioxidant activity, protein binding, metal binding, and astringency. Tannins are highly bioactive compounds with diverse fates in diverse environments. When plants or fruits containing this material abscise, the tannins end up in the soil or water. In these environments, tannins contribute to plant, animal, and microbial metabolisms, as well as biogeochemical cycles1. When tannin-containing foods are eaten, tannins end up in the gut and digestive tract, contributing to human and animal metabolisms4. The microbiome plays a major role in the conversion of complex molecules, such as tannins, in both physiological systems and ecosystems5-7. Greater understanding of tannin structure may help to elucidate the functions of tannins in metabolism and biogeochemical cycles. There are two types of tannins: hydrolyzable and condensed tannins (Figure 1). Hydrolyzable tannins are derived from gallic acid; a core polyol such as glucose is esterified to gallic acid, with additional esterified or cross-linked galloyl groups (Figure 1b,c)8. These molecules are found in plants, including many that we consume, such as blackberries, pomegranates, and raspberries9-11. Hydrolyzable tannins are degraded by acidic or basic conditions, cleaving the ester bonds by hydrolysis or oxidation, into smaller phenolics11. They are also degraded by enzymes, such as phenol oxidase12 and tannase enzymes4, 13. While hydrolyzable tannin degradation has been thoroughly investigated, very little is known concerning the degradation of condensed tannins14. Condensed tannins (CTs, proanthocyanidins) are flavan-3-ol polymers with variations in hydroxylation patterns, cis- and trans-stereochemistry of C-ring substituents, interflavan bond connections (A or B type), mean degree of polymerization (mDP), and degree of esterification (Figure 1a, Figure 2)15. Condensed tannins, like hydrolyzable tannins, are present in plants including foods, such as grapes, persimmons, and Sorghum grain16-18. The C-C interflavan bonding between monomers of condensed tannin molecules makes them much less susceptible to degradation than the ester-linked hydrolyzable tannins. Therefore, the degradation of condensed 1 tannins, including the mechanism and products, is currently unclear. While the pathways for transformation of the flavan-3-ol subunits of CT to small molecule metabolites are well established19, more research needs to be performed to understand the initial steps of polymer decomposition. Degradation studies can afford greater understanding of the roles fulfilled by condensed tannins in diverse environments, and how those contributions affect and are affected by other environmental factors. In order to perform degradation studies, a large quantity of the target substrate is needed. For example, a soil microcosm experiment with one level of tannin amendment and all the appropriate controls requires 750 mg of tannin (McGivern, B and Wrighton, K personal communication). Obtaining a large amount of condensed tannin through extraction and purification techniques can be a difficult and time-consuming process. Our lab group, however, has optimized a technique that allows for purification of Sorghum CT with yields as high as 1.25 mg per gram of grain. Using this method, we routinely obtain 250 mg of tannin in just 4 days, making it easy and feasible to obtain enough CT for biological degradation studies. In order to trace the metabolic fate of tannin, it is necessary
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