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Purple Corn Anthocyanins: Chemical Structure, Chemoprotective Activity and Structure/Function Relationships

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Purple Corn Anthocyanins: Chemical Structure, Chemoprotective Activity and Structure/Function Relationships PURPLE CORN ANTHOCYANINS: CHEMICAL STRUCTURE, CHEMOPROTECTIVE ACTIVITY AND STRUCTURE/FUNCTION RELATIONSHIPS DISSERTATION Presented in Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy the Graduate School of The Ohio State University By Pu Jing, M.S. * * * * * The Ohio State University 2006 Dissertation Committee: Professor Steven J. Schwartz, Adviser Approved by Assistant Professor M. Mónica Giusti, Co-Adviser Professor Valente Alvarez ___________________________________ Assistant Joshua A. Bomser Adviser ___________________________________ Co-Adviser Food Science and Nutrition Graduate Program © Copyright by PU JING 2006 ABSTRACT Interest in purple corn (Zea mays L.) as a natural colorant has increased because of their potential health benefits. This study evaluated an anthocyanin-based purple corn extract as a natural colorant and chemoprotective source as compared to other anthocyanin sources. The structure/function relationship between anthocyanins and relative biological activity were investigated. Purple corncob contained high monomeric anthocyanins concentration (290 to 1323 mg/100g DW) and acylated anthocyanins (35 to 54%). Obtaining a colorant from purple corn produces large amounts of a highly colored purple corn waste (PCW) with limited solubility. The limited solubility was associated with the complexation of anthocyanins with macromolecules (tannins and proteins) abundant in PCW. The purple corn pigment extraction procedure was modified to minimize waste production. Deionized water at 50 °C yielded high anthocyanin concentration with relatively low tannin and protein content. Application of a neutral protease during processing might decrease the level of the major protein (29KD) in purple corn and further reduce PCW. PCW was soluble in neutral environment and tested as a natural colorant for milk. PCW provided an attractive purple color (hue: 324-347°) to milk. This color was ii more stable in milk than in a pH6.8 buffer, suggesting that milk components protected anthocyanins and color in an accelerated model (70 ºC). Purple corn colorant showed higher inhibition of human colon carcinoma HT29 cell proliferation (GI50=~14µg/ml) than other six (chokeberry, bilberry, grape, purple carrot, radish, and elderberry) anthocyanin-rich extracts (ARE) (GI50 =31~130µg/ml). Anthocyanin-rich (2.29g/100g) PCW showed high antiproliferation (GI50 =21µg/ml), but lower than the purple corn colorant, suggesting that macromolecular complexes might trap monomeric anthocyanins reducing their bioavailability. An anthocyanin fraction separated from other phenolics in ARE played a major role on ARE’s chemoprotection. The interaction between anthocyanin and other ARE phenolics on chemoprotection was additive. Anthocyanin chemical structure affected chemoprotection: cyanidin 3- glucoside had higher inhibitory effect than pelargonidin 3-glucoside. Anthocyanin monoglucosylation showed a higher inhibitory activity than the corresponding 3,5- triglucoside. Effect of acylation on chemoprotection was dependant on the type of aglycone and acylating acid. More research is needed to better understand the impact of anthocyanin structure on chemoprotection. iii Dedicated to my mom and Yan iv ACKNOWLEDGMENTS My first, and most earnest, acknowledgment must go to my advisor Dr M. Monica Giusti. Your expertise, diligence, patience, encouragement, enthusiasm and open-mindedness raised me up to this mountain and benefited me throughout my life. Thanks are given to my dissertation committee: Dr Steven J. Schwartz, Dr Joshua A. Bomser and Dr Valente Alvarez for providing me with your invaluable academic offerings, which solidly grounded me with the completion of my PhD education. Thanks particularly to Dr Steven J. Schwartz, Dr Joshua A. Bomser, and Dr Luis E. Rodriguez-Saona for providing convenient access to experimental facilities and continually supporting to my research and study. None of this work would have been possible without you. Tons of thanks to Dr Magnuson, her lab group and other friends in Maryland. I still remember the simplest but the best farewell party in my life. I am grateful to all my lab colleagues for your numerous help and support during my study and research. Thanks to my friends here. With you, life could not be sweeter! We are also grateful to the USDA NRI competitive grants program and the Alumni Grants for Graduate Research and Scholarship (AGGRS) from The Ohio State v University for providing financial support. We thank Artemis International, Inc., Polyphenolics, Inc., RFI Ingredients, Globenatural International S.A., Overseal Foods Ltd for their providing samples. vi VITA May 27, 1972………… Born – Sichuan, China 1996……………………B.E. Food Science and Engineering, Sichuan Institute of Light Industry and Chemistry Technology 1996 - 1998 ……………Quality supervisor Sichuan King Food Co., Ltd. Chengdu, China 2001……………………M.S. Food Science, Southwest Agricultural University 2001…………………… Adjunct Lecturer Fujian Agricultural University, Fujian, China 2002 - 2004…………….Graduate Research Assistant University of Maryland, College park, Maryland 2004 – Present …………Graduate Research and Teaching Assistant The Ohio State University PUBLICATIONS Research Publication 1. Wyzgoski, F.J., Rinaldi, P.L., Reese, R.N., Scheerens, J.C., Miller, A.R., Bishop, B.L., Giusti, M.M., Bomser, J.L., Ozgen, M., Tulio Jr., A.Z. and Jing, P. (2006). Using high field cryoprobe NMR experiments and multivariate analysis to vii identify bioactive components in black raspberries. American Chemical Society National Meeting. 2. Jing, P., and Giusti, M. M. (2005). Characterization of Anthocyanin-Rich Waste from Purple Corncobs (Zea mays L.) and Its Application to Color Milk. J Agric Food Chem 53, 8775-8781. 3. Jing, P., Ding, X.W., and Su, Y. (2000). Scavenging effect of extract of citrus peel on •OH. Journal of Southwest Agricultural University. 22, 416-418. 4. Jing, P. and Su, Y. (2000). Development of sports drinks. Beverage Industry, China, 3, 7-9. 5. Jing, P. (1999). Development of functional food in China. Chinese Animal Product and Food, 6, 233-234. 6. Xiang Y.F. Jing, P., and Chen, M. (1996). Improvement of Bennett Test. Studies in Higher Education, 7, 61-62. 7. Xiang, Y.F., Jing, P., and Liu, D.Y. 1996. Study on microencapsulation process of Zanthoxylum oleoresin. Journal of Sichuan University (Natural Science Edition), 33, 760-764. FIELD OF STUDY Major Field: Food Science and Nutrition viii TABLE OF CONTENTS Page Abstract……………………………………………………………………………….ii Dedication…………………………………………………………………………….iv Acknowledgments…………………………………………………………………...v Vita…………………………………………………………………………………vii List of Tables……………………………………………………………………....xviii List of Figures………………………………………………………………………xx List of Abbreviations….............................................................................................xxiii Chapters: 1. Introduction………………………....……………….…………………………1 2. Literature review………….…………………………………………………....5 2.1. Purple corn (Zea mays L.)…………………………………………………….5 2.2. Anthocyanin distribution in edible plants………………………………….6 2.3. Anthocyanin chemistry…………………………………………...………….9 2.3.1. Structure and chemistry……………………………………………9 2.3.2. Anthocyanin stability……………………………………………18 2.3.3. The influence of pH………………………………………………19 2.3.4. Acylation…………………………………………………………21 2.3.5. Copigmentation……………………………………………………23 2.3.6. Anthocyanins degradation kinetics………………………………..24 2.4. Extraction of Anthocyanins………………………………………………….24 2.5. Health benefits of anthocyanin-rich commodities…………………………26 ix 2.5.1. Epidemiological study……...………………………………………26 2.5.2. Antioxidants……..… …………………………………………….28 2.5.3. Cancer chemoprotective studies……………………………………33 2.5.3.1. Antioxidative activity……………………………………33 2.5.3.2. Detoxification activity……………………………………35 2.5.3.3. Antiproliferation and apoptosis induction……………….…35 2.5.3.4. Anti-angiogenic activity……………………………....……43 2.5.3.5. Animal studies……………………………………….……..44 2.5.4. Cardiovasular Diseases ……………………………………………45 2.5.5. Anti-inflammation…………………………………………………48 2.5.6. Antimutation………………………………………………………49 2.5.7. Obesity…………………………………………………………….50 2.5.8. Immune System……………………………………………………50 2.5.9. Eye Health………………………………………………………..51 2.5.10. Neurological Function…………………………………………..52 2.6. Bioavailability……………………………………………………………….52 2.7. Anthocyanin-rich commodities and colorectal cancer……………………….56 2.8. Health benefits of anthocyanin-rich colorant of purple corn………………60 2.9. Toxicology…………………………………………………………………61 2.10. Potential application………………………………………………………62 2.10.1. Natural colorants…………………………………………………62 2.10.2. Value-added functional food…….………..………………………63 2.11. References…………………………………………………………………..65 3. Anthocyanins in purple corncob (Zea mays L.)………………….……...…..91 3.1. Abstract………………………………………………………………………91 3.2. Introduction…………………………………………………………………92 3.3. Materials and methods……………………………………………………….94 x 3.3.1. Material and reagents…………………………………………….94 3.3.2. Anthocyanin extraction…………………………………………….95 3.3.3. Monomeric anthocyanins and polymeric anthocyanins………….95 3.3.4. Total phenolics……………………………………………………..96 3.3.5. Analytical chromatography………………………………………..96 3.3.6. LC/MS/MS ………………………………………………………97 3.3.7. Statistical design and analysis……………………………………97 3.4. Results and discussion……………………………………………………….98 3.4.1. Anthocyanins and total phenolics in purple corncobs……………98 3.4.2. Anthocyanin profiles in purple corns……………………………102 3.5. Conclusions…………………………………………………………………105 3.6. Acknowledgments…………………………………………………………105 3.7. References…………………………………………………………………106
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