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Evaluating the Effects of Anthocyanin Structure and the Role of Metal Ions on the Blue Color Evolution of Anthocyanins in Varied Ph Environments

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Evaluating the Effects of Anthocyanin Structure and the Role of Metal Ions on the Blue Color Evolution of Anthocyanins in Varied Ph Environments Evaluating the Effects of Anthocyanin Structure and the Role of Metal Ions on the Blue Color Evolution of Anthocyanins in Varied pH Environments DISSERTATION Presented in Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School of The Ohio State University By Gregory T Sigurdson, B.S. Graduate Program in Food Science and Technology The Ohio State University 2016 Dissertation Committee: M. Mónica Giusti, Ph.D., Advisor Lynn Knipe, Ph.D. Luis Rodriguez-Saona, Ph.D. Christopher Simons, Ph.D. Copyrighted by Gregory Thomas Sigurdson 2016 Abstract Due to consumer demand and possible health concerns, the use of synthetic food colorants has been decreasing. Synthetic red and yellow colorants are most commonly used in the food industry; however they are considered easier to substitute with alternatives from nature due to their prevalence and various chemical natures. Alternatives for synthetic blue colorants are more limited due to low prevalence in nature, poor stability, or inability to match the color characteristics of the synthetic dyes. Anthocyanins are a class of natural pigments responsible for red, purple, and blue colors of edible produce with potential health benefits. In acidic conditions common to many food products, anthocyanins appear in red-purple structural forms limiting their use as blue colorants. However, self-association, co-pigmentation, and metal chelation have been suggested to expand their color expression to purple and blue in acidic pH. Metal ions displace hydrogen ions from B-ring hydroxyl groups, transforming red flavyliums to blue quinonoidal bases. The effects of the anthocyanin substitution pattern and role of various metal ions on their color evolution have not been fully elucidated in the wide pH range common to many foods. The objective of these studies was to replicate these naturally occurring reactions and evaluate the anthocyanin response to metal ions to expand the useful color and pH range of anthocyanins and to better understand the mechanisms of blue color expression. ii Acylated and nonacylated derivatives of cyanidin and delphinidin were combined with various metal ions (Mg2+, Al3+, Cr3+, Fe3+, and Ga3+) in factorial excesses to anthocyanin concentration (as large as 2000× [anthocyanin]) in pH 3-8. Phenolic acids were also evaluated as copigments on anthocyanin-metal chelates. The effects on anthocyanin color expression were evaluated by UV-Visible spectrophotometry (380-700 nm) and CIE-L*a*b* colorimetry (transmission, 10º observer angle, D65 illuminant). Anthocyanin responses to metal ion chelation were dependent on all factors tested. In all pH, anthocyanins exhibited bathochromic and hyperchromic shifts becoming more purple and blue. Largest bathochromic shifts occurred in pH 6, and largest hyperchromic shifts occurred in pH 5. The ratio of metal ion to anthocyanin necessary to induce the largest bathochromic shifts decreased as pH was increased indicating competition for the binding sites by hydrogen ions. Metal chelation resulted in larger bathochromic shifts on anthocyanins with more B-ring hydroxyl groups (delphinidin > cyanidin). Anthocyanins lacking acylation typically underwent much larger bathochromic shifts; however, the λmax of acylated anthocyanins with metals was larger in all cases, resulting in more blue color expression. Anthocyanins bearing diacylation expressed the most blue hues in the widest pH range followed by aromatically monoacylated anthocyanin derivatives. Hydroxycinnamic acid derivatives were shown to act as poor intermolecular copigments of anthocyanin-metal chelates when compared to their effects when covalently attached to the chromophore; they resulted in almost negligible changes to the color of the anthocyanin-chelates. iii Bivalent Mg2+ showed no obvious effect on anthocyanin color. Generally, bathochromic shifts on anthocyanin were greatest with more electron rich metal ions: Fe3+ ≈ Ga3+ > Al3+ > Cr3+. Metal chelation by anthocyanins resulted in blue and purple hues similar to currently used synthetic colorants in pH environments where these colors are not typically expressed, further indicating potential to act as alternatives. iv Dedication I dedicate the work of this dissertation to Grandpa, Geoffrey M. Sigurdson, who entered the realm of the bravest warriors before completion of it. v Acknowledgments I must first express my most sincere gratitude to my graduate advisor Dr. M. Mónica Giusti. I began my graduate program under slightly unusual circumstances, and she presented almost no reservation in allowing me to study under guidance. Through her hard work, research funding was secured that not only allowed me to investigate a topic that become very passionate to me but also provided me with ways to grow that many other graduate students do not have the opportunities to experience. Undoubtedly, Mónica is an expert in her field; and I was gifted the opportunity to absorb as much knowledge as I possibly could from her. The education I received from Mónica was not limited to anthocyanins or color chemistry; she was a great mentor in professional and personal growth, professional relationship development, and understanding the nuances of an academic career. Her passion for our field of study and encouragement throughout my graduate career was evident and often inspired me to strive to learn and undertake more. The gifts Mónica imparted to me will not be forgotten. I must also thank the members of my advisory committee Dr. Luis Rodriguez- Saona, Dr. Lynn Knipe, and Dr. Christopher Simons. I am grateful for the time they each have given me providing great advice and also conducting the various necessary components of a graduate level degree. The guidance they provided me is applicable in a variety of settings, and I will carry it with me. The challenges they gave me allowed me to progress in manners I otherwise would not have. Dr. Rodriguez-Saona was especially vi important in my academic growth, having been a professor for what I consider as some of the most formative and foundational courses in food science. He is not only a great advisor but also a great professor and instructor. I am also indebted to all my peers from the Giusti lab, some who left before me and some who are to follow. Each has played a unique in my education at The Ohio State University. From them I have learned a wide range of scientific knowledge; experienced unique cultures, foods, and languages; and gained several friends. I am especially grateful to Dr. Neda Ahmadiani, who not only took the time to train me to work in the lab but also to become an efficient lab manager. She was a great source of knowledge and is a great friend and mother. I must thank Alex Westfall who helped me care for the lab during her time here; she is an excellent friend and researcher and can always be counted on to keep things “Moo-ving” along. I am grateful for all my lab mates Jacob Farr, Allison Atnip, Fei Lao, Peipei Tang, Andrew Barry, Yucheng Zhou, Yingfang Li, Kai Zhang, Xiaoyi Zhu and Gonzalo Miyagusuku-Cruzado and hope the best for them all. I would like to thank Dr. Rebecca Robbins and Dr. Thomas Collins from Mars Chocolate. They have provided continuous support of my work and valuable advice and suggestions that not only improved the quality of my work but also extended my understanding and education. Through their efforts and Mars Chocolate NA, I was provided funding to earn my graduate degree. I am exceedingly grateful for the opportunities they provided me. I must also acknowledge my family whose pride and encouragement has helped me to continue the course of this program. It has been a long and challenging journey during which my family has been very understanding of my absences and neglect. I am eternally grateful for all the efforts and sacrifices my mother LaDonna Roys has done for me and for the achievement of this vii degree. I recall times in elementary school when my father Gregory A. Sigurdson would make the extra effort to help me with my homework with my advanced classes while suffering from lack of sleep from working two jobs. These memories have encouraged me to continue my studies even under the most stressful and tiresome of conditions. I can never thank my parents LaDonna Roys, Gregory Sigurdson and Lynn Sigurdson for their contributions and encouragement during this long journey. I have striven to bring pride to my family and will continue to do so. viii Vita January 1987 ..................................................Houston, TX May 2005 .......................................................Spencerville High School December 2011 ..............................................B.S. Food Science and Technology, The Ohio State University 2012 to present ..............................................Graduate Research Associate, Department of Food Science and Technology, The Ohio State University Publications Sigurdson, G. T.; Robbins, R. J.; Collins, T. M.; Giusti, M. M. (2016). Evaluating the Role of Metal Ions in the Bathochromic and Hyperchromic Responses of Cyanidin Derivatives in Acidic and Alkaline pH. Food Chemistry, 208, 1, 26-34. Sigurdson, G. T. & Giusti, M. M. (2014). Bathochromic and Hyperchromic Effects of Aluminum Salt Complexation by Anthocyanins from Edible Sources for Blue Color Development. Journal of Agricultural and Food Chemistry, 62, 6955–6965. ix Collins, T.; Robbins, R.; Giusti, M. M.; & Sigurdson, G. T. Colorant Compositions and Methods of Use Therein. Provisional patent application. Filed: June 30, 2015.
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