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Metabolism and Anti-Inflammatory Activity of Anthocyanins in Human Oral Cavity

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Metabolism and Anti-Inflammatory Activity of Anthocyanins in Human Oral Cavity Metabolism and Anti-inflammatory Activity of Anthocyanins in Human Oral Cavity DISSERTATION Presented in Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School of The Ohio State University By Kom Kamonpatana, M.Sc. Graduate Program in The Ohio State University Nutrition Program The Ohio State University 2012 Dissertation Committee: Dr. Mark L. Failla, Advisor Dr. M. Mónica Giusti, Co-Advisor Dr. Purnima S. Kumar Dr. Steven J. Schwartz © Copyrighted by Kom Kamonpatana 2012 All rights reserved ABSTRACT Anthocyanins (ACN), natural pigment flavonoids, exhibit chemopreventive, chemotherapeutic, and anti-inflammatory activities in the oral cavity. ACN have recently been included into products for the promotion of oral health. However, it is unclear which ACN-rich foods could be most efficacious. Since fruits and vegetables contain unique mixtures of ACNs, an understanding of effect of ACN structure on metabolism, bioavailability, and bioactivity is needed for providing sound dietary recommendations and development of products containing ACN for promotion of oral health. ACN extracts from blueberry, chokeberry, black raspberry, red grape, and strawberry were incubated ex vivo for 60 min in human saliva (Chapter 2). Degradation of chokeberry ACN was primarily enzymatic and mediated by bacteria. Glycosides of delphinidin (Dp) and petunidin (Pt) were more susceptible to chemical degradation than those of cyanidin (Cy), pelargonidin (Pg), peonidin (Pn) and malvidin (Mv) in both intact and artificial saliva. Stability of di- and tri-saccharide conjugates of anthocyanidins was slightly greater than that of mono-saccharide derivatives. The ex vivo degradation was significantly decreased in saliva obtained after volunteers rinsed their mouths with anti- bacterial chlorhexidine. I next examined whether the ex vivo finds could be recapitulated in vivo by having subject retain for 5 minutes either chokeberry or red grape juice in their mouths (Chapter 3). Retained juice, oral washings and buccal scrapings were collected and analyzed for stability of ACN in the oral cavity, binding to buccal mucus and uptake into buccal cells. Cy-3-glucoside preferentially accumulated with the buccal cells compared to other Cy glycosides. Anti-bacterial treatment resulted in greater stability of ACN in retained juice. ii Loss of Dp glucosides exceeded that of Pt, Cy, Pn and Mv glucosides during oral retention of red grape juice. Lesser relative amounts of Dp and Pt glucosides were associated with mucus and buccal cells than Cy, Pn and Mv glucosides, suggesting their instability and limited accessibility to the oral epithelium. I investigated inhibitory activity of ACN mixtures on pro-inflammatory cytokine secretion by oral epithelial cells. ACN extracts from black raspberry, blueberry, chokeberry, red grape, strawberry, and hibiscus were incubated with cells prior to, simultaneously or after addition of IL-1β followed by measurement of IL-8 secretion (Chapter 4). Chokeberry extract reduced IL-1β induced IL-8 secretion by SCC-25 in a dose response manner. The efficacy of inhibitory activity depended on both the ACN composition of the extract (Pg-rich (strawberry) > five anthocyanidins (red grape) > Cy- rich (chokeberry and black raspberry) ≈ Cy-Dp disaccharide (hibiscus) extracts) and the type of cell (effect on SCC-25 cancer cells > OKF-6/TERT-2 non-cancer cells). Pre- conditioning medium, by incubating with extracts for 24 h to allow degradation of approximately 90% of ACN, minimally affected inhibitory activity in SSC-25 cultures, demonstrating that degradation products contributed to the bioactivity. These data demonstrated that the natural ACN composition determines stability, bioaccessibility to the buccal epithelium, and anti-inflammatory activity with oral epithelium. The effects of ACN structure and their degradation products merit further consideration for the development of sound dietary recommendations and/or formulation of ACN-rich products for the promotion of oral health. iii In dedication to my supporting family, my ancestors, and scientists before me. iv ACKNOWLEDGMENTS First and foremost, I would like to extend my sincere gratitude to Dr. Mark L. Failla for providing great opportunity to work with him and his collaborators. His visionary leadership, friendship, criticisms, patience and positive challenges throughout my doctoral endeavor will not be forgoten. I am thankful to Dr. Chureeporn Chitchumroonchokchai for introducing me to nutrition science, her patience and continued supports. I sincerely thank to members of Failla’s laboratory, i.e., Dr. Sagar Thakkar; Ms. Fabiola Gutierrez Orozco, Ms. Emily Carson, and Mr. Emiliano Melgar- Bermudez who always provided their hands in time of need. I am in debt to Dr. M. Mónica Giusti for her willingness to teach me sound conceptual and technical skills required for the analysis of anthocyanins. I am thankful to members of her lab including Ms. M. Fernanda Polit Arcos, Dr. Taylor C. Wallace, Ms. Neda Ahmadiani, and Ms. Allison Atnip who provided initial training and subsequent assistance with the purification and analysis of HPLC-MS. I am also in debt to Dr. Purnima S. Kumar and members of her research team, i.e., Ms. Maria MorenoCruz, Dr. Samir Shah, Mr. Matthew Mason, Ms. Megan Fellows, and Ms. Monica Bonnin who literally opened the door for clinical studies and provided training with the culture of oral epithelial cells. Their spirit of ‘get things done’ will be remembered. I am grateful to Dr. Steven J. Schwartz and his colleagues Dr. Ken Reidl and Dr. Rachel Kopec for their support for the screening of degradation products of chokeberry anthocyanins by HPLC-TOF-MS in the Nutrient and Phytochemical Analytic Shared Resource Core of the OSU Comprehensive Cancer Center (NPASR). Assistance from Dr. Joseph Scheerens of the OARDC in providing black raspberries from Maurer’s farm will be remembered. I also thank Artemis International v and Enzyme Development Corp. for the gift of chokeberry samples and food-grade pectinase, respectively. I would like to thank all participants of clinical studies who show willingness and provide time to take part in 3 years of studies. I thank collegues in the Ohio State University Nutrition Program (OSUN), i.e., Ms. Kara Kliewer, Dr. Amber Simmons, Ms. Jia Yu Ke, Dr. Rumana Yasmeen, my friends in Food Science & Technology department, and the Thai Student Association of the Ohio State University who were always willing to provide their thoughts about for my data, stimulating intellectual discussion, laughter and friendship. I am deeply thankful to financial supports and awards for these studies: The College of Education and Human Ecology (EHE) dissertation year fellowship; The Ohio Agricultural Research and Development Center (OARDC); the OARDC Graduate Research grant, OSUN; the Leta Gigax Duhamel Scholarship; the Food Innovation Center (FIC) of OSU; and research competition awards from Institute of Food Technologist (IFT). Finally and most importantly, I thank my family for their love, support and encouragement throughout my graduate endeavor. My father Mr. Angkorn and mother Prof. Maneewan Kamonpatana who have provided continual inspirations and supports; my wife Dr. Pitiya and daughter Sirin Kamonpatana for their supports, encouragements and being the most important reason for completion of the degree; my in-laws Mr. Mangkorn and Ms Ranee Namwonk who came to welcome Sirin to family; and my siblings, Mr. Kor and Ms. Kamonrat Kamonpatana, who have provided unconditioned support to our family in Thailand in my absence. vi VITA 1973…………………………………………………………...…Born, Bangkok, Thailand 1993……………………...B.Sc. (Food Technology), Chulalongkorn University, Thailand 1997…………………..…M.Sc. (Food Technology), Chulalongkorn University, Thailand 1998-2005…….……………………………….…Mars Petcare, Thailand and Asia Pacific 2005-2006……………………………..…Charoen Pokphand Foods PCL (CPF), Thailand 2006-2008………………………………………………..…Mead Johnson Nutrition, Asia 2008-2012…………………...OSU Nutrition Program, The Ohio State University, U.S.A. PUBLICATION Research Publication 1. Kamonpatana, K.; Giusti, M.M.; Chitchumroonchokchai, C.; MorenoCruz, M.; Riedl, K.M.; Kumar, P.S.; Failla, M.L. (2012). Susceptibility of anthocyanins to ex vivo degradation in human saliva. Food Chemistry. 135, 738-747. Abstracts 2. Kamonpatana, K; Moreno Cruz, M; Kumar, P; Giusti, MM; Failla, ML. (2012). Metabolism and Uptake of Anthocyanins in Human Oral Cavity. #084-28. 2012 IFT annual meeting, Las Vegas, Nevada, U.S.A. (Second place, Nutrition division, graduate student research competition). 3. Kamonpatana, K; Moreno Cruz, M; Kumar, P; Giusti, MM; Failla, ML. (2012). Metabolism and epithelial cell uptake of chokeberry and grape anthocyanins in human oral cavity. Russell Klein Memorial Nutrition Research Symposium, The Ohio State University, Columbus, Ohio, U.S.A. 4. Kamonpatana, K; Moreno Cruz, M; Kumar, P; Giusti, MM; Failla, ML. (2011). Metabolism and uptake of berry and grape anthocyanins in human oral cavity. 2011 EHE Student Research Forum, Columbus, Ohio, U.S.A. 5. Giusti, MM; Kamonpatana, K; Failla, ML; Kumar, P. (2011). Anthocyanin Degradation in Human Saliva. Proceedings of the 2011 International Workshop on Anthocyanins. North Carolina, USA. vii 6. Kamonpatana, K; Moreno Cruz, M; Kumar, P; Giusti, MM; Failla, ML. (2011). Differential susceptibility of anthocyanins to degradation in human saliva. #098-18. 2011 IFT annual meeting, New Orleans, Louisiana, U.S.A. (First place, graduate student
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