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Composition of Flavonoid Phenolic Polymers Isolated from Red Wine During Maceration and Significance of Flavan-3-Ols in Foods Pertaining to Biological Activity

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Composition of Flavonoid Phenolic Polymers Isolated from Red Wine During Maceration and Significance of Flavan-3-Ols in Foods Pertaining to Biological Activity AN ABSTRACT OF THE THESIS OF Patricia M. Aron for the degree of Masters of Science in Food Science and Technology, presented on March 12, 2007. Title: Composition of Flavonoid Phenolic Polymers Isolated From Red Wine During Maceration and Significance of Flavan-3-ols in Foods Pertaining to Biological Activity. Abstract approved: _________________________________________________ James A. Kennedy Representing the most common flavonoid consumed in the American diet, the flavanols and their polymeric condensation products, the proanthocyanidins, are regarded as functional ingredients in various beverages, whole and processed foods, herbal remedies and supplements. Their presence in food affects food quality parameters including astringency, bitterness, sourness, sweetness, salivary viscosity, aroma, and color formation. The ability of flavonoids to aid food functionality has also been established in terms of microbial stability, foamability, oxidative stability, and heat stability. Phenolic polymer material of the flavonoid family is of considerable interest in the study of red wine, as phenolic quantity and structure can significantly affect wine quality. Although a considerable amount of the phenolic polymer material extracted into red wine during fermentation can be accounted for and characterized as known compounds, a substantial portion of the material remains uncharacterized. During this investigation phenolic polymer material extracted during commercial red wine fermentations (Vitis vinifera L.cv Pinot noir) was isolated and analyzed in order to characterize its chemical composition. Phenolic polymer isolates were prepared from samples taken throughout fermentation and isolated by adsorption chromatography. Isolates were subjected to phloroglucinolysis to analyze proanthocyanidin amount as well as subunit composition. Investigation results revealed that known proanthocyanidin content of individual phenolic polymer isolates varied from 27 to 54%. Subsequent analyses were performed in order to quantify material other than known proanthocyanidin subunits. Results of all experiments accounted for up to 82% of the phenolic polymer isolates by mass. Phenolic polymers such as the proanthocyanidins have also become the interest of several investigations due to their potential to provide a variety of health beneficial effects by acting as antioxidant, anticarcinogen, cardiopreventive, antimicrobial, anti-viral, and neuro-protective agents. Such health beneficial effects have been correlated to proanthocyanidin structure-related functionality that allows them to behave as signaling molecules at the molecular level. Consumption of proanthocyanidin rich foods has also reportedly been linked to health detrimental effects including the activation of procarcinogens, reactive oxygen species formation (pro-oxidant activity), hemorrhage formation, hepatotoxicity initiation, pharmacokinetics of therapeutic drug alteration, estrogenic tumor formation, mutagenicity, plasma biochemistry modification, gastroenteritis instigation, antinutritive activity and weight loss. ©Copyright by Patricia M. Aron March 12, 2007 All Rights Reserved Composition of Flavonoid Phenolic Polymers Isolated From Red Wine During Maceration and Significance of Flavan-3-ols in Foods Pertaining to Biological Activity by Patricia M. Aron A THESIS submitted to Oregon State University in partial fulfillment of the requirements for the degree of Master of Science Presented March 12, 2007 Commencement June 2007 Master of Science thesis of Patricia M. Aron presented on March 12, 2007. APPROVED: Major Professor, representing Food Science & Technology Head of the Department of Food Science & Technology Dean of the Graduate School I understand that my thesis will become a part of the permanent collection of Oregon State University libraries. My signature below authorizes release of my thesis to any reader upon request. Patricia M. Aron, Author ACKNOWLEDGEMENTS Great thanks and appreciation goes toward my major professor Dr. James A. Kennedy, whose support and guidance enabled me to complete my tenure at Oregon State University with a degree in Food Science and Technology. I also gratefully acknowledge the Northwest Center for Small Fruits Research for financial support and Drs. Parastoo Azadi and Christian Heiss of the Complex Carbohydrate Research Center for their analytical services. Thank you to my research colleagues for their peer support and friendship: Seth, Fiorella, Tiago, Jessica, Katty, Jorge, Richard, and Jose. Finally I also thank Willakenzie Estates Winery of Yamhill, OR, for their collaboration and assistance in the commercial production of the wine used in this study. CONTRIBUTION OF AUTHORS TABLE OF CONTENTS Page Introduction .............................................................................................................1 The flavonoids...................................................................................................1 The flavonoids....................................................................................... 1 The 2-phenylbenzopyrans ..................................................................... 2 The proanthocyanidins ...........................................................................3 Proanthocyanidin function in plants.......................................................5 Proanthocyanidins, Food, Consumption and Bioavailability............................6 Effect on food quality............................................................................6 Presence in Food....................................................................................6 Food consumption and bioavailability ..................................................8 Proanthocyanidins and Health.........................................................................10 Proanthocyanidin antioxidant character ..............................................10 Proanthocyanidins metal chelating activity.........................................12 Proanthocyanidins and cardiovascular disease....................................12 Proanthocyanidins and cancer .............................................................13 Deleterious effects of proanthocyanidin consumption........................14 Flavonoids and Wine.......................................................................................15 Importance and origin of polyphenols in red wine..............................15 Wine proanthocyanidins......................................................................16 Wine flavonols, flavanonols and anthocyanins...................................16 TABLE OF CONTENTS(continued) Page Proanthocyanidin chemistry during berry ripening.............................17 Proanthocyanidin extraction during red wine production ...................18 Anthocyanin extraction during red wine fermentation........................19 Proanthocyanidin reactions during red wine aging .............................19 Proanthocyanidin Effect on Red Wine Quality...............................................20 Astringency..........................................................................................21 Proanthocyanidin oxidation.................................................................22 Polysaccharides and Modification of Astringency..........................................24 Polysaccharides and berry development .............................................24 Grape polysaccharides.........................................................................25 Must and wine polysaccharides...........................................................27 Yeast derived polysaccharide..............................................................29 Polysaccharide influence on astringency.............................................29 Research Justification and objectives...........................................................30 Figures ..........................................................................................................32 Composition of Phenolic Polymers Isolated from Red Wine During Maceration. .........................................................................................................................41 Abstract............................................................................................................42 Introduction .....................................................................................................42 Materials and Methods ....................................................................................46 TABLE OF CONTENTS(continued) Page Results and Discussion....................................................................................51 Conclusion.......................................................................................................75 Acknowledgement...........................................................................................77 Figures ............................................................................................................78 Tables .............................................................................................................86 Flavan-3-ols: Nature, Occurrence and Biological Activity………………………94 Abstract............................................................................................................95 Introduction .....................................................................................................97 Flavonoids .......................................................................................................97
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