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Phenolic Constituents of Georgia-Grown Blackberry Cultivars

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Phenolic Constituents of Georgia-Grown Blackberry Cultivars PHENOLIC CONSTITUENTS OF GEORGIA-GROWN BLACKBERRY CULTIVARS: FRACTIONATION AND CHARACTERIZATION OF THEIR ANTIOXIDANT, RADICAL- SCAVENGING, AND ANTI-INFLAMMATORY CAPACITIES by ANITA SRIVASTAVA (Under the direction of RONALD B. PEGG) ABSTRACT The aims of this work were to isolate and characterize phenolic constituents of Georgia- grown blackberry (Rubus spp.) cultivars (i.e., Navaho, Kiowa, and Ouachita) and to examine their antioxidant and anti-inflammatory capacities. Phenolic compounds were identified and quantified using HPLC and MS techniques. Column chromatography on Amberlite XAD-16 was employed to recover polyphenolic extracts, which were further fractionated on Sephadex LH-20. ESI-MS studies confirmed the presence of cyanidin-3-O-glucoside as the predominant anthocyanin in all the cultivars; cyanidin-3-O-rutinoside and cyanidin-3-O-xyloylrutinoside were also present in the Kiowa cultivar. Ellagitannin isomers; i.e., lambertianin A and lambertianin C were confirmed in all blackberry cultivars with pedunculagin and lambertianin D also being detected in Navaho and Kiowa blackberries, respectively. Total phenolics content (TPC) and total anthocyanins content were determined spectrophotometrically using the classical Folin- Ciocalteu assay and a pH differential method, respectively. Antioxidant capacities were assessed by the FRAP and TEAC assays; values for the preparations ranged from 26.1±2.7 to 178.1±6.9 mmol Fe2+ equivalents/100g of fraction (d.w.) and 13.6±0.7 to 79.4±0.9 μmol Trolox equivalents/g of fraction (d.w.), respectively. All fractions collected inhibited the formation of advanced glycation endproducts (AGEs); the % inhibition of AGEs ranged from 20.7±1.9 to 79.4±2.2%. Significant positive correlations (p<0.05) were determined for all fractions based on the TPC vs the FRAP and TEAC assays as well as % inhibition of protein glycation. The anti- inflammatory effects of low- and high-molecular-weight phenolic fractions (LMPF and HMPF, respectively) from blackberries were examined by assessing the effects of edema and polymorphonuclear (PMN) leukocyte infiltration 24 h after topical application of an irritant, 12- O-tetradecanoylphorbol-13-acetate (TPA), using the mouse ear model. The mouse ears of treatment groups were applied a solution of the LMPF, HMPF, or indomethacin, a non-steroidal anti-inflammatory drug (NSAID), 30 min after TPA application. The NSAID, LMPF, and HMPF (from all three cultivars) significantly (p<0.05) reduced TPA-induced injury when compared to the TPA-positive control group. Myeloperoxidase (MPO) activity, a biomarker for PMN leukocyte infiltration, was also significantly (p<0.05) reduced for treatment groups. Inhibition of both edema and MPO activity indicates marked anti-inflammatory activities arising from the phenolic constituents in the blackberries. INDEX WORDS: Blackberries, Polyphenolics, Anthocyanins, Hydrolyzable tannins, Sephadex LH-20 chromatography, Antioxidant activity, Anti-inflammatory activity, Myeloperoxidase activity, Advanced glycation endproducts PHENOLIC CONSTITUENTS OF GEORGIA-GROWN BLACKBERRY CULTIVARS: FRACTIONATION AND CHARACTERIZATION OF THEIR ANTIOXIDANT, RADICAL SCAVENGING, AND ANTI-INFLAMMATORY CAPACITIES by ANITA SRIVASTAVA B.S., University of Delhi, India, 1987 M.S., G. B. Pant University of Agriculture and Technology, India, 1990 M.S., University of Georgia, 2006 A Dissertation Submitted to the Graduate Faculty of the University of Georgia in Partial Fulfillment of the Requirements for the Degree DOCTOR OF PHILOSPHY ATHENS, GEORGIA 2009 © 2009 Anita Srivastava All Rights Reserved PHENOLIC CONSTITUENTS OF GEORGIA-GROWN BLACKBERRY CULTIVARS: FRACTIONATION AND CHARACTERIZATION OF THEIR ANTIOXIDANT, RADICAL- SCAVENGING, AND ANTI-INFLAMMATORY CAPACITIES by ANITA SRIVASTAVA Major Professor: Ronald B. Pegg Committee: Ronald R. Eitenmiller James L. Hargrove Diane K. Hartle Robert L. Shewfelt Electronic Version Approved: Maureen Grasso Dean of the Graduate School The University of Georgia December, 2009 DEDICATION Mom, Dad Anupam and Rahul iv ACKNOWLEDGMENTS I wish to express my sincere thanks to Dr Ronald B. Pegg, my major professor, for supporting me in the accomplishment of this doctoral program. Dr Pegg’s patience, positive attitude, and invaluable advice to work with finer details have helped me to become a better scientist and will be part of me in every walk of life. I would also like to thank my committee members Dr. Hartle, Dr. Hargrove, Dr. Eitenmiller, and Dr. Shewfelt for their constructive advice and support during my entire course of studies and research. This journey would have been incomplete without guidance and encouragement from Dr. Amarowicz and Dr. Greenspan. I owe special thanks to both of you. My thanks are also extended to Agnieszka Kosińska, Amy Burdette, Eve Bralley, Linda Duncan, Pamela Garner, and Vickie Wentzel for their help and support during my research studies. I am also grateful to UGA’s College of Agricultural and Environmental Sciences for providing financial support and to Jacob W. Paulk Farms, Inc. (Wray, GA) for supplying the blackberries for the study. I am so thankful to my parents Mohan and Shanti for believing in me and supporting my decision with unconditional love, my sisters Sunita, Asha, and Meenu for their love and encouragement. Indu and Sundeep thank you for your motivational talks. I would like to thank my husband, Anupam and my son Rahul for inspiring me and bringing laughter, compassion, and friendship to my life and for putting everything into perspective. v Last but not least, thanks to the faculty and staff of the Department of Food Science & Technology, UGA, for being part of my graduate student life and for their contributions to my personal and professional development. Anita Srivastava vi TABLE OF CONTENTS Page ACKNOWLEDGMENTS……………………………………………………………………….v LIST OF TABLES…………………………………………………………………....………….vii LIST OF FIGURES……………………………………………………………………….……....x CHAPTER 1. INTRODUCTION………………….……………………………………………….1 2. LITERATURE REVIEW……………………….…………………...….................14 3. CHARACTERIZATION OF PHENOLIC COMPOUNDS IN GEORGIA-GROWN BLACKBERRY CULTIVARS…………..……………..………….….................170 4. IN VITRO INHIBITION OF PROTEIN GLYCATION AND ANTIOXIDANT ACTIVITIES BY POLYPHENOLICS EXTRACTED FROM SOUTHEASTERN U.S. RANGE BLACKBERRIES……...………..………….…......…..…………..222 5. TOPICAL ANTI-INFLAMMATORY ACTIVITIES OF POLYPHENOLICS EXTRACTED FROM SOUTHEASTERN U.S. RANGE BLACKBERRY CULTIVARS USING THE 12-O-TETRADECANOYLPHORBOL-13-ACETATE (TPA) MODEL OF MOUSE EAR INFLAMMATION …..……….….................271 6. SUMMARY AND CONCLUSION……………………………………………...318 INDEX OF ABBREVIATIONS………..………………………………………………………321 vii LIST OF TABLES Page Table 2.1: Phenolic classes found in plants………….………………………………………36 Table 3.1: Relative yields (%) of CBEs and PPEs isolated from 100-g fresh blackberries of the Navaho, Kiowa, and Ouachita varieties…………….………………………202 Table 3.2: Phenolic compounds and selected phenolic classes identified in Georgia-grown Navaho, Kiowa, and Ouachita blackberries......………………………………...203 Table 3.3: Percent relative yield, total phenolics content, and total anthocyanins content of fractions isolated from Navaho, Kiowa, and Ouachita blackberry cultivars……204 Table 3.4: Phenolic compounds and selected phenolic classes identified in blackberry fractions of the Navaho cultivar…………………………………..…………….205 Table 3.5: Phenolic compounds and selected phenolic classes identified in blackberry fractions of the Kiowa cultivar…………...……………………………………..206 Table 3.6: Phenolic compounds and selected phenolic classes identified in blackberry fractions of the Navaho cultivar………………………………………….……..207 Table 3.7: Interpretation of the MALDI-TOF-MS for hydrolyzable tannins in the acetonic FXN-VII of Navaho blackberries…………….………….……………...............208 Table 4.1: Total phenolics content of ethanolic and acetonic fractions isolated from Navaho, Kiowa, and Ouachita cultivars of Georgia-grown blackberries using a Sephadex LH-20 column…………………………...………………………….……...……260 viii Table 4.2: Phenolic compounds identified in ethanolic and acetonic fractions isolated from Navaho, Kiowa, and Ouachita cultivars of Georgia-grown blackberries using a Sephadex LH-20 column…………….….…………………………...………….261 Table 5.1: Relative yield (%) of CBE, PPE, LMPF, and HMPF from lyophilized Georgia- grown blackberry cultivars (Navaho, Kiowa, and Ouachita)…………………...308 Table 5.2: Total phenolics content and antioxidant activity of the LMPF and HMPF from Georgia-grown blackberry cultivars (Navaho, Kiowa, and Ouachita)……….…309 Table 5.3: Experimental design for the TPA-induced mouse ear edema study….…………310 ix LIST OF FIGURES Page Figure 2.1: A commercial blackberry-growing operation in South Georgia and parts of the fruit…………………………………………………………………...…………..15 Figure 2.2: Biosynthesis of phenolic compounds…………………………………………….28 Figure 2.3: The phenolic acid family…………………………………………………………37 Figure 2.4: Other non-flavonoid phenolics of importance………………...………….………41 Figure 2.5: Basic structure and carbon-numbering system for the diphenylpropane (C6 – C3 – C6) nucleus of flavonoids…………………………………………...……………43 Figure 2.6: Chemical structures of selected compounds from the flavonoids’ family.......…..47 Figure 2.7: Chemical structures of selected compounds from the flavonoids’ family…….....51 Figure 2.8: Biosynthesis and hydrolysis of hydrolyzable tannins………………………...…..56 Figure 2.9: Chemical structures of selected hydrolyzable tannins and their monomers…...…59 Figure 2.10: Chemical structures of selected
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