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Extractability Profiling and Antioxidant Activity Of EXTRACTABILITY PROFILING AND ANTIOXIDANT ACTIVITY OF FLAVONOIDS IN SORGHUM GRAIN AND NON-GRAIN MATERIALS A Dissertation by NENGE LYNDA AZEFOR NJONGMETA Submitted to the Office of Graduate Studies of Texas A&M University in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY May 2009 Major Subject: Food Science and Technology EXTRACTABILITY PROFILING AND ANTIOXIDANT ACTIVITY OF FLAVONOIDS IN SORGHUM GRAIN AND NON-GRAIN MATERIALS A Dissertation by NENGE LYNDA AZEFOR NJONGMETA Submitted to the Office of Graduate Studies of Texas A&M University in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY Approved by: Chair of Committee, Lloyd W. Rooney Committee Members, Luis Cisneros-Zevallos Jimmy Keeton Steve Talcott Chair of Interdisciplinary Faculty, Jimmy Keeton May 2009 Major Subject: Food Science and Technology iii ABSTRACT Extractability Profiling and Antioxidant Activity of Flavonoids in Sorghum Grain and Non-grain Materials. (May 2009) Nenge Lynda Azefor Njongmeta, B.Sc. (Hons), Obafemi Awolowo University, Ile-Ife Nigeria; M.Sc. University of Ibadan, Nigeria Chair of Advisory Committee: Dr. Lloyd W. Rooney Grains, leaves, sheaths, glumes and stalks of sorghum varieties were analyzed for total phenols, condensed tannins, flavan-4-ols, anthocyanins and in vitro antioxidant activity. Black sorghum bran was used to evaluate the effectiveness of organic acids and enzymes on extractability of phenols. Flavonoid profiles of grains and non-grain tissues were determined and characterized using HPLC-PDA and HPLC-ESI-MS n. The presence of a pigmented testa and spreader genes (B 1B2S) is a predictor for polymeric flavonoids (tannins) but not for simple phenols such as flavan-4-ols, 3-deoxyanthocyanins, flavones and flavanones. Simple flavonoids increased antioxidant capacity of sorghum, and were present in all sorghum except for the white pericarp sorghums that did not have flavanones. The “red turning into black” gene increased phenols in Type I sorghum. The leaves, sheath and glumes of sorghum had higher levels of phenols iv (78-600 times more), with in vitro antioxidant properties than commonly seen in grains. Pigmentation of plant components increased levels of 3- deoxyanthocyanins but not flavones nor flavanones. The leaves of biomass sorghum, Collier variety, had 3.4 times more 3-deoxyanthocyanins than the leaves of Tx430 Black x Sumac which had the highest levels (1810 µg/g) of 3- deoxyanthocyanins among the leaves. The use of 1% HCl/ethanol provides a possible food grade substitute solvent for 1%HCl/methanol in the extraction of phenolic compounds from sorghum. All enzymes evaluated broke down bran particles forming a gel-like material which had increased phenols and antioxidant activities but not 3- deoxyanthocyanins as revealed by HPLC analysis. Microscopy examination showed the gel matrix rich in fiber and can possibly be used for nutraceutical applications. Careful understanding of enzyme activities is necessary for effective extraction of 3-deoxyanthocyanins from sorghum. Sorghum leaves, sheaths and glumes are excellent sources of bioactive compounds, up to 600 times more than the grains of some varieties. Sorghum with the “red turning to black genes” is a potential source of 3- deoxyanthocyanins and flavan-4-ols. With the trend towards sorghum as biomass for ethanol production, plant breeders must select special traits aimed at developing enhanced desired functionality such as antioxidant potential and other healthy attributes with application in food, pharmaceutical/nutraceutical and cosmetic industries. v DEDICATION To my children: Ndallah Ntunibu Njongmeta and Maema Shiminyie Njongmeta vi ACKNOWLEDGMENTS I would like to express my sincere appreciation to my supervisor Dr. Lloyd Rooney, for the opportunity to study under his guidance and most especially for his support in making it possible for me to achieve this milestone in my career. I am indebted to Dr. Jimmy Keeton for his keen interest in my career and for serving on my committee. I am also grateful to my other committee members: Dr. Luis Cisneros-Zevallos for his valuable feedback throughout my research and Dr. Steve Talcott for continuous guidance and for granting me unconditional access to his LS-MS and ORAC equipment. Special thanks to Dr. William Rooney for providing the samples for this work and for helping me understand the agronomics of sorghum. I appreciate the suggestions and comments from Dr. Joseph Awika and in whose lab part of the ORAC analysis was done. I wish to thank Dr. Linda Dykes for helping me understand HPLC analyses and for her comments and suggestions throughout my research; Lisbeth Pacheco-Palencia for taking me through Mass Spectrophotometry and Cassandra McDonough for her help with microscopy and for her friendship. My gratitude also goes to Victor Taleon for his help in sample collection from the field and for all his support. Thanks to Pamela Littlejohn for all she does. I am very appreciative of the team spirit, friendship and support of the members of the Cereal Quality Laboratory that I have worked with over the years. vii I wish to thank the Fulbright program for sponsorship to study at Texas A&M University and the University of Ngaoundere for granting me permission to pursue my studies. I owe many thanks to my Mum Emmerentia Azefor and Dad James Azefor (RIP) who instilled in me the gift of perseverance. I am particularly indebted to my brothers: Jude and Ephraim and my sisters: Mabi, Ngembong, Ngenwie and Ida for their outstanding love, support and encouragement. You all stand out in your unique nature. Special thanks to George, Atsi and Fred for their prayers and encouragement. Thanks to my nieces for all their prayers and their little giggles in very dark moments of my Ph.D program. Special thanks to Dr. Awahmukalah Dominic for his encouragement throughout my education. Special thanks to all my family and friends. I am indebted to Mr. Aloysius Chi and Mrs. Jackie Chi for their friendship and support. My most loving thanks are due my beloved husband and friend, Dr. Leo Moh Njongmeta; you held me up through the most challenging times in my life and through the toughest moments of my education. Thank you for believing in me more than I do in myself. Finally, I want to thank my kids, Mambo, Maema and Ndallah for their endurance, understanding, unflinching love and support; you are the reason I did this. Thank you for your ultimate cooperation. I want you to know you mean so much to me and I love you the whole wide world and back again. viii TABLE OF CONTENTS Page ABSTRACT ................................................................................................. iii DEDICATION .............................................................................................. v ACKNOWLEDGMENTS .............................................................................. vi TABLE OF CONTENT ................................................................................. viii LIST OF FIGURES ...................................................................................... xii LIST OF TABLES ........................................................................................ xix CHAPTER I INTRODUCTION ...................................................................... 1 II LITERATURE REVIEW ............................................................ 6 Sorghum kernel structure ..................................................... 6 The pericarp .................................................................... 6 The testa .......................................................................... 8 The endosperm ............................................................... 9 Germ................................................................................ 10 Classification of sorghum varieties based on tannin content ........................................................................ 10 Phenolic compounds in sorghum ........................................... 11 Phenolic acids ................................................................. 13 Tannins (polymeric flavonoids) ........................................ 15 Simple flavonoids in sorghum ......................................... 18 Structural features relevant to functions of phenolic compounds .............................................................. 23 Phenolic compounds as colorants ................................... 24 Phenolic compounds as antioxidants .............................. 25 Antimutagenic and anticarcinogenic properties of phenolic compounds ................................................... 27 Antimicrobial properties of phenolic compounds ............. 28 ix CHAPTER Page Phenolic compounds in non-grain materials of sorghum .............................................................. 29 Extraction of sorghum phenolic compounds ........................... 30 Analysis of phenolic compounds from sorghum ..................... 32 Folin-Ciocalteau assay .................................................... 33 Bleach Test ...................................................................... 33 Vanillin-hydrochloric acid (vanillin/HCl) method ............... 34 Butanol/HCl assay method for condensed tannins .......... 35 Modified Butanol/HCl method for flavan-4-ol ................... 36 pH Differential method for total anthocyanins .................. 36 Separation and identification of phenolic compounds using HPLC ……………………………… ............ 37 Determining antioxidant activity
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