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The Phenolics of Peanut Skins and Their Impact in Peanut

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THE PHENOLICS OF PEANUT SKINS AND THEIR IMPACT IN PEANUT BUTTER FORMULATIONS by YUANYUAN MA (Under the Direction of Ronald Bruce Pegg) ABSTRACT The overall aims of this work were to ascertain the primary phenolic constituents in peanut skins (PS), and to determine if their antioxidant content and capacities are conserved through industrial dry-blanching and roasting processes. The first and second studies undertaken revealed that ground PS incorporation into peanut butters effectively enhances the total phenolics and fiber contents of the product, and offers product-line diversification while still retaining the product’s standard of identity. This research will aid the peanut industry via (1) by-product/waste stream utilization; and (2) diversification of product lines by creating a value-added peanut butter with potential health beneficial properties. Adding ground PS to peanut butter at 1.25, 2.5, 3.75 and 5.0% (w/w) resulted in a concentration-dependent change in the Commission Internationale de l’Éclairage L* C* h values. Peanut butters formulated with medium- and dark-roasted PS showed an increase in hardness, and were generally more adhesive than those without PS or with dry-blanched PS added. A marked change in spreadability was found with greater than 2.5% PS fortification. Incorporation of dry-blanched PS, especially at levels below 3.75%, showed the fewest differences in terms of physical properties of the peanut butters relative to the control. Importantly, a concentration-dependent increase in the total phenolics content (TPC) was evident with PS fortification. Dry-blanched PS possessed a TPC of ~166 mg (+)-catechin equivalents/g extract and yielded peanut butters with a 32, 33 and 38% higher TPC than that for light-, medium- and dark-roasted skin incorporation on a same mass basis, respectively. Correspondingly, dry-blanched PS addition at 1.25, 2.5, 3.75 and 5.0% (w/w) resulted in an increase in the TPC by 86, 357, 533 and 714%, respectively, compared with peanut butters devoid of PS fortification; the total proanthocyanidins content (TPACs) rose by 633%, 1,933%, 3,500%, and 5,033%, respectively. Normal-phase high-performance liquid chromatography (NP-HPLC) detection confirmed that the increase in the phenolics content was attributed to the endogenous PACs from the PS, which were characterized as dimers to nonamers by ionization mass spectrometry (NP-HPLC/ESI-MS). FRAP values increased correspondingly by 62, 387, 747, and 829%, while H-ORACFL values rose by 53, 247, 382, and 415%, respectively. The dietary fiber (DF) content of dry-blanched PS was 55%, with 89 to 93% being insoluble fiber. The third and fourth studies undertaken involved liquid chromatography-electrospray ionization mass spectrometry (LC-ESI-MSn) characterization of free, as well as soluble-ester and glycoside-bound phenolic compounds from dry-blanched PS. A large variety of phenolic compounds, including phenolic acids (hydroxybenzoic acids, hydroxycinnamic acids, and their esters), stilbenes (trans-resveratrol and trans-piceatannol), flavan-3-ols (e.g., (–)-epicatechin, (+)-catechin, and their polymers {the proanthocyanidins, PACs}), other flavonoids (e.g., isoflavones, flavanols, and flavones) and biflavonoids (e.g., morelloflavone), were identified in dry-blanched PS by this study. PS provide an abundant and inexpensive source of natural antioxidants, especially p-coumaroyl species and PACs. All of these studies indicated that processing is altering the content of the phenolics in PS, but their antioxidant efficacy is retained in the product. INDEX WORDS: Peanut Skins (PS), Peanut Industry, Dry-blanching, Roasting, Antioxidants, Phenolics, Proanthocyanidins (PACs), high-performance liquid chromatography (HPLC), electrospray ionization mass spectrometry (ESI-MSn). THE PHENOLICS OF PEANUT SKINS AND THEIR IMPACT IN PEANUT BUTTER FORMULATIONS by YUANYUAN MA M.S., University of Kentucky, 2008 A Dissertation Submitted to the Graduate Faculty of the University of Georgia in Partial Fulfillment of the Requirements for the Degree DOCTORATE OF PHILOSOPHY ATHENS, GEORGIA 2014 © 2014 YUANYUAN MA All Rights Reserved THE PHENOLICS OF PEANUT SKINS AND THEIR IMPACT IN PEANUT BUTTER FORMULATIONS by YUANYUAN MA Major Professor:Ronald B. Pegg Committee: William L. Kerr Ruthann B. Swanson Phillip Greenspan Electronic Version Approved: Julie Coffield Interim Dean of the Graduate School The University of Georgia August 2014 DEDICATION I am indebted to my loving parents and husband for their unconditional support and encouragement during the entire course of my graduate study. Without their care, understanding, and trust, none of this would be possible. Also, to my beautiful kittens, who bring me laughter, companion, and emotional support. iv ACKNOWLEDGEMENTS I would like to take this opportunity to express my heartfelt gratitude to many people for helping and supporting me during my research. Thanks and appreciations especially go to my advisor and mentor, Dr. Ronald B. Pegg, who has guided me through each step of the research process, inspired my scientific thinking, and offered me financial support. It is such an honor to do my doctoral degree under his tutelage. Without his encouragement and patience, my academic career could never go any further. His great understanding and professionalism in regard to science will affect my career all my life. I must thank Drs. William L. Kerr, Ruthann B. Swanson, Phillip Greenspan, and James L. Hargrove for their willingness to serve on my committee as well as their support and contribution to my curriculum development and dissertation preparation. I would also like to thank Dr. Dennis R. Phillips from the Department of Chemistry. Thank you for your invaluable suggestions and technical support. My acknowledgements also extend to Drs. Ryszard Amarowicz and Agnieszka Kosińska-Cagnazzo of the Division of Food Science, Institute of Animal Reproduction and Food Research of the Polish Academy of Sciences, Olsztyn, Poland for their technical assistance. My many thanks must also go to my loving friends and lab mates for their willingness to share extensive knowledge of research with me and for their precious friendship. I am especially thankful to Ms. Vickie Wentzel and Marybeth Kellett for their selfless help during my research and dissertation writing. v Last but not least, I am indebted to my loving family, to whom I owe my undying gratitude; thank you for standing by me, through the good times and the bad. Sincerely, Yuanyuan Ma vi TABLE OF CONTENTS ACKNOWLEDGEMENTS……………………………………………………………………….v LIST OF TABLES………………………………………………………………………………..ix LIST OF FIGURES……………………………………………………………………………....xi CHAPTER 1 INTRODUCTION……………………………………………………………………….1 2 LITERATURE REVIEW……………………………………………………………….13 3 EFFECT OF PEANUT SKINS INCORPORATION ON THE COLOR, TEXTURE, AND TOTAL PHENOLICS CONTENT OF PEANUT BUTTERS…………………...70 4 PEANUT SKINS-FORTIFIED PEANUT BUTTERS: EFFECT OF PROCESSING ON THE PHENOLICS CONTENT, FIBER CONTENT AND ANTIOXIDANT ACTIVITY……………………………………………………………………………103 5 SEPARATION AND CHARACTERIZATION OF FREE PHENOLIC COMPOUNDS FROM DRY-BLANCHED PEANUT SKINS BY LIQUID CHROMATOGRAPHY-ELECTROSPRAY IONIZATION MASS SPECTROMETRY……………………………………………………………140 6 SEPARATION AND CHARACTERIZATION OF SOLUBLE-ESTER AND GLYCOSIDE-BOUND PHENOLIC COMPOUNDS FROM DRY-BLANCHED PEANUT SKINS BY LIQUID CHROMATOGRAPHY-ELECTROSPRAY IONIZATION MASS SPECTROMETRY……………………………………………202 vii 7 SUMMARY AND CONCLUSIONS…………………………………………………263 INDEX OF ABBREVIATIONS………………………………………………………………..265 viii LIST OF TABLES Table 2.1 Classification of major dietary phenolics and related food sources……………….57 Table 2.2 Basic carbon skeletons and structures of selected phenolic compounds…………..58 Table 3.1 Peanut butter formulations…………………………………………………………96 Table 3.2 Color analysis of formulated peanut butters……………………………………….97 Table 3.3 Textural properties of formulated peanut butters…………………………………..98 Table 3.4 Firmness and spreadability of formulated peanut butters………………………….99 Table 4.1 Total phenolics contents (TPCs) of peanut skins (PS) and PS-fortified peanut butters (PB), expressed as (+)-catechin equivalents/g PS of 100-g peanut butter……………………………………………………………………………...133 Table 4.2 Dietary fiber (DF) content (i.e., total, insoluble, and soluble, g/100 g) of peanut skins (PS) and PS-fortified peanut butters…………………………………....................134 Table 4.3 Proanthocyanidins (PACs) observed in peanut skins (PS) and dry-blanched (DB) PS-fortified peanut butters (0% skins vs 5% DB) based on NP-HPLC-ESI-MS analysis………………………………………………………………………........135 Table 5.1 Tentative identification of phenolic compounds in dry-blanched peanut skins (PS) by n C18 RP-HPLC-ESI-MS …………………………………………………………..175 Table 5.2 Tentative identification of proanthocyanidins (PACs) in dry-blanched peanut skins (PS) by HILIC-ESI-MS/MS……………………………………………………...182 ix Table 5.3 Content of selected phenolics quantified in dry-blanched peanut skins (PS) by C18 RP-HPLC…………………………………………………………………………186 Table 5.4 Quantification of proanthocyanidin (PAC) compounds in dry-blanched peanut skins (PS) by HILIC……………………………………………………………………187 Table 6.1 Tentative identification of phenolic compounds in dry-blanched peanut skins (PS) crude extracts by C18 RP-HPLC-ESI-MS/MS…………………………………….238 Table 6.2 Tentative identification of ester-bound phenolic compounds in dry-blanched peanut skins (PS) by C18 RP-HPLC-ESI-MS/MS………………………………………...240 Table 6.3 Tentative identification of glycoside-bound phenolic compounds in dry-blanched n peanut
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    420 Penetration of the Polyflavonoids and Simple Phenolics: A Mechanistic Investigation of Vegetable Tanning by Bo Teng,1 Jiacheng Wu1 and Wuyong Chen1,2* 1National Engineering Laboratory for Clean Technology of Leather Manufacture, Sichuan University, 610065, Chengdu, P.R. China 2Key Laboratory for Leather Chemistry and Engineering of the Education Ministry, Sichuan University, 610065, Chengdu, P.R. China Abstract to help improving the vegetable tanning agents crafts, leather chemists put in massive amounts of efforts to study the Mechanisms of tanning are the fundamental base for predicting mechanisms which age-related the tannin-collagen 4-6 and developing new tanning agents and technologies. However, interactions. many mechanistic questions remain for us, such as: How does the penetration happen? How do the phenolic compounds work The hydrophobic-hydrogen bonding theory is widely accepted to individually? In this study, penetration processes of the tannin describe the interactions between proteins and phenolics. This extracts were investigated with the Bayberry extract theory highlights the importance of both hydrophobic and (prodelphenidins), the Larch extract (procyanidins) and the hydrophilic sites of the tannin and protein molecules, meanwhile Acacia Mangiumextract (prodelphenidin-procyanidin it is considered as the fundamental base to understand their 7-8 complexes) used as tanning agents. During the process, the interactions. Covington provided the “rigid, non-rigid” theory tanning liquids were regularly sampled and the simple phenolics and deduced the relationships between structural and thermal 9 and polyflavonoids were quantified respectively with a Prussian properties. In this theory, not only the hydrogen bonds, but also blue assay, a conductivity analysis, an acid-butanol assay as well the size and rigidity of the tannin molecules are all considered as as a HPLC analysis.
  • Polymerization Degrees, Molecular Weights and Protein-Binding Affinities of Condensed Tannin Fractions from a Leucaena Leucocephala Hybrid

    Polymerization Degrees, Molecular Weights and Protein-Binding Affinities of Condensed Tannin Fractions from a Leucaena Leucocephala Hybrid

    Molecules 2014, 19, 7990-8010; doi:10.3390/molecules19067990 OPEN ACCESS molecules ISSN 1420-3049 www.mdpi.com/journal/molecules Article Polymerization Degrees, Molecular Weights and Protein-Binding Affinities of Condensed Tannin Fractions from a Leucaena leucocephala Hybrid Mookiah Saminathan 1, Hui Yin Tan 2, Chin Chin Sieo 1,3, Norhani Abdullah 3,4, Clemente Michael Vui Ling Wong 5, Emilia Abdulmalek 6 and Yin Wan Ho 1,* 1 Institute of Bioscience, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia; E-Mails: [email protected] (M.S.); [email protected] (C.C.S.) 2 Faculty of Applied Sciences and Computing, Tunku Abdul Rahman University College, 53300 Kuala Lumpur, Malaysia; E-Mail: [email protected] 3 Faculty of Biotechnology and Biomolecular Sciences, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia; E-Mail: [email protected] 4 Institute of Tropical Agriculture, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia 5 Biotechnology Research Institute, Universiti Malaysia Sabah, Jalan UMS, 88400 Kota Kinabalu, Sabah, Malaysia; E-Mail: [email protected] 6 Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia; E-Mail: [email protected] * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +603-8947-2161; Fax: +603-8947-2101. Received: 18 March 2014; in revised form: 11 May 2014 / Accepted: 21 May 2014 / Published: 12 June 2014 Abstract: Condensed tannins (CTs) form insoluble complexes with proteins and are able to protect them from degradation, which could lead to rumen bypass proteins. Depending on their degrees of polymerization (DP) and molecular weights, CT fractions vary in their capability to bind proteins.