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Bioactivities of Wood Polyphenols: Antioxidants and Biological Effects

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Bioactivities of Wood Polyphenols: Antioxidants and Biological Effects Bioactivities of Wood Polyphenols: Antioxidants and Biological Effects By Tasahil Albishi A thesis submitted in partial fulfilment of the requirements for the degree of Doctor of Philosophy of Science Department of Biochemistry Memorial University of Newfoundland August 2018 ST. JOHN’S NEWFOUNDLAND AND LABRADOR CANADA TABLE OF CONTENTS LIST OF ABBREVATION .................................................................................................... viii LIST OF TABLES ..................................................................................................................x LIST OF FIGURES ........................................................................................................... ……xi ABSTRACT ......................................................................................................................... xiv ACKNOWLEDGEMENTS .................................................................................................. xvii CHAPTER 1.0 – INTRODUCTION…………………………………………………….…...1 CHAPTER 2.0 - LITERATURE REVIEW …………………………………………..............5 2.1 Historical Background of wood……………………………………..…………… 5 2.1.1 Major uses of wood extractives…………..………..…………………….5 2.1.2 The use of woods……….……….…….……………………………...….6 2.2 Woody plants and their chemical composition……….….…………………..…...6 2.3 The chemistry of Wood ……….……...……….………….………….…............10 2.3.1 Cellulose ………….………….………………………………………... 10 2.3.2 Hemicellulose ……….…….……………………………………………11 2.3.3 Lignin ……………….……….…….………………...…………………12 2.3.4 Phenolic compounds….……….…………………………….……..…....14 2.4 Phenolics and their classifications……………………………………………….14 2.4.1 Major phenolics in woody plants….……………...…………………….16 2.4.1.1 Phenolic acids (hydroxybenzoic and hydroxycinnamic acids).…16 2.4.1.2 Flavonoids ……….……………………………………………....21 i 2.4.1.3 Tannins ……..……………………………………………………24 2.4.1.4 Lignans……..….…………………………………………………26 2.4.1.5 Lignin………....………………………………….………………26 2.4.1.6 Soluble- and insoluble-bound phenolic…………………………. 28 2.5 Phenolic antioxidant properties and their action mechanism……………. ….28 2.6 Natural antioxidants…………………………………………………….…….32 2.6.1 Date palm wood……………………………………………………….32 2.6.2 Oak wood…………….……………………………………………….34 2.6.3 Pinewood…………….………………………………………………...34 2.6.4 Quebracho wood……….………………………………………………35 2.6.5 Banana tree (Bark)………….………………………………………….36 CHAPTER 3.0 - MATERIALS AND METHODS .............................................................. 39 3.1 Materials……………………………………………………………………. 39 3.2 Methods……………………………………………………………………... 40 3.2.1 Extraction of phenolics………..……………………………………… 40 3.2.2 Determination of total phenolic content………………………………. 41 3.2.3 Determination of total flavonoids content ……………………………. 41 3.2.4 Determination of condensed tannins…..……….………………………42 3.2.5 Determination of hydrolyzable tannin content…………………………43 3.2.6 Determination of lignin content from extracted woods….…..…………43 3.2.7 Determination of the effect the antioxidant activities of Soluble and Insoluble phenolics extracted from wood varieties…………………………44 ii 3.2.7.1 Measurement of total antioxidant capacity by trolox equivalent antioxidant capacity (TEAC) assay ..................................................... 44 3.2.7.2 DPPH radical scavenging capacity (DRSC) using electron paramagnetic resonance (EPR) ............................................................ 45 3.2.7.3 Reducing power activity ........................................................... 46 3.2.7.4 Measurement of iron (II) chelation capacity ............................ 46 3.2.8 In in Vitro biological activities of wood extracts…………...................47 3.2.8.1 Effect of wood extracts on preventing cupric ion induced human low density lipoprotein (LDL) cholesterol peroxidation...................... 47 3.2.8.2 Supercoiled strand DNA scission by peroxyl and hydroxyl radicals ................................................................................................. 47 3.2.8.3 0 α-Glucosidase Inhibitory Activity...….…………………… 48 3.3 Analysis of phenolics and lignin extracted from woods……..……………….49 3.3.1 MALDI-TOF-MS analysis of structural the phenolics and Lignins of wood extracts…………………………………………………………………49 3.4 Date palm as a new source of phenolic antioxidants and in preparing smoked salmon……….………………………………………………………………50 3.4.1 Smoke processing ……………….…………………....……….….51 3.4.2 Extraction of soluble (SP) and insoluble-bound (IBP) phenolics from wood……...…………..……………………………………………52 3.4.3 Sampling………..……………………....…………..………….………52 3.4.4 Total phenolics (TPC) and flavonoids (TFC) contents of date palm and maple wood …………..………………………………………………….………54 3.4.5 DPPH radical scavenging capacity (DRSC) using electron paramagentic resonance (EPR) ………………..…………..………..………………………..54 3.4.6 Determination of volatile compounds of smoking wood using solid- phase microextraction (SPME) and gas chromatography–mass spectrometry iii (GC-MS) …………………….…..……………………………………………55 3.4.7 Determination of 2-thiobarbituric acid reactive substances (TBARS)..56 3.4.8 Colour measurement of smoked salmon………….………………..… 57 3.5. Statistical analysis……………………………………………………………..58 CHAPTER 4.0 - Low molecules weight phenolics of different Woods and their antioxidant activities……………………………..……………………………………………………. 59 4.1. Introduction…………………………………………………………………….59 4.2. Determination of total phenolic content ........................................................... 60 4.2.1 Total phenolic content…………………………………………………. 60 4.2.2 Total flavonoids content ......................................................................... 62 4.2.3 Condensed and hydrolyzable tannin contents of wood extracts.….……..65 4.2.4 Lignin contents of woods…………………………….…………………..67 4.3. Determination of the effect the antioxidant activities of SP and ISP extracted from wood varieties…..…………………………………………………………….70 4.3.1 Measurement of total antioxidant capacity by trolox equivalent antioxidant capacity (TEAC) assay .......................................................................................70 4.3.2 DPPH radical scavenging capacity (DRSC) using electron paramagnetic resonance (EPR) ............................................................................................... 71 4.3.3 Reducing power activity .......................................................................... 74 4.3.4 Measurement of Iron (II) Chelation Capacity ........................................... 75 4.4. Evaluation of antioxidant activity of wood extracts in biological model iv systems……………..……………………………………………...…………..77 4.4.1 Inhibition of Cupric Ion-Induced Human Low-Density Lipoprotein (LDL) Peroxidation………..………………………………………………..…78 4.4.2 Supercoiled strand DNA scission by peroxyl and hydroxyl radicals………………………………………………………………….83 4.4.3. α-Glucosidase Inhibitory Activity…….………………...…….………….91 4.4.4. MALDI-TOF-MS analysis of structural the phenolics of wood extracts……………………………………….......................................................95 4.4.5. Structure–activity relationships (SAR) of phenolics from wood varieties.….………………………………………………………………….......97 4.4.6 Phenolic compounds from woods as natural antioxidant source…….......100 CHAPTER 5.0 MALDI-MASS SPECTROMETRY AND TANDEM MASS SPECTROMETRY ANALYSIS OF A SERIES OF PROTONATED LIGNIN MOLECULES EXTRACTED FROM DATE PALM WOOD…………………….....……………..……….…102 5.1 Lignin introduction .................................................................................................. 102 5.2 MALDI-TOF-MS ................................................................................................... 109 5.3 Methods................................................................................................................... 110 5.3.1 Samples .................................................................................................…. 110 5.3.2 Lignin Oligomers Isolation ...................................................................…. 111 5.3.3 MALDI-TOF-MS Analysis ..................................................................…. 111 5.4 Results and Discussion ......................................................................................…. 112 v CHAPTER 6.0 – DATE PALM AS A NEW SOURCE OF PHENOLIC ANTIOXIDANTS AND AS A SOURCE OF WOODSMOKE IN PREPARATION OF SMOKED SALMON…….……………………………….…………………….………140 6.1 Introduction …………...……….…………………………………………...140 6.2. Experimental details ……………...……………………………………….142 6.3. Results and discussions………………….……...…………………………142 6.3.1 Screening the potential of date palm and maple wood as sources of phenolic antioxidants…………….……………………………………………………….142 6.3.2 Application of date palm and maple wood as sources of volatile phenolic antioxidants in smoked fish model system …………………..…….……..……145 6.3.2.1 Volatile compounds of smoking wood………..……........………….…145 6.3.2.2 Oxidative stability as affected by smoking with date palm and maple woods……………………………………………………………………….......148 6.3.3.3 Colour effects in smoked salmon………………….........………...........151 CHAPTER 7.0 - SUMMARY AND RECOMMENDATIONS ............................................153 Publications…. ...................................................................................................................156 REFERENCES…………………………………………………………...…………………157 vi Dedication I dedicate this document to my husband for his support, trust, motivation and being with me at every step of this journey. vii LIST OF ABBREVATIONS SPW Seedling date palm wood OPW Old date palm wood OW Oak wood QW Quebracho PW Pine wood BW Banana bark MAW Maple wood MALDI Matrix
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