Antioxidant Polymers WILEY. Synthesis, Properties, and Applications. Giuseppe Cirillo. Francesca lemma. Edited by. and

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1 Antioxidant Polymers Synthesis, Properties, and Applications Edited by Giuseppe Cirillo and Francesca lemma Department of Pharmaceutical Sciences, University of Calabria, Italy Scrivener WILEY

2 Contents Preface List of Contributors xv xix 1. Antioxidants: Introduction 1 He, Pan, Ji and Wang 1.1 The Meaning of Antioxidant 1 The Category of Antioxidants and Introduction of often Used Antioxidants BHT Quercetin BHA (TBHQ) Gallic Acid Resveratrol Luteolin Antioxidant Evaluation Methods DPPH Radical Scavenging Assay ABTS Radical Scavenging Activity Assay Reducing Power Assay Total Phenols Assay by Reagent Hydroxyl Radical Scavenging Assay Acid Assay Superoxide Radical Scavenging Assay 11 Metal Ion Chelating Assay Determination of Total Flavonoid Content 12

3 vi CONTENTS 1.4 Antioxidant and its Mechanisms Mechanism of Free Radicals Mechanism of Metal Chelating Properties Adverse Effects of Antioxidants 15 References Natural Polyphenol and Flavonoid Polymers 23 Kelly C. 2.1 Introduction Structural Classification of Polyphenols Simple Phenolics Stilbenes Lignin Flavonoids Tannins Polyphenol Biosynthesis and Function in Plants Biosynthesis Protective Roles Tannins in Human Nutrition Dietary Sources and Intake Absorption and Metabolism Antioxidant Activity of Tannins Mechanisms Structure-activity Relationships Protective Effects of Proanthocyanidins in Human Health Conclusion 46 Acknowledgements 46 References Synthesis and Applications of Polymeric Flavonoids 55 Hiroshi and Young-Jin Kim 3.1 Introduction Polycondensates of Catechin with Aldehydes Enzymatically Polymerized Flavonoids Biopolymer-flavonoid Conjugates Conclusion 84 References 84

4 Antioxidant Polymers: Metal Chelating Agents 87 Hiba M. Zalloum and Mohammad S. Mubarak 4.1 Introduction Antioxidants Natural Polymers as Antioxidants Chelating Polymers and Heavy Metal Ions Chitin and Chitosan Chitin and Chitosan Derivatives Chitin and Chitosan as Chelating Agents Alginates Chelation Studies Chitosan Derivatives as Chelating Agents Alginates as Chelating Agents Conclusions 106 References 107 Antioxidant Polymers by Chitosan Modification 115 Jarmila and Eva 5.1 Introduction Chitosan Characteristics Reactive Oxygen Species and Chitosan as Antioxidant 5.4 Structure Modifications Chitosan Derivatives Quaternary Salts Sulphur Derivatives Chitosan Containing Phenolic Compounds Schiff Bases of Chitosan Conclusion 129 References 129 Cellulose and Dextran Antioxidant Polymers for Biomedical Applications 133 Trombino, Roberta Cassano and Teresa Ferrarelli 6.1 Introduction Antioxidant Polymers Cellulose-based Cellulose Antioxidant Biomaterials Lipoate and Tocopherulate Cellulose 136

5 viii CONTENTS Cellulose Hydrogel Containing Trans-ferulic Acid Polymeric Antioxidant Membranes Based on Modified Cellulose and Blends Synthesis of Antioxidant Novel Broom and Cotton Fibers Derivatives 6.3 Antioxidant Polymers Dextran-based Dextran Biocompatible Dextran-coated Nanoceria with ph-dependent Antioxidant Properties Coniugates of Dextran with Antioxidant Properties Dextran Hydrogel Linking Trans-ferulic Acid for the Stabilization and Transdermal Delivery of Vitamin E References Antioxidant Polymers by Free Radical Grafting on Natural Polymers 153 Manuela Curcio, Ortensia Ilaria Parisi, Francesco Puoci, Ilaria Altimari, Gianfranco Spizzirri and Nevio Picci 7.1 Introduction Grafting of Antioxidant Molecules on Natural Polymers Proteins-based Antioxidant Polymers Antioxidant Polymers Chitosan Starch Inulin and Alginate Conclusions 175 Acknowledgements 176 References Natural Polymers with Antioxidant Properties: Poly-/oligosaccharides of Marine Origin 179 Guangling Jiao, Guangli Yu, Xiaoliang Zhao, Junzeng Zhang and H. Stephen Ewart 8.1 Introduction to Polysaccharides from Marine Sources

6 CONTENTS ix Polysaccharides from Marine Algae Polysaccharides from Marine Invertebrates Marine Bacteria Polysaccharides Antioxidant Activities of Marine Polysaccharides and their Derivatives Antioxidant Evaluation Methods Marine Sulfated Polysaccharides Marine Uronic Acid-containing Polysaccharides Marine Non-acidic Polysaccharides and their Oligomers Marine Glycoconjugates Applications of Marine Antioxidant Polysaccharides and their Derivatives Applications in Food Industry Applications as Medicinal Materials Applications as Cosmetic Ingredients Applications in Other Fields Structure-antioxidant Relationships of Marine Poly-/oligosaccharides Conclusions 195 Acknowledgements 195 References 195 Antioxidant Peptides from Marine Origin: Sources, Properties and Potential Applications 203 Gimenez, M. Elvira M. Pilar Montero Carmen Gomez-Guillen 9.1 Introduction Whole Fish Hydrolysates Marine Invertebrate Hydrolysates Fish Frames Hydrolysates Viscera Hydrolysates Muscle Hydrolysates Collagen and Gelatin Hydrolysates Seaweeds Hydrolysates Potential Applications Conclusions 249 Acknowledgements 250 References 250

7 x CONTENTS 10. Synthetic Antioxidant Polymers: Enzyme Mimics 259 Cheng Wang, Yan and Gui-min Luo 10.1 Introduction /tellurium Compound Mimics Chemistry of Synthetic Compounds as GPX Mimics Mimics Metal Complex Mimics The Role of Metal Ions in Complexes Manganese Complexes Mimics Other Metal Complex Mimics Selenoprotein Mimics 295 Strategies of Selenoprotein Synthesis Synthetic Selenoproteins Supramolecular Nanoenzyme Mimics 312 of Supramolecular Nanoenzyme Mimics Supramolecular Nanoenzyme Mimics with Antioxidant Acitivity 10.6 Conclusion 325 References Synthetic Polymers with Antioxidant Properties 333 Ashveen V. Nand and Paul A. Kilmartin 11.1 Introduction Intrinsically Conducting Polymers 335 Intrinsically Conducting with Antioxidant Properties 336 Synthesis of Antioxidant Intrinsically Conducting Polymers Chemical Synthesis Electrochemical Synthesis Other Polymerization Techniques Polymer Morphologies Polyaniline Polypyrrole Poly(3,4-ethylenedioxythiophene) Mechanism of Radical Scavenging Assessment of Free Radical Scavenging Capacity Assay Assay 347

8 CONTENTS xi 11.8 Factors Affecting the Radical Scavenging Activity Polymer Blends and Practical Applications 350 References Synthesis of Antioxidant Monomers Based on Sterically Hindered Phenols, Phosphites and Hindered Amine Light Stabilizers (HALS) and their Copolymerization with Ethylene, Propylene or Styrene 355 Carl-Eric 12.1 Introduction Synthesis of Antioxidant Monomers to Enhance Physical Persistence and Performance of Stabilizers Copolymerization of Antioxidants with Using Coordination Catalysts Synthesis of Antioxidant Monomers Phenolic Antioxidant Monomers and their Copolymerization with Coordination Catalysts 369 of Antioxidant Monomers with Ethylene or Propylene using Traditional Catalysts Copolymerization of Antioxidant Monomers with Ethylene, Propylene, Styrene and Carbon Monoxide Using Single Site Catalysts Copolymerization of Phenolic Antioxidant Monomers Copolymerization of HALS Monomers using Single Site Catalysts Conclusions 379 Acknowledgements 380 References Novel Polymeric Antioxidants for Materials 385 Ashish Vijayendra Kumar, Virinder S. Ashok L. Cholli 13.1 Industrial Antioxidants Antioxidants Used in Plastics (Polymer) Industry Primary Antioxidants Secondary Antioxidants Antioxidants Used in Lubricant Industry 389

9 xii CONTENTS Antioxidants Used in Elastomer (Rubber) Industry Antioxidants Used in Fuel Industry Antioxidants Used in Food Industry Natural Food Antioxidants Synthetic Food Antioxidants Limitations of Conventional Antioxidants 395 Performance Issues because of Antioxidant Efficiency Loss Environmental Issues and Safety Concerns Compatibility Issues Poor Thermal Stability Trends towards High Molecular Weight Antioxidants Functionalization of Conventional Antioxidants with Hydrocarbon Chains Macromolecular Antioxidants Polymer-bound Antioxidants Polymeric Antioxidants Motivation, Design and Methodology for Synthesis of Novel Polymeric Antioxidant Motivation Design of the Polymeric Antioxidants Methodology 408 Synthesis of Polymeric Antioxidants General Procedure for Enzymatic Polymerization 410 Synthesis and Characterization of Polymeric Antioxidants Antioxidant Activity of Polymeric Antioxidants Evaluation of Polymeric Antioxidants in Vegetable Oils by Accelerated Oxidation Conclusions 421 Acknowledgement 422 References Biopolymeric Colloidal Particles Loaded with Polyphenolic Antioxidants 427 Ashok JR. and Krassimir P. Velikov 14.1 Introduction Polyphenols: Antioxidant Properties and Health Benefits 428

10 CONTENTS xiii 14.3 Polyphenols: Formulation and Delivery Challenges Solubility Chemical Reactivity and Degradation Stability in Physiological Conditions First Pass Metabolism and Pharmacokinetics Organoleptic Properties and Aesthetic Appeal Polyphenols Loaded Biopolymeric Colloidal Particles Curcumin Loaded Biopolymeric Colloidal Particles Loaded Biopolymeric Colloidal Particles Quercetin Loaded Biopolymeric Colloidal Particles Conclusion 454 References Antioxidant Polymers for Tuning Biomaterial Biocompatibility: From Drug Delivery to Tissue Engineering 459 David Cochran and Thomas D. Dziubla 15.1 Introduction Oxidative Stress in Relation to Biocompatibility Mechanism of Immune Response Examples in Practice Antioxidant Polymers in Drug Delivery Uses as Active Pharmaceutical Ingredients Uses as Pharmaceutical Excipients Antioxidant Polymers in Anti-cancer Therapies Antioxidant Polymers in Wound Healing and Tissue Engineering Antioxidant Polymers Incorporated into Biomaterials Conclusions and Perspectives 476 References 479 Index 485