Antioxidant Polymers Synthesis, Properties, and Applications

Giuseppe Cirillo obtained his PhD on "Methodologies for the Development of Molecules of Pharmaceutical Interest" in 2008 from University of Calabria, Italy. He is currently in a postdoctoral position at the same university and is CEO of Macrofarm, a University of Calabria spin-off company. He is also a visiting researcher at the Leibniz Institute for Solid State and Materials Research Dresden, Germany. He is the author or coauthor of more than 50 publications, including research and review articles as well as invited book chapters.

Francesca Iemma obtained her PhD in chemical sciences in 1997 from the University of Calabria. She is currently an associate professor in pharmaceutical technology in the faculty of Pharmacy, Nutrition and Health Sciences of the University of Calabria. She is a founding member of Macrofarm, a University of Calabria spin-off company. She has extensive teaching experience in the field of organic chemistry and pharmaceutical technology, and is author or coauthor of more than 80 publications, including research and review articles as well as invited book chapters.

Preface

List of contributors

1. Antioxidants: Introduction 1
Chunhuan He, Yingming Pan, Xiaowen Ji and Hengshan Wang

1.1 The Meaning of Antioxidant 1

1.2 The Category of Antioxidants and Introduction of often Used Antioxidants 2

1.3 Antioxidant Evaluation Methods 8

1.4 Antioxidant and its Mechanisms 13

1.5 Adverse Effects of Antioxidants 15

References 16

2. Natural Polyphenol and Flavonoid Polymers 23
Kelly C. Heim

2.1 Introduction 23

2.2 Structural Classification of Polyphenols 24

2.3 Polyphenol Biosynthesis and Function in Plants 34

2.4 Tannins in Human Nutrition 36

2.5 Antioxidant Activity of Tannins 41

2.6 Protective Effects of Proanthocyanidins in Human Health 45

2.7 Conclusion 46

Acknowledgements 46

References 47

3. Synthesis and Applications of Polymeric Flavonoids 55
Hiroshi Uyama and Young-Jin Kim

3.1 Introduction 55

3.2 Polycondensates of Catechin with Aldehydes 57

3.3 Enzymatically Polymerized Flavonoids 69

3.4 Biopolymer-. avonoid Conjugates 76

3.5 Conclusion 84

References 84

4. Antioxidant Polymers: Metal Chelating Agents 87
Hiba M. Zalloum and Mohammad S. Mubarak

4.1 Introduction 87

4.2 Chitin and Chitosan 91

4.3 Alginates 96

4.4 Chelation Studies 97

4.4.1 Chitosan Derivatives as Chelating Agents 101

4.5 Conclusions 106

References 107

5. Antioxidant Polymers by Chitosan Modi. cation 115
Jarmila Vinšová and Eva Vavr.íková

5.1 Introduction 115

5.2 Chitosan Characteristics 117

5.3 Reactive Oxygen Species and Chitosan as Antioxidant 117

5.4 Structure Modi. cations 120

5.5 Conclusion 129

References 129

6. Cellulose and Dextran Antioxidant Polymers for Biomedical Applications 133
Sonia Trombino, Roberta Cassano and Teresa Ferrarelli

6.1 Introduction 133

6.2 Antioxidant Polymers Cellulose-based 134

6.3 Antioxidant Polymers Dextran-based 142

References 149

7. Antioxidant Polymers by Free Radical Grafting on Natural Polymers 153
Manuela Curcio, Ortensia Ilaria Parisi, Francesco Puoci, Ilaria Altimari, Umile Gianfranco Spizzirri and Nevio Picci

7.1 Introduction 153

7.2 Grafting of Antioxidant Molecules on Natural Polymers 156

7.3 Proteins-based Antioxidant Polymers 157

7.4 Polysaccharides-based Antioxidant Polymers 164

7.5 Conclusions 175

Acknowledgements 176

References 176

8. 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

8.2 Antioxidant Activities of Marine Polysaccharides and their Derivatives 183

8.3 Applications of Marine Antioxidant Polysaccharides and their Derivatives 191

8.4 Structure-antioxidant Relationships of Marine Poly-/oligosaccharides 193

8.5 Conclusions 195

Acknowledgements 195

References 195

9. Antioxidant Peptides from Marine Origin: Sources, Properties and Potential Applications 203
Begoña Giménez, M. Elvira López-Caballero, M. Pilar Montero and M. Carmen Gómez-Guillén

9.1 Introduction 204

9.2 Whole Fish Hydrolysates 207

9.3 Marine Invertebrate Hydrolysates 223

9.4 Fish Frames Hydrolysates 227

9.5 Viscera Hydrolysates 228

9.6 Muscle Hydrolysates 232

9.7 Collagen and Gelatin Hydrolysates 240

9.8 Seaweeds Hydrolysates 243

9.9 Potential Applications 245

9.10 Conclusions 249

Acknowledgements 250

References 250

10. Synthetic Antioxidant Polymers: Enzyme Mimics 259
Cheng Wang, Gang-lin Yan and Gui-min Luo

10.1 Introduction 260

10.2 Organo-selenium/tellurium Compound Mimics 261

10.3 Metal Complex Mimics 281

10.4 Selenoprotein Mimics 295

10.5 Supramolecular Nanoenzyme Mimics 312

10.6 Conclusion 325

References 325

11. Synthetic Polymers with Antioxidant Properties 333
Ashveen V. Nand and Paul A. Kilmartin

11.1 Introduction 334

11.2 Intrinsically Conducting Polymers 335

11.3 Intrinsically Conducting Polymers with Antioxidant Properties 336

11.4 Synthesis of Antioxidant Intrinsically Conducting Polymers 337

11.5 Polymer Morphologies 340

11.6 Mechanism of Radical Scavenging 344

11.7 Assessment of Free Radical Scavenging Capacity 346

11.8 Factors Affecting the Radical Scavenging Activity 348

11.9 Polymer Blends and Practical Applications 350

References 351

12. Synthesis of Antioxidant Monomers Based on Sterically Hindered Phenols, a-Tocopherols, Phosphites and Hindered Amine Light Stabilizers (HALS) and their Copolymerization with Ethylene, Propylene or Styrene 355
Carl-Eric Wilén

12.1 Introduction 356

12.2 Synthesis of Antioxidant Monomers to Enhance Physical Persistence and Performance of Stabilizers 361

12.3 Phenolic Antioxidant Monomers and their Copolymerization with Coordination Catalysts 369

12.4 Copolymerization of Antioxidant Monomers with Ethylene, Propylene, Styrene and Carbon Monoxide Using Single Site Catalysts 372

12.5 Conclusions 379

Acknowledgements 380

References 380

13. Novel Polymeric Antioxidants for Materials 385
Ashish Dhawan, Vijayendra Kumar, Virinder S. Parmarand Ashok L. Cholli

13.1 Industrial Antioxidants 386

13.2 Antioxidants Used in Plastics (Polymer) Industry 386

13.3 Antioxidants Used in Lubricant Industry 389

13.4 Antioxidants Used in Elastomer (Rubber) Industry 390

13.5 Antioxidants Used in Fuel Industry 392

13.6 Antioxidants Used in Food Industry 393

13.7 Limitations of Conventional Antioxidants 395

13.8 Trends towards High Molecular Weight Antioxidants 396

13.9 Motivation, Design and Methodology for Synthesis of Novel Polymeric Antioxidant Motivation 407

13.10 Biocatalytic Synthesis of Polymeric Antioxidants 409

13.11 General Procedure for Enzymatic Polymerization 410

13.12 Conclusions 421

Acknowledgement 422

References422

14. Biopolymeric Colloidal Particles Loaded with Polyphenolic Antioxidants 427
A.R. Patel and K.P. Velikov

14.1 Introduction 427

14.2 Polyphenols: Antioxidant Properties and Health Benefits 428

14.3 Polyphenols: Formulation and Delivery Challenges 429

14.4 Polyphenols Loaded Biopolymeric Colloidal Particles 431

14.5 Conclusion 454

References 455

15. Antioxidant Polymers for Tuning Biomaterial Biocompatibility: From Drug Delivery to Tissue Engineering 459
David Cochran and Thomas D. Dziubla

15.1 Introduction 459

15.2 Oxidative Stress in Relation to Biocompatibility 460

15.3 Antioxidant Polymers in Drug Delivery 467

15.4 Antioxidant Polymers in Anti-cancer Therapies 470

15.5 Antioxidant Polymers in Wound Healing and Tissue Engineering 472

15.6 Conclusions and Perspectives 476

References 479

Index 485

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