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Book Details
Abstract
Interest in anthocyanins has increased in the past few years, due to their potential health-promoting properties as dietary antioxidants. Previously they were known as an important class of natural colorant, orange-red to blue-violet, found in fruits such as berries and in vegetables. This book discusses ways of targeting the delivery of these compounds, through manipulation of exploitation mechanisms. It addresses all aspects from extraction of anthocyanins from natural sources, their health benefits and metabolism to specialized controlled release applications. It will serve as a unique reference for those specializing in the fate of anthocyanins in the body (pharmacokinetics) and the research related to controlled release systems. It will provide an insight for pharmaceutical scientists, food engineers, food scientists and those interested in human health and nutrition.
Table of Contents
| Section Title | Page | Action | Price |
|---|---|---|---|
| Cover | Cover | ||
| Preface | v | ||
| Contents | ix | ||
| Part I Chemistry and Extraction of Anthocyanins | 1 | ||
| Chapter 1 Natural Sources of Anthocyanins | 3 | ||
| 1.1 Introduction | 3 | ||
| 1.2 Anthocyanins in Foods | 5 | ||
| 1.2.1 Fruits | 5 | ||
| 1.2.1.1 Apple: Malus pumila L. | 5 | ||
| 1.2.1.2 Apricot: Prunus armeniaca L. | 5 | ||
| 1.2.1.3 Bilberry: Vaccinium myrtillus L. | 5 | ||
| 1.2.1.4 Blackberry: Rubus allegheniensis Porter and Other Rubus Species | 6 | ||
| 1.2.1.5 Blueberry: V. corymbosum L. (Highbush Blueberry) and V. angustifolium Ait. (Lowbush Blueberry) | 6 | ||
| 1.2.1.6 Cherry: Prunus avium L. and Other Prunus Species | 6 | ||
| 1.2.1.7 Cranberry: V. oxycoccus L. (European Cranberry) and V. macrocarpon Ait. (American Cranberry) | 6 | ||
| 1.2.1.8 Currant: Ribes rubrum L. (Redcurrant) and R. nigrum L. (Blackcurrant) | 7 | ||
| 1.2.1.9 Grape: Vitis vinifera L. and Other Vitis Species | 7 | ||
| 1.2.1.10 Haskap Berry: Lonicera caerulea L. | 7 | ||
| 1.2.1.11 Mulberry: Morus alba L. | 7 | ||
| 1.2.1.12 Orange: Citrus sinensis L. | 7 | ||
| 1.2.1.13 Peach: Prunus persica L. | 8 | ||
| 1.2.1.14 Pear: Pyrus spp. | 8 | ||
| 1.2.1.15 Plum: Prunus domestica L. and Other Prunus Species | 9 | ||
| 1.2.1.16 Pomegranate: Punica granatum L. | 9 | ||
| 1.2.1.17 Rosehip: Rosa canina L. and Other Rosa Species | 9 | ||
| 1.2.1.18 Saskatoon Berry: Amelanchier alnifolia Nutt. | 9 | ||
| 1.2.1.19 Strawberry: Fragaria x ananassa Duch. | 9 | ||
| 1.2.2 Legumes and Vegetables | 9 | ||
| 1.2.2.1 Asparagus: Asparagus officinalis L. | 9 | ||
| 1.2.2.2 Bean: Phaseolus spp. | 10 | ||
| 1.2.2.3 Cabbage: Brassica oleracea L. var. capitata f. rubra | 10 | ||
| 1.2.2.4 Carrot: Daucus carota L. | 10 | ||
| 1.2.2.5 Cauliflower: Brassica oleracea L. var. botrytis | 10 | ||
| 1.2.2.6 Eggplant: Solanum melongena L. | 11 | ||
| 1.2.2.7 Ginger: Zingiber officinale Roscoe | 11 | ||
| 1.2.2.8 Lentil: Lens culinaris Medic. | 11 | ||
| 1.2.2.9 Pea: Pisum sativum L. | 12 | ||
| 1.2.2.10 Peanut: Arachis hypogaea L. | 12 | ||
| 1.2.2.11 Pepper: Capsicum annuum L. | 12 | ||
| 1.2.2.12 Potato: Solanum tuberosum L. | 12 | ||
| 1.2.2.13 Onion: Allium cepa L. | 12 | ||
| 1.2.2.14 Radish: Raphanus sativus L. | 13 | ||
| 1.2.2.15 Rhubarb: Rheum spp. | 13 | ||
| 1.2.2.16 Soybean: Glycine max (L.) Merr. | 13 | ||
| 1.2.2.17 Sweet Potato: Ipomoea batatas L. | 13 | ||
| 1.2.2.18 Turnip: Brassica campestris L. | 14 | ||
| 1.2.3 Cereal Grains | 14 | ||
| 1.2.3.1 Barley: Hordeum vulgare L. | 14 | ||
| 1.2.3.2 Corn: Zea mays L. | 14 | ||
| 1.2.3.3 Rice: Oryza sativa L. | 14 | ||
| 1.2.3.4 Rye: Secale cereale L. | 15 | ||
| 1.2.3.5 Sorghum: Sorghum bicolor (L.) Moench. | 15 | ||
| 1.2.3.6 Wheat: Triticum spp. | 15 | ||
| 1.3 Anthocyanins in Herbs and Plants of Traditional Medicine | 15 | ||
| 1.3.1 Traditional Chinese Medicine | 16 | ||
| 1.3.1.1 Da Zao (Jujube, Chinese Date): Ziziphus jujube Mill. | 16 | ||
| 1.3.1.2 Juju (Chicory): Cichorium glandulosum Bioss. et Huet or C. intybus L. | 17 | ||
| 1.3.1.3 Sha Ji (Common Sea Buckthorn): Hippophae rhamnoides L. | 17 | ||
| 1.3.1.4 Shan Zha (Chinese Hawthorn, Mountain Hawthorn): Crataegus pinnatifida Bge. | 17 | ||
| 1.3.1.5 Shan Zhu Yu (Japanese Cornel, Cornelian Cherry): Cornus officinalis Sieb. et Zucc. | 17 | ||
| 1.3.1.6 Wu Wei Zi (Chinese Magnolia Berry, Five-flavor Fruit): Schisandra chinensis (Turcz.) Baill. | 18 | ||
| 1.3.1.7 Zi Hua Di Ding: Viola yedoensis Makino | 18 | ||
| 1.3.1.8 Zi Su: Perilla frutescens (L.) Britt. | 19 | ||
| 1.3.2 Indian Ayurvedic Medicine | 19 | ||
| 1.3.2.1 Adhaki: Cajanus cajan (L.) Millsp. (pigeon pea) | 19 | ||
| 1.3.2.2 Kamala: Nelumbo nucifera Gaertn. (Syn. Nelumbium speciosum Willd.) | 19 | ||
| 1.3.2.3 Kharjura: Phoenix dactylifera L. (Date Palm) | 20 | ||
| 1.4 Anthocyanins in Exotic Plants from Around the World | 20 | ||
| 1.4.1 Açai Berry: Euterpe oleraceae Mart. | 20 | ||
| 1.4.2 Andes Berry: Rubus glaucus Benth | 20 | ||
| 1.4.3 Bayberry (Also Known as Arbutus and Chinese Tree Berry): Myrica rubra Sieb. et Zucc. | 20 | ||
| 1.4.4 Camu-camu: Myrciaria dúbia (HBK) McVaugh | 20 | ||
| 1.4.5 Ceylon Gooseberry: Dovyalis hebecarpa (Gardner) Warb. | 21 | ||
| 1.4.6 Corozo: Bactris guineensis (L.) H.E. Moore | 22 | ||
| 1.4.7 Jaboticaba (or Jabuticaba): Myrciaria cauliflora (Mart.) O. Berg. | 22 | ||
| 1.4.8 Jamelão: Syzygium cumini (L.) Skeels (Also Known as Jambolan, Jambul, Black Plum, and Jamblon) | 22 | ||
| 1.4.9 Juçara (or Jussara): Euterpe edulis Mart. | 22 | ||
| 1.4.10 Maqui Berry (Also Known as Maqui or Chilean Blackberry): Aristotelia chilensis (Mol.) Stuntz | 23 | ||
| 1.4.11 Red-jambo (Also Known as Malay Apple, Pomerac, and Mountain-apple): Syzygium malaccense (L.) Merr. and Perry | 24 | ||
| 1.4.12 Roselle: Hibiscus sabdariffa L. | 24 | ||
| 1.5 Concluding Notes | 24 | ||
| References | 24 | ||
| Chapter 2 Chemistry of Anthocyanins | 34 | ||
| 2.1 Introduction | 34 | ||
| 2.2 Multistate System of Chemical Reactions for Anthocyanins: The Reversible System | 35 | ||
| 2.2.1 Chemical Reactions Interconnecting the Multistate Species | 37 | ||
| 2.2.1.1 Calculation of the Rate and Equilibrium Constants | 38 | ||
| 2.2.1.2 Malvidin-3-glucoside | 42 | ||
| 2.3 Self-aggregation of Anthocyanins | 48 | ||
| 2.3.1 Intramolecular Self-aggregation Association in Malvidin-3-O-(6-p-coumaroyl)-glucoside | 53 | ||
| 2.3.2 Intramolecular Self-aggregation Association in the Morning Glory Flower | 54 | ||
| 2.3.3 Metalloanthocyanins | 55 | ||
| 2.4 Deoxyanthocyanins: A Different Kinetic Paradigm | 55 | ||
| 2.4.1 Oaklins | 58 | ||
| 2.5 Chemical Reactivity of Anthocyanins - The Irreversible Reactions | 59 | ||
| 2.5.1 Substituted Anthocyanins in Position 6 and 8 | 60 | ||
| 2.5.2 Pyranoanthocyanins (First Generation) | 62 | ||
| 2.5.2.1 p-Hydroxyphenyl-pyranoanthocyanins | 65 | ||
| 2.5.2.2 Vitisin A | 66 | ||
| 2.5.2.3 Vitisins B | 66 | ||
| 2.5.2.4 Methylpyranoanthocyanin | 66 | ||
| 2.5.2.5 (+)-Cathechin, (-)-Epicathechin, and Catechol Substitution in Ring D | 67 | ||
| 2.5.2.6 Deoxy-pyranoanthocyanins | 69 | ||
| 2.5.3 Pyranoanthocyanins (Second Generation) | 70 | ||
| 2.5.3.1 Vinylpyranoanthocyanins (Portisins) | 70 | ||
| 2.5.3.2 Pyranoanthocyanin Dimers | 71 | ||
| 2.6 Conclusion | 71 | ||
| Acknowledgments | 72 | ||
| References | 72 | ||
| Chapter 3 Extraction of Anthocyanins from Natural Sources - Methods and Commercial Considerations | 77 | ||
| 3.1 Introduction | 77 | ||
| 3.2 Basic Chemistry and Stability of Anthocyanins | 78 | ||
| 3.3 Pretreatment of Natural Materials Before Extraction | 80 | ||
| 3.4 Conventional Extraction Methods | 84 | ||
| 3.4.1 Conventional Solvent Extraction | 84 | ||
| 3.4.1.1 Solvent | 85 | ||
| 3.4.1.2 Addition of Acids | 86 | ||
| 3.4.1.3 Temperature | 87 | ||
| 3.4.2 Solid-phase Extraction | 87 | ||
| 3.5 Modern Green Extraction Methods | 89 | ||
| 3.5.1 Pressurized Liquid Extraction | 90 | ||
| 3.5.2 Supercritical Fluid Extraction | 92 | ||
| 3.5.3 Microwave-assisted Extraction | 93 | ||
| 3.5.4 Ultrasound-assisted Extraction | 94 | ||
| 3.5.5 Pulsed Electric Field Extraction | 95 | ||
| 3.5.6 Counter-current Chromatography | 96 | ||
| 3.5.7 Enzyme-assisted Extraction | 97 | ||
| 3.6 Conclusion | 98 | ||
| References | 99 | ||
| Chapter 4 Extraction of Anthocyanins from Food Processing Waste - Potential and Issues | 106 | ||
| 4.1 Introduction | 106 | ||
| 4.2 Characteristics of Raw Material Prior to Processing | 107 | ||
| 4.3 Extraction of Anthocyanins from Processing Waste | 111 | ||
| 4.3.1 Conventional Approaches | 111 | ||
| 4.3.2 Novel Assisted Approaches | 112 | ||
| 4.4 Application of Anthocyanins from Waste Sources as Food Ingredients | 114 | ||
| 4.5 Regulation of the Use of Anthocyanins as a Food Ingredient in the European Union | 115 | ||
| 4.6 Hurdles to the Application of Anthocyanins from Food Waste Sources in Foods | 117 | ||
| 4.7 Conclusions | 118 | ||
| References | 119 | ||
| Part II Health Benefits and Metabolism | 121 | ||
| Chapter 5 Health Benefits of Anthocyanins | 123 | ||
| 5.1 Introduction | 123 | ||
| 5.2 Neuroprotective Effects of Anthocyanins | 124 | ||
| 5.3 Anticancer Effects of Anthocyanins | 127 | ||
| 5.3.1 In Vitro Studies | 129 | ||
| 5.3.2 In Vivo Studies | 135 | ||
| 5.4 Cardioprotective Effects of Anthocyanins | 137 | ||
| 5.5 Antidiabetic Effects of Anthocyanins | 139 | ||
| 5.6 Ocular Benefits of Anthocyanins | 145 | ||
| 5.7 Future Research | 146 | ||
| 5.8 Conclusions | 147 | ||
| Acknowledgments | 148 | ||
| References | 148 | ||
| Chapter 6 Pharmacokinetics | 159 | ||
| 6.1 Introduction | 159 | ||
| 6.2 Absorption | 160 | ||
| 6.2.1 Structural and Physical Considerations | 160 | ||
| 6.2.2 Transport | 160 | ||
| 6.2.3 Tissue | 161 | ||
| 6.3 Metabolism | 162 | ||
| 6.3.1 Conjugation | 162 | ||
| 6.3.2 Microbial Metabolism | 164 | ||
| 6.4 Distribution | 169 | ||
| 6.4.1 Pharmacokinetics | 169 | ||
| 6.4.2 Microbial Metabolites | 173 | ||
| 6.4.3 Tissue | 175 | ||
| 6.5 Excretion/Elimination | 175 | ||
| 6.5.1 Recovery | 175 | ||
| 6.5.2 Microbial Metabolite | 177 | ||
| 6.6 Summary | 179 | ||
| Abbreviations | 179 | ||
| Acknowledgments | 179 | ||
| References | 180 | ||
| Chapter 7 The Stability and Absorption of Anthocyanins in the Mouth | 186 | ||
| 7.1 Introduction | 186 | ||
| 7.2 Potential Health Benefits of Anthocyanins in the Oral Cavity | 187 | ||
| 7.3 Stability of Anthocyanins in the Oral Cavity | 189 | ||
| 7.3.1 Impact of Anthocyanin Chemical Structure | 190 | ||
| 7.3.2 Effects of pH - Anthocyanin Equilibria | 193 | ||
| 7.3.3 Anthocyanin Stability in Saliva | 196 | ||
| 7.3.3.1 Effects of Salivary Inorganic Compounds | 196 | ||
| 7.3.3.2 Effects of Non-enzymatic Salivary Proteins | 197 | ||
| 7.3.3.3 Effects of Salivary Enzymes | 198 | ||
| 7.3.4 The Role of the Oral Microbiota in Anthocyanin Stability | 201 | ||
| 7.4 Absorption of Anthocyanins in the Oral Cavity | 202 | ||
| 7.4.1 Effects of Route of Exposure on Anthocyanin Absorption | 203 | ||
| 7.4.2 Localization of Anthocyanins in Oral Tissues | 205 | ||
| 7.4.3 Effects of Anthocyanin Structure on Uptake and Absorption | 206 | ||
| 7.5 Metabolism of Anthocyanins in the Oral Cavity | 208 | ||
| 7.5.1 Enzymes Responsible for Metabolism of Anthocyanins in the Oral Cavity | 208 | ||
| 7.5.2 Distribution of Anthocyanin-metabolizing Enzymes in the Oral Cavity | 210 | ||
| 7.5.3 Oral Enterohepatic Recycling of Anthocyanins | 211 | ||
| 7.6 Concluding Remarks | 212 | ||
| References | 212 | ||
| Chapter 8 Role of the Stomach in Anthocyanin Absorption | 216 | ||
| 8.1 Introduction | 216 | ||
| 8.2 Anatomy and Histology of the Stomach | 217 | ||
| 8.3 Physiology of the Stomach | 220 | ||
| 8.3.1 Motility | 221 | ||
| 8.3.2 Hormone Secretion | 221 | ||
| 8.3.3 Acid Secretion | 222 | ||
| 8.3.4 Enzyme Secretion | 224 | ||
| 8.3.5 Water Secretion | 225 | ||
| 8.3.6 Mucus and Bicarbonate Secretion | 226 | ||
| 8.3.7 Intrinsic Factor | 227 | ||
| 8.4 Observations About Gastric Absorption of Drugs and Drug-like Compounds | 227 | ||
| 8.5 Barriers and Breaches to Gastric Absorption | 228 | ||
| 8.5.1 The pH Factor | 228 | ||
| 8.5.2 The Mucus Factor | 229 | ||
| 8.5.3 The Epithelial Factor: Paracellular and Transcellular Transport | 229 | ||
| 8.6 The Case of Gastric Absorption of Dietary Anthocyanins | 232 | ||
| 8.6.1 Pharmacokinetics of Anthocyanins | 232 | ||
| 8.6.2 Chemical Stability of Anthocyanins in the Stomach | 234 | ||
| 8.6.3 Expression of Bilitranslocase in the Stomach Epithelium | 234 | ||
| 8.6.4 Direct Evidence of Gastric Absorption of Anthocyanins In Vivo | 235 | ||
| 8.6.5 Direct Evidence of Gastric Absorption of Anthocyanins In Vitro | 235 | ||
| 8.7 Systematic Scrutiny of the Gastric Absorption of Anthocyanins: Biological Factors vs. Experimental Evidence | 236 | ||
| 8.8 Conclusions | 239 | ||
| Acknowledgments | 239 | ||
| References | 239 | ||
| Part III Controlled Release Systems for Anthocyanins | 247 | ||
| Chapter 9 Encapsulation Techniques for Anthocyanins | 249 | ||
| 9.1 Goals of Encapsulation | 249 | ||
| 9.2 Encapsulation Techniques for Anthocyanins | 250 | ||
| 9.2.1 Spray Drying | 252 | ||
| 9.2.2 Freeze Drying | 256 | ||
| 9.2.3 Gel Formation | 259 | ||
| 9.2.4 Emulsion Systems | 266 | ||
| 9.2.5 Novel Encapsulation Techniques | 270 | ||
| 9.3 Stability of Encapsulated Anthocyanins | 273 | ||
| 9.4 Applications of Encapsulated Anthocyanins | 275 | ||
| 9.5 Conclusion and Future Directions | 276 | ||
| References | 277 | ||
| Chapter 10 Routes of Anthocyanin Delivery and Suitable Systems for Targeted Release | 282 | ||
| 10.1 Introduction | 282 | ||
| 10.2 Routes of Anthocyanin Absorption | 285 | ||
| 10.3 Proposed Systems for Sustained Delivery of Anthocyanins in the Mouth | 286 | ||
| 10.4 Proposed Systems for Targeted Delivery of Anthocyanins in the Stomach | 287 | ||
| 10.4.1 In situ Gelling (or Raft-Forming) Systems | 290 | ||
| 10.4.2 Floating (or Low-density) Systems | 290 | ||
| 10.4.3 Other Platforms | 293 | ||
| 10.5 Proposed Systems for Targeted Delivery of Anthocyanins in the Intestines | 294 | ||
| 10.6 Challenges and Future Prospects | 295 | ||
| 10.7 Conclusions | 296 | ||
| References | 297 | ||
| Part IV Conclusions | 305 | ||
| Chapter 11 Closing Remarks and Future Prospects | 307 | ||
| 11.1 Closing Remarks | 307 | ||
| 11.2 Future Prospects | 309 | ||
| Subject Index | 310 |