Carotenoid Esters in Foods, Carotenoid Esters in Foods: Physical, Chemical and Biological Properties by Mercadante, Adriana Z. -- Read -- Imperial Library of Trantor

Index

Cover HalfTitle Title Copyright Series Editor Contents Preface Part I Physical and Chemical Properties of Carotenoids Chapter 1 Structures, Nomenclature and General Chemistry of Carotenoids and Their Esters 3

1.1 Introduction 1.2 Fatty Acids

1.2.1 Occurrence in Nature 1.2.2 Chemical Structure 1.2.3 Nomenclature 1.2.4 Physical–Chemical Properties 1.2.5 Overview of Biosynthesis 1.2.6 Overview of Actions

1.3 Isoprenoids 1.4 Carotenoids

1.4.1 Occurrence in Nature 1.4.2 Chemical Structure 1.4.3 Nomenclature 1.4.4 General Properties and Relation to Some Actions

1.5 Association of Carotenoids with Other Molecules

1.5.1 Carotenoid Glucosides 1.5.2 Carotenoproteins 1.5.3 Carotenoid Sulphates 1.5.4 Carotenoid Acyl Esters 1.5.5 Impact of Association with Other Molecules on the Properties of Carotenoids

References

Chapter 2 Carotenoid Assembly in Fruits and Vegetables 51

2.1 Introduction 2.2 Plastid Morphology During Fruit and Vegetable Development and Ripening 2.3 Forms of Carotenoid Deposition in Plastids 2.4 Chemical Structures of Carotenoids and Their Locations within Plastidal Structures 2.5 Carotenoid Ester Deposition in Selected Plant Material

2.5.1 Mamey Sapote (Pouteria sapota [Jacq.] H.E. Moore & Stearn) 2.5.2 Goji (Lycium barbarum L.) 2.5.3 Papaya (Carica papaya L.) 2.5.4 Mango (Mangifera indica L.)

2.6 Hypotheses on the Biological Importance of Carotenoid Esterification in Plants References

Chapter 3 Chemical Synthesis of Carotenoid Esters 68

3.1 Introduction 3.2 Ester Synthesis for Purification and Structure Elucidation Studies 3.3 Synthesis of Esters to Enhance Stability and Bioavailability

3.3.1 Carotenoid Esters of Fatty Acids, Hydroxy Acids and Bifunctional Acids 3.3.2 Polymeric Esters

3.4 Amphipathic Carotenoid Esters

3.4.1 Synthesis of Ionic (Charged) Carotenoid Esters 3.4.2 Non-charged Hydrophilic Esters

3.5 Synthesis of Bifunctional Carotenoid Esters

3.5.1 Combination with Other Antioxidants 3.5.2 Combination with Porphyrins

3.6 Conclusions Acknowledgements References

Part II Carotenoid Biosynthesis and Occurrence of Carotenoid Esters Chapter 4 General Overview of Carotenoid Biosynthesis 111

4.1 Introduction 4.2 Carotenoids and Isoprenoid Biosynthesis

4.2.1 The Isoprenoid Pathway 4.2.2 Stages of Carotenoid Biosynthesis

4.3 Origin of the Isoprene Unit

4.3.1 The Acetate–Mevalonate Pathway 4.3.2 Conversion of Mevalonate into Isopentenyl Diphosphate 4.3.3 The Mevalonate-independent Pathway to IDP

4.4 Formation of Geranylgeranyl Diphosphate 4.5 Formation of Phytoene 4.6 Desaturation 4.7 Cyclisation 4.8 Hydroxylation

4.8.1 Hydroxylation at C(3) 4.8.2 Introduction of Hydroxy and Keto Groups at Other Positions

4.9 Later Reactions

4.9.1 Epoxidation 4.9.2 Formation of Other End Groups 4.9.3 Esterification

4.10 Carotenoid Breakdown Products

4.10.1 Apocarotenoids 4.10.2 Carotenoid Cleavage Enzymes 4.10.3 Saffron and Bixin

4.11 Regulation in Higher Plants

4.11.1 Environmental, Nutritional and Developmental Factors

4.12 Regulation in Algae 4.13 Enzymes 4.14 Conclusions References

Chapter 5 Biosynthesis and Esterification of Carotenoids During Fruit Ripening 137

5.1 Fruit Classification Regarding Carotenoid Composition and Occurrence of Carotenoid Esters 5.2 Main Pattern of Changes in Carotenoid Composition and Esterification During Fruit Ripening 5.3 Carotenoid Pathway in Fruits and Regulation During Ripening

5.3.1 Regulation of Carotenoid Accumulation in Fruit 5.3.2 Localisation of Carotenoid Ester Biosynthesis

5.4 Conclusion Acknowledgements References

Chapter 6 Occurrence and Metabolism of Carotenoid Esters in Marine Organisms 160

6.1 Introduction

6.1.1 Sources of Carotenoids in Food and Food Chains 6.1.2 Isolation and Analysis

6.2 Carotenoids and Esters in Algae

6.2.1 Long-chain Acyl Esters 6.2.2 Acetate Esters 6.2.3 Esters of C(19) Hydroxy Carotenoids

6.3 Sulphate Esters in Bacteria 6.4 Carotenoid Esters in Marine Animals

6.4.1 Carotenoid Esters in Fish 6.4.2 Carotenoid Esters in Invertebrate Animals

6.5 Conclusions References

Chapter 7 Occurrence of Carotenoid Esters in Foods 182

7.1 Introduction 7.2 Occurrence of Xanthophyll Esters in Food

7.2.1 Fruits and Vegetables 7.2.2 Wheat (Triticum spp.) and Related Cereals 7.2.3 Flowers 7.2.4 Animals 7.2.5 Human Milk

Acknowledgements References

Part III Analytical Methods for Determination of Carotenoid Esters Chapter 8 Extraction and Cleanup of Xanthophyll Esters 287

8.1 Introduction 8.2 Extraction of Carotenoids and Carotenoid Esters

8.2.1 Liquid Extraction at Atmospheric Pressure 8.2.2 UAE and MAE 8.2.3 PEF-assisted Extraction 8.2.4 Accelerated Solvent Extraction 8.2.5 Supercritical Fluid Extraction 8.2.6 Enzyme-assisted Extraction 8.2.7 Extraction Using Green Solvents

8.3 Cleanup of Carotenoid Extracts for Carotenoid Ester Analysis 8.4 Conclusion Acknowledgements References

Chapter 9 Separation 304

9.1 Introduction 9.2 Separation of Carotenoid Esters by 1D Liquid Chromatography in Food Matrices 9.3 Separation of Carotenoid Esters by 2D Chromatography in Food Matrices

9.3.1 Carotenoid Ester Separation by Comprehensive Liquid Chromatography 9.3.2 Carotenoid Ester Separation by Comprehensive Supercritical Fluid Chromatography × Liquid Chromatography 9.3.3 Carotenoid Ester Separation by Offline Multidimensional Chromatography

9.4 Carotenoid Ester Separation by 1D Supercritical Fluid Chromatography in Food Matrices References

Chapter 10 Identification of Carotenoids and Carotenoid Esters 322

10.1 Introduction 10.2 UV/Vis Spectrophotometry

10.2.1 Relationship Between Chemical Structure and UV/Vis Characteristics 10.2.2 Effect of Solvents

10.3 Mass Spectrometry

10.3.1 Acquisition of Mass Data 10.3.2 Identification by APCI(+)

10.4 Conclusions Acknowledgements References

Chapter 11 Quantification and Method Validation 351

11.1 Introduction 11.2 Sampling and Sample Preparation 11.3 Quantification by LC-UV/Vis Detector

11.3.1 Percentage of Area Method 11.3.2 External Standard Method 11.3.3 Internal Standard Method

11.4 Quantification by Liquid Chromatography–Mass Spectrometry 11.5 Method Validation

11.5.1 Selectivity 11.5.2 Trueness and Accuracy 11.5.3 Precision 11.5.4 Limits of Detection and Quantification 11.5.5 Linearity 11.5.6 Robustness

11.6 Final Remarks Acknowledgements References

Part IV Dietary Intake, Digestion, Absorption and Metabolism of Carotenoids and their Esters Chapter 12 Dietary Intake of Carotenoids: Nutritional Status Assessment and the Importance of Considering Free and Ester Forms in Foods 375

12.1 Introduction 12.2 Assessment of Carotenoid Dietary Intake

12.2.1 Assessment Methods Used in Populations and Individuals 12.2.2 Dietary Questionnaires 12.2.3 Food Intake and Measurement of Carotenoid Intake

12.3 Dietary Carotenoid Intake 12.4 Interpretation of Dietary Carotenoid Intake 12.5 Conclusions References

Chapter 13 Bioavailability and Metabolism of Carotenoid Esters 390

13.1 Introduction 13.2 Digestion and Absorption of Carotenoid Esters and Their Metabolites

13.2.1 Bioavailability of Free vs. Esterified Xanthophylls 13.2.2 Bioaccessibility of Xanthophyll Esters 13.2.3 Intestinal Uptake, Metabolism and Absorption of Xanthophylls

13.3 Are Xanthophylls Acylated in Human Tissues? 13.4 Final Remarks Acknowledgements References

Chapter 14 In Vitro Digestion Protocols: The Benchmark for Estimation of In Vivo Data 421

14.1 The Application of Good Practices in the Use of the Term ‘Bioavailability’

14.1.1 The Need for Splitting the Term ‘Bioavailability’ into ‘Bioaccessibility’ and ‘Bioactivity’: A Practicable Achievement vs. a Paramount Effort 14.1.2 Applications of the Bioaccessibility Concept in Food and Nutrition Science

14.2 In Vitro Digestion Protocols: The Imitation Game

14.2.1 Key Developments in the Design of In Vitro Digestion Protocols 14.2.2 Digestion of Lipophilic Compounds or How to Cross the Water Barrier 14.2.3 Methods Applied to Measure the Micellarisation of Carotenoids: A Practical Approach 14.2.4 The Direction of the Magnitude of In Vitro Digestion Protocols

14.3 Conclusions Acknowledgements References

Part V Final Remarks Chapter 15 Carotenoid Esters: Opening New Perspectives and Trends 461

References

Subject Index

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