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Carotenoids are an essential component of the human diet. Bioactive by nature, they are rich in antioxidants, promote vitamin A activity and lower the development of chronic illnesses. As such they are an area of growing interest to researchers and scientists who are working to design, develop and launch new functional food products, dietary supplements and other nutritional solutions. Carotenoids: Nutrition, Analysis and Technology is an up-to-date overview of the key areas of carotenoids in nutrition, therapy and technology. In the first section, the authors present a functional food…mehr
Carotenoids are an essential component of the human diet. Bioactive by nature, they are rich in antioxidants, promote vitamin A activity and lower the development of chronic illnesses. As such they are an area of growing interest to researchers and scientists who are working to design, develop and launch new functional food products, dietary supplements and other nutritional solutions. Carotenoids: Nutrition, Analysis and Technology is an up-to-date overview of the key areas of carotenoids in nutrition, therapy and technology. In the first section, the authors present a functional food perspective, outlining the therapeutic applications of the bioactive pigments. The second part is dedicated to the spectroscopic analysis of carotenoids, providing in-depth scientific methods and real research findings. In the final section, various technological applications of carotenoids are considered, including biotechnology and future prospects. Written by international experts in the field, this comprehensive book will be of interest to food scientists and researchers, nutritionists and health food companies. It will be of particular use to anyone involved in the spectroscopic analysis of carotenoids and other related bioactives.
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Agnieszka Kaczor is a postgraduate researcher in the Faculty of Chemistry at Jagiellonian University in Krakow, Poland. Her scientific interests concentrate on the application of vibrational spectroscopy and multitechnique imaging to study biological samples. Recently, she has focused on studying changes in cells and tissues upon pathology development with the help of Raman and AFM imaging as well as the application of Raman optical activity to investigate bioactive compounds. Malgorzata Baranska is a professor in the Faculty of Chemistry at Jagiellonian University in Krakow, Poland. She focuses on research of plant and medical bioactive compounds by means of spectroscopic methods, particularly modern Raman techniques (i.e., Raman imaging and Raman optical activity). The new direction of her research is related to lifestyle diseases, their development and methods of curing. This research in various in vitro, ex vivo and in vivo animal models is conducted partly in the Jagiellonian Centre for Experimental Therapeutics (JCET).
Inhaltsangabe
List of Contributors xi 1 Carotenoids: Overview of Nomenclature, Structures, Occurrence, and Functions 1 Agnieszka Kaczor, Malgorzata Baranska, and Krzysztof Czamara 1.1 Introduction 1 1.2 Nomenclature and structures 2 1.3 Occurrence and functions 7 1.3.1 Functions in plants 7 1.3.2 Antioxidants in humans 8 1.3.3 Role in visual and cognitive function 8 1.3.4 Carotenoids in human skin 8 1.3.5 Signaling function 9 1.3.6 Industrial applications 9 1.3.7 Carotenoids of specified properties 9 References 10 Part I Therapy 15 2 The Role of Antioxidants in Prevention of Premature Skin Aging 17 Jürgen Lademann, Maxim Evgen'evich Darvin, Fanny Knorr, Sascha Jung, Leonhard Zastrow, and Martina Claudia Meinke 2.1 Introduction 17 2.2 State of the art 17 2.2.1 Solar radiation and skin aging 17 2.2.2 Carotenoids and the antioxidants of the human skin 18 2.2.3 Factors influencing the antioxidant status of the skin 20 2.2.4 Antioxidants and sun protection 21 2.2.5 Antioxidants and skin aging 22 2.2.6 Investigations into the antioxidant status of high school students 22 2.2.7 Accumulation of antioxidants in human skin by systemic and topical application 23 2.2.8 Ethnic influences on the antioxidant status 24 2.2.9 The antioxidant status in pregnant women and neonates 25 2.3 Summary 26 Conclusions 26 References 27 3 Antitumor Activity of Dietary Carotenoids, and Prospects for Applications in Therapy: Carotenoids and Cancer by Raman Imaging 31 Halina Abramczyk and Jakub Surmacki 3.1 Results 33 3.2 Conclusions 38 3.3 Perspectives 38 References 39 4 Photoprotection and Radiation Protection by Dietary Carotenoids 43 Fritz Boehm, Ruth Edge, Terence George Truscott, and Christian Witt 4.1 Introduction 43 4.2 Carotenoids and singlet oxygen 44 4.2.1 Organic solvents 44 4.2.2 Cell models 46 4.2.3 Cells 47 4.3 Radicals 48 4.3.1 Radical cations 48 4.3.2 Carotenoid-radical adducts 49 4.3.3 Neutral radicals 50 4.3.4 Radical anions 51 4.3.5 The interaction of CARs with the superoxide radical and its protonated conjugated acid 51 4.4 Future prospects and challenges 53 4.5 Conclusion 53 Acknowledgments 54 References 54 5 Macular Carotenoids: Human Health Aspects 59 Aruna Gorusupudi and Paul S. Bernstein 5.1 Introduction 59 5.2 Macular pigment distribution 60 5.3 Human health aspects 61 5.4 Age?]related macular degeneration (AMD) 61 5.5 Macular carotenoid absorption 63 5.6 Stereochemistry and metabolism of macular carotenoids 65 5.7 Measurement of macular carotenoids 67 5.8 Conclusions and perspectives 68 References 68 Part II Spectroscopy 75 6 Vibrational Spectroscopy as a Tool to Investigate Carotenoids 77 Jan Cz. Dobrowolski 6.1 Introduction 77 6.2 Vibrations of carotenoids 77 6.2.1 Geometry 78 6.2.2 Geometrical cis?]trans isomerism 78 6.2.3 Syn?]periplanar (s?]cis) or anti?]periplanar (s?]trans) conformations 79 6.2.4 pi?]electron delocalization 79 6.2.5 The nature, shape, and energy of the electronic ground and excited states 79 6.2.6 Electron affinity, ionization, reduction, and oxidation potentials 80 6.2.7 The nature and shape of molecular vibrations and vibrational coupling patterns 80 6.2.8 The role of methyl groups attached to the polyene chain and the end groups 81 6.3 Recent applications of vibrational spectroscopy to study natural carotenoids 81 6.3.1 Bacteria lichens and algae 83 6.3.2 Corals and pearls 87 6.3.3 Art and archeology 90 6.4 Perspectives 91 Acknowledgments 92 References 92 7 Structural Studies of Carotenoids in Plants, Animals, and Food Products 103 Takashi Maoka 7.1 Introduction 103 7.2 Extraction and pre?]preparation of carotenoids 103 7.3 Chromatography and separation of carotenoids 105 7.3.1 Column chromatography and thin?]layer chromatography 105 7.3.2 High?]performance liquid chromatography 105 7.4 Quantification of carotenoids 106 7.5 Identification and structural elucidation of carotenoids 106 7.5.1 Chemical dramatization 107 7.5.2 UV?]Vis, IR, and Raman spectrometry 107 7.5.3 Mass spectrometry 108 7.5.4 NMR spectrometry 111 7.6 Determination of absolute configuration of carotenoids 120 7.6.1 Circular dichroism (CD) spectroscopy 120 7.6.2 NMR spectrometry using the modified Mosher method 122 7.6.3 Synthetic approach 123 7.6.4 X?]ray crystallography 124 7.6.5 Examples of structural determination of natural carotenoids 124 7.7 Conclusion (future prospects and challenges) 126 Acknowledgments 126 References 127 8 In Situ Studies of Carotenoids in Plants and Animals 131 Malgorzata Baranska, Jan Cz. Dobrowolski, and Grzegorz Zajac 8.1 Introduction 131 8.2 Plants 131 8.3 Animals 134 8.4 Humans 137 8.4.1 Skin 137 8.4.2 Macular pigment 139 8.4.3 Carotenoids in single human cells 140 8.5 Perspectives 142 Acknowledgments 143 References 143 9 Carotenoids in Pigment-Protein Complexes: Relation between Carotenoid Structure and Function 147 Wieslaw I. Gruszecki 9.1 Biological functions of carotenoids 147 9.2 Carotenoids in pigment-protein complexes 149 9.3 Final remarks 154 9.4 Perspectives 155 Acknowledgments 155 References 155 Part III Technology 159 10 Carotenoid Biosynthesis and Regulation in Plants 161 Rafal Baranski and Christopher I. Cazzonelli 10.1 Biosynthetic pathways 161 10.1.1 Occurrence in nature 161 10.1.2 Cellular localization and compartmentalization 162 10.1.3 Pathways to generate isoprenoid precursors for carotenoid biosynthesis 163 10.1.4 The main pathway toward carotenoid biosynthesis 165 10.1.5 Specialty branches of the pathway 169 10.2 Regulation of carotenoid biosynthesis 170 10.2.1 Cross?]talk between and within the carotenoid and MEP pathways 171 10.2.2 Environmental and developmental control 171 10.2.3 Regulation by epigenetic and posttranscriptional mechanisms 172 10.2.4 Carotenoids in plastid biogenesis, differentiation, and control 173 10.2.5 Enzyme localization and metabolon compartmentalization 174 10.2.6 Carotenoid degradation and production of signaling metabolites 175 10.3 Biofortification and health perspectives 178 Acknowledgments 179 References 179 11 Carotenoid Bioavailability from the Food Matrix: Toward Efficient Extraction Procedures 191 Hartwig Schulz 11.1 Introduction 191 11.2 Occurrence of carotenoids in food materials 193 11.3 Bioavailability and bioefficiency of carotenoids 194 11.4 Extraction of carotenoids from various food matrices 197 11.5 Conclusions 210 11.6 Perspectives 211 References 211 12 Carotenoid Production by Bacteria, Microalgae, and Fungi 217 Ralf Martin Schweiggert and Reinhold Carle 12.1 Introduction 217 12.2 Microbial biosynthesis of carotenoids 218 12.3 Carotenoid?]rich microorganisms 223 12.3.1 Microalgae 223 12.3.2 Yeasts and filamentous fungi 225 12.3.3 Bacteria 226 12.4 Selected examples of biotechnological carotenoid production 228 12.4.1 Production of ß?]carotene 228 12.4.2 Production of astaxanthin 230 12.4.3 Production of lycopene 232 12.4.4 Production of lutein and zeaxanthin 233 12.5 Perspectives and conclusions 234 References 235 13 Impact of Stress Factors on Carotenoid Composition, Structures, and Bioavailability in Microbial Sources 241 Agnieszka Kaczor and Marta Z. Pacia 13.1 Introduction 241 13.2 Light 242 13.3 Temperature 246 13.4 Carbon and nitrogen sources 249 13.5 Aerobic versus anaerobic conditions 250 13.6 Inorganic and organic salts 250 13.7 Other chemical agents 253 13.8 pH 253 13.9 Multiple stress factors 254 13.10 Perspectives and conclusions 254 Acknowledgments 255 References 255 14 Syntheses with Carotenoids 261 Hans?]Richard Sliwka and Vassilia Partali 14.1 Introduction 261 14.2 Reaction with double bonds 263 14.2.1 Hydrogenation 263 14.2.2 Halogenation 263 14.2.3 Oxidation 263 14.2.4 Electron transfer from and to carotenoids 264 14.2.5 Iron carbonyl 264 14.2.6 Nitration 265 14.2.7 In?]chain modification 265 14.3 Transformation of substituents 265 14.3.1 .C=O --> .C=C. 265 14.3.2 .CH=O --> CH=S 267 14.3.3 .C=O --> .C=S 268 14.3.4 .C=O --> .C.OH 268 14.3.5 Inversion of .OH 269 14.3.6 .OH --> .F, .Cl, .Br, and .I 269 14.3.7 .OH --> .SR, .SCN, .SH, .N2, .NH2, and .SeR 269 14.3.8 .OH --> .OR 270 14.3.9 .OH --> glycosides 271 14.3.10 Reactions with carotenoid epoxides 271 14.3.11 Reactions with halogen carotenoids 271 14.3.12 Metal complexes with carotenols, carotenals, and carotenones 272 14.4 Preparative derivatization 272 14.5 Syntheses with carotenoid acids and carotenols 272 14.5.1 .COOH --> .COCl 273 14.5.2 .COOH --> COO. M+ 273 14.5.3 .COOH --> COOR 273 14.5.4 .COOR --> .COOH 277 14.5.5 .COOH --> .CONH2 279 14.5.6 .COOH --> .CO.O.OC. (carotenoid anhydrides) 279 14.6 Carotenoid reactions with Au 280 14.7 Valuation and conclusion 281 Acknowledgments 282 References 283 Index 291
List of Contributors xi 1 Carotenoids: Overview of Nomenclature, Structures, Occurrence, and Functions 1 Agnieszka Kaczor, Malgorzata Baranska, and Krzysztof Czamara 1.1 Introduction 1 1.2 Nomenclature and structures 2 1.3 Occurrence and functions 7 1.3.1 Functions in plants 7 1.3.2 Antioxidants in humans 8 1.3.3 Role in visual and cognitive function 8 1.3.4 Carotenoids in human skin 8 1.3.5 Signaling function 9 1.3.6 Industrial applications 9 1.3.7 Carotenoids of specified properties 9 References 10 Part I Therapy 15 2 The Role of Antioxidants in Prevention of Premature Skin Aging 17 Jürgen Lademann, Maxim Evgen'evich Darvin, Fanny Knorr, Sascha Jung, Leonhard Zastrow, and Martina Claudia Meinke 2.1 Introduction 17 2.2 State of the art 17 2.2.1 Solar radiation and skin aging 17 2.2.2 Carotenoids and the antioxidants of the human skin 18 2.2.3 Factors influencing the antioxidant status of the skin 20 2.2.4 Antioxidants and sun protection 21 2.2.5 Antioxidants and skin aging 22 2.2.6 Investigations into the antioxidant status of high school students 22 2.2.7 Accumulation of antioxidants in human skin by systemic and topical application 23 2.2.8 Ethnic influences on the antioxidant status 24 2.2.9 The antioxidant status in pregnant women and neonates 25 2.3 Summary 26 Conclusions 26 References 27 3 Antitumor Activity of Dietary Carotenoids, and Prospects for Applications in Therapy: Carotenoids and Cancer by Raman Imaging 31 Halina Abramczyk and Jakub Surmacki 3.1 Results 33 3.2 Conclusions 38 3.3 Perspectives 38 References 39 4 Photoprotection and Radiation Protection by Dietary Carotenoids 43 Fritz Boehm, Ruth Edge, Terence George Truscott, and Christian Witt 4.1 Introduction 43 4.2 Carotenoids and singlet oxygen 44 4.2.1 Organic solvents 44 4.2.2 Cell models 46 4.2.3 Cells 47 4.3 Radicals 48 4.3.1 Radical cations 48 4.3.2 Carotenoid-radical adducts 49 4.3.3 Neutral radicals 50 4.3.4 Radical anions 51 4.3.5 The interaction of CARs with the superoxide radical and its protonated conjugated acid 51 4.4 Future prospects and challenges 53 4.5 Conclusion 53 Acknowledgments 54 References 54 5 Macular Carotenoids: Human Health Aspects 59 Aruna Gorusupudi and Paul S. Bernstein 5.1 Introduction 59 5.2 Macular pigment distribution 60 5.3 Human health aspects 61 5.4 Age?]related macular degeneration (AMD) 61 5.5 Macular carotenoid absorption 63 5.6 Stereochemistry and metabolism of macular carotenoids 65 5.7 Measurement of macular carotenoids 67 5.8 Conclusions and perspectives 68 References 68 Part II Spectroscopy 75 6 Vibrational Spectroscopy as a Tool to Investigate Carotenoids 77 Jan Cz. Dobrowolski 6.1 Introduction 77 6.2 Vibrations of carotenoids 77 6.2.1 Geometry 78 6.2.2 Geometrical cis?]trans isomerism 78 6.2.3 Syn?]periplanar (s?]cis) or anti?]periplanar (s?]trans) conformations 79 6.2.4 pi?]electron delocalization 79 6.2.5 The nature, shape, and energy of the electronic ground and excited states 79 6.2.6 Electron affinity, ionization, reduction, and oxidation potentials 80 6.2.7 The nature and shape of molecular vibrations and vibrational coupling patterns 80 6.2.8 The role of methyl groups attached to the polyene chain and the end groups 81 6.3 Recent applications of vibrational spectroscopy to study natural carotenoids 81 6.3.1 Bacteria lichens and algae 83 6.3.2 Corals and pearls 87 6.3.3 Art and archeology 90 6.4 Perspectives 91 Acknowledgments 92 References 92 7 Structural Studies of Carotenoids in Plants, Animals, and Food Products 103 Takashi Maoka 7.1 Introduction 103 7.2 Extraction and pre?]preparation of carotenoids 103 7.3 Chromatography and separation of carotenoids 105 7.3.1 Column chromatography and thin?]layer chromatography 105 7.3.2 High?]performance liquid chromatography 105 7.4 Quantification of carotenoids 106 7.5 Identification and structural elucidation of carotenoids 106 7.5.1 Chemical dramatization 107 7.5.2 UV?]Vis, IR, and Raman spectrometry 107 7.5.3 Mass spectrometry 108 7.5.4 NMR spectrometry 111 7.6 Determination of absolute configuration of carotenoids 120 7.6.1 Circular dichroism (CD) spectroscopy 120 7.6.2 NMR spectrometry using the modified Mosher method 122 7.6.3 Synthetic approach 123 7.6.4 X?]ray crystallography 124 7.6.5 Examples of structural determination of natural carotenoids 124 7.7 Conclusion (future prospects and challenges) 126 Acknowledgments 126 References 127 8 In Situ Studies of Carotenoids in Plants and Animals 131 Malgorzata Baranska, Jan Cz. Dobrowolski, and Grzegorz Zajac 8.1 Introduction 131 8.2 Plants 131 8.3 Animals 134 8.4 Humans 137 8.4.1 Skin 137 8.4.2 Macular pigment 139 8.4.3 Carotenoids in single human cells 140 8.5 Perspectives 142 Acknowledgments 143 References 143 9 Carotenoids in Pigment-Protein Complexes: Relation between Carotenoid Structure and Function 147 Wieslaw I. Gruszecki 9.1 Biological functions of carotenoids 147 9.2 Carotenoids in pigment-protein complexes 149 9.3 Final remarks 154 9.4 Perspectives 155 Acknowledgments 155 References 155 Part III Technology 159 10 Carotenoid Biosynthesis and Regulation in Plants 161 Rafal Baranski and Christopher I. Cazzonelli 10.1 Biosynthetic pathways 161 10.1.1 Occurrence in nature 161 10.1.2 Cellular localization and compartmentalization 162 10.1.3 Pathways to generate isoprenoid precursors for carotenoid biosynthesis 163 10.1.4 The main pathway toward carotenoid biosynthesis 165 10.1.5 Specialty branches of the pathway 169 10.2 Regulation of carotenoid biosynthesis 170 10.2.1 Cross?]talk between and within the carotenoid and MEP pathways 171 10.2.2 Environmental and developmental control 171 10.2.3 Regulation by epigenetic and posttranscriptional mechanisms 172 10.2.4 Carotenoids in plastid biogenesis, differentiation, and control 173 10.2.5 Enzyme localization and metabolon compartmentalization 174 10.2.6 Carotenoid degradation and production of signaling metabolites 175 10.3 Biofortification and health perspectives 178 Acknowledgments 179 References 179 11 Carotenoid Bioavailability from the Food Matrix: Toward Efficient Extraction Procedures 191 Hartwig Schulz 11.1 Introduction 191 11.2 Occurrence of carotenoids in food materials 193 11.3 Bioavailability and bioefficiency of carotenoids 194 11.4 Extraction of carotenoids from various food matrices 197 11.5 Conclusions 210 11.6 Perspectives 211 References 211 12 Carotenoid Production by Bacteria, Microalgae, and Fungi 217 Ralf Martin Schweiggert and Reinhold Carle 12.1 Introduction 217 12.2 Microbial biosynthesis of carotenoids 218 12.3 Carotenoid?]rich microorganisms 223 12.3.1 Microalgae 223 12.3.2 Yeasts and filamentous fungi 225 12.3.3 Bacteria 226 12.4 Selected examples of biotechnological carotenoid production 228 12.4.1 Production of ß?]carotene 228 12.4.2 Production of astaxanthin 230 12.4.3 Production of lycopene 232 12.4.4 Production of lutein and zeaxanthin 233 12.5 Perspectives and conclusions 234 References 235 13 Impact of Stress Factors on Carotenoid Composition, Structures, and Bioavailability in Microbial Sources 241 Agnieszka Kaczor and Marta Z. Pacia 13.1 Introduction 241 13.2 Light 242 13.3 Temperature 246 13.4 Carbon and nitrogen sources 249 13.5 Aerobic versus anaerobic conditions 250 13.6 Inorganic and organic salts 250 13.7 Other chemical agents 253 13.8 pH 253 13.9 Multiple stress factors 254 13.10 Perspectives and conclusions 254 Acknowledgments 255 References 255 14 Syntheses with Carotenoids 261 Hans?]Richard Sliwka and Vassilia Partali 14.1 Introduction 261 14.2 Reaction with double bonds 263 14.2.1 Hydrogenation 263 14.2.2 Halogenation 263 14.2.3 Oxidation 263 14.2.4 Electron transfer from and to carotenoids 264 14.2.5 Iron carbonyl 264 14.2.6 Nitration 265 14.2.7 In?]chain modification 265 14.3 Transformation of substituents 265 14.3.1 .C=O --> .C=C. 265 14.3.2 .CH=O --> CH=S 267 14.3.3 .C=O --> .C=S 268 14.3.4 .C=O --> .C.OH 268 14.3.5 Inversion of .OH 269 14.3.6 .OH --> .F, .Cl, .Br, and .I 269 14.3.7 .OH --> .SR, .SCN, .SH, .N2, .NH2, and .SeR 269 14.3.8 .OH --> .OR 270 14.3.9 .OH --> glycosides 271 14.3.10 Reactions with carotenoid epoxides 271 14.3.11 Reactions with halogen carotenoids 271 14.3.12 Metal complexes with carotenols, carotenals, and carotenones 272 14.4 Preparative derivatization 272 14.5 Syntheses with carotenoid acids and carotenols 272 14.5.1 .COOH --> .COCl 273 14.5.2 .COOH --> COO. M+ 273 14.5.3 .COOH --> COOR 273 14.5.4 .COOR --> .COOH 277 14.5.5 .COOH --> .CONH2 279 14.5.6 .COOH --> .CO.O.OC. (carotenoid anhydrides) 279 14.6 Carotenoid reactions with Au 280 14.7 Valuation and conclusion 281 Acknowledgments 282 References 283 Index 291
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