Food Oligosaccharides Production, Analysis and Bioactivity

A growing awareness of the relationship between diet and health  has led to an increasing demand for food
products that support health beyond simply providing basic nutrition. Digestive
health is the largest segment of the burgeoning functional food market worldwide. Incorporation of bioactive
oligosaccharides into foods can yield health benefits in the gastrointestinal
tract and other parts of the body that are linked via the immune system.
Because oligosaccharides can be added to a wide variety of foodstuffs, there is
much interest within the food industry in incorporating these functional
ingredients into healthy food products. Moreover, other areas such as
pharmaceuticals, bioenergy and environmental science can exploit the
physicochemical and physiological properties of bioactive oligosaccharides too.
There is therefore a considerable demand for a concentrated source of
information on the development and characterization of new oligosaccharides
with novel and/or improved bioactivities.

Food Oligosaccharides: Production, Analysis and Bioactivityis a comprehensive reference on the
naturally occurring and synthesised oligosaccharides, which will enable food
professionals to select and use these components in their products. It is
divided into three sections: (i) Production and bioactivity of
oligosaccharides, (ii) Analysis and (iii) Prebiotics in Food Formulation. The
book addresses classical and advanced techniques to structurally characterize and
quantitatively analyse food bioactive oligosaccharides. It also looks at practical
issues faced by food industry professionals seeking to incorporate prebiotic
oligosaccharides into food products, including the effects of processing on
prebiotic bioavailability. This book is essential reading for food researchers
and professionals, nutritionists and product developers working in the food
industry, and students of Food Science with an interest in functional foods.

Dr F. Javier Moreno, Institute of Food Science Research, CIAL (CSIC-UAM), Madrid, Spain

Dr María Luz Sanz, Institute of General Organic Chemistry, IQOG (CSIC), Madrid, Spain

Contributors, xiv

Preface, xix

Part I Production and Bioactivity of Oligosaccharides

Part I.I Naturally Occurring Oligosaccharides

1 Bioactivity of Human Milk Oligosaccharides, 5
Clemens Kunz, Sabine Kuntz, and Silvia Rudloff

1.1 Introduction, 5

1.2 Structural uniqueness of human milk oligosaccharides, 5

1.3 Human milk oligosaccharides and their functions in the gastrointestinal tract, 8

1.4 Human milk oligosaccharides and systemic effects, 15

1.5 Human milk oligosaccharides and studies in animals and humans, 15

1.6 Conclusion and perspective, 16

Acknowledgment, 17

References, 17

2 Production and Bioactivity of Bovine Milk Oligosaccharides, 21
David C. Dallas, Mickael Meyrand, and Daniela Barile

2.1 Introduction, 21

2.2 Bovine milk oligosaccharides’ composition, 22

2.3 Bovine milk oligosaccharides’ concentration, 27

2.4 Resistance to digestion, 27

2.5 Oligosaccharides’ biological activities, 28

2.6 Isolation approaches, 30

2.7 Conclusion, 31

Acknowledgments, 31

References, 31

3 Production and Bioactivity of Oligosaccharides in Plant Foods, 35
Cristina Martínez-Villaluenga and Juana Frías

3.1 Introduction, 35

3.2 Chemical structure and natural occurrence of oligosaccharides in plant foods, 35

3.3 Production of naturally occurring plant oligosaccharides, 40

3.4 Scientific evidence on the bioefficacy of plant oligosaccharides and mechanisms of action, 43

3.5 Conclusions and future perspectives, 48

References, 48

4 Production and Bioactivity of Oligosaccharides from Chicory Roots, 55
Matthias Moser, Arnaud Agemans, and Wim Caers

4.1 Production of oligosaccharides from chicory roots, 55

4.2 Bioactivity of oligosaccharides from chicory roots, 60

4.3 Future trends, 68

4.4 Conclusions, 69

References, 69

5 Production and Bioactivity of Pectic Oligosaccharides from Fruit and Vegetable Biomass, 76
Jesper Holck, Arland T. Hotchkiss, Jr., Anne S. Meyer, Jørn D. Mikkelsen, and Robert A. Rastall

5.1 Production of pectic oligosaccharides, 76

5.2 Bioactivity of pectic oligosaccharides, 79

5.3 Conclusions, 83

References, 83

6 Production and Bioactivity of Oligosaccharides from Biomass Hemicelluloses, 88
Patricia Gullón, Beatriz Gullón, María Jesus Gonzalez-Munoz, Jose Luis Alonso, and Juan Carlos Parajo

6.1 Hemicelluloses: general aspects, 88

6.2 Manufacture of oligosaccharides from hemicellulosic polymers, 89

6.3 Properties of hemicellulose-derived oligosaccharides, 93

6.4 Conclusion, 99

References, 99

7 Starch Hydrolysis Products with Physiological Activity in Humans, 107
Juscelino Tovar and Ana Rascon

7.1 Introduction, 107

7.2 Starch degradation may yield minor saccharides with physiological activity, 107

7.3 Physiological activity of starch hydrolysis products, 112

7.4 Concluding remarks, 115

References, 115

8 Biosynthesis and Bioactivity of Exopolysaccharides Produced by Probiotic Bacteria, 118
Patricia Ruas-Madiedo

8.1 Bacterial exopolysaccharides, 118

8.2 Biosynthesis of exopolysaccharides in Lactobacillus and Bifidobacterium, 120

8.3 Production and purification of exopolysaccharides, 121

8.4 Bioactivity of exopolysaccharides from probiotics, 124

8.5 Concluding remark and future trends, 128

Acknowledgments, 128

References, 128

Part I.II Non-Naturally Occurring Oligosaccharides

9 Production and Bioactivity of Oligosaccharides Derived from Lactose, 137
Mar Villamiel, Antonia Montilla, Agustýn Olano, and Nieves Corzo

9.1 Introduction, 137

9.2 Mono- and disaccharides, 137

9.3 Lactosucrose, 145

9.4 Galactooligosaccharides, 146

9.5 Other oligosaccharides, 154

9.6 Purification of carbohydrates derived from lactose, 156

9.7 Conclusions, 157

Acknowledgments, 157

References, 157

10 Production and Bioactivity of Glucooligosaccharides and Glucosides Synthesized using Glucansucrases, 168
Young-Min Kim, Hee-Kyoung Kang, Young-Hwan Moon, Thi Thanh Hanh Nguyen, Donal F. Day, and Doman Kim

10.1 Glucooligosaccharides from lactic acid bacteria, 168

10.2 Glucan and glucooligosaccharides synthesis by glucansucrases, 169

10.3 Production of glucooligosaccharides, 171

10.4 Bioactivities of glucan and glucooligosaccharides, 174

10.5 (Oligo)glucosides synthesized by glucansucrases and their functionalities, 177

10.6 Conclusions, 178

Acknowledgments, 178

References, 178

11 Production and Bioactivity of Fructan-Type Oligosaccharides, 184
Javier Arrizon, Judith E. Urias-Silvas, Georgina Sandoval, N. Alejandra Mancilla-Margalli, Anne C. Gschaedler, Sandrine Morel, and Pierre Monsan

11.1 Introduction, 184

11.2 Enzymatic synthesis, 186

11.3 Functional properties of fructan-type oligosaccharides, 193

11.4 Conclusions, 196

Acknowledgments, 196

References, 196

12 Application of Immobilized Enzymes for the Synthesis of Bioactive Fructooligosaccharides, 200
Francisco J. Plou, Lucia Fernandez-Arrojo, Paloma Santos-Moriano, and Antonio O. Ballesteros

12.1 Enzyme immobilization, 200

12.2 Immobilized biocatalysts for the production of fructooligosaccharides, 202

12.3 Production of fructooligosaccharides with a covalently immobilized fructosyltransferase, 204

12.4 Production of fructooligosaccharides with alginate-entrapped fructosyltransferases, 207

12.5 Conclusions and future trends, 212

Acknowledgments, 212

References, 213

Part I.III Assessment of Bioactivity

13 In Vitro Assessment of the Bioactivity of Food Oligosaccharides, 219
Koen Venema

13.1 Introduction, 219

13.2 Gut microbiota, 220

13.3 Interaction with the host, 221

13.4 In vitro fermentation models of the gut to study bioactivity of oligosaccharides, 221

13.5 Applications of in vitro fermentation models to study the effect of oligosaccharides on the gut microbiome, 226

13.6 Mechanistic studies using 13C-labeled oligosaccharides and fibers, 227

13.7 In vitro cell culture systems, 230

13.8 Conclusions, 231

13.9 Future perspectives, 231

Acknowledgments, 233

References, 233

14 In Vivo Assessment of the Bioactivity of Food Oligosaccharides, 238
Alfonso Clemente

14.1 The prebiotic concept, 238

14.2 In vivo assessment of dietary oligosaccharides as prebiotics, 240

14.3 Concluding remarks, 249

Acknowledgments, 249

References, 249

Part II Analysis

15 Fractionation of Food Bioactive Oligosaccharides, 257
F. Javier Moreno, Cipriano Carrero-Carralero, Oswaldo Hernandez-Hern´andez, and M. Luz Sanz

15.1 Introduction, 257

15.2 Membrane techniques, 258

15.3 Chromatographic techniques, 267

15.4 Fractionation techniques using solvents, 272

15.5 Microbiological and enzymatic treatments, 275

15.6 Conclusions, 276

Acknowledgments, 277

References, 277

16 Classical Methods for Food Carbohydrate Analysis, 284
Qingbin Guo, Steve W. Cui, and Ji Kang

16.1 Introduction, 284

16.2 Sample preparation and purification, 284

16.3 Classical methods for total sugar analysis, 285

16.4 Classical methods for monosaccharide determination, 289

16.5 Classical methods for structure characterization of polysaccharides, 291

16.6 Some physical methods for carbohydrate analysis, 294

16.7 Classical methods for dietary fiber analysis, 294

16.8 Conclusions, 296

References, 297

17 Infrared Spectroscopic Analysis of Food Carbohydrates, 300
Mikihito Kanou, Atsushi Hashimoto, and Takaharu Kameoka

17.1 Introduction, 300

17.2 Monosaccharides, 301

17.3 Oligosaccharides, 309

17.4 Applications, 312

17.5 Concluding remarks, 317

References, 318

18 Structural Analysis of Carbohydrates by Nuclear Magnetic Resonance Spectroscopy and Molecular Simulations: Application to Human Milk Oligosaccharides, 320
Arnold Maliniak and Goran Widmalm

18.1 Introduction, 320

18.2 Nuclear magnetic resonance spectroscopy, 323

18.3 Molecular dynamics computer simulations, 335

18.4 Three-dimensional structures of human milk oligosaccharides, 336

18.5 Concluding remarks, 341

Acknowledgments, 341

References, 341

19 Analysis of Food Bioactive Oligosaccharides by Thin-Layer Chromatography, 350
Katarýna Reiffova

19.1 Introduction, 350

19.2 Thin-layer chromatography, 351

19.3 Thin-layer chromatography analysis of food bioactive oligosaccharides, 353

19.4 Conclusions, 366

References, 366

20 Gas Chromatographic Analysis of Food Bioactive Oligosaccharides, 370
Ana Cristina Soria, Sonia Rodrýguez-Sanchez, Jesus Sanz, and Isabel Martýnez-Castro

20.1 Introduction, 370

20.2 Sample preparation, 371

20.3 Instrumentation, 382

20.4 Advanced analysis by comprehensive two-dimensional gas chromatography (GC×GC), 392

20.5 Conclusions, 392

Acknowledgments, 394

References, 394

21 Analysis of Bioactive Food-Sourced Oligosaccharides by High-Performance Liquid Chromatography, 399
Jonathan A. Lane and Rita M. Hickey

21.1 Introduction, 399

21.2 Derivatization of oligosaccharides, 400

21.3 High-performance liquid chromatography analysis of bioactive food sourced oligosaccharides, 402

21.4 Application of high-performance liquid chromatography for the separation of bioactive food sourced oligosaccharides, 407

21.5 Novel analytical methods, 412

21.6 Conclusion, 414

Acknowledgments, 415

References, 415

22 Capillary Electrophoresis and Related Techniques for the Analysis of Bioactive Oligosaccharides, 421
Yu-ki Matsuno, Kazuaki Kakehi, and Akihiko Kameyama

22.1 Introduction, 421

22.2 Capillary electrophoresis analysis of functional oligosaccharides, 423

22.3 Capillary electrophoresis analysis of glycosaminoglycan-derived oligosaccharides, 428

22.4 Capillary electrophoresis analysis of oligosaccharides derived from glycoproteins, 431

22.5 Conclusions, 434

References, 435

23 Mass Spectrometric Analysis of Food Bioactive Oligosaccharides, 439
Oswaldo Hernandez-Hernandez and Peter Roepstorff

23.1 Introduction, 439

23.2 Instrumentation for mass spectrometric analysis of oligosaccharides, 439

23.3 Fragmentation techniques, processes and nomenclature, 442

23.4 Applications to analysis of food bioactive oligosaccharides, 445

23.5 Strategies, challenges, and conclusion, 450

References, 450

Part III Prebiotics in Food Formulation

24 Nutritional and Technological Benefits of Inulin-Type Oligosaccharides, 457
Matthias Moser and Rudy Wouters

24.1 Introduction, 457

24.2 Nutritional aspects of chicory inulin and oligofructose, 457

24.3 Technical properties of chicory inulin and oligofructose, 458

24.4 Technical functionality in food applications, 461

24.5 Conclusions, 468

References, 468

25 Industrial Applications of Galactooligosaccharides, 470
Ellen van Leusen, Erik Torringa, Paul Groenink, Pieter Kortleve, Renske Geene, Margriet Schoterman, and Bert Klarenbeek

25.1 Introduction, 470

25.2 Global market development for galactooligosaccharides, 470

25.3 Nutritional benefits of galactooligosaccharides for infants and young children, 473

25.4 Legislative aspects and safety of galactooligosaccharides, 477

25.5 Galactooligosaccharide products, 479

25.6 Applications of galactooligosaccharides, 483

25.7 Stability of galactooligosaccharides, 485

25.8 Concluding remarks and future developments, 487

References, 487

26 Successful Product Launch: Combining Industrial Technologies with Adapted Health Ingredients, 492
Pascal Ronfard

26.1 Developing new foods: the health dimension, 492

26.2 A global approach to successful food conception, applied to the case of digestive health, 493

26.3 The ingredients and the formulation: practical aspects of the incorporation of nondigestible oligosaccharides, 503

26.4 Elaborating new food products with nondigestible oligosaccharides, 507

26.5 What are the key success factors? Synthesis and comments from an expert chef, 518

26.6 Conclusion, 520

References, 520

Epilogue: Concluding Thoughts on Food Bioactive Oligosaccharides, 523

Index, 527

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