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Recent Advances in Polyphenol Research, Volume 6


Recent Advances in Polyphenol Research, Volume 6


1. Aufl.

von: Heidi Halbwirth, Karl Stich, Véronique Cheynier, Stéphane Quideau

189,99 €

Verlag: Wiley-Blackwell
Format: EPUB
Veröffentl.: 11.01.2019
ISBN/EAN: 9781119427919
Sprache: englisch
Anzahl Seiten: 432

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Beschreibungen

<p>Plant polyphenols are secondary metabolites that constitute one of the most common and widespread groups of natural products. They are crucial constituents of a large and diverse range of biological functions and processes, and provide many benefits to both plants and humans. Many polyphenols, from their structurally simplest representatives to their oligo/polymeric versions, are notably known as phytoestrogens, plant pigments, potent antioxidants, and protein interacting agents.</p> <p>This sixth volume of the highly regarded <i>Recent Advances in Polyphenol Research </i>series is edited by Heidi Halbwirth, Karl Stich, Véronique Cheynier and Stéphane Quideau, and is a continuance of the series’ tradition of compiling a cornucopia of cutting-edge chapters, written by some of the leading experts in their respective fields of polyphenol sciences. Highlighted herein are some of the most recent and pertinent developments in polyphenol research, covering such major areas as:</p> <ul> <li>Chemistry and physicochemistry</li> <li>Biosynthesis, genetics & metabolic engineering</li> <li>Roles in plants and ecosystems</li> <li>Food, nutrition & health</li> <li>Applied polyphenols</li> </ul> <p>This book is a distillation of the most current information, and as such, will surely prove an invaluable source for chemists, biochemists, plant scientists, pharmacognosists and pharmacologists, biologists, ecologists, food scientists and nutritionists.  </p>
<p>Contributors xiii</p> <p>Preface xvii</p> <p>Acknowledgements xxi</p> <p><b>1 The Lignans: A Family of Biologically Active Polyphenolic Secondary Metabolites 1<br /></b><i>Anna K.F. Albertson and Jean‐Philip Lumb</i></p> <p>1.1 Introduction 1</p> <p>1.2 Biosynthesis of Lignans 3</p> <p>1.3 Synthetic Approaches to Lignans and Derivatives 7</p> <p>1.4 Conclusion 60</p> <p>References 65</p> <p><b>2 Anthocyanin Accumulation is Controlled by Layers of Repression 71<br /></b><i>Andrew C. Allan, Kathy E. Schwinn, and Richard V. Espley</i></p> <p>2.1 Introduction 71</p> <p>2.2 MYBs and bHLHs Directly Activate Anthocyanin Production 72</p> <p>2.3 Exciting Phenotypes in Horticulture are often caused by Variations in the Expression of Key MYBs 73</p> <p>2.4 Is There a Cost to the Plant of over accumulation of Anthocyanins? 74</p> <p>2.5 Controlling Anthocyanin Levels 75</p> <p>2.6 The MYB Activator is Degraded at Night 76</p> <p>2.7 MYB Activator Competes with MYB Repressors 77</p> <p>2.8 miRNA‐ Targeted Degradation of MYB Transcript 78</p> <p>2.9 Turnover of Anthocyanin Vacuolar Content by Peroxidases 78</p> <p>2.10 Summary 79</p> <p>References 79</p> <p><b>3 The Subtleties of Subcellular Distribution: Pointing the Way to Underexplored Functions for Flavonoid Enzymes and End Products 89<br /></b><i>Brenda S.J. Winkel</i></p> <p>3.1 Multienzyme Complexes and Metabolic Networks 89</p> <p>3.2 New Insights from Global Surveys of Protein Interactions 90</p> <p>3.3 The Flavonoid Metabolon 91</p> <p>3.4 Subcellular Distribution of Flavonoid Enzymes and Evidence for Alternative Metabolons 94</p> <p>3.5 Posttranslational Modifications – An Underexplored Area of Flavonoid Metabolism 98</p> <p>3.6 Why Do We Need to Know? 99</p> <p>3.7 Future Prospects 99</p> <p>References 100</p> <p><b>4 Transcriptional and Metabolite Profiling Analyses Uncover Novel Genes Essential for Polyphenol Accumulation 109<br /></b><i>Wilfried Schwab, Ludwig Ring, and Chuankui Song</i></p> <p>4.1 Introduction 109</p> <p>4.2 Transcriptional and Metabolite Profiling Analyses in Strawberry Fruit 110</p> <p>4.3 Characterization of Peroxidase 27 113</p> <p>4.4 Competition of the Lignin and Flavonoid/Anthocyanin Pathways as Demonstrated by the Activity of Peroxidase 27 115</p> <p>4.5 Candidate Genes Putatively Correlated with Phenolics Accumulation in Strawberry Fruit 115</p> <p>4.6 Acylphloroglucinol Biosynthesis in Strawberry Fruit 118</p> <p>4.7 Glucosylation of Acylphloroglucinols 120</p> <p>4.8 Conclusion</p> <p>References 124</p> <p><b>5 Dietary (Poly)Phenols and Vascular Health 127<br /></b><i>Christine Morand, Nicolas Barber‐Chamoux, Laurent‐Emmanuel Monfoulet, and Dragan Milenkovic</i></p> <p>5.1 Introduction 127</p> <p>5.2 Vascular Health: A Prerequisite to Prevent Cardiometabolic Diseases and Cognitive Decline 128</p> <p>5.3 Diet and Vascular Health 130</p> <p>5.4 (Poly)Phenols: A Major Family of Dietary Plant Bioactive Compounds 131</p> <p>5.5 Fate of (Poly)Phenols in the Body and Biological Activities 133</p> <p>5.6 Nutritional Effects of Flavonoids in Protecting Cardiovascular Health 135</p> <p>5.7 Limitation of Knowledge and Strategy for Research 138</p> <p>5.8 Findings from Translational Research on Citrus Flavanones and Vascular Health 139</p> <p>5.9 Conclusion 142</p> <p>References 142</p> <p><b>6 Cellular‐Specific Detection of Polyphenolic Compounds by NMR‐and MS‐Based Techniques: Application to the Representative Polycyclic Aromatics of Members of the Hypericaceae, the Musaceae and the Haemodoraceae 149<br /></b><i>Dirk Hölscher,</i></p> <p>6.1 Introduction 149</p> <p>6.2 The Plant Genus Hypericum 150</p> <p>6.3 Phenylphenalenones: Plant Secondary Metabolites of the Haemodoraceae 151</p> <p>6.4 Phenalenone‐ Type Phytoalexins 157</p> <p>6.5 Laser Microdissection and Cryogenic NMR as a Combined Tool for Cell Type‐Specific Metabolite Profiling 160</p> <p>6.6 Matrix‐ free UV Laser Desorption/Ionization (LDI) at the Single‐Cell Level: Distribution of Secondary Metabolites of Hypericum Species 163</p> <p>6.7 LDI‐ MSI‐Based Detection of Phenalenone‐Type Phytoalexins in a Banana– Nematode Interaction 166</p> <p>6.8 LDI‐ FT‐ICR‐MSI Reveals the Occurrence of Phenylphenalenones in Red Paracytic Stomata 169</p> <p>6.9 Conclusion 171</p> <p>6.10 Acknowledgements 171</p> <p>References 171</p> <p><b>7 Metabolomics Strategies for the De replication of Polyphenols and Other Metabolites in Complex Natural Extracts 183<br /></b><i>Jean‐Luc Wolfender, Pierre‐Marie Allard, Miwa Kubo, and Emerson Ferreira Queiroz</i></p> <p>7.1 Introduction 183</p> <p>7.2 Metabolite Profiling and Metabolomics 184</p> <p>7.3 Metabolite Annotation and Dereplication 188</p> <p>7.4 Targeted Isolation of Original Polyphenols 198</p> <p>7.5 Conclusion 201</p> <p>References 201</p> <p><b>8 Polyphenols from Plant Roots: An Expanding Biological Frontier 207<br /></b><i>Ryosuke Munakata, Romain Larbat, Léonor Duriot, Alexandre Olry, Carole Gavira, Benoit Mignard, Alain Hehn, and Frédéric Bourgaud</i></p> <p>8.1 Introduction 207</p> <p>8.2 Polyphenols in Roots versus Shoots: Not More, Not Less, But Often Different 207</p> <p>8.3 Allelochemical Functions of Root Polyphenols 213</p> <p>8.4 Physiological Functions of Root Polyphenols in Plants 217</p> <p>8.5 Biotechnologies to Produce Root Polyphenols 220</p> <p>8.6 Conclusion 227</p> <p>References 227</p> <p><b>9 Biosynthesis of Polyphenols in Recombinant Micro‐organisms: A Path to Sustainability 237<br /></b><i>Kanika Sharma, Jian Zha, Sonam Chouhan, Sanjay Guleria, and Mattheos A.G. Koffas</i></p> <p>9.1 Introduction 237</p> <p>9.2 Flavonoids 239</p> <p>9.3 Stilbenes 247</p> <p>9.4 Coumarins 251</p> <p>9.5 Conclusion 253</p> <p>References 254</p> <p><b>10 Revisiting Wine Polyphenols Chemistry in Relation to Their Sensory Characteristics 263<br /></b><i>Victor de Freitas</i></p> <p>10.1 Introduction 263</p> <p>10.2 Astringency of Polyphenols 265</p> <p>10.3 Bitter Taste of Polyphenols 269</p> <p>10.4 Red Wine Colour 271</p> <p>10.5 Conclusion 276</p> <p>References 278</p> <p><b>11 Advances in Bio‐based Thermosetting Polymers 285<br /></b><i>Hélène Fulcrand, Laurent Rouméas, Guillaume Billerach, Chahinez Aouf, and Eric Dubreucq</i></p> <p>11.1 Introduction 285</p> <p>11.2 Industrial Sources of Polyphenols 289</p> <p>11.3 Principles of Thermoset Production 290</p> <p>11.4 Relationships between Structure and Reactivity of Polyphenols 292</p> <p>11.5 Thermosets from Industrial Lignins and Tannins 295</p> <p>11.6 Depolymerization of Lignins and Tannins to Produce Phenolic Building Blocks and their Glycidylether Derivatives 306</p> <p>11.7 Development of Dimethyloxirane Monophenols and Bisphenols as Thermosetting Building Blocks 310</p> <p>11.8 Conclusion 322</p> <p>References 323</p> <p><b>12 Understanding the Misunderstood: Products and Mechanisms of the Degradation of Curcumin 335<br /></b><i>Claus Schneider</i></p> <p>12.1 Introduction 335</p> <p>12.2 Degradation of Curcumin – A Historical and Personal Perspective 336</p> <p>12.3 The Degradation is an Autoxidation 341</p> <p>12.4 Novel Products of the Degradation/Autoxidation of Curcumin 344</p> <p>12.5 Transformation of Curcumin to Bicyclopentadione 348</p> <p>12.6 A Proposed Mechanism for the Autoxidation of Curcumin 350</p> <p>12.7 Microbial Degradation of Curcumin 354</p> <p>12.8 Conclusion 357</p> <p>References 357</p> <p><b>13 How to Model a Metabolon: Theoretical Strategies 363<br /></b><i>Julien Diharce and Serge Antonczak</i></p> <p>13.1 Introduction 363</p> <p>13.2 Localization 364</p> <p>13.3 Existing Structures 365</p> <p>13.4 Three‐ Dimensional Structures of Enzymes: Homology Modelling 367</p> <p>13.5 Modes of Access to Active Sites: Randomly Accelerated Molecular Dynamics 370</p> <p>13.6 Protein– Protein Association: Protein–Protein Docking 372</p> <p>13.7 Substrate Channelling and Molecular Dynamics 374</p> <p>13.8 Metabolon 378</p> <p>13.9 Conclusion 379</p> <p>References 381</p> <p>Index 387</p>
<p><b>About the Editors</b> <p><b>Heidi Halbwirth</b> is Associate Professor at Technische Universität Wien in Vienna, Austria. Her research activities have concentrated on plant secondary metabolism in horticulturally relevant plants with a strong focus on the enzymes involved and their structure-function relationships. Her particular research passion is flower colour, which allows the study of fundamental aspects of plant biochemistry and physiology. <p><b>Karl Stich</b> is Professor at Technische Universität Wien in Vienna, Austria. His field of expertise is the biochemistry of plants, and applied biochemistry in the field of plant protection with a strong focus on the secondary metabolism of plants. He is a longstanding member of Groupe Polyphenols and was awarded the 11<sup>th</sup> GP Medal for his scientific contributions to the elucidation of the flavonoid pathway. <p><b>Véronique Cheynier,</b> former president of the " Groupe Polyphénols " (2012-2016), is research director at the French National Institute for Agricultural Research (INRA) in Montpellier, France. Her research interests concern the study of the structure of polyphenolic compounds, notably vegetable tannins and anthocyanin pigments, their reactions during plant transformation processes, and their influence on the quality of foods and beverages, especially wine. <p><b>Stéphane Quideau,</b> former president of the " Groupe Polyphénols " (2008-2012), is full professor of Organic and Bioorganic Chemistry at the University of Bordeaux, France. His research laboratory is specialized in plant polyphenol chemistry and chemical biology, with a focus on the studies of ellagitannin chemical reactivity and synthesis, and interactions of bioactive polyphenols with their protein targets.
<p>Plant polyphenols are secondary metabolites that constitute one of the most common and widespread groups of natural products. They are crucial constituents of a large and diverse range of biological functions and processes, and provide many benefits to both plants and humans. Many polyphenols, from their structurally simplest representatives to their oligo/polymeric versions, are notably known as phytoestrogens, plant pigments, potent antioxidants, and protein interacting agents. <p>This sixth volume of the highly regarded <i>Recent Advances in Polyphenol Research</i> series is edited by Heidi Halbwirth, Karl Stich, Véronique Cheynier and Stéphane Quideau, and is a continuance of the series' tradition of compiling a cornucopia of cutting-edge chapters, written by some of the leading experts in their respective fields of polyphenol sciences. Highlighted herein are some of the most recent and pertinent developments in polyphenol research, covering such major areas as: <ul> <li>Chemistry and physicochemistry</li> <li>Biosynthesis, genetics & metabolic engineering</li> <li>Roles in plants and ecosystems</li> <li>Food, nutrition & health</li> <li>Applied polyphenols</li> </ul> <p>This book is a distillation of the most current information, and as such, will surely prove an invaluable source for chemists, biochemists, plant scientists, pharmacognosists and pharmacologists, biologists, ecologists, food scientists and nutritionists. <p><b>Also Available</b> <p>Recent Advances in Polyphenol Research, Volume 1 ; ISBN: 978-1-4051-5837-4 <p>Edited by Fouad Daayf and Vincenzo Lattanzio <p>Recent Advances in Polyphenol Research, Volume 2 ; ISBN: 978-1-4051-9399-3 <p>Edited by Celestino Santos-Buelga, Maria Teresa Escribano-Bailon, and Vincenzo Lattanzio <p>Recent Advances in Polyphenol Research, Volume 3 ; ISBN: 978-1-4443-3746-4 <p>Edited by Véronique Cheynier, Pascale Sarni-Manchado, and Stéphane Quideau <p>Recent Advances in Polyphenol Research, Volume 4 ; ISBN: 978-1-118-32967-2 <p>Edited by Annalisa Romani, Vincenzo Lattanzio, and Stéphane Quideau <p>Recent Advances in Polyphenol Research, Volume 5 ; ISBN: 978-1-118-88327-3 <p>Edited by Kumi Yoshida, Veronique Cheynier, and Stéphane Quideau

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