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<p>List of Contributors xv</p> <p><b>1 Structural Diversity of Polyphenols and Distribution in Foods </b><b>1<br /></b><i>Antonio González-Sarrías, Francisco A. Tomás-Barberán, and Rocío García-Villalba</i></p> <p>1.1 Introduction 1</p> <p>1.2 Classification and Chemistry of Polyphenols 2</p> <p>1.2.1 Flavonoids 2</p> <p>1.2.2 Nonflavonoids 7</p> <p>1.3 Dietary Intake and Food Sources of Polyphenols 10</p> <p>1.3.1 Flavonoids 11</p> <p>1.3.2 Nonflavonoids 14</p> <p>1.4 Databases Used to Assess Dietary Exposure to Polyphenols 16</p> <p>1.5 Bioavailability, Metabolism, and Bioactivity of Dietary Polyphenols 17</p> <p>Acknowledgments 20</p> <p>References 20</p> <p><b>2 Nonextractable Polyphenols: A Relevant Group with Health Effects </b><b>31<br /></b><i>Yuridia Martínez-Meza, Rosalía Reynoso-Camacho, and Jara Pérez-Jiménez</i></p> <p>2.1 Introduction: The Concept of Nonextractable Polyphenols (NEPP) 31</p> <p>2.2 Contribution of NEPP to Total Polyphenol Content and Intake 33</p> <p>2.2.1 Strategies for the Extraction and Analysis of NEPP 34</p> <p>2.2.2 NEPP Content in Common Foods 38</p> <p>2.2.3 Estimation of NEPP Intake in Different Populations 40</p> <p>2.3 Metabolic Fate of NEPP: A Key Process for Their Health Effects 42</p> <p>2.3.1 Current Evidence of the Metabolic Transformation of NEPP 42</p> <p>2.3.2 Specific Features of the Metabolic Fate of NEPP 46</p> <p>2.4 How NEPP may Exhibit Health Effects 48</p> <p>2.4.1 Antioxidant Effects 48</p> <p>2.4.2 Microbiota Modulation 51</p> <p>2.4.3 Biological Activities of Microbial Metabolites 53</p> <p>2.4.4 Synergy with Dietary Fiber 58</p> <p>2.5 Studies on the Health Effects of NEPP 60</p> <p>2.5.1 Local vs Systemic Effects 60</p> <p>2.5.2 Effects on Gastrointestinal Health 62</p> <p>2.5.3 Effects on Cardiometabolic Health 64</p> <p>2.6 Perspectives 66</p> <p>References 68</p> <p><b>3 Analytical Strategies for Determining Polyphenols in Foods and Biological Samples </b><b>85<br /></b><i>Lucía Olmo-García, Romina P. Monasterio, Aadil Bajoub, and Alegría Carrasco-Pancorbo</i></p> <p>3.1 Introduction: Importance of the Determination of Polyphenols 85</p> <p>3.2 Most Widely Used Extraction Systems and New Trends 89</p> <p>3.3 Determination of the Phenolic Compounds in Foods 92</p> <p>3.3.1 Classic Methods For Polyphenols Determination: Spectrophotometric Assays 92</p> <p>3.3.2 Evolution of the Traditional Methods to Characterize the Polyphenolic Fraction of Foods: Chromatographic and Electrophoretic Separation and Subsequent Detection 94</p> <p>3.3.3 Other Analytical Strategies 106</p> <p>3.4 Some Considerations Regarding the Determination of Polyphenols in Biological Samples 107</p> <p>3.5 Conclusions and Future Directions 111</p> <p>Acknowledgments 116</p> <p>References 116</p> <p><b>4 Hydroxycinnamates </b><b>129<br /></b><i>Iziar A. Ludwig, Laura Rubió, Alba Macià, and Maria P. Romero</i></p> <p>4.1 Introduction 129</p> <p>4.2 Metabolism of Hydroxycinnamates and Metabolic Pathways 130</p> <p>4.2.1 Absorption in the Upper Gastrointestinal Tract 135</p> <p>4.2.2 Absorption in the Lower Gastrointestinal Tract 136</p> <p>4.3 Bioaccessibility and Bioavailability of Hydroxycinnamates: Influence of Food Matrix, Processing, Dose, and Interindividual Differences 138</p> <p>4.3.1 Bioavailability of Hydroxycinnamates in Fruits, Vegetables, and Beverages 139</p> <p>4.3.2 Bioavailability in Cereal-Based Products 144</p> <p>4.4 Biological Activity of Hydroxycinnamates and Their Derivatives 148</p> <p>References 153</p> <p><b>5 Flavonols and Flavones </b><b>163<br /></b><i>Cláudia Nunes dos Santos, Regina Menezes, Diogo Carregosa, Katerina Valentova, Alexandre Foito, Gordon McDougall, and Derek Stewart</i></p> <p>5.1 Introduction 163</p> <p>5.2 Uptake and Metabolism of Flavonols and Flavones 167</p> <p>5.2.1 Flavonols or 3-Hydroxyflavones (Quercetin, Kaempferol, Myricetin) 167</p> <p>5.2.2 Flavones (Luteolin, Apigenin) 170</p> <p>5.3 Microbiota Formation of Low Molecular Weight Phenolic, Common Colonic Metabolites 173</p> <p>5.3.1 Flavonols (Quercetin, Kaempferol, Myricetin) 173</p> <p>5.3.2 Flavones (Luteolin, Apigenin) 175</p> <p>5.4 Health Effects of Flavonol and Flavone Metabolites 177</p> <p>5.4.1 Flavonols or 3-Hydroxyflavones 177</p> <p>5.4.2 Flavones (Luteolin, Apigenin) 181</p> <p>5.4.3 Flavonols, Flavones and Their Low Molecular Weight Colonic Metabolites in Health 184</p> <p>5.5 Conclusions and Future Perspectives 185</p> <p>Acknowledgments 186</p> <p>References 186</p> <p><b>6 Isoflavones </b><b>199<br /></b><i>Cara L. Frankenfeld</i></p> <p>6.1 Uptake and Metabolism of Isoflavones 199</p> <p>6.1.1 Gut Microbial Metabolism 199</p> <p>6.1.2 Pharmacokinetic Studies 201</p> <p>6.2 Biological Mechanisms of Isoflavones 203</p> <p>6.2.1 Hormonal 203</p> <p>6.2.2 Antioxidant 204</p> <p>6.2.3 Antiinflammatory 205</p> <p>6.3 Physiological and Health Effects of Isoflavones 205</p> <p>6.3.1 Bone 206</p> <p>6.3.2 Cancer 208</p> <p>6.3.3 Reproductive Hormones 212</p> <p>6.3.4 Cardiovascular Disease, Blood Triglycerides and Cholesterol, and Inflammatory Markers 213</p> <p>6.3.5 Diabetes, Insulin Resistance, and Blood Glucose and Insulin 216</p> <p>6.3.6 Obesity 217</p> <p>6.3.7 Menopausal Symptoms 218</p> <p>6.3.8 Neurological Outcomes 218</p> <p>6.4 Physiological and Health Effects of Isoflavone Metabolites and Metabotypes 219</p> <p>6.5 Summary of Isoflavone Intake and Health 221</p> <p>References 221</p> <p><b>7 Dietary Anthocyanins </b><b>245<br /></b><i>Iva Fernandes, Hélder Oliveira, Cláudia Marques, Ana Faria, Conceição Calhau, Nuno Mateus, and Victor de Freitas </i>7.1 Absorption and Metabolism of Anthocyanins 245</p> <p>7.1.1 Oral Cavity Absorption 248</p> <p>7.1.2 Gastric Absorption 251</p> <p>7.1.3 Intestinal Absorption 254</p> <p>7.1.4 Microbial Metabolism 255</p> <p>7.2 Pharmacokinetics of Anthocyanins 258</p> <p>7.3 Factors Affecting Anthocyanin Bioavailability 259</p> <p>7.4 Biological Activity of Anthocyanin Metabolites 262</p> <p>7.4.1 Phase II Metabolites 265</p> <p>7.5 Conclusion 272</p> <p>References 272</p> <p><b>8 Flavan-3-ols: Catechins and Proanthocyanidins </b><b>283<br /></b><i>Claudia Favari, Pedro Mena, Claudio Curti, Daniele Del Rio, and Donato Angelino</i></p> <p>8.1 Introduction: Chemistry and Main Dietary Sources 283</p> <p>8.2 Bioavailability of Flavan-3-ols 288</p> <p>8.2.1 Absorption and Metabolism: Native and Colonic Phase II Metabolites 289</p> <p>8.2.2 Pharmacokinetics and Urinary Excretion of Circulating Metabolites: Interindividual Differences 293</p> <p>8.3 Health Benefits of Flavan-3-ols and Their Derived Circulating Metabolites 298</p> <p>8.3.1 Cognitive 299</p> <p>8.3.2 Inflammation and Cardiometabolic Diseases 302</p> <p>8.3.3 Urinary Tract Infections 305</p> <p>8.4 Conclusions and Future Perspectives 307</p> <p>References 308</p> <p><b>9 Ellagitannins and Their Gut Microbiota-Derived Metabolites: Urolithins </b><b>319<br /></b><i>Rocío García-Villalba, Juan A. Giménez-Bastida, María A. Ávila-Gálvez, Francisco A. Tomás-Barberán, Juan C. Espín, and Antonio González-Sarrías</i></p> <p>9.1 Chemistry and Sources of Ellagitannins and Ellagic Acid 319</p> <p>9.2 Bioavailability of Ellagitannins and Ellagic Acid 323</p> <p>9.3 The Microbial Metabolism of Ellagitannins and Ellagic Acid: Urolithins 324</p> <p>9.3.1 Urolithin Production and Bioavailability 324<i>                     </i></p> <p>9.3.2 Tissue Distribution of Urolithins after Consumption of Ellagitannins 328</p> <p>9.3.3 Interaction of ETs and Urolithins with the Gut Microbiota 329</p> <p>9.3.4 Interindividual Variability: Metabotypes 331</p> <p>9.3.5 Analysis of Urolithins 332</p> <p>9.4 Significance of Ellagitannins, Ellagic Acid, and Urolithins for Human Health 335</p> <p>9.4.1 Antioxidant Effects 336</p> <p>9.4.2 Antiinflammatory Properties 338</p> <p>9.4.3 Anticarcinogenic Effects 340</p> <p>9.4.4 Neuroprotective Effects 343</p> <p>9.4.5 Estrogenic Modulation 344</p> <p>9.4.6 Urolithins, Clinical Trials, and Interindividual Variability–Health Relationship 345</p> <p>9.5 Conclusion 347</p> <p>Acknowledgments 348</p> <p>References 348</p> <p><b>10 Lignans </b><b>365<br /></b><i>Knud E. Bach Knudsen, Natalja Nørskov, Anne K. Bolvig, Mette Skou Hedemann, and Helle Nygaard Lærke</i></p> <p>10.1 Introduction 365</p> <p>10.2 Lignans in Foods 368</p> <p>10.3 Metabolism of Lignans 373</p> <p>10.3.1 Kinetics of Absorption of Plant Lignans 376</p> <p>10.3.2 Conversion of Plant Lignans to Enterolignans 382</p> <p>10.4 Blood Levels of Lignans after Dietary Intervention 387</p> <p>10.5 Bioactivity of Plant Lignans and Enterolignans 393</p> <p>10.6 Conclusions and Future Perspectives 394</p> <p>Acknowledgments 395</p> <p>References 395</p> <p><b>11 Stilbenes: Beneficial Effects of Resveratrol Metabolites in Obesity, Dyslipidemia, Insulin Resistance, and Inflammation </b><b>407<br /></b><i>Itziar Eseberri, Iñaki Milton-Laskibar, Alfredo Fernández-Quintela, Saioa Gómez-Zorita, and María P. Portillo</i></p> <p>11.1 Introduction: Occurrence and Intake 407</p> <p>11.2 Absorption, Metabolism, and Excretion of Resveratrol 408</p> <p>11.3 Biological Effects of Resveratrol Metabolites 412</p> <p>11.3.1 <i>In vitro </i>Studies 413</p> <p>11.3.2 <i>In vivo </i>Studies 428</p> <p>11.4 Conclusion 429</p> <p>Acknowledgments 429</p> <p>References 430</p> <p><b>12 Flavanones </b><b>439<br /></b><i>Gema Pereira-Caro, Colin D. Kay, Michael N. Clifford, and Alan Crozier</i></p> <p>12.1 Introduction 439</p> <p>12.2 Flavanones and Their Occurrence 441</p> <p>12.3 Absorption of Flavanone Metabolites in the Proximal and Distal Gastrointestinal Tract 443</p> <p>12.4 Formation of 3-(3′-Hydroxy-4′-Methoxyphenyl) Hydracrylic Acid 454</p> <p>12.5 Factors Affecting the Bioavailability of Flavanones 457</p> <p>12.5.1 Impact of Physical Activity 457</p> <p>12.5.2 Matrix Effects 458</p> <p>12.5.3 Probiotics 459</p> <p>12.5.4 Inter- and Intraindividual Variability 460</p> <p>12.5.5 Other Effects 462</p> <p>12.6 Analysis of Flavanone Metabolites and Catabolites 462</p> <p>12.7 Biomarkers and Metabolomics 465</p> <p>12.8 Protective Effects 467</p> <p>12.8.1 Cardiovascular Disease 468</p> <p>12.8.2 Diabetic and Metabolic Syndrome 471</p> <p>12.8.3 Cancer 472</p> <p>12.8.4 Cognition and Neuroprotection 473</p> <p>12.8.5 Bones 474</p> <p>12.8.6 Liver 474</p> <p>12.8.7 Immunomodulation and Antiinflammatory Activity 474</p> <p>12.8.8 Gastric Function and the Microbiome 475</p> <p>12.8.9 Modulation of the Microbiota and Biological Activity of Microbial Metabolites 475</p> <p>References 479</p> <p><b>13 Understanding Polyphenols’ Health Effects Through the Gut Microbiota </b><b>497<br /></b><i>Maria V. Selma, Francisco A. Tomás-Barberán, Maria Romo-Vaquero, Adrian Cortés-Martín, and Juan C. Espín</i></p> <p>13.1 Microbial Metabolism of Dietary Polyphenols 497</p> <p>13.2 Bacteria Responsible for Dietary Polyphenols Transformations and Health Implications 507</p> <p>13.3 Modulation of Gut Microbiota by Dietary Polyphenols 516</p> <p>Acknowledgments 519</p> <p>References 519</p> <p>Index 533</p>

<p><b>Francisco A. Tomás-Barberán, Antonio González-Sarrías, Rocío García-Villalba,</b> Department of Food Science and Technology, CEBAS-CSIC, Murcia, Spain.

<p><b>Presents recent research on metabolism and the health effects of polyphenols</b> <p>Consumer interest in the health benefits of many phenolic compounds found in plant foods and derivatives has grown considerably in recent years, giving rise to an increased demand for functional foods. Although preclinical and observational studies have promoted the protective properties of polyphenols for a range of chronic diseases, evidence has shown that most dietary polyphenols have little bioavailability. Once ingested, most of them are metabolized by either the intestinal enzymes or by the gut microbiota and then undergo extensive phase-II metabolism reaching significant concentrations of conjugated metabolites. They remain in the systemic circulation and target systemic tissues which trigger biological effects. The polyphenol-derived metabolites produced in humans are dependent upon the composition of the gut microbiota and the subject genetics. Thus all the metabolites do not show the same biological activity in different individuals. To fully understand the health effects of polyphenols, further clinical investigations are required. <p><i>Dietary Polyphenols</i> describes the latest findings on the polyphenol metabolism and reviews the current evidence on their health effects and that of their bioavailable metabolites. Emphasizing the importance of interindividual variability and the critical role of gut microbiota, this authoritative volume features contributions from recognized experts in the field, exploring specific families of extractable and non-extractable phenolic compounds that exhibit potential health effects. Topics include structural diversity of polyphenols and distribution in foods, bioavailability and bioaccessibility of phenolics, metabolism, and gastrointestinal absorption of various metabolites and their health effects. This comprehensive volume: <ul> <li>Discusses the bioavailability, bioaccessibility, pharmacokinetics studies, and microbial metabolism of different groups of phenolic compounds</li> <li>Examines the interaction between polyphenols and gut microbiota</li> <li>Describes analytical methods for identifying and quantifying polyphenols in foods and biological samples</li> <li>Reviews recent epidemiological and clinical intervention studies showing protective effects of polyphenols</li> </ul> <p><i>Dietary Polyphenols: Metabolism and Health Effects</i> is an important resource for scientists working in the area of dietary polyphenols and health effects, microbiota, and their interaction with other nutritional compounds, and for health professionals, nutritionists, dieticians, and clinical researchers with interest in the role of polyphenols in the prevention and treatment of chronic diseases.

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