//img.uscri.be/pth/6301c591f7fcc1d31951dbc0551d5c5c05a3bf3f
Cette publication ne fait pas partie de la bibliothèque YouScribe
Elle est disponible uniquement à l'achat (la librairie de YouScribe)
Achetez pour : 273,46 € Lire un extrait

Téléchargement

Format(s) : PDF

avec DRM

Recent Advances in Polyphenol Research, Volume 1

De
416 pages
Polyphenols are the second most abundant class of substances in nature, and include tannins and flavonoids, many of which have extremely important antioxidant properties which have now been shown to have a key role in the prevention of cancer in humans.

This important book covers polyphenol chemistry, biosynthesis and genetic manipulation, ecology and plant physiology, food and nutritional aspects and the effects of polyphenols on health. Included within the contents are cutting edge chapters on biotic and abiotic stress in plants, safety and toxicity in foods, functionality and nutraceutical benefits in nutrition, and aspects of pharmaceutical and cosmetic discovery and development.

Sponsored by Groupe Polyphenols, this landmark book has been edited by Professor Fouad Daayf and Professor Vincenzo Lattanzio, who have drawn together an impressive list of internationally respected contributing authors, each providing a comprehensive review of the current situation regarding each important subject covered.

Recent Advances in Polyphenol Research is an important publication which will be of great use to chemists, biochemists, plant scientists, pharmacognosists and pharmacologists, food scientists and nutritionists. Libraries in all universities and research establishments where these subjects are studied and taught should have copies of this book on their shelves.

Voir plus Voir moins
9781405158374_1_pre.qxd 5/14/08 6:15 PM Page vii
Contents
Contributors Preface
1
1.1
1.2
1.3 1.4
2
2.1 2.2 2.3
2.4
Plant Phenolics – Secondary Metabolites with Diverse Functions Vincenzo Lattanzio, Paul A. Kroon, Stéphane Quideau and Dieter Treutter
Secondary metabolism in the interactions between plants and their environment Function and use of plant phenolics 1.2.1 UV sunscreens 1.2.2 Phenolics as signal compounds 1.2.3 Phenolics as pigments 1.2.4 Phenolics and plant growth 1.2.5 Phenolics and plant defense 1.2.5.1 Fungal pathogens 1.2.5.2 Phenolics and plant–insect interactions 1.2.6 Plant phenolics and health Note References
Lignification: are Lignins Biosynthesized via simple Combinatorial Chemistry or via Proteinaceous Control and Template Replication? John Ralph, Gösta Brunow, Philip J. Harris, Richard A. Dixon, Paul F. Schatz and Wout Boerjan
Introduction The current theory Is there a need for a new theory? 2.3.1 The challenge hypothesis (proteinaceous control and template replication) 2.3.2 Has the challenge hypothesis become a theory? Are criticisms of the current theory valid? 2.4.1 Lignification as a biochemical anomaly
xvi xx
1
1 5 6 6 8 9 11 13 17 22 24 24
36
36 37 37
38 38 38 38
9781405158374_1_pre.qxd 5/14/08 6:15 PM Page viii
viii
2.5
2.6 2.7
2.8 2.9 2.10 2.11
3
3.1 3.2 3.3 3.4
3.5
3.6 3.7
Contents
2.4.2 Theβ-ether frequency anomaly 2.4.3 ‘Obligatory’ linkages? Is there anything wrong with the dirigent hypothesis? 2.5.1 Monomer substitution 2.5.1.1 Has monomer substitution been disproven? 2.5.1.2 Malleability of lignification: what makes a good monolignol substitute? 2.5.2 ‘Well-defined primary structure’ 2.5.2.1 Sequencing of lignin oligomers 2.5.2.2 Monomer-independent sequences 2.5.2.3 The ‘urgent need to sequence lignin primary structure’ 2.5.3 Lignins’ racemic nature 2.5.3.1 The ‘number of isomers’ problem 2.5.4 Comments on template replication 2.5.5 Polymer branching Why the new hypothesis is not in contention Is lignification a biochemical anomaly? 2.7.1 Ferulate dehydrodimerization is combinatorial 2.7.2 Polysaccharide primary structure is NOT absolutely dictated Summary comments on the dirigent/replication hypothesis Conclusions Notes References
Flavonoid–Protein Binding Processes and their Potential Impact on Human Health Olivier Dangles and Claire Dufour
Introduction Biologically relevant chemical properties of flavonoids Binding processes prior to absorption Binding processes involved in flavonoid bioavailability 3.4.1 Absorption and conjugation 3.4.2 Transport in plasma 3.4.3 Tissue distribution and cellular metabolism Binding processes involved in the potential health effects of flavonoids 3.5.1 Inhibition of enzymes involved in ROS production 3.5.2 Modulation of the redox properties of flavonoids by binding to proteins 3.5.3 Inhibition of protein kinases 3.5.4 Inhibition of cytochrome P450 enzymes 3.5.5 Regulation of gene expression Conclusion References
39 40 40 40 41
43 45 45 46 47 47 48 48 49 50 51 51 51 52 53 55 58
67
67 68 71 72 72 73 73 74 74
76 78 79 80 83 83
5.5
5.8 5.9 5.10
5.6 5.7
6
Recent Advances in the Molecular Biology and Metabolic Engineering of Flavonoid Biosynthesis in Ornamental Plants Kevin M. Davies, Huaibi Zhang and Kathy E. Schwinn
Introduction Biosynthesis and functions of isoflavones Dietary sources of isoflavones Metabolic engineering of isoflavones 5.4.1 Metabolic engineering by ectopic expression of IFS 5.4.2 Structural biology-assisted design and metabolic engineering with an artificial bifunctional IFS enzyme Gene discovery in the proanthocyanidin biosynthetic pathway 5.5.1 Structural genes for PA biosynthesis 5.5.2 Regulatory genes for PA biosynthesis Metabolic engineering of PAs in plants Glycosyltransferases for modification of phenylpropanoid compounds in-vitrobiochemistry andin-vivofunction 5.7.1 UGTs active with non-flavonoid phenolic compounds 5.7.2 Glycosylation of flavonoid compounds 5.7.3 Problems for the functional annotation of UGTs Concerted strategies for metabolic engineering References Abbreviation list of the pathway genes
ix
88
139
Gene Discovery and Metabolic Engineering in the Phenylpropanoid Pathway Luzia V. Modolo, Yongzhen Pang, Li Tian and Richard A. Dixon
4.3 4.4 4.5
5.1 5.2 5.3 5.4
5
4.1 4.2
4
88 89 89 91 92 94 97 102 105 109 109
Methods for Synthesizing the Cocoa-Derived Oligomeric Epi-Catechins – Observations on the Anticancer Activity of the Cocoa Polyphenols Alan P. Kozikowski and Werner Tückmantel
123 124 128 130 131 132 138
113 113 115 115 115
113
Contents
9781405158374_1_pre.qxd 5/14/08 6:15 PM Page ix
Introduction Synthesis of procyanidins 4.2.1 General chemical properties of cocoa procyanidins 4.2.2 Earlier synthetic work 4.2.3 The synthesis of benzyl-protected building blocks 4.2.4 Inter-flavan bond formation using benzyl-protected building blocks 4.2.5 Establishment of inter-flavan bond stereochemistry 4.2.6 Further developments Anticancer activity Acknowledgments References
116 117 118 121 122
211 212 212
167
Introduction Anthocyanidins Anthocyanidin equilibrium forms New anthocyanin glycosides New anthocyanin acylglycosides Flavonoid complexes including at least one anthocyanidin subunit Metalloanthocyanins Biosynthesis and molecular biology Anthocyanin localization in plant cells Acknowledgments Notes References
167 168 178 181 183 187 188 189 191 192 192 193
211
202 203 205 207 207 207
139 142 143 144 149 152 157 158
202
Phenols and the Onset and Expression of Plant Disease Resistance Ray Hammerschmidt and Samantha I. Hollosy
Introduction Biosynthetic origins of defense-associated phenolic compounds Phenolic compounds as preformed defenses
Introduction Metabolic engineering of flavonoid production in flowers 6.2.1 Engineering yellow flower colors 6.2.2 Engineering blue flower colors Anthocyanic vacuolar inclusions Regulation of anthocyanin biosynthesis Concluding comments References
Contents
9781405158374_1_pre.qxd 5/14/08 6:15 PM Page x
x
6.1 6.2
8
Induced resistance and phenolics The biosynthesis of SA The network of signaling and the action of SA Conclusions Acknowledgment References
Salicylic Acid and Induced Plant Defenses Jean-Pierre Métraux, Elisabeth Lamodière, Jérémy Catinot, Olivier Lamotte and Christophe Garcion
8.1 8.2 8.3 8.4 8.5 8.6
9.1 9.2 9.3
9
7
7.1 7.2 7.3 7.4 7.5 7.6 7.7 7.8 7.9 7.10 7.11 7.12
Recent Advances in the Field of Anthocyanins – Main Focus on Structures Øyvind M. Andersen
6.3 6.4 6.5 6.6
9781405158374_1_pre.qxd 5/14/08 6:15 PM Page xi
9.4 9.5
9.6
9.7
9.8 9.9 9.10
10
10.1
10.2
10.3
Contents
9.3.1 Resistance of onion bulbs 9.3.2 Fusarium wilt of carnation 9.3.3 Mango fruit andAlternaria 9.3.4 Regulation of preformed antifungal compounds by phenols in avocado 9.3.5 Chlorogenic acid and the infection of stone fruit byMonilinia Active defense Localized defenses 9.5.1 Phenolic phytoalexins 9.5.2 Phenolic structural defenses 9.5.3 Plant phenols and induced disease resistance Responses of the induced plant 9.6.1 Induced resistance in green bean andC.lindemunthianum 9.6.2 Acibenzolar-S-methyl mediated induced resistance 9.6.3 Plant growth-promoting rhizobacteria and induced resistance 9.6.4 Silicon as a modulator of defense and phenolic compounds Chemical induction of phenolic compounds and resistance 9.7.1 Structural phenolic compounds and induced resistance 9.7.2 Antioxidant activity of phenolic compounds and plant defense Phenols and defense: a multitude of roles Acknowledgment References
Bioactivity, Absorption, and Metabolism of Anthocyanins Giuseppe (Joe) Mazza and Colin D. Kay
Introduction 10.1.1 Structural characteristics Bioactivity 10.2.1 Antioxidant activity 10.2.2 Anti-inflammatory effects 10.2.3 Anti-atherogenic effects 10.2.4 Anticarcinogenic effects 10.2.5 Antibacterial and antiviral activity 10.2.6 Neuroprotective effects 10.2.7 Prevention of obesity 10.2.8 Gastric protective effects 10.2.9 Improvement of vision Absorption of anthocyanins 10.3.1 Variability of absorption 10.3.1.1 Variations in dosage 10.3.1.2 Chemical structure of the anthocyanins 10.3.1.3 Food matrix 10.3.1.4 Analytical methodology 10.3.2 Elimination
xi
213 214 214
214 215 215 216 216 218 219 220 220 220 220 221 221 221 222 222 223 223
228
228 228 229 230 233 233 234 235 235 235 236 236 236 239 239 240 241 241 242
9781405158374_1_pre.qxd 5/14/08 6:15 PM Page xii
xii
10.4
10.5 10.6
11
11.1 11.2 11.3 11.4
11.5
11.6 11.7 11.8
12
12.1 12.2
Contents
10.3.3 The concentration of anthocyanins in human blood and urine is very low 10.3.4 Suggested mechanisms of anthocyanin absorption 10.3.5 Structural transformations of anthocyanins Metabolism of anthocyanins 10.4.1 Human studies 10.4.2 Animal studies 10.4.2.1 Rat studies 10.4.2.2 Pig studies 10.4.3 Potential mechanisms of anthocyanin metabolism Conclusions References
Bioavailability, Metabolism, and Bioactivity of Food Ellagic Acid and Related Polyphenols Francisco A. Tomás-Barberán, Maria Teresa García-Conesa, Mar Larrosa, Begoña Cerdá, Rocio González-Barrio, Maria José Bermúdez-Soto, Antonio González-Sarrías and Juan Carlos Espín
Introduction Ellagitannins and ellagic acid as examples of bioactive polyphenols Evaluation of antioxidant activityin vitro Biological activity associated to ellagitannin-rich food intake; clinical studies Questions arising after the demonstration of the large antioxidant activityin vitroand the biological activity associated with the intake of ellagitannin-rich food 11.5.1 Bioavailability and metabolism of ellagitannins and ellagic acid and distribution of the metabolites in different tissues 11.5.2 Evaluation of the biological activity of ellagitannin metabolites producedin vivo Conclusion Acknowledgments References
Multiplicity of Phenolic Oxidation Products in Apple Juices and Ciders, from Synthetic Medium to Commercial Products Sylvain Guyot, Stéphane Bernillon, Pascal Poupard and Catherine M.G.C. Renard
Introduction Preparation and characterization of the caffeoylquinic acido-quinone solution
243 243 245 247 247 251 251 252 252 254 254
263
263 264 265
265
266
267
269 275 275 275
278
278
281
9781405158374_1_pre.qxd 5/14/08 6:15 PM Page xiii
12.3
12.4 12.5 12.6 12.7
13
13.1 13.2
13.3
13.4 13.5 13.6
14
14.1 14.2
Contents
Incubation of caffeoylquinic acido-quinone in model solutions 12.3.1 Incubation of caffeoylquinic acido-quinone with caffeoylquinic acid 12.3.2 Incubation of caffeoylquinic acido-quinone with ()-epicatechin LC-MS analysis of oxidation products in commercial apple beverages Conclusions Acknowledgments References
Phytoestrogens in Drug Discovery for Controlling Steroid Biosynthesis Sampo Karkola, Annamaria Lilienkampf and Kristiina Wähälä
Introduction Aromatase 13.2.1 Natural phytoestrogens as aromatase inhibitors 13.2.1.1 Anti-aromatase activity of phytoestrogens in human placental microsome-based assays 13.2.1.2 Anti-aromatase activity of phytoestrogens in cell-based assays 13.2.1.3 Anti-aromatase activity of phytoestrogens in recombinant-enzyme assays 13.2.1.4 The anti-aromatase activity of various phytoestrogens 13.2.2 The structure–activity relationship of phytoestrogens 13.2.3 Phytoestrogens as lead compounds for aromatase inhibition 17β-Hydroxysteroid dehydrogenases and their inhibition by phytoestrogens 13.3.1 17β-HSD type 1 13.3.1.1 Binding of phytoestrogens to 17β-HSD1 13.3.2 17β-HSD types 2 and 4 13.3.3 Fungal 17β-HSDcl 13.3.3.1 Binding of phytoestrogens to 17β-HSDcl 13.3.4 17β-HSD type 3 13.3.5 17β-HSD type 5 13.3.6 Phytoestrogens as lead compounds for 17β-HSD inhibitors Conclusions Acknowledgments References
Recent Advances in the Chemical Synthesis and Biological Activity of Phenolic Metabolites Denis Barron
Introduction The different sites of generation of phenolic metabolites 14.2.1 The saliva
xiii
282
282 285 288 290 290 290
293
293 293 295
295
298
299 299 300 301 304 305 307 307 308 309 310 310 311 312 313 313
317
317 318 318
9781405158374_1_pre.qxd 5/14/08 6:15 PM Page xiv
xiv
14.3
14.4
14.5
14.6
14.7 14.8
Contents
14.2.2 The stomach 14.2.3 The small intestine 14.2.4 The colon 14.2.5 The liver 14.2.6 Metabolism at the target tissues or cells Nature of the metabolites of phenolic compounds 14.3.1 Flavone and flavonol metabolites 14.3.2 Flavanonone and flavanonol metabolites 14.3.3 Flavan 3-ol metabolites 14.3.4 Ellagic tannin metabolites 14.3.5 Lignan metabolites 14.3.6 Isoflavone metabolites 14.3.7 Hydroxycinnamic acid metabolites 14.3.8 Curcumin metabolites 14.3.9 Resveratrol metabolites The chemical synthesis of phenolic conjugates 14.4.1 The preparation of O-glucuronides 14.4.2 The preparation of O-sulfates The biological properties of phenolic conjugates 14.5.1 Antioxidant properties 14.5.1.1 Flavonol conjugates 14.5.1.2 Flavone conjugates 14.5.1.3 Flavanone conjugates 14.5.1.4 Flavan 3-ol conjugates 14.5.1.5 Isoflavone conjugates 14.5.1.6 The case of the 7-O-conjugates 14.5.2 Pro-oxidant properties 14.5.3 Interaction with signaling cascades 14.5.4 Enzyme inhibition 14.5.4.1 Aldose reductase 14.5.4.2β-glucuronidase 14.5.4.3 Xanthine oxidase 14.5.4.4 Glycerol 3-phosphate dehydrogenase 14.5.4.5 Cyclooxygenase-2 14.5.5 Effect on vascular function and angiogenesis 14.5.6 Non-covalent binding to proteins 14.5.7 Activity of microbial and tissular metabolites The cellular transport of phenolic conjugates 14.6.1 Cellular efflux 14.6.2 Cellular uptake Conclusions References
319 319 320 320 321 321 321 322 324 324 325 325 326 327 328 328 329 332 334 334 334 340 340 340 340 341 342 343 344 344 344 344 345 345 345 345 346 346 346 347 348 350
9781405158374_1_pre.qxd 5/14/08 6:15 PM Page xv
15
15.1 15.2
15.3
15.4
15.5
Polyphenols and Gene Expression Uwe Wenzel and Hannelore Daniel
Index
Contents
Introduction The effects of polyphenols on the expression of genes underlying detoxification mechanisms Polyphenols and the expression of genes underlying cancer-relevant processes The impact of polyphenols on the expression of genes underlying atherosclerosis-relevant processes References
The color plate section follows page 42
xv
359
359
359
363
369 373
379