Polyphenols in plants : isolation, purification and extract preparation

444 Pages·2019·25.634 MB·English

by  Watson, Ronald Ross

Polyphenols in Plants
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Polyphenols in Plants
Isolation, Purification and Extract Preparation
Second Edition
Edited by
Ronald Ross Watson
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Contents
Contributors xi 4 OtherOff-the-MenuMiscellaneous 16
Preface xv 5 ConclusiveRemarks 16
Acknowledgments xvii Acknowledgments 17
References 17
Section A FurtherReading 21
Polyphenols in Agriculture, Plant
Growth Economics and Delivery
2. Polyphenols in Agricultural
1. Not Only What Is Food Is
Byproducts and Food Waste 23
Good—Polyphenols From Edible
and Nonedible Vegetable Waste 3 IoannisMourtzinosandAthanasiaGoula
1 Introduction 23
LauraSiracusaandGiuseppeRuberto
2 ByproductsRichinPhenolicCompounds 23
1 Introduction 3 2.1 CoffeeByproducts 23
1.1 WhytoRe-evaluate:TheImportance 2.2 GrapeandWineByproducts 24
ofVegetableWastesintheCircular 2.3 CitrusByproducts 24
EconomyEra 3 2.4 AppleByproducts 24
1.2 TheTightBiochemicalConnection 2.5 PomegranateByproducts 24
BetweenVegetablesandTheir 2.6 OliveByproducts 25
Byproducts 4 2.7 OnionByproducts 25
2 BehindaCommonMeal:Polyphenols 2.8 OtherPlantByproducts 25
inFoodByproducts 5 3 MethodsforRecoveryofPolyphenolic
2.1 IntroducingtheConceptofThisSection 5 CompoundsFromByproducts 25
2.2 FirstCourse:PastaWithTomatoSauce 3.1 DryingMethods 25
(PolyphenolsinWheatBranand 3.2 PolyphenolExtraction 25
TomatoByproducts) 6 3.3 Ultrasound-AssistedExtraction 26
2.3 AFreshSideDish:MixedSalad 3.4 Microwave-AssistedExtraction(MAE) 26
(PolyphenolsFromFennel,Carrot, 3.5 SupercriticalFluidExtraction 27
LettuceLeaves,Artichoke,LemonJuice, 3.6 PressurizedLiquidExtraction 27
andOliveOilByproducts) 7 3.7 AdsorptiveExtraction 27
2.4 Fruits(PolyphenolsFromApple, 3.8 MolecularlyImprintedPolymers(MIP) 27
Pomegranate,Banana,andBerry 3.9 ExtractionAssistedWithCyclodextrins
Byproducts) 10 asaCosolvent 28
3 SomethingtoDrink:PolyphenolsinMost 4 StabilizationofPhenolicExtracts 28
CommonBeverageByproducts 13 4.1 MethodsofPhenolicExtracts
3.1 OrangeJuice(PolyphenolsFrom StabilizationbyEncapsulation 30
OrangeByproducts) 13 5 AdditionofPhenolicExtractsinFoods 34
3.2 Wine(PolyphenolsFromGrape 6 Conclusions 37
andWineByproducts) 13 References 38
v
vi Contents
3. Phenolic Natural Compounds and 3.3 AdvancementinScienceandTechnology 69
Their Influence on Physiological 3.4 Prospects 70
Processes in Plants 45 4 Tea 70
4.1 Use 70
CorneliuTanase,Oana-CrinaBujorand 4.2 Resources 70
ValentinI.Popa 4.3 AdvancementofScienceandTechnology 71
1 Introduction 45 4.4 Prospect 72
2 NaturalSourcesofPhenolicCompounds 46 5 Coffee 72
3 InfluenceofSomePhenolicNatural 5.1 Use 72
ProductsonPlant’sDevelopment 46 5.2 Production 73
3.1 TheEffectofPhenolicCompounds 5.3 Prospect 74
onSeedGerminationProcess 46 6 Gambier 74
3.2 TheInfluenceofPhenolicCompounds 6.1 Use 74
onGrowthandDevelopmentProcess 6.2 Resources 75
onPlants 50 6.3 AdvancementofScienceandTechnology 75
3.3 TheInfluenceofthePhenolicCompounds 6.4 Prospects 75
ontheCellDivisionProcess 51 7 Mangosteen 75
3.4 TheInfluenceofPhenolCompoundson 7.1 Use 75
PhotosyntheticActivity 53 7.2 Resource 76
4 Conclusions 55 7.3 AdvancementofScienceandTechnology 76
References 56 7.4 Prospects 77
8 Conclusion 77
4. Improving Bioavailability of References 77
Polyphenols Using Nanodelivery
Systems Based on Food Polymers 59 Section B
Isolation and Analysis of Polyphenol
A.AguirreandR.Borneo
Structure
1 Introduction 59
2 HealthBenefitsofPolyphenols
6. Structure and Antioxidant Efficiency of
Phytochemicals 59
Beech ( L.) Bark
3 Nanoparticles 61 Fagus sylvatica
Polyphenols Unraveled by High-
3.1 NanoparticlesCanBeUsedtoEnhance
Performance Liquid Chromatography/
theBioavailabilityofPolyphenols 61
4 FoodDerivedPolymersforPolyphenol Photodiode Array Detection/Multistage
NanodeliverySystems 62 Electrospray Mass Spectrometry and
4.1 Polysaccharide-BasedSystems 62 Chemometrics 83
4.2 Protein-BasedSystems 62
5 FinalRemarks 62 Tama´sHofmann
References 63 1 Introduction 83
2 SamplePreparationandExtraction 84
5. Polyphenols Resources in Indonesia
3 DeterminationofAntioxidantCapacities 84
From Economic Perspective 67 4 TheHPLC-PDA-ESI-MS/MSIdentificationof
Beech(FagussylvaticaL.)BarkPolyphenols 86
SuminarSetiatiAchmadi
5 MassSpectrometricEvaluationofRelative
1 Introduction 67 QuantitiesoftheCompoundsbyMRMPeak
2 TanninsFromMangroveForest 67 Areas 93
2.1 Use 67 6 StudyoftheAntioxidantEfficiencyof
2.2 Resources 68 CompoundsUsingChemometrics 95
2.3 AdvancementinScienceandTechnology 68 6.1 CorrelationAnalysis 95
2.4 Implication 68 6.2 FactorAnalysis 101
3 Cocoa 68 6.3 ClusterAnalysis 104
3.1 Use 68 6.4 CombinedEvaluationofChemometric
3.2 Resources 69 Analysis 105
Contents vii
7 Conclusions 107 7.3 SuperheatedLiquidExtraction 145
Acknowledgments 107 7.4 SupercriticalFluidExtraction 145
References 107 7.5 ComparisonoftheEffectofAuxiliary
EnergiesontheExtractionofFlavonoids
7. Characterization and Quantification FromCitrus 145
of Polyphenols in Fruits 111 8 IdentificationandQuantitationofCitrus
Flavonoids 147
FabianWeberandMaikePasson 9 ForeseeableApplicationsofCitrus
1 Introduction 111 Flavonoids 147
2 SamplePreparation 112 References 148
3 AnalyticalMethods 113
10. Extraction Methods of Polyphenol
3.1 SumParameters 113
3.2 ChromatographicTechniques 114 From Grapes: Extractions of Grape
3.3 ChemometricMethods 116 Polyphenols 151
4 PreparativeMethods 117
References 117 IvanaTomaz,NeraHuzani(cid:1)c,DarkoPreiner,
DomagojStupi(cid:1)c,ZˇeljkoAndabaka,EdiMaleti(cid:1)c,
JasminkaKaroglanKonti(cid:1)candDanijelaAsˇperger
8. Phenotypic Diversity of Colored
Phytochemicals in Sorghum 1 Introduction 152
2 Sampling 153
Accessions With Various Pericarp
3 SamplePreparation 153
Pigments 123
3.1 SampleStorage 154
3.2 Thawing 154
HaleyDavis,XiaoyuSu,YantingShen,JingwenXu,
DonghaiWang,J.ScottSmith,FadiAramouniand 3.3 Drying 154
WeiqunWang 4 ExtractionTechniques 154
1 Introduction 123 4.1 Solid-LiquidExtraction 155
2 PericarpPigments 124 4.2 Ultrasound-AssistedExtraction 155
3 Phytochemicals 125 4.3 Microwave-AssistedExtraction 159
4 Anthocyanins 125 4.4 Enzyme-AssistedExtraction 161
5 Carotenoids 126 4.5 MatrixSolidPhaseDispersion 161
6 HealthBenefitsofColoredPhytochemicals 127 4.6 OtherExtractionTechniques 161
7 Discussion 129 5 Conclusion 164
8 Conclusion 130 References 164
Acknowledgments 130
11. Total Polyphenols Content and
References 130
Antioxidant DPPH Assays on
9. Relevance and Analysis of Citrus Biological Samples 169
Flavonoids 133
VeronicaSandaChedeaandRalucaMariaPop
CarlosA.Ledesma-Escobar,FelicianoPriego-Capote 1 Introduction 169
andMarı´aD.LuquedeCastro
2 TheFolin-CiocalteuMethodorthe
1 Generalities 134 AssessmentofTotalPolyphenolsContent 170
2 NaturalOccurrenceofCitrusFlavonoids 134 2.1 InHumanPlasma 170
3 AnalysisofFlavonoids 136 2.2 InHumanUrine 170
4 SamplingMethodology 136 2.3 InCow’sPlasmaandMilk 176
5 SamplePretreatment 137 3 DPPHTest 176
6 ExperimentalDesignsUsedinCitrus 3.1 InPlasma:HumanandHorse 176
Studies 142 3.2 InInfantUrine 177
7 ExtractionMethods:EffectoftheAuxiliary 4 TotalPolyphenolsandAntioxidantActivity
Energies 143 Relationship 180
7.1 Ultrasound-AssistedExtraction 144 5 Conclusions 180
7.2 Microwave-AssistedExtraction 144 References 181
viii Contents
12. Extraction of Phenolic Compounds 14. Rice Phenolics: Extraction,
From L. and Characterization, and Utilization
Coriandrum sativum
L. by in Foods 217
Amaranthus hybridus
Microwave Technology 185
NopparatCheetangdee
DianaB.Mun˜iz-Ma´rquez,JorgeE.Wong-Paz, 1 Introduction 217
JuanC.Contreras-Esquivel,Rau´lRodriguez-Herrera
1.1 Phenolics 218
andCristo´balN.Aguilar
1.2 Flavonoids 218
1 Introduction 185 1.3 AnthocyaninsandProanthocyanidins 218
2 MaterialandMethods 186
1.4 TocopherolsandTocotrienols 218
2.1 PlantMaterialPreparation 186
1.5 SterylFerulate(g-Oryzanol) 218
2.2 Reagents 186
1.6 PhosphorusCompounds 219
2.3 ExtractionProcedure 186
2 ExtractionofPhenolicCompounds
2.4 PhenolicCompoundDetermination 186
FromRice 219
2.5 DPPH(1,1-Diphenyl-2-Picrylhydrazyl)
2.1 SolventExtraction 219
Radical-ScavengingAssay 186 2.2 Enzyme-AidedExtraction 221
2.6 HPLCAnalysis 187 2.3 Ultrasonic-AidedExtraction(UAE) 222
2.7 StatisticalAnalysis 187
2.4 Microwave-AssistedExtraction(MAE) 222
3 ResultsandDiscussion 187
2.5 SubcriticalWaterExtraction(SWE) 223
3.1 EffectsofExtractionConditionsBased
2.6 PressurizedLiquidExtraction 223
onPhenolicCompounds 187
3 CharacterizationofPhenolicsinRice 223
3.2 AntioxidantActivity 188
3.1 IntrinsicFactors 224
3.3 HPLCAnalysis 189
3.2 ExtrinsicFactors 226
4 Conclusions 189 4 UtilizationofRicePhenolicsinfoods 231
Acknowledgments 190 4.1 MeatProducts 232
References 190
4.2 FermentedFoods 233
4.3 Lipid-BasedFoods 233
13. Anthocyanins and Other Polyphenols
4.4 Carbohydrate-BasedFoods 234
in Genus: Biosynthesis,
Citrus 4.5 FruitsandVegetables 236
Chemical Profile, and Biological 5 Conclusions 236
Activity 191 References 237
GabrieleBallistreri,SimonaFabroni,FloraValeria
Romeo,NicolinaTimpanaro,MargheritaAmenta 15. Extraction of Polyphenols From
andPaoloRapisarda Aromatic and Medicinal Plants:
1 Introduction 191 An Overview of the Methods
2 AnthocyaninCompounds 192 and the Effect of Extraction
2.1 PhenolicCompounds 192 Parameters 243
3 BiosynthesisofAnthocyaninsandPhenolic
Compounds 194 AntigoniOreopoulou,DimitriosTsimogiannisand
VassilikiOreopoulou
4 AnthocyaninsinCitrusSpecies 197
4.1 PhenolicCompoundsinCitrusSpecies 198 1 Introduction 243
4.2 Oranges 202 2 AnOverviewofExtractionTechniques 243
4.3 MandarinsandTheirHybrids 204 2.1 ConventionalExtractionMethods 243
4.4 Lemon 209 2.2 NovelExtractionMethods 245
4.5 Limes 209 3 EffectofExtractionParameters 250
4.6 Grapefruit 209 3.1 ExtractionSolvent 250
4.7 Pummelo 209 3.2 pH 252
4.8 Citron 209 3.3 Temperature 253
4.9 BergamotandChinotto 210 3.4 ExtractionTime 253
5 BiologicalActivityofCitrusFlavonoidsand 3.5 Solvent-to-SolidRatio 254
OtherPhenolicCompounds 210 3.6 FactorsRelatedtotheRawMaterial 254
6 Conclusion 212 References 255
References 212 FurtherReading 259
Contents ix
Section C 3.3 HPLC-FTIRCoupling 322
3.4 HemoglobinWithAddedSchiffBase
Analysis Techniques for Polyphenols
LCFraction 323
4 Conclusions 324
16. Classification of Phenolic
References 324
Compounds in Plants 263
DimitriosTsimogiannisandVassilikiOreopoulou 19. Adsorption and Ion Exchange for
1 Introduction 263 the Recovery and Fractionation of
2 C PhenolicCompounds 263 Polyphenols: Principles and
6
3 C6-Cn(1≤n≤4)PhenolicCompounds 264 Applications 327
4 C6-Cn-C6(1≤n≤3,orn57)Phenolic
Compounds 266 DietmarRolfKammerer,JudithKammererand
4.1 Xanthonoids,Stilbenoids, ReinholdCarle
Anthraquinones,Anthrones,and 1 AdsorptionandIonExchangeTechnology:
DiarylHeptanoids 266 HistoricOverviewofItsApplication
4.2 C -C -C Phenolics:Flavonoids 267 Potential 327
6 3 6
5 PhenolicDimersandCondensation 2 AdsorbentandIonExchangeMaterials 327
OligomericProducts 274 3 PrinciplesofAdsorptionandIonExchange 329
6 PolymericPhenols(C ) ,(C -C ) ,and 4 KineticsandEquilibriaofSorptionandIon
6n 6 3n
(C6-C3-C6)n(n>12) 277 ExchangeProcesses 329
7 HybridPhenolics 278 5 PracticalImplementationofSorptionand
References 281 IonExchangeProcesses 330
6 ApplicationofAdsorptionandIonExchange
17. Gas Chromatography: Mass Technology 330
Spectrometry Analysis of 7 ApplicationofAdsorbentResinsandIon
Polyphenols in Foods 285 ExchangersfortheRecoveryofBio-and
TechnofunctionalPhenolicCompounds
PilarVin˜asandNataliaCampillo fromByproductsofFoodProcessing 332
1 PolyphenolicCompounds 285 References 336
2 PolyphenolicCompoundsinFoods 286
3 MethodsforDeterminingPolyphenols 287 20. HILIC Chromatography: Powerful
4 DeterminationofPolyphenolsbyGas
Technique in the Analysis of
Chromatography-MassSpectrometry
Polyphenols 341
(GC-MS).DerivatizationReactions 288
5 SamplePreparationTechniques 303
AleksandraSentkowskaandKrystynaPyrzynska
6 MiniaturizedTechniquesforSample
1 Introduction 341
PreparationInGC-MS 306
1.1 StationaryPhases 341
References 309
1.2 MobilePhases 342
1.3 Detection 347
18. Reaction of Hemoglobin With the
1.4 PracticalApplicationsofHILICMode 347
Schiff Base Intermediate of the
2 Conclusions 349
Glucose/Asparagine Reaction:
References 349
Formation of a Hemichrome 317
AristodimosIoannouandConstantinosVarotsis 21. Chromatographic Analysis of
Polyphenols 353
1 Introduction 317
2 MaterialsandMethods 318
KrystynaPyrzynskaandAleksandraSentkowska
2.1 Chemicals 318
2.2 SamplePreparation 318 1 Introduction 353
2.3 ExperimentalSetup 319 2 SamplePreparation 353
3 ResultsandDiscussion 320 3 ChromatographicAnalysis 355
3.1 HPLC 320 3.1 Detectors 355
3.2 ATR-FTIRSpectra 321 3.2 Columns 356