Phenolic Antioxidants in Foods: Chemistry, Biochemistry and Analysis

Preface
Acknowledgements
Contents
About the Author
Part I: Chemistry of Phenolic Antioxidants
Chapter 1: Concept of Antioxidants in Foods
	1.1 Introduction
	1.2 Concept of Antioxidant
	1.3 Types of Antioxidants
		1.3.1 Primary and Secondary Antioxidants
		1.3.2 Natural and Synthetic Antioxidants
		1.3.3 Enzymatic and Non-enzymatic Antioxidants
	1.4 Phenolic Antioxidants
	1.5 Mechanism of Antioxidant Action
		1.5.1 Hydrogen Atom Transfer
		1.5.2 Single Electron Transfer
		1.5.3 Sequential Proton Loss Electron Transfer
		1.5.4 Transition Metal Chelation
	1.6 Estimation of Antioxidant Activity
	1.7 Nomenclature of Phenolic Compounds
	1.8 Study Questions
	References
Chapter 2: Chemistry of Phenolic Antioxidants
	2.1 Introduction
	2.2 Classification
		2.2.1 Simple Phenols
		2.2.2 Hydroxybenzoic Acids
		2.2.3 Phenolic Aldehydes
		2.2.4 Acetophenone and Phenylacetic Acids
		2.2.5 Phenylethanoids
		2.2.6 Cinnamic Acids, Aldehydes and Alcohols
		2.2.7 Cinnamyl Esters
		2.2.8 Coumarins and Chromones
		2.2.9 Benzophenones and Xanthones
		2.2.10 Stilbenes
		2.2.11 Anthraquinones
		2.2.12 Chalcones
		2.2.13 Aurones
		2.2.14 Flavonoids
			2.2.14.1 Flavones
			2.2.14.2 Flavanones
			2.2.14.3 Flavonols
			2.2.14.4 Flavanols
			2.2.14.5 Flavanonols
			2.2.14.6 Isoflavones
			2.2.14.7 Neoflavones
		2.2.15 Anthocyanidins
			2.2.15.1 Leucoanthocyanidins
			2.2.15.2 Deoxyanthocyanidins
		2.2.16 Biflavonyls
		2.2.17 Betacyanins
		2.2.18 Lignans
		2.2.19 Lignins
		2.2.20 Tannins
			2.2.20.1 Condensed Tannins
			2.2.20.2 Hydrolysable Tannins
			2.2.20.3 Complex Tannins
		2.2.21 Phlobaphenes
		2.2.22 Glycosides
			2.2.22.1 Simple Phenol Glycosides
			2.2.22.2 Hydroxybenzoic Acid and Aldehyde Glycosides
			2.2.22.3 Acetophenone and Phenylacetic Acid Glycosides
			2.2.22.4 Phenylethanoid Glycosides
			2.2.22.5 Cinnamic Acid Glycosides
			2.2.22.6 Coumarin and Chromone Glycosides
			2.2.22.7 Benzophenone and Xanthone Glycosides
			2.2.22.8 Stilbene Glycosides
			2.2.22.9 Anthraquinone Glycosides
			2.2.22.10 Chalcone Glycosides
			2.2.22.11 Aurone Glycosides
			2.2.22.12 Flavonoid Glycosides
			2.2.22.13 Anthocyanidins Glycosides
			2.2.22.14 Lignan Glycosides
			2.2.22.15 Tannin Glycosides
	2.3 Physical Properties of Phenolic Compounds
		2.3.1 Melting Point
		2.3.2 Boiling Point
		2.3.3 Density
		2.3.4 Solubility
		2.3.5 Physical State
		2.3.6 Color
		2.3.7 Flavor and Aroma
	2.4 Chemical Properties of Phenolic Compounds
		2.4.1 Antioxidant Properties
		2.4.2 Acidity of Phenolic Compounds
		2.4.3 Metal Complexation
		2.4.4 Hydrogen Bonding
		2.4.5 Formation of Esters
		2.4.6 Glycosylation
		2.4.7 Ether Formation
		2.4.8 Oxidation of Phenolic Compounds
	2.5 Study Questions
	References
Chapter 3: Phenolic Antioxidants in Fruits
	3.1 Introduction
	3.2 Phenolic Antioxidants in Fruits
		3.2.1 Simple Phenols
		3.2.2 Hydroxybenzoic Acids
		3.2.3 Phenolic Aldehydes
		3.2.4 Acetophenone and Phenylacetic Acids
		3.2.5 Phenylethanoids in Fruits
		3.2.6 Cinnamic Acids and Its Derivatives
		3.2.7 Coumarins and Chromones
		3.2.8 Benzophenones and Xanthones
		3.2.9 Stilbenes
		3.2.10 Anthraquinones
		3.2.11 Flavonoids
		3.2.12 Anthocyanidins and Anthocyanins
		3.2.13 Tannins
		3.2.14 Glycosides
	3.3 Study Questions
	References
Chapter 4: Phenolic Antioxidants in Vegetables
	4.1 Introduction
	4.2 Phenolic Antioxidants in Vegetables
		4.2.1 Simple Phenols
		4.2.2 Hydroxybenzoic Acids and Aldehydes
		4.2.3 Cinnamic Acids, Aldehydes, Esters, and Alcohols
		4.2.4 Coumarins and Chromones
		4.2.5 Flavonoids
		4.2.6 Anthocyanins in Vegetables
	4.3 Study Questions
	References
Chapter 5: Phenolic Antioxidants in Cereals
	5.1 Introduction
	5.2 Phenolic Antioxidants in Cereals
		5.2.1 Hydroxybenzoic Acids and Aldehydes in Cereals
		5.2.2 Cinnamic Acids, Aldehydes, Esters, and Alcohols in Cereals
		5.2.3 Coumarins and Chromones in Cereals
		5.2.4 Flavonoids in Cereals
		5.2.5 Anthocyanins in Cereals
		5.2.6 Tannins in Cereals
	5.3 Study Questions
	References
Chapter 6: Phenolic Antioxidants in Legumes and Nuts
	6.1 Introduction
	6.2 Phenolic Antioxidants in Legumes
		6.2.1 Hydroxybenzoic Acids
		6.2.2 Hydroxycinnamic Acids
		6.2.3 Esters of Cinnamic Acids
		6.2.4 Stilbenes
		6.2.5 Flavonoids
		6.2.6 Catechins and Procyanidins
		6.2.7 Anthocyanidins and Anthocyanins
		6.2.8 Tannins
	6.3 Phenolic Antioxidants in Nuts
		6.3.1 Hydroxybenzoic Acids
		6.3.2 Hydroxycinnamic Acids
		6.3.3 Esters of Cinnamic Acids
		6.3.4 Stilbenes
		6.3.5 Flavonoids
		6.3.6 Anthocyanidins and Anthocyanins
		6.3.7 Tannins
		6.3.8 Phenolic Lignans
	6.4 Study Questions
	References
Chapter 7: Phenolic Antioxidants in Beverages
	7.1 Introduction
	7.2 Types of Beverages
	7.3 Phenolic Antioxidants in Beverages
		7.3.1 Simple phenols
		7.3.2 Hydroxybenzoic Acids
		7.3.3 Hydroxycinnamic Acids
		7.3.4 Esters of Cinnamic acids
		7.3.5 Stilbenes
		7.3.6 Flavonoids
		7.3.7 Anthocyanidins and Anthocyanins
		7.3.8 Tannins
	7.4 Study Questions
	References
Chapter 8: Phenolic Antioxidants in Herbs and Spices
	8.1 Introduction
	8.2 Phenolic Antioxidants in Herbs and Spices
		8.2.1 Simple Phenols
		8.2.2 Hydroxybenzoic Acids
		8.2.3 Hydroxycinnamic Acids
		8.2.4 Esters of Hydroxycinnamic Acids
		8.2.5 Curcuminoids
		8.2.6 Flavonoids
		8.2.7 Anthocyanidins and Anthocyanins
	8.3 Study Questions
	References
Chapter 9: Phenolic Antioxidants in Edible Oils
	9.1 Introduction
	9.2 Phenolic Antioxidants in Edible Oils
		9.2.1 Soybean Oil
			9.2.1.1 Simple Phenols
			9.2.1.2 Hydroxybenzoic Acids
			9.2.1.3 Hydroxycinnamic Acids
			9.2.1.4 Flavonoids
			9.2.1.5 Anthocyanins
		9.2.2 Olive Oil
			9.2.2.1 Simple Phenols
			9.2.2.2 Hydroxybenzoic Acids
			9.2.2.3 Phenylethanoids
			9.2.2.4 Hydroxycinnamic Acids
			9.2.2.5 Coumarins and Chromans
			9.2.2.6 Flavonoids
			9.2.2.7 Anthocyanins
			9.2.2.8 Lignans
		9.2.3 Brassica Oils
			9.2.3.1 Hydroxybenzoic Acids
			9.2.3.2 Hydroxycinnamic Acids
			9.2.3.3 Flavonoids
			9.2.3.4 Tannins
		9.2.4 Sunflower Oil
			9.2.4.1 Hydroxybenzoic Acids
			9.2.4.2 Phenylethanoids
			9.2.4.3 Hydroxycinnamic Acids
			9.2.4.4 Esters of Hydroxycinnamic Acids
			9.2.4.5 Flavonoids
		9.2.5 Flaxseed Oil
			9.2.5.1 Simple phenols
			9.2.5.2 Hydroxybenzoic Acids
			9.2.5.3 Hydroxycinnamic Acids
			9.2.5.4 Flavonoids
			9.2.5.5 Lignans
		9.2.6 Sesame Oil
			9.2.6.1 Simple Phenols
			9.2.6.2 Hydroxybenzoic Acids
			9.2.6.3 Hydroxycinnamic Acids
			9.2.6.4 Stilbenes
			9.2.6.5 Flavonoids
			9.2.6.6 Lignans
		9.2.7 Cottonseed Oil
		9.2.8 Palm Oil
	9.3 Study Questions
	References
Chapter 10: Phenolic Antioxidants in Dairy Products
	10.1 Introduction
	10.2 Phenolic Antioxidants in Dairy Products
		10.2.1 Simple Phenols
		10.2.2 Hydroxybenzoic Acids
		10.2.3 Hydroxycinnamic Acids
		10.2.4 Flavonoids
		10.2.5 Proanthocyanidin and Anthocyanidins
	10.3 Applications of Phenolic Antioxidants in Dairy Products
	10.4 Study Questions
	References
Part II: Biochemistry of Phenolic Antioxidants
Chapter 11: Biosynthesis of Phenolic Antioxidants
	11.1 Introduction
	11.2 Biosynthesis of Hydroxybenzoic Acids
		11.2.1 The Shikimate/Chorismate Pathway
		11.2.2 Biosynthesis of Gallic Acid
		11.2.3 Biosynthesis of Protocatechuic Acid
		11.2.4 Biosynthesis of Syringic Acid
	11.3 Biosynthesis of Hydroxycinnamic Acids
		11.3.1 Phenylpropanoid Pathway
		11.3.2 Biosynthesis of Salicylic Acid
	11.4 Biosynthesis of Phenolic Aldehydes and Alcohols
	11.5 Biosynthesis of Hydroxycinnamic Acid Esters
		11.5.1 Biosynthesis of Chlorogenic acids
	11.6 Biosynthesis of Coumarins
	11.7 Biosynthesis of Stilbenes
	11.8 Biosynthesis of Phenylethanoids
	11.9 Biosynthesis of Flavonoids
	11.10 Biosynthesis of Anthocyanidins
	11.11 Biosynthesis of Proanthocyanidins
	11.12 Biosynthesis of Tannins
	11.13 Biosynthesis of Lignans
	11.14 Biosynthesis of Glycosides
	11.15 Study Questions
	References
Chapter 12: Metabolism of Phenolic Antioxidants
	12.1 Introduction
	12.2 In-Vitro Metabolism of Phenolic Compounds
		12.2.1 Hydroxycinnamic Acids and Derivatives
		12.2.2 Stilbenes
		12.2.3 Flavonoids
		12.2.4 Anthocyanins
		12.2.5 Ellagitannins
	12.3 In-Vitro Metabolism of Phenolic Antioxidants
		12.3.1 Bioaccessibility
		12.3.2 Bioavailability, Release, and Absorption
		12.3.3 Metabolism
	12.4 Bioavailability of Phenolic Compounds in Humans
		12.4.1 Ingestion of Phenolic Compounds
		12.4.2 Digestion and Absorption
		12.4.3 Phenolic Compounds in the Bloodstream
	12.5 Metabolism of Phenolic Compounds in Humans
		12.5.1 Metabolism of Hydroxybenzoic Acids
		12.5.2 Metabolism of Hydroxycinnamic Acids
		12.5.3 Metabolism of Phenylethanoids
		12.5.4 Metabolism of Flavonoids
		12.5.5 Metabolism of Anthocyanins
		12.5.6 Metabolism of Tannins
	12.6 Interactions with Dietary Proteins
	12.7 Interactions with Carbohydrates
	12.8 Study Questions
	References
Chapter 13: Applications of Phenolic Antioxidants
	13.1 Introduction
	13.2 Applications of Phenolic Antioxidants in Foods
		13.2.1 As an Antioxidants in Foods
		13.2.2 Applications in Dairy Products
		13.2.3 As Food Additives
			13.2.3.1 Antimicrobial Food Additives
			13.2.3.2 Antioxidant Food Additives
		13.2.4 As Flavouring Agent in Foods
	13.3 Pharmacological Significance
	13.4 Health Applications of Phenolic Antioxidants
		13.4.1 Antibacterial Properties
		13.4.2 Anti-Hyperlipidemic Properties
		13.4.3 Cytotoxic, Anti-Tumor and and Anti-Cancer Properties
		13.4.4 Antioxidants Properties
		13.4.5 Cardio-Protective Properties
		13.4.6 Neuroprotective Properties
		13.4.7 In-Vitro and In-Vivo Anti-Diabetic Properties
	13.5 Oxidative Stress, Aging and Phenolic Antioxidants
		13.5.1 Oxidative Stress and Phenolic Antioxidants
		13.5.2 Aging and Phenolic Antioxidants
	13.6 Study Questions
	References
Chapter 14: Molecular Mechanism of Phenolic Antioxidants
	14.1 Introduction
	14.2 Basic Mechanism
	14.3 In-Vitro Studies
	14.4 In-Vivo Studies
	14.5 Phenolic Compounds and Oxidative Stress in Human
	14.6 Study Questions
	References
Part III: Analysis of Phenolic Antioxidants
Chapter 15: Basics in Analysis of Phenolic Antioxidants
	15.1 Introduction
	15.2 Extraction of Phenolic Compounds
		15.2.1 Ultrasound-Assisted Extraction (UAE)
		15.2.2 Microwave-Assisted Extraction (MAE)
		15.2.3 Ultrasound/Microwave-Assisted Extraction (UMAE)
		15.2.4 Ultrasound-Assisted Enzymatic Extraction (UAEE)
		15.2.5 Microwave-Assisted Enzymatic Extraction (MAEE)
		15.2.6 Supercritical Fluid Extraction (SFE)
		15.2.7 Subcritical Water Extraction (SCWE)
		15.2.8 High Hydrostatic Pressure Extraction (HHPE)
		15.2.9 Cyclodextrin-Assisted Extraction
	15.3 Spectrophotometric Analysis
		15.3.1 Folin–Ciocalteu Index (FCI)
		15.3.2 Total Phenolic Index (TPI)
		15.3.3 Determination of Flavonoid Contents
			15.3.3.1 Hydrochloric Acid Method
			15.3.3.2 pH Differential Method
			15.3.3.3 Bisulfite Degradation Method
			15.3.3.4 Co-Pigmentation Assay
		15.3.4 Determination of Proanthocyanins or Condensed Tannins
			15.3.4.1 Acid Hydrolysis Assay
			15.3.4.2 BSA Tannin Assay
			15.3.4.3 Cellulose Precipitable Tannin (MCP) Assay
	15.4 Potentiometric Methods
	15.5 Electrochemical Methods
		15.5.1 Cyclic Voltammetry
		15.5.2 Differential Pulse Voltammetry
		15.5.3 Square-Wave Voltammetry
		15.5.4 Amperometric Method
	15.6 Study Questions
	References
Chapter 16: Chromatography of Phenolic Antioxidants
	16.1 Introduction
	16.2 Types of Chromatography
	16.3 Thin Layer Chromatography
		16.3.1 Detection and Identification of Phenolic Compounds
		16.3.2 Applications of TLC
	16.4 Liquid Chromatography
		16.4.1 Types of Liquid Chromatography
			16.4.1.1 Reversed-Phase Chromatography
			16.4.1.2 Normal Phase Chromatography
			16.4.1.3 Ion Exchange Chromatography
			16.4.1.4 Size Exclusion Chromatography
		16.4.2 Stationary and Mobile Phases
		16.4.3 High Performance Liquid Chromatography
			16.4.3.1 HPLC Mobile Phases
			16.4.3.2 HPLC Stationary Phases
			16.4.3.3 HPLC Detectors
			16.4.3.4 Application of HPLC
		16.4.4 Ultra High-Pressure Liquid Chromatography
		16.4.5 Hydrophilic Interaction Liquid Chromatography
			16.4.5.1 Application of HILIC
	16.5 Gas Chromatography
		16.5.1 Derivatization of Phenolic Compounds
		16.5.2 GC Stationary Phases
		16.5.3 GC Detectors
		16.5.4 Applications of GC
	16.6 Study Questions
	References
Chapter 17: Spectroscopy of Phenolic Antioxidants
	17.1 Introduction
	17.2 Mass Spectrometry
		17.2.1 Instrumentation
		17.2.2 Applications of Mass Spectrometry
		17.2.3 Advantages of Mass Spectrometry
	17.3 Nuclear Magnetic Resonance Spectroscopy
		17.3.1 Instrumentation
		17.3.2 Applications of NMR
	17.4 Near-Infrared Spectroscopy
		17.4.1 Fundamentals
		17.4.2 Instrumentation
		17.4.3 Chemometrics
		17.4.4 Application of NIR Spectroscopy
		17.4.5 Advantages of NIR Spectroscopy
	17.5 Study Questions
	References
Index