Whole-Wheat Bread for Human Health

Yosef Dror • Ephraim Rimon • Reuben Vaida

Whole-Wheat Bread for Human Health

ISBN 978-3-030-39822-4 ISBN 978-3-030-39823-1 (eBook)https://doi.org/10.1007/978-3-030-39823-1

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Yosef DrorThe School of Nutritional Sciences The Faculty of AgricultureThe Hebrew University of JerusalemJerusalem, Israel

Reuben VaidaBSc Food Technologist Einat Food IndustriesRehovot, Israel

Ephraim RimonHead of the Gastro-Geriatric UnitKaplan-Harzfeld Medical CenterGedera, Israel

The Hebrew University of JerusalemJerusalem, Israel

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His Staple Highness – The Intact Kernel

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Preface

Whole wheat with high kernel envelope content and with relatively small endo-sperm was the main staple food and the main pillar of the Western civilization dur-ing the millennia when the Western civilization evolved. The plethora of anti-oxidant components that are mostly bound to carbohydrates and the related ingredients have protected and enabled the survival of wheat kernel and supported its spreading over the globe. With wheat cultivation, these compounds have sustained the human pop-ulation. However, during the long run of wheat breeding, wheat was selected for a higher kernel weight and a higher endosperm (starch) content, followed by an extreme decrease in the dietary fiber and a marked reduction in hundreds of com-pounds, maintaining the anti-oxidant capacity and other compounds with alleviative flour quality of health claim. Along with the history of wheat cultivation and har-vesting, wheat flour is consumed unrefined. Since the ancient eras, tiny amounts of wheat flour were refined to produce white flour with a higher quality of dough but with a lower nutritious quality. People have used to believe that white bread is most nutritious than the black whole bread. Such a notion is still believed.

The industrial revolution, at the second half of the nineteenth century, enabled mass refining of flour and drove more and more people to consume refined flour and throw away most of the nutritious ingredients embedded in the wheat bran for ani-mal feeding.

In the last two to three decades, the quality of dough and the baking quality of whole flour have tremendously improved by the introduction of a long list of baking improvers and baking technologies. Concomitantly, the nutritious predominance of the whole-wheat flour was gradually explored and published. Thus, the advantage of the whole bread has become a fundamental nutritional recommendation. Even so, whole bread consumption, in most of the countries, covers less than 20% of bread consumption.

The main target of the present book is to restore the consumption of the whole-wheat bread for the well-being of the people.

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The dietary fiber is considered as the major or the sole element supporting the health benefit of the whole bread. Indeed, adequate consumption of the whole bread accomplishes the prevailed inadequate dietary fiber intake. However, the dietary fiber is only part of the whole bread story since it contains a wide plethora of other ingredients and particularly the bound phenolic compounds found in high concen-tration in the whole bread.

The consumption of white bread has severely contradicted the food security fun-damental issue that is accepted by all health authorities. This book presents data concerning the composition and the average concentrations of hundreds of the ker-nel compounds gathered from over 210 publications with further description of these ingredients.

Except for the effect of the whole bread on the decrease in the incidence of the main morbidities, some other effects are described such as those of the yellow pig-ments on ophthalmologic burdens and various ingredients of the whole bread on the aging of cellular activities such as autophagy with its major role in the brain integrity.

Adherence to the gluten-free diet (GFD) is an important practice to prevent dam-age for the celiac wheat-sensitive people that comprise a small population segment (<1%). However, expanding of such practice for other people deprived them from the wide benefits of the wheat kernel and surges the dietary expenses. The descrip-tion of the celiac and the wheat sensitivity issues are also detailed here as well as the possible damage of the unnecessary use of GFD.

Industrial and the homemade whole wheat bread techniques with precise recipes are presented in the latter part of this book.

Jerusalem, Israel Yosef DrorGedera, Israel Ephraim RimonRehovot, Israel Reuben Vaida

As we clearly show (Chap. 15), the consumption of the whole bread lowers the incidence of many NCD (noncommunicable disease) very significantly. This impact is evaluated by 20 categories of morbidity and cause of mortality, including various vascular disorders and malignancy incidence, based on studies including more than 37 million subjects, within hundreds of studies around the globe.

Such an evidence-based effect, produced by consumption of one essential food has presumably never been previously shown. The facts presented here might help to convince health authorities to undertake active measures to recommend and enhance whole bread consumption.

We presume that beyond the reduction in the relative risk of morbidity and mor-tality, by a routine whole bread, it would also reduce the disability years of aging. Such a burden embraces a major load on the individual, his family, and the society which is estimated to have an average of 3 hard life years for each individual. The explanation for such an effect is described in details in this book.

The incidence for each of the 19 defined categories of morbidity and mor-tality has reduced by about 25% (relative risk of 0.75) in subjects con-sumed whole-wheat bread versus refined-flour bread.

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Starchy endosperm, storage and dead cells.

Compact 10 different layers of the envelope with the highestantioxidants content, dead cells.

3 cell layers of the endosperm termed the subaleurone with thehighest gluten content.

Monolayer of the aleurone, live cells.

Crease

A scheme of the longitudinal aspect of the wheat kernel. The embryo and the aleurone layer (green) are the only live kernel cells on dormancy. The envelop (red) that protects the kernel is a compact tissue composed of ten different layers that protect the kernel with the highest anti-oxi-dant content. The sub-aleurone layers (yellow) are part of the starchy endosperm and contain the highest gluten content that probably might have a role against the pests. These cells are “pris-matic,” while the “central” cells are more variable in shape. The white starchy endosperm layers compose the main kernel content. During grinding and refining, the sub-aleurone layer remained attached to the white flour while the aleurone layer leftover with the bran.

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Starchy endosperm.

Crease.

Compact 10 different layers of the envelope.

Subaleurone cells.

Aleurone.

A scheme of the transverse aspect of the wheat kernel. The crease area which is an important kernel area on its development, stays intact on the debranning phase during the initial grinding process.

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Contents

1 The Whole-Wheat Bread . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1The Early Exploration (Southern Western Area of the Lake of Galilee, Israel) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 9Continuous Pillar of the Civilization . . . . . . . . . . . . . . . . . . . . . . . . . . . 9The Main Global Grain Production (FAOSTAT) . . . . . . . . . . . . . . . . . . 9The Advantage of the Whole-Wheat Intake . . . . . . . . . . . . . . . . . . . . . . 10The Pitfall of the Refined-Bread Intake in the Scope of Other Nutritional Drawbacks . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 13The Motivation for the Consumption of Refined Wheat. . . . . . . . . . . . . 15The Industrial Baking . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 17The Marked Increase in Whole-Bread Quality . . . . . . . . . . . . . . . . . . . . 17References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 19

2 The Role of the Whole-Bread in the Nutrition Security . . . . . . . . . . 21The Foremost Misinterpretation in Human Nutrition . . . . . . . . . . . . . . . 23References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 24

3 The Wheat in the View of Our Whole-Menu . . . . . . . . . . . . . . . . . . . . 25The Exceptional Effect of the Whole-Wheat on Our Health . . . . . . . . . 25The Share of the Wheat in Our Menu . . . . . . . . . . . . . . . . . . . . . . . . . . . 27The Eternal Wheat Production . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 30The Global Production of the Main Carbohydrate Staple-Foods . . . . . . 31The Staple Foods . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 34The Starchy Foods . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 35The Soft and the Hard Wheat . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 35The Main Wheat Classes in the US . . . . . . . . . . . . . . . . . . . . . . . . . . . . 37The Common Wheat Products . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 38The Anatomy and the Ingredients of the Wheat Kernel . . . . . . . . . . . . . 39References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 41

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4 The Milling and the Refining . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 43The Milling . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 43

The Kernel Hardness . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 46The Jet Milling . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 47

The Flour Refining . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 49The Effect of the Extraction Rate on the Phytochemicals . . . . . . . . . 54The Effect of the Flour Refining on the Anti-Oxidant Capacity of the Bread . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 56

The Milling Yield (Extraction Rate) . . . . . . . . . . . . . . . . . . . . . . . . . . . . 58Starch Deformation (Damaged Starch) . . . . . . . . . . . . . . . . . . . . . . . . . . 58The Destruction of the Precious Nutritional and the Vulnerable Ingredients of the Whole-Wheat . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 60References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 61

5 The Kernel Organs and Composition . . . . . . . . . . . . . . . . . . . . . . . . . 65The Bran . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 66The Germ (the Kernel Embryo) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 68The Nucellus . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 69The Testa . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 69The Pericarp . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 69The Endosperm . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 69

The Aleurone . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 70The Sub-Aleurone Cells . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 70The Starchy Endosperm . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 71

The Major Ingredients . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 71Nutrients in the Wheat-Kernel Not Considered by the RDA as Essential Ingredients . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 72The Kernel Composition: Proteins, Lipids, and Minerals . . . . . . . . . . . 74

The Wheat Proteins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 75The Wheat Gluten . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 77Gluten Has a Biologic Functioning in Plant Biology Rather Than Coined As a Storage Protein . . . . . . . . . . . . . . . . . . . . . 79The Gliadins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 80The Glutenin . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 80The Friabilin . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 80The Wheat Globulin . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 81The Vital Gluten . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 81

The Amino Acids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 82The Wheat Kernel Lipids (Table 5.4) . . . . . . . . . . . . . . . . . . . . . . . . . . . 83The Wheat Kernel Minerals . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 86References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 88

6 The Wheat Carbohydrates . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 91The Starch . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 95The Glycemic Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 100

The Hexose . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 101Glucose . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 101

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Some Other Hexoses that Found in the Wheat Kernel . . . . . . . . . . . . . . 102The Nonstarch Polysaccharides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 102

References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 102

7 The Dietary Fiber . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 105The Dietary Fiber Definition . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 105The Fermentability . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 107The Dietary Fiber in Human Nutrition . . . . . . . . . . . . . . . . . . . . . . . . . . 109The Types of Dietary Fiber . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 111The Dietary Fiber Precursors (Building Blocks) . . . . . . . . . . . . . . . . . . 115

Pentose . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 115Xylose . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 117

The Dietary Fiber Polymers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 117The Arabinoxylan . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 119The Effect of the Arabinoxylan on the Dough Rising . . . . . . . . . . . . 120Glucomannan . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 121The Resistant Starch . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 121The Cellulose . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 122The Hemicellulose . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 122

The Unique Building Blocks of the Lignin . . . . . . . . . . . . . . . . . . . . . . . 124The Uronic Acids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 126Iduronic Acid . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 126

The Lignocellulose . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 126The Inulin . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 127The Energy Extraction from the Dietary Fiber by the Colon . . . . . . . . . 128The Evaluation of the Nutritive Quality of the Dietary Fiber . . . . . . . . . 130The Dietary Fiber Digestion in the Herbivores . . . . . . . . . . . . . . . . . . . . 132References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 133

8 The Vitamins and the Organic Micronutrients in the Wheat Kernel . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 137The Vitamins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 141Other Organic Micro-ingredients . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 142The Glutathione . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 145The Tocols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 148

The Tocotrienols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 149The Tocopherols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 150

The Carotenoids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 152The Xanthophylls . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 156The Lutein . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 156The Methyl Donors . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 159

The Choline . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 161The Betaine . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 163The Dimethylglycine . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 164The Trigonelline . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 166

References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 167

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9 The Anti-oxidants . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 173Reactive Oxygen Species (ROS). . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 174The Sterols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 175The Stanols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 177The Role of the Phenolic Acids in the Plant Survival . . . . . . . . . . . . . . . 178The Phenolic Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 179

Phenylpropiolic Acid . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 183Specific Phenolic Acids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 183

The Tannins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 186The Flavonoids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 190The Interactions of the Wheat Anti-oxidants in the Gut . . . . . . . . . . . . . 191The Lignans . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 193The Benzoxazinoids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 197The Alkylresorcinol . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 198

The Biomarker Role of the Alkylresorcinols . . . . . . . . . . . . . . . . . . . 200DHPPA . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 202

The Biological Activity of the Anti-oxidants . . . . . . . . . . . . . . . . . . . . . 203The Secondary Metabolites . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 205

The Controversial Issue of the External Anti-oxidants Supplementation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 207The Variability in the Phenolics Concentrations Between the Wheat Cultivars . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 209References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 210

10 The Anti-oxidant Capacity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 217Measuring of the Anti-oxidant Capacity . . . . . . . . . . . . . . . . . . . . . . . . . 217The Enzymatic Inhibition of the Yeast Activity . . . . . . . . . . . . . . . . . . . 218The Anti-oxidants Destruction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 220The Bread Anti-oxidant Capacity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 221The Human Blood Anti-oxidants . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 222The Contribution of the Whole-Bread Intake to the Daily Balance of the Polyphenols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 224References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 224

11 The Ingredients of the Covering Layers . . . . . . . . . . . . . . . . . . . . . . . 227The Policosanol . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 228The Cutin . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 229The Suberin . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 229References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 230

12 The Wheat-Kernel Ingredients with Dichotomic Physiological Activities . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 231The Phytic Acid . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 231The Alleviated Outcomes of the Phytic Acid Intake . . . . . . . . . . . . . . . . 235The Phytase . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 236The Oxalic Acid . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 236References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 238

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13 A Trend in the Decrease in the Wheat Consumption . . . . . . . . . . . . . 241Changes in the Wheat Intake in Selected Countries . . . . . . . . . . . . . . . . 241The Whole-Wheat Intake in Various Countries . . . . . . . . . . . . . . . . . . . 245The Consumer Preference . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 247Non-celiac Gluten Sensitivity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 248Epidemiology . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 248Pathophysiology . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 249The Non-gluten Proteins of the Wheat Kernel . . . . . . . . . . . . . . . . . . . . 250Clinical Manifestations . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 250Diagnosis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 251Management . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 253Gluten and Celiac Disease (Gluten-Sensitive Enteropathy) . . . . . . . . . . 254Wheat Germ Agglutinin (WGA) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 255The Wheat Free-Diet . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 256Gluten Free Diet (GFD) Pricing and Advertising . . . . . . . . . . . . . . . . . . 258The Oats . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 259The Low Carbohydrate Diet . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 260References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 261

14 Digestion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 267The Colon Deverticula and Polyps . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 274

The Diverticulosis Burden Terms . . . . . . . . . . . . . . . . . . . . . . . . . . . . 276The Digesta Flow . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 279

The Colon Activity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 282Digestion of the Phenolic Compounds . . . . . . . . . . . . . . . . . . . . . . . . 283

The Bile Acids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 284The Bile Acids and the Whole-Wheat Interaction . . . . . . . . . . . . . . . . . 290The Bread Digestion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 292The Terminal Ileum Is the Main Site Control of the Gut Activity . . . . . 293References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 295

15 The Health Impact of the Whole-Wheat Intake as Evaluated by Wide- Scaled Epidemiological Studies . . . . . . . . . . . . . . . . . . . . . . 301The Decrease in the Non-communicable Diseases by the Consumption of the Whole-Wheat Bread . . . . . . . . . . . . . . . . . . 301The Critical Role of the Large Numbers . . . . . . . . . . . . . . . . . . . . . . . . . 302The Obstacles to the Investigation of the Effect of the Whole- Wheat Intake . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 310The Effects of the Whole-Wheat Intake on the NCD (Non- communicable Diseases) in Wide Scaled Studies . . . . . . . . . . . . . 310Detailed Description of the Effects of the Whole-Wheat Intake on the Discrete Burdens . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 313

The Incidence of the Colorectal Malignancy (Table 15.1, Category 1) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 313The Incidence of the Upper Gut Malignancy (Table 15.1, Category 2) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 319

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The Incidence of the Pancreatic Malignancy (Table 15.1, Category 3) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 320The Incidence of Breast Cancer (Table 15.1, Category 4) . . . . . . . . . 321The Incidence of the Ovarian Malignancy (Table 15.1, Category 5) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 322The Incidence of the Hepatocellular Carcinoma (Table 15.1, Category 6) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 323The Incidence of the All-Cause of Malignancy (Table 15.1, Category 7) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 323The Incidence of Cardiovascular Morbidity (Table 15.1, Category 8) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 323The Incidence of Stroke (Table 15.1, Category 9) . . . . . . . . . . . . . . . 324The Incidence of Hypertension (Table 15.1, Category 10) . . . . . . . . . 325The Incidence of Diabetes Type 2 (Table 15.1, Category 11) . . . . . . . 326The Incidence of Metabolic Syndrome (Table 15.1, Category 12) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 329The Incidence of the Hip Fracture (Table 15.1, Category 13) . . . . . . 330The Incidence of the Mortality Attributed to Malignancy (Table 15.1, Category 14) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 330The Incidence of Mortality Attributed to Cardiovascular Diseases (Table 15.1, Category 15) . . . . . . . . . . . . . . . . . . . . . . . . . . 331The Incidence of the Mortality Attributed to Stroke (Table 15.1, Category 16) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 331The Incidence of the Mortality Attributed to Diabetes Type 2 (Table 15.1, Category 17) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 332The Incidence of the Mortality Attributed to Inflammatory Diseases (Table 15.1, Category 18) . . . . . . . . . . . . . . . . . . . . . . . . . . 332The Incidence of the Mortality Attributed to Respiratory Diseases (Table 15.1, Category 19) . . . . . . . . . . . . . . . . . . . . . . . . . . 333The Incidence of the All-Cause of Mortality (Table 15.1, Category 20) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 334

References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 335

16 Observational Studies on Law Scale Experimentations . . . . . . . . . . 347The Effect of the Whole-Wheat on the Adiposity Incidence . . . . . . . . . 347The Effect of the Whole-Wheat Intake on the Carotid Intima- Media Thickness (IMT) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 349The Effect of the Whole-Wheat Intake on the Angiography Indications . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 350A Continuous Model Showed by a Meta-Analysis for the Effect of Whole- Grain Intake on the Relative Risk of Main Burdens . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 350References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 351

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17 Intervention and Biomarkers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 353Interventional Studies . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 353The Fecal Output . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 354The Blood Alkylresorcinol as a Biomarker for the Whole- Wheat Intake . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 355DHPPA as Advanced Biomarker. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 358The Direct Effects of Alkylresorcinol . . . . . . . . . . . . . . . . . . . . . . . . . . . 359References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 360

18 The Effect of the Yellow Pigments on the Ocular Functions, the Effect on the Cognition, and the Development . . . . . . . . . . . . . . 363Age-Related Macular Degeneration (AMD). . . . . . . . . . . . . . . . . . . . . . 366The Effect on the Cataract . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 368Glaucoma and the Diabetic Retinopathy . . . . . . . . . . . . . . . . . . . . . . . . 370The Effect of the Yellow Pigments on the Cognition . . . . . . . . . . . . . . . 370The Effect on the Early Development . . . . . . . . . . . . . . . . . . . . . . . . . . . 373References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 374

19 The Whole-Wheat Effect on Cellular Activities That Support Aging . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 377The Effect of Dietary Fiber and the Anti-oxidant Intake on the Moderation of the Telomere Attrition and Aging . . . . . . . . . . . . . 377A Possible Effect of the Whole-Bread Ingredients on the Dynamics of the Autophagy and Apoptosis . . . . . . . . . . . . . . . . . 379The Effect on Cognition . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 381References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 383

20 The Effect of the Starchy Staple Foods on the Wheat Consumption . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 385Potato Versus Wheat Consumption . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 385The Anti-oxidant Content of the Kernel Corn (Maize) . . . . . . . . . . . . . . 385References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 387

21 The Ready-to-Eat Cereals (RTEC) . . . . . . . . . . . . . . . . . . . . . . . . . . . 389The Extent of the RTEC Consumption . . . . . . . . . . . . . . . . . . . . . . . . . . 390The Effect of the Consumption of the RTEC on the Morbidity and the Mortality . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 391References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 393

22 Malpractice in the Bread Baking . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 395Admixing of Preparatory Fibers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 396Flour Milling Failure . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 397Salt Excess . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 397The Adverse Fabrication of the Acrylamide . . . . . . . . . . . . . . . . . . . . . . 399References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 400

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23 The Whole-Rice Consumption . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 401The Current Rice Consumption . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 401The Wheat Versus Rice Nutritional Quality . . . . . . . . . . . . . . . . . . . . . . 405The Advantage of the Brown (Whole) Rice . . . . . . . . . . . . . . . . . . . . . . 405References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 406

24 The Bread Consumption . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 409The Intake of the Whole-Grain in Some Countries . . . . . . . . . . . . . . . . 409The Promotion of the Whole-Wheat Bread Intake . . . . . . . . . . . . . . . . . 410

The Major Impairment in the Implementation of the Whole- Bread as the Major Staple Food . . . . . . . . . . . . . . . . . . 412

References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 413

25 Industrial and Home-Made Baking of the Whole-Wheat Bread . . . 415The Ingredients for the Whole-Wheat Bread Production . . . . . . . . . . . . 417Classification of the Dough Ingredients . . . . . . . . . . . . . . . . . . . . . . . . . 417Industrial Processing and Baking of the Whole-Wheat . . . . . . . . . . . . . 420Home-Made Processing and Baking of the Whole-Wheat . . . . . . . . . . . 421Other Whole-Wheat Flour Bakery Products . . . . . . . . . . . . . . . . . . . . . . 422The Whole-Wheat Bread Advantage . . . . . . . . . . . . . . . . . . . . . . . . . . . 422Bread Toasting . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 423References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 424

Appendix 1 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 425

Appendix 2 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 443

Definitions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 445

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List of Figures

Fig. 1.1 Four specimens from the wheat cultures of human civilization (~15–7.5 kya) excavated on sites at the upper areas of the Jorden valley Israel. (Courtesy of The Israel Museum) . . . . . . . . . . . . . . . . . . . . . . . . . . . . 10

Fig. 3.1 The old chessboard and the wheat tale . . . . . . . . . . . . . . . . . . . . . . . . 30Fig. 3.2 The main cereal grains with the indication of the grain

weight (mg) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 36

Fig. 4.1 Refined and whole-wheat flour . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 49Fig. 4.2 The industrial revolution and the milling machine . . . . . . . . . . . . . . . 50Fig. 4.3 The mineral and vitamin content versus the flour extraction

rate. The following concentrations were measured for the unrefined flour, %: ash 1.8; protein 14.2; fat 2.7; starch and sugar 70; dietary fiber 12.1; mg/g - calcium 0.44; phosphorous 3.8; μg/g – zinc 29, copper 4; iron 35; thiamin (B1) 5.8; riboflavin (B2) 0.95; pyridoxin (B6) 3.5; folic acid 0.57; niacin 25.2; biotin 0.01 (Slavin et al. 2001) . . . . . . . . 53

Fig. 4.4 The concentration of the anti-oxidant phenol compounds versus the extraction rate (Wang et al. 2013) . . . . . . . . . . . . . . . . . . . . 54

Fig. 4.5 The bound and the free phenolics versus the extraction rate; red line – total phenolic acids; black line – free phenolic acids (Wang et al. 2013) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 55

Fig. 4.6 Trolox and DPPH. (a) Trolox: Aromatic compounds of a bicyclic compound made up of a benzene ring fused to a pyran so that the oxygen atom is at the 1-position. An anti-oxidant used in the food industry (HMDB). (b) DPPH: An abbreviation for the chemical compound 2,2-diphenyl-1- picrylhydrazyl. Used to monitor the anti-oxidant content . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 57

xxii

Fig. 5.1 α-linoleic acid (C18:2), shown in two graphical presentations. α-linoleicn for linoleic acid is a doubly unsaturated fatty acid, also known as an omega-6 fatty acid, occurring widely in plant lipids. In this particular polyunsaturated fatty acid (PUFA), the first double bond is located between the 6th and 7th carbon atom from the methyl end of the fatty acid (n-6). Linoleic acid is an essential fatty acid in human nutrition because it cannot be synthesized by human tissues. It is used in the biosynthesis of prostaglandins (via arachidonic acid) and cell membranes (HMDB) . . . . . . . . . . . . . . . . . . . . . . . . . . . 85

Fig. 5.2 α-linolenic acid (C18:3), shown in two graphical presentations. α-linolenic acid (ALA) is a polyunsaturated fatty acid (PUFA) with 3 double bonds (unsaturated). It is a member of the group of essential fatty acids called ω-3 fatty acids. α-linolenic acid, in particular, is not synthesized by mammals and therefore is an essential dietary requirement. The ω-3 fatty acids get their name based on the location of one of their first double bond. In all ω-3 fatty acids, the first double bond is located between the third and fourth carbon atom counting from the methyl end of the fatty acid (n-3). Although humans and other mammals can synthesize saturated and some monounsaturated fatty acids from carbon groups in carbohydrates and proteins, they lack the enzymes necessary to insert a cis double bond at the n-6 or the n-3 position of a fatty acid. ω-3 fatty acids like α-linolenic acid are important structural components of cell membranes. When incorporated into phospholipids, they affect cell membrane properties such as fluidity, flexibility, permeability and the activity of membrane-bound enzymes. Linoleic acid is an essential fatty acid that must derive from food for proper health (HMDB) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 86

Fig. 6.1 The glucose which composes the building block of the starch, glycogen, and the cellulose and other polymers, shown in two graphical presentations. D-Glucose is a monosaccharide containing six carbon atoms with an aldehyde group and therefore referred to as an aldohexose. The glucose molecule can exist in an open-chained (acyclic) and ring (cyclic) form, the latter being the result of an intramolecular reaction between the aldehyde C atom and the C-5 hydroxyl group to form an intramolecular hemiacetal. In water solution, both forms are in equilibrium and at pH 7 the cyclic one is predominant. The glucose is a primary source of energy for the living organisms. It is naturally occurring and found in fruits and other parts of the plants in its free state. In the animals, the glucose arises from the breakdown of glycogen. The glucose synthesized in the liver and the kidneys from

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non-carbohydrate intermediates, such as pyruvate and glycerol, by a process known as gluconeogenesis. The starch composes entirely from the glucose (Bertoft 2017). Water solubility 1.2 g/mL; density 1.54 g/mL . . . . . . . . . . . . . . . . . . . 94

Fig. 6.2 The amylose. The amylose defined as a linear molecule of (1→4) linked α-D- glucopyranosyl units but is well established that some molecules are slightly branched by the (1→6)-α-linkages. The oldest criteria for the linearity consisted of the susceptibility of the molecule to complete hydrolysis by the β-amylase. This enzyme splits the (1→4) bonds from the non- reducing end of a chain releasing the β-maltosyl units but cannot cleave the (1→6) bonds. When degraded by pure β-amylase, linear macromolecules completely converted into maltose, whereas branched chains give also one β-limit dextrin consisting of the remaining inner core polysaccharide structure with its outer chains recessed. The starches of the different botanical origins possess different granular sizes, morphology, polymorphism, and enzyme digestibility. These characteristics related to the chemical structures of the amylopectin and the amylose and their arrangement in the starch granule (HMDB) . . . . . . 95

Fig. 6.3 The amylopectin is a highly branched polymer of the glucose found in the plants. It is one of the two components of the starch, the other being amylose. It is insoluble in water. The glucose units linked linearly way with α-(1→4) bonds. The branching takes place with α-(1→6) bonds occurring every 24–30 glucose units. Its counterpart in the animals is glycogen that has the same general composition and structure, but with more extensive branching. The branching occurs every 8–12 glucose units. The starch is made of about 80% amylopectin. The amylopectin is highly branched, formed of 2,000–200,000 glucose units. Its inner chains formed of 20–24 glucose subunits. The glucose residues are linked through α-1,4 glycosidic linkages (HMDB) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 96

Fig. 6.4 Maltose and maltotriose. (a) D-Maltose or malt sugar, is a primary disaccharide in the human diet formed from two units of glucose joined with an α (1→4) linkage. It is the second member of an important biochemical series of glucose chains. The addition of another glucose unit yields maltotriose, further additions will produce dextrins, also called maltodextrins, and eventually starch. Maltose can be broken down into two glucose molecules by hydrolysis in living organisms. At the surface of the small intestine, the brush border enzymes maltase breaks down maltose (HMDB). (b) Maltotriose: A common oligosaccharide metabolite found in human urine after maltose ingestion or infusion (HMDB) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 97

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Fig. 6.5 Galactose, mannose, and fructose (gray, red and white balls are carbon, oxygen, and hydrogen, respectively) (Wikipedia), shown in two graphical presentations. (a) β-D-galactose is an aldohexose that occurs naturally in the D-form in lactose, cerebrosides, gangliosides, and mucoproteins. The D-galactose is an energy-providing nutrient and a necessary basic substrate for the biosynthesis of many macromolecules in the body. The metabolic pathways for the D-galactose are important not only for the provision of these pathways but also for the prevention of the D-galactose and the D-galactose metabolite accumulation. (b) D-Mannose: A high-mannose-type oligosaccharides have shown to play important roles in the protein quality control. (c) D-fructose, or levulose, is an isomer of glucose. Fructose is the sweetest naturally occurring sugar, estimated to be twice as sweet as sucrose with a “fruity” aroma. Although the fructose is a hexose, it generally exists as a 5-member hemiketal ring (a furanose that is responsible for the long metabolic pathway and high reactivity) compared to glucose. It used as a preservative and an intravenous infusion in parenteral feeding . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 98

Fig. 7.1 The lignin precursors, the lignin building blocks (shikimic acid, coniferyl alcohol, 4- coumaryl alcohol, sinapyl alcohol) (gray, red and white balls are carbon, oxygen, and hydrogen, respectively), shown for the schikemic acid in two graphical presentations. (a) Shikimic acid is a precursor for the lignin biosynthesis. Shikimic acid, (the anionic form shikimate), is a biochemical intermediate in the plants and the microorganisms. It is a precursor for phenylalanine, tyrosine, tryptophan, indole derivatives, alkaloids, and other aromatic metabolites. The shikimic acid used commercially as a base material for the production of the Tamiflu drug. (b) Coniferyl alcohol is a precursor for the lignin biosynthesis. (c) 4-Coumaryl alcohol is a precursor for the lignin biosynthesis. (d) Sinapyl alcohol is a precursor for the lignin biosynthesis . . . . . . . . . . . . . . . . . . . . . . 112

Fig. 7.2 The cellulose structure. The cellulose is a polysaccharide consisting of a linear chain of several hundred to many thousands of β(1→4) linked D-glucose units with the formula (C6H10O5)n. The cellulose is an important structural component of the primary cell wall of green plants, many forms of the algae and the oomycetes. Some species of bacteria secrete it to form biofilms. The cellulose content of the cotton fiber is 90%, and that of the wood is 40–50% (Wikipedia). . . . . . . . . . . . . . . . . . . 113

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Fig. 7.3 Metabolites of the hemicelullose (HMDB). (a) 4-O-Methyl-a-D-glucosyl-(1→2)-b-D- xylosyl- (1→4)-D-xylose. (b) 2-O-b-D-Xylopyranosyl-L-arabinose is found in cereals and cereal products. (c) 4-O-Methyl- a-D-glucosyl-(1→2)-b-D-xylosyl-(1→4)-D-xylose is found in cereals and cereal products. 4-O-Methyl-a-D-glucosyl- (1→2)-b-D-xylosyl-(1→4)-D-xylose is from oat hull hemicelluloses. (d) Aldobiouronic acid D3 is found in cereals and cereal products. Aldobiouronic acid D3 is isolated from }partial acid hydrolysates of gum chagual (Puya species) and the hemicelluloses from corn hulls and wheat bran . . . . . . . . . . 114

Fig. 7.4 The α- and β-glycoside bonds of the glucose polymers. The difference between the two bond-types encircled in red. (a) β-glycoside bonds, cellulose made up of β-glucose bonds. (b) α-glycoside bonds, the starch made up of α-glucose bonds . . . . . 115

Fig. 7.5 Rhamnose, xylose, and arabinose (gray, red and white balls are carbon, oxygen, and hydrogen, respectively) (Wikipedia), shown in two graphical presentations. (a) L-Rhamnose: A methyl-pentose where the L-isomer found naturally in many plant glycosides. (b) Xylose or the wood sugar is an aldopentose - a monosaccharide containing five carbon atoms and an aldehyde functional group. It is 40% as sweet as the sucrose. The xyloses found in the embryos of most edible plants. The polysaccharide xylan closely associated with the cellulose consists practically entirely of the D-xylose. The corncobs, cottonseed hulls, pecan shells, and the straw contain considerable amounts of this sugar. The xylose also found in the mucopolysaccharides of the connective tissues and sometimes in the urine. The xylose is the first sugar added to the serine or the threonine residues during the proteoglycan type O-glycosylation. (c) D-Arabinose found in sweet basil. The arabinose is an aldopentose a monosaccharide containing five carbon atoms, and including an aldehyde (CHO) functional group. The arabinose belongs to the family of the pentoses. (d) L-Arabinose is a pentose with a sweet taste and one of the most abundant components of non-starch polysaccharides of the vegetable origin. A portion of the ingested L-arabinose excreted in the urine. L-arabinose is rarely used, and its physiological effects in vivo have received little attention . . . . . . . . 116

Fig. 7.6 Arabinoxylan . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 118Fig. 7.7 The ferulic acid linked to D-xylopyranosyl

(Courtin and Delcour 2002). http://www.ethanolproducer.com/ article.jsp?article_id=4160 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 118

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Fig. 7.8 Glucuronic acid is a typical building block of the hemicellulose precursor (gray, red and white balls are carbon, oxygen, and hydrogen, respectively) (Wikipedia), shown in two graphical presentations. The glucuronic acid is a carboxylic acid that has the structure of a glucose molecule that has had its 6th carbon atom oxidized. The glucuronic salts termed glucuronates. In the animal body, the glucuronic acid often linked to poisonous substances to allow for subsequent elimination, and to hormones to allow for easier transport. . . . . . . . . 123

Fig. 7.9 Scheme of the lignin structure (Wikipedia). . . . . . . . . . . . . . . . . . . . 125Fig. 7.10 Iduronic acid . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 127Fig. 7.11 The inulin is a soluble dietary fiber. It is a naturally

occurring oligosaccharide composed mainly of the fructans. The non-digestible inulin passes through the small intestine and fermented in the colon. The plant inulins contain between 20 to several thousand fructose units. Inulin is naturally present in many foods. Chicory root is the most common source of the inulin due to its extremely high concentration as well as its similarities to the sugar beet. Inulin has several health benefits. This dietary fiber used as a prebiotic agent in functional foods to stimulate the growth of beneficial intestinal bacteria (HMDB) . . . . . 128

Fig. 7.12 The fructooligosaccharides (FOS) considered as one of the main group of the prebiotics that has recognized as bifidogenic properties. The FOSs are obtained either by the extraction from various plant materials or by the enzymatic synthesis from different substrates. Enzymatically, these can obtain either from the sucrose using fructosyltransferase or from inulin by the endoinulinase. The inulin is a potent substrate for the enzymatic production of the FOSs (Singh et al. 2016) . . . . . . . . 130

Fig. 8.1 The glutathione, shown in two graphical presentations. Glutathione is an iso-tripeptide (GSH, γ-L-glutamyl-L-cysteinyl- L-glycine), a low molecular weight, and a water-soluble thiol compound that is distributed widely in nature. The sulfhydryl group (SH) of the reduced glutathione (GSH) can easily oxidize to the disulfide bond (SS), forming the oxidized glutathione (GSSG) and the protein-bound glutathione under the anaerobic condition or catalyzed by glutathione dehydrogenase. Thus, glutathione exists naturally in GSH, GSSG, and protein-S-SG (PSSG) forms. Furthermore, there are three thiol compounds, i.e. L-cysteine (Cys), L-glutamyl-L-cysteine (Glu- Cys) and L-cysteinyl-L-glycine (Cys-Gly), occurring as intermediates in the glutathione synthesis pathway, all of which possess an SH group. Glutathione synthesized from cysteine, perhaps the most important member of the body’s toxic waste disposal team.

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Like the cysteine, the glutathione contains the crucial thiol (-SH) group that makes it an effective anti-oxidant. The most important of these are the redox reactions, in which the thiol grouping on the cysteine portion of cell membranes protects against peroxidation; and conjugation reactions, in which GSH binds with toxic chemicals to detoxify them. Apart from the role in storage and transport of reduced sulfur glutathione takes part in the detoxification of reactive oxygen species, directly or indirectly acting in the reactive oxygen species detoxification, glutathione participates in methylglyoxal detoxification. It acts as a cofactor in different biochemical reactions, it interacts with hormones, signaling molecules, and its redox state triggers signal transduction. Glutathione modulates cell proliferation, apoptosis, fibrogenesis, growth, development, the cell cycle, gene expression, protein activity, and immune function (Hasanuzzaman et al. 2017). It is a coenzyme in various enzymatic reactions. The GSH is a cofactor for the enzyme GSH peroxidase (HMDB) . . . . . . . . . . . . . . . . . . . . . . . 146

Fig. 8.2 The tocols that comprise: α-tocopherol has a saturated side chain while α-tocotrienol has a side chain with 3 unsaturated bonds. Each group contains 4 isomers. The scheme depicts the differences between the α-tocopherol (without 3 double bonds in the side chain), on the left, and the α-tocotrienol (that contains 3 double bonds in the side chain), on the right side of the scheme. Each of these 2 molecules might have 4 substitutions on position R1 or position R2. Each of these 8 forms might pose a slightly different activity and role in the total anti-oxidant capacity, The α-tocotrienol found in the blood plasma and all lipoprotein subfractions and traditionally recognized as the most active form of vitamin E in humans and is a powerful biological anti-oxidant. Compared to the tocopherols, the α-tocotrienols are poorly studied. Its presence in the blood plasma at nM (nanomolar) concentrations thought to help to prevent stroke-related neurodegeneration. The α-tocotrienol has found to have vitamin E activity (HMBD). The total tocopherols and the total tocotrienols in the wheat kernel are 30 and 22 μg/g respectively (Table 8.3) . . . . . . . . . . . . . . . . . . . . . . . . . 149

Fig. 8.3 The β-carotene (content in wheat kernel 0.1 μg/g), shown in two graphical presentations. The β-carotene is a carotenoid that is a precursor of retinol. Carotene is an orange photosynthetic pigment. It is responsible for the orange color of the carrot and many other fruits and vegetables. It contributes to photosynthesis by transmitting the light energy it absorbs to chlorophyll. Chemically, carotene is a terpene. It is the dimer of retinol

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and comes in 2 main primary forms: α- and β-carotene, and also γ-, δ- and ε-carotenes. Carotene can be stored in the liver and converted into retinol as needed. The β-carotene is an anti-oxidant and such can be useful for curbing the excess of damaging free radicals in the body. However, the usefulness of β-carotene as a dietary supplement (taken as a pill) is still subject to debate. The β-carotene is fat-soluble, so a small amount of fat needed to absorb it into the body . . . . . . . . . . . . . . . . . 153

Fig. 8.4 The α-carotene (in wheat kernel 0.3 μg/g). The α-carotene is one of the primary isomers of the carotene. This compound belongs to the class of the organic compounds known as carotenes. These are a type of the unsaturated hydrocarbons containing 8 consecutive isoprene units. They are characterized by the presence of the 2 end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. The carotenes belonging form a subgroup of the carotenoids family (HMBD) . . . . . . . . . . . . . . . . . . . . . . . . . . 153

Fig. 8.5 The β-cryptoxanthin (content in wheat kernel 0.3 μg/g). The β-cryptoxanthin is a natural carotenoid pigment. In a pure form, the cryptoxanthin is a red crystalline solid with a metallic luster. In the human body, the cryptoxanthin converted to retinol and therefore considered a provitamin A.  As with the other carotenoids, the cryptoxanthin is an anti- oxidant and may help prevent the free radical damage to the cells. Structurally, the cryptoxanthin closely related to β-carotene, with only the addition of a hydroxyl group. It is a member of the xanthophylls. The β-cryptoxanthin is a major source of the retinol, often second only to β–carotene (HMBD). . . . . . . . . . 156

Fig. 8.6 The lutein (in wheat kernel 4 μg/g. Lutein is a common carotenoid xanthophyll. Carotenoids are among the most common pigments and are natural lipid-soluble anti-oxidants. Lutein is one of the 2 carotenoids (the other is zeaxanthin) that accumulate in the eye lens and the macular region of the retina with concentrations in the macula greater than those in plasma and other tissues. Lutein and zeaxanthin have identical chemical formulas and are isomers, but not stereoisomers. The main difference between them is in the location of a double bond in one of the end rings. This difference gives lutein 3 chiral centers whereas zeaxanthin has 2. A relationship between macular pigment optical density, a marker of lutein and zeaxanthin concentration in the macula, and lens optical density, an antecedent of cataractous changes, has suggested. The xanthophylls protecting the eye from ultraviolet phototoxicity via quenching reactive oxygen species. Generous intakes of lutein and zeaxanthin, have reduced the risk for cataract and age-related macular degeneration (HMDB) . . . . . . . . . . . . . . . . 157

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Fig. 8.7 The zeaxanthin (in wheat kernel 0.6) μg/g. The zeaxanthin is a carotenoid xanthophyll and is one of the most common carotenoids found in nature. The zeaxanthin pigment gives the corn, saffron, and many other plants their characteristic color. The zeaxanthin breaks down to form the picrocrocin and the safranal, which are responsible for the taste and aroma of the saffron. The zeaxanthin is one of the 2 carotenoids (the other is lutein) that accumulate in the eye lens and the macular region of the retina with the higher concentrations in the macula than those found in plasma and other tissues of the body (HMBD). . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 158

Fig. 8.8 The meso-zeaxanthin (present only in animals) . . . . . . . . . . . . . . . . 158Fig. 8.9 The choline. The choline is a basic constituent of lecithin

that found in many plants and animal organs. It is a precursor of acetylcholine, a methyl donor in various metabolic processes, and lipid metabolism. The choline considered an essential vitamin. While humans can synthesize small amounts (by converting phosphatidylethanolamine to phosphatidylcholine), it must consume in the diet to maintain health. The required levels are between 425 mg/d (female) and 550 mg/d (male). Milk, eggs, liver, and peanuts are especially rich in choline. Most choline found in phospholipids, namely phosphatidylcholine or lecithin. Choline can be oxidized to form betaine, which is a methyl source for many reactions (such as the conversion of homocysteine to methionine). Lack of sufficient amounts of choline in the diet can lead to a fatty liver condition and general liver damage. This arises from the lack of VLDL, which is necessary to transport fats away from the liver. Choline deficiency also leads to elevated serum levels of alanine aminotransferase and is associated with an increased incidence of liver cancer (HMBD). . . . . . . . . . . . . . . . . . . 161

Fig. 8.10 The betaine (Filipcev et al. 2018). The betaine, (N, N, N-trimethylglycine) was named after its discovery in sugar beet (Beta vulgaris) in the 19th century. It is a small N-tri-methylated amino acid, existing in zwitterionic form at neutral pH. It often called glycine betaine to distinguish it from other betaines that are widely distributed in the microorganisms, plants, and animals. Many naturally occurring betaines serve as organic osmolytes. These substances synthesized protect against osmotic stress, drought, high salinity, and high temperature. Intracellular accumulation of betaines permits water retention in cells, thus protecting from the effects of dehydration. Betaine functions as a methyl donor in that it carries and donates methyl functional groups to facilitate necessary chemical processes. In particular, it methylates homocysteine to

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methionine, also producing N, N-dimethylglycine. The donation of the methyl groups is important for proper liver function, cellular replication, and detoxification reactions. Betaine also plays a role in the manufacture of carnitine and serves to protect the kidneys from damage. Betaine derived from the diet or by the oxidation of choline. Betaine insufficiency is associated with metabolic syndrome, lipid disorders, and diabetes, and may have a role in vascular and other diseases. Betaine is important in development, from the pre-implantation embryo to infancy. Betaine is also widely regarded as an anti-oxidant. Betaine has shown to have an inhibitory effect on NO release in the activated microglial cells and may be an effective therapeutic component to control neurological disorders. As a drug, betaine hydrochloride was used as a source of hydrochloric acid in the treatment of hypochlorhydria. Betaine has also used in the treatment of liver disorders, for hyperkalemia, for homocystinuria, and gastrointestinal disturbances (HMBD). In the USA, the average dietary betaine intake is about 100–300 mg/day and rarely exceeds 400–500 mg. Human blood plasma typically contains 25–66 μM (Hefni et al. 2018; Bjørndal et al. 2018). . . . . . . . . . . . . . 164

Fig. 8.11 The dimethylglycine, shown in two graphical presentations. Dimethylglycine is an amino acid derivative found in the cells of all plants and animals. The human body produces dimethylglycine when metabolizing choline into glycine. The dimethylglycine that does not metabolize in the liver, transported by the circulatory system to other tissues. Dimethylglycine is also a byproduct of homocysteine metabolism. Homocysteine and betaine converted to methionine and N, N-dimethylglycine by betaine- homocysteine methyltransferase. Dimethylglycine in the urine is a biomarker for the consumption of legumes (HMBD) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 165

Fig. 8.12 Trigonelline. Trigonelline, an alkaloid, is a product of the metabolism of niacin that excreted in the urine. It found in coffee, where it may help to prevent dental caries by preventing the bacteria Streptococcus mutants from adhering to teeth. Trigonelline occurs in many other plants, including fenugreek seeds, garden peas, hemp seed, oats, and potatoes (HMBD) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 166

Fig. 9.1 The sterol, total sterols: 640 μg/g in the wheat kernel (Table 8.2). The sterols, also known as steroid alcohols, are a subgroup of the steroids and an important class of the organic molecules. They occur naturally in plants, animals, and fungi, with

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the most familiar type of animal sterol being cholesterol. The cholesterol is vital to animal cell membrane structure and function, and the precursor to fat-soluble vitamins and steroid hormones (HMDB) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 175

Fig. 9.2 β-sitosterol: 360 μg/g in the wheat kernel (Table 8.2), shown in two graphical presentations. β-sitosterol is a phytosteros (plant sterol) with similar to the cholesterol structure. Sitosterols are white, waxy powders with a characteristic odor. They are hydrophobic and soluble in alcohols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 176

Fig. 9.3 The campestanol, 53 μg/g in the wheat kernel (Table 8.2), shown in two graphical presentations. The campestanol is the plant stanol. It can decrease the circulating LDL-cholesterol level by the reducing of the intestinal cholesterol absorption (HMDB) . . . . . . . . . . . . . . . . 176

Fig. 9.4 The stigmastanol, 37 μg/g in wheat kernel (Table 8.2), shown in two graphical presentations. The stigmastanol is a plant stanol. It can decrease the circulating LDL- cholesterol level (HMDB) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 177

Fig. 9.5 The phenylalanine. The phenylalanine a is non-polar molecule because of the inert and hydrophobic nature of the benzyl side chain. Is an essential amino acid and the precursor of some compounds such as tyrosine, the monoamine neurotransmitters dopamine, norepinephrine, and epinephrine, and the skin pigment melanin. In plants, the phenylalanine is a precursor for the phenolic acid synthesis . . . . . . . . . . . . . . . . . . 179

Fig. 9.6 Phenylpropiolic acid, shown in two graphical esentations. Phenylpropiolic acid is one of several phenylpropanoid, natural products occurring in plants pathways involved in plant resistance providing building units of physical barriers against pathogen invasion, synthesizing an array of antibiotic compounds, and producing signals implicated in the mounting of plant resistance . . . . . . . . . . . . . . . . . . . . . . . . . . 183

Fig. 9.7 The ferulic acids, 100–1000 μg/g in the wheat kernel (Table 8.2). (a) trans-ferulic acid is a highly abundant phenolic phytochemical which presents in the plant cell walls. It absorbed by the small intestine and excreted in the urine. It is one of the most abundant phenolic acids in plants. It found as ester cross-links with the polysaccharides in the cell wall. Due to its phenolic nucleus and an extended side chain conjugation (carbohydrates and proteins), it readily forms a resonance stabilized phenoxy radical which accounts for its potent anti-oxidant potential (HMDB). (b) cis- ferulic acid consisting of cis-cinnamic acid bearing methoxy and hydroxy substituents at positions 3 and 4 respectively on the phenyl ring

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(HMDB). (c) cis-Ferulic acid [arabinosyl-(1->3)-[glucosyl- (1->6)]-glucosyl] ester. (d) Diferulic acids (also known as dehydrodiferulic acids) are formed by dimerization of the ferulic acid and found in the cell wall of the plant (Wikipedia) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 185

Fig. 9.8 The sinaptic acid, 32 μg/g in wheat kernel (Table 8.2), shown in two graphical presentations. Synaptic acid is a common constituent of plants and fruits. Sinapic acid has shown to exhibit anti-inflammatory function. Sinapic acid belongs to the family of hydroxycinnamic acid derivatives where the benzene ring hydroxylated (HMDB) . . . . . . . . . . . . . . . . . 187

Fig. 9.9 The coumaric acid, 19 μg/g in wheat kernel (Table 8.2), shown in two graphical presentations. cis-p-coumaric acid is found in coriander. Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers namely o-coumaric acid, m-coumaric acid, and p-coumaric acid that differ by the position of the hydroxy substitution of the phenyl group. p-coumaric acid is the most abundant isomer of the 3 in nature. cis-p-coumaric acid belongs to the family of hydroxycinnamic acid derivatives. These are compounds containing a cinnamic acid derivative where the benzene ring is hydroxylated (HMDB) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 187

Fig. 9.10 The vanillic acid (18 μg/g in wheat kernel (Table 8.2) shown in two graphical presentations. Vanillic acid is a phenolic acid found in some forms of vanilla and many other plant extracts. The vanillic acid is a flavoring compound and scent agent that produces a pleasant, creamy odor. It is the intermediate product in the two-step bioconversion of the ferulic acid to vanillin. The vanillic acid, which is chlorogenic acid, is an oxidized form of vanillin. It is also an intermediate in the production of the vanillin from the ferulic acid (HMDB) . . . . . . . . . . . . . . . . . . 188

Fig. 9.11 The syringic acid, 9–18 μg/g in wheat kernel (Table 8.2), shown in two graphical presentations. Syringic acid is a phenol present in some distilled alcoholic beverages. Syringic acid is a product of the gut metabolism of anthocyanins and other polyphenols that consumed fruits and alcoholic beverages. The syringic acid correlated with high anti-oxidant activity and inhibition of LDL oxidation (HMDB) . . . . . . . . . . . . . . . . . . . . 188

Fig. 9.12 The caffeic acid, 1.3 μg/g in wheat kernel (Table 8.2), shown in two graphical presentations. Caffeic acid is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food . . . . . . . . . . . . . . . . . . . . . . . . 189

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Fig. 9.13 The cinnamic acid, shown in two graphical resentations. Cinnamic acid It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs naturally in several plants. It exists as both a cis and a trans isomer, although the latter is more common (HMDB) . . . . . . . . . . . 189

Fig. 9.14 Tannins, total tannins content of 450 μg/g in the wheat kernel (Table 8.2). Tannins are astringent, bitter-tasting plant polyphenols that bind and precipitate proteins. The term tannin refers to the source of tannins used in tanning animal hides into leather; however, the term is widely applied to any large polyphenolic compound containing sufficient hydroxyls and other groups (such as carboxyls) to form strong complexes with the proteins and the other macromolecules. The tannins have molecular weights in the range of 500 – >3000. Tannins usually divided into hydrolyzable tannins and condensed tannins (proanthocyanidins). At the center of a hydrolyzable tannin molecule, there is a polyol carbohydrate (usually D-glucose). The hydroxyl groups of the carbohydrate partially or esterified with the phenolic groups such as gallic acid (in gallo-tannins) or ellagic acid (in ellagi-tannins). Hydrolyzable tannins hydrolyzed by the weak acids or the weak bases to produce carbohydrate and phenolic acids. The condensed tannins, also known as pro-anthocyanidins, are polymers of 2–50 (or more) flavonoid units that joined by the carbon-carbon bonds, which are not susceptible to being cleaved by hydrolysis. While hydrolyzable tannins and most condensed tannins are water-soluble, some very large condensed tannins are insoluble (HMDB) . . . . . . . . . . . . . . . . 190

Fig. 9.15 Flavonoids, total flavonoids content is 470 μg/g in the wheat kernel (Table 8.2). Flavonoids are a group of plant metabolites thought to provide health benefits through cell signaling pathways and anti-oxidant effects. These molecules found in a variety of fruits and vegetables. Flavonoids are polyphenolic molecules containing 15 carbon atoms and are soluble in water (Wikipedia) . . . . . . . . . . . 192

Fig. 9.16 Pelargonidin is a type of anthoxyans, The total anthocyanins content is 150 μg/g in the wheat kernel (Table 8.2). Pelargonidin is an anthocyanin (one of six), with an anti-oxidant and produces a characteristic orange color . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 192

Fig. 9.17 Chalcone, shown in two graphical presentations. Chalcone as is the flavone fraction of the dietary items. Chalcone is an aromatic ketone and an enone that forms the central core for a variety of important biological compounds, which known collectively as chalcones or chalconoids. Benzylideneacetophenone

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is the parent member of the chalcone series. Chalcones and their derivatives demonstrate wide range of the biological activities such as anti- oxidant, -diabetic, -neoplastic, -hypertensive, -retroviral, -inflammatory, -parasitic, -histaminic, -malarial, -fungal, -obesity, -platelet, -tubercular, immunosuppressant, -arrhythmic, -gout, anxiolytic, -spasmodic, -nociceptive, hypolipidemic, -filarial, -angiogenic, -protozoal, -bacterial, -steroidal, and cardioprotective . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 193

Fig. 9.18 The plant lignans (Adlercreutz 2007; Peterson et al. 2010), The matairesinol shown in two graphical presentations. (a) Actigenin. (b) Hydroxymatairesinol. (c) Secoisolariciresinol. (d) Syringaresinol. (e) Matairesinol . . . . . . . . . . . . . . . . . . . . . . . . . . 194

Fig. 9.19 The mammalian lignans (Peterson et al. 2010), shown in two graphical presentations. (a) Enterodiol is one of the most important lignan-type phytoestrogens identified in the serum, urine, bile, and seminal fluids of humans and animals. Phytoestrogens are a diverse group of compounds found in many edible plants that have, as their common denominator, a phenolic group that they share with estrogenic steroids. This phenolic group appears to play an important role in determining the estrogenic agonist/antagonistic properties of these compounds. Phytoestrogens have categorized according to their chemical structures as isoflavones and lignans. The enterodiol formed by bacteria in the intestinal tract from the plant lignans matairesinol and secoisolariciresinol, which exist in various whole- grain cereals. (b) Enterolactone . . . . . . . . . . . 196

Fig. 9.20 Samples of derivatives of the benzoxazinoids present in the wheat kernel, 2 on the upper panel and 10 on the middle panel. On the lower panel a typical metabolite present in the human urine. Content on the wheat kernel is 5 μg/g (Table 9.2) (Tanwir et al. 2013) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 199

Fig. 9.21 α-resorcylic, a primary metabolite of the alkylresorcinols, shown in two graphical presentations. 3,5-dihydroxybenzoic acid, also known as α-resorcylic acid or α-resorcylate, belongs to the hydroxybenzoic acid derivatives class of compounds. Those are compounds ontaining a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and hydroxyl groups. 3,5-dihydroxybenzoic acid is soluble (in water) and a weakly acidic compound. It is a metabolite of alkylresorcinols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 200

Fig. 9.22 The alkylresorcinol with the side chain containing 17 (C:17), 19, 21, 23 and 25 carbon units; the content in the wheat kernel is 420 μg/g (Table 8.2). (Landberg et al. 2014). The alkylresorcinols are relatively rare in nature, with the main known sources being wheat, rye, barley, triticale (cereal grasses) (HMDB) . . . . . . . . . . . . 201

Fig. 9.23 DHPPA. C9H10O4 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 202

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Fig. 11.1 The policosanol, shown in two graphical presentations. 1-octacosanol (also known as n-octacosanol; octacosyl alcohol; cluytyl alcohol; or montanyl alcohol) is a straight-chain aliphatic 28-C primary fatty alcohol. This compound is common in the epicuticular waxes of the plants, including the leaves of many species of Eucalyptus, of most of the forage and cereal grasses, of acacia, trifolium, pisum, and many other legume genera among many others, sometimes as the major wax constituent. The octacosanol also occurs in the wheat germ and it is insoluble in water but freely soluble in low-molecular-weight alkanes and chloroform. These are aliphatic alcohols consisting of a chain of 8 to 22 C atoms (HMDB) . . . . . . . . . . . . . . . . . . . . . . . . . . . 229

Fig. 12.1 The phytic acid and the inositol. (a) Myo-inositol hexakisphosphate is an intermediate in the inositol phosphate metabolism. It can be generated from D-myo-inositol 1,3,4,5,6- pentakisphosphate via the enzyme inositol-pentakisphosphate 2-kinase. The myo- inositol hexakisphosphate known as phytic acid. It can use clinically as a complexing agent for removal of the traces of the heavy metal ions. It acts also as a hypocalcemic agent. The phytic acid is a strong chelator of important minerals such as calcium, magnesium, iron, and zinc and can contribute to the mineral deficiencies in the developing countries. For people with a particularly low intake of essential minerals, especially young children and those in developing countries, this effect can be undesirable. The dietary mineral chelators help prevent over-mineralization of the joints, the blood vessels, and other parts of the body, which is most common in the older persons. The phytic acid may consider a phytonutrient, providing an anti-oxidant effect (Wikipedia). (b) The inositol phosphate is an intermediate step in the metabolism of the glucose-6- phosphate to myo-inositol. The myoinositol synthesized from the glucose-6-phosphate (G-6-P) in 2 steps. First, the G-6-P isomerized to myoinositol 1-phosphate, which then dephosphorylated to give myoinositol . . . . . . . . . . . . . . . . . . . . 233

Fig. 12.2 The oxalic acid is a dicarboxylic acid with the formula C2H2O4. It occurs naturally in many foods, but excessive ingestion of the oxalic acid or prolonged skin contact can be dangerous. Blood concentration is ~1.2 μg/mL . . . . . . . . . . . . . . . . . . . . . . . . . . 237

Fig. 14.1 Schematic representation of the gastrointestinal tract (GIT). The GIT segments: 1. oral cavity; 2. esophagus; stomach segments: (3. fundus; 4. stomach body; 5. pyloric part; and 6. pyloric sphincter); 7. duodenum; 8. jejunum; 9. ileum; 10. terminal ileum; 11. ileocecal sphincter; 12. cecum; 13. ascending colon; 14. right transverse colon; 15. left transverse

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colon; 16. descending colon; 17. sigmoid colon; 18. rectum; 19. anus; and 20. anal sphincter Located outside the gastrointestinal tract: liver, common bile duct, gall bladder, and pancreas (lays near the pyloric sphincter, not shown), cecal appendix, diverticula, and polyps (the last 2 projections located outside and inside the GIT, respectively), but mainly on the sigmoid colon . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 274

Fig. 14.2 On the left - the black holes show the openings of the diverticula; on the right - a sigmoid polyp (from the surgery of ER) . . . . . . . . . . 276

Fig. 14.3 The prevalence of diverticulosis in a sample of Rome subjects (n = 1090), by age (Cecco et al. 2016) . . . . . . . . . . . . . . . . . . . . . . . . 277

Fig. 14.4 The 4 main forms of the bile acids (a) Cholic acid (cholate): Cholic acid is a major primary bile acid produced in the liver and is usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is a minute and depends only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine, and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and consequently require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties and there are a plethora of mechanisms to limit their accumulation in blood and tissues. Among the primary bile acids, cholic acid is considered to be the least hepatotoxic while deoxycholic acid is the most hepatoxic (HMDB). (b) Deoxycholic acid: Deoxycholic acid is a secondary bile acid produced in the liver and is usually conjugated with glycine or taurine. (c) Chenodeoxycholic acid. (d) Lithocholic acid, also known as 3α-hydroxy-5β-cholan-24-oic acid or LCA, is a secondary bile acid. It is formed from chenodeoxycholate by bacterial action . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 287

Fig. 14.5 The main 2 amino acids with a high tendency to form bile salts: glycine and taurine . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 289

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Fig. 15.1 The incidence of colorectal cancer by age. Upper panel – the incidence of hospitalization because of colorectal cancer in the US (Sonnenberg and Byrd-Clark 2014). Lower panel – incidence in Israel (Barchana et al. 2004) . . . . . . . . . 316

Fig. 17.1 Distribution of alkylresorcinol chain-length in cereal kernels (Landberg et al. 2009; Ross et al. 2003; Geerkens et al. 2015; Andersson et al. 2010a; Andersson et al. 2010b; Chen et al. 2004; Kulawinek et al. 2008; Landberg et al. 2006) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 356

Fig. 22.1 Acrylamide, shown in two graphical presentations . . . . . . . . . . . . . . 399

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Table 1.1 The main ingredients of the kernel organs (Hemery et al. 2009). . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3

Table 1.2 The global grain production 2016 (FAOSTAT) . . . . . . . . . . . . . . . 14

Table 3.1 The global cereal production and other starchy foods, M ton/y (FAOSTAT). . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 28

Table 3.2 The global production of the main carbohydrate staple-foods 2012, adjusted for the energy equivalent of the wheat (FAOSTAT) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 32

Table 3.3 Relative prices received by the farmers in the US. 2016/7. (USDA, Wheat Outlook) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 38

Table 3.4 The cereal major ingredients . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 40

Table 4.1 The effect of the extraction rate (refining) on the flour composition (Slavin et al. 1999, 2001). . . . . . . . . . . . . . . . . . . . . . . . 51

Table 4.2 The milling yield (Gebruers et al. 2008) . . . . . . . . . . . . . . . . . . . . . . 52Table 4.3 The effect of the wheat-flour refining on the dough

content of the phenolic acids, carotenoids, and the tocopherols (Lu et al. 2015). . . . . . . . . . . . . . . . . . . . . . . . . . 55

Table 4.4 Bound ferulic acid content (ferulic acid content μg/g of dry sample) and total phenolic content (μg/g) in flour and bread products (average of 5 flour brands and bread products) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 56

Table 4.5 The anti-oxidant capacity in flour and bread (average of 5 flour brands and bread products) by 3 measures. . . . . . . . . . . . . 57

Table 4.6 The destruction of the vulnerable ingredients by the milling and the increase in the starch damage. . . . . . . . . . . . . 60

Table 5.1 The main groups of the kernel micro-ingredients . . . . . . . . . . . . . . . 73Table 5.2 The wheat kernel volume characterizations,

and the concentrations of protein, and amino acids . . . . . . . . . . . . . . 76

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Table 5.3 Animal protein intake and the ratio between plant protein and animal proteins by the world regions and the economic levels (Vliet et al. 2015) . . . . . . . . . . . . . . . . . . . . 83

Table 5.4 Wheat kernel lipids. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 84Table 5.5 The wheat kernel minerals . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 87

Table 6.1 The wheat kernel carbohydrates. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 92Table 6.2 A comparison between the kernel composition of the

carbohydrate and fiber fractions of the main cereals . . . . . . . . . . . . . 93

Table 7.1 The fermentability rate of the dietary fiber ingredients in the human colon (Brownlee et al. 2006) . . . . . . . . . . . . . . . . . . . 109

Table 8.1 The wheat kernel vitamins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 140Table 8.2 The wheat kernel lipophilic anti-oxidants

and related ingredient . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 143Table 8.3 The tocols in the wheat germ oil, μg/g, and percentage,

(Malekbala et al. 2017). . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 148Table 8.4 The α- and the γ-tocopherol in edible oils, μg/g

(Grilo et al. 2014) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 151Table 8.5 The carotene concentrations in the plasma of the European

populations (Eggersdorfer and Wyss 2018) . . . . . . . . . . . . . . . . . . . 154Table 8.6 The content of the methyl donors in the wheat kernel

and some other cereals . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 160

Table 9.1 Plasma alkyresorcinol values collected from the available data . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 203

Table 9.2 The phenolic compounds in the main cereals, μg/g . . . . . . . . . . . . . 204Table 9.3 Phenolic acid variations in the wheat kernel . . . . . . . . . . . . . . . . . . 210

Table 10.1 The daily polyphenol intake in the Israeli menu (Statistical Abstract of Israel 2016) . . . . . . . . . . . . . . . . . . . . . . . . . 219

Table 12.1 Phytic acid in food items, μg/g. . . . . . . . . . . . . . . . . . . . . . . . . . . . . 232

Table 13.1 The total wheat intake versus the whole-wheat intake in various countries (FAOSTAT: Food and agriculture data) . . . . . . 242

Table 14.1 The gut segments characterizations . . . . . . . . . . . . . . . . . . . . . . . . . 269Table 14.2 The dynamics of the GIT flows . . . . . . . . . . . . . . . . . . . . . . . . . . . . 275

Table 15.1 The effect of the whole-wheat intake on the decrease in the relative risk (RR) of morbidity and mortality as evaluated in 20 categories . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 303

Table 15.2 Summary of the 20 categories (presented in Table 15.1) . . . . . . . . . 313Table 15.3 The incidence of the colorectal malignancy

and the prevalence at the colorectal site (Europe, USA, Iceland, Poland, and Israel) . . . . . . . . . . . . . . . . . . . 318

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Table 18.1 The effect of the yellow pigments on AMD: The decrease in the relative risk (RR) of the incidence of advanced AMD with the plasma concentration or the higher intake of dietary carotenoids in comparison to the lower level. . . . . . . . . . 367

Table 18.2 The decrease in the relative risk (RR) of the cataract incidence with the increase in the dietary intake or the blood concentration of lutein, zeaxanthin and vitamin E . . . . . . . . . . . . . . 369

Table 21.1 The effect of the high intake of the RTEC on the relative risk (RR) of the morbidity and the mortality, and the RR for overweight incidence . . . . . . . . . . . . . . . . . . . . . . . . 391

Table 24.1 The daily whole-grain intake in the 28 European countries with a decreasing order for each range. . . . . . . . . . . . . . . . . . . . . . . 410

Table 25.1 Mesh sieve conversion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 417Table 25.2 Recipes for the whole-wheat bread . . . . . . . . . . . . . . . . . . . . . . . . . 417

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