Food Oxidants and Antioxidants Chemical, Biological, and Functional Properties Chemical and Functional Properties of Food Components Series SERIES EDITOR Zdzisław E Sikorski Food Oxidants and Antioxidants: Chemical, Biological, and Functional Properties Edited by Grzegorz Bartosz Fermentation: Effects on Food Properties Edited by Bhavbhuti M Mehta, Afaf Kamal-Eldin and Robert Z Iwanski Methods of Analysis of Food Components and Additives, Second Edition Edited by Semih Otles Food Flavors: Chemical, Sensory and Technological Properties Edited By Henryk Jelen Environmental Effects on Seafood Availability, Safety, and Quality Edited by E Grazyna Daczkowska-Kozon and Bonnie Sun Pan Chemical and Biological Properties of Food Allergens Edited By Lucjan Jedrychowski and Harry J Wichers Chemical, Biological, and Functional Aspects of Food Lipids, Second Edition Edited by Zdzisław E Sikorski and Anna Kołakowska Food Colorants: Chemical and Functional Properties Edited by Carmen Socaciu Mineral Components in Foods Edited by Piotr Szefer and Jerome O Nriagu Chemical and Functional Properties of Food Components, Third Edition Edited by Zdzisław E Sikorski Carcinogenic and Anticarcinogenic Food Components Edited by Wanda Baer-Dubowska, Agnieszka Bartoszek and Danuta Malejka-Giganti Toxins in Food Edited by Waldemar M Dąbrowski and Zdzisław E Sikorski Chemical and Functional Properties of Food Saccharides Edited by Piotr Tomasik Chemical and Functional Properties of Food Proteins Edited by Zdzisław E Sikorski Food Oxidants and Antioxidants Chemical, Biological, and Functional Properties EDITED BY Grzegorz Bartosz Boca Raton London New York CRC Press is an imprint of the Taylor & Francis Group, an informa business CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2014 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group, an Informa business No claim to original U.S Government works Version Date: 20130214 International Standard Book Number-13: 978-1-4398-8242-9 (eBook - PDF) This book contains information obtained from authentic and highly regarded sources Reasonable efforts have been made to publish reliable data and information, but the author and publisher cannot assume responsibility for the validity of all materials or the consequences of their use The authors and publishers have attempted to trace the copyright holders of all material reproduced in this publication and apologize to copyright holders if permission to publish in this form has not been obtained If any copyright material has not been acknowledged please write and let us know so we may rectify in any future reprint Except as permitted under U.S Copyright Law, no part of this book may be reprinted, reproduced, transmitted, or utilized in any form by any electronic, mechanical, or other means, now known or hereafter invented, including photocopying, microfilming, and recording, or in any information storage or retrieval system, without written permission from the publishers For permission to photocopy or use material electronically from this work, please access www.copyright.com (http://www.copyright.com/) or contact the Copyright Clearance Center, Inc (CCC), 222 Rosewood Drive, Danvers, MA 01923, 978-750-8400 CCC is a not-for-profit organization that provides licenses and registration for a variety of users For organizations that have been granted a photocopy license by the CCC, a separate system of payment has been arranged Trademark Notice: Product or corporate names may be trademarks or registered trademarks, and are used only for identification and explanation without intent to infringe Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com and the CRC Press Web site at http://www.crcpress.com Contents Preface vii Editor .ix Contributors .xi Abbreviations xv Chapter Oxidation of Food Components: An Introduction Anna Kołakowska and Grzegorz Bartosz Chapter Oxidants Occurring in Food Systems 21 Manuel Pazos and Isabel Medina Chapter Measuring the Oxidation Potential in Foods 47 Louise Bennett, Amy Logan, Netsanet Shiferaw- Terefe, Tanoj Singh, and Robyn Warner Chapter Mechanisms of Oxidation in Food Lipids 79 Gloria Márquez-Ruiz, Francisca Holgado, and Joaquín Velasco Chapter Protein Oxidation in Foods and Its Prevention 115 Caroline P Baron Chapter Use of Added Oxidants in Food Processing 137 Emanuela Zanardi Chapter Effects of Oxidation on Sensory Characteristics of Food Components during Processing and Storage 159 Susan Brewer Chapter Effects of Oxidation on the Nutritive and Health-Promoting Value of Food Components 197 Rosario Zamora, Rosa M Delgado, and Francisco J Hidalgo v vi Contents Chapter Natural Antioxidants in Food Systems 235 Petras Rimantas Venskutonis Chapter 10 Antioxidants Generated in Foods as a Result of Processing 303 María Dolores del Castillo, Elena Ibáđez, and Miguel Herrero Chapter 11 Mechanisms of Antioxidant Activity 325 Klaudia Jomova, Michael Lawson, and Marian Valko Chapter 12 Measuring the Antioxidant Activity of Food Components 343 Takayuki Shibamoto Chapter 13 Measuring the Antioxidant Activity of Apple Products 359 Iwona Wawer Chapter 14 Antioxidant and Prooxidant Activity of Food Components 375 Anna Gliszczyńska-Świgło and Jan Oszmiański Chapter 15 Bioavailability and Antioxidant Activity of Curcuminoids and Carotenoids in Humans 433 Alexa Kocher, Christina Schiborr, Daniela Weber, Tilman Grune, and Jan Frank Chapter 16 Case Studies on Selected Natural Food Antioxidants .465 Miguel Herrero, José A Mendiola, Alejandro Cifuentes, and Elena Ibáñez Chapter 17 Functional Antioxidant Foods 489 Manuel Viuda-Martos, Jose A. Pérez- Álvarez, and Juana Fernández-López Chapter 18 Concluding Remarks 529 Grzegorz Bartosz and Izabela Sadowska-Bartosz Index 537 Preface Food antioxidants are of primary importance for the preservation of food quality during processing and storage They are also of considerable interest for consumers, who seek antioxidant-rich food items hoping for the prevention of diseases and postponement of aging However, the status of food depends on the balance of prooxidants and antioxidants, the former being usually neglected when discussing food antioxidants This book comprises, in one volume, a selection of topics covering both prooxidants and antioxidants occurring in food, which can be interesting, first of all, for food technologists and chemists and students in these fields After a general introduction to the problem (Chapter 1), Chapter characterizes the main oxidants present in food, including both nonenzymatic oxidants (hemoproteins, redox active metals, and photosensitizers) and enzymes (lipoxygenases, myeloperoxidases, lactoperoxidases, and polyphenol oxidases) While the idea of antioxidant activity/capacity/potential has become popular, that of oxidation potential, equally useful, is much less known; it is presented in Chapter Chapters and discuss the mechanisms of oxidation of main food components, lipids and proteins, respectively, including factors affecting this process, such as the presence of prooxidants and antioxidants, light, temperature, oxygen, and food composition In many cases, exogenous oxidants are added to food during processing; this practice, as well as the effects of such physical agents as irradiation, freeze–thawing, and high hydrostatic pressure during food processing, is presented in Chapter Chapter discusses the effects of oxidation on the sensory characteristics of food components; these effects are usually unwanted, but there are also cases where they can be beneficial Chapter analyzes how the oxidation of main food components (lipids, proteins, and carbohydrates) and antioxidants affects the nutritive and healthpromoting features of food components Chapter discusses natural antioxidants present in food, especially those that are less known, such as antioxidant amino acids, peptides, proteins, and polysaccharides and oligosaccharides Chapter 10 presents antioxidants generated in food as a result of processing The mechanisms of antioxidant activity and the main antioxidant enzymes are discussed in Chapter 11 The next two chapters deal with the measurement of the antioxidant activity of food components (Chapter 12) and their application to a specific material (apple products, Chapter 13) Many food components are classified as antioxidants but under certain conditions may have prooxidant activity; this question is described in Chapter 14 The bioavailability and antioxidant activity of two important groups of antioxidants, curcuminoids and carotenoids, are discussed in Chapter 15 Chapter 16 deals with case studies on selected natural food antioxidants, presenting novel extraction methods for optimal preservation of antioxidant activities, such as supercritical fluid extraction, pressurized liquid extraction, subcritical water extraction, and microwave- and ultrasound-assisted extraction, as well as their application to specific raw materials Functional antioxidant foods and beverages are presented in Chapter 17 vii viii Preface The last chapter contains some general ideas concerning mainly the effects of food on the redox homeostasis of the organism The authors of the book are renowned scientists from Australia, Denmark, Germany, Italy, Lithuania, Poland, Slovakia, Spain, and the United States I am deeply indebted for their contributions and cooperation I hope that the book can provide basic information for students and newcomers to the field but also be of use to more experienced readers interested in the problems of food prooxidants and antioxidants Editor Grzegorz Bartosz received his MS and PhD degrees from the University of Łódź and his DSc degree from the Jagiellonian University of Cracow (Poland) He spent his postdoctoral fellowship at Texas A&M University; was a research fellow at the University of Düsseldorf and Macquarie University in Sydney; and for short terms, visited various European universities and institutions Presently, he is a professor at the Department of Molecular Biophysics of the Faculty of Biology and Protection of the Environment at the University of Łódź and at the Department of Biochemistry and Cell Biology of the Faculty of Biology and Agriculture of the University of Rzeszów (Poland) His research interest concentrates on reactive oxygen species and antioxidants He is a corresponding member of the Polish Academy of Sciences and of the Polish Academy of Arts and Sciences and chairman of the Committee of Biochemistry and Biophysics of the Polish Academy of Sciences He is on the editorial boards of Acta Biochimica Polonica, Acta Physiologiae Plantarum, Free Radical Biology and Medicine, and Free Radical Research In 2011–2012 he was president of the Society for Free Radical Research–Europe He is an author of more than 300 journal publications, books, and book chapters ix Index Page numbers followed by f and t indicate figures and tables, respectively A α-Aminoadipic semialdehyde (AAS), 117 formation of, 49, 53f AAS See A-Aminoadipic semialdehyde (AAS) ABTS assay See 2,2ʹ-azino-bis (3-ethylbenzothiazoline-6 sulfonic acid) (ABTS) assay ACA assay See Aldehyde/carboxylic acid (ACA) assay Aỗai berries (Euterpe oleracea Mart.) antioxidant capacity, 497 Accelerated solvent extraction (ASE), 467 Acyl lipid oxidation, 203–205 effect on nutritive and health-promoting value, 205–206 Advanced glycation end products (AGEs), 121, 122 Advanced lipoxidation end products (ALEs), 63, 121, 123 AGEs See Advanced glycation end products (AGEs) Agri-food waste and by-products, natural antioxidants from cereals, seeds, and nuts, 271–273 fruits and vegetables, 269, 271 general aspects, 266–269, 268t, 270f oil production by-products, 273–274 ALA See α-Lipoic acid (ALA) Alcoholic drinks, antioxidant activity of beer, 513–514 wine, 514–515 Alcohols, 58–59 Aldehyde/carboxylic acid (ACA) assay, 344, 348–349, 348f, 349f Aldehydes, 13–14 absorbable, 13–14 short-unsaturated, 5–6 Aldonic acids, 58 ALEs See Advanced lipoxidation end products (ALEs) S-Allylcysteine, 222 α-Lipoic acid (ALA), 335 Allium cepa L (onion), 503–504 Allium sativum (garlic), 502–503 Amino acids See also Protein oxidation natural antioxidants from animal origin sources, 252–254 factors affecting antioxidant activity of, 256 general aspects, 245–251, 247f, 248t–251t marine sources, 251–252 plant origin sources, 254–256 oxidation effect on nutritive and health-promoting value, 206–208 products detected in food, 117t 8-Aminonaphthalene-1,3,6-trisulfonic acid (ANTS), 68 Animal origin sources, of natural antioxidants, 252–254 Annona cherimola (cherimoya), 501 Anthocyanidins, 387, 492, 494f Anthocyanins, 39, 60, 387, 492, 494f Antioxidant activity(ies) See also Prooxidant activity of apple products, measurement of, 359–372 CUPRAC assay, 369–370 DPPH• radical scavenging (ESR assay), 365–369 DPPH• radical scavenging (spectrophotometric assay), 362–365 prameters characterization, 370–372 of betalains, 396–399, 398f of beverages coffee, tea, and beer, 350–351, 351f of Maillard reaction products, 351–354, 352f, 353f of carotenoids free radical scavenging, 455 physical quenching of singlet oxygen, 454 of curcuminoids, 444–445 mechanisms of, 325–338 enzymatic antioxidants, 328–330 nonenzymatic antioxidants, 330–338 sources of free radicals, 326–328 methods for measurement aldehyde/carboxylic acid assay, 348–349, 348f, 349f chromatographic methods, 336–347, 347t spectrophotometric methods, 334–346, 335t of plant phenolics, 325–338, 376 cinnamic acids, 380–382, 381t 537 538 flavonoids, 382–389, 383t–384t, 386f, 396 herbs and spices, 390–391 hydroxybenzoic acids, 380–382, 381t lignans, 390 tannins, 389–390 Antioxidants (AOXs), 48 See also Natural antioxidants analysis of products, 68–69 of apples, 360–362 concept of, 236 defined, 235–236 effects on lipid oxidation, 97 enzymes catalase, 329–330 glutathione peroxidases, 330 superoxide dismutase, 328–329 extraction methods for compressed fluids extraction, instrumentation for, 468–469, 468f microwave and ultrasound-assisted extraction, 469–470 pressurized liquid extraction, 467 subcritical water extraction, 467–468 supercritical fluid extraction, 466–467 nonenzymatic ascorbic acid, 330–332, 331f carotenoids, 335–336 flavonoids, 337–338, 337f glutathione, 333–335, 334f lipoic acid, 335 vitamin E, 332–333 oxygen scavenging by, 48 pathways and products of, 59–60 ascorbic acid, 61–62, 62f carotenoids, 62–63 phenolic compounds, 60 tocopherols, 60–61, 61f for protein oxidation feeding strategies, 125–126, 126t processing and storage strategies, 127–128, 127t Antioxidative–oxidative status, 16 AOXs See Antioxidants (AOXs) Apple products, antioxidant activity measurement, 359–372 CUPRAC assay, 369–370 DPPH• radical scavenging ESR assay, 365–369 spectrophotometric assay, 362–365 prameters characterization, 370–372 Apples, antioxidants of, 360–362 ARA See Arachidonic acid (ARA) Arachidonic acid (ARA), Argan fruit (Argania spinosa), 505 Argania spinosa (argan fruit), 505 Argan oil, 505–506 Aromatic herbs, antioxidant activity of, 509–510 Index Ascorbate, 33 Ascorbic acid (vitamin C), 12, 25, 61–62, 62f antioxidant/prooxidant role of, 34, 61–62, 62f, 330–332, 331f, 399–400, 400f vs folates, 407t oxidation, effect on nutritive and healthpromoting value, 216 ASE (accelerated solvent extraction), 467 Autoxidation, 3–4 of conjugated fatty acids, 89, 91–92, 91f, 92f factors antioxidants, 97 fatty acid composition, 97 light, 96 oxygen concentration, 96 prooxidants, 97 temperature, 96 at high temperatures, 93–96, 94f mechanisms and products formed, 80–81 oxidized monomers, 86, 87f, 88f polymerization compounds, 89, 90f primary products (hydroperoxides), 81–83, 82f, 83t secondary products, 83–89 volatile compounds, 83–86, 84f, 85f, 86t secondary products of, 13–14 steps, 80 of unsaturated fatty acids, 54–55, 56f 2,2ʹ-azino-bis (3-ethylbenzothiazoline-6 sulfonic acid) (ABTS) assay, 344, 345 B β-Carotene, 402, 450, 455 antioxidant and prooxidant activity of, 402–405 bleaching, 344, 345 chemical structure, 403f β-Cryptoxanthin, 402 chemical structure, 403f Beer, antioxidant activity of, 350–351, 513–514 Berry fruits antioxidant capacity, 497–498 natural antioxidants in, 278–280 Betalains, antioxidant activity of, 396–399, 398f chemical structures and atom numbering system, 397f Beverages, antioxidant activity of beer, 350–351, 351f, 513–514 coffee, 350–351, 351f, 511–512 of Maillard reaction products, 351–354, 352f, 353f tea, 350–351, 351f, 511 Bioavailability of carotenoids, 448–451, 449f of curcuminoids, 439–444, 440t–441t Index described, 435 of polyphenols, 377–380 Biocytin, 220 chemical structures, 221f Biotin chemical structures, 221f oxidation, effect on nutritive and healthpromoting value, 220, 221f Biotransformation, of curcuminoids, 436–439, 437f, 438f Blackberries (Rubus fruticosus), 497 Black raspberries (Rubus occidentalis), 497–498 Blueberries (Vaccinium corymbosum), 497 Blue biotechnology, 476 Bohr effect, 31 Brady’s reagent See 2,4-Dinitrophenylhydrazine (DNPH) C Caffeic acid, 25, 39 Carbohydrate oxidation, 11–12, 202–203, 202f analysis of products, 67–68 effect of, 15t–16t effect on nutritive and health-promoting value, 203 pathways and products of, 57 in milk, 58 in plants, 58 sugars and alcohols, 58–59, 59f Carboxymethyllysine (CMLys), 122 Carnosic acid, 128, 470, 471 chemical structure, 391, 471f Carnosine, 22 Carnosol, chemical structure, 391f, 471f Carotenoids, 13, 62–63, 335–336, 434, 445–448 antioxidant activities of, 402–405 free radical scavenging, 455 physical quenching of singlet oxygen, 454 vs α-tocopherol, 404t bioavailability of (absorption, tissue distribution, and excretion), 448–451, 449f characteristics, 445–448, 447t chemical structures, 403f, 446f concentrations in humans, 451, 452t–454t E numbers, trivial names, colors, dietary sources, and use of, 447t microalgal antioxidants and (case studies), 476–477 Dunaliella salina, 477–479, 478f Haematococcus pluvialis, 479–481, 481f oxidation of, 210–211 effects on nutritive and health-promoting value, 211 prooxidant activity of, 402–405 for protein oxidation prevention, 129–130 539 provitamin A activity of, 455–456 release from food matrix, 448 Carvacrol, 391f Catalase, 329–330 Catechins (flavan-3-ols), 34, 39, 378, 385–387 structures, 386f Cereals antioxidants in, 286–287, 506–507 from waste and by-products of, 271–273 Chemical oxidants See Nonenzymatic oxidants Cherimoya (Annona cherimola), 501 Chlorogenic acid, 39 Chlorophyll, 32, 33–34 Cholesterol oxidation products (COPs), 150 6-chromanol, 400 structure, 401f Chromatographic methods for antioxidant activity measurement, 336–347, 347t Cinnamic acids antioxidant activity of, 380–382, 381t Citrus fruits, antioxidant capacity, 499–500 CLA See Conjugated linoleic acid (CLA) CMLys See Carboxymethyllysine (CMLys) Cocoa, antioxidant activity of, 513 Coconut oil, 506 Coffee, antioxidant activity of, 350–351, 351f, 511–512 Color, 161 of meat products, oxidation effects on, 173–174 Compressed fluids extraction, 468–469 instrumentation for, 468–469, 468f Conjugated diene assay, 344 Conjugated fatty acids, autoxidation of, 89, 91–92, 91f, 92f Conjugated linoleic acid (CLA), 140, 277 autoxidation of, 89 Copper, in lipid oxidation, 139 Copra oil (CO), 506 COPs See Cholesterol oxidation products (COPs) p-coumaric acid, 39 Cross-linking reactions pathways and products of, 63–64 Culinary cooking practices prooxidant effect of, 149–150 CUPRAC assay study of antioxidant activity in apple juices, 369–370 Curcumin, 435–436, 436f in animals and humans, bioavailabilityenhancing strategies, 443–444 Curcuminoids, 434 antioxidant activities of, 444–445 bioavailability of (absorption, tissue distribution, and excretion), 439–444, 440t–441t 540 biotransformation of, 436–439, 437f, 438f characteristics, 435–436 chemical structures, 436f and metabolites of, gastrointestinal stability of, 439 Cyanidin, 387 Cyanidin 3-O-glucoside, 387 D Dairy products protein oxidation impact on, 124 riboflavin and, 33–34 sensory characteristics, oxidation effects on, 178–179 Date (Phoenix dactylifera L.), antioxidant capacity, 498–499 DHA See Docosahexaenoic acid (DHA) DHLA See Dihydrolipoic acid (DHLA) 7,8-Dihydrofolic acid (DHF), 405–406, 405f Dihydrolipoic acid (DHLA) chemical structure, 409f 3,4-dihydroxyphenylalanine (DOPA), 39 Dimocarpus longan Lour (longan), 501 2,4-Dinitrophenylhydrazine (DNPH), 66 Diospyros kaki L (persimmons), 499 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay, 344–345 Direct oxidation, of protein, 116 Disaccharides, 57 Diterpernes, 128 5,5-dithiobis(2-nitrobenzoate) (DTNB), 66 Di-tyrosine cross-linked proteins, 66 Docosahexaenoic acid (DHA), DOPA See 3,4-dihydroxyphenylalanine (DOPA) DPPH assay See 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay DPPH• radical-scavenging assay, 359 antioxidant activity in apples and ESR assay, 365–369 spectrophotometric assay, 362–365 Dunaliella salina (case studies), 477–479, 478f E EDTA See Ethylenediaminetetraacetic acid (EDTA) Eicosapentaenoic acid (EPA), Electron spin resonance (ESR) assay, 362 studies of apple juice, 365–367, 365f, 366f studies of apple purée, 367–368, 369f Ellman’s reagent See 5, 5-dithiobis (2-nitrobenzoate) (DTNB) Enhanced solvent extraction (ESE), 467 Enzymatic antioxidants catalase, 329–330 Index glutathione peroxidases, 330 superoxide dismutase, 328–329 Enzymatic oxidants, 22t, 34–35 lactoperoxidase, 38–39 lipoxygenases, 35–38 myeloperoxidase, 38–39 polyphenol oxidases, 39–40 Enzymatic oxidation of lipid, 97–98 Enzymatic peroxidation, 4–5 Enzymatic treatments, in food processing, 312–313 EPA See Eicosapentaenoic acid (EPA) ESE (enhanced solvent extraction), 467 Espirosmanol chemical structure, 471f ESR assay See Electron spin resonance (ESR) assay Ethylenediaminetetraacetic acid (EDTA), 25 Euterpe oleracea Mart (aỗai berries), 497 Exotic fruits, antioxidant capacity, 500–501 Extraction methods, for antioxidants compressed fluids extraction, instrumentation for, 468–469, 468f microwave and ultrasound-assisted extraction, 469–470 pressurized liquid extraction, 467 subcritical water extraction, 467–468 supercritical fluid extraction, 466–467 F Fatty acid (FA), composition effects on lipid oxidation, 9, 97 protein oxidation, composition of foods, 171t–172t Fe(III)/Fe(II) transition, redox potential of, 24–25, 25t Fenol-type flavonoids, prooxidant chemistry of, 392–393, 392f Fenton reaction, 529 (Fe)-mediated H-atom abstraction, 49 Fenton-type mechanism, 27, 34 Fermentation, 313–314, 314f Ferric-reducing ability of plasma (FRAP) assay, 359 Ferric reducing/antioxidant power (FRAP) assay, 344 Ferric thiocyanate (FTC) assay, 344, 346 Ferrous iron, 26–27 Ferrous oxidation-xylenol orange (FOX) assay, 344, 346 FerrylHb formation of, 30 Fibers, with antioxidant activity, 495–496 Fish products, 6, 13, 21, 120, 124 influence of lipid oxidation, 104–105 Index FI system See Flow ice (FI) system Flavanols, 385, 492, 493f Flavanones, 385, 492, 493f Flavones, 385, 492, 493f Flavonoids, 128, 213–214, 337–338, 337f antioxidant activity of, 382–389, 383t–384t, 386f, 396 contribution to health-promoting activity, 396 chemical structures, 214f, 383t–384t, 493f, 494f dietary sources, 383t–384t metal chelation by, 389 as natural antioxidants, 389, 492 prooxidant activity of, 391–396, 392f, 393f contribution to health-promoting activity, 396 Flavonol glycosides, 39 Flavonols, 385, 492 Flavor(s), 161 oxidation effects on meat products, 170–173, 171t–172t oils, 174–176 produced in foods by lipid oxidation, 166t–167t Flow ice (FI) system, 141 Folates antioxidant and prooxidant activity of, 405–408 vs ascorbic acid and α-tocopherol, 407t atom numbering system, 405f chemical structures, 220f, 405f mechanisms, 408f oxidation, effect on nutritive and healthpromoting value, 219, 220f pH effect on TEAC values of, 407f Food emulsions influence of lipid oxidation, 102–103 Food enzymes protein oxidation impact on, 125 Food quality See also Processing and preservation techniques of food defined, 160 protein oxidation impact on (processing and storage), 123–125 Food systems character of, 237 defined, 236–237 elements of, associations with natural antioxidants, 237–238, 237f See also Natural antioxidants, in food systems 5-Formyl-5,6,7,8-tetrahydrofolic acid (5-FTHF) (folinic acid), 405f FOX assay See Ferrous oxidation-xylenol orange (FOX) assay Fragaria x ananasa (strawberries), 497 541 FRAP assay See Ferric-reducing ability of plasma (FRAP) assay; Ferric reducing/antioxidant power (FRAP) assay Free radicals, 2–3 roles of, sources of reactive nitrogen species, 327–328 reactive oxygen species, 326–327 Freezing prooxidant effect of, 144 Fruits antioxidants in, 280282 aỗai berries, 497 berries, 497–498 citrus fruits, 499–500 date palm, 498–499 exotic fruits, 500–501 persimmons, 499 pomegranate, 496–497 from waste and by-products of, 269, 271 color and flavor, 182–183 processes to stabilize, 183 FTC assay See Ferric thiocyanate (FTC) assay Functional antioxidant foods, 490–515 alcoholic drinks beer, 513–514 wine, 514–515 beverages, 510 cocoa, 513 coffee, 511–512 mate, 512–513 tea, 511 bioactive compounds with antioxidant activity carotenoids, 492–493 fibers, 495–496 flavonoids, 492, 492f, 493f phenolic acids, 491, 492f sterols and stanols, 495 tannins, 493494 terpenes, 494, 495f cereals, 506507 fruits aỗai berries, 497 berries, 497–498 citrus fruits, 499–500 date palm, 498–499 exotic fruits, 500–501 persimmons, 499 pomegranate, 496–497 legumes, 507–508 nuts and seeds, 508–509 oils argan oil, 505–506 coconut oil, 506 olive oil, 504–505 542 overview, 490–491 spices and herbs, 509–510 vegetables, 501 garlic, 502–503 onion, 503–504 tomatoes, 502 Functional meat products prooxidant effect of, 149 G Garlic (Allium sativum), 502–503 Gas chromatography–mass spectroscopy detection (GC-MS), 69 Gastrointestinal stability of curcuminoids, 439 GC-MS See gas chromatography–mass spectroscopy detection (GC-MS) γ-glutamic semialdehyde (GGS), 117 formation of, 49, 53f GGS See γ-glutamic semialdehyde (GGS) Glucuronic acids, 58–59 Glutamic acid (Glu), 405f Glutathione (GSH), 33, 326, 333–335, 334f, 391, 392 chemical structure, 409f Glutathione peroxidases (GPxs), 330 Glycogen, 57 GPxs See Glutathione peroxidases (GPxs) Grain products sensory characteristics, 183–185 GSH See Glutathione (GSH) Guanosine, 33 Guava (Psidium guajava L.), 501 H Haematococcus pluvialis (case studies), 479–481, 481f HDL See High-density lipoprotein (HDL) Hematoporphyrin, 33 Heme compounds peroxidation catalyzed by, Heme proteins, 21, 28–32 Hb See Hemoglobin (Hb) Mb See Myoglobin (Mb) mediated oxidation, 119–120, 120f metform of, 28 oxidizing power, 29–31 prooxidative capacity, 29–30 relative level in foods, 28–29 role in lipid oxidation, 104 Hemin, 29–30 capacity to promote free radicals formation, 30–31, 30f degradation of free, 24f Hemoglobin (Hb), 23, 28–32 Index capacity to promote free radicals formation, 30–31, 30f oxidative targets of, 28t oxidizing power, 29 oxygen binding affinity, 31–32 peroxidation catalyzed by, relative level in foods, 28–29 Hemoglobin–aldehyde interaction, 23–24 Herbs, antioxidant activity of, 390–391, 509–510 HHE (4-hydroxy-2-hexanal), High-density lipoprotein (HDL), 450 High hydrostatic pressure technology, 145–146 principle of, 146 prooxidant effect of, 145–147 High performance liquid chromatography (HPLC), 66 High-performance size-exclusion chromatography (HPSEC), 89, 91, 91f High pressures, in food processing, 317–318 High-pressure solvent extraction (HPSE), 467 HNE (trans-4-hydroxy-2-nonenal), HOCl See Hypochlorous acid (HOCl) Household cooking methods effect on lipid oxidation, 150 HPLC See High performance liquid chromatography (HPLC) HPLs See Hydroperoxide lyases (HPLs) HPSE (high-pressure solvent extraction), 467 HPSEC See High-performance size-exclusion chromatography (HPSEC) Hydrogen peroxide, in protein oxidation initiation, 118 Hydroperoxide lyases (HPLs), 36 Hydroperoxides, 13, 80 formation of, 81–83, 82f, 83t by photoxidation, 98 Hydrophobicity, 64 Hydroxybenzoic acids, 491 antioxidant activity of, 380–382, 381t 4-hydroxy-2-hexanal (HHE), 6, 23 Hydroxyl radical, Hypochlorous acid (HOCl), 38 I Indirect oxidation, of protein, 116, 121–123, 122f Indole-3-carbinol, 222 57th International Congress of Meat Science and Technology, Ghent, Belgium, 150 Iron, 24 Fe(III)/Fe(II) transition, redox potential of, 24–25, 25t in lipid oxidation, 139 role in protein oxidation, 117–119, 118f Iron-chelating agents, 22 Iron-reducing enzymatic systems, 25–27 activity of, 26, 27f 543 Index Irradiation, 144, 314–317, 316t induced oxidative chemical changes, 145 prooxidant effect of, 144–145 Isoflavones, 388, 492 K 3-Ketolipoic acid, 409f L LA See Lipoic acid (LA) Laccases, 39 Lactobionic acid, 58 Lactoperoxidase (LPO), 38–39 L-ascorbic acid See Ascorbic acid LC-MS See Liquid chromatography coupled with mass spectrometric detection (LC-MS) L-3,4-dihydroxyphenylalanine (L-DOPA), 39 LDL See Low-density lipoprotein (LDL) L-DOPA See L-3,4-dihydroxyphenylalanine (L-DOPA) Legumes, antioxidant activities of, 507–508 Light, effects of lipid oxidation, 10, 96 protein oxidation, 10, 120–121 Lignans, antioxidant activity of, 390 Linoleic acid peroxidation of, 163, 164f Lipid oxidation analysis of products, 66–67 autoxidation See Autoxidation consequences of, 8–9, 13, 15t–16t effect on sensory characteristics of food components, 162–167 enzymatic, 97–98 FA composition and, factors affecting, 9–10 antioxidants, 97 fatty acid composition, 97 food structure and lipid distribution, 99–101, 99f, 100f interactions between matrix components, 101 light, 10, 96 oxygen concentration, 96 prooxidants, 97 temperature, 9–10, 96 water activity, 10, 101–102 flavors and aromas produced in foods by, 166t–167t food nature and composition influence on emulsions, 102–103 fish products, 104–105 meat products, 104 processed foods, 105–107, 107f free radical oxidation mechanism, 163f mechanisms, 79–107 pathways and products of, 54–57, 55t, 56f photoxidation, 98–99, 98f technological process and, 10 vs protein oxidation, rate of, 10–11 Lipids, role in health and nutrition, 162–163 Lipids peroxidation See also Oxidation autoxidation, 3–4 See also Autoxidation catalyzed by trace metals and heme compounds, enzymatic, 4–5 initiation, oxysterols, photooxidation, secondary oxidation products, 5–6 Lipoic acid (LA), 335 chemical structure, 409f Lipoxygenases (LOXs), 4, 21, 35–38, 97–98 animal, classification of, 35 in cereal, 38 soybean, 37 Liquid chromatography coupled with mass spectrometric detection (LC-MS), 69 Liquid–liquid extraction (LLE), 466 Litchi chinensis (lychee), 501 LLE See Liquid–liquid extraction (LLE) LMW Cu oxidative targets of, 26t LMW Fe, 23 oxidative targets of, 26t Longan (Dimocarpus longan Lour.), 501 Low-density lipoprotein (LDL), 450, 504–505, 506, 507, 509 Low-molecular-weight (LMW) complexes, 22 iron, 22 LOXs See Lipoxygenases (LOXs) LPO See Lactoperoxidase (LPO) Lutein, 402 chemical structure, 403f Lychee (Litchi chinensis), 501 Lycium barbarum (wolfberries), 498 Lycopene, 402 chemical structure, 403f Lycopene cis-isomers, chemical structures of, 307f Lycopersicon esculentum (tomato), 502 M MAE See Microwave-assisted extraction (MAE) Maillard reaction, 12, 119, 123, 162, 304, 306 Maillard reaction products (MRPs) antioxidant activity of, 305f, 351–354, 352f, 353f structure, 305f 544 MALDI-TOF LC-MS See Matrix-Assisted Laser Desorption/Ionisation Time Of Flight Liquid Chromatography with Mass Spectrograph (MALDI-TOF LC-MS) Malonaldehyde/gas chromatography (MDA/GC) assay, 344, 346 Malonaldehyde/high-performance liquid chromatography (MDA/HPLC) assay, 344 Malonodialdehyde (MDA), 6, 346 Mangifera indica L (mango), 500 Mango (Mangifera indica L.), 500 MAP See Modified atmosphere packaging (MAP) technology Marinated herring production protein oxidation impact on, 124 Marine sources, of natural antioxidants, 251–252 Mate beverages, antioxidant activity of, 512–513 Matrix-Assisted Laser Desorption/ Ionisation Time Of Flight Liquid Chromatography with Mass Spectrograph (MALDI-TOF LC-MS), 66, 119 MCL See Methyl conjugated linoleate (MCL) MDA See Malonodialdehyde (MDA) MDA/GC assay See Malonaldehyde/gas chromatography (MDA/GC) assay MDA/HPLC assay See Malonaldehyde/highperformance liquid chromatography (MDA/HPLC) assay Meat lipid oxidation, promoting factors endogenous factors, 139–140 preslaughter factors, 140–141 processing and preservation techniques culinary cooking practices, 149–150 freezing and thawing, 144 functional meat products, 149 high hydrostatic pressure, 145–147 irradiation, 144–145 mechanical separation of meat, 142–144 packaging, 147–149 restructured meat products, 142–144 sodium chloride addition, 141–142 Meat products, 168, 170 color, 173–174 flavor, 170–173, 171t–172t functional, 149 influence of lipid oxidation, 104 See also Meat lipid oxidation mechanically separated, 142–144 protein oxidation impact on, 123–124 restructured, 142–144 Meat protein oxidation, promoting factors, 150–151 Mechanically separated meat products prooxidant effect of, 142–144 Index Metals chelation, 22 role in protein oxidation, 117–119, 118f MetHb See Methemoglobin (MetHb) Methemoglobin (MetHb), 23, 28, 29 Methyl conjugated linoleate (MCL) autoxidation of, 89, 91, 91f Methyl linoleate (ML), 89 5-Methyl-5,6,7,8-tetrahydrofolic acid (5-MTHF), 405f, 406 MetMb See Metmyoglobin (MetMb) Metmyoglobin (MetMb), 5, 28, 29, 30 Microalgal antioxidants and carotenoids (case studies), 476–477 Dunaliella salina, 477–479, 478f Haematococcus pluvialis, 479–481, 481f Microwave-assisted extraction (MAE), 469–470 Microwave heating, 311–312 Milk, carbohydrates in, 58 Modified atmosphere packaging (MAP) technology, 147–149 prooxidant effect of, 147–149 Monosaccharides, 57 Monounsaturated fatty acids (MUFAs), 27, 162f MPO See Myeloperoxidase (MPO) MRPs See Maillard reaction products (MRPs) MUFAs See Monounsaturated fatty acids (MUFAs) Myeloperoxidase (MPO), 38–39 Myoglobin (Mb), 23, 28–32 forms and characteristics, 169t oxidative targets of, 28t peroxidation catalyzed by, relative level in foods, 28–29 N NAD(P)H-dependent enzymatic systems, 26 activity of, 26, 27f Natural antioxidants, in food systems from agri-food waste and by-products cereals, seeds, and nuts, 271–273 fruits and vegetables, 269, 271 general aspects, 266–269, 268t, 270f oil production by-products, 273–274 amino acids, peptides, and proteins animal origin sources, 252–254 factors affecting antioxidant activity of, 256 general aspects, 245–251, 247f, 248t–251t marine sources, 251–252 plant origin sources, 254–256 case studies, 465–481 microalgal antioxidants and carotenoids, 476–481 rosemary antioxidants, 470–476 classification of, 240–245, 241t–244t in conventional organic food systems 545 Index berry fruits, 278–280 cereals, 286–287 fruits, 280–282 general aspects, 275–278 other crops and products, 287–289 vegetables, 282–286 defined, 236 extraction techniques compressed fluids extraction, instrumentation for, 468–469, 468f microwave and ultrasound-assisted extraction, 469–470 pressurized liquid extraction, 467 subcritical water extraction, 467–468 supercritical fluid extraction, 466–467 overview, 236–240 PS and OS antioxidants, 256–266, 258t–261t, 265f Natural flavorings, defined, 236 Natural product, defined, 236 Nitric oxide (NO•), 2–3, 327–328 NO• See Nitric oxide (NO•) Nonenzymatic antioxidants ascorbic acid, 330–332, 331f carotenoids, 335–336 flavonoids, 337–338, 337f glutathione, 333–335, 334f lipoic acid, 335 vitamin E, 332–333 Nonenzymatic oxidants, 22t heme proteins, 28–32 photosensitizers, 32–34 polyphenols and other reductants, 34 redox-active metals, 22–27 Nonflavonoids, 213, 214 Nonthermal processing of food enzymatic treatments, 312–313 fermentation, 313–314, 314f high pressures, 317–318 irradiation, 314–317, 316t pulsed electric fields, application of, 318–319, 318f separation, 318–319 n-3 PUFA, 140 Nutritive and health-promoting value of food oxidation effect on, 198–222 acyl lipids, 203–206 amino acids and proteins, 206–208 carbohydrates, 202–203 flavonoids and phenolic compounds, 213–216 overview, 198, 199t–201t terpenoid compounds, 208–213 vitamins, 216–222 Nuts antioxidants in, 508–509 from waste and by-products of, 271–273 O Odor, 161 Oil-in-water emulsions, 102 Oil production by-products antioxidants from, 273–274 Oils, 174 antioxidants in argan oil, 505–506 coconut oil, 506 olive oil, 504–505 flavor, 174–176 modification for stability, 177 oilseed-containing products, 177–178 processing for stability, 176 Olea europea L., 504 Oleic acid, 177 Olive by-products antioxidants from, 273 Olive oil, 504–505 Onion (Allium cepa L.), 503–504 OP See Oxidation potential (OP) ORAC See Oxygen radical absorbance capacity (ORAC) Organic food systems, conventional natural antioxidants in berry fruits, 278–280 cereals, 286–287 fruits, 280–282 general aspects, 275–278 other crops and products, 287–289 vegetables, 282–286 OS antioxidants, 256–266, 258t–261t OSI See Oxidative stability index (OSI) Oxidation See also Peroxidation carbohydrate See Carbohydrate oxidation consequences of food component, 12–16 effect on sensory characteristics of food components, 161–167 lipid See Lipid oxidation overview, 1–2 pigment, 167–168, 169t of pigments, 13 protein See Protein oxidation sources of, 2–3 Oxidation potential (OP), 47–72 AOXs, pathways and products of, 59–60 analysis of products, 68–69 ascorbic acid, 61–62, 62f carotenoids, 62–63 phenolic compounds, 60 tocopherols, 60–61, 61f carbohydrates oxidation, pathways and products of, 57 analysis of products, 67–68 in milk, 58 in plants, 58 546 sugars and alcohols, 58–59, 59f concept of, 48 cross-linking reactions, pathways and products of, 63–64 lipid oxidation, pathways and products of, 54–57, 55t, 56f, 66–67 measuring, 69–72, 70f, 72f overview, 47–48 proposed index of, 69–72, 70f, 72f protein oxidation, pathways and products of, 49–54, 50f, 51t–52t, 64–66 Oxidation reaction, 325 Oxidative stability index (OSI), 57 Oxidative stress, and disease, 434–435, 490 Oxidized monomers formation of, lipid oxidation and, 86, 87f, 88f Oxygen concentration effects on lipid oxidation, 96 Oxygen radical absorbance capacity (ORAC), 359 Oxylipins, 36 OxyMb (oxymyoglobin), Oxymyoglobin (OxyMb), Oxysterols, Ozone as ROS, 138 P Packaging modified atmosphere packaging (MAP) technology, 147–149 prooxidant effect of, 147–149 PAGE See Polyacrylamide gel electrophoresis (PAGE) Pasteurization, 304 Peanuts, 508 Peptides natural antioxidants from animal origin sources, 252–254 factors affecting antioxidant activity of, 256 general aspects, 245–251, 247f, 248t–251t marine sources, 251–252 plant origin sources, 254–256 Peroxidases (PODs), 58 Peroxidation, of lipids See also Oxidation autoxidation, 3–4 catalyzed by trace metals and heme compounds, enzymatic, 4–5 initiation, linoleic acid, 163, 164f oxysterols, photooxidation, secondary oxidation products, 5–6 Peroxide value (PV), 66 Peroxyl radicals, Peroxynitrite, Index Persimmons (Diospyros kaki L.), antioxidant capacity, 499 PFE (pressurized fluid extraction), 467 Phenolic acids, 128 defined, 491 as natural antioxidants, 491, 492f Phenolic AOXs, 60, 128–129, 129f Phenolic compounds antioxidant activity of, 376 cinnamic acids, 380–382, 381t flavonoids, 382–389, 383t–384t, 386f, 396 herbs and spices, 390–391 hydroxybenzoic acids, 380–382, 381t lignans, 390 tannins, 389–390 chemical structures, 213, 214f classification, 213–214, 376, 377t dietary sources and main representatives of, 377t metabolism and bioavailability of polyphenols, 377–380 oxidation, 214–215 effects on nutritive and health-promoting value, 215–216 prooxidant activity of, 376 flavonoids, 391–396, 392f, 393f 2-phenylbenzopyrylium (flavylium), 387 1-phenyl-3-methyl-5-pyrazolone (PMP), 68 Phoenix dactylifera L (date), 498–499 Phospholipids, 80 Photooxidation, Photosensitizers, 32–34, 98 type I/type II reactions, 32–33, 32f Photoxidation, 98–99, 98f Phytochemicals, 434 defined, 491 Pigment oxidation, 13 effect on sensory characteristics of food components, 167–168, 169t PIR See Protein interaction report (PIR) technology Pistachios, 508–509 Plant origin sources, of natural antioxidants, 254–256 Plants, carbohydrates in, 58 PLE See Pressurized liquid extraction (PLE) PLPW (pressurized low polarity water) extraction, 469 Polyacrylamide gel electrophoresis (PAGE), 65 Polymerization compounds formation of, lipid oxidation and, 89, 90f Polyphenol oxidases (PPOs), 39–40, 60 types of, 39 Polyphenols, 34, 434 bioavailability of, 377–380 biological properties of, 378 metabolism of, 377–380 Polysaccharides, 57 547 Index Polyunsaturated fatty acids (PUFAs), 3, 21, 27, 54, 162–163, 162f auto-oxidation of, 54–55, 56f, 81–82, 97–98, 139 Pomegranate (Punica granatum L.), antioxidant capacity, 496–497 Porphyrins, 32, 33 PPOs See Polyphenol oxidases (PPOs) Pressurized fluid extraction (PFE), 467 Pressurized liquid extraction (PLE), 467 Pressurized low polarity water (PLPW) extraction, 469 Processed foods influence of lipid oxidation, 105–107, 107f Processing and preservation techniques of food beneficial aspects, 303 nonthermal processes enzymatic treatments, 312–313 fermentation, 313–314, 314f high pressures, 317–318 irradiation, 314–317, 316t pulsed electric fields, application of, 318–319, 318f separation, 318–319 overview, 303–304 as promoting factors of meat oxidation culinary cooking practices, 149–150 freezing and thawing, 144 functional meat products, 149 high hydrostatic pressure, 145–147 irradiation, 144–145 mechanical separation of meat, 142–144 packaging, 147–149 restructured meat products, 142–144 sodium chloride addition, 141–142 thermal processes for food preservation, 306–309 for food transformation, 309–311, 310f goals, 304 microwave heating, 311–312 Processing and storage antioxidants use and, 127–128, 127t beneficial aspects, 303 protein oxidation impact on, 123–125 Prooxidant activity See also Antioxidant activity(ies) of ascorbic acid, 34, 61–62, 62f, 330–332, 331f, 399–400, 400f of β-carotene, 402–405 of carotenoids, 402–405 of flavonoids, 391–396, 392f, 393f of folates, 405–408 of vitamin E, 400–402 Prooxidants, effects on lipid oxidation, 97 Protein interaction report (PIR) technology, 65 Protein oxidation, 7–8, 206 of amino acid side chains, 206, 207f amino acids oxidation products detected in food, 117t analysis of products, 64–66, 65t consequences of, 8–9, 15t–16t, 54 direct, 116 effect on nutritive and health-promoting value, 206–208 FA composition and, factors affecting, 9–10 impact on food quality (processing and storage), 123–125 indirect, 116 initiation of heme proteins, 119–120, 120f indirect oxidation, 121–123, 122f light, 120–121 mechanisms, 116 metals, 117–119, 118f initiators of, light effects on, 10 pathways and products of, 49–54, 50f, 51t–52t prevention of, 125 antioxidants (feeding strategies), 125–126, 126t antioxidants (processing and storage strategies), 127–128, 127t carotenoids, 129–130 phenolic compounds, 128–129, 129f technological process and, 10 temperature effects on, 9–10 vs lipid oxidation, rate of, 10–11 water activity and, 10 Proteins, natural antioxidants from animal origin sources, 252–254 factors affecting antioxidant activity of, 256 general aspects, 245–251, 247f, 248t–251t marine sources, 251–252 plant origin sources, 254–256 Protoporphyrin, 33 Provitamin A carotenoids, 455–456 PS antioxidants, 256–266, 258t–261t, 265f Psidium guajava L (guava), 501 PUFAs See Polyunsaturated fatty acids (PUFAs) Pulsed electric fields application in food processing, 318–319, 318f Punica granatum L (pomegranate), 496–497 Pyridoxine antioxidant and prooxidant activity of, 409 Pyrogallol, 34 Q Quenchers, of singlet oxygen, 33t Quercetin, 385 prooxidant chemistry of, 393–394, 393f Quinones, 215 o-quinones, 60 548 R Radical-scavenging activity of apple, 362 See also DPPH• radical scavenging assay parameters characterization, 370–372 carotenoids and, 455 Reactive nitrogen species as sources of free radicals, 327–328 Reactive oxygen species (ROS), 2–3, 49, 115 in biological systems, 2f, 115–116 endogenous formation, 137–138 external sources, 138 ozone, 138 role in oxidative processes, 138 as sources of free radicals, 326–327 Redox-active metals, 21, 22–27 distribution of, 23 Redox buffering, 326 Redox reactions, 325 Redox theory of cellular function, 325–326 Red raspberries (Rubus idaeus), 498 Reduction reaction, 325 Restructured meat products prooxidant effect of, 142–144 Riboflavin, 12, 32, 33–34 chemical structures, 218f oxidation, effect on nutritive and healthpromoting value, 217, 218f ROS See Reactive oxygen species (ROS) Rosemary antioxidants (case study), 470–476 activity of extracts, 473–474 background, 470–471 carnosic acid, 471–472 chemical structures, 471f extraction–adsorption–desorption procedure for, 474–475, 474f extraction processes, 472–473 raw material and processing conditions, 472 SFE for, 472–473 Rosmadial, chemical structure, 471f Rosmarinic acid, 128 chemical structure, 391f, 471f Rosmarinus officinalis L (rosemary), 470 Rubus fruticosus (blackberries), 497 Rubus idaeus (red raspberries), 498 Rubus occidentalis (black raspberries), 497–498 S Saccharides, oxidation of, 11–12 Salting methods effects on lipid oxidation, 141–142 Saturated fatty acids, 162f SDS See Sodium dodecyl sulfate (SDS) SDS-PAGE, 65 Secondary plant metabolites, 434 Index Seeds antioxidants in, 508–509 from waste and by-products of, 271–273 Sensory characteristics, of food components dairy products, 178–179 fruit color and flavor, 182–183 processes to stabilize, 183 grain products, 183–185 meat, 168, 170 color, 173–174 flavor, 170–173, 171t–172t oils, 174 flavor, 174–176 modification for stability, 177 oilseed-containing products, 177–178 processing for stability, 176 overview, 160 oxidation effect on, 161–162 lipid oxidation, 162–167 pigment oxidation, 167–168 sensory evaluation, 160–161 vegetable color and flavor, 179–180 processes to stabilize, 180–182 Sensory evaluation, 160 color, 161 flavor, 161 odor, 161 taste, 160 SFE See Supercritical fluid extraction (SFE) Singlet oxygen, 2, 4, 33, 62 chemical quenchers of, 33t oxidation of oleate by, 98, 98f physical quenching of , in carotenoids, 454 SLE See Solid–liquid extraction (SLE) SOD See Superoxide dismutase (SOD) Sodium chloride (NaCl) addition prooxidant effect of, 141–142 Sodium dodecyl sulfate (SDS), 65 Solid–liquid extraction (SLE), 466 Spectrophotometer, antioxidant assays using, 344–346, 345t Spices, antioxidant activity of, 390–391, 509–510 Stanols, with antioxidant activity, 495 Sterilization, 304 Sterols, 80 with antioxidant activity, 495 oxidation of, 211–212, 212f effects on nutritive and health-promoting value, 213 Strawberries (Fragaria x ananasa), 497 Subcritical water extraction (SWE), 467–468 Sugars (aldoses), 58 oxidation chemistry of, 58–59, 59f Supercritical fluid extraction (SFE), 466–467 Superoxide anion radical, Superoxide dismutase (SOD), 328–329 SWE See Subcritical water extraction (SWE) 549 Index T TAC See Total antioxidant capacity (TAC) Tannins, antioxidant activity of, 389–390, 493–494 Taste, 160 TBA assay See Thiobarbituric acid (TBA) assay Tea, antioxidant activity of, 350–351, 511 TEAC See Trolox equivalent antioxidant capacity (TEAC) Technological process effects on lipid and protein oxidation, 10 Temperature, effects of lipid oxidation, 9–10, 96 protein oxidation, 9–10 Terpenes, with antioxidant activity, 494, 495f Terpenoid compounds oxidation, effect on nutritive and healthpromoting value, 208 carotenoids, 210–211 sterols, 211–213, 212f tocopherol and tocotrienol, 208–210, 209f 5,6,7,8-Tetrahydrofolic acid (THF), 405f, 406 Thawing prooxidant effect of, 144 Theaflavins, 387 Thearubigins, 387 Thermal processing of food goals, 304 microwave heating, 311–312 for preservation, 306–309 for transformation, 309–311, 310f Thermoxidation, 93–96, 94f Thiamin chemical structures, 217f oxidation, effect on nutritive and healthpromoting value, 216–217, 217f Thiamine deficiency, 409 Thiobarbituric acid (TBA) assay, 344, 346 Thiol antioxidants, 409–410 chemical structures, 409f Thioredoxin (TRX), 326 Thymol, 391f Tocopherols, 60–61, 61f, 400 oxidation of, 208, 209f effects on nutritive and health-promoting value, 210 structure, 401f α-Tocopherol, 33, 400, 401, 401f antioxidant activities of vs carotenoids, 404t vs folates, 407t Tocotrienols, 400 oxidation of, 208, 209f effects on nutritive and health-promoting value, 210 structure, 401f Tomato (Lycopersicon esculentum), 502 Total antioxidant capacity (TAC), 306, 360 See also Antioxidant activity(ies) Trace metals peroxidation catalyzed by, Trans-4-hydroxy-2-nonenal (HNE), Transition metals role in lipid oxidation, 139 role in protein oxidation, 117–119, 118f Triacylglycerols (TAGs), 80 Trolox equivalent antioxidant capacity (TEAC), 359 TRX See Thioredoxin (TRX) Tyrosinases, 39 Tyrosine t-butyl ester (TBT), 68 U UAE See Ultrasound-assisted extraction (UAE) Ultrasound-assisted extraction (UAE), 469–470 Unsaturated fatty acids, 162f auto-oxidation of, 54–55, 56f V Vaccinium corymbosum (blueberries), 497 Vegetables antioxidants in, 282–286, 501 garlic, 502–503 onion, 503–504 tomatoes, 502 from waste and by-products of, 269, 271 color and flavor, 179–180 processes to stabilize, 180–182 Very low density lipoprotein (VLDL), 450 Virgin coconut oil (VCO), 506 Virgin olive oil, 504 Vitamin B6 chemical structures, 219f oxidation, effect on nutritive and healthpromoting value, 217, 219, 219f Vitamin B12 chemical structures, 221f oxidation, effect on nutritive and healthpromoting value, 221–222, 221f Vitamin C See Ascorbic acid (vitamin C) Vitamin D, 12 Vitamin E, 332–333 antioxidant and prooxidant activity of, 400–402 structures, 401f Vitamins oxidation, effect on nutritive and healthpromoting value ascorbic acid, 216 biotin, 220, 221f folate, 219, 220f riboflavin, 217, 218f thiamin, 216–217, 217f 550 Index vitamin B6, 217, 219, 219f vitamin B12, 221–222, 221f VLDL See Very low density lipoprotein (VLDL) Volatile compounds formation of, lipid oxidation and, 83–86, 84f, 85f, 86t, 96 Volatile oils, 128 Water activity lipid oxidation and, 10, 101–102 protein oxidation and, 10 Water-in-oil emulsions, 102 ω-3 fatty acids, 205 Wine, antioxidant activity of, 514–514 Wolfberries (Lycium barbarum), 498 W Z Walnuts, 509 Warmed-over flavor (WOF) in meats, 139 Zeaxanthin, 402 chemical structure, 403f ... Saccharides Edited by Piotr Tomasik Chemical and Functional Properties of Food Proteins Edited by Zdzisław E Sikorski Food Oxidants and Antioxidants Chemical, Biological, and Functional Properties EDITED. . .Food Oxidants and Antioxidants Chemical, Biological, and Functional Properties Chemical and Functional Properties of Food Components Series SERIES EDITOR Zdzisław E Sikorski Food Oxidants and. .. Oxidants and Antioxidants: Chemical, Biological, and Functional Properties Edited by Grzegorz Bartosz Fermentation: Effects on Food Properties Edited by Bhavbhuti M Mehta, Afaf Kamal-Eldin and Robert